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: Disclosed is a pattern forming method using pattern forming material which is reactive to a light of 249 nm or so such as DUV light or excimer laser light and applicable to manufacture of semiconductors. The material used in this method includes resin which includes a bonding unit of ##STR1## and has low absorption near 249 nm after light exposure, and is soluble in a solvent which dissolves the resin. By this method, a fine pattern of high contrast can be obtained.

Abstract: A light-sensitive composition comprises at least one polyuretane resin having repeating unit represented by formula (I) and/or repeating unit represented by formula (II) and which is insoluble in water and soluble in aqueous alkaline solution; and at least one positive-working light-sensitive compound: ##STR1## wherein R.sub.1 represents a bivalent aliphatic or aromatic hydrocarbon which may have a substituent; R.sub.2 represents hydrogen atom or an alkyl, an aralkyl, an aryl, an alkoxy or an aryloxy group which may be substituted with a substituent; R.sub.3, R.sub.4 and R.sub.5 may be the same or different and independently represent a single bond or a bivalent aliphatic or aromatic hydrocarbon group which may have a substituent and Ar represents a trivalent aromatic hydrocarbon group which may have a substituent.

Abstract: The photosensitive composition, which is suitable as a photoresist material in fine patterning works for the manufacture of semiconductor devices, contains, as a photoextinctive agent, a combination of an alkali-insoluble dye and an alkali-soluble dye each having absorptivity of light in the wavelength region from 230 to 500 nm in a specified amount and in a specified ratio between them. By virtue of the formulation of combined dyes, the undesirable phenomenon of halation by the underlying aluminum coating layer on the substrate surface is greatly decreased so that patterned resist layer obtained with the composition is a high-fidelity reproduction of the original pattern even in a submicron range of fineness with good rectangularity of the cross sectional form of the patterned lines.

Abstract: The dissolution rate in alkaline developer solutions of image-wise exposed photoresist systems based on diazoquinone sensitized polyamic acid is reduced to prepare relief images of fine line resolution by reducing the acidity of the polyamic acid prior to exposure.

Abstract: A process for the preparation of an o-naphthoquinonediazide sulfonic acid ester is disclosed. Esterification of an o-naphthoquinonediazide sulfonic acid halide with a mono- or polyvalent phenolic compound in a solvent is performed in the presence of ammonia, of ammonium salts of weak acids or of aliphatic derivatives of ammonia having 1 to 3 carbon atoms, at a pH within the range from about 1.5 to about 8.5 and a temperature within the range from about 15.degree. C. to about 40.degree. C. The esters of o-naphthoquinonediazide sulfonic acid which are obtained by this process contain only small amounts of metal ions and can be used in photosensitive mixtures satisfying high requirements of the microelectronics industry.

Abstract: Photoresist compositions which operate positively and contain at least one ocmpound of the formula I ##STR1## in which X is --C.sub.n H.sub.2n --, --O--, --S-- or --C(O)--, n being a number from 1 to 6. These compositions are particularly suitable for use as positively-operating copying lacquers.

Abstract: A process for the formation of an image comprises(i) applying to a substrate a layer of a liquid composition comprising(A) a residue which is cationically polymerizable or polymerizable by means of free radicals,(B) a radiation-activated polymerization initiator for (A) and(C) a radiation-solubilizable residue,(ii) subjecting the composition to radiation having a wavelength at which (B) is activated but at which (C) is not substantially activated, optionally followed by heating, thereby polymerizing (A) such that the layer of liquid composition is solidified,(iii) subjecting the solidified layer in a predetermined pattern to radiation having a wavelength which is different from that of the radiation used in stage (ii) and at which the residue (C) is activated, such that the solidified layer is rendered more soluble in a developer in exposed areas than in unexposed areas, and(iv) removing the exposed areas by treatment with a developer.

Abstract: A positive type photosensitive composition capable of improving the drawback in the conventional positive type photosensitive resin composition, improving adhesion between the positive type photoresist and the substrate and improving developability is provided by incorporating benzotriazole carboxylic acids in the positive type photoresist.

Abstract: A light-sensitive composition comprising a phenolic resol wherein the ratio of the number of dibenzylic ether linkages to the total number of dibenzylic ether, methylene and methylol linkages linked to phenolic nucleus is 15 mol. % or more and which is obtained by a reaction between a phenol of the formul (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent hydrogen, halogen, hydroxyl, nitro, alkyl, alkoxy, phenyl, or substituted phenyl, and an aldehyde or ketone.A light-sensitive composition comprising a condensate of the phenolic resol and an o-quinone diazido sulfonylhalide.A light-sensitive material comprising the above-mentioned composition.A method for making a planographic printing plate from the light-sensitive material, characterized in that burning-in process is carried out at a lower temperature or a shortened time.

Abstract: Light sensitive compositions are disclosed which comprise 2-halomethyl-1,3,4,-oxadiazole compounds having a heterocyclic radical in the fifth position containing at least one element selected from the group consisting of oxygen, nitrogen, sulphur, and selenium directly or through a vinyl radical.

Abstract: An electrodepositable photosensitive resin which is a phenolic novolak resin having(i) at least part of the phenolic hydroxyl groups thereof replaced by a quinone diazide sulphonyloxy group, and(ii) at least part of the aromatic rings thereof substituted in a position ortho and/or para to a phenolic hydroxyl group or quinone diazide sulphonyloxy group by a group of formula --CH(R.sup.1)R.sup.2 whereR.sup.1 represents a hydrogen atom, or an alkyl, aryl or carboxylic acid group, andR.sup.2 represents a sulphonic acid group --SO.sub.3 H or a group of formula --A--R.sup.3 --X,R.sup.3 represents an aliphatic, aromatic or araliphatic divalent group which may be substituted by a carboxlic, sulphonic or phosphonic acid group,A represents a sulphur atom or a group of formula --N(R.sup.4)--, where R.sup.4 represents a hydrogen atom or an alkyl group which may be substituted by a carboxylic acid group or by an optionally etherified hydroxyl group, or R.sup.3 and R.sup.

Abstract: Compounds of the general formula (I) or (II) ##STR1## in which R is 1,2-naphthoquinone-2-diazide-4- or -5-sulfonyl and X is a straight-chain or branched C.sub.1 -C.sub.12 -alkylene group, which is unsubstituted or mono- or disubstituted by OH group or is --CH.dbd.CH--, are suitable as the light-sensitive component in photoresist materials. Both positive and negative images can be prepared with light-sensitive mixtures containing these compounds and a binder.

Abstract: The photosensitive composite of the present invention is obtained by including a nonsubstitutional or substitutional benzyl radical in the phenol side chain of polyvinylphenol. The photosensitive composites have not only excellent heat resistivity, RIE resistivity, and resolving power but also have a wide tolerance for the variations in the development temperature and developer concentration at the time of development. Therefore, it is possible to obtain resist patterns with fine structure.

Abstract: A photosolubilizable composition containing (a) a first compound capable of producing an acid by irradiation with actinic rays and (b) a high molecular weight compound, whose solubility in a developing solution is increased by the action of an acid, and a photosolubilizable composition containing (c) a high molecular weight compound whose solubility in a developing solution is increased by irradiation with actinic radiation, are disclosed. These compositions exhibit high photosensitivity, broad development latitude, and high stability with time.

Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.

Abstract: The present invention is concerned with methods of converting a single resist layer into a multilayered resist.The upper portion of the single resist layer can be converted into a dry-etch resistant form. The conversion can be a blanket conversion of the upper portion of the resist layer or can be a patterned conversion of areas within the upper portion of the layer. A patternwise-converted resist can be oxygen plasma developed.The upper portion of the single resist layer can be patternwise converted into a chemically different composition or structure having altered absorptivity toward radiation. The difference in radiation absorptivity within the patterned upper portion of the resist enables subsequent use of blanket irradiation of the resist surface to create differences in chemical solubility between areas having the altered absorptivity toward radiation and non-altered areas. The difference in chemical solubility enables wet development of the patterned resist.

Abstract: A method of forming a photoresist pattern wherein a photoresist coating film of naphthoquinone diazide sulfonate of novolak is formed on a substrate layer, the photoresist coating film is exposed by selectively irradiating with near ultraviolet radiation of 350 to 450 nm through a photomask, and the exposed photoresist coating film is developed with an either a negative type or positive type developing solution. The resultant photoresist pattern is usable for manufacturing a highly integrated circuit such as LSI which requires fine processing techniques.

Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.

Abstract: A positive type photoresist composition comprising an m-hydroxy-.alpha.-methylstyrene polymer and as a photo-sensitizer a quinonediazide compound is disclosed. A positive type photoresist composition comprising an m-hydroxy-.alpha.-methylstyrene polymer, a novolak resin, and as a photo-sensitizer a quinonediazide compound, is also disclosed.

Abstract: A moisture-sensitive element is produced by applying an ultraviolet-setting alkali-elution type resist ink on a prescribed part of a cation-exchange membrane, curing and drying the applied layer of the resist ink, chemically plating the cation-exchange membrane thereby forming electrode layers thereon, and thereafter removing the resist ink from the cation-exchange membrane.

Abstract: A positive type resist material with high oxygen plasma resistance and a process for forming high resolution resist patterns using the resist material are disclosed. The positive type resist material comprises a photoactive resin, an organic solvent, and 5 to 50% by weight of trimethylsilylnitrile.A compound of a phenol resin having phenolic hydroxyl groups and a photoactive compound, or phenolformaldehyde is used as an example of the photoactive resin. As the solvent, selected from the group consisting of 1,2-ethoxyl acetate, methyl ethyl ketone, xylene, and n-butyl acetate are used alone or in combination.

Abstract: There is disclosed a photoresist composition comprising a light-sensitive, quinone diazide polymer, a binder and a benzene monomer trisubstituted with a diazo-naphthoquinone-sulfonyloxy group. The composition is improved in that the diazo-naphthoquinone-sulfonyloxy group occupies the 1,2,4-positions on the benzene ring, whereby improved solubility is achieved.

Abstract: An electrodepositable photosensitive modified phenolic novolak resin of general formula ##STR1## where Ar.sup.1 represents a divalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,Ar.sup.2 represents a trivalent aromatic group linked through aromatic carbon atoms to the indicated groups --OR.sup.2 and --CH(R.sup.1)--,R.sup.1 represents a hydrogen atom or an alkyl, aryl or carboxyl group,R.sup.2 represents a hydrogen atom, an alkyl group which may be substituted by a hydroxyl or alkoxy group, or a group of formula --CO--R.sup.3 --COOH, --SO.sub.2 R.sup.4, --COR.sup.5 or --SO.sub.2 R.sup.5, at least 1% of the groups R.sup.2 representing a group --CO--R.sup.3 --COOH and at least 4% of the groups R.sup.2 representing a group --SO.sub.2 R.sup.4,R.sup.3 denotes a divalent aliphatic, cycloaliphatic, aromatic or araliphatic group,R.sup.4 denotes a 1,2-benzoquinone diazide group or 1,2-naphthoquinone diazide groupR.sup.

Abstract: There is disclosed a resist comprising a radiation-sensitive sensitizer that produces, with a binder, imagewise differential solubility when imagewise exposed.

Abstract: A positive photoresist is electrodeposited onto a substrate, exposed to actinic radiation in a predetermined pattern, and then exposed areas are removed by contact with a developer.When the substrate is a metal-faced laminate, the exposed metal surface may be etched and the residual electrodeposited layer removed by contact with a suitable solvent, optionally after a second, general, exposure to actinic radiation.Suitable electrodepositable positive photoresists include o-nitrocarbinol esters and o-nitrophenyl acetals, their polyesters and end-capped derivatives and quinone diazide sulphonyl esters of phenolic novolaks, having salt-forming groups in the molecule, especially carboxylic acid and amine groups.The process is suitable for the production of printing plates and printed circuits, especially circuits on both sides of a liminate sheet linked conductively through metal-lined holes in the sheet.

Abstract: Positive deep ultra-violet photoresists which are base developable comprise base soluble polymers and as photosensitive solubilizing agents oligomeric compounds of the formula ##STR1## wherein X is alkylene, arylene, alkoxyalkylene or aralkylene and n is a positive integer such that the molecular weight of the oligomeric compound is from about 500 to about 3000.

Abstract: Disclosed is a novel novolak resin comprising structural units having a trimethylsilyl group. A resist material highly resistive to dry etching is obtained by adding a photosensitive diazo compound to this novolak resin. The resist material is useful in various lithography methods to form a positive resist pattern. This resist material is used in a pattern forming method of a two-layer type, in which a fine pattern is formed in a thin film of the resist material by lithography and then transferred into an underlying thick organic polymer layer by dry etching of the underlying layer with the resist pattern as mask. Curing of the resist pattern by irradiation with deep UV rays is effective for further improvement in the precision of the transferred pattern.

Abstract: Oligomeric and/or polymeric polyoxazole and polythiazole precursors can be prepared with high purity, i.e., especially without chloride, in a simple manner if an aromatic and/or heterocyclic dihydroxy, dialkoxy or diaryloxydiamino compound or a corresponding dithio compound is reacted with a dicarboxylic acid in the presence of a carbodiimide. The precursors prepared in this manner are suitable, for instance, for the manufacture of protection and insulating layers.

Abstract: A process for forming patterns with a negative type resist which comprises the steps of forming a negative type resist film made of quinone diazide oligomer having a polymerization degree of 10 or less, such as a quinone diazide sulfonic ester on a substrate, irradiating the resist film selectively with far ultraviolet rays having a wavelength of 180-300 nm to expose the above film, and then developing the film thus exposed by the use of a suitable developer such as a solution containing any one of an acetic ester, an alkyl ketone and cyclohexanone, and another process wherein the above described exposing step is carried out in such a manner that the quinone diazide sulfonic ester film is subjected to blanket exposure by means of ultraviolet rays having a longer wavelength than 300 nm, and then the resist film, thus exposed, is further subjected to selective exposure by means of far ultraviolet rays of 300 nm or less.

Abstract: A negative type resist for high energy beam such as electron beam, X-rays or the like made from quinone diazide ester of an oligomer having a polymerization degree of 1-20, and a process for forming a pattern with the same type resist.

Abstract: A photo- and electron resist distributed in an organic solvent, and including an additive which forms a donor-acceptor complex to eliminate luminescence effects and increase the stability of the resist.The photo- and electron resist can be used in microelectronics, optics, printing and precision machine building industry when resists are employed to manufacture structures of semiconductor devices and solid-state circuits.

Abstract: A photosensitive composition containing a polymer, and a photosensitive material utilizing the composition are disclosed. The polymer, which may be in the form of a copolymer, includes a repeating unit of the formula (I): ##STR1## wherein Y is a divalent substituent; Z.sub.1 and Z.sub.2 independently each represents monovalent substituents; p and q are each 0 or an integer of 1 to 4; when p and q are each 2 or more, each of Z.sub.1 and Z.sub.2 may be the same or different; X.sup..crclbar. is an anion. The composition has high sensitivity and is capable of forming an image on a suitable photographic support without causing fog under incandescent lamps. The composition can be used to produce lithographic printing plates having high sensitivity as well as excellent ware resistance.

Abstract: A light-sensitive mixture comprising a water-insoluble binder soluble in aqueous alkaline solutions, and the reaction product of a naphthoquinonediazidesulfonyl halide with a mixture composed of a low molecular weight compound having a definite structure and molecular size containing at least one phenolic hydroxyl group, and of a polymeric compound having recurring units, each of which contains at least one phenolic hydroxyl group. The mixture is useful in producing printing plates and photoresists and has the advantage that the naphthoquinonediazidesulfonic acid ester contained therein is non-explosive.

Abstract: A negative-working image forming process which comprises uniformly exposing a photosensitive material comprising a support having thereon a sensitive layer comprising (i) an o-quinonediazide compound and (ii) a second compound, to actinic radiation which is able to convert the o-quinonediazide compound to the corresponding indenecarboxylic acid compound, and subsequent to said uniformly exposing imagewise exposing said exposed photosensitive material to a laser beam to thereby render the indenecarboxylic acid compound of the imagewise exposed areas convert to the corresponding indene compound and developing with an alkaline developing solution to dissolve out the unexposed area to the laser beam, wherein said second compound reduces the rate of dissolution of the laser exposed areas in the developing solution by converting the indenecarboxylic acid to the corresponding indene compound, whereby said image results.

Abstract: The photosensitive composition suitable as a posi-posi photosensitive composition for photosensitive lithographic printing plates is composed of a high molecular compound shown by following general formula I or II and an o-naphthoquinonediazide compound; ##STR1## wherein R.sub.1 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms and R.sub.2 and R.sub.3 each is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.When the photosensitive composition is used as a photosensitive layer of a photosensitive lithographic printing plate and the plate is developed by rubbing with a sponge containing a developer, the photosensitive composition at the exposed areas is completely removed leaving no patches of the composition.

Abstract: A positive-working photosensitive composition comprising (a) an o-quinonediazide compound and (b) a condensed resin containing a condensation unit composed of an aromatic compound having a carboxylic group and a phenolic ahydroxyl group, and an aldehyde or ketone is disclosed. Said condensation unit has the following formula (I): ##STR1## wherein R.sub.1 is a hydrogen atom, a hydroxyl group, an acyloxy group, an alkyl group, an alkoxy group or a halogen atom, which may be the same or different when n is 2; R.sub.2 and R.sub.3 are each a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, a phenyl group or a substituted phenyl group, which may be the same or different; and n is 1 or 2.

Abstract: Cresol-formaldehyde novolak resins made from a mixture containing meta- and paracresol or ortho-, meta- and paracresol in a ratio selected from a given range for use in fast positive photoresist compositions together with one or more sensitizing compounds. When dissolved in a mixture of organic solvents, the photoresist compositions are suitable for application as a thin coating to a substrate. After the coating has been dried, the coated substrate can be exposed to image-wise modulated actinic radiation and developed in alkaline solution, yielding a relief pattern of resist on substrate useful for a number of applications.

Abstract: A novel photosensitive film structure comprises a generally continuous minor phase material and a generally discontinuous major phase material. The minor phase includes a photosensitive compound whose solubility relative to a selected solvent changes upon exposure to electrromagnetic radiation, while the major phase is not photosensitive nor soluble in the solvent. The two phases are uniformly interdispersed throughout the film structure. Imagewise exposure to electromagnetic radiation renders the film structure selectively permeable to the selected solvent, and, after development, the film structure exhibits the chemical and physical properties of the major phase material. The film structure finds varied application in the manufacture of graphic arts articles such as lithographi printing plates and photoresists.

Abstract: Photoresist compositions are provided whereby metals are incorporated into the resist by providing a photoresist composition comprising the reaction product of an organic resist which has at least one reactive hydroxyl or amino group with an organometallic compound. Also provided is a process for generating a pattern on a substrate by coating the substrate with a thin film of the photoresist composition which comprises the reaction product of the organic resist which has at least one reactive hydroxyl or amino group with an organometallic compound. The photoresist compositions are particularly suitable for use in diazo-type electron beam procedures.

Abstract: A light-sensitive printing plate precursor is disclosed. The printing plate precursor is comprised of an aluminum support base having provided on a grained and anodized surface. The surface is coated with a layer which is comprised of a positive working light-sensitive composition and an oxonol dye. The printing plate has high printing durability, high water retention ability and high color stain resistance. When used the plate precursor provides an image having high contrast. The plate precursor forms less color stain than conventional plates whether used with a fresh developing solution or a fatigued developing solution. The plate precursor does not result in causing uneven development when using manual development methods.

Abstract: A light-sensitive composition containing a high molecular compound and a light-sensitive o-naphthoquinonediazide compound is disclosed. The high molecular compound includes a structure unit represented by the general formula (I): ##STR1## wherein R is a hydrogen atom or a methyl group, and Y is a phenylene group, a substituted phenylene group, a naphthylene group or a substituted naphthylene group. The light-sensitive composition makes possible the production of a light-sensitive material which can be developed under a wide range of development conditions to provide a lithographic printing plate having high printing durability.

Abstract: There is disclosed a photosensitive composition comprising an o-quinonediazide compound and, as a binder resin, a resin containing in the molecule the unit represented by the following formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 have the same meanings as defined in the specification.The photosensitive composition according to the present invention has excellent resistance to chemicals and long press-life, and is excellent in alkali-solubility and difficult to form scumming.

Abstract: A posi-type photosensitive composition having enhanced sensitivity is prepared by incorporating a specific sensitizer selected from gallic acid, its derivative, naphthoquinone compound and its derivative in a quinonediazide type photosensitive material. The composition is free from lowering in development tolerance and other properties.

Abstract: A developing process suitable to treat a positive photosensitive lithographic printing plate comprising a photosensitive layer containing, as the photosensitive constituent, an o-quinonediazide compound provided on an aluminium plate. A positive photo-sensitive lithographic printing plate is exposed imagewise and then developed with a developing solution containing an aqueous solution of an alkali metal silicate in which the alkali metal is essentially constituted by potassium. With the method, development treatment can be conducted stably for a long period without generating insolubes in the developing solution even when an extremely large quantity of positive photosensitive lithographic plates are treated.

Abstract: A photosensitive composition for making lithographic printing plate and for use as a photoresist material which comprises a photosensitive o-quinone diazide compound, an alkali-soluble resin, and 0.5 to 20% by weight 6-membered cyclic acid anhydride.

Abstract: A light-sensitive mixture comprising a water-insoluble binder soluble in aqueous alkaline solutions, and the reaction product of a naphthoquinonediazidesulfonyl halide with a mixture composed of a low molecular weight compound having a definite structure and molecular size containing at least one phenolic hydroxyl group, and of a polymeric compound having recurring units, each of which contains at least one phenolic hydroxyl group. The mixture is useful in producing printing plates and photoresists and has the advantage that the naphthoquinonediazidesulfonic acid ester contained therein is non-explosive.

Abstract: A light-sensitive composition, especially suitable for preparation of planographic printing plates, comprising a water-insoluble resinous binder which is soluble or swellable in aqueous alkaline solutions, and a naphthoquinonediazide sulfonic acid ester of the general formula I ##STR1## wherein D represents a 1,2-naphthoquinone-2-diazide-4-sulfonyl or 1,2-naphthoquinone-2-diazide-5-sulfonyl radical and R represents an alkyl or aryl radical. Printing plates produced with such compositions exhibit good resistance to aqueous alkaline developers, alcohol-containing moistening liquids and gasoline hydrocarbons.

Abstract: The invention relates to heat-resistant positive resists based upon precursor stages of highly heat-resistant polymers and light-sensitive diazoquinones, as well as to a method for preparing heat-resistant relief structures of such positive resists. The positive resists of the type mentioned are developed in such a manner that they are heat-resistant as well as have a long storage life and are easily processed. The invention provides for the use of oligomer and/or polymer precursor stages of polyoxazoles in the form of polycondensation products of aromatic and/or heterocyclic dihydroxydiamino compounds and dicarboxylic acid chlorides or esters. The positive resists according to the invention are suitable especially for applications in microelectronics.

Abstract: The photosensitive printing plate of this invention features incorporation of an organic foaming agent in the photosensitive composition that constitutes the photosensitive layer, said organic foaming agent being thermally decomposed upon drying of said composition under heating to thereby roughen the surface of the photosensitive layer. According to this invention, no specific mechanical treatment is required for forming the photosensitive layer and also there is no need of remodeling the existing coating equipments, and further, the vacuum contact time can be appreciably lessened, so that this invention can greatly improve the working efficiency in plate making and markedly reduce the production cost.