Abstract: The present invention relates to a positive-working photoresist composition comprising at least one of the 1,2-naphthoquinonediazido-5- sulfonic acid ester of a polyhydroxy compound represented by formula (1) and the 1,2-naphthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound represented by formula (1): ##STR1## wherein R represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, or an alkenyl group; and R.sub.1 to R.sub.15, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a substituted or unsubstituted cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.15 is a substituted or unsubstituted cycloalkyl group.

Abstract: A positive resist composition comprising an alkali-soluble resin and a light-sensitive quinonediazide material containing a quinonediazidesulfonic acid ester of at least one phenol compound represented by the following general formulas: ##STR1## wherein R.sub.1 represents hydrogen, halogen, or the like; R.sub.3 represents alkyl or phenyl; x represents 1-3; Q.sub.1 to Q.sub.12 represent hydrogen, alkyl or phenyl; and Z.sub.1 to Z.sub.5 represent the groups of the following formulas: ##STR2## wherein R.sub.2 is hydrogen, halogen or the like; R.sub.3 is as defined above; y is 1-3; and p is 0 or 1. This positive resist composition is excellent in the balance between properties such as resolution, profile, depth of focus, etc.

Abstract: Proposed is a positive-working photosensitive resin composition suitable as a photoresist in the photolithographic patterning work for the manufacture of, for example, semiconductor devices having excellent storage stability and capable of giving a patterned resist layer having excellent contrast of the images, orthogonality of the cross sectional profile of line patterns and heat resistance along with a satisfactorily high photosensitivity and large focusing latitude. The composition comprises, in admixture with an alkali-soluble novolac resin as a film-forming agent, a photosensitizing agent which is an esterification product of a specific tris(hydroxyphenyl) methane compound of which two of the hydroxyphenyl groups each have a cyclohexyl group bonded thereto at a specified position with at least one naphthoquinone-1,2-diazide sulfonyl group as the esterifying group.

Abstract: Positive photoresists formulations for producing positive photoresist images having improved thermal stability yet which allow a wide variation in resin to photoactive sensitizer compound without significant changes in photospeed, thermal behavior, contrast or resolution and with virtually no less in unexposed areas of the photoresist and without significant outgassing or popping are provided by employing novel 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone with a novel isomeric distribution of esters. The novel isomeric distribution of 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone is characterized by two major isomers, together comprising at least about 70% by weight of the photoactive compound, and wherein the least polar isomer comprises only about 40%.

Abstract: A novel alkali-developable photosensitive resin composition, which is suitable for use as a photoresist composition for fine patterning in the manufacture of various electronic devices, is proposed. The photosensitive resin composition comprises, as the essential ingredients, (a) an alkali-soluble novolac resin as the film-forming ingredient and (b) a very specific compound which is a 1,2-quinone diazide sulfonic acid ester of a condensation product having a weight-average molecular weight of 400 to 2000 obtained by the condensation reaction between phenol and a hydroxybenzaldehyde in the presence of an acidic catalyst as the photosensitizing agent. By virtue of the formulation with this specific photosensitizer, the resist layer formed from the inventive composition has a greatly increased focusing latitude in addition to the excellent sensitivity, resolution and heat resistance.

Abstract: Positive photoresist compositions and methods using the photoresist compositions for making submicron patterns in the production of semiconductor devices are disclosed. The photoresists contain sensitizers that are mixed naphthoquinonediazide 4- and 5- sulfonic acid esters of bis and tris(mono, di and trihydroxyphenyl) alkanes.

Abstract: The photosensitive resin composition of the present invention comprises an admixture of 5 to 100 weight parts of a photosensitive material having the following general formula (A) and 100 weight parts of an alkali-soluble resin:General formula (A) ##STR1## where R.sub.1 to R.sub.8 each independently represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an aralkyl group, an aryl group, an amino group, a monoalkylamino group, a dialkylamino group, an acylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfamoyl group, an arylsulfamoyl group, a carboxyl group, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or --OD, --N(R)--D (where R represents a hydrogen atom or an alkyl group, and D represents a 1,2-napthoquinoediazide-5-sulfonyl group or a 1,2-napthoquinoediazide-4-sulfonyl group), and at least one of R.sub.1 to R.sub.8 represents --OD or --N(R)--D; R.sub.9 to R.sub.

Abstract: Disclosed is a novel positive type photoresist composition comprising a 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic ester of a member selected from the group consisting of the polyhydroxy compounds represented by the following formula (I), (II) or (III) and an alkali-soluble resin: ##STR1## wherein the variables of Formula I are defined in the specification; ##STR2## wherein the variables of Formula II are defined in the specification; ##STR3## wherein the variables of Formula III are defined in the specification.

Abstract: A positive working deep UV sensitive photoresist which provides improved critical dimension stability during prolonged periods of post exposure delay before baking comprises an acid stable polymer which is insoluble in water but normally soluble in an aqueous alkaline medium, a photo acid generator exemplified by the tri-(2,1,4-diazonaphthoquinonesulfonate) ester of 3,5-dinitro-2,6-dimethylol para cresol, and a mixed carbonate ester of tertiary butyl alcohol and a polyhydric phenol which is an acid labile compound which inhibits the dissolution of the normally soluble polymer in said alkaline medium.

Abstract: A 2-diazo-1,2-quinone compound having a substituent group containing an alkyl group which is substituted by at least one fluorine atom is described. This compound has a capacity to change its polarity when exposed to light. The invention also provides an image forming material in which the invention compound is added to at least one of laminated layers. When these laminated layers are exposed to light, the adhesiveness of the compound-containing layer to its adjoining layer is reduced effectively due to the polarity-changing ability of the compound, thus making the easy delamination of the layers possible. This compound is applicable to many instances in which image receiving sheets are used, such as the formation of a multi-color image by a transfer method (a color proof, for example) and the preparation of a printing plate of the delamination development type.

Abstract: A new photoacid generator having the formula ##STR1## wherein R=hydrogen, hydroxyl, or the --O--S(.dbd.O).sub.2 --Q moiety;R.sup.1 =CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.2 =CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.3 =lower alkyl or hydrogen;R.sup.4 =hydrogen, --CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.5 =hydrogen, --CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ; andQ is a diazonaphthoquinone moiety; with the proviso that R.sup.3 is lower alkyl when R.sup.2 and R.sup.4 are NO.sub.2, and with the proviso that R.sup.1 .noteq.R.sup.2 and R.sup.4 .noteq.R.sup.5.exhibits unprecedented sensitivity to actinic radiation. This compound is photochemically transformed from a non-acidic entity to photoproducts which contain both sulfonic and carboxylic acid functuional groups. The acid generator is effective with polymers having acid labile groups, converting them into alkaline-soluble polymers, and with polymers which do not have such acid labile groups.

Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and a photosensitive agent, characterized in that the positive resist composition contains, as the photosensitive agent, the quinonediazide sulfonate of at least one of phenolic compounds represented by the following general formulae (I) and (II): ##STR1## wherein R.sub.1 through R.sub.4 mean individually a hydrogen or halogen atom, a hyaroxyl group, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.5 denotes a hydrogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or an aryl group with the proviso that the number of hydroxyl groups is 3 or 4; and ##STR2## wherein R.sub.6 through R.sub.9 mean individually a hydrogen or halogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.

Abstract: A radiation-sensitive polymer and a mixture containing this radiation-sensitive polymer as a binder are disclosed. A process for the preparation of the radiation-sensitive polymer binder and a positive-working radiation-sensitive recording material which is prepared using the radiation-sensitive mixture are also disclosed.

Abstract: Positive photoresists formulations for producing positive photoresist images having improved thermal stability yet which allow a wide variation in resin to photoactive sensitizer compound without significant changes in photospeed, thermal behavior, contrast or resolution and with virtually no less in unexposed areas of the photoresist and without significant outgassing or popping are provided by employing novel 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone with a novel isomeric distribution of esters. The novel isomeric distribution of 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone is characterized by two major isomers, together comprising at least about 70% by weight of the photoactive compound, and wherein the least polar isomer comprises only about 40%.

Abstract: A positive photoresist composition is provided, which comprises an alkali-soluble novolak resin and at least one light-sensitive material represented by formula (III), ##STR1## wherein R.sub.27 and R.sub.28 may be the same or different and which represents --OH, ##STR2## R.sub.29 and R.sub.33 may be the same or different and each represents --H, --OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted acyloxy group, a halogen, a nitro group, a cyano group, ##STR3## R.sub.34 to R.sub.

Abstract: A radiation sensitive compound prepared by reacting a phenol compound with a quinone diazide sulfonyl halide in a mixture of a solvent having a relative dielectric constant of not larger than 10 and a solvent having a relative dielectric constant of at least 15, which compound is less colored and gives a positive resist composition having a good resolution.

Abstract: A positive resist composition which comprises an alkali-soluble resin and, as a sensitizer, a quinone diazide sulfonic acid ester of a phenol compound of the formula: ##STR1## wherein Y.sub.1, Y.sub.2, Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are independently a hydrogen atom, a hydroxyl group, a C.sub.1 -C.sub.4 alkyl group which may be substituted with a halogen atom, provided that at least one of Y.sub.1 and Y.sub.2 is a hydroxyl group, and at least two of Z.sub.1 to Z.sub.7 are hydroxyl groups, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.1 -C.sub.4 alkenyl group, a cycloalkyl group or an aryl group, which composition has a high .gamma.-value.

Abstract: A radiation sensitive mixture comprising an alkali-soluble binder resin and at least one photoactive compound comprising a compound of formula (I): ##STR1## wherein each R is individually selected from hydrogen and a lower alkyl group having 1 to 4 carbon atoms; n is either 0, 1, or 2; and D is selected from the group consisting of hydrogen or o-naphthoquinone diazide sulfonyl group; with the proviso that at least two D's are o-naphthoquinone diazide sulfonyl groups, and wherein the amount of said binder resin is about 70 to 95% by weight and the amount of photoactive compound being from about 5 to about 30% be weight, based on the total solids content of said content of said raditional-sensitive mixture.

Abstract: The invention relates to a radiation-sensitive ester which is the condensation product of (a) a compound containing 2 to 6 aromatic hydroxyl groups, (b) a ring-substituted (o-naphthoquinone 2-diazide)-4-sulfonic acid (compound D.sub.1 and (c) an (o-naphthoquinone 2-diazide)-4- or -5-sulfonic acid which is not further substituted (compound D.sub.2) and/or a non-radiation-sensitive organic acid (compound D.sub.0), where the (b):(c) molar ratio is between 0.1:1 and 39:1.

Abstract: A photosensitizer composition comprising a diazo fluorinated ester containing the hexafluoroisopropylidene group, said photosensitizer selected from hexafluoro-bis-phenols having the following formula: ##STR1## where R is selected from hydrogen, methyl, ethyl and phenyl; and bis-hexafluoroethers having the following formula: ##STR2## wherein R' is selected from hydrogen, methyl, ethyl and phenyl.

Abstract: A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups,X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.

Abstract: Photosensitive compounds having preferably a functional group such as --SO.sub.2 Cl, --SO.sub.3 H, --SO.sub.3 R, ##STR1## (R, R', R" being alkyl) on a terminal benzene or naphthalene ring connected via a methylene group and ##STR2## moiety are improved in sensitivity to light and thermal stability, and thus useful in a photo resist.

Abstract: A positive type photoresist composition which comprises an alkali soluble novolak resin and at least one light-sensitive material represented by the following general formulae (I) to (IV) to provide a resist pattern with high resolution, high reproduction fidelity, desirable sectional shape, wide latitude of development, high heat resistance and high storage stability: ##STR1## (wherein X represents --CO--, or --SO.sub.2 --; p represents an integer from 2 to 4; R's may be the same or different, each being --H, --OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted acyloxy group, ##STR2## provided that R always contains at least one of ##STR3## ; R.sub.

Abstract: A radiation-sensitive resin composition containing an alkali-soluble resin, comprising a polyhydroxy compound having the following formula: ##STR1## or a quinonediazidesulfonate of the polyhydroxy compound. The radiation-sensitive resin composition is suitable for use as a positive type photoresist which has such excellent developability as to inhibit effectively the generation of scum in the formation of a photoresist pattern, has high sensitivity and is excellent in heat resistance and remained thickness ratio upon development.

Abstract: A quinone diazide of formula (I) or formula (II):(S)l--(L.sup.1)m=-(Q).sub.n (I)--(L.sup.2 (-S))o-(L.sup.3 (--Q))p- (II)wherein S is a light absorbing portion having an absorption coefficient of greater than 1000 in wavelengths longer than 360 nm; Q is a quinone diazide residue; L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and Q, provided, however, that L.sup.1, L.sup.2 and L.sup.3 do not conjugate S and Q; l, m, n, o and p are integers; andwherein the emission intensity of the compound of formulas (I) and (II) is smaller than the emission intensity of the chromophoric group alone. Also disclosed is a light sensitive composition comprising an alkali soluble resin and the above quinone diazide compound. The quinone diazide compound of the present invention have spectral sensitization with respect to visible light and are useful in visible light projection plates and as visible laser sensing materials.

Abstract: Disclosed is a photosensitive quinone diazide compound for the preparation of a two component positive working photosensitive electrodeposition composition. As the photosensitive group is grafted on a polyurethane, the photosensitive compound thus synthesized has good flexibility and good compatability with acrylic resin. The electrodeposition composition also has good adhesion to the metal base plate when it is coated thereon by electrodeposition means.

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 the benzolactone ring compound 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.

Abstract: A process of developing an image-wise exposed photoresist-coated substrate comprising: coating a substrate with a positive working photoresist comprising an admixture of an alkali soluble binder resin and photoactive formula (V): ##STR1## wherein R.sub.2 is selected from the group consisting of an OD group, a halide group, a lower alkyl group having 1 or 4 carbon atoms and a lower alkoxy group having 1 to 4 carbon atoms, and D is selected from the group consisting of o-naphthoquinone diazide sulfonyl group and hydrogen; with the proviso that at least four D's are o-naphthoquinone diazide sulfonyl groups; subjecting the coating on the substrate to an image-wise exposure of radiation; and subjecting the image-wise coated substrate to a developing solution to remove the exposed areas of the radiation-exposed coating, leaving a positive image pattern.

Abstract: Positive photoresists formulations for producing positive photoresist images having improved thermal stability yet which allow a wide variation in resin to photoactive sensitizer compound without significant changes in photospeed, thermal behavior, contrast or resolution and with virtually no less in unexposed areas of the photoresist and without significant outgassing or popping are provided by employing novel 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone with a novel isomeric distribution of esters. The novel isomeric distribution of 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone is characterized by two major isomers, together comprising at least about 70% by weight of the photoactive compound, and wherein the least polar isomer comprises only about 40%.

Abstract: A trihydroxybenzophenone compound of the formula (I): ##STR1## wherein R.sub.1 is selected from the group consisting of hydroxyl group, halide group, a lower alkyl group having 1 to 4 carbon atoms, and a lower alkoxy group having 1 to 4 carbon atoms.

Abstract: A process for preparing 7-hydroxy-1,2-naphthoquinone-2-diazide-4-sulfonic acid or salts thereof, of the general formula Z ##STR1## is disclosed in which X=hydrogen, a metal or an ammonium group, preferably an alkali metal or alkaline earth metal, especially sodium or potassium and the ammonium group.The compounds can be used as much or as intermediates or starting materials for the production of light-sensitive compounds and radiation-sensitive mixtures and materials.

Abstract: Polyfunctional compounds containing .alpha.-diazo-.beta.-keto ester units and sulfonate units are disclosed. The polyfunctional compounds have high sensitivity in the deep UV and high thermal stability. Processes for producing the compounds are disclosed. A preferred process first synthesizes .beta.-ketoester/sulfonate precursors and then uses diazo transfer to convert the precursors into the novel compounds. Radiation-sensitive mixtures containing the compounds are also disclosed.

Abstract: A radiation sensitive oligomeric compound is described as the photoactive component with a base soluble phenolic matrix resin to provide improved photo-resist composition having high light-sensitivity, high resolution, excellent developer resistance and excellent resistance to thermal flow.

Abstract: A positive-working photoresist composition is disclosed, which comprises (1) a light-sensitive material obtained by reacting a polyhydroxy compound containing at least one group represented by the following general formula (I) per molecule with at least one of 1,2-naphthoquinonediazido-5-sulfonyl chloride and 1,2-naphthoquinonediazido-4-sulfonyl chloride, and (2) an alkali-soluble novolak resin: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a C.sub.1 -C.sub.4 straight or branched alkyl or alkoxy group, provided that R.sub.1 and R.sub.2 do not represent hydrogen atoms at the same time; and X represents a divalent organic group.

Abstract: The invention relates to new mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitizer compositions exhibit excellent solution stability and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.

Abstract: A positive type photoresist composition comprising at least one light-sensitive material, as defined herein, and an alkali-soluble novolak resin, has a high resolving power, particularly when used in semiconductor devices, accurately reproduces mask dimensions over a wide photomask line width range, from a resist pattern in a cross-sectional form having a high aspect ratio in a pattern having a line width of no greater than 1 .mu.m, has a wide developing latitude and excellent heat resistance.

Abstract: A photoactive compound having formula (I): ##STR1## wherein R is selected from the group consisting of hydrogen or a lower alkyl group having 1-4 carbon atoms and each D is individually selected from the group consisting of a hydrogen or photoactive o-quinonediazide sulfonyl group; subject to the proviso that at least two of the four D's in formula (I) are photoactive o-naphthoquinonediazide sulfonyl moieties.

Abstract: The invention relates to novel radiation-sensitive compounds which are esters or amides of a 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid of the general formula ##STR1## in which R.sub.1 and R.sub.2 are identical or different and denote hydrogen, an alkyl group, an alkyl ether group or an alkyl thioether group whose carbon chains may be interrupted by ether oxygen atoms, an acylamino group, carboxylic acid ester group, sulfonic acid ester group or sulfonamide group,R.sub.1 and R.sub.2 not being hydrogen at the same time.The compounds are used as radiation-sensitive components in radiation-sensitive mixtures with which corresponding copying materials can be produced. The compounds have an absorption which is directed towards longer wavelengths matching the emission range of commercially available radiation sources. They also make it possible, in a reliable and practical manner, to carry out negativeworking image reversal processes.

Abstract: A light-sensitive compound is described, containing a quinonediazido group and an alkylimidazole group in the same molecule and which is solubilizable in an aqueous alkali solution upon irradiation with light, and a method of forming a photoresist using the light-sensitive compound. The compound is useful, for example, in production of print substrates and in chemical milling.

Abstract: Compounds of the general formulaR--N.dbd.NX (I)or N-oxides thereof, where R represents on amidophenyl group, and X represents a cyano group, a group --COOH or a salt, ester or amino derivative thereof; are fungicidal.

Abstract: The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I ##STR1## which are substituted in at least one of the positions 5, 6, 7 or 8 by R=halogen, alkoxy groups or alkoxycarbonyl groups and in which X denotes an aryl group. The process comprises steps in whicha) suitably substituted .beta.-naphthol is nitrosated,b) sulfonation with alkali hydrogensulfite and acid in position 4 and reduction are carried out,c) the naphthalenesulfonic acid derivative is oxidized,d) the 1,2-naphthoquinone-4-sulfonic acid formed is reacted with toluenesulfonohydrazide in an organic solvent at temperatures from 20.degree. to 100.degree. C.,e) the naphthoquinonediazide compound is converted with chlorosulfonic acid or chlorosulfonic acid/thionyl chloride into the sulfonyl chloride, and f) the sulfonyl chloride is condensed with a phenolic component, a purification of the respective intermediate product by reprecipitation or recrystallization being unnecessary.

Abstract: Substituted 1,2-naphthoquinone-2-diazide-4-sulfonic acids are disclosed having the general formula A ##STR1## in which R is an alkyl, epoxyalklyl, alkylcarbonyl or alkylsulfonyl group, the carbon chains of which may be interrupted by oxygen atoms, or a substituted or unsubstituted aralkyl, arylcarbonyl or arylsulfonyl group andX is hydrogen, a metal or an ammonium group.A process for the preparation of the compounds is also disclosed. The compounds can be used as such, or preferably after condensation of their sulfonic acid chlorides with aromatic hydroxy compounds or amines to give the corresponding esters or amides, as light-sensitive compounds in radiation-sensitive mixtures or materials.

Abstract: The invention relates to desensitized quinone diazide compounds for use as photoactive components in radiation-sensitive compositions, such as, especially, photoresists, which compounds contain microcrystalline cellulose as desensitizing agent.

Abstract: A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I): ##STR1## wherein Y.sub.1 and Y.sub.2 are each a hydrogen atom, an alkyl group or a hydroxyl group, provided that at least one of Y.sub.1 and Y.sub.2 is a hydroxyl group; Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are the same or different and each a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, an aryl group or halogen atom, provided that at least two of Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are hydroxyl groups; R.sub.1, R.sub.2 and R.sub.3 are the same or different and each a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group provides a positive resist composition having a high .gamma.-value.

Abstract: The invention relates to new mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitiizer compositions exhibit excellent solution stability and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.

Abstract: A trinuclear novolak oligomer of the formula (I): ##STR1## wherein each X is selected from the group consisting of hydroxyl group and halide group and Y is selected from the group consisting of a lower alkyl group having 1-4 carbon atoms and halogen atom.

Abstract: A trinuclear novolak oligomer of the formula (I): ##STR1## wherein each X is selected from the group consisting of hydroxyl group and halide group and Y is selected from the group consisting of a lower alkyl group having 1-4 carbon atoms and halogen atom.

Abstract: A process for the preparation of aryl-diazide-sulfonic acids by a series of sequential in-situ process steps. The process comprises the nitrosation of a hydroxyarylsulfonic acid; conversion of the nitroso-derivative to a sulfamate which is then diazotized to the diazide. Temperature and pH are maintained in predetermined ranges to maintain the reaction products in solution without the formation side-products or the need to isolate intermediates.The process of the invention is particularly useful in the preparation of light-sensitive materials such as naphthoquinonediazide sulfonic acids which are used in the preparation of photoresist compositions. The invention provides a high purity product at a high material efficiency, high equipment utilization, low effluent discharge, and reduced cost.

Abstract: The invention relates to mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitizer compositions exhibit excellent solution stablity and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.

Abstract: Disclosed are substituted derivatives of 5-diazobarbituric acid selected from those having the formulas: ##STR1## wherein R.sub.1 and R.sub.2 are substituents selected from the group consisting of C.sub.3 to C.sub.12 alkyl, cyclohexyl, benzyl and C.sub.2 to C.sub.6 aralkyl groups, wherein R.sub.3 and R.sub.4 are substituents selected from the group consisting of C.sub.1 to C.sub.12 alkyl, cyclohexyl, benzyl or other C.sub.2 to C.sub.6 aralkyl groups and R.sub.5 is selected from the group consisting of .alpha.,.omega.-disubstituted C.sub.2 to C.sub.12 alkyl, methylene dicyclohexyl, or C.sub.1 to C.sub.6 dialkylphenylene.These compounds provide DUV response with an absorption maximum near 260 nm. The substituents are chosen to be nonabsorbing alkyl groups that allow efficient photobleaching of the sensitizer during exposure.The sensitizers of the present invention are designed to function in the DUV region and are useful in the manufacture of semi-conductor devices.