IP Library Granted Patent US 10,962,880
Granted Patent B2
US 10,962,880 · App. 16/715,178 · Granted Mar 30, 2021

Radiation-sensitive compositions and patterning and metallization processes

Inventors: Mitsuru Haga (Minamikanbara-gun, JP); Shugaku Kushida (Niigata, JP); Kunio Kainuma (Shibata, JP); James F. Cameron (Brookline, MA)
Assignee: Rohm and Haas Electronic Materials LLC
G03F7/0045C23C18/1612C23C18/1667C23C18/1689C23C18/1844C23C18/38G03F7/0035G03F7/0046G03F7/039G03F7/0392G03F7/0397G03F7/2002G03F7/2004G03F7/2006G03F7/322G03F7/40H01L21/32056
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Quick Facts
Patent No.
US 10,962,880
App. No.
16/715,178
Granted
Mar 30, 2021
Kind
B2
Abstract

A patterning process, comprises: (i) forming a radiation-sensitive film on a substrate, wherein the radiation-sensitive film comprises: (a) a resin, (b) a photoacid generator, (c) a first quencher, and (d) a second quencher; (ii) patternwise exposing the radiation-sensitive film to activating radiation; and (iii) contacting the radiation-sensitive film with an alkaline developing solution to form a resist pattern; wherein the resin comprises the following repeat units: wherein: R 1 is selected from a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a cyano group or a trifluoromethyl group; Z is a non-hydrogen substituent that provides an acid-labile moiety; n is from 40 to 90 mol %; m is from 10 to 60 mol %; and the total combined content of the two repeat units in the resin is 80 mol % or more based on all repeat units of the resin; and the first quencher is selected from benzotriazole or a derivative thereof.

Claims (11)

1. A radiation-sensitive composition, comprising: (a) a resin; (b) two or more photoacid generators; (c) a first quencher; (d) a second quencher; and (e) a solvent;

wherein the resin comprises the following two repeat units:

wherein: R 1 is selected from a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, a cyano group or a trifluoromethyl group; Z is a non-hydrogen substituent that provides an acid-labile moiety; n is from 40 to 90 mol %; m is from 10 to 60 mol %; and the total combined content of the two repeat units in the resin is 80 mol % or more based on all repeat units of the resin;

wherein the photoacid generators are selected from N-hydroxynaphthalimide trifluoromethanesulfonate, N-hydroxynaphthalimide perfluoro-1-butanesulfonate, N-hydroxynaphthalimide camphor-10-sulfonate, N-hydroxynaphthalimide 2-trifluoromethylphenylsulfonate, N-hydroxy-5-norbornene-2,3-dicarboximide perfluoro-1-butanesulfonate, N-(trifluoromethylsulfonyloxy)phthalimide and N-hydroxysuccinimide perfluorobutanesulfonate;

wherein the first quencher is selected from benzotriazole or its derivatives;

wherein the second quencher is selected from N,N-diethyldodecanamide, 2,8-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine,1,1-dimethylethyl 4-hydroxypiperidine-1-carboxylate and N-allylcaprolactam; and

wherein the solid content of the composition is from 10 to 60 weight %.

2. The radiation-sensitive composition of claim 1 , wherein the composition is sensitive to activating radiation having a wavelength of 365 nm.

3. The radiation-sensitive composition of claim 1 , wherein the resin has a weight average molecular weight of from 10,000 to 30,000 Daltons.

4. The radiation-sensitive composition of claim 1 , wherein the amount of the first quencher is from 0.001 to 1.0 wt % based on the weight of the resin.

5. The radiation-sensitive composition of claim 1 , wherein the amount of the second quencher is from 0.001 to 1.0 wt % based on the weight of the resin.

Assignments (3)
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 →