Photoresists comprising amide component

Patent metadata

Field	Value
Publication number	US-10719014-B2
Application number	US-201313926764-A
Country	US
Kind code	B2
Filing date	Jun 25, 2013
Priority date	Jun 25, 2012
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

New photoresist compositions are provided that comprise a component that comprises an amide group and multiple hydroxyl groups. Preferred photoresists of the invention may comprise a resin with photoacid-labile groups; a photoacid generator compound; and an amide component with multiple hydroxyl groups that can function to decrease undesired photogenerated-acid diffusion out of unexposed regions of a photoresist coating layer.

First claim

What is claimed is:

1. A photoresist composition comprising:
(a) a resin;
(b) a photoacid generator compound; and
(c) a non-polymeric amide compound that comprises i) an amide group, ii) two or more hydroxyl groups and iii) one or more cyano groups and/or one or more carboxyl group.

2. The photoresist composition of claim 1 wherein the amide compound contains a single amide moiety.

3. The photoresist composition of claim 1 wherein the amide compound corresponds to a structure of the following Formula (I):

wherein R1, R2 and R3 are each independently hydrogen or a non-hydrogen substituent; and R1, R2 and R3 together comprise two or more hydroxyl groups.

4. The photoresist composition of claim 3 wherein R1 is a non-hydrogen substituent and at least one of R2 and R3 are non-hydrogen substituents.

5. The photoresist composition of claim 3 wherein R1 is optionally substituted alkyl, and R2 and R3 are independently hydrogen or optionally substituted alkyl.

6. The photoresist composition of claim 3 wherein R1, R2 and R3 are each the same or different optionally substituted alkyl.

7. The photoresist of claim 3 wherein 1) R1 and R2 are taken together to provide an optionally substituted lactam group and/or 2) R2 and R3 are taken together to provide a ring structure.

8. The photoresist composition of claim 3 wherein R1 is (C 1 -C 30 )alkyl optionally substituted with a hydroxyl group, and R2 and R3 are independently hydrogen or a (C 1 -C 30 )alkyl optionally substituted with a hydroxyl group, and R1, R2 and R3 together comprise two or more hydroxyl groups.

9. The photoresist composition of claim 1 wherein the amide compound comprises three or more hydroxyl groups.

10. The photoresist composition of claim 1 wherein the amide compound comprises at least one primary hydroxyl group.

11. The photoresist composition of claim 1 wherein the amide compound comprises at least one secondary hydroxyl group.

12. The photoresist composition of claim 1 wherein the amide compound comprises one or more carboxyl groups.

13. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 2500 or less.

14. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 1500 or less.

15. The photoresist composition of claim 1 wherein the amide compound has a molecular weight of about 500 or less.

16. A method for forming a photoresist relief image comprising:
(a) applying a coating layer of a photoresist composition of claim 1 on a substrate;
(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

17. The method of claim 16 wherein the photoresist coating layer is immersion exposed.

18. A method for forming a photoresist relief image comprising:
(a) applying on a substrate a coating layer of a photoresist composition that comprises:
(i) a resin;
(ii) a photoacid generator compound; and
(iii) an amide compound that corresponds to a structure of the following Formula (I):

wherein R1 is (C 1 -C 30 )alkyl optionally substituted with a hydroxyl group, and R2 and R3 are independently hydrogen or a (C 1 -C 30 )alkyl optionally substituted with a hydroxyl group, and R1, R2 and R3 together comprise two or more hydroxyl groups, and
wherein 1) R1 and R2 are taken together to provide an optionally substituted lactam group and/or 2) R2 and R3 are taken together to provide a ring structure,
(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Liu Cong
• Wu Chunyi
• Pohlers Gerhard
• Prokopowicz Gregory P
• Li Mingqi
• Xu Cheng-Bai

Classifications

• G03F7/004 Primary

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08F220/58 Primary

  containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine} · CPC title

• G03F7/0382

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

• G03F7/039

  Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023) · CPC title

• G03F7/2002

  with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image · CPC title