Polymeric Quinone Diazide Patents (Class 430/190)
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Patent number: 6140019Abstract: A radiation sensitive composition comprising (A) a colorant containing a quinacridone pigment, a mixture of an isoindolinone pigment and a yellow organic pigment or a mixture of copper phthalocyanine blue and a green pigment, (B) an alkali-soluble resin, (C) a polyfunctional monomer and (D) a photopolymerization initiator. The composition is useful for production of an additive or subtractive color filter which is used in a reflection-type color liquid crystal display device.Type: GrantFiled: July 23, 1998Date of Patent: October 31, 2000Assignee: JSR CorporationInventors: Kouichi Sakurai, Hiroaki Nemoto, Atsushi Kumano
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Patent number: 6127086Abstract: A positive photosensitive resin composition comprising (a) a silane diol such as diarylsilane diol or dialkylsilane diol, (b) one or more capped polybenzoxazole precursors having the structure: ##STR1## wherein Ar.sub.1 is a tetravalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Ar.sub.2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar.sub.3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof;Z is one of the following groups: ##STR2## x is 10 to 1000; y is 0 to 900; and b is 0.10 to 350; (c) a photosensitive agent, and (d) a solvent. The composition optionally includes an adhesion promoter, leveling agent, or mixtures thereof.Type: GrantFiled: September 24, 1999Date of Patent: October 3, 2000Assignee: Arch Specialty Chemicals, Inc.Inventors: Pamela J. Waterson, Ahmad Naiini, Steve Lien-Chung Hsu, William D. Weber
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Patent number: 6117610Abstract: An infrared imaging composition contains two essential components, a non-basic infrared radiation absorbing material (such as carbon black), and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in positive-working or negative-working imaging elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.Type: GrantFiled: August 8, 1997Date of Patent: September 12, 2000Assignee: Kodak Polychrome Graphics LLCInventors: Eugene L. Sheriff, Paul R. West, Jeffery A. Gurney, Thap DoMinh
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Patent number: 6074797Abstract: The present invention relates to a precursor of waterless planographic printing plates, in which at least a photosensitive layer and a silicone rubber layer are laminated on a substrate in this order, characterized in that said photosensitive layer contains a quinonediazide group-containing polyurethane resin and furthermore, preferably, contains a light-heat converting material.The present invention can provide a precursor of waterless planographic printing plates, which is improved in both image reproducibility and printing durability, and which can be applied to both the method of obtaining a waterless planographic printing plate by ordinary image exposure and the method of obtaining a waterless planographic printing plate by laser irradiation.Type: GrantFiled: February 23, 1999Date of Patent: June 13, 2000Assignee: Toray Industries, Inc.Inventors: Mitsuru Suezawa, Akihiro Iihara, Norimasa Ikeda
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Patent number: 6060217Abstract: A method for directly imaging a lithographic printing surface using infrared radiation without the requirement of pre- or post-UV-light exposure, or heat treatment employs a printing plate which contains a support with a hydrophilic surface overcoated with an imaging layer. The imaging layer contains at least one polymer having bonded pendent groups which are hydroxy, carboxylic acid, tert-butyl-oxycarbonyl, sulfonamide, amide, nitrile, urea, or combinations thereof; as well as an infrared absorbing compound. The imaging layer may contain a second polymer which has bonded pendent groups which are 1,2-napthoquinone diazide, hydroxy, carboxylic acid, sulfonamide, hydroxymethyl amide, alkoxymethyl amide, nitrile, maleimide, urea, or combinations thereof. The imaging layer may also contain a visible absorption dye, a solubility inhibiting agent, or both.Type: GrantFiled: September 2, 1997Date of Patent: May 9, 2000Assignee: Kodak Polychrome Graphics LLCInventors: My T. Nguyen, Nishith Merchant, Ken-Ichi Shimazu, S. Peter Pappas, Robert Hallman, Jerome Philip Kesselman, Celin Savariar-Hauck, Gerhard Hauck, Hans-Joachim Timpe, Omkar J. Natu, Ajay Shah
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Patent number: 6010816Abstract: Disclosed is an aluminum alloy support for a planographic printing plate, wherein the sodium content of the support is 0.005 to 0.040 weight %.Type: GrantFiled: December 30, 1997Date of Patent: January 4, 2000Assignee: Konica CorporationInventors: Kazuyuki Nishio, Takahiro Mori
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Patent number: 6004705Abstract: A ceramics green sheet which is suitably used for producing sintered ceramics substrates and the like is disclosed. The ceramics green sheet according to the present invention includes a ceramics powder, a photoinitiator, a UV absorber such as photoinitiation inhibitor organic dyes and inorganic powders, and a photosensitive resin composition. The ceramics green sheet according to the present invention has an advantage that via holes and through holes may be very easily formed with high precision, and fine holes may be formed reliably and inexpensively.Type: GrantFiled: July 22, 1996Date of Patent: December 21, 1999Assignee: Toray Industries, Inc.Inventors: Takaki Masaki, Takao Kitagawa, Akiko Yoshimura, Keiji Iwanaga
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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: 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: 5939511Abstract: The invention is directed to purification of phenolic resins and to a process for preparing an organic photoresist coating composition. The process comprises reacting one or more phenols to form a crude phenolic resin. The crude phenolic resin formed is then separated from its reaction mixture and dissolved in an aqueous insoluble organic solvent in an organic solvent that is a solvent for the photoresist coating composition. The solution so formed is then mixed with an aqueous phase to extract water soluble impurities from the resin solution into the aqueous phase. Finally, the purified resin solution is further diluted with additional photoresist solvent.Type: GrantFiled: April 8, 1998Date of Patent: August 17, 1999Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Suzanne M. Coley
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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: 5866295Abstract: The present invention relates to novel photosensitive quinolone compounds, specifically novel 3-diazo 2,4-quinolinedione compounds, that may be used in a variety of applications, such as, photosensitive coating compositions, pharmaceuticals, agricultural, amongst others. The invention further relates to a process for making the novel photosensitive 3-diazo 2,4-quinolinedione compounds. These compounds are particularity useful as a photoactive component in a positive working photoresist composition, particularity for use as a deep ultraviolet (UV) photoresist.Type: GrantFiled: March 7, 1997Date of Patent: February 2, 1999Assignee: Clariant Finance (BVI) LimitedInventors: Joseph E. Oberlander, Dana L. Durham, Dinesh N. Khanna
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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: 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: 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: 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
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Patent number: 5728504Abstract: A positive photoresist composition comprising (A) an alkali-soluble resin and (B) a light-sensitive component comprising at least one compound represented by the following general formula (I): ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each independently a hydrogen atom, an alkyl group having 1-3 carbon atoms or an alkoxy group having 1-3 carbon atoms; R.sup.4 is a hydrogen atom or an alkyl group having 1-3 carbon atoms; a, b and c are an integer of 1-3; l, m and n are an integer of 1-3, in which at least part of the hydroxyl groups present are esterified with a quinonediazidosulfonic acid and a sulfonic acid which has a group represented by the following formula (II):--SO.sub.2 --R.sup.5 (II)where R.sup.Type: GrantFiled: May 23, 1996Date of Patent: March 17, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroshi Hosoda, Satoshi Niikura, Atsushi Sawano, Tatsuya Hashiguchi, Kazuyuki Nitta, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 5723254Abstract: The invention relates to a positive-acting photoresist composition containing a mixture of photoactive compounds. One component of the mixture is the esterification product of an o-quinonediazide sulfonyl compound with a phenolic resin. Another component of the mixture is the esterification product of an o-quinonediazide sulfonyl compound with a low molecular weight phenol having from one to three aryl groups and from one to three hydroxyl groups. A third photoactive component which may be present in the formulation is the esterification product of an o-quinonediazide sulfonyl compound with a relative high molecular weight, polyhydric, polynuclear phenol.Type: GrantFiled: September 4, 1996Date of Patent: March 3, 1998Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Peter Trefonas, III, Pamela Turci, Catherine C. Meister, Gerald C. Vizvary
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Patent number: 5705308Abstract: An infrared imaging composition contains two essential components, namely an infrared absorbing compound, and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in photosensitive elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.Type: GrantFiled: September 30, 1996Date of Patent: January 6, 1998Assignee: Eastman Kodak CompanyInventors: Paul Richard West, Eugene Lynn Sheriff, Jeffrey Allen Gurney, Ralph Scott Schneebeli, Thomas Robert Jordan, Gary Roger Miller
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Patent number: 5695906Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide-type photosensitive compound and a solvent, wherein the photosensitive compound comprises 1 a quinonediazide sulfonate of a novolak resin (A) of the following formula (i) having a weight average molecular weight of from 600 to 2,200 or a novolak resin (B) of the following formula (ii) having a weight average molecular weight of from 600 to 2,200, and 2 a quinonediazide sulfonate of a hydroxybenzophenone (C) of the following formula (iii): ##STR1## wherein each of R.sup.1 and R.sup.4 is an alkyl group, R.sup.2 is an alkyl group or an aryl group, R.sup.3 is a hydrogen atom or an alkyl group, each of u and v is an integer of from 0 to 3, provided that when each of R.sup.1 to R.sup.4 is present in a plurality, the plurality of each of R.sup.1 to R.sup.4 may be the same or different, and each of k and l is a number of at least 0, provided that k:l=1:9 to 10:0; ##STR2## wherein R.sup.Type: GrantFiled: October 28, 1994Date of Patent: December 9, 1997Assignee: Mitsubishi Chemical CorporationInventors: Mineo Nishi, Koji Nakano, Keisuke Nakano, Iwao Matsuo
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Patent number: 5660967Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide type photosensitive compound and a solvent, in which the quinonediazide type photosensitive compound contains a quinonediazide sulfonic acid ester of a polycondensate (d) of at least one phenolic compound (a) of the formula (A) with at least one hydroxy aromatic aldehydes (b) of the formula (B) and at least one carbonyl compounds (c) of the formula (C), and the mixing ratio ((b)/(c) mol ratio) of the hydroxy aromatic aldehydes (b)/the carbonyl compounds (c) is from 1/99 to 99/1, and the polycondensate (d) has a weight average molecular weight of from 600 to 2,000 in terms of polystyrene calculation: ##STR1## (wherein R.sup.1 is an alkyl group having a carbon number of from 1 to 4, an alkoxy group having a carbon number of from 1 to 4 or a hydroxyl group, R.sup.2 is an alkyl group having a carbon number of from 1 to 4 or an alkoxy group having a carbon number of from 1 to 4, R.sup.3 and R.sup.Type: GrantFiled: December 27, 1995Date of Patent: August 26, 1997Assignee: Mitsubishi Chemical CorporationInventors: Mineo Nishi, Koji Nakano, Yoshihiro Takada
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Patent number: 5645969Abstract: A photosensitive composition comprising a quinonediazide compound and a binder resin, wherein said resin is a resin obtained by condensing a phenol component comprising the following (1) to (3), and an aldehyde or a ketone, and X.gtoreq.0.57, where X=A/B, where A is an integrated value of peaks from 23.0 to 31.0 ppm, and B is an integrated value of peaks from 23.0 to 37.0 ppm, in the .sup.Type: GrantFiled: December 21, 1995Date of Patent: July 8, 1997Assignees: Mitsubishi Chemical Corporation, Konica CorporationInventors: Fumiyuki Matsuo, Daisuke Kanazawa, Mitsuru Sasaki, Shinichi Matsubara, Katsuhiko Higashino, Toshiaki Yokoo
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Patent number: 5641604Abstract: A photoresist composition comprising an alkali soluble resin and an ortho-naphthoquinone diazide sulfonic acid ester of a polyhydroxy alcohol. The photoresist is characterized by having at least a portion of its free hydroxyl groups on the photoactive compound blocked with an acid labile blocking group that generates a hydroxide upon cleavage.Type: GrantFiled: January 4, 1996Date of Patent: June 24, 1997Assignee: Shipley Company, L.L.C.Inventors: Roger F. Sinta, Daniel Y. Pai, Timothy G. Adams
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Patent number: 5639587Abstract: A positive photoresist composition is disclosed, which comprises an alkali-soluble resin, at least one of 1,2-naphthoquinonediazidesulfonic monoesters of specific polyhydroxy compounds, and at least one of 1,2-naphthoquinonediazidesulfonic ester of specific polyhydroxy compounds. The positive photoresist composition exhibits remarkably improved sensitivity and resolution, and broad development latitude regardless of the film thickness, and further, low film thickness dependence of resist performances.Type: GrantFiled: March 14, 1996Date of Patent: June 17, 1997Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Koji Shirakawa, Shinji Sakaguchi
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Patent number: 5635329Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide-type photosensitive compound and a solvent, wherein the alkali-soluble resin is a polycondensation product of 1 at least one phenolic compound (A) of the following formula (A) with 2 formaldehyde (a) and at least one carbonyl compound (b) of the following formula (B), in which the mixing ratio of the formaldehyde (a) to the carbonyl compound (b) is within a range of from 1/99 to 99/1 in terms of the molar ratio of (a)/(b), and the alkaline soluble resin has partial structures of the following formula (C), in which the weight ratio of repeating units (.beta.) wherein m is from 1 to 5, to repeating units (.alpha.) wherein m is 0, i.e. the weight ratio of (.beta.)/(.alpha.), is at most 0.25: ##STR1## wherein R.sup.1 is a group of the formula R.sup.2, OR.sup.3, COOR.sup.4 or CH.sub.2 COOR.sup.5, wherein R.sup.2 is a C.sub.1-4 alkyl group, each of R.sup.3, R.sup.4 and R.sup.Type: GrantFiled: December 20, 1994Date of Patent: June 3, 1997Assignee: Mitsubishi Chemical CorporationInventors: Mineo Nishi, Koji Nakano, Makoto Ikemoto
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Patent number: 5594098Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions, utilizing treated ion exchange resins. A method is also provided for producing photoresist composition having a very low level of metal ions from such novolak resins and for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: July 11, 1994Date of Patent: January 14, 1997Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5585225Abstract: A lithographic coating and method of framing a lithographic image are disclosed. The method comprises coating at least a portion of a surface of an article with a radiation-crosslinkable polymer, and exposing the coated surface to a pattern of radiation to crosslink the polymer in a lithographic image. The functionalized polymer is a copolymer of an isoolefin of 4 to 7 carbon atoms and para-alkylstyrene, wherein the para-alkylstyrene is functionalized with a radiation reactive group at the para-alkyl group of the para-alkylstyrene.Type: GrantFiled: October 27, 1994Date of Patent: December 17, 1996Assignee: Exxon Chemical Patents Inc.Inventors: Jay D. Audett, Kenneth O. McElrath
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Patent number: 5543263Abstract: The present invention provides methods for producing photoresist compositions having a very low level of metal ions, utilizing specially treated ion exchange resins. A method is also provided for producing semiconductor devices using such photoresist compositions.Type: GrantFiled: June 17, 1994Date of Patent: August 6, 1996Assignee: Hoechst Celanese CorporationInventors: M. Dalil Rahman, Dana L. Durham
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Patent number: 5532107Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and a photosensitive agent, characterized in that the positive resist composition contains, as the photosensitive agent, the quinonediazide sulfonate of at least one of phenolic compounds represented by the following general formulae (I) and (II): ##STR1## wherein R.sub.1 through R.sub.4 mean individually a hydrogen or halogen atom, a hydroxyl group, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.5 denotes a hydrogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or an aryl group with the proviso that the number of hydroxyl groups is 3 or 4; and ##STR2## wherein R.sub.6 through R.sub.9 mean individually a hydrogen or halogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.Type: GrantFiled: April 13, 1994Date of Patent: July 2, 1996Assignee: Nippon Zeon Co., Ltd.Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
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Patent number: 5529880Abstract: A photoresist that is a mixture of the esterification product of an o-quinonediazide compound and a novolak resin and a high molecular weight phenol having from 2 to 5 phenolic groups and at least 4 diazo naphthoquinone groups. The extent of esterification of the novolak resin is up to 20 percent of the hydroxyl groups and the degree of esterification of the phenol is at least 50 percent of the phenolic hydroxyl groups. The preferred novolak resins are the aromatic novolak resin that are the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde, each alone or in the presence of a reactive phenol.Type: GrantFiled: March 29, 1995Date of Patent: June 25, 1996Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Peter Trefonas, III
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Patent number: 5523396Abstract: A process for synthesizing a quinonediazide ester is disclosed in which the esterification reaction of a polyhydroxy compound with 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonyl chloride is carried out in the presence of a base catalyst comprising a basic compound represented by formula (I) or (II): ##STR1## wherein R.sub.1 to R.sub.15 are defined in the disclosure. A positive working photoresist containing the ester is also disclosed. The process is capable of highly selectively yielding the desired photosensitive material containing specific unreacted hydroxyl group(s). The photoresist has high resolving power with reduced film thickness dependence of the resolving power, is less apt to leave a development residue, and has excellent storage stability for prolonged period of time.Type: GrantFiled: September 21, 1995Date of Patent: June 4, 1996Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Yasumasa Kawabe, Toshiaki Aoai
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Patent number: 5518859Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group, a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.Type: GrantFiled: March 16, 1995Date of Patent: May 21, 1996Assignee: Kansai Paint Co., Ltd.Inventors: Naozumi Iwasawa, Junichi Higashi
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Patent number: 5508141Abstract: A coating of resin and photoactive functionality is autodeposited from an emulsion onto a metallic substrate in order to selectively protect the substrate from corrosive environments such as etchant processes. An acid and oxidizing agent are included in the emulsion so that when the substrate is immersed in the emulsion the resin and photoactive functionality autodeposits. The resulting coating can be exposed to actinic radiation in an image-wise fashion and developed in an alkaline solution to develop the image created. In instances where the emulsion and process are used to make circuit boards, the metallic surface uncovered during developing is then etched away, leaving only the coated sections of the surface. The resulting coated surfaces will be the circuit traces of the circuit board.Type: GrantFiled: December 2, 1994Date of Patent: April 16, 1996Assignee: W. R. Grace & Co.-Conn.Inventors: Daniel J. Hart, Alan F. Becknell, Betsy Elzufon, John S. Hallock, Alan R. Browne
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Patent number: 5478691Abstract: A radiation-sensitive resin composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound, wherein the alakli-soluble novolak resin comprises a mixture of:95-50 parts by weight of Resin A having a standard polystyrene-reduced weight-average molecular weight of 2,000-20,000 [Resin A is at least one resin selected from the group consisting of a resin obtained by polycondensation of m-cresol and at least one phenol represented by the structural formula (I) or (I'): ##STR1## wherein m is 2 or 3, with at least one aldehyde and a resin obtained by polycondensation of m-cresol, p-cresol and at least one phenol repreented by the above structural formula (I) or (I') with at least one aldehyde] and5-50 parts by weight of Resin B having a standard polystyrene-reduced weight-average molecular weight of 200-2,000 [Resin B is a resin obtained by polycondensation of at least one phenol represented by the structural formula (II): ##STR2## wherein n is 0, 1, 2 or 3, with at least one aldehyde].Type: GrantFiled: June 13, 1994Date of Patent: December 26, 1995Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Satoshi Miyashita, Akihiro Yamanouchi, Ikuo Nozue, Takao Miura
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Patent number: 5449584Abstract: The present invention provides a positive photo-sensitive resin composition comprising a polybenzoxazole precursor as a base resin, an organic solvent-soluble polymer or its precursor (e.g., a polyamic acid) as a component for imparting improved adhesion, flexibility or heat resistance, and a diazoquinone compound and/or a dihydropyridine compound as a photosensitive agent. This photo-sensitive resin composition can form a pattern of high resolution and further has excellent adhesion and mechanical properties. The present invention further provides three novel diazoquinone compounds as a photo-sensitive agent, which compounds give high resolution, high contrast and thick-film formability when compounded in a positive photo-sensitive resin composition. The present invention furthermore provides a new type positive photo-sensitive resin composition obtained by reacting a polybenzoxazole precursor with a diazoquinone compound as a photo-sensitive agent.Type: GrantFiled: March 18, 1994Date of Patent: September 12, 1995Assignee: Sumitomo Bakelite Company, Ltd.Inventors: Toshio Banba, Etsu Takeuchi, Toshiro Takeda, Naoshige Takeda, Akira Tokoh
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Patent number: 5447825Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide-type photosensitive compound and a solvent, as the main components, wherein the alkali-soluble resin is a polycondensation product of 1 at least one phenolic compound of the following formula (A) and 2 (a) formaldehyde and (b) at least one ketone or aldehyde of the following formula (B), and the mixing ratio of the formaldehyde (a) to the ketone or aldehyde (b) is within a range of from 1/99 to 99/1 in terms of the molar ratio of (a)/(b): ##STR1## wherein R.sup.1 is a group of the formula R.sup.2,OR.sup.3,COOR.sup.4 or CH.sub.2 COOR.sup.5,wherein R.sup.2 is a C.sub.1-4 alkyl group, each of R.sup.3,R.sup.4 and R.sup.5 which are independent of one another, is a hydrogen atom or a C.sub.1-4 alkyl group, n is an integer of from 0 to 3, provided that when n is 2 or 3, a plurality of R.sup.1 may be the same or different, and each of R.sup.6 and R.sup.7 which are independent of each other, is a hydrogen atom, a C.sub.Type: GrantFiled: August 31, 1994Date of Patent: September 5, 1995Assignee: Mitsubishi Chemical CorporationInventors: Mineo Nishi, Koji Nakano, Yoshihiro Takada
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Patent number: 5446126Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) washing a cation exchange resin with a solution of a quaternary ammonium compound;(c) contacting the prewashed cation exchange resin with the solution of resist component to remove metal impurities from said solution of resist component; and(d) separating said cation exchange resin bearing said metal impurities from said resist component solution.Type: GrantFiled: September 3, 1991Date of Patent: August 29, 1995Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
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Patent number: 5446125Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) contacting said resist component solution with a cation exchange resin and a chelate resin for a sufficient amount of time to absorb at least a portion of said metal impurities onto said cation exchange and chelate resins; and(c) separating said cation exchange and chelate resins bearing said metal impurities from said resist component solution.Type: GrantFiled: September 3, 1991Date of Patent: August 29, 1995Assignee: OCG Microelectronic Materials, Inc.Inventors: Kenji Honda, Edward A. Fitzgerald, Lawrence Ferreira
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Patent number: 5439774Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group,a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.Type: GrantFiled: September 28, 1994Date of Patent: August 8, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Naozumi Iwasawa, Junichi Higashi
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Patent number: 5437952Abstract: A photosensitive lithographic printing plate comprises a conductive support and provided thereon, a photoconductive layer of a composition comprising a photoconductor and an esterified compound of o-naphtho-quinonediazide sulfonic acid with a phenol resin, the phenol resin being a polycondensation compound of a monovalent phenol with an aldehyde or a ketone, and the content of the o-naphthoquinonediazide sulfonic acid residue being 0.4.times.10.sup.-3 to 3.0.times.10.sup.-3 mole per gram of the photoconductive layer.Type: GrantFiled: February 26, 1993Date of Patent: August 1, 1995Assignee: Konica CorporationInventors: Katsura Hirai, Yasuo Kojima, Kiyoshi Goto
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Patent number: 5427888Abstract: A positive photosensitive resin composition contains 50 to 95 parts by weight of a resin (a) composed of a high molecular compound (A) having a molecular weight of 300 to 30,000 and an iodine value of 50 to 500 and containing carbon-carbon double bonds and a group represented by the formula (I) ##STR1## wherein R.sub.1 denotes a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms and X denotes a hydrogen atom or a bond, on the proviso that if X denotes the bond, a carbon atom linked to R.sub.1 and a carbon atom linked to a hydrogen atom together form a portion of a main chain of the high molecular compound (A), and a group represented by the formula (II) ##STR2## wherein R.sub.1 and X denote the same as above, and R.sub.2 denotes an alkyl, cycloalkyl or aryl group, and 5 to 50 parts by weight of a compound (b) containing quinone diazide groups.Type: GrantFiled: August 3, 1993Date of Patent: June 27, 1995Assignee: Nippon Oil Co., Ltd.Inventors: Eiji Yoda, Hitoshi Yuasa, Yutaka Otsuki
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Patent number: 5422221Abstract: In a resist composition, a novolak resin including at least one recurring unit of the formula (1): ##STR1## wherein n is an integer of 1 to 4 and m is an integer of 0 to 3, having a weight average molecular weight of 1,000 to 10,000 calculated as polystyrene, and having the hydrogen atom of a hydroxyl group therein replaced by a 1,2-naphthoquinonediazidosulfonyl group in a proportion of 0.03 to 0.27 mol per hydrogen atom serves as an alkali-soluble resin and a photosensitive agent. The composition is uniform in that the photosensitive agent is uniformly incorporated in the novolak resin, and thus forms a uniform resist film. It is a useful positive resist having improved sensitivity, resolution, heat resistance, and film retentivity.Type: GrantFiled: February 16, 1994Date of Patent: June 6, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Okazaki, Mitsuo Umemura, Hiroshi Kanbara, Jun Hatakeyama, Tetsuya Inukai, Kazuhiro Nishikawa
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Patent number: 5422223Abstract: Photosensitive silicon-containing resist compositions comprising hydroxyphenylsilsesquioxanes and siloxanes partially estersified with diazonaphthoquinone sulfonyloxy groups for imageable O.sub.2 RIE barrier films. Methods for forming image patterns on substrates using these photosensitive silicon-containing resist compositions are also provided.Type: GrantFiled: July 13, 1994Date of Patent: June 6, 1995Assignee: International Business Machines CorporationInventors: Krishna G. Sachdev, Harbans S. Sachdev, Joel R. Whitaker
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Patent number: 5422222Abstract: A positive-type photosensitive electrodeposition coating composition comprising (A) a photosensitive compound having a molecular weight of not more than 6,000 and containing at least one modified quinonediazidesulfone units represented by the following formula (I) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group,R.sub.3 represents an alkylene group, a cycloalkylene group or an alkylene ether group, andA represents a carboxylic acid ester linkage, in a molecule and; or a photosensitive compound obtained by reacting a polyfunctional amino compound with o-benzoquinonediazidesulfonic acid chloride or o-naphthoquinonediazidesulfonic acid chloride, and (B) a water-soluble or water-dispersible resin having a salt-forming group.Type: GrantFiled: May 26, 1994Date of Patent: June 6, 1995Assignee: Kansai Paint Co., Ltd.Inventors: Yuw Akaki, Junichi Higashi, Naozumi Iwasawa
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Patent number: 5411836Abstract: A positive type photoresist composition contains (a) 100 parts by weight of a resin which is a polymer compound (A) including carbon-carbon double bonds and having a molecular weight of 300 to 30,000 and an iodine value of to 500. To at least a part of the double bonds of the polymer compound (A), a group represented by the formula (I) is introduced ##STR1## wherein R.sup.1 denotes a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms and R.sup.2 denotes an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group or an aryl group, The composition further contains (b) 25 to 100 parts by weight of a compound containing a quinone diazide unit.Type: GrantFiled: August 8, 1991Date of Patent: May 2, 1995Assignee: Nippon Oil Co., Ltd.Inventors: Eiji Yoda, Haruyoshi Sato, Yukio Yamasita, Hitoshi Yuasa, Yutaka Otsuki
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Patent number: 5401604Abstract: A positive-type photosensitive resin composition containing a resin which results from reactions between a specific polyepoxide compound, a carboxylic acid compound having a specific phenolic hydroxyl group, a carboxylic acid compound having no specific phenolic hydroxyl group, and 1,2-quinone diazide sulfonyl halide. The resin composition has high exposure sensitivity, is capable of inhibiting swell or dissolution of unexposed areas during the stage of development, and yet retains other favorable properties. The resin composition has also attained short developing time.Type: GrantFiled: January 31, 1994Date of Patent: March 28, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Chikayuki Otsuka, Mamoru Seio, Kiyomi Sakurai, Kazuyuki Kawamura
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Patent number: 5399462Abstract: A method is provided for forming a microlithographic relief image having a width of less than one half micron in a bilayer resist composition. The resist composition comprises a single component, silicon-containing photoimageable layer and a polymeric underlayer having a high optical density and a refractive index similar to the refractive index of the overlaying resist. The method provides for the formation of a relief image in the top layer using an i-line (365 nm) or deep ultra violet (170 to 300 nm) light source, followed by O.sub.2 RIE transfer of the relief image into the polymeric underlayer.Type: GrantFiled: July 13, 1994Date of Patent: March 21, 1995Assignee: International Business Machines CorporationInventors: Krishna G. Sachdev, Premlatha Jagannathan, Robert N. Lang, Harbans S. Sachdev, Ratnam Sooriyakumaran, Joel R. Whitaker
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Patent number: 5393637Abstract: Disclosed is a photosensitive composition used for offset printing, which provides an offset printing plate with excellent durability and developability. The photosensitive composition comprises:(I) a film-forming binder resin,(II) a photosensitive substance, and(III) a microgel having a particle size of 0.01 to2.0 .mu. prepared by emulsion polymerization using a polymeric emulsifier having an Sp value of 9 to 16.Type: GrantFiled: February 28, 1992Date of Patent: February 28, 1995Assignee: Nippon Paint Co., Ltd.Inventors: Kazunori Kanda, Yoshifumi Ichinose, Seiji Arimatsu, Katsuji Konishi, Takakazu Hase
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Patent number: 5380618Abstract: A micropattern-forming, light sensitive resin composition is disclosed. The composition comprises (a) a novolak resin comprising a condensate between formaldehyde and a mixture of m-cresol and p-cresol with a m-cresol to p-cresol charging weight ratio of from 45/55 to 60/40, wherein the novolak resin has the following characteristics: (i) a dissolving rate of 20 to 800 .ANG./sec in an aqueous solution of tetramethylammonium hydroxide (TMAH) and an alkali activity of 0.131N, (ii) a weight average molecular weight of 1000 to 6000 calculated as polystyrene equivalent, and (iii) a non-exposed dissolving rate of equal to or more than 100 .ANG./sec in an aqueous solution of TMAH with an alkali activity of 0.262N; (b) a light-sensitive substance of 1,2-naphthoquinonediazide-4-sulfonyl ester, and (c) a solvent capable of dissolving the novolak resin and the light-sensitive substance; wherein the novolak resin, the light-sensitive substance, and the solvent are present in such amounts that a 1.Type: GrantFiled: April 19, 1994Date of Patent: January 10, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadayoshi Kokubo, Kazuya Uenishi, Shiro Tan, Wataru Ishii
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Patent number: 5380622Abstract: Negative relief copies are produced by imagewise exposure of a recording plate consisting of a substrate and a photosensitive layer which is applied thereon and contains, as photosensitive compounds, esters of 1,2-naphthoquinone-2-diazide-4- and/or -5-sulfonic acid or -carboxylic acid, heating of the exposed plate, uniform exposure of the plate and development of the relief copy by dissolving the alkali-soluble components from the recording layer by means of an aqueous alkaline developer, by a process in which the photosensitive layer of the recording plate contains a reaction product ofa) from 50 to 99% by weight of an oligomeric or polymeric condensate ofa.sub.1) from 0.5 to 1 mol of an alkyl- and/or alkoxy-substituted monohydric, dihydric or trihydric hydroxybenzene,a.sub.2) from 0 to 0.5 mol of phenol anda.sub.3) from 0.5 to 1.5 mol of a C.sub.1 -C.sub.12 -carbonyl compound,the sum of the amounts of a.sub.1) and a.sub.Type: GrantFiled: April 22, 1991Date of Patent: January 10, 1995Assignee: BASF AktiengesellschaftInventor: Joachim Roser