Abstract: The present invention includes polymers and photoresist compositions that comprise the polymers as a resin binder component. Photoresists of the invention include chemically-amplified positive-acting resists that can be effectively imaged at short wavelengths such as sub-200 nm, particularly 157 nm. Particular polymers and photoresists of the invention include at least one electronegative group that reduces 157 nm absorbance of a wide spectrum of organic groups including aromatic groups such as phenolic moieties.

Abstract: The present invention includes polymers and photoresist compositions that comprise the polymers as a resin binder component. Photoresists of the invention contain a polymer that has fluorinated phenolic units and photoacid-labile groups. Resists of the invention can be effectively imaged at short wavelengths such as sub-200 nm, particularly 157 nm.

Abstract: Disclosed are new photoresist compositions including polymeric particles as binders and a photoactive component. Also disclosed are methods of forming relief images using these photoresist compositions.

Abstract: The present invention includes polymers and photoresist compositions that comprise the polymers as a resin binder component. Photoresists of the invention include chemically-amplified positive-acting resists that can be effectively imaged at short wavelengths such as sub-300 nm, particularly 157 nm. Preferred polymers and photoresists include acid labile acetal or ketal groups that help degrade the polymer by hydrolysis. More preferred polymers include at least one electronegative group that reduces or avoids 157 nm absorbance of a wide spectrum of organic groups including aromatic groups such as phenolic moieties.

Abstract: Disclosed are polymers containing polymerized units one or more cyclic olefin monomers having one or more pendant cyclic electron withdrawing groups, methods of preparing such polymers, photoresist compositions including such polymers as resin binders and methods of forming relief images using photoresist compositions.

Abstract: The invention is for a process of removing acid salt contaminants from a resin solution. The process comprises providing an organic solution of a phenolic resin having a portion of its phenolic hydroxyl groups condensed with an acid halide in the presence of a base catalyst. The organic solutions is then contacted with a strong acid cation exchange resin and a base anion exchange resin for a time sufficient to remove essentially all of said acid salt contaminants. Acid salt contamination is reduced to a level below normal detection limits.

Abstract: An unsymetrical photoactive compound having the formula ##STR1## where Z is hydrogen, a hydrocarbon having from 1 to 8 carbon atoms, or halogen; D is hydrogen or diazo-oxo-naphthalene-sulfonyl; n is equal to 1 to 4; R.sub.1, R.sub.5 and R.sub.6 are independently a hydrocarbon or halogen; R.sub.2 is the same as R.sub.1 or hydrogen; each R.sub.3 is the same as R.sub.2, hydroxyl or --OD; and each R.sub.4 is the same as R.sub.2 or another substituent provided that at least one R.sub.2, or one or both R.sub.4 is other than hydrogen, at least 2 Ds are diazo-oxo-sulfonyl group and at least 50 mole percent of the mixture conforms to the formula where n equals 1. The compounds of the invention are suitable for formation of storage stable photoresist compositions.

Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.

Abstract: The invention is directed to purification of phenolic resins and to a process for preparing an organic photoresist coating composition. The process comprises reacting one or more phenols to form a crude phenolic resin. The crude phenolic resin formed is then separated from its reaction mixture and dissolved in an aqueous insoluble organic solvent in an organic solvent that is a solvent for the photoresist coating composition. The solution so formed is then mixed with an aqueous phase to extract water soluble impurities from the resin solution into the aqueous phase. Finally, the purified resin solution is further diluted with additional photoresist solvent.

Abstract: This invention relates to alternating and block copolymer resins of uniform and controlled chain length and methods for preparing the same. The alternating copolymer resins are formed from the reaction of a bisoxymethylphenol, a reactive phenolic compound and a monooxymethylphenol. The alternating copolymer may then be further reacted with a second reactive compound in the presence of an aldehyde to form the substantially blocked copolymer. The resins of the invention are characterized by a low molecular weight distribution. The resins are useful for the formulation of high resolution photoresist materials.

Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound. The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.

Abstract: The invention is directed to purification of phenolic resins and to a process for preparing an organic photoresist coating composition. The process comprises reacting one or more phenols to form a crude phenolic resin. The crude phenolic resin formed is then separated from its reaction mixture and dissolved in an aqueous insoluble organic solvent in an organic solvent that is a solvent for the photoresist coating composition. The solution so formed is then mixed with an aqueous phase to extract water soluble impurities from the resin solution into the aqueous phase. Finally, the purified resin solution is further diluted with additional photoresist solvent.

Abstract: The invention relates to a positive-acting photoresist composition containing a mixture of photoactive compounds. One component of the mixture is the esterification product of an o-quinonediazide sulfonyl compound with a phenolic resin. Another component of the mixture is the esterification product of an o-quinonediazide sulfonyl compound with a low molecular weight phenol having from one to three aryl groups and from one to three hydroxyl groups. A third photoactive component which may be present in the formulation is the esterification product of an o-quinonediazide sulfonyl compound with a relative high molecular weight, polyhydric, polynuclear phenol.

Abstract: The invention is for a process of removal of dissolved cation contaminants from a resin solution. The process of the invention involves providing a chelating ion exchange resin modified by treatment with an acid and contact of said solution with said modified exchange resin for a time sufficient to remove ionic metal impurities. The invention is useful for removal of ionic contaminants from resin solutions used in the preparation of photoresists.

Abstract: A new photoactive compound for use in the formulation of a photoresist comprises a bisphenol compound having an alkyl linkage substituted with a heterocyclic group. The new photoactive compound may be admixed with an alkali soluble resin to formulate a photoresist composition. The new photoactive compounds exhibit enhanced long term solubility in conventional photoresist solvents.

Abstract: A resin suitable for use as a photoresist that is the esterification product of an o-quinonediazide compound and an aromatic novolak resin. The aromatic novolak resin may be the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde. The aromatic resin may be chain extended by further reaction with an additional aldehyde. The resin has a maximum of 20 percent of its phenolic hydroxyl groups esterified with the o-quinonediazide sulfonate compound.

Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.

Abstract: A photoresist that is a mixture of the esterification product of an o-quinonediazide compound and a novolak resin and a high molecular weight phenol having from 2 to 5 phenolic groups and at least 4 diazo naphthoquinone groups. The extent of esterification of the novolak resin is up to 20 percent of the hydroxyl groups and the degree of esterification of the phenol is at least 50 percent of the phenolic hydroxyl groups. The preferred novolak resins are the aromatic novolak resin that are the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde, each alone or in the presence of a reactive phenol.

Abstract: A new photoactive compound for use in the formulation of a photoresist comprises a bisphenol compound having an alkyl linkage substituted with a heterocyclic group. The new photoactive compound may be admixed with an alkali soluble resin to formulate a photoresist composition. The new photoactive compounds exhibit enhanced long term solubility in conventional photoresist solvents.

Abstract: A photoresist comprising a light sensitive component and an alternating copolymer resin formed by condensing a preformed bishydroxymethylated compound and a reactive phenol, in the absence of an aldehyde. Additional useful resins may be formed by further reacting the alternating copolymer with a second reactive phenol in the presence of an aldehyde to form substantially block copolymers. The use of these resins in photoresist formulations leads to improved thermal properties, etch resistance and photospeed.