Polymeric Mixture Patents (Class 430/192)
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Patent number: 5260162Abstract: 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.Type: GrantFiled: December 17, 1990Date of Patent: November 9, 1993Inventors: Dinesh N. Khanna, Robert E. Potvin
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Patent number: 5258257Abstract: The invention provides a radiation sensitive composition having a polymer binder of phenolic and cyclic alcohol units. At least a portion of the phenolic units and/or cyclic alcohol units of the polymer are bonded to acid labile groups. High solubility differentials between exposed and unexposed regions are realized with only moderate substitution of the binder with the acid labile groups.Type: GrantFiled: September 23, 1991Date of Patent: November 2, 1993Assignee: Shipley Company Inc.Inventors: Roger Sinta, Richard C. Hemond, David R. Medeiros, Martha M. Rajaratnam, James W. Thackeray, Dianne Canistro
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Patent number: 5256517Abstract: 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.Type: GrantFiled: May 1, 1991Date of Patent: October 26, 1993Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
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Patent number: 5254432Abstract: The present invention relates to a photosensitive composition comprising an o-quinonediazide compound and a polyurethane resin having a phosphonic acid group, a phosphoric acid group or its ester group. The photosensitive composition of the present invention provides an excellent adhesion to the support, an excellent developability with an aqueous alkali developer, and a high printing durability.Type: GrantFiled: April 26, 1990Date of Patent: October 19, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshiaki Aoai
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Patent number: 5254440Abstract: A methylol-substituted trihydroxybenzophenone of the formula (I): ##STR1## This methylol-substituted trihydroxybenzophenone may be reacted with selected phenolic monomers during or after the formation of a phenolic novolak resin thereby said resin having at least one unit of formula (II): ##STR2## wherein R and R.sub.1 are individually selected from hydrogen, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms.Type: GrantFiled: September 30, 1992Date of Patent: October 19, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Medhat A. Toukhy
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Patent number: 5252686Abstract: A novel siloxane polymer having at least 1 mol % of a structural unit derived from a cyclic heat addition product between a diene compound of formula (I) or (II) and an olefin or acetylene compound of formula (III), (IV) or (V): ##STR1## and a positive working light-sensitive composition comprising the siloxane polymer.Type: GrantFiled: August 28, 1992Date of Patent: October 12, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kazuyoshi Mizutani
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Patent number: 5250653Abstract: A phenolic novolak resin composition comprising a condensation product of at least one aldehyde source with a phenolic source comprising 5-indanol. Said phenolic novolak resins are used in radiation-sensitive compositions, especially those useful as positive-working photoresists.Type: GrantFiled: February 22, 1993Date of Patent: October 5, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Medhat A. Toukhy
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Patent number: 5250669Abstract: 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.Type: GrantFiled: April 23, 1992Date of Patent: October 5, 1993Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Kazufumi Ogawa, Masayuki Endo, Keiji Ohno, Mamoru Nagoya
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Patent number: 5250385Abstract: A photopolymerizable composition comprises a photopolymerizable ethylenically unsaturated compound having at least two terminal ethylene groups, a photopolymerization initiator and an organic polymer binder, wherein the photopolymerization initiator is an aromatic sulfonic acid salt of an onium compound. The composition has high sensitivity to actinic rays over a wide range of wavelength extending from ultraviolet to visible region and thus can be used for preparing a lithographic printing plate, a resin-letterpress plate, a resist or photomask for making a printed board, a monochromatic and colored sheet for transfer or color-development and a color-developing sheet.Type: GrantFiled: August 30, 1991Date of Patent: October 5, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Yoshimasa Aotani, Akira Umehara, Tsuguo Yamaoka
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Patent number: 5248582Abstract: 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.Type: GrantFiled: December 8, 1992Date of Patent: September 28, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuya Uenishi, Shinji Sakaguchi, Tadayoshi Kokubo
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Patent number: 5248585Abstract: This invention relates to novel radiation sensitive compositions. More particularly the invention relates to photoresists containing phosphorus and nitrogen linked polymers; i.e., polyphosphazenes, useful in the preparation of a relief pattern on a substrate; e.g., a silicon wafer or aluminum plate. The polyphosphazenes of in this invention can be synthesized by the condensation of N-trimethylsilylalkoxyphosphorimides. Radiation sensitive positive photoresist compositions of the invention can be developed in aqueous base developer or organic solvent developer The base developer dissolution properties of the composition can be controlled by incorporating carboxylate groups into the polyphosphazene. The polyphosphazenes utilized in this invention have good solubility properties in various organic solvents and also have good mechanical, electrical, adhesion and thermal properties.Type: GrantFiled: December 18, 1991Date of Patent: September 28, 1993Assignee: Hoechst Celanese CorporationInventors: Thomas J. Lynch, Dana L. Durham, Chester Sobodacha
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Patent number: 5246818Abstract: A developer composition for positive color proofing films containinga) sodium, potassium or ammonium octyl sulfate; sodium, potassium or ammonium lauryl sulfate; sodium decyl sulfate; or sodium tetradecyl sulfate; andb) sodium or potassium borate; andc) boric acid; andd) monobasic sodium or potassium phosphate; ande) sodium or potassium citrate; andf) sodium or potassium salicylate; andg) sodium, potassium or lithium benzoate; andh) sufficient water to formulate an effective developer.Type: GrantFiled: August 16, 1989Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventor: Shuchen Liu
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Patent number: 5242780Abstract: An electrophoretic positive working photosensitive composition for producing a photoresist pattern on metal base plate comprises a photosensitive compound, in which a photosensitive quinone diazide group is grafted on a polyester, and an acrylic copolymer containing carboxyl group, the composition forms a smooth photoresist film on the plate and has a good adhesion to the surface that no pinehole is found.Type: GrantFiled: October 18, 1991Date of Patent: September 7, 1993Assignee: Industrial Technology Research InstituteInventors: Hsien-Kuang Lin, Jim-Chyuan Shieh, Dhei-Jhai Lin
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Patent number: 5240819Abstract: This invention is that of high temperature polyamides containing the hexafluoroisopropylidene group. The high temperature polyamides of the invention and photo or radiation sensitizers provide improved high temperature positive resists which can be developed in aqueous alkaline developer and thermally anneal to form heat resistant, polyoxazole relief structures suitable for use in microelectronic and printing applications. The positive photoresists of the invention have improved solubility in coating solvents and improved photospeed. The polyamides of the invention can be prepared by conventional condensation reactions; e.g. the condensation of a diamine and diacid chloride. In addition the polyamides of this invention provide high temperature protective coatings with superior adhesion properties in applications other than the photoresist area.Type: GrantFiled: March 11, 1991Date of Patent: August 31, 1993Assignee: Hoechst Celanese CorporationInventors: Werner H. Mueller, Dinesh N. Khanna, Bernd Hupfer
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Patent number: 5238776Abstract: 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.Type: GrantFiled: February 27, 1991Date of Patent: August 24, 1993Assignee: Shipley Company Inc.Inventor: Anthony Zampini
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Patent number: 5238771Abstract: There are disclosed a photosensitive composition which comprises:(1) an o-naphtoquinonediazide compound;(2) an alkali soluble resin; and(3) any one selected from the groups consisting of:(a) an ester compound of a polyoxyalkylene sorbitol fatty acid and/or an ether compound of the fatty acid,(b) an alkylene oxide adduct of castor oil, hardened castor oil, lanolin alcohol, beeswax, phytosterol or phytostanol, and(c) at least one activator selected from the group consisting of polyoxypropylene alkyl ethers, polyoxypropylene alkylphenyl ethers and polyoxypropylene alkyl esters;.and a photosensitive lithographic printing plate which comprises a support; and a photosensitive layer formed by applying the above photosensitive composition.Type: GrantFiled: October 19, 1992Date of Patent: August 24, 1993Assignees: Konica Corporation, Mitsubishi Kasei CorporationInventors: Kiyoshi Goto, Hideyuki Nakai, Hiroshi Tomiyasu, Yoshiko Kobayashi
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Patent number: 5238775Abstract: 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.Type: GrantFiled: February 19, 1991Date of Patent: August 24, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Toru Kajita, Takao Miura, Yoshiji Yumoto, Chozo Okuda
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Patent number: 5238784Abstract: The present invention provides a photosensitive resin composition which comprises, as essential components:(A) a polyamic acid having a recurring unit represented by the following formula [I]: ##STR1## wherein R.sub.1 and R.sub.2 each represents an organic group selected from the group consisting of an aromatic group, an alicyclic group, an aliphatic group, and a heterocyclic group and m is 1 or 2,(B) an amide compound having carbon-carbon double bond, and(C) a photosensitizer.Type: GrantFiled: November 28, 1990Date of Patent: August 24, 1993Assignee: Sumitomo Bakelite Company LimitedInventors: Akira Tokoh, Nobuyuki Sashida, Etsu Takeuchi, Takashi Hirano
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Patent number: 5238773Abstract: A composition containing an organosilicon material having terminal quinone groups, and a phenolic-novolak polymer, and use thereof in photolithography.Type: GrantFiled: June 8, 1992Date of Patent: August 24, 1993Assignee: International Business Machines CorporationInventors: Edward D. Babich, Donis G. Flagello, Michael Hatzakis, Jurij R. Paraszczak, Jane M. Shaw, David F. Witman
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Patent number: 5238774Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymonocarboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.Type: GrantFiled: June 4, 1991Date of Patent: August 24, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Patent number: 5235022Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic polymer and a reactive ortho, ortho bonded oligomer having the formula: ##STR1## wherein x is from 2 to 7; wherein R is selected from hydrogen a lower alkyl group or lower alkoxy group having 1-4 carbon atoms and a halogen group; and Y.sub.1 is either a hydroxyl group; an alkoxy group or a halogen group; and Y.sub.2 is hydrogen, alkyl, alkoxy, halogen, hydroxyl, --CH.sub.2 OH, --CH.sub.2 -- halogen, or --CH.sub.2 -alkoxy group.Type: GrantFiled: November 23, 1992Date of Patent: August 10, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
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Patent number: 5234793Abstract: A photolithographic method for structure generation in bilayer processes is provided. Pursuant to the method, a dimensional reserve is produced in a top resist structure by chemical treatment with a bulging agent. The expansion preferably is performed by treatment with an aqueous solution. The expansion can be set such that the dimensional loss to be anticipated in further etchings of the bottom resist or, respectively, of the wafer is exactly compensated for.Type: GrantFiled: April 24, 1990Date of Patent: August 10, 1993Assignee: Siemens AktiengesellschaftInventors: Michael Sebald, Recai Sezi, Rainer Leuschner, Siegfried Birkle, Hellmut Ahne
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Patent number: 5234795Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic polymer and a reactive ortho, ortho bonded oligomer having the formula: ##STR1## wherein x is from 2 to 7; wherein R is selected from hydrogen a lower alkyl group or lower alkoxy group having 1-4 carbon atoms and a halogen group; and Y.sub.1 is either a hydroxyl group; an alkoxy group or a halogen group; and Y.sub.2 is hydrogen, alkyl, alkoxy, halogen, hydroxyl, --CH.sub.2 OH, --CH.sub.2 -- halogen, or --CH.sub.2 --alkoxy group.Type: GrantFiled: November 23, 1992Date of Patent: August 10, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
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Patent number: 5232819Abstract: Block phenolic oligomers of the formula (I): ##STR1## These may be reacted alone or with selected phenolic monomers during or after the formation of a phenolic novolak resin thereby said resin having at least one unit of formula (II): ##STR2##Type: GrantFiled: December 3, 1992Date of Patent: August 3, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
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Patent number: 5232816Abstract: A positive type photosensitive resinous composition comprising a binder resin and a quinone diazide compound, the binder resin being a copolymer of(a) at least one phosphoric acid ester monomer represented by the formula: ##STR1## (b) at least one acid group containing .alpha.,.beta.-ethylenically unsaturated monomer, and(c) other copolymerizable .alpha.,.beta.-ethylenically unsaturated monomers than (a) and (b), which is specifically useful for the formation of resist coating in the preparation of printed circuit board.Type: GrantFiled: August 31, 1990Date of Patent: August 3, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Mamoru Seio, Takeshi Ikeda, Kiyomi Sakurai
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Patent number: 5229245Abstract: A positively working photosensitive composition is disclosed useful for making positively working lithographic printing plates of exceptional wear, printing and solvent-resistant characteristics. The positively working photosensitive composition essentially contains a .beta.-dicarbonyl group and a quinone diazide group.Type: GrantFiled: July 26, 1991Date of Patent: July 20, 1993Assignee: Industrial Technology Research InstituteInventors: Dhei-Jhai Lin, Hsien-Kuang Lin, Jim-Chyuan Shieh
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Patent number: 5229244Abstract: The present invention concerns a phototackifiable composition useful as a coating on a substrate consisting of an optically clear blend of two or more polymers and a photosensitive compound that forms a strong acid on exposure to actinic radiation. The invention also relates to a process for coating such a composition on a support and toning the image-wise exposed composition on the support.Type: GrantFiled: June 29, 1992Date of Patent: July 20, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Walter R. Hertler, Howard E. Simmons, III
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Patent number: 5227473Abstract: 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.Type: GrantFiled: May 10, 1991Date of Patent: July 13, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Satoshi Takita
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Patent number: 5227280Abstract: A PMGI bilayer resist for integrated circuit fabrication having increased sensitivity to light and formed by the addition of cyclic anhydrides to the resist and the formation of an accompanying bilayer resist structure of a portable conforming mask having a desirable undercut profile for lift-off of patterned metallic circuitry.Type: GrantFiled: September 4, 1991Date of Patent: July 13, 1993Assignee: International Business Machines CorporationInventors: James A. Jubinsky, Steven M. Katz, Christopher F. Lyons, Wayne M. Moreau
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Patent number: 5225318Abstract: 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.Type: GrantFiled: June 29, 1992Date of Patent: July 6, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Sobhy Tadros
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Patent number: 5225312Abstract: A positive photoresist of the type containing an alkali-soluble novolac resin and a quinone diazide sensitizer contains a dye of the general formula: ##STR1## wherein R' is lower alkyl, R" is H, alkyl or CO.sub.2 -alkyl, alkyl-CO.sub.2 -alkyl or alkyl-CO.sub.2 -(C.sub.1 -C.sub.3 alkyl-O).sub.n -alkyl (n=1-3) and wherein said dye is compatible with the novolac resin/quinone diazide formulation to at least 0.1 phr. The dye reduces reflective notching. Preferably the photoresist also contain a nitro naphthol dye to reduce the effects of I-Line radiation.Type: GrantFiled: August 2, 1991Date of Patent: July 6, 1993Assignee: Morton International, Inc.Inventors: Sunit S. Dixit, Richard M. Lazarus, Thomas P. Carter, Joseph E. Oberlander, Andreas Goehring, Randall W. Kautz, Grieg Beltramo
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Patent number: 5225311Abstract: A positive photoresist composition is disclosed, comprising (a) from 50 to 99 parts by weight of a polyhydric phenol compound which is a condensation product between a mixed phenol comprising o-cresol and at least one of 2,5-dimethylphenol and 3,5-dimethylphenol at a molar ratio of from 95/5 to 5/95 and an aldehyde and (b) from 1 to 50 parts by weight of a quinone diazide compound. The composition is excellent in sensitivity, resolving power, heat resistance, and resistance to dry etching.Type: GrantFiled: April 5, 1991Date of Patent: July 6, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Toshitomo Nakano, Masumi Kada
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Patent number: 5225310Abstract: The invention relates to a photosensitive mixture which essentially contains an ester or an amide of a 1,2-naphthoquinonediazide sulfonic or carboxylic acid as the photosensitive compound, a phenolic resin which is soluble in aqueous-alkaline solutions and insoluble in water as the binder, and an additional speed enhancer, which corresponds to the general formula ##STR1## where X denotes a single bond, CH.sub.2, SO.sub.2, S, CO, C(CH.sub.3).sub.2, CHCC1.sub.3 or ##STR2## Biphenyldiol-(4,4'), bis-(4-hydroxyphenyl)-ketone, 2,2-bis-(4-hydroxy-phenyl)-propane or bis-(4-hydroxyphenyl)-sulfone are described as suitable compounds. The mixture is employed as photosensitive layers in recording materials suitable for the production of printing forms.The invention provides for an increased photospeed, without any disadvantages occurring in respect of the copying or printing behavior.Type: GrantFiled: June 2, 1988Date of Patent: July 6, 1993Assignee: Hoechst AktiengesellschaftInventors: Paul Stahlhofen, Otfried Gaschler
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Patent number: 5223372Abstract: A chemical mat film having good writability and printability is disclosed which includes a transparent film, a chemical mat layer provided on one or both sides of the transparent film and containing finely divided solid particles which provide surface roughness, and an overcoat layer formed of a polymeric material and provided over the surface of the chemical mat layer, the overcoat layer having a surface roughness which is substantially coincident with that of the chemical mat layer. The chemical mat film may be used as a substrate of a photosensitive film for supporting a photosensitive layer thereon.Type: GrantFiled: September 22, 1989Date of Patent: June 29, 1993Assignee: Somar CorporationInventors: Shinichi Yamamoto, Hiromi Masamura
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Patent number: 5223373Abstract: 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.Type: GrantFiled: April 29, 1991Date of Patent: June 29, 1993Assignee: Industrial Technology Research InstituteInventors: Hsien-Kuang Lin, Jim-Chyuan Shieh
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Patent number: 5221592Abstract: 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.Type: GrantFiled: March 6, 1992Date of Patent: June 22, 1993Assignee: Hoechst Celanese CorporationInventors: Dinesh N. Khanna, Douglas McKenzie, Chester J. Sobodacha, Ralph R. Dammel
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Patent number: 5219714Abstract: 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.Type: GrantFiled: September 14, 1992Date of Patent: June 15, 1993Assignee: OCG Microelectronic Materials, Inc.Inventors: Medhat A. Toukhy, Alfred T. Jeffries, III
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Patent number: 5219701Abstract: Structures of high resolution in the near UV range and of high sharpness of edge and steepness of edge can be obtained by means of positive photoresists containing, in an organic solvent, in each case essentially at least(a) an alkali-soluble resin(b) a 1,2-naphthoquinone-diazide-5-sulfonyl ester of a trihydroxybenzene isomer(c) an aromatic hydroxy compoundand also, if appropriate, further customary additives, and in which the result of component (b) is to give an absorption coefficient of at least 0.5 .mu.m.sup.-1 for the photobleachable absorption, and component (c) is present in a concentration of 15-30% by weight, relative to the total solids content.Type: GrantFiled: October 2, 1991Date of Patent: June 15, 1993Assignee: Ciba-Geigy CorporationInventors: Reinhard Schulz, Horst Munzel
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Patent number: 5219700Abstract: A photosensitive composition comprising (a) a 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound, (b) alkali-soluble resin, (c) a halomethyloxadiazole compound which releases halogen free radicals by irradiation with actinic rays and (a) a dye which interacts withthe decomposition product of said halomethyloxydiazole compound and discolors or develops color. The composition exhibits excellent development latitude, light safety, visible-on-exposure characteristic and printing resistance.Type: GrantFiled: March 24, 1992Date of Patent: June 15, 1993Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
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Patent number: 5217851Abstract: A pattern forming method providing a satisfactory pattern shape of high resolution power and high sensitivity. A pattern forming material comprising a resin containing hydroxyl groups is coated on a substrate and selectively exposed by Deep UV light using an optional mask. Then, the surface of the unexposed area is selectively silylated by hexamethyl disilazane and, thereafter dry-developed by reactive ion etching using O.sub.2 gas. With such a constitution, the exposed area and the unexposed area can be distinguished clearly to obtain a resist pattern of high resolution power. Further, since the Deep UV light has a property of being strongly absorbed to the resist film, the sensitivity is increased. Further, since the Deep UV light does not reach as far as the lower portion of the resist film, no undesirable notching phenomenon occurs even if there is any step on the substrate to be fabricated.Type: GrantFiled: October 10, 1991Date of Patent: June 8, 1993Assignee: Mitsubishi Denki Kabushiki KaishaInventors: Shinji Kishimura, Akemi Fukui
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Patent number: 5215856Abstract: 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 tris (hydroxyphenyl) lower alkane compound; 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.Type: GrantFiled: September 19, 1989Date of Patent: June 1, 1993Assignee: OCG Microelectronic Materials, Inc.Inventor: Tripunithura V. Jayaraman
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Patent number: 5215858Abstract: A photosensitive resin composition comprising (A) an alkaline aqueous solution-soluble novolak resin, (B) a photosensitizer obtained by reacting a polyhydroxy compound with 1,2-naphthoquinone-(2)-diazido-5(or 4)-sulfonyl chloride, and (C) an ultraviolet absorber such as 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, has a strong absorption against a light of a wavelength of 365 nm and is suitable for producing semiconductor elements, etc.Type: GrantFiled: March 21, 1989Date of Patent: June 1, 1993Assignees: Hitachi Chemical Company, Ltd., Hitachi, Ltd.Inventors: Shigeru Koibuchi, Asao Isobe, Michiaki Hashimoto
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Patent number: 5215857Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymonocarboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.Type: GrantFiled: July 3, 1991Date of Patent: June 1, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Patent number: 5213941Abstract: This invention provides an improved negative-working or positive-working, single sheet color proofing method which can accurately reproduce images by using colored, photosensitive layers on substrates which are then overcoated with partially developable adhesive layers. The final construction is useful in predicting the image quality from a lithographic printing process. The partial removal of the adhesive layers cleans out any background stain which may remain from the incomplete removal of the photosensitive layer.Type: GrantFiled: October 21, 1988Date of Patent: May 25, 1993Assignee: Hoechst Celanese CorporationInventor: Stephan J. W. Platzer
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Patent number: 5212043Abstract: A photoresist composition comprising:a resin soluble in an aqueous alkaline solution, having units of an aliphatic cyclic hydrocarbon main frame and units derived from maleic anhydride and/or units derived from a maleimide; anda photosensitive agent in a sufficient amount to promote or hinder the solubility of said resin in an aqueous alkaline solution upon exposure to active radiation so as to create a substantial difference in the solubility as between an exposed portion and a non-exposed portion and to form a positive or negative image by subsequent development with an aqueous alkaline solution.Type: GrantFiled: October 17, 1990Date of Patent: May 18, 1993Assignee: Tosho CorporationInventors: Takashi Yamamoto, Masaaki Todoko, Toru Seita, Kyoko Nagaoka, Kosaburo Matsumura
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Patent number: 5212044Abstract: A photoresist composition, and a process for using the same are; the composition comprises a polyphenolic resin and a sensitizer effective, when exposed to actinic radiation, to provide alkali solubility to said composition, wherein said resin is represented by the formula (I) or (II): ##STR1## wherein R is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkaryl group or an aryl group; R' is a silyl group; and n and n'+m are greater than 3. The composition exhibits high thermal and plasmal resistance and good dissolution characteristics.Type: GrantFiled: November 13, 1991Date of Patent: May 18, 1993Assignee: The Mead CorporationInventors: Rong-Chang Liang, Alexander R. Pokora, William L. Cyrus, Jr.
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Patent number: 5212042Abstract: A positive type light-sensitive composition is disclosed, comprising an alkali-soluble high-molecular binder and at least one p-iminoquinonediazido-N-sulfonyl compound. This composition can be used for forming a resist for an IC board, a printing plate, a silver-free, image-forming material, etc.Type: GrantFiled: March 2, 1992Date of Patent: May 18, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Fumiaki Shinozaki, Akira Umehara, Sadao Ishige
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Patent number: 5210000Abstract: A photoresist that utilizes a copolymer of a phenol and a cyclic alcohol having increased optical transmission properties relative to photoresists using fully aromatic phenolic resins. Preferred binders are hydrogenated novolak resins and hydrogenated polyvinyl phenol resins.Type: GrantFiled: February 6, 1992Date of Patent: May 11, 1993Assignee: Shipley Company Inc.Inventors: James Thackeray, George W. Orsula, Roger Sinta
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Patent number: 5210003Abstract: Non-polymeric compounds which contain at least one aromatic ring system carrying one or more one or more tetrahydropyranyloxy substituents of formula I ##STR1## wherein R.sub.1 is hydrogen, halogen, alkyl, cycloalkyl, aryl, alkoxy or aryloxy,R.sub.2 is hydrogen, alkyl, cycloalkyl or aryl,R.sub.3 is a saturated or unsaturated hydrocarbon radical,R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, alkyl, alkoxy or aryloxy, andX is a direct single bond or a methylene or ethylene bridge.These compounds are especially suitable for the preparation of photoresist compositions which can be used both for the production of positive as well as negative images. The photoresists are preferably used for deep-UV microlithography.Type: GrantFiled: September 9, 1991Date of Patent: May 11, 1993Assignee: Ciba-Geigy CorporationInventor: Ulrich Schadeli
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Patent number: 5208138Abstract: Novolak resins are provided which are the condensation product of (a) a phenol, phenol derivative, or mixtures thereof, and (b) a mixture of formaldehyde or a formaldehyde precursor and (1) a monohydroxy aromatic aldehyde and wherein at least a portion of the hydroxyl groups thereof are esterified or (2) a mixture of at least one monohydroxy aromatic aldehyde and at least one non-hydroxylic aromatic aldehyde; the novolak resins having a hydroxyl number of from about 120 to about 180 grams of resin per equivalent of hydroxyl. The novolak resins are especially useful in positive photoresist formulations and have enhanced photospeed and film loss characteristics as well as improved thermal stability.Type: GrantFiled: May 21, 1992Date of Patent: May 4, 1993Assignee: Morton International, Inc.Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit