Polymeric Quinone Diazide Patents (Class 430/190)
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Patent number: 6790581Abstract: A phenolic resin/silicone resin hybrid compound is obtained by effecting hydrolytic condensation of an organooxysilane in the co-presence of a phenolic resin. The hybrid compound is used as the base polymer in a resist for endowing a resist film with excellent adhesion to a metal substrate.Type: GrantFiled: October 11, 2002Date of Patent: September 14, 2004Assignee: Shin-Etsu Chemical Company, LimitedInventors: Hideto Kato, Tomoyoshi Furihata
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Patent number: 6790582Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: a) a novolak resin partially esterified with from about 3 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; and c) at least one solvent.Type: GrantFiled: April 1, 2003Date of Patent: September 14, 2004Assignee: Clariant Finance BVI LimitedInventor: J. Neville Eilbeck
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Patent number: 6783914Abstract: The present invention describes encapsulated inorganic resists which are compatible with conventional resist processing such as spin casting from organic solvents and development with aqueous 2.38% TMAH developers. The resist includes encapsulated inorganic materials as resist components, a fact that significantly increases the plasma etch selectivity of the resists compared to conventional polymeric resists. In effect, these resist systems act as a photoimagable single layer hard mask, although use as the top layer in a bilayer resist scheme is contemplated.Type: GrantFiled: February 25, 2000Date of Patent: August 31, 2004Assignee: Massachusetts Institute of TechnologyInventor: Theodore H. Fedynyshyn
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Patent number: 6773858Abstract: A photoresist composition comprising a novolac resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl groups and an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate is used in microprocessing as a positive photoresist and offers many advantages including uniformity, high sensitivity, high resolution, good pattern shape, heat resistance, film retention, substrate adhesion, shelf stability, and high throughput.Type: GrantFiled: August 6, 2003Date of Patent: August 10, 2004Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hideto Kato, Kyoko Soga, Tomoyoshi Furihata
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Publication number: 20040131964Abstract: A positive resist composition contains a novolak resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl ester groups, a methyl vinyl ether-monoalkyl maleate copolymer and optionally, an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate. The composition is useful as a thick film photoresist which is subject to a plating step and offers many advantages including high sensitivity, perpendicular geometry, high resolution, and crack resistance during and after the plating step.Type: ApplicationFiled: December 18, 2003Publication date: July 8, 2004Inventors: Tomoyoshi Furihata, Hideto Kato
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Publication number: 20040110090Abstract: Processes for imaging and developing imageable elements useful as lithographic printing plate precursors either thermally or with ultraviolet radiation that use the same developer are disclosed. The imageable elements comprise a top layer and an underlayer. The top layer contains a phenolic polymer and a material that has either the o-benzoquinonediazide functionality or the o-diazonaphthoquinone functionality. The developer is a 20:80 to 80:20 mixture of (1) an aqueous alkaline developer that has a pH greater than 11 and contains about 2 wt % to about 8 wt % of an alkali metal silicate, and (2) a solvent based developer that contains about 0.5 wt % to about 15 wt % of an organic solvent or mixture of organic solvents.Type: ApplicationFiled: December 4, 2002Publication date: June 10, 2004Inventors: Jayanti Patel, Kevin B. Ray, Jianbing Huang
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Patent number: 6746812Abstract: A photosensitive resin composition containing a high molecular compound having at least a) a fluoro aliphatic group, and b) a group represented by formula —L—P (wherein L represents a divalent organic group connected to the skeleton of the high molecular compound, and P represents an aromatic group having a carboxyl group at the ortho-position).Type: GrantFiled: May 23, 2001Date of Patent: June 8, 2004Assignee: Fuji Photo Film Co., Ltd.Inventors: Noriaki Watanabe, Koichi Kawamura, Kazuo Fujita, Takeshi Serikawa, Akira Nagashima
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Patent number: 6730769Abstract: (i) As a primary reaction, m-cresol is allowed to react with propionaldehyde in the presence of an acid catalyst and thereby yields a polymer having a weight average molecular weight Mw of 200 to 500 and a molecular weight distribution Mw/Mn of 1.7 or less, and (ii) as a secondary reaction, the polymer is allowed to react with 3,4-xylenol and formaldehyde and thereby yields a novolak resin having an Mw of 1000 to 20000. By adding a specific photosensitizer, the novolak resin yields a positive photoresist composition.Type: GrantFiled: May 1, 2002Date of Patent: May 4, 2004Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akira Katano, Mitsuo Hagihara, Ken Miyagi, Toshiaki Tachi
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Publication number: 20040076911Abstract: The invention is a photoswitchable benzocyclobutene-based polymer that while remaining aqueous developable, avoids the problem of significant moisture uptake. The oligomer or polymer comprises a polymeric backbone, benzocyclobutene reactive groups, and photoswitchable pendant groups. The pendant groups are bonded to the polymeric backbone and are characterized by the presence of a moiety that converts to carboxylic acid upon exposure to activating wavelengths of radiation a carboxylic acid. When the oligomer or polymer is subsequently heated to cause cure of the oligomer or polymer, carbon dioxide is emitted and the group forms a substantially non-polar moiety. The invention is also a method of making such a polymer and a method of forming a patterned film using such a polymer.Type: ApplicationFiled: October 18, 2002Publication date: April 22, 2004Inventors: Ying Hung So, Keith J. Watson, Scott J. Bis
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Patent number: 6706454Abstract: A coating solution useful in the preparation of printing plate precursors comprises: a) a radiation sensitive composition C comprising a phenolic resin; b) at least one thermoplastic polymer P which has a solubility in aqueous alkaline media ranging from sparingly soluble to insoluble; c) a first solvent component A which is capable of solubilizing both composition C and thermoplastic polymer P; d) a second solvent component B having a volatility less than component A, wherein component B is capable of volatilizing composition C but not thermoplastic polymer P, and composition C and thermoplastic P are homogeneously dissolved in a mixture of components A and B; and e) at least one further polymer AP having a higher molecular weight than the phenolic resin of composition C, wherein polymer AB is miscible with the phenolic resin and immiscible with thermoplastic polymer P.Type: GrantFiled: July 5, 2001Date of Patent: March 16, 2004Assignee: Kodak Polychrome Graphics LLCInventor: Mathias Jarek
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Publication number: 20040029032Abstract: A photoresist composition comprising a novolac resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl groups and an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate is used in microprocessing as a positive photoresist and offers many advantages including uniformity, high sensitivity, high resolution, good pattern shape, heat resistance, film retention, substrate adhesion, shelf stability, and high throughput.Type: ApplicationFiled: August 6, 2003Publication date: February 12, 2004Inventors: Hideto Kato, Kyoko Soga, Tomoyoshi Furihata
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Publication number: 20040023166Abstract: The present invention provides methods of forming and using thermally imageable composite elements which may be developed into lithographic printing plates. More specifically, the present invention provides a method of forming thermally imageable composite elements which provide substantial developer resistance in desired regions, while maintaining white light desensitivity and durability.Type: ApplicationFiled: July 30, 2002Publication date: February 5, 2004Inventors: Kevin Ray, Anthony Paul Kitson, Jian Bing Huang
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Publication number: 20040005506Abstract: A radiation sensitive dielectric constant changing composition comprising (A) a decomposable compound, (B) a nondecomposable compound, (C) a radiation sensitive decomposer and (D) a stabilizer.Type: ApplicationFiled: April 1, 2003Publication date: January 8, 2004Inventors: Isao Nishimura, Nobuo Bessho, Atsushi Kumano, Kenji Yamada
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Patent number: 6673706Abstract: A photoresist pattern is formed, without being exposed, by using photoresist having a residual layer proportion characteristic by which the photoresist dissolves at a suitable rate in a developing solution. First, a target layer to be patterned and a photoresist layer are sequentially formed on a substrate having a pattern that defines a step on the substrate. Some of the photoresist layer is treated with the developing solution, to thereby form a photoresist pattern whose upper surface is situated beneath the step and hence, exposes part of the target layer. Next, the exposed part of the target layer, and the photoresist pattern are removed. A silicidation process may be carried out thereafter on the area(s) from which the target layer has been removed. The method is relatively simple because it does not involve an exposure process. Furthermore, the method can be used to manufacture devices having very fine linewidths, i.e.Type: GrantFiled: December 21, 2001Date of Patent: January 6, 2004Assignee: Samsung Electronics Co., Ltd.Inventors: Ji-yong Yoo, Dae-youp Lee, Jeung-woo Lee, Suk-joo Lee, Jae-han Lee
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Patent number: 6670090Abstract: The present invention relates to a positive-working photosensitive composition comprising a partially diazonaphthoquinone (DNQ) capped polyamic ester with a capping level of about 5-80 molar %; a photosensitive agent and a solvent. The composition shows a high photosensitivity and leaves a relief pattern with high resolution and low dark film loss.Type: GrantFiled: September 3, 2002Date of Patent: December 30, 2003Assignee: Industrial Technology Research InstituteInventors: Steve Lien-Chung Hsu, Jinn-Shing King, Po-I Lee, Jhy-Long Jeng
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Patent number: 6667137Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imageable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.Type: GrantFiled: December 30, 2002Date of Patent: December 23, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
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Patent number: 6645689Abstract: A radiation-sensitive composition for use in printing plates is described. The composition comprises: (a) at least one novolak; (b) at least one naphthoquinone diazide derivative; and (c) a copolymer comprising units A, B, and a unit C comprising a cyclic terminal urea group, wherein unit A is present in an amount of about 5 to about 50 mol % and has the formula wherein R1 is selected such that the homopolymer of A is alkali-soluble, unit B is present in an amount of about 20 to about 70 mol % and has the following formula wherein R2 is selected such that the homopolymer of B has a glass transition temperature greater than 100° C., preferably a glass transition temperature in the range from about 100 to about 380° C.Type: GrantFiled: March 13, 2002Date of Patent: November 11, 2003Assignee: Kodak Polychrome Graphics LLCInventor: Mathias Jarek
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Patent number: 6635400Abstract: A resist composition comprising (A) an alkali-insoluble or substantially insoluble polymer having acidic functional groups protected with acid labile groups, which polymer becomes alkali-soluble upon elimination of the acid labile groups, (B) a photoacid generator, and (C) a 1,2-naphthoquinonediazidosulfonyl group-bearing compound has a high resolution and sensitivity, and provides resist patterns of excellent plating resistance when used in UV lithography at an exposure light wavelength of at least 300 nm.Type: GrantFiled: April 17, 2001Date of Patent: October 21, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hideto Kato, Kazuhiro Nishikawa, Yoshinori Hirano, Katsuya Takemura
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Publication number: 20030194635Abstract: The present invention provides a positive working imageable composition, which includes a hydroxyfunctional resin comprising a covalently bound radiation sensitive group capable of increasing the solubility of the imageable composition in an alkaline developer upon exposure to radiation; and an isocyanate crosslinking agent. The present invention further provides an imageable element, which includes a substrate and an imageable composition according to the present invention coated on a surface of the substrate and a method of producing an imaged element according to the present invention. Also provided is a radiation sensitive hydroxyfunctional resin including a covalently bound radiation sensitive group capable of increasing solubility in an alkaline developer of an imageable composition derived therefrom upon exposure of the imageable composition to radiation.Type: ApplicationFiled: January 24, 2002Publication date: October 16, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventor: James Mulligan
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Publication number: 20030194633Abstract: A radiation-sensitive composition for use in printing plates is described.Type: ApplicationFiled: March 13, 2002Publication date: October 16, 2003Inventor: Mathias Jarek
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Publication number: 20030165779Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imageable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.Type: ApplicationFiled: December 30, 2002Publication date: September 4, 2003Applicant: KODAK POLYCHROME GRAPHICS, LLCInventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
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Publication number: 20030099888Abstract: A coating solution useful in the preparation of printing plate precursors comprises:Type: ApplicationFiled: July 5, 2001Publication date: May 29, 2003Applicant: Kodak Polychrome Graphics L.L.C.Inventor: Mathias Jarek
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Patent number: 6558872Abstract: Imagable precursors for masks and for electronic parts comprise a polymeric layer applied to a substrate. The layer comprises at least one polymer having infra-red absorbing groups carried as pendent groups on the polymer backbone. Certain infra-red absorbing groups may also act to insolubilize the polymer in a developer, until it is imagewise exposed to infra-red radiation. Imagewise application of heat, resulting from imagewise exposure of the precursor to infra-red radiation, renders the polymer layer more soluble in the developer than prior to exposure to the infra-red radiation.Type: GrantFiled: September 9, 2000Date of Patent: May 6, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Kevin Barry Ray, Anthony Paul Kitson, Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart
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Publication number: 20030059706Abstract: A positive photoresist composition includes an alkali-soluble novolak resin(A), an alkali-soluble acrylic resin (B) and a quinonediazido-group-containing compound (C) and is used for the formation of a thick film 5 to 100 &mgr;m thick. The ingredient (B) includes 30% to 90% by weight of a unit (b1) derived from a polymerizable compound having an ether bond and 2% to 50% by weight of a unit (b2) derived from a polymerizable compound having a carboxyl group. The composition is applied on a substrate and thereby yields a photoresist film. Likewise, the composition is applied onto a substrate on an electronic part, is patterned, is plated and thereby yields bumps.Type: ApplicationFiled: March 5, 2002Publication date: March 27, 2003Applicant: TOKYO OHKA KOGYO CO., LTD.Inventors: Kouichi Misumi, Koji Saito, Toshiki Okui, Hiroshi Komano
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Publication number: 20030054282Abstract: A negative-working lithographic printing plate has a coating which is imaged by heating an area of the coating with an infrared laser and actinically reacting the coating in the heated area with ultraviolet or visible radiation. The coating contains an infrared absorber but the coating is not imageable by infrared radiation or by the heat generated. The imaging time is reduced since the actinic reaction rate is increased at the elevated temperature.Type: ApplicationFiled: September 16, 2002Publication date: March 20, 2003Inventors: Howard A. Fromson, William J. Rozell
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Patent number: 6517987Abstract: The present invention relates to a positiive-working presensitized plate useful for preparing a lithographic printing plate comprising a positive-working photosensitive composition comprising at least one ester of 1,2-naphthoquinone-2-diazide-5-sulfonic acid, at least one ester of 1,2-naphthoquinone-2-diazide-4-sulfonic acid, and at least one polymer which is insoluble in water and soluble in an aqueous alkaline solution and which comprises at least one group or bond selected from sulfonamide group, urea bond or urethane bond. A lithographic printing plate prepared from the presensitized plate of the present invention shows improvement of chemical-resistance and printing durability, and good sensitivity, coupling property, adaptability to ball-point pen, shelf stability, and stability of sensitivity with time after exposure.Type: GrantFiled: March 20, 2001Date of Patent: February 11, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuo Fujita, Shiro Tan, Akira Nagashima
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Patent number: 6506533Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imagable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.Type: GrantFiled: June 7, 2000Date of Patent: January 14, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
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Patent number: 6475693Abstract: A positive-working radiation-sensitive resin composition showing a good throughput upon production of semiconductors or the like and less process dependence of dimensional accuracy as well as having high sensitivity and high resolution, and being able to form a pattern with good shape and a high aspect ratio.Type: GrantFiled: August 10, 2000Date of Patent: November 5, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Kenji Susukida, Akio Arano, Masato Nishikawa
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Publication number: 20020146635Abstract: A positive photosensitive composition showing a difference in solubility in an alkali developer as between an exposed portion and a non-exposed portion, which comprises, as components inducing the difference in solubility,Type: ApplicationFiled: August 23, 2001Publication date: October 10, 2002Applicant: Mitsubishi Chemical CorporationInventors: Hideki Nagasaka, Akihisa Murata
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Patent number: 6451496Abstract: From a heat-curable photosensitive composition comprising a cresol and/or xylenol novolac resin which has been partially 1,2-naphthoquinonediazido-4- or 5-sulfonate esterified and having a weight average molecular weight of 1,000-10,000, an epoxy compound, and a solvent therefor, a pattern featuring improved solvent resistance and heat resistance can be formed at a high sensitivity and resolution by a simple process. The pattern is suitable as an interlayer insulating film for use in thin-film magnetic heads.Type: GrantFiled: February 15, 2001Date of Patent: September 17, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Kenji Araki, Hideto Kato
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Patent number: 6440646Abstract: A positive resist composition contains (A) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-20,000 wherein 2.5-27 mol % of the hydrogen atom of a hydroxyl group is replaced by a 1,2-naphthoquinonediazidosulfonyl group and (B) a low molecular aromatic compound having phenolic hydroxyl groups and 2-20 benzene rings wherein the ratio of the number of phenolic hydroxyl groups to the number of benzene rings is between 0.5 and 2.5. By forming a resist layer on a substrate from the positive resist composition and baking the resist layer at 90-130° C., followed by exposure and development, there is formed a resist pattern having an undercut of desired configuration. Owing to high resolution and improved dimensional control, heat resistance and film retention, the resist pattern lends itself to a lift-off technique.Type: GrantFiled: February 14, 2001Date of Patent: August 27, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
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Patent number: 6436601Abstract: An infrared imaging composition comprises a mixture of at least two novolak resins esterified with from about 0.1 to 50 mole % of a 2-diazo-1-naphthol-4 or 5-sulfonic acid or derivative thereof, wherein the degree of esterification of one novolak differs from the degree of esterification of the other by at least about 3 mole %, further mixed with an infrared radiation absorbing compound. When applied to a proper support and processed, the composition is useful as an offset lithographics printing plate, color proofing film or image resist.Type: GrantFiled: June 25, 2001Date of Patent: August 20, 2002Assignee: Citiplate, Inc.Inventors: Prakash Seth, Charles S. Cusumano
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Patent number: 6437058Abstract: A polymer in the form of a novolac resin is provided wherein the novolac resin has a weight average molecular weight of 1,000-30,000, some of the hydrogen atoms of hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups, and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted acetal groups and/or crosslinked within a molecule or between molecules with crosslinking groups having C—O—C linkages. The polymer is formulated into a positive resist composition having improved uniformity, sensitivity, resolution and pattern profile as well as improved heat resistance, film retention, substrate adhesion and storage stability.Type: GrantFiled: February 7, 2001Date of Patent: August 20, 2002Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomoyoshi Furihata, Hideto Kato, Yoshinori Hirano
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Patent number: 6423467Abstract: A photosensitive resin composition containing a high molecular compound having at least a) a fluoro aliphatic group, and b) a group represented by formula —L—P (wherein L represents a divalent organic group connected to the skeleton of the high molecular compound, and P represents an aromatic group having a carboxyl group at the ortho-position).Type: GrantFiled: April 6, 1999Date of Patent: July 23, 2002Assignee: Fuji Photo Film Co., Ltd.Inventors: Ikuo Kawauchi, Keiji Akiyama, Noriaki Watanabe, Koichi Kawamura
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Publication number: 20020081517Abstract: A lithographic printing plate has a coating which is imaged by heating an area of the coating with an infrared laser and actinically reacting the coating in the heated area with ultraviolet or visible radiation. The coating can be either positive working or negative working and the coating contains an infrared absorber. The imaging time is reduced since the actinic reaction rate is increased at the elevated temperature.Type: ApplicationFiled: December 22, 2000Publication date: June 27, 2002Applicant: Howard A. FromsonInventors: Howard A. Fromson, William J. Rozell
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Patent number: 6391513Abstract: The positive-working radiation sensitive resin composition which has high sensitivity, high resolution and no residues in development and ability to form a pattern having a good profile. The positive-working radiation sensitive resin composition contains a mixed radiation sensitive novolak resin comprising the mixture of 1,2-naphthoquinonediazide-4-sulfonic acid ester of an alkali soluble novolak resin and 1,2-naphthoquinonediazide-5-sulfonic acid ester of an alkali soluble novolak resin, wherein the ratio by weight of the 1,2-naphthoquinonediazide-4-sulfonyl group and 1,2-naphthoquinonediazide-5-sulfonyl group ranges from 5:95 to 20:80.Type: GrantFiled: March 16, 2001Date of Patent: May 21, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Kenji Susukida, Masato Nishikawa, Akio Arano
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Publication number: 20020048714Abstract: A support for a lithographic printing plate with no damage in appearance such as unevenness in the form of streaks and with excellent pit homogeneity. A support for a lithographic printing plate obtained by subjecting a surface of an aluminum alloy plate to a surface treatment including alkali etching and an electrochemical graining treatment, wherein the aluminum alloy plate shows dispersion of 50% or lower for each element, the dispersion being defined by an specific equation with regard to contents of Fe, Si, Mn, Mg and Sn in a surface layer portion thereof which is from the surface to a depth of 1 &mgr;m.Type: ApplicationFiled: September 6, 2001Publication date: April 25, 2002Inventors: Hirokazu Sawada, Atsuo Nishino, Akio Uesugi
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Patent number: 6376150Abstract: An IR- and UV-radiation-sensitive composition comprising a diazo resin, a diazo ester, at least one novolac resin and an IR-ray absorber. A lithographic plate comprising a support coated with the said photosensitive composition.Type: GrantFiled: May 11, 1999Date of Patent: April 23, 2002Assignee: Lastra S.p.A.Inventors: Angelo Bolli, Paolo Peveri, Andrea Tettamanti
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Patent number: 6372403Abstract: A photosensitive resin composition comprising (a) a photosensitizer having in its structure 1,2-diazidonaphthoquinone structure, and a methylene-bridged structure composed of two or more methyl-substituted phenol derivatives, (b) a polymer having both hydroxyl group and carboxyl group, or a combination of a polymer having hydroxyl group and one having carboxyl group, (c) a crosslinking agent capable of crosslinking hydroxyl group and carboxyl group, and (d) a solvent. This composition can form highly transparent films, and, in addition, patterns having high contrast can be obtained when this composition is used as a photoresist.Type: GrantFiled: November 15, 2000Date of Patent: April 16, 2002Assignee: Clariant Finance (BVI) LimitedInventors: Minoru Kurisaki, Takamasa Harada, Takanori Kudo, Takashi Takeda, Junichi Fukuzawa
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Patent number: 6368774Abstract: A radiation sensitive composition comprising (A), a mixture of an isoindolinone pigment and a yellow organic 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: June 2, 2000Date of Patent: April 9, 2002Assignee: JSR CorporationInventors: Kouichi Sakurai, Hiroaki Nemoto, Atsushi Kumano
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Publication number: 20010041299Abstract: The present invention relates to a positiive-working presensitized plate useful for preparing a lithographic printing plate comprising a positive-working photosensitive composition comprising at least one ester of 1,2-naphthoquinone-2-diazide-5-sulfonic acid, at least one ester of 1,2-naphthoquinone-2-diazide-4-sulfonic acid, and at least one polymer which is insoluble in water and soluble in an aqueous alkaline solution and which comprises at least one group or bond selected from sulfonamide group, urea bond or urethane bond. A lithographic printing plate prepared from the presensitized plate of the present invention shows improvement of chemical-resistance and printing durability, and good sensitivity, coupling property, adaptability to ball-point pen, shelf stability, and stability of sensitivity with time after exposure.Type: ApplicationFiled: March 20, 2001Publication date: November 15, 2001Inventors: Kazuo Fujita, Shiro Tan, Akira Nagashima
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Publication number: 20010038965Abstract: From a heat-curable photosensitive composition comprising a cresol and/or xylenol novolac resin which has been partially 1,2-naphthoquinonediazido-4- or 5-sulfonate esterified and having a weight average molecular weight of 1,000-10,000, an epoxy compound, and a solvent therefor, a pattern featuring improved solvent resistance and heat resistance can be formed at a high sensitivity and resolution by a simple process. The pattern is suitable as an interlayer insulating film for use in thin-film magnetic heads.Type: ApplicationFiled: February 15, 2001Publication date: November 8, 2001Inventors: Takafumi Ueda, Kenji Araki, Hideto Kato
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Publication number: 20010018160Abstract: A positive resist composition contains (A) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-20,000 wherein 2.5-27 mol % of the hydrogen atom of a hydroxyl group is replaced by a 1,2-naphthoquinonediazidosulfonyl group and (B) a low molecular aromatic compound having phenolic hydroxyl groups and 2-20 benzene rings wherein the ratio of the number of phenolic hydroxyl groups to the number of benzene rings is between 0.5 and 2.5. By forming a resist layer on a substrate from the positive resist composition and baking the resist layer at 90-130° C., followed by exposure and development, there is formed a resist pattern having an undercut of desired configuration. Owing to high resolution and improved dimensional control, heat resistance and film retention, the resist pattern lends itself to a lift-off technique.Type: ApplicationFiled: February 14, 2001Publication date: August 30, 2001Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
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Patent number: 6242151Abstract: The invention provides a novel polymer in the form of a novolac resin in which some of the hydrogen atoms of the hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted carbonyl or sulfonyl groups. The polymer has a weight average molecular weight calculated as polystyrene of 1,000-30,000. The polymer is formulated into a resist composition having improved uniformity, sensitivity, resolution and pattern geometry in microfabrication.Type: GrantFiled: August 11, 1999Date of Patent: June 5, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomoyoshi Furihata, Hideto Kato, Satoshi Okazaki
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Patent number: 6232031Abstract: A positive-working, infrared imageable coating and a lithographic printing plate or other element with the coating are described. The coating is a phenolic resin containing an o-diazonaphthoquinone derivative which couples or reacts with the resin to partially insolubilize the coating and an infrared absorbing dye or pigment which further insolubilizes the coating and which renders the coating imageable by infrared radiation. The coating contains only that quantity of infrared radiation absorber necessary to be imageable and only that small quantity of o-diazonaphthoquinone derivative necessary to supplement the insolubilizing function of the absorber. Specifically, the absorber is from 1 to 10 weight percent of the total dry weight of the coating and the dry weight ratio of the absorber to the diazonaphthoquinone moiety is greater than 1:5 and preferably 1:2 or greater.Type: GrantFiled: March 30, 2000Date of Patent: May 15, 2001Assignee: Ano-Coil CorporationInventors: Robert F. Gracia, Yijin Ren, William J. Rozell, Howard A. Fromson
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Patent number: 6218083Abstract: A method for producing a predetermined resist pattern on e.g. a lithographic printing plate, circuit board or mask comprises the imagewise exposure of a radiation sensitive diazide-containing coating (conventionally considered as a UV sensitive material), to non-UV radiation, such as direct heat radiation or infra-red radiation. A positive of the exposed image is revealed on development. Additionally, it has been found that a flood exposure to UV radiation after the imagewise exposure to the non-UV radiation means that a negative of the exposed image is revealed, on development.Type: GrantFiled: March 5, 1999Date of Patent: April 17, 2001Assignee: Kodak Plychrome Graphics, LLCInventors: Christopher D. McCullough, Kevin B. Ray, Alan S. Monk, Stuart Bayes, Anthony P. Kitson
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Patent number: 6218069Abstract: A photosensitive resin composition contains a photosensitive resin comprising recurring units of formula (1) and having a Mw of 1,300-11,000 and 20-5,000 ppm of a tertiary amine compound of formula (2). R is hydrogen or a 1,2-naphthoquinonediazido-5-sulfonic acid residue, the content of 1,2-naphthoquinonediazido-5-sulfonic acid residue in R is 3-27 mol %, and m is a number from 0 to 3, X is a C6-20 alkyl, aryl or aralkyl group, Y and Z each are a C1-20 alkyl group. The composition is improved in sensitivity stability and adhesion to substrates and eliminates the risk of causing corrosion of metal substrates.Type: GrantFiled: January 10, 2000Date of Patent: April 17, 2001Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Hideto Kato, Tomoyoshi Furihata, Satoshi Okazaki
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Patent number: 6210855Abstract: A positive resist composition contains (A) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-20,000 wherein 2.5-27 mol % of the hydrogen atom of a hydroxyl group is replaced by a 1,2-naphthoquinonediazidosulfonyl group and (B) a low molecular aromatic compound having phenolic hydroxyl groups and 2-20 benzene rings wherein the ratio of the number of phenolic hydroxyl groups to the number of benzene rings is between 0.5 and 2.5. By forming a resist layer on a substrate from the positive resist composition and baking the resist layer at 90-130° C., followed by exposure and development, there is formed a resist pattern having an undercut of desired configuration. Owing to high resolution and improved dimensional control, heat resistance and film retention, the resist pattern lends itself to a lift-off technique.Type: GrantFiled: December 14, 1999Date of Patent: April 3, 2001Assignee: Shin Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
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Patent number: 6200727Abstract: A positive photosensitive composition comprising an alkali-soluble resin having phenolic hydroxyl groups (a) and a photo-thermal conversion material (b), and not containing a quinonediazide compound, which contains an alkali-soluble resin having phenolic hydroxyl groups, of which at least some are esterified (a-1).Type: GrantFiled: February 4, 1999Date of Patent: March 13, 2001Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Urano, Akihisa Murata, Etsuko Hino
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Patent number: 6177225Abstract: A positive photosensitive resin composition. The composition comprising: (a) a capped polybenzoxazole precursor polymer having the structure; wherein Ar1 is a tetravalent aromatic group, aliphatic group, heterocylic group, or mixtures thereof; Ar2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Z is one of the following groups: x is 10 to 1000; y is 0 to 900; and b is 0.10 to 350; (b) a photosensitive agent; and (c) a solvent.Type: GrantFiled: September 24, 1999Date of Patent: January 23, 2001Assignee: Arch Specialty Chemicals, Inc.Inventors: William D. Weber, Pamela J. Waterson, Steve Lien-Chung Hsu, Ahmad Naiini