# US 9,436,082 B2 · Compositions comprising base-reactive component and processes for photolithography

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- Number: US 9,436,082 B2
- Document ID: US9436082B2
- Status: Granted
- Kind: B2
- Application number: 13/341,067
- Filed: 2011-12-30
- Published: 2012-07-05
- Granted: 2016-09-06
- Earliest claimed: 2010-12-30
- Assignees: Rohm and Haas Electronics Materials LLC
- Applicants: Deyan Wang; Shintaro Yamada; Cong Liu; Mingqi Li; Joon-Seok Oh; Chunyi Wu; Doris Kang; Cheng-Bai Xu
- Inventors: Deyan Wang; Shintaro Yamada; Cong Liu; Mingqi Li; Joon-Seok Oh; Chunyi Wu; Doris Kang; Cheng-Bai Xu
- Web page: https://patentgrep.com/patent/US9436082B2

## CPC

- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- G03F 7/30: Imagewise removal using liquid means
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

New photoresist compositions are provided that comprise one or more materials that have base-reactive groups and are particularly useful for dry lithography. Particularly preferred photoresists of the invention can exhibit reduced defects following development of a coating layer of the resist.

## Claims

### Claim 1

A method for processing a photoresist composition, comprising:
(a) applying on a substrate a photoresist composition comprising:
(i) one or more resins,
(ii) a photoactive component, and
(iii) one or more materials that comprise base-reactive groups, the one or more materials distinct from the one or more resins; and
(b) dry exposing the applied photoresist layer to radiation activating for the photoresist composition;
wherein said (iii) one or more materials comprise a resin that comprises a repeat unit provided by at least one monomer represent by the following Formula (I), (II) or (III):
where in Formula (I) M is a polymerizable functional group, R is an alkyl spacer group with or without carboxyl linkages, Rf is a fluoro or perfluoro alkyl group with at least the alpha carbon being fluorinated;
wherein in Formula (II) M is a polymerizable functional group, R is C1-20 linear or branched alkyl spacer group with or without carboxyl linkages, Rf is a fluoro or perfluoro alkyl group with at least the alpha carbon being fluorinated, and n is an integer equal to or greater than 2;
wherein in Formula (III) M is a polymerizable functional group R1 is an alkyl spacer with or without carboxyl linkages, Rf is a fluoro or perfluoro alkylene group with at least the alpha carbon being fluorinated, and R2 is an alkyl group.

### Claim 2 (depends on 1)

The method of claim 1 wherein the one or more materials migrate toward upper portions of the photoresist composition layer during the applying.

### Claim 3 (depends on 1)

The method of claim 1 wherein the (iii) one or more materials have a lower surface energy than the (i) one or more resins.

### Claim 4 (depends on 1)

The method of claim 1 wherein the one or more materials comprises photoacid-labile groups.

### Claim 5 (depends on 1)

The method of claim 1 further comprising developing the exposed photoresist layer with aqueous alkaline developer whereby the one or more base-reactive groups undergo a bond-breaking reaction to provide one or more polar groups.

### Claim 6 (depends on 5)

The method of claim 5 wherein the photoresist layer after development has a water contact receding angle of less than 30°, and/or the photoresist layer prior to development has a water contact receding angle of in excess of 40°.

### Claim 7 (depends on 1)

The method of claim 1 wherein the (iii) one or more materials comprise a repeat unit provided by at least one monomer of Formula (I).

### Claim 8 (depends on 1)

The method of claim 1 wherein the (iii) ore or more materials comprise a repeat unit provided by at least one monomer of Formula (II).

### Claim 9 (depends on 1)

The method of claim 1 wherein the (iii) one or more materials comprise a repeat unit provided by at least one monomer of Formula (III).