Quinone Diazide Containing Layer Patents (Class 430/165)
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Patent number: 8563215Abstract: The present invention provides novel diazonaphthoquinonesulfonic acid bisphenol derivatives. More particularly, the present invention relates to photo restive coating comprising alkali-soluble resin, a photoactive compound and a surfactant. The photoresist film prepared has less then one micron. The photoactive compound is soluble or swellable in aqueous alkaline solutions and is diazonaphthoquinonesulfonic bisphenol esters of the general formula (A), wherein DNQ represents a 2-Diazo-1-naphthoquinone-4-sulfonyl, 2-Diazo-1-naphthoquinone-5-sulfonyl, 1-Diazo-2-naphthoquinone-4-sulfonyl groups and R1 R1 represents an alkyl, aryl and substituted aryl groups. The invention also provides a process for coating and imaging the light-sensitive composition.Type: GrantFiled: March 20, 2008Date of Patent: October 22, 2013Assignee: Council of Scientific & Industrial ResearchInventors: Vummadi Venkat Reddy, Vaidya Jayathirtha Rao, Mannepalli Lakshmi Kantam, Sunkara Sakunthala Madhavendra, Virendra Kumar Dwivedi
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Patent number: 8530133Abstract: Embodiments in accordance with the present invention provide for norbornane-type ballast materials, norbornane-type photoactive compounds derived from such ballast materials and alkali-soluble positive-tone polymer compositions that encompass such norbornane-type photoactive compounds and one of a PBO or PNB resin.Type: GrantFiled: September 28, 2011Date of Patent: September 10, 2013Assignee: Promerus, LLCInventors: Andrew Bell, Keitaro Seto, Hiroaki Makabe, Edmund Elce
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Patent number: 8501375Abstract: Disclosed is a positive photosensitive resin composition that includes (A) a polybenzoxazole precursor including a repeating unit represented by the following Chemical Formula 1; (B) a photosensitive diazoquinone compound; (C) a silane compound; (D) a phenol compound; and (E) a solvent. In the above Chemical Formula 1, each substituent is the same as defined in the specification.Type: GrantFiled: September 23, 2011Date of Patent: August 6, 2013Assignee: Cheil Industries Inc.Inventors: Hyun-Yong Cho, Min-Kook Chung, Ji-Young Jeong, Jong-Hwa Lee, Yong-Sik Yoo, Jeong-Woo Lee, Hwan-Sung Cheon, Soo-Young Kim, Young-Ho Kim, Jae-Hyun Kim, Su-Min Park
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Patent number: 8367283Abstract: The positive photosensitive resin composition of the present invention has a polyamide resin and a photosensitive agent, wherein the polyamide resin has a specific structure. The cured film of the present invention has a cured product of the positive photosensitive resin composition. The protecting film and insulating film of the present invention has the cured film each. The semiconductor device and display device of the present invention has the cured film each.Type: GrantFiled: July 16, 2009Date of Patent: February 5, 2013Assignee: Sumitomo Bakelite Company, Ltd.Inventor: Miki Terayama
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Patent number: 8309280Abstract: A positive-type photosensitive resin composition includes (A) a polyamide resin that includes a structural unit shown by the following formula (1) and a structural unit shown by the following formula (2), and (B) a photosensitive compound, the polyamide resin (A) having a weight average molecular weight (Mw) of 5000 to 80,000, and a cured film obtained by curing the positive-type photosensitive resin composition at 250° C. having a tensile modulus of elasticity of 2.0 to 4.0 GPa and a tensile elongation of 10 to 100%. According to the present invention, a positive-type photosensitive resin composition that can be cured at a low temperature and a highly reliable semiconductor device including a cured film of the positive-type photosensitive resin composition can be provided.Type: GrantFiled: August 8, 2008Date of Patent: November 13, 2012Assignee: Sumitomo Bakelite Co., Ltd.Inventor: Toshio Banba
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Patent number: 8298743Abstract: A positive-type photosensitive composition including an alkali-soluble polymer formed through copolymerization of monomer (A) represented by the following General Formula (I) and other radical polymerizable monomer (B), a 1,2-quinonediazide compound, and a nanowire structure: where R1 represents a hydrogen atom or a methyl group, R2 represents a hydrogen atom or a C1 to C5 alkyl group, n is an integer of 1 to 5, and m is an integer of 1 to 7.Type: GrantFiled: April 15, 2010Date of Patent: October 30, 2012Assignee: FUJIFILM CorporationInventors: Kenji Naoi, Yoichi Hosoya, Nori Miyagishima
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Patent number: 8158324Abstract: A positive-type photosensitive resin composition, including: (a) a novolac resin; (b) a polymer including, as a main component, a structure represented by formula (1) and/or formula (2): ?(wherein R1 and R2 may be the same or different and each represent an organic group having at least two carbon atoms and a valence of 2 to 8, R3 and R4 may be the same or different and each represent hydrogen or a monovalent organic group of 1 to 20 carbon atoms, —NH—R5 in formula (1) and —CO—R6 in formula (2) each represent a polymer end group, R5 and R6 each represent a monovalent organic group having 2 to 30 carbon atoms which includes an unsaturated hydrocarbon group, n is in the range of 10 to 100,000, l and m each represent an integer of 0 to 2, and p and q each represent an integer of 0 to 4, provided that p+q>0; (c) a quinone diazide compound; (d) an alkoxymethyl group-containing compound; and (e) a solvent.Type: GrantFiled: February 5, 2008Date of Patent: April 17, 2012Assignee: TORAY Industries, Inc.Inventors: Yoji Fujita, Shinji Arimoto, Rinsei Ike
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Patent number: 8034529Abstract: A photosensitive resin composition comprising (a) a compound obtained by reacting a polybasic acid anhydride with the phenolic hydroxyl groups of a novolac-type phenol resin, and (b) a 1,2-quinonediazide compound. The photosensitive resin composition, which comprises component (b) composed of a 1,2-quinonediazide compound in combination with a component (a) obtained by reacting a polybasic acid anhydride with the phenolic hydroxyl groups of a novolac-type phenol resin, exhibits sufficiently high photosensitivity, image contrast, resolution and adhesiveness.Type: GrantFiled: July 19, 2006Date of Patent: October 11, 2011Assignee: Hitachi Chemical Company, Ltd.Inventors: Ken Sawabe, Takeshi Nojiri
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Patent number: 8012664Abstract: A compound of the formula (I) where the symbols and indices are each defined as follows: A is A?, R or O—R; where R is a straight-chain, branched or cyclic, saturated or unsaturated aliphatic radical having 1-8 carbon atoms; A? is the same or different and is B is a bond, —O—C(O)—, —C(O)—O—, —O—C(O)—, —C(O)—NH—, —NH—C(O)—, —C(O)—O—CH2—CH(OH)—CH2—O, —O—CH2—CH(OH)—CH2—O—(O)C—, —O—C(O)—O—, —O—C(O)—NH— or —NH—C(O)—O—; R1 is H or OH; m is 1, 2, 3, 4 or 5; Y is n is a positive rational number ?3; E is the same or different and is —CH—CHR2—, —CHR2—CH2—, —CH2—CHR2—O—, —O—CHR2—CH2—, —(CH2)r—O— or —O—(CH2)—; R2 is H or CH3 and r is 1 or 4, is suitable as a light-sensitive component for photoresists.Type: GrantFiled: November 6, 2006Date of Patent: September 6, 2011Assignee: AZ Electronic Materials USA Corp.Inventors: Wolfgang Zahn, Ralf Grottenmüller, Dieter Wagner
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Patent number: 7875419Abstract: It is an object to provide a technique for removing a resist favorably without leaving residue in the case of using a nonaqueous resist stripper. According to the present invention, in order to achieve the object, when a resist pattern is removed by using the nonaqueous resist stripper, it becomes easier to remove the resist pattern after dry etching or ion doping, by performing exposure treatment on the resist pattern. After a resist pattern is formed from a DNQ-novolac resin type of positive resist composition, the resist pattern is irradiated with light within the range of photosensitive wavelength of the DNQ photosensitizer, thereby removing the resist pattern with the nonaqueous resist stripper.Type: GrantFiled: October 29, 2003Date of Patent: January 25, 2011Assignee: Semiconductor Energy Laboratory Co., Ltd.Inventors: Masaharu Nagai, Kiyofumi Ogino, Teruhisa Nakai, Eiji Shioda
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Patent number: 7847003Abstract: The present invention provides a positive photosensitive resin composition which can form a cured film excellent in process resistance such as heat resistance, solvent resistance or long-time baking resistance and transparency, and which is excellent in photosensitive properties such as resolution and sensitivity, and which has high storage stability and a wide process margin. Further, the present invention provides a positive photosensitive resin composition having such high reliability that no deterioration of electrical characteristics will be led in its application for liquid crystal display devices.Type: GrantFiled: July 28, 2004Date of Patent: December 7, 2010Assignee: Nissan Chemical Industries, Ltd.Inventors: Shinsuke Tsuji, Yosuke Iinuma, Shinya Arase
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Patent number: 7790345Abstract: A positive type photoresist resin film includes a support film and a thermosetting positive type photoresist resin layer laminated over the support film. The positive type photoresist resin layer contains alkali soluble resin, a diazide based photosensitive compound and a sensitivity enhancer. The support film has a surface roughness that inhibits the formation of defect structures such as fish eye. The invention overcomes process inefficiencies and defects cause by spin coating photoresist technologies.Type: GrantFiled: December 7, 2005Date of Patent: September 7, 2010Assignee: Kolon Industries, Inc.Inventors: Byoung-Kee Kim, Se-Hyung Park, Jong-Min Park, Seong-In Baek
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Patent number: 7781131Abstract: A positive-type photosensitive resin composition comprises (A) an alkali-soluble resin having at least a polybenzoxazole precursor structure, (B) a sensitizer, and (C) a cyclic compound having an alcoholic hydroxyl group. A protecting layer and an insulating layer include a cured layer which is a cured product of the positive-type photosensitive resin composition. A semiconductor device and a display device include the cured layer. According to the present invention, a highly reliable positive-type photosensitive resin composition can be obtained even when cured at a low temperature.Type: GrantFiled: August 20, 2008Date of Patent: August 24, 2010Assignee: Sumitomo Bakelite Co., Ltd.Inventor: Hiroaki Makabe
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Patent number: 7749676Abstract: A positive type photoresist resin film contains a support film and a positive photoresist resin layer laminated over the support film. The peak height (Rp) of the support film is less than about 300 nm to eliminate fish eye defects. The positive photoresist resin layer may contain alkali soluble resin, a diazide based photosensitive compound, a plasticizer and, optionally, a sensitivity enhancer and a releasing agent.Type: GrantFiled: December 7, 2005Date of Patent: July 6, 2010Assignee: Kolon Industries, Inc.Inventors: Se-Hyung Park, Byoung-Kee Kim, Jong-Min Park, Seong-In Baek
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Patent number: 7507518Abstract: The present invention relates to a positive photosensitive resin precursor composition which exhibits good storage stability after exposure. A photosensitive resin precursor composition comprises (a) a polymer essentially composed of a structural unit expressed by formula (1); (b) at least two photo acid generators; and (c) a compound having an alkoxymethyl group: wherein R1 represents an organic group with a valence of 2 to 8, having at least two carbon atoms; R2 represents an organic group with a valence of 2 to 6, having at least two carbon atoms; R3 represents hydrogen or an organic group having a carbon number in the range of 1 to 20; n represents a number ranging from 10 to 100,000; m represents an integer in the range of 0 to 2; and p and q represent integers in the range of 0 to 4 and satisfy p+q>0.Type: GrantFiled: July 7, 2004Date of Patent: March 24, 2009Assignee: Toray Industries, Inc.Inventors: Yoji Fujita, Tomoyuki Yuba, Mitsuhito Suwa
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Patent number: 7419763Abstract: A near-field photoresist for formation of a fine pattern with by near-field exposure includes an alkali-soluble novalac resin, a diazyde-type photosensitizer which is photoreactive by near-field exposure, a photoacid generator which generates acid by the near-field exposure, and a solvent.Type: GrantFiled: February 7, 2007Date of Patent: September 2, 2008Assignee: Canon Kabushiki KaishaInventors: Takako Yamaguchi, Ryo Kuroda
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Patent number: 7368205Abstract: The invention provides a polyamide resin having a structure represented by the formula (1), wherein about 0.1 mol % to about 30 mol % of the total amount of Y in the formula (1) has a structure represented by the formula (2), further a positive-working photosensitive resin composition comprising a diazoquinone compound, a method for producing a pattern-formed resin film using the composition, a semiconductor device and a display device using the composition, and a method for producing the semiconductor device and the display device: wherein, X is an organic group of 2 to 4 valences; Y is an organic group of 2 to 6 valences; R1 is a hydroxyl group or —O—R3 wherein m is an integer of 0 to 2; R2 is a hydroxyl group, a carboxyl group, —O—R3 or —COO—R3 wherein n is an integer of 0 to 4; R3 is an organic group having 1 to 15 carbon atoms; wherein, each of R4 and R5 is a divalent organic group; each of R6 and R7 is a monovalent organic group; n is an integer of 0 to 20.Type: GrantFiled: August 6, 2004Date of Patent: May 6, 2008Assignee: Sumitomo Bakelite Co., Ltd.Inventors: Toshio Banba, Takashi Hirano
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Patent number: 7217489Abstract: A negative-type planographic printing plate having, disposed on a support, a recording layer comprising an image recording material which contains an infrared ray absorbing agent and can be recorded by irradiation with an infrared ray, in which, as for the infrared ray absorbing agent comprising a cyanine dye, at least one of substituents on nitrogen atoms at both ends was selected from the group consisting of the following substituents: —C(?X)R1; —C(?X)NR2R3; —CH?CR4R5; —C?CR6; —CHR7R8;—CR9R10R11; and —Ar, wherein X represents O, S or Se; R1 to R6 each independently represent H or a hydrocarbon group having 20 or fewer carbon atoms which may have a substituent; R7 to R11 each independently represent a hydrocarbon group having 20 or fewer carbon atoms which may have a substituent; and Ar represents an aromatic group which may have a substituent.Type: GrantFiled: March 18, 2003Date of Patent: May 15, 2007Assignee: Fujifilm CorporationInventors: Yukio Abe, Kazuto Shimada
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Patent number: 7214455Abstract: The present invention is directed to a photosensitive resin composition comprising (a) a resin having a specific structure, (b) a photosensitive agent, and (c) an organic solvent having a boiling point at atmospheric pressure of 100° C. or higher and 140° C. or lower, the content of the component (c) being 50% by weight or more and 100% by weight or less based on the total amount of the organic solvent, and to a process for producing a heat-resistant resin film using the same. According to the present invention, there is provided a photosensitive resin composition which is less likely to cause defects such as transcribed trace and line drawing.Type: GrantFiled: May 28, 2003Date of Patent: May 8, 2007Assignee: Toray Industries, Inc.Inventors: Kazuto Miyoshi, Ryoji Okuda, Masao Tomikawa
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Patent number: 7101650Abstract: The present invention relates to a photosensitive resin composition for use as a photoresist, and more particularly, to a photosensitive resin composition for a photoresist comprising an acrylate copolymer obtained by selectively using specific compounds or controlling the ratio of unreacted monomers, and a 1,2-quinonediazide compound, which is excellent in several performance factors such as dielectric characteristics, flatness, transparency, developing performance, residual film rate, chemical resistance, and heat resistance, as well as sensitivity and resolution, and in particular it facilitates easy pattern formation into interlayer dielectrics, and it can be used as a photoresist in an LCD manufacturing process due to its excellent transmissivity even when prepared as a thick film.Type: GrantFiled: August 20, 2002Date of Patent: September 5, 2006Assignee: Dongjin Semichem Co., Ltd.Inventors: Byung-Uk Kim, Joon-Yeon Cho, Kyong-Il Kwon, Soo-Jung Park, Jae-Won Yoo
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Patent number: 7029820Abstract: Disclosed is a support for a lithographic printing plate obtainable by performing at least graining treatment on an aluminum plate, having on its surface thereof, a grain shape with a structure in which a grained structure with medium undulation of 0.5 to 5 ?m average aperture diameter and a grained structure with small undulation of 0.01 to 0.2 ?m average aperture diameter are superimposed, and a presensitized plate provided with an image recording layer on the support for a lithographic printing plate. By using this presensitized plate, a balance between scum resistance and press life when a lithographic printing plate is produced therefrom, which has been in a trade-off relation in the past, can be maintained at a high level.Type: GrantFiled: October 7, 2002Date of Patent: April 18, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshinori Hotta, Hisashi Hotta, Tadashi Endo
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Patent number: 7022463Abstract: A near-field photoresist for formation of a fine pattern with by near-field exposure includes an alkali-soluble novalac resin, a diazyde-type photosensitizer which is photoreactive by near-field exposure, a photoacid generator which generates acid by the near-field exposure, and a solvent.Type: GrantFiled: August 19, 2004Date of Patent: April 4, 2006Assignee: Canon Kabushiki KaishaInventors: Takako Yamaguchi, Ryo Kuroda
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Patent number: 7001705Abstract: The present invention provides a positive photosensitive resin composition which can be developed with a tetramethylammonium hydroxide aqueous solution with a usual concentration, has high sensitivity and excellent resolution, and is excellent in heat resistance, planarization properties, transparency, low water absorption or the like. Further, the present invention provides a method for arbitrarily forming a pattern having a semicircular or trapezoidal section by using the composition. The positive photosensitive resin composition of the present invention comprises an alkali-soluble resin, a 1,2-quinone diazide compound, a crosslinking compound having at least two epoxy groups and a surfactant, and the alkali-soluble resin is a copolymer comprising a carboxylic group-containing acrylic monomer, a hydroxyl group-containing acrylic monomer and an N-substituted maleimide as essential components.Type: GrantFiled: April 18, 2003Date of Patent: February 21, 2006Assignee: Nissan Chemical Industries, Ltd.Inventors: Tadashi Hatanaka, Takayasu Nihira
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Patent number: 6908717Abstract: The present invention provides a positve photosensitive resin composition of high sensitivity which can form a pattern of high resolution and high residual film ration and which can give a cured film superior in mechanical properties, adhesivity and water absorptivity. That is, the present invention lies in a positive photosensitve resin compostion comprising 100 parts by weight of an alkali-soluble resin, 1 to 100 parts by weight of a photosensitve diazoquinone compound (B) and a filler (C), characterized in that content F of the filler (C) represented by the following formula is 2 to 70% by weight.Type: GrantFiled: October 9, 2001Date of Patent: June 21, 2005Assignees: Sumitomo Bakelite Company Limited, Intel CorporationInventors: Takashi Hirano, Shusaku Okaaki, Michael D. Goodner, Robert P. Meagley
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Patent number: 6893791Abstract: Disclosed is a photoresist composition having a good sensitivity and residual layer characteristic and a method of forming a pattern using the same. The photoresist composition includes 5-30% by weight of a polymer resin, 2-10% by weight of a photosensitive compound, 0.1-10% by weight of a sensitivity enhancing agent, 0.1-10% by weight of a sensitivity restraining agent and 60-90% by weight of an organic solvent. A photoresist layer is formed by coating the photoresist composition on a substrate and then drying the coated photoresist composition. Then, thus obtained photoresist layer is exposed by using a mask having a predetermined pattern. Then, a photoresist pattern is formed by developing thus exposed photoresist layer. The photoresist pattern exhibits a uniform layer thickness and critical dimension.Type: GrantFiled: September 27, 2002Date of Patent: May 17, 2005Assignee: Samsung Electronics Co., Ltd.Inventors: You-Kyoung Lee, Sung-Chul Kang, Jin-Ho Ju, Dong-Ki Lee, Seung-Uk Lee, Hoon Kang
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Patent number: 6893795Abstract: A positive working lithographic printing plate precursor comprising a lower layer containing a water-insoluble and alkali-soluble resin, and an upper heat-sensitive layer containing a water-insoluble and alkali-soluble resin and an infrared absorbing dye and increasing the solubility in an alkaline aqueous solution by heating, provided in this order on a hydrophilic support, and (a) the upper heat-sensitive layer containing at least two kinds of surface active agents, or (b) the lower layer and upper heat-sensitive layer each containing a surface active agent different from each other.Type: GrantFiled: July 9, 2002Date of Patent: May 17, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Ikuo Kawauchi, Akio Oda, Hideo Miyake
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Patent number: 6855292Abstract: An automated in situ heat induced antigen recovery and staining method and apparatus for treating a plurality of microscope slides. The process of heat induced antigen recovery and the process of staining the biological sample on the microscope slide are conducted in the same apparatus, wherein the microscope slides do not need to by physically removed from one apparatus to another. Each treatment step occurs within the same reaction compartment. The reaction conditions of each reaction compartment for treating a slide can preferably be controlled independently, including the individualized application of reagents to each slide and the individualized treatment of each slide. The reagents are preferably held in a reagent dispensing strip similar to a “blister pack”.Type: GrantFiled: March 14, 2003Date of Patent: February 15, 2005Inventor: Lee Angros
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Patent number: 6849391Abstract: There is provided a positive photoresist for near-field exposure excellent in light utilization efficiency even with small layer thickness of the photoresist layer for image formation, and allowing for reduced pattern edge roughness, and a photolithography method including a step of exposing by the near-field exposure the photoresist layer for image formation made thereof. In a positive photoresist containing an alkali-soluble novolak resin and a quinone diazide compound, the film thickness of the photoresist at the time of exposure is not larger than 100 nm, and the absorption coefficient of the photoresist ? (?m?1) for the exposure light is such that 0.5???7.Type: GrantFiled: June 10, 2002Date of Patent: February 1, 2005Assignee: Canon Kabushiki KaishaInventors: Takako Yamaguchi, Yasuhisa Inao
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Patent number: 6841330Abstract: A positive planographic printing plate precursor comprising a recording layer containing a water-insoluble and alkali-soluble resin, an infrared absorbent and an organic quaternary ammonium salt. A positive planographic printing plate precursor comprising at least two recording layers containing the resin and the infrared absorbent with a coating amount of an upper positive recording layer being in the range of 0.05 to 0.45 g/m2.Type: GrantFiled: November 30, 2001Date of Patent: January 11, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Hideo Miyake, Akio Oda, Tomoyoshi Mitsumoto, Kaoru Iwato
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Patent number: 6824947Abstract: Photosensitive compositions comprising a phenol resin having a urea bond in the main chain, planographic printing plate precursors containing the photosensitive compositions, and methods for preparing planographic printing plates using the planographic printing plate precursors are disclosed. Planographic printing plates that exhibit good durability, good exposure visual image property, and good solvent resistance; particularly superior resistance to washing oil used in UV ink printing; and superior baking property are produced.Type: GrantFiled: February 19, 2003Date of Patent: November 30, 2004Assignee: Kodak Polychrome Graphics, LLCInventors: Yasuhiro Ishizuka, Yasuhiko Kojima
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Patent number: 6821692Abstract: The present invention relates to novel thin layers for microsystem techniques and microstructuring. It is an object of the invention to provide thin layers which can be manufactured under less problems and more economically than the previous conventional layers, and which permit the use of existing technologies for microstructuring. The object is realized in that the thin layer is formed of an enzymatically degradable biopolymer in a range of layer thicknesses of from 30 nm to 3 &mgr;m. Biopolymeric thin layers manufactured according to the invention permit their application, after a respective structurizing, as test assays or in setting up substance libraries.Type: GrantFiled: February 4, 1999Date of Patent: November 23, 2004Assignee: Clondiag Chip Technologies GmbHInventors: Eugen Ermantraut, Johann Michael Köhler, Torsten Schulz, Klaus Wohlfart, Stefan Wölfl
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Patent number: 6815140Abstract: A positive resist composition, having a superior resolution as well as good resist performances such as sensitivity, depth of focus and profile, is described and includes a novolac resin, a radiation-sensitive quinonediazide compound and a thioxanthone compound represented by the following formula (I): wherein R1, R2, R3, R4, R5, R6, R7 and R8 independently represent hydrogen, halogen, alkyl, alkoxy, aryl, carboxyl or alkoxycarbonyl.Type: GrantFiled: June 1, 1999Date of Patent: November 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Hiroshi Moriuma, Yoshiyuki Takata
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Patent number: 6806019Abstract: A radiation sensitive resin composition for i-line light exposure comprising an alkaline soluble resin and a quinonediazide group-containing photosensitizer where said alkaline soluble resin comprises a novolak resin and a mixture of one or two or more of resins selected from the group of (i) polyacrylate, (ii) polymethacrylate, (iii) a polystyrene derivative and (iv) a copolymer consisting of two or more of monomer units selected from the group of acrylic ester, methacrylic ester and styrene derivatives is applied on a substrate such as a substrate for a flat panel display and exposed preferably at the light-exposure quantity of 50 to 500 mJ/cm2 by an i-line light exposure source to form a pattern with high-resolution and a good pattern shape having no tailing.Type: GrantFiled: August 8, 2002Date of Patent: October 19, 2004Assignee: Clariant Finance (BVI) LimitedInventor: Shuichi Takahashi
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Publication number: 20040197696Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: 1) a film-forming novolak resin wherein the hydrogen atom of a hydroxyl group in the novolak resin is substituted with a naphthoquinonediazidosulfonyl (DNQ) group in a proportion of less than 3.0 mol % per hydrogen atom to form a partially esterified novolak resin; 2) at least one photosensitive component present in an amount sufficient to photosensitize the photoresist composition; and 3) at least one solvent.Type: ApplicationFiled: April 1, 2003Publication date: October 7, 2004Inventor: J. Neville Eilbeck
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Publication number: 20040185368Abstract: The present invention relates to a light-sensitive photoresist composition especially useful for imaging thick films, comprising a film-forming alkali-soluble resin, a photoactive compound, and a surfactant at a level ranging from about 2000 ppm to about 14,000 ppm by weight of total photoresist. Preferably the photoresist film has a thickness greater than 20 microns. The invention further provides for a process for coating and imaging the light-sensitive composition of this invention.Type: ApplicationFiled: March 21, 2003Publication date: September 23, 2004Inventors: Ralph R. Dammel, Stephen Meyer, Mark A. Spak
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Patent number: 6783911Abstract: 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: GrantFiled: January 24, 2002Date of Patent: August 31, 2004Assignee: Kodak Polychrome Graphics LLCInventor: James Mulligan
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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: 20040126693Abstract: A positive photosensitive composition and method of pattern formation using the same. The composition comprises a precursor of poly(imide-benzoxazole) (PIBO) copolymer prepared by the reaction of trimellitic anhydride halide monomer with bis(o-diaminophenol) monomer; a photosensitizer; and a solvent.Type: ApplicationFiled: July 23, 2003Publication date: July 1, 2004Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE.Inventors: Shih-Fan Wang, Shing-Tza Liou, Shih-Jung Tsai, Steve Lien-Chung Hsu, Po-I Lee
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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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Publication number: 20040101780Abstract: A planographic printing plate precursor includes a support having disposed thereon a recording layer containing a water-insoluble and alkali-soluble resin, a development inhibitor and an infrared absorber and exhibiting enhanced solubility in an aqueous alkali solution through light exposure. The recording layer may have either a mono-layer construction or a multi-layer construction containing a lower layer and an upper layer. In the case of the multi-layer construction, a layer containing the water-insoluble and alkali-soluble resin is used as the lower layer, and a layer containing the water-insoluble and alkali-soluble resin and the development inhibitor and exhibiting enhanced solubility in an aqueous alkali solution through light exposure is used as the upper layer, and at least one of the lower layer and the upper layer contains the infrared absorber.Type: ApplicationFiled: November 6, 2003Publication date: May 27, 2004Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Kazuo Maemoto
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Publication number: 20040091820Abstract: It is an object to provide a technique for removing a resist favorably without leaving residue in the case of using a nonaqueous resist stripper. According to the present invention, in order to achieve the object, when a resist pattern is removed by using the nonaqueous resist stripper, it becomes easier to remove the resist pattern after dry etching or ion doping, by performing exposure treatment on the resist pattern. After a resist pattern is formed from a DNQ-novolac resin type of positive resist composition, the resist pattern is irradiated with light within the range of photosensitive wavelength of the DNQ photosensitizer, thereby removing the resist pattern with the nonaqueous resist stripper.Type: ApplicationFiled: October 29, 2003Publication date: May 13, 2004Inventors: Masaharu Nagai, Kiyofumi Ogino, Teruhisa Nakai, Eiji Shioda
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Patent number: 6733949Abstract: Disclosed is an alkali-soluble, film-forming novolak resin mixture containing at least two novolak resins, each novolak resin containing the addition-condensation reaction product of at least one phenolic compound with at least one aldehyde source, wherein the phenolic compound for first novolak resin contains 90-100 mole % of meta-cresol, and the phenolic compound for the second novolak resin contains less than 50 mole % of meta-cresol. Also disclosed is a photosensitive composition, containing an admixture of: a) the above-mentioned novolak resin mixture; b) at least one o-quinone photoactive compound; and c) at least one photoresist solvent.Type: GrantFiled: April 11, 2002Date of Patent: May 11, 2004Assignee: Clariant Finance (BVI) LimitedInventors: J. Neville Eilbeck, Alberto D. Dioses
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Patent number: 6713225Abstract: The invention provides a 1,2-naphthoquinone-2-diazidesulfonate ester photosensitive agent which is useful as a photosensitive agent employed in a photoresist for producing semiconductor integrated circuits, liquid crystal displays, EL displays, etc., a method for producing the photosensitive agent, and a photoresist composition containing the photosensitive agent.Type: GrantFiled: March 11, 2003Date of Patent: March 30, 2004Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
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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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Patent number: 6699636Abstract: Imageable elements useful in lithographic printing, and processes for their use, are disclosed. The elements comprise a hydrophilic substrate, an imageable layer over the substrate, and a thermally activated crosslinking agent. The imageable layer comprises a polymeric material that comprises one or more functional groups selected from the group consisting of carboxyl, carboxylic acid anhydride, phenolic hydroxyl, and sulphonamide. A preferred crosslinking group is the oxazoline group. The element is heated after exposure and development to crosslink a polymeric material.Type: GrantFiled: December 12, 2001Date of Patent: March 2, 2004Assignee: Kodak Polychrome Graphics LLCInventor: Celin Savariar-Hauck
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Patent number: 6689531Abstract: A resist composition showing excellent close adherence at the interface of a substrate and a resist, improving problems in wet etching, having excellent sensitivity and resolution, and also showing excellent resist performances, and comprising a compound of the general formula (I): wherein, R1 and R2 represent each independently a hydrogen atom or an alkyl group, R3 represents a hydrogen atom, alkyl group, aryl group, aralkyl group, alkenyl group, alkylcarbonyl group, arylcarbonyl group or aralkylcarbonyl group, n represents an integer of 1 to 40, m represents an integer of 1 to 5, and l represents an integer of 1 to 5, is provided.Type: GrantFiled: August 27, 2002Date of Patent: February 10, 2004Assignees: Sumitomo Chemical Company, Limited, Dongwoo Fine-Chem Co., Ltd.Inventors: Sang Tae Kim, Seung Jin Kang, Shi Jin Sung, Masumi Suetsugu, Airi Yamada
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Publication number: 20040023147Abstract: A positive photosensitive resin composition having high sensitivity is provided which can form patterns with high resolution and high film thickness retention and can give by curing film excellent in mechanical characteristics, adhesion, and water absorption. This composition comprises 100 parts by weight of an alkali-soluble resin, 1 to 100 parts by weight of a photosensitive diazoquinone compound (B) and a filler (C), the content (F) of the filler(C) as defined by the following formula ranging from 2 to 70 wt %.Type: ApplicationFiled: April 25, 2003Publication date: February 5, 2004Inventors: Takashi Hirano, Shusaku Okaaki
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Patent number: 6686120Abstract: Disclosed is a photoresist composition including a thermal acid generator and a method of forming a pattern using the same. The photoresist composition includes about 100 parts by weight of an alkali-soluble acryl copolymer, about 5-100 parts by weight of 1,2-quinonediazide compound, about 2-35 parts by weight of nitrogen-containing cross-linking agent and about 0.1-10 parts by weight of a thermal acid generator which produces an acid by heat. The photoresist composition is coated on a substrate and dried to form a photoresist layer. The photoresist layer is exposed by using a mask having a predetermined shape. Thus obtained exposed photoresist layer is developed by using an aqueous alkaline solution to form a photoresist pattern. Thus obtained photoresist pattern is heated to be cured without generating thermal reflow.Type: GrantFiled: August 15, 2002Date of Patent: February 3, 2004Assignee: Samsung Electronics Co., Ltd.Inventors: You-Kyoung Lee, Sung-Chul Kang, Jin-Ho Ju, Dong-Ki Lee
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Publication number: 20040013965Abstract: A positive photosensitive composition for use with a radiation source comprises one or more polymers capable of being dissolved in an alkaline aqueous solution and a compound which, upon being heated, releases gas. The composition is stable in its state before exposure and has an excellent handling property. The sensitivity of a recording layer based on the composition of this invention is increased without compromising the handling characteristics. In addition radiation sensitive-elements based on the composition of the invention have good development latitude.Type: ApplicationFiled: March 17, 2003Publication date: January 22, 2004Inventors: Livia T. Memetea, Jonathan W. Goodin, Nicholas Bradford, Juana G. Jaramillo, Cheng Yang
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Patent number: RE41083Abstract: 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 is represented by 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 is represented by 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: July 26, 2005Date of Patent: January 19, 2010Assignee: Eastman Kodak CompanyInventor: Mathias Jarek