# US 5,346,808 A · Positive image formation utilizing o-quinonediazide composition including selected phenolic derivatives of 4-(4-hydroxyphenyl)-cyclohexanone

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- Number: US 5,346,808 A
- Document ID: US5346808A
- Status: Granted
- Kind: A
- Application number: 08/148,235
- Filed: 1993-11-08
- Granted: 1994-09-13
- Earliest claimed: 1993-04-05
- Assignees: OCG Microelectronic Materials, Inc.
- Inventors: Alfred T. Jeffries, III
- Web page: https://patentgrep.com/patent/US5346808A

## CPC

- C07C 39/17: containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol}
- G03F 7/0226: {characterised by the non-macromolecular additives}
- Y10S 430/143: Electron beam
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

A radiation-sensitive composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one photoactive compound and an effective sensitivity enhancing amount of at least one compound of formula (I): ##STR1## wherein each R is individually selected from the group consisting of hydrogen and a lower alkyl group having 1-4 carbon atoms and each n is 0, 1, or 2; the amount of said binder resin being about 60 to 95% by weight, the amount of said photoactive component being about 5% to about 40% by weight, based on the total solids content of said radiation-sensitive composition.

## Claims

### Claim 1

The process of developing an image-wise exposed photoresist-coated substrate to form a positive-working image comprising:
(a) coating said substrate with a radiation-sensitive composition useful as a photoresist, said composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one o-quinonediazide photoactive compound, and an effective sensitive enhancing amount of at least one phenolic derivative of 4-(4-hydroxyphenol) cyclohexanone compound of formula (I): ##STR9## where each R is individually selected from the group consisting of hydrogen and a lower alkyl group having 1-4 carbon atoms and each n is 0, 1, or 2; the amount of said binder resin being about 60 to 95% by weight, the amount of said photoactive compound being about 5% to about 50% by weight, based on the total solids content of said radiation-sensitive composition;
(b) subjecting said coating on said substrate to an image-wise exposure of radiant light energy; and
(c) subjecting said image-wise exposed coated substrate to a developing solution to form a positive-working, image-wise pattern in the coating.

### Claim 2 (depends on 1)

The process of claim 1 wherein said binder resin is an alkali-soluble phenolic novolak resin.

### Claim 3 (depends on 1)

The process of claim 1 wherein said o-quinonediazide compound or compounds are present in the amount of about 10% to about 25% by weight, said binder resin is present in the amount of about 75% to about 90% by weight, and said phenolic derivative of 4-(4-hydroxyphenol) cyclohexanone is present in the amount of 0.5% to about 10% by weight, all based on the total solids content of said radiation-sensitive composition.

### Claim 4 (depends on 1)

The process of claim 1 wherein said phenolic derivative of 4-(4-hydroxyphenol) cyclohexanone is present in the amount of from about 2% to about 4% by weight, based on the total solids content of said radiation-sensitive composition.

### Claim 5 (depends on 1)

The process of claim 1 wherein said phenolic derivative of 4-(4-hydroxyphenol) cyclohexanone is 1,1,4-tris(4-hydroxyphenyl) cyclohexanone.

### Claim 6 (depends on 1)

The process of claim 1 wherein said radiant light energy is selected from the group consisting of ultraviolet light radiation and electron beam radiation.

### Claim 7 (depends on 1)

The process of claim 1 wherein said developing solution is an aqueous solution of an alkali selected from the group consisting of tetramethylammonium hydroxide, sodium hydroxide, potassium hydroxide, ethanolamine, choline, sodium phosphates, sodium carbonate, and sodium metasilicates.