Polymers and photoresist compositions

Patent metadata

Field	Value
Publication number	US-10670965-B2
Application number	US-201113077947-A
Country	US
Kind code	B2
Filing date	Mar 31, 2011
Priority date	Mar 31, 2010
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

New polymers are provided comprising (i) one or more covalently linked photoacid generator moieties and (ii) one or more photoacid-labile groups, wherein the one or more photoacid generator moieties are a component of one or more of the photoacid-labile groups. Preferred polymers of the invention are suitable for use in photoresists imaged at short wavelengths such as sub-200 nm, particularly 193 nm.

First claim

What is claimed is:

1. A method for producing an electronic device, comprising:
applying a coating layer of a photoresist composition on a substrate, wherein the photoresist composition comprises:
a resin comprising (i) one or more sulfonic acid photoacid generator moieties covalently linked to the resin; and (ii) one or more photoacid-labile groups,
wherein the one or more sulfonic acid photoacid generator moieties are a component of one or more of the photoacid-labile groups, and
wherein the one or more sulfonic acid photoacid generator moieties comprise a structure c of R(CY 2 ) n (CF 2 ) 2 SO 3 — where n is an integer of 1 to 5, each Y is the same or different and is hydrogen, halo, optionally substituted alkyl wherein one or more Y is C 1-20 haloalkyl, and R is a chemical bond or a non-hydrogen substituent;
exposing the photoresist coating layer to patterned activating radiation; and developing the exposed photoresist coating layer to provide a photoresist relief image; and
wherein photoinduced reaction of the photoacid-labile groups results in cleavage of a sulfonic acid from the resin.

2. The method of claim 1 , wherein the resin comprising photoacid generator groups further comprises carbon alicyclic, heteroalicyclic, anhydride, lactone, naphthyl, hydroxyl and/or acrylate groups.

3. The method of claim 1 , wherein the resin comprising photoacid generator groups further comprises polymerized units of 2-methyladamantylacrylate, hydroxyadamantylacrylate, hydroxyadamantylmethacrylate, maleic anhydride, norbornene, 3,4-dihydropyran, optionally substituted phenyl and/or optionally substituted naphthyl.

4. The method of claim 1 wherein each Y is fluoro or C 1-6 fluoroalkyl with at least one Y being C 1-6 fluoroalkyl.

5. The method of claim 1 wherein the photoresist composition is immersion exposed with 193 nm patterned activating radiation.

6. The method of claim 1 wherein each Y is hydrogen, fluoro or —CF 3 where at least one Y is —CF 3 .

7. The method of claim 1 wherein n is 1, 2 or 3.

8. The method of claim 7 wherein one or more Y is fluoroalkyl.

9. The method of claim 7 wherein one or more Y is —CF 3 .

10. The method of claim 7 wherein each Y is hydrogen, fluoro or —CF 3 where at least one Y is —CF 3 .

11. A method for producing an electronic device, comprising:
applying a coating layer of a photoresist composition on a substrate, wherein the photoresist composition comprises:
a resin comprising (i) one or more non-ionic photoacid generator moieties covalently linked to the resin; and (ii) photoacid-labile groups,
wherein the one or more photoacid generator moieties are a component of one or more of the photoacid-labile groups;
exposing the photoresist coating layer to patterned activating radiation; and

developing the exposed photoresist coating layer to provide a photoresist relief images.

12. The method of claim 11 wherein the one or more photoacid generator moieties comprise one or more imidosulfonate moieties, one or more oxime sulfonate moieties, one or more N-oxyimidosulfonate moieties, one or more disulfone moieties, one or more N-sulfonyloxyimide moieties, and one or more nitrobenzyl moieties.

13. The method of claim 11 wherein the photoresist composition is immersion exposed with 193 nm patterned activating radiation.

14. A method for producing an electronic device, comprising:
applying a coating layer of a photoresist composition on a substrate, wherein the photoresist composition comprises:
a resin comprising (i) one or more photoacid generator moieties covalently linked to the resin; and (ii) one or more photoacid-labile groups,
wherein the one or more photoacid generator moieties are a component of one or more of the photoacid-labile groups;
exposing the photoresist coating layer to patterned activating radiation; and developing the exposed photoresist coating layer to provide a photoresist relief image;
wherein the one or more photoacid generator moieties comprise polymerized units of one or more of the following:

15. The method of claim 14 , wherein the photoresist composition is immersion exposed with 193 m patterned activating radiation.

16. A method for producing an electronic device, comprising:
applying a coating layer of a photoresist composition on a substrate, wherein the photoresist composition comprises:
a resin comprising (i) one or more sulfonic acid photoacid generator moieties covalently linked to the resin; and (ii) one or more photoacid-labile groups,
wherein the one or more sulfonic acid photoacid generator moieties are a component of one or more of the photoacid-labile groups, and
wherein the one or more sulfonic acid photoacid generator moieties comprise a structure of R(CY 2 ) n (CF 2 ) 2 SO 3 − where n is 1, 2 or 3, each Y is the same or different and is hydrogen, halo or optionally substituted alkyl wherein one or more Y is C 1-20 haloalkyl, and R is a chemical bond or a substituted ester;
exposing the photoresist coating layer to patterned activating radiation; and

developing the exposed photoresist coating layer to provide a photoresist relief image; and
wherein photoinduced reaction of the photoacid-labile groups results in cleavage of a sulfonic acid from the resin.

Assignees

• Aqad Emad
• Liu Cong
• Xu Cheng Bai
• Li Mingqi
• Rohm & Haas Elect Mat

Inventors

• Aqad Emad
• Liu Cong
• Xu Cheng-Bai
• Li Mingqi

Classifications

• G03F7/0392 Primary

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title