# US 5,348,842 A · Method for producing positive photoresist image utilizing diazo ester of benzolactone ring compound and diazo sulfonyl chloride > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,348,842 A - Document ID: US5348842A - Status: Granted - Kind: A - Application number: 08/042,362 - Filed: 1993-04-02 - Granted: 1994-09-20 - Earliest claimed: 1992-03-06 - Assignees: Hoechst Celanese Corporation - Inventors: Dinesh N. Khanna; Douglas McKenzie; Chester J. Sobodacha; Ralph R. Dammel - Web page: https://patentgrep.com/patent/US5348842A ## CPC - G03F 7/022: Quinonediazides (G03F7/075 takes precedence) - Y10S 430/168: X-ray exposure process - 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 photosensitizer comprising a diazo ester of benzolactone ring compound, such as phenolphthalein or cresolphthalein as the backbone, where at least one of the hydroxy groups on benzolactone ring has been esterified with diazo-sulfonyl chloride consisting of 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride or a mixture thereof, and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition and a suitable solvent. ## Claims ### Claim 1 A method for producing a photoresist image on a substrate commensurate in scope with the developing step wherein the imagewise exposed areas of the positive working photosensitive composition are removed with an aqueous alkaline developer, which comprises coating a substrate with a positive working photosensitive composition which composition comprises in admixture: (a) a photosensitive component comprising a diazo ester of a benzolactone ring compound, where the diazo ester is a compound containing at least one hydroxy group on the benzolactone ring have been esterified with diazo sulfonyl chloride consisting of 60 to 100 mole % 2,1,4 or 2,1,5 diazo sulfonyl chloride or a mixture thereof, said photosensitive component being present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; and (b) a water insoluble, aqueous alkali soluble novolak resin; said novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition; and (c) a solvent composition; and heat treating said coated substrate until substantially all of said solvent composition is removed; imagewise exposing said photosensitive composition to actinic radiation; and removing the imagewise exposed areas of said composition with an aqueous alkaline developer. ### Claim 2 (depends on 1) The method of claim 1 further comprising heating said coated substrate from a temperature of from about 90.degree. C. to about 150.degree. C. for from about 30 seconds to about 180 seconds on a hot plate or from about 15 minutes to about 40 minutes in an oven after the exposure step but before the removing step. ### Claim 3 (depends on 1) The method of claim 1 further comprising heating said coated substrate at a temperature of from about 90.degree. C. to about 150.degree. C. for about 30 seconds to about 180 seconds on a hot plate or for from about 15 minutes to about 40 minutes in an oven after the removing step. ### Claim 4 (depends on 1) The method of claim 1 wherein said substrate comprises one or more components selected from the group consisting of silicon, aluminum, polymeric resins, silicon dioxide, doped silicon dioxide, silicon nitride, tantalum, copper, polysilicon, ceramics, aluminum/copper mixtures, gallium arsenide and Group III/V compounds. ### Claim 5 (depends on 1) The method of claim 1 wherein the exposure step is conducted with actinic, x-ray or ion beam radiation. ### Claim 6 (depends on 1) The method of claim 1 wherein the exposure step is conducted with ultraviolet radiation having a wavelength of about 365 nm. ### Claim 7 (depends on 1) The method of claim 1 wherein the removing step is conducted with an aqueous alkaline developer selected from sodium hydroxide, potassium hydroxide or tetramethyl ammonium hydroxide. ### Claim 8 (depends on 1) The method of claim 1 wherein the composition further comprises one or more components selected from the group consisting of non-aromatic colorants, dyes, anti-striation agents, leveling agents, plasticizers, adhesion promoters, speed enhancers, and surfactants. ### Claim 9 (depends on 1) The method of claim 1 wherein (a) is present in an amount of from about 1 to about 35 weight percent and (b) is present in an amount of from about 65 to about 99 weight percent, based on the non-solvent parts of the composition. ### Claim 10 (depends on 1) The method of claim 1 wherein the solvent comprises one or more solvents. ### Claim 11 (depends on 1) The method of claim 1 wherein the solvent comprises propylene glycol monomethyl ether acetate. ### Claim 12 (depends on 1) The method of claim 1 wherein the solvent comprises ethyl-3-ethoxy propionate. ### Claim 13 (depends on 1) The method of claim 1 wherein the solvent comprises ethyl lactate. ### Claim 14 (depends on 1) The method of claim 1 wherein the benzolactone ring compound comprises either phenolphthalein or cresolphthalein as the backbone.