Polymeric Mixture Patents (Class 430/192)
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Patent number: 6030741Abstract: The present invention provides a positive resist composition and method capable of achieving a resist pattern whose photosensitivity is less variable relative to its thickness, which exhibits small thickness reduction even when the pattern is fine, is capable of coping with irregularities in the exposure value since it has a wide focal-depth range, and exhibits reduced size-deviation from the mask size. The positive resist composition comprises (A) an alkali-soluble resin, (B) a quinonediazide-group-containing compound, and (C) an organic solvent, wherein the ingredient (C) is a mixture solvent containing (i) 2-heptanone, (ii) ethyl lactate, and (iii) a high-boiling organic solvent having a boiling point of 200 to 350.degree. C. The above-described resist pattern can be formed by using the positive resist composition.Type: GrantFiled: August 28, 1997Date of Patent: February 29, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kousuke Doi, Takako Suzuki, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6020104Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymono-carboxylic 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: January 27, 1999Date of Patent: February 1, 2000Assignee: JSR CorporationInventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Patent number: 6013407Abstract: A positive resist composition is excellent in sensitivity, film loss after development, resolution, thermal-flow resistance, storage stability, exposure margin and focus margin and comprises in combination (A) an alkali-soluble phenol resin, (B) a quinonediazide sulfonate type photosensitive agent and (C) a phenolic compound, wherein the phenolic compound (C) is at least one phenolic compound selected from the group consisting of phenolic compounds (CX) having a structural unit represented by the following formula (I) and phenolic compounds (CD) having a structural unit represented by the following formula (II): ##STR1## wherein R.sup.1 to R.sup.3 are, independently of one another, a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkenyl group which may be substituted, an alkoxy group which may be substituted, or an aryl group which may be substituted, R.sup.4 to R.sup.Type: GrantFiled: July 8, 1997Date of Patent: January 11, 2000Assignee: Nippon Zeon Co., Ltd.Inventors: Shoji Kawata, Hiroshi Hayashi, Hirokazu Higashi, Takeyoshi Kato, Masahiro Nakamura
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Patent number: 6007961Abstract: A radiation-sensitive resin composition including an alkali soluble resin and a quinonediazide compound is provided. The quinonediazide compound has the formula (1), for example: ##STR1## wherein, R.sup.1 to R.sup.6 are an alkyl, cycloalkyl or aryl group; a and b are an integer of 1 to 3; D.sup.1 and D.sup.2 are independently a hydrogen atom or a 1,2-quinonediazidosulfonyl group, provided that at least one of D.sup.1 is a 1,2-quinonediazidosulfonyl group; A is a bonding such as single bond; and x and y are an integer of 0 to 2. The composition is suitable as a positive resist, which effectively restrains the occurrence of scum, and excellent in developability, pattern shape, sensitivity, resolution and focus latitude.Type: GrantFiled: December 10, 1997Date of Patent: December 28, 1999Assignee: JSR CorporationInventors: Katsumi Inomata, Masahiro Akiyama, Shin-ichiro Iwanaga, Akira Tsuji
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Patent number: 6001517Abstract: A positive photosensitive polymer composition, which comprises a thermosetting polymer precursor which can be cured through cyclodehydration upon heating, and a photosensitive cure accelerator which can be inactivated of its cure accelerating property by irradiation of light.Type: GrantFiled: October 29, 1997Date of Patent: December 14, 1999Assignee: Kabushiki Kaisha ToshibaInventor: Yoshiaki Kawamonzen
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Patent number: 5998084Abstract: A positive-working, radiation-sensitive recording material capable of being used for the production of planographic printing plates, comprising: an aluminum support and a radiation-sensitive layer coated thereon, whereinthe aluminum support has been grained in nitric acid, then cleaned in sulfuric acid, anodized in sulfuric acid, and subsequently hydrophilized with a compound comprising at least one unit with a phosphonic acid or phosphonate group; andthe radiation-sensitive layer comprisesa) a radiation-sensitive 1,2-naphthoquinone-2-diazide-4- or -5-sulfonic acid ester of a polycondensate having phenolic hydroxy groups, said polycondensate being obtained by reacting a phenolic compound with an aldehyde or ketone,b) a novolak or a polycondensation product obtained by reacting a polyphenol with an aldehyde or ketone, as an alkali-soluble resin,c) a vinyl-type polymer comprising at least one unit having a lateral hydroxyphenyl group,d) a clathrate-forming compound,e) a low-molecular weight compound which comprType: GrantFiled: November 15, 1996Date of Patent: December 7, 1999Assignee: Agfa-Gevaert N.V.Inventors: Andreas Elsaesser, Raimund Haas, Guenter Hultzsch, Peter Lehmann, Rudolf Neubauer, Rudolf Zertani
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Patent number: 5998567Abstract: A radiation-sensitive mixture which contains (a) a compound of the formula (I) ##STR1## where R.sup.1 is an optionally substituted alkyl radical, R.sup.2 is a hydrogen atom or an optionally substituted alkyl radical containing 1 to 4 carbon atoms, R.sup.3 is an n-valent, optionally polymeric aliphatic or aromatic radical and n is a number from 1 to 100; and b) a compound which forms a strong acid on exposure to actinic radiation.Type: GrantFiled: September 18, 1997Date of Patent: December 7, 1999Assignee: Clariant GmbHInventors: Mathias Eichhorn, Gerhard Buhr
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Patent number: 5994430Abstract: The present invention relates to an antireflective coating composition comprising a novel polymer in a solvent composition. The invention further comprises processes for using the antireflective coating composition in photolithography. The antireflective coating composition comprises a novel polymer and a solvent composition, where the novel polymer of the antireflective coating comprises at least one unit containing a dye that absorbs from about 180 nm to about 450 nm and at least one unit that contains no aromatic funtionality. The solvent may be organic, preferrably, a solvent of low toxicity, or it may be water, which may additionally contain other water miscible organic solvents.Type: GrantFiled: April 30, 1997Date of Patent: November 30, 1999Assignee: Clariant Finance BVI) LimitedInventors: Shuji Ding, Ping-Hung Lu, Dinesh N. Khanna, Jianhui Shan, Dana L. Durham, Ralph R. Dammel, M. Dalil Rahman
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Patent number: 5985507Abstract: A high thermal alkali-soluble novolak binder resin, comprising the addition-condensation reaction product of a phenolic mixture with at least one aldehyde source, the feedstock of the phenolic mixture for the reaction comprising:(1) about 25 to about 40 weight percent of the phenolic mixture being a monomer selected from meta-cresol 2,5-xylenol or the combination thereof;(2) about 50 to about 70 weight percent of the phenolic mixture being para-cresol; and(3) about 3 to about 20 weight percent of the phenolic mixture being acetamidophenol; all percentages based on the weight of total phenol monomer feedstock.The invention is also directed to a positive working photoresist made from the composition.Type: GrantFiled: February 18, 1998Date of Patent: November 16, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
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Patent number: 5981135Abstract: A positive acting photoresist composition (e.g., a monolayer dry film) which is strippable in aqueous alkaline solution comprises a photo acid generator and a UV-transparent resin binder system which allows efficient photo bleaching of the photoactive component. An acid functional cellulosic resin may be the only binder resin, an acidic acrylate resin being optional. The dry coating is flexible and may be used as an etch and plating resist.Type: GrantFiled: August 13, 1997Date of Patent: November 9, 1999Assignee: Morton International, Inc.Inventors: Thomas A. Koes, Grieg B. Beltramo
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Patent number: 5965320Abstract: A positive photoresist composition including an alkali-soluble resin and a photosensitive agent including 1,2-naphthoquinone-diazide group. A first composition wherein the photosensitive agent is an ester of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and alcohols or phenols, or a sulfonamide of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and organic amines.A second composition wherein the photosensitive agent comprises (a) an ester compound of 1,2-naphthoquinone-(2)-diazide-6-sulfonic acid and phenols and (b) an ester of 1,2-naphthoquinone-(2)-diazide-5-sulfonic acid and phenols and/or an ester of 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid and phenols.A third composition wherein the photosensitive agent is a product obtained by condensation of phenols with (a) 1,2-naphthoquinone-(2)-diazide-6-sulfonylhalide and (b) 1,2-naphthoquinone-(2)-diazide-5-sulfonylhalide and/or 1,2-naphthoquinone-(2)-diazide-4-sulfonylhalide.Type: GrantFiled: September 7, 1993Date of Patent: October 12, 1999Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Kazue Torimitsu, Yuko Urano, Hideo Kikuchi
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Patent number: 5958645Abstract: A radiation-sensitive resin composition comprising:(i) an alkali-soluble resin;(ii) a phenol compound represented by the following formula (1): ##STR1## wherein R.sub.1 to R.sub.4 each represent halogen, alkyl, alkoxyl, aryl, nitro, cyano, hydroxyalkyl, hydroxyalkoxyl or hydroxyl; a, b, c and d each represent an integer of 0 to 4 and satisfying 0.ltoreq.a+b.ltoreq.4 and 0.ltoreq.c+d.ltoreq.4, provided that when a+b is 1 and c+d is 1 at least one of R.sub.1 (or R.sub.2) and R.sub.3 (or R.sub.4) is alkyl, hydroxyalkyl or hydroxyalkoxyl; R.sub.5 to R.sub.10 each represent hydrogen, alkyl or aryl; and X.sub.1 and X.sub.2 each represent oxygen or sulfur atom; and(iii) a 1,2-quinonediazide compound. This composition has good resolution, sensitivity and developability, as well as has as a positive resist good focal latitude and heat resistance. The patterns formed have good shapes, and the composition may cause no fine particles during storage.Type: GrantFiled: August 27, 1997Date of Patent: September 28, 1999Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Kouichi Hirose, Masahiro Akiyama, Katsumi Inomata, Yoshiji Yumoto
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Patent number: 5958646Abstract: Disclosed are (i) a positive-working photosensitive composition containing (a) a polymer having at least 60 mol % structural units represented by formula (1): ##STR1## wherein A represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms; X represents --CO-- or --SO.sub.2 --; Y represents --CO--R.sub.1 or --SO.sub.2 --R.sub.1, where R.sub.1 represents an alkyl group, a substituted alkyl group wherein the substituent on the substituted alkyl group is a halogen atom, an aryl group, an amido group, an alkoxy group or an alkoxycarbonyl group, an unsubstituted aromatic group, or a substituted aromatic group wherein the substituent on the substituted aromatic group is a halogen atom, an alkyl group, an alkoxy group having 1 to 10 carbon atoms, an amido group or an aryl group, provided that at least one of X and Y contains --SO.sub.Type: GrantFiled: December 8, 1995Date of Patent: September 28, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Satoshi Takita, Keiji Akiyama, Yoshitaka Kawamura
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Patent number: 5955245Abstract: Disclosed is a method of forming a pattern on a substrate. A first solution is formed of an organic solvent and monomers of diamine and dianhydride. The monomers are polymerized to form a polyamic acid soluble in the organic solvent. About 20 to about 95% of the amic acid groups in the polyamic acid are imidized to form a partially imidized polyamic acid. A more concentrated solution of the partially imidized polyamic acid is formed. This can be accomplished by precipitating the partially imidized polyamic acid from the first solution and dissolving it in a second organic solvent to form a second solution. The second solution is applied to the substrate and the solvent is evaporated to form a coating of the partially imidized polyamic acid on the substrate. A portion of the coating is removed to form a pattern on the substrate and the remaining partially imidized polyamic acid is fully imidized on the substrate.Type: GrantFiled: October 12, 1993Date of Patent: September 21, 1999Assignee: Occidental Chemical CorporationInventor: Jin-O Choi
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Patent number: 5948587Abstract: Provided is a positive working photoresist composition comprising (A) an alkali-soluble novolak resin obtained by condensation reaction of a mixture of phenols, which are constituted of specified proportions of m-cresol and two kinds of specific phenols, with an aldehyde and having a Mw/Mn ratio of from 1.5 to 4.0 (wherein Mw stands for a weight-average molecular weight, and Mn stands for a number-average molecular weight); (B) a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic acid ester as a photosensitive material; and (C) a low molecular weight compound having from 12 to 50 carbon atoms per molecule and from 2 to 8 phenolic hydroxy groups per molecule.Type: GrantFiled: September 19, 1996Date of Patent: September 7, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Shiro Tan
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Patent number: 5945516Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.Type: GrantFiled: May 20, 1998Date of Patent: August 31, 1999Assignee: Shipley Company, L.L.C.Inventors: Harold F. Sandford, Anthony Zampini
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Patent number: 5942369Abstract: A positive photoresist composition including (A) 100 parts by weight of an alkali-soluble novolak resin, and based thereon; (B) 5 to 50 parts by weight of an alkali-soluble acrylic resin containing, as s, 10 to 80% by weight of a unit of a radical-polymerizable compound having an alcoholic hydroxyl group and 3 to 50% by weight of at least one of a unit of a radical-polymerizable compound having a carboxyl group and a unit of a radical-polymerizable compound having a phenolic hydroxyl group; (C) 5 to 100 parts by weight of a quinonediazide group-containing compound; and (D) a solvent, is provided. This composition has a good adhesion to substrates at the time of development and a good plating solution resistance and moreover can be well wetted with plating solutions, can be well developed with alkali developing solutions and can be well stripped from substrates at the resist unexposed areas, and is suited for the formation of thick films suitable as bump forming materials.Type: GrantFiled: January 27, 1998Date of Patent: August 24, 1999Assignee: JSR CorporationInventors: Toshiyuki Ota, Kimiyasu Sano, Masaru Ohta, Hozumi Sato
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Patent number: 5932389Abstract: This invention relates to alternating and block copolymer resins of uniform and controlled chain length and methods for preparing the same. The alternating copolymer resins are formed from the reaction of a bisoxymethylphenol, a reactive phenolic compound and a monooxymethylphenol. The alternating copolymer may then be further reacted with a second reactive compound in the presence of an aldehyde to form the substantially blocked copolymer. The resins of the invention are characterized by a low molecular weight distribution. The resins are useful for the formulation of high resolution photoresist materials.Type: GrantFiled: February 20, 1998Date of Patent: August 3, 1999Assignee: Shipley Company, L.L.C.Inventor: Anthony Zampini
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Patent number: 5932396Abstract: A resist composition is used to form a plating frame including a space having a section of up to 2 .mu.m in width and at least 4 .mu.m in depth. The resist composition contains as an alkali-soluble resin and a sensitizer a novolak resin obtained by substituting a hydrogen atom in a hydroxyl group in a novolak resin comprising at least one recurring unit represented by the following formula (1): ##STR1## wherein n is an integer of 1 to 4 and m is an integer of 0 to 3, and having a weight average molecular weight of 2,000 to 6,000 calculated as polystyrene by 0.12 to 0.22 moles per hydrogen atom of a 1,2-naphthoquinonediazidosulfonyl group.Type: GrantFiled: September 30, 1997Date of Patent: August 3, 1999Assignee: TDK CorporationInventor: Akifumi Kamijima
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Patent number: 5912102Abstract: A positive resist composition comprising an alkali-soluble phenolic resin, a photosensitive agent composed of a quinonediazide sulfonate of a specific polyhydroxy compound, and an aromatic compound having at least one phenolic hydroxyl group.Type: GrantFiled: June 26, 1997Date of Patent: June 15, 1999Assignee: Nippon Zeon Co., Ltd.Inventors: Shoji Kawata, Motofumi Kashiwagi, Teturyo Kusunoki, Masahiro Nakamura
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Patent number: 5876897Abstract: A light sensitive positive composition comprising an alkali soluble resin, a novel photoactive compound represented by the structure ##STR1## where, X is O, S or N--R', where R' is H, alkyl, substituted alkyl, aryl or aralkyl,Y is a connecting group such as SO.sub.2, CO, O or NR',Z is a carbon containing organic ballast moiety having a molecular weight greater than about 75 and can form a bond with the connecting group,R is independently H, alkyl, alkoxy, aryl, aralkyl, halo or fluoroalkyl,m=1-3, and n.gtoreq.1;and a solvent or mixture of solvents. The invention further comprises a process for imaging the composition of this invention to give positive image. The light sensitive composition is especially useful as a positive deep-uv photoresist.Type: GrantFiled: March 7, 1997Date of Patent: March 2, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Dana L. Durham, Ping-Hung Lu, Joseph E. Oberlander, Dinesh N. Khanna
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Patent number: 5876895Abstract: A photosenstive resin composition for color filter having excellent resolution, heat resistance and transparency, etc., characterized in that it contains a novolak resin having the recurring units such as those represented by the general formula (I): ##STR1## ?wherein R.sub.1 to R.sub.5 represent hydrogen, alkyl, etc., and R.sub.6 and R.sub.7 represent hydrogen, alkyl, etc., provided that ##STR2## is coordinated at the o- or p-position in relation to the --OH group! and having a molecular weight of about 1,000-50,000, a solvent and a dye or pigment.Type: GrantFiled: May 24, 1996Date of Patent: March 2, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
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Patent number: 5863700Abstract: The present invention provides a method for producing a water insoluble, aqueous alkali soluble novolak resins having consistent molecular weight and superior performance in photoresist composition, by isolating such novolak resin without high temperature distillation. A method is also provided for producing photoresist composition from such a novolak resin and for producing semiconductor devices using such a photoresist composition.Type: GrantFiled: September 29, 1997Date of Patent: January 26, 1999Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Ping-Hung Lu
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Patent number: 5861229Abstract: A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:X--.alpha.--H (I)wherein x is a group of the formula: ##STR1## and .alpha. is a divalent group which comprises a repeating unit of the formula: ##STR2## in which n is a number of not less than 1; a, b, c, d, e and f are the same or different and a number of 0-3, provided that d+f is not less than 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or an aryl group, which resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.Type: GrantFiled: September 22, 1992Date of Patent: January 19, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Haruyoshi Osaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
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Patent number: 5858605Abstract: A photoresist composition comprising an alkali soluble resin and the reaction product of an ortho-naphthoquinone diazide sulfonic acid ester and a vinyl ether. In use, the photoresist is characterized by having at least a portion of the hydroxyl groups on the alkali soluble resin reacted with the photoactive compound and then deblocked by acid generation.Type: GrantFiled: March 8, 1997Date of Patent: January 12, 1999Assignee: Shipley Company, L.L.C.Inventors: Roger F. Sinta, Daniel Y. Pai
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Patent number: 5858584Abstract: A highly reliable positive type photosensitive resin composition composed of diamine having a carboxyl group as a structural unit, which can be developed with an alkaline aqueous solution, comprising polyamic acid ester having hydrophobic group, o-quinonediazidesulfonyl amide compound, and/or o-quinonediazidesulfonyl amide sulfonic ester compound, and electronic devices using the same. A polyamide film having preferable positive type relief patterns, of which the unexposed portion is not corroded, can be obtained.Type: GrantFiled: May 16, 1997Date of Patent: January 12, 1999Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.Inventors: Yoshiaki Okabe, Takao Miwa, Yasunari Maekawa, Takumi Ueno, Geraldine Rames-Langlade, Mina Ishida
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Patent number: 5856058Abstract: Proposed is a novel chemical sensitization-type positive-working photoresist composition used for the photolithographic patterning works in the manufacture of semiconductor devices exhibiting an excellent halation-preventing effect in the patternwise exposure to light. The composition comprises, in addition to conventional ingredients including an acid-generating agent capable of releasing an acid by the irradiation with actinic rays and a resinous ingredient capable of being imparted with increased solubility in an aqueous alkaline developer solution in the presence of an acid, a unique halation inhibitor which is an esterification product between a specified phenolic compound and a naphthoquinone-1,2-diazide sulfonic acid.Type: GrantFiled: June 7, 1996Date of Patent: January 5, 1999Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kazufumi Sato, Kazuyuki Nitta, Akiyoshi Yamazaki, Yoshika Sakai, Toshimasa Nakayama
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Patent number: 5853948Abstract: A positive photoresist composition comprising (A) an alkali-soluble resin; (B) a quinonediazido group containing compound; and (C) at least one sulfonyl halide represented by the following general formula (I):R.sup.1 --SO.sub.2 --X (I)where R.sup.1 is an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group or a substituted aryl group; X is a halogen atom, as well as a multilayer resist material using this composition. Very fine (<0.4 .mu.m) resist patterns can be formed that have high feature or edge integrity, that provide good contrast between exposed and unexposed areas after development and that assure a wider margin of exposure, better depth-of-focus characteristics and sharper cross-sectional profiles.Type: GrantFiled: October 29, 1997Date of Patent: December 29, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Atsushi Sawano, Junichi Mizuta, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 5853953Abstract: The invention provides novel polymers and photoresist compositions that comprise a photoactive component and use such polymers as a resin binder component. The polymers of the invention in general comprise at least one repeating unit that includes a moiety that has a high carbon content, and preferably is an aromatic group. Preferred polymers of the invention comprise at least one repeating unit that includes a moiety that is an extended aromatic ring, or polycyclic aromatic ring system containing 2 or more rings, preferably at least two of the rings being fused, and from about 3 to 8 ring members in each ring. Photoresists of the invention include both positive-acting and negative-acting compositions and contain a resin binder component that comprises the described polymer.Type: GrantFiled: September 6, 1996Date of Patent: December 29, 1998Assignee: Shipley Company, L.L.C.Inventor: Jacque H. Georger, Jr.
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Patent number: 5853949Abstract: Provided are a method of synthesizing a highly pure polyphenol compound, which comprises (i) introducing at least one --CHRNR'R" group onto aromatic ring(s) of a phenol compound having from one to ten aromatic ring(s), wherein R represents a hydrogen atom, an alkyl group which may contain a hetero atom, a cycloalkyl group which may contain a hetero atom, an aralkyl group which may contain a hetero atom, or an aryl group, and R' and R", which may be the same or different, each represents an alkyl group which may contain a hetero atom, a cycloalkyl group which may contain a hetero atom, an aralkyl group which may contain a hetero atom, or an aryl group, and R' and R" may combine with each other to form a ring, (ii) converting the --CHRNR'R" group into a --CHRA group via one to three steps, wherein A represents a hydroxyl group, an alkoxy group, an acyloxy group, a halogen atom, a quaternary ammonium salt or a sulfonyloxy group, and (iii) condensing the thus converted phenol compound and a phenol compound, and aType: GrantFiled: May 31, 1996Date of Patent: December 29, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Makoto Momota
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Patent number: 5853947Abstract: A photosensitive positive working photosensitive composition suitable for use as a photoresist, which comprises an admixture of at least one water insoluble, aqueous alkali soluble, film forming novolak resin; at least one o-diazonaphthoquinone photosensitizer; and a photoresist solvent mixture comprising a propylene glycol alkyl ether acetate and 3-methyl-3-methoxy butanol and process for producing such a composition.Type: GrantFiled: December 21, 1995Date of Patent: December 29, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Stanley F. Wanat, M. Dalil Rahman, Dinesh N. Khanna, Daniel P. Aubin, Sunit S. Dixit
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Patent number: 5849457Abstract: A positive-working resist composition comprising (A) a quinonediazide compound, (B) an alkali-soluble resin, and (C) a solvent system comprising 2-heptanone, ethyl lactate and .gamma.-butylactone in which the quinonediazide compound exhibits a very high solubility and which characteristics such as sensitivity, profile and coatability are excellent.Type: GrantFiled: October 24, 1997Date of Patent: December 15, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuhiko Namba, Kaoru Tatekawa, Hiroshi Moriuma, Yasunori Uetani
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Patent number: 5849461Abstract: In a chemically amplified positive resist composition comprising an organic solvent, an acid labile group-protected resin and a photoacid generator, a compound having a weight average molecular weight of 100-1,000 and at least two phenolic hydroxyl groups in a molecule wherein the hydrogen atom of the phenolic hydroxyl group is partially replaced by an acid labile group in an overall average proportion of 10-80% is blended as a dissolution controller. The resist composition is highly sensitive to actinic radiation, has improved sensitivity and resolution, and is suitable for use in a fine patterning technique and commercially acceptable.Type: GrantFiled: July 19, 1996Date of Patent: December 15, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Shigehiro Nagura, Kiyoshi Motomi, Takeshi Nagata, Toshinobu Ishihara
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Patent number: 5846690Abstract: A radiation-sensitive composition is disclosed which includes (a) a binder insoluble in water but soluble in or capable of being swelled in an aqueous alkali solution, (b) a dissolution inhibitor composed of (b1) a poly(N,O-acetal) having a general formula: ##STR1## wherein R.sup.3 is alkyl or substituted or unsubstituted aryl, R.sup.4 is a divalent group selected from alkylene, cycloalkylene, alkene or alkyne, R.sup.5 is alkyl, alkene, alkyne or cycloalkyl, X is --OCO--, --CO-- or --NHCO--, and p is a number not less than 1, and/or (b2) a phenol compound having a hydroxyl group which is protected by a group which can be cleaved in the presence of an acid, (c) a photosensitive compound capable of generating an acid when exposed to an active radiation, (d) a base capable of being decomposed when exposed to an active radiation to form a neutral compound derived therefrom, (e) a plasticizer, and (f) a solvent.Type: GrantFiled: March 14, 1996Date of Patent: December 8, 1998Assignee: Hoechst Japan LimitedInventors: Munirathna Padmanaban, Yoshiaki Kinoshita, Hiroshi Okazaki, Seiya Masuda, Natsumi Kawasaki, Satoru Funato, Georg Pawlowski
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Patent number: 5843616Abstract: A positive resist composition sensitive to radiations such as ultraviolet rays, far ultraviolet rays, which comprises;an o-quinonediazide compound; anda novolac resin(1) obtained by allowing an aromatic aldehyde of the formula(I) ##STR1## wherein R.sub.4 to R.sub.6 represents hydrogen, alkyl, cycloalkyl, alkoxy, alkenyl or aryl, k'0 represents an integer not smaller than 0 and p represents 1, 2 or 3, to react with a phenol compound of the formula (II) ##STR2## wherein R.sub.7 to R.sub.9 represents hydrogen, hydroxy, alkyl, cycloalkyl, alkoxy, alkenyl or aryl, provided that at least one of R.sub.7 to R.sub.9 is cycloalkyl having 6 or less carbon atoms, in the presence of an acid catalyst to obtain a reaction product(1) containing low molecular weight ingredients;and, then, allowing the reaction product(1) to further react with a phenol compound(1) and formaldehyde.Type: GrantFiled: April 10, 1995Date of Patent: December 1, 1998Assignee: Sumitomo Chemical Company, Ltd.Inventors: Kunishige Edamatsu, Yuji Yoshida, Kazuhiko Hashimoto, Haruyoshi Osaki
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Patent number: 5840467Abstract: Disclosed is an image recording material which comprises a binder, a substance capable of generating heat by the absorption of light and a heat decomposable substance capable of substantially lowering the solubility of the binder when the substance is in an undecomposed state.Type: GrantFiled: October 28, 1996Date of Patent: November 24, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Katsuji Kitatani, Keitaro Aoshima, Yuichi Shiraishi, Kazuto Kunita, Hiroaki Yokoya
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Patent number: 5837417Abstract: Process for producing a photosensitizer comprising a diazo ester of a p-cresol oligomer where at least one of the hydroxy groups on the p-cresol ring has been esterified with diazo-sulfonyl chloride comprising from about 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 photosensitive 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: December 30, 1994Date of Patent: November 17, 1998Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Dinesh N. Khanna, Daniel Aubin, Douglas McKenzie
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Patent number: 5827634Abstract: The invention comprises an acid hardened resist system consisting of a resin binder having acid labile blocking groups and inert blocking groups and a photoacid generator. The inclusion of inert blocking groups on the resin improves shelf life without deleteriously affecting photolithographic properties of the resist.Type: GrantFiled: March 12, 1997Date of Patent: October 27, 1998Assignee: Shipley Company, L.L.C.Inventors: James W. Thackeray, Roger F. Sinta, Mark D. Denison, Sheri L. Ablaza
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Patent number: 5821345Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound. The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.Type: GrantFiled: March 12, 1996Date of Patent: October 13, 1998Assignee: Shipley Company, L.L.C.Inventors: Harold F. Sandford, Anthony Zampini
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Patent number: 5814433Abstract: The invention provides a process for removing unwanted photoresist material from the periphery of a photoresist-coated substrate using a solvent composition of ethyl lactate and N-methyl pyrollidone, where the amount of N-methyl pyrollidone ranges from about 3% to about 20% by weight of the total composition, and where the solvent composition has a flash point of greater than 100.degree. F. (38.degree. C.), has an odor threshold value greater than 5000, is effective as both a backside and topside edge bead remover and can effectively remove the edge bead from an unbaked or baked photoresist film.Type: GrantFiled: April 3, 1997Date of Patent: September 29, 1998Assignee: Clariant Finance (BVI) LimitedInventors: William C. Nelson, Octavia Lehar
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Patent number: 5807947Abstract: A polymer of (a) an unsubstituted 4-hydroxystyrene monomer and (b) a substituted 4-hydroxystyrene monomer of the formula ##STR1## wherein A, B, C, and D are independently H or C.sub.1 to C.sub.4 alkyl wherein at least one of B and D is C.sub.1 to C.sub.4 alkyl; and wherein said copolymer has a molecular weight of from about 800 to about 100,000; and wherein the mol ratio of monomer (a) to monomer (b) ranges from about 3:1 to about 1:3.Type: GrantFiled: July 20, 1994Date of Patent: September 15, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Richard Vicari, Douglas J. Gordon, William D. Hinsberg, Dennis R. McKean, Carlton G. Willson, Ralph Dammel
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Patent number: 5807656Abstract: A polyhydroxy compound represented by the following formula (I): ##STR1## and a positive resist composition which comprises an alkali-soluble resin, a quinonediazide sulfonic acid ester, and a polyhydroxy compound of formula (I) or a polyhydroxy compound represented by the following formula (C): ##STR2## which is satisfactory in properties such as sensitivity, resolution, .tau.-value and peeling off resistance.Type: GrantFiled: September 4, 1996Date of Patent: September 15, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Haruyoshi Osaki, Yasunori Uetani, Yoshiyuki Takata
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Patent number: 5798201Abstract: A radiation sensitive resin composition containing an alkali soluble resin and a 1,2-quinonediazide compound of a polyphenol or a radiation sensitive resin composition containing an alkali soluble resin and a 1,2-quinonediazide compound and a polyphenol compound.Type: GrantFiled: July 2, 1997Date of Patent: August 25, 1998Assignees: Japan Synthetic Rubber Co., Ltd., Arakawa Chemical Industries, Ltd.Inventors: Katsumi Inomata, Nasahiro Akiyama, Toshiyuki Ota, Akira Tsuji
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Patent number: 5792586Abstract: The present invention provides a positive photoresist composition comprising a 1,2-naphthoquinonediazide compound and a novolac resin obtained through a condensation reaction between an aldehyde compound and a phenol compound represented by the following general formula (I): ##STR1## wherein R.sub.5, R.sub.6 and R.sub.7 each independently represents hydrogen atom, hydroxyl group or alkyl, cycloalkyl, alkoxy or alkenyl group having 6 or less carbon atoms or aryl group, provided that at least one of R.sub.5, R.sub.6 and R.sub.7 represents a cycloalkyl group having 6 or less carbon atoms. The composition of the present invention is excellent in the balance between properties such as sensitivity, resolution, heat resistance, profile, depth of focus, etc. and free from scum.Type: GrantFiled: November 3, 1994Date of Patent: August 11, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuhiko Hashimoto, Haruyoshi Osaki, Yasunori Uetani
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Patent number: 5792585Abstract: A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, 1, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: March 25, 1994Date of Patent: August 11, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
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Patent number: 5783355Abstract: A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, 1, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: June 14, 1995Date of Patent: July 21, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
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Patent number: 5776652Abstract: The invention relates to aromatic or heteroaromatic mono- or bis-diazonium 1,1,2,3,3,3-hexafluoro-propanesulfonates. They are employed in positive-working or negative-working radiation-sensitive mixtures which are used for coating radiation-sensitive recording material.Type: GrantFiled: October 14, 1997Date of Patent: July 7, 1998Assignee: Agfa-Gevaert AGInventors: Mathias Eichhorn, Gerhard Buhr
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Patent number: 5773192Abstract: Disclosed are an organic silicon compound having a repeating unit represented by general formula (I) shown below, a resist, a thermal polymerization composition and a photopolymerization composition containing the organic silicon compound, ##STR1## wherein R.sup.1 is a t-butyl group or a pyranyl group, R.sup.2 is an hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 1 to 24 carbon atoms, or a substituted or unsubstituted aralkyl having 7 to 24 carbon atoms, R.sup.3 is a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms or an alkoxyl group, and k represents an integer from 0 to 4.Type: GrantFiled: February 3, 1997Date of Patent: June 30, 1998Assignee: Kabushiki Kaisha ToshibaInventors: Shinji Murai, Yoshihiko Nakano, Ken Uchida, Shuji Hayase
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Patent number: 5763135Abstract: A light-sensitive positive photoresist composition containing a film forming resin, a photoactive compound, a solvent, and an arylhydrazo dye. The dyed photoresist reduces the linewidth variation of the resist pattern on a reflective substrate while giving good lithographic performance.Type: GrantFiled: September 30, 1996Date of Patent: June 9, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Shuji Ding, Ping-Hung Lu, Dinesh N. Khanna, Anthony J. Corso
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Patent number: 5759736Abstract: A photoresist composition comprising an alkali-soluble resin (A) and a radiation sensitive compound (B), as main components, which further contains a compound (C) of the following formula (I): ##STR1## wherein each of R.sup.1 to R.sup.4 which are independent of one another, is a hydrophobic substituent or a hydrogen atom, provided that all of R.sup.1 to R.sup.4 are not simultaneously hydrogen atoms, and each of a to d which are independent of one another, is an integer of from 1 to 5, and when any one of R.sup.1 to R.sup.4 is present in a plurality, the plurality of such any one of R.sup.1 to R.sup.4 may be the same or different.Type: GrantFiled: April 1, 1997Date of Patent: June 2, 1998Assignee: Mitsubishi Chemical CorporationInventors: Mineo Nishi, Koji Nakano, Tadashi Kusumoto, Yasuhiro Kawase