# US 2014/0154632 A1 · Perfluoroalkyl sulfonamides surfactants for photoresist rinse solutions

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- Number: US 2014/0154632 A1
- Document ID: US20140154632A1
- Status: Published application
- Kind: A1
- Application number: 14/237,193
- Filed: 2012-08-01
- Published: 2014-06-05
- Earliest claimed: 2011-08-10
- Assignees: 3M Innovative Properties Company
- Applicants: 3M Innovative Properties Company
- Inventors: Jason M. Kehren; Patricia M. Savu; Matthew J. Pinnow
- Web page: https://patentgrep.com/patent/US20140154632A1

## CPC

- G03F 7/40: Treatment after imagewise removal, e.g. baking
- G03F 7/405: {Treatment with inorganic or organometallic reagents after imagewise removal}
- H10P 76/204: {of organic photoresist masks}
- 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)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A method of modifying a surface of a photoresist material including exposing the photoresist material to an aqueous ionic surfactant solution and varying the pH of the aqueous ionic surfactant solution until a fluorochemical layer is formed in or on the photoresist material. The aqueous ionic surfactant solution includes a perfluoroalkyl sulfonamide the formula: RfS02NH—R′ where Rf=CnF2n+1— and n=1 to 6, R′=—H, —CH3, and —CH2CH2OH. The aqueous ionic surfactant solution has a pH of within about 3 pH units of a pKa of the perfluoroalkyl sulfonamide.

## Claims

### Claim 1

A method of modifying a surface of a photoresist material comprising:
exposing the photoresist material to an aqueous ionic surfactant solution comprising a perfluoroalkyl sulfonamide having Formula I:
RfSO2NH—R′ (I)
where Rf=CnF2n+1— and n=1 to 6, R′=—H, —CH3, and —CH2CH2OH; and
varying the pH of the aqueous ionic surfactant solution until a fluorochemical layer is formed in or on the photoresist material;
wherein the aqueous ionic surfactant solution has a pH of within about 3 pH units of a pKa of the perfluoroalkyl sulfonamide.

### Claim 2 (depends on 1)

The method of claim 1, wherein the aqueous ionic surfactant solution has a pH of within about 2 pH units of the pKa of the perfluoroalkyl sulfonamide.

### Claim 3 (depends on 1)

The method of claim 1, wherein varying the pH of the aqueous ionic surfactant solution comprises substantially no melting of the photoresist material.

### Claim 4 (depends on 1)

The method of claim 1, wherein varying the pH of the aqueous ionic surfactant solution comprises forming substantially no deformities on the photoresist material.

### Claim 5 (depends on 1)

The method of claim 1, wherein the aqueous ionic surfactant solution has a concentration of between about 10 ppm and about 10,000 ppm.

### Claim 6 (depends on 5)

The method of claim 5, wherein the aqueous ionic surfactant solution has a concentration of between about 50 ppm and about 5,000 ppm.

### Claim 7 (depends on 1)

The method of claim 1, wherein the aqueous ionic surfactant solution has a neutral sulfonamide to sulfonamide salt ratio of between about 99.9:0.1 and about 0.1:99.9.

### Claim 8 (depends on 1)

The method of claim 1, further comprising drying the photoresist material to remove the aqueous ionic surfactant solution.

### Claim 9 (depends on 1)

The method of claim 1, further comprising rinsing the photoresist material with deionized water.

### Claim 10 (depends on 1)

The method of claim 1, wherein n=4.

### Claim 11 (depends on 1)

The method of claim 1, wherein the aqueous ionic surfactant solution is selected from the group consisting of: C4F9SO2N(H)CH2CH2OH, C4F9SO2NH2, and C4F9SO2N(H)CH3.

### Claim 12 (depends on 1)

The method of claim 1, wherein the photoresist is a patterned photoresist.