Polymeric Mixture Patents (Class 430/192)
  • Patent number: 4889789
    Abstract: A photosensitive composition which substantially comprises a binder which is insoluble in water and soluble in aqueous-alkaline solutions, a photosensitive 1,2-naphthoquinone-diazide or a photosensitive mixture comprised of a compound which splits off acid upon exposure to light and a compound containing at least one acid-cleavable C-O-C group, and a thermally crosslinking compound comprising a urea or urethane-formaldehyde condensation product is disclosed. Also disclosed is a copying material prepared from this composition. The material has a good shelf life and can be processed as a positive or negative-working material, and also according to the photocomposing method. For development customary developer solutions are used.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: December 26, 1989
    Assignee: Hoechst Aktiengsellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 4885232
    Abstract: The invention provides a method for producing a photographic element which comprises coating a substrate with a positive working photosensitive composition which composition comprises an aqueous alkali soluble resin, a quinone diazide photosensitizer and a solvent composition, heat treating said coated substrate at a temperature of from about 20.degree. C. to about 100.degree. C. until substantially all of said solvent composition is removed; imagewise exposing said photosensitive composition to actinic radiation; baking said coated substrate at a temperature of from about 120.degree. C. to about 160.degree. C. for from about 15 seconds to about 90 seconds; and removing the exposed non-image areas of said composition with a suitable developer.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: December 5, 1989
    Assignee: Hoechst Celanese Corporation
    Inventor: Mark A. Spak
  • Patent number: 4883739
    Abstract: A light-sensitive resin composition comprising a light-sensitive substance represented by the formula (A) shown below and an alkali-soluble resin: ##STR1## wherein R.sub.1 to R.sub.8 are independently hydrogen, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy 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, -OD, or ##STR2## (wherein R is hydrogen, or an alkyl group, and D is a 1,2-naphthoquinonediazido-5-sulfonyl group or a 1,2-naphthoquinonediazido-4-sulfonyl group);R.sub.9 to R.sub.12 are independently hydrogen or a lower alkyl group; andZ is oxygen or a single bond; provided that at least one of R.sub.1 to R.sub.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: November 28, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinji Sakaguchi, Shiro Tan
  • Patent number: 4882260
    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.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: November 21, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hidekatsu Kohara, Nobuo Tokutake, Masanori Miyabe, Toshimasa Nakayama, Shingo Asaumi, Hatsuyuki Tanaka, Yoshiaki Arai
  • Patent number: 4880722
    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.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: November 14, 1989
    Assignee: International Business Machines Corporation
    Inventors: Wayne M. Moreau, Kaolin N. Chiong
  • Patent number: 4873176
    Abstract: The invention provides a method for forming a photoresist mask on a substrate resistant to reticulation during plasma etching. The method comprises the steps of forming an imaged and developed photoresist coating over an integrated circuit substrate where the photoresist contains an essentially unreacted acid activated cross linking agent, and subjecting said substrate to an etching plasma in a gaseous stream that contains a Lewis acid. Contact of the surface of the photoresist film with the Lewis acid causes cross linking of the surface of the photoresist film during plasma etching with the formation of a reticulation resistant surface layer.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: October 10, 1989
    Assignee: Shipley Company Inc.
    Inventor: Thomas A. Fisher
  • Patent number: 4873169
    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.
    Type: Grant
    Filed: August 20, 1987
    Date of Patent: October 10, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Fritz Erdmann, Horst-Dieter Thamm, Hans-Joachim Staudt
  • Patent number: 4871645
    Abstract: A positive-working photoresist composition is disclosed. The composition comprises a light-sensitive compound represented by general formula (A) and an alkali-soluble novolak resin. ##STR1## wherein R.sub.a, R.sub.b, R.sub.c, R.sub.d, R.sub.e and R.sub.f, which may be the same or different, each represents H, --X--R.sub.1, ##STR2## provided that among the six substituents represented by R.sub.a to R.sub.f, the number of the substituents representing H is a real number of more than 0 and not more than 3 calculated in terms of average value per molecule of the light-sensitive compound, the number of the substituents representing --X--R.sub.1 is a real number of not less than 0.3 calculated in terms of average value per molecule of the light-sensitive compound, and the number of the substituents representing ##STR3## is a real number of not less than 2.5 caluclated in terms of average value per molecule of the light-sensitive compound; X represents a simple bond, ##STR4## R.sub.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: October 3, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Tadayoshi Kokubo, Yasumasa Kawabe
  • Patent number: 4871644
    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.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4871646
    Abstract: Disclosed are a polysilane containing a unit represented by the following formulas I, II, or III, and a photosensitive composition consisting of the polysilane.
    Type: Grant
    Filed: May 13, 1988
    Date of Patent: October 3, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shizu Hayase, Rumiko Horiguchi, Yasunobu Onishi, Toru Ushirogouchi
  • Patent number: 4869993
    Abstract: This invention relates to positive working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process. The element is composed of a substrate, colored photosensitive layer and adhesive layer. The adhesive layer contains an optical brightener compound which reduces residual yellow staining derived from the naphthoquinone diazide sensitizer.
    Type: Grant
    Filed: August 29, 1988
    Date of Patent: September 26, 1989
    Inventors: Wahib Farahat, Dennis J. Bellville, Richard L. Shadrach
  • Patent number: 4865945
    Abstract: The present application describes a photoresist material which contains organo-silicon groups and the photoresist material is suitable for forming a micropattern applied in the fabrication of semiconductor integrated circuit and magnetic bubble memory elements. The photoresist material possesses high resistance to plasma etching using oxygen gas.
    Type: Grant
    Filed: August 10, 1987
    Date of Patent: September 12, 1989
    Assignee: Sony Corporation
    Inventors: Tsutomu Noguchi, Keiichi Nito, Junetsu Seto
  • Patent number: 4863828
    Abstract: A positive-working photoresist composition is disclosed, which comprises a light-sensitive substance of 1,2-naphthoquinonediazide-4- and/or -5-sulfonate of 2,3,4,3',4',5'-hexahydroxybenzophenone and an alkali-soluble novolak resin dissolved in ethyl lactate or methyl lactate.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: September 5, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kazuya Uenishi, Tadayoshi Kokubo
  • Patent number: 4863829
    Abstract: A positive type photoresist composition comprising a novolak resin and O-quinone diazide compound, the novolak resin being one which is obtained by the addition condensation reaction of a phenol and formaldehyde which is performed in one stage by using as a catalyst an organic acid salt of a divalent metal which is more electropositive than hydrogen, or in two stages by using an acid catalyst in the subsequent stage, the phenol being at least one compound represented by the formula ##STR1## wherein R is hydrogen or an alkyl group of carbon number 1 to 4, the compound being such that the average carbon number in the substituent per one phenol nucelus is 0.5 to 1.5 and the ones with the substituent at the ortho- or para-position with respect to the hydroxyl group account for less than 50 mol %, is disclosed. The positive type photoresist composition of the invention has an improved resolving power, i.e., .gamma.-value.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: September 5, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akihiro Furuta, Makoto Hanabata, Seimei Yasui, Osamu Hiroaki, Naoyoshi Jinno
  • Patent number: 4859562
    Abstract: A photosensitive mixture that contains a photosensitive compound, for example, a photoinitiator or a diazo compound, and a reaction product of a polymer containing active hydrogen with an olefinically unsaturated compound represented by the formula ##STR1## wherein X and Y are the same or different and denote oxygen or sulfur,R.sub.1 is an olefinically unsaturated aliphatic radical containing 2 to 8 carbon atoms andR.sub.2 is a saturated aliphatic radical containing 1 to 8 carbon atoms or an aryl radical containing 6 to 10 carbon atoms,is suitable for producing photoresists and printing plates.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: August 22, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Jerg Kleiner, Thomas Gerdau
  • Patent number: 4859563
    Abstract: Disclosed herein is a positive photoresist composition containing (a) a photosensitizer of 1,2-napthtoquinone diazides photosensitive-material comprising an ester of 2,3,4,4'-tetrahydroxybenzophenone in which on the average, not less than two hydroxyl groups of 2,3,4,4'-tetrahydroxybenzophenone have been esterified by 1,2-naphthoquinonediazide-5-sulfonic acid and (b) a novolak resin obtained by condensing a mixture of m-cresol, p-cresol and 2,5-xylenol with formaldehyde.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: August 22, 1989
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Konoe Miura, Tameichi Ochiai, Yasuhiro Kameyama
  • Patent number: 4857435
    Abstract: Actinic (deep ultraviolet, ultraviolet and visible) light sensitive positive photoresist compositions containing a mixture of an alkali-insoluble photoactive compound capable of being transformed into an alkali-soluble species upon exposure to actinic radiation, in an amount sufficient to render the mixture relatively alkali insoluble and a polymer comprising an amount of --CO--NH--CO-- groups, such as maleimide and especially maleimide-substituted styrene copolymers, sufficient to render the mixture readily alkali soluble upon exposure to actinic radiation are disclosed. The preferred copolymers include maleimide/styrene or .alpha.-methylstyrene in a 1:1 molar ratio. The preferred photoactive compound suitable for a positive photoresist composition responsive to deep UV actinic radiation has the formula 18-B in Table I. The present invention also contemplates photosensitive elements and thermally stable photochemically imaged systems based on the actinic light sensitive positive photoresist compositions.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: August 15, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Frederick R. Hopf, Michael J. McFarland, Christopher E. Osuch
  • Patent number: 4853314
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C-O-C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: August 1, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher
  • Patent number: 4853315
    Abstract: Esters of 1-oxo-2-diazo-naphthalene sulfonic acid wherein the sulfonic acid group is at either the 4 or the 5 position of a hydroxymethyl-tricyclo [5.2.1.0.sup.2,6 ] decane wherein the hydroxy group is either at the 3 or 4 position and useful as sensitizers for positive resists, particularly relatively thick resists at 365 nm.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: August 1, 1989
    Assignee: International Business Machines Corporation
    Inventors: Dennis R. McKean, Robert D. Miller, Joseph G. Walsh, Carlton G. Willson
  • Patent number: 4847178
    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.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: July 11, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroshi Komano
  • Patent number: 4845009
    Abstract: The present invention relates to a photosensitive composition suitable for the use in the preparation of a photosensitive lithographic plate. The photosensitive composition comprises (1) a polymer having a maleimido group in its side chain and being capable of being photocrosslinked, such as a copolymer of methyl methacrylate/N-[2-(methacryloyloxy)-ethyl]-2,3-dimethylmaleimide/methacryl ic acid=15/65/20 (weight ratio) and (2) a diazo resin such as dodecylbenzenesulfonate of condensate of p-diazodiphenylamine and formaldehyde.
    Type: Grant
    Filed: September 17, 1986
    Date of Patent: July 4, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuyuki Kita, Masanori Imai
  • Patent number: 4845008
    Abstract: A positive-working light-sensitive composition is herein disclosed, which comprises a mixed organic solvent consisting of (i) at least one organic solvent having a boiling point of at least 40.degree. C. and less than 100.degree. C., (ii) at least one organic solvent having a boiling point of at least 100.degree. C. and less than 140.degree. C., and (iii) at least one organic solvent having a boiling point of at least 140.degree. C. and less than 210.degree. C.; or (a) at least one organic solvent as defined in the above item (i), (b) at least one organic solvent as defined in the item (ii), (c) at least one organic solvent having a boiling point of at least 210.degree. C.
    Type: Grant
    Filed: February 11, 1987
    Date of Patent: July 4, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Nishioka, Toshimi Hirano, Keiji Akiyama
  • Patent number: 4842983
    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.
    Type: Grant
    Filed: October 14, 1987
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Akira Hasegawa
  • Patent number: 4842986
    Abstract: A positively working resist material is disclosed, comprising a compound having at least one silyl ether group and capable of directly dissociating an Si-O-C bond upon irradiation with far ultraviolet rays, X-rays, an electron beam, or an ion beam. The resist material has high sensitivity to high energy radiation, excellent resistance to dry etching, and can be developed with an alkaline aqueous solution.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuaki Matsuda, Tadayoshi Kokubo, Toshiaki Aoai, Akira Umehara, Yoshimasa Aotani
  • Patent number: 4839254
    Abstract: A photosensitive mixture contains a photosensitive compound and a polymeric binder which s a reaction product of a compound represented by the formula ##STR1## wherein X and Y are the same or different, and each denotes oxygen or sulfur,R.sub.1 and R.sub.2 are the same or different, and each denotes an unsubstituted or substituted alkyl, cycloalkyl or alkoxy radical containing from 1 to 6 carbon atoms; an unsubstituted or substituted aryl or aryloxy radical containing from 6 to 10 carbon atoms; or, together with the phosphorus atom, a 5- or 6-membered heterocyclic ring which is unsubstituted or substituted or which carries a fused benzene ring,with a polymer containing active hydrogen. The novel binders used in the mixture can be easily prepared and yield photosensitive layers of good developability and developer resistance.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: June 13, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Jerg Kleiner
  • Patent number: 4839256
    Abstract: Light-sensitive perfluoroalkyl group-containing 1,2-naphthoquinone diazide compounds and reproduction materials comprising a support and a light-sensitive layer containing such compounds useful in producing planographic printing plates for waterless printing. The 1,2-naphthoquinone diazide compounds correspond to the formula I. ##STR1## wherein Ar denotes a mononuclear to trinuclear aromatic radicalD is a 1,2-naphthoquinone-2-diazide-4-sulfonyl radical or a 1,2-naphthoquinone-2-diazide-5-sulfonyl radical,R.sub.F is a perfluoroalkyl radical having from 5 to 15 carbon atoms,W is a single bond or is selected from the group consisting of______________________________________ (CH.sub.2).sub.m COO (CH.sub.2).sub.m OOCCHR.sup.2O (CH.sub.2).sub.m OC.sub.o H.sub.2oCOO (CH.sub.2).sub.m OOC (CH.sub.2).sub.m OOCC.sub.o H.sub.2oCOO (CH.sub.2).sub.m SO.sub.2 NH (CH.sub.2).sub.m OOCCHCHCOO C.sub.6 H.sub.4 SO.sub.2 NH (CH.sub.2).sub.m CO (CH.sub.2).sub.m CONH (CH.sub.2).sub.m SO.sub.3 (CH.sub.2).sub.m OOCC.sub.o H.sub.
    Type: Grant
    Filed: August 21, 1987
    Date of Patent: June 13, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Werner H. Muller
  • Patent number: 4837124
    Abstract: Photoresist compositions suitable for deep UV and excimer laser lithography are disclosed that are mixtures of a photoacid and a polymer having imide residues to which acid labile groups are attached. These compositions provide high resolution, high contrast and high sensitivity in the deep UV (wavelength of 250-300 nm), mid-UV (wavelength of 300-350 nm) or conventional (wavelength of 350-450 nm) exposure bands. The compositions are also suitable for exposure at wavelengths commonly associated with excimer laser sources (248, 308 nm) or for exposure by X-radiation.In the compositions disclosed, the imide group ##STR1## can be blocked with certain groups, X, to form compounds containing the structure ##STR2## which have solubility properties different from the unblocked imide. These groups, X, can be cleaved by acid under the proper conditions to regenerate the unblocked imide.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: June 6, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Chengjiu Wu, Anne M. Mooring, Michael J. McFarland, Christopher E. Osuch, James T. Yardley
  • Patent number: 4837121
    Abstract: A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers ) to prepare a light-sensitive composition useful as a positive-working photoresist.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: June 6, 1989
    Assignee: Olin Hunt Specialty Products Inc.
    Inventors: Andrew J. Blakeney, Alfred T. Jeffries, III, Thomas R. Sarubbi
  • Patent number: 4835085
    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.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 30, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4828958
    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.
    Type: Grant
    Filed: March 9, 1987
    Date of Patent: May 9, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shuzi Hayase, Yasunobu Onishi, Rumiko Horiguchi
  • Patent number: 4822719
    Abstract: A radiation-sensitive mixture which contains(A) a polymer comprised of repeat units represented by the formula ##STR1## where R is a hydrogen or a halogen atom, a cyanide group or an alkyl group of 1-4 carbon atoms,R.sup.1, R.sup.2 are identical or different, and eachand R.sup.3 denotes a hydrogen or a halogen atom, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an acyl group, an aryloxy group, an aroyl group or aralkyl group,R.sup.4 is a hydrogen atom or a divalent organic group which is linked to another unit represented by formula (I),X denotes an oxygen atom or one of the groups NR.sup.8, OCH.sub.2 CHOHCH.sub.2 OCO, OCH.sub.2 CH.sub.2 O and OCH.sub.2 CH.sub.2 OCO, where R.sup.
    Type: Grant
    Filed: August 13, 1986
    Date of Patent: April 18, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Arnold Schneller, Ralf Schulze, Ju Sander, Kurt Erbes
  • Patent number: 4822716
    Abstract: The polysilanes and polysiloxanes of the present invention are polymers that contain silicon in the principal chain, and contain in the side chains alkaline soluble groups such as phenol-based hydroxy group and carboxyl group.One silicone resist material of the present invention comprises the polysilane or the polysiloxane in the above.Another silicone resist material of the present invention contains the above polysilane or polysiloxane, and an appropriate photosensitive agent.Still another silicone resist material of the present invention does not contain the above photosensitive agent, and in its stead, it contains a group that possesses photosensitive to ultraviolet rays or the like, via a siloxane bonding in the principal chain. As a substance with such photosensitivity, one may mention, for example, o-nitrobenzylsilyl groups that presents alkaline solubility when it is irradiated by ultraviolet rays.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: April 18, 1989
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Yasunobu Onishi, Shuji Hayase, Rumiko Horiguchi, Akiko Hirao
  • Patent number: 4820607
    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.
    Type: Grant
    Filed: August 14, 1986
    Date of Patent: April 11, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4818658
    Abstract: The subject invention involves reduction of light reflection into a photoresist coating over a reflective substrate by the use of a photoactive compound in a photoresist formulation that is the reaction product of a diazooxide and curcumin.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: April 4, 1989
    Assignee: Shipley Company Inc.
    Inventors: Robert L. Martin, M. Martha Rajaratnam, Pamela Turci
  • Patent number: 4816375
    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.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4812551
    Abstract: A novolak resin for a positive photoresist is provided herein, which resin is produced by the addition condensation reaction of a phenol with formaldehyde. This novolak resin has improved heat resistant and sensitivity properties and the thickness retention of the novolak resins are very high.
    Type: Grant
    Filed: November 9, 1987
    Date of Patent: March 14, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumio Oi, Haruyoshi Osaki, Akihiro Furuta, Yukikazu Uemura, Takao Ninomiya, Yasunori Uetani, Makoto Hanabata
  • Patent number: 4810613
    Abstract: A new monomer is used to prepare homo or copolymers containing blocked imide groups which are characterized by deblocking in two stages, first when acid catalyzed and thereafter in aqueous alkaline solutions. Such polymers are, therefore, especially useful in formulating positive photoresist cmpositions. The polymers are combined with a latent photoacid, which when exposed to actinic radiation removes the acid sensitive blocking moiety, preferably an acetal or ketal group, leaving a methylol group or substituted methylol group remaining attached to the nitrogen atom, which groups are subsequenctly removed by exposure to aqueous alkaline developing solutions, leaving only imide groups, ##STR1## The new monomer is a derivative of maleimide in which the imide hydrogen has been replaced with a methylol group, which is subsequently reacted to form an acetal or ketal. Preferred monomers include N-(2,4-dioxa-3,3-dimethylpentyl)-2H,5H-2,5-dioxopyrrole and related compounds.
    Type: Grant
    Filed: May 22, 1987
    Date of Patent: March 7, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Christopher E. Osuch, Michael J. McFarland
  • Patent number: 4806448
    Abstract: Compounds of formula I ##STR1## in conjunction with compounds that donate acid when exposed to actinic radiation, are suitable for use as positive photoresists. In formula I, R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, cycloalkyl, aralkyl or alkaryl, R.sup.3 to R.sup.8 are hydrogen or lower alkyl, X is --O-- or --NR.sup.9 --, where R.sup.9 is hydrogen or C.sub.1 -C.sub.4 alkyl n is 0 or 1, m is 2, 3 or 4 and Q is an organic radical of valency m.The photoresists are suitable for making printing formes, printed circuits, integrated circuits or silver-free photographic films.
    Type: Grant
    Filed: November 27, 1987
    Date of Patent: February 21, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Martin Roth
  • Patent number: 4804612
    Abstract: Although the positive-working photoresist composition comprises a phenolic novolac resin as the film-forming component and a known photosensitizing compound as in conventional compositions, the novolac resin is prepared from a specific mixture of two classes of phenolic compounds including, one, phenol, cresols and/or resorcinol and, the other, one or more of the phenolic compounds having a nucleus-substituting group selected from allyloxy, allyloxymethyl, allyl dimethyl silyl, 2-(allyl dimethyl silyl) ethoxy, cinnamoyl, acryloyl and methacryloyl groups. By virtue of this unique combination to give the phenolic moiety in the novolac resin, the photoresist composition has markedly improved heat resistance as well as stability against plasma in dry etching so that the composition can give a patterned photoresist layer with extreme fineness having high fidelity to the mask pattern.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: February 14, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shingo Asaumi, Hidekatsu Kohara, Hatsuyuki Tanaka, Toshimasa Nakayama
  • Patent number: 4797346
    Abstract: A light-sensitive composition for use in the preparation of positive-type light-sensitive lithographic printing plate which comprises an o-naphthoquinone diazide compound and novolak resin in which the novolak resin comprises two different novolak resins each being prepared by the polycondensation or co-polycondensation of an aldehyde with at least one compound selected from the group consisting of phenol, m-cresol, o-cresol and p-cresol.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: January 10, 1989
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Takeshi Yamamoto, Nobumasa Sasa, Miegi Nakano
  • Patent number: 4797348
    Abstract: A dually photosensitive composition useful as a photoresist in the manufacture of ICs and the like electronic devices, which is positively photosensitive by exposure to ultraviolet in a relatively small dose but negatively photosensitive by exposure to ultraviolet in a substantially larger dose than above or by exposure to far ultraviolet light, is obtained by admixing a positive-type photoresist material comprising a novolac resin and an o-naphthoquinone diazide compound with a bisazide compound such as 4,4'-diazidodiphenyl sulfide. The inventive photosensitive composition provides a possibility of developing an ingenious technique for patterning of a photoresist layer on the substrate such as a checkboard-like patterned layer by use of a photomask of a line-and-space pattern.
    Type: Grant
    Filed: February 17, 1988
    Date of Patent: January 10, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoichi Nakamura, Shirushi Yamamoto, Takashi Komine, Akira Yokota, Hisashi Nakane
  • Patent number: 4797345
    Abstract: Light-sensitive 1,2-naphthoquinone-2-diazide-4-sulfonic acid monoester of a cycloalkyl-substituted phenol corresponding to the formula: ##STR1## wherein n is from about 2 to about 10 and their use in light-sensitive mixtures (e.g. positive-working photoresist compositions) also containing alkali-soluble resins such as phenol-formaldehyde novolaks and cresol-formaldehyde novolaks as well as substrates coated therewith.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: January 10, 1989
    Assignee: Olin Hunt Specialty Products, Inc.
    Inventor: Alfred T. Jeffries, III
  • Patent number: 4792516
    Abstract: A photosensitive composition comprising (a) a photosensitive component such as an aromatic diazo compound or an aromatic azide, (b) a polymer and (c) a quaternary alkylammonium salt wherein each straight- or branched-chain alkyl group has 1 to 7 carbon atoms is suitable for producing a positive type or negative type photresist excellent in contrast and sensitivity in the microlithography of semiconductor elements.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: December 20, 1988
    Assignee: Hitachi Chemical Company
    Inventors: Minoru Toriumi, Hiroshi Shiraishi, Ryotaro Irie, Shigeru Koibuchi
  • Patent number: 4789619
    Abstract: A positive-working radiation-sensitive mixture is described that contains (a) a radiation-sensitive compound which forms a strong acid under the action of actinic radiation, (b) a compound with at least one C--O--C bond cleavable by acid, (c) a binder which is insoluble in water but soluble in aqueous-alkaline solutions, and (d) a polymethine dye. The polymethine dyes used are hemioxonol dyes or symmetrical cyanine dyes. In the light-sensitive mixture, these dyes effect high sensitization and high image sharpness contrast which, in addition, is substantially irreversible.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: December 6, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Joachim Knaul
  • Patent number: 4788127
    Abstract: A photoresist composition comprises a photosensitive compound and an interpolymer of a silicon-containing monomer and an hydroxystyrene. The resist composition exhibits superior thermal stability and dissolution rate and good resistance to an oxygen plasma etch.
    Type: Grant
    Filed: November 17, 1986
    Date of Patent: November 29, 1988
    Assignee: Eastman Kodak Company
    Inventors: David B. Bailey, Michael M. Feldman
  • Patent number: 4786577
    Abstract: A photo-solubilizable composition is disclosed, comprising (a) a compound capable of producing an acid upon being irradiated with actinic light rays, and (b) a compound containing at least one silyl ether group represented by formula (I) ##STR1## that is capable of being decomposed with an acid and at least one group selected from among a urethane group, a ureido group, an amido group, and an ester group, and, according to a preferred embodiment at least one hydrophilic group.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: November 22, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Akihiko Kamiya
  • Patent number: 4777111
    Abstract: This invention relates to a composition and method for enhancing the contrast of images of an underlying photolithographic layer. A photographic element, including a photoresist layer, is applied to a substrate. The photoresist layer contains a contrast-enhancing layer including at least one light-sensitive compound capable of producing acidic photoproducts upon exposure to actinic radiation, at least one indicator dye that changes color on exposure to acidic conditions and at least one polymeric binder soluble in water or weakly alkaline aqueous solutions. The photographic element is exposed to active radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer. The photographic element is exposed to actinic radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: October 11, 1988
    Assignee: Fairmount Chemical Company, Inc.
    Inventors: David B. Blumel, Albert S. Deutsch
  • Patent number: 4774171
    Abstract: Novel bis-1,2-naphthoquinone-2-diazide-sulfonic acid amides of secondary diamines, which amides are represented by the formula ##STR1## in which R is a straight-chain or branched, unsubstituted or hydroxyl-substituted alkyl, cycloalkyl or aralkyl radical which has 1 to 14 carbon atoms and which includes a carbon chain that can be interrupted by either oxygen atoms,R.sub.1 is an alkylene radical which has 2 to 12 carbon atoms and which includes a carbon chain that can be interrupted by ether oxygen atoms, or a mononuclear or polynuclear aralkylene radical which has 8 to 18 carbon atoms and which can, when it is a polynuclear radical, comprise aromatic members that are linked by a single bond, by --O--, --S--, --CO-- or --CR.sub.2 R.sub.3 --, --N[C.sub.1-3 -alkyl]CO-- or a C.sub.2-5 -alkyl group which can be interrupted by ether oxygen atoms, andR.sub.2 and R.sub.
    Type: Grant
    Filed: February 4, 1987
    Date of Patent: September 27, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Zahn, Gerhard Buhr
  • Patent number: 4772533
    Abstract: This invention relates to positive working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: September 20, 1988
    Assignee: American Hoechst Corporation
    Inventors: Stephan J. W. Platzer, Gabor I. Koletar, Richard L. Shadrach
  • Patent number: 4764450
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C--O--C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: December 29, 1986
    Date of Patent: August 16, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher