And Monomeric Processing Ingredient Patents (Class 430/191)
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Patent number: 7462436Abstract: There is provided a positive photoresist composition capable of forming a pattern with excellent resolution, excellent resistance to reflection off the substrate, and excellent perpendicularity. The positive photoresist composition comprises (A) an alkali-soluble novolak resin in which a portion of the hydrogen atoms of all the phenolic hydroxyl groups are substituted with 1,2-naphthoquinonediazidesulfonyl groups, and (B) a dissolution promoter represented by a general formula (b-1) and/or a general formula (b-11) shown below.Type: GrantFiled: July 13, 2004Date of Patent: December 9, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yasuo Masuda, Toshiki Okui
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Patent number: 7455948Abstract: This invention relates to a positive photosensitive resin composition allowing development with an alkaline aqueous solution and excellent in resolution, photosensitivity and pattern form even if the film formed from the resin is thick. Furthermore, this invention relates to a photosensitive resin composition comprising (a) a polymer having one or more phenolic hydroxyl groups, (b) a compound having a phenolic hydroxyl group and containing only one group selected from a methylol group and alkoxymethyl group, and (c) a photo acid generator.Type: GrantFiled: November 16, 2005Date of Patent: November 25, 2008Assignee: Toray Industries, Inc.Inventors: Ryuichiro Taniguchi, Tomoyuki Yuba, Masao Tomikawa
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Patent number: 7435525Abstract: Provided is a positive photosensitive resin composition which is advantageous not only in excellent sensitivity, resolution and adhesion, but also in excellent heat resistance even when the composition is cured by a low-temperature process at equal to or lower than 280° C., as well as low water absorption and capability to give a pattern with favorable configuration. The positive photosensitive resin composition contains: (a) alkaline aqueous solution-soluble polyamide having a polyoxazole precursor structure; (b) an o-quinonediazide compound; and (c) a latent acid generator which generates acid upon heating. The composition optionally further contains (d) a compound having a phenolic hydroxyl group or (e) a solvent.Type: GrantFiled: March 11, 2005Date of Patent: October 14, 2008Assignee: Hitachi Chemical Dupont Microsystems Ltd.Inventors: Takashi Hattori, Yasuharu Murakami, Hiroshi Matsutani, Masayuki Ooe, Hajime Nakano
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Patent number: 7416822Abstract: Disclosed is a hydroxy polyamide represented by the following general formula (1) and having a 5-amino isophthalic acid derivative structure in the main chain structure. (1) (In the formula, m and n represent integers, X represents at least one tetravalent organic group, Y represents at least one divalent organic group having a 5-amino isophthalic acid derivative structure, and Z represents at least one divalent organic group).Type: GrantFiled: January 18, 2005Date of Patent: August 26, 2008Assignee: Asahi Kasei EMD CorporationInventors: Takayuki Kanada, Yasuhiro Kataoka, Motohiro Niwa
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Patent number: 7416830Abstract: A positive-working photosensitive composition comprising one or more polybenzoxazole precursor polymers, a diazonaphthoquinone photoactive compound which is the condensation product of a compound containing from 2 to about 9 aromatic hydroxyl groups with a 5-naphthoquinone diazide sulfonyl compound and a 4-naphthoquinone diazide sulfonyl compound, and at least one solvent, and the use of such compositions to form a relief pattern on a substrate thereby forming a coated substrate.Type: GrantFiled: February 18, 2005Date of Patent: August 26, 2008Assignee: Fujifilm Electronic Materials U.S.A., Inc.Inventors: Ahmad A. Naiini, Richard Hopla, David B. Powell, Jon Metivier, Il'ya Rushkin
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Patent number: 7407731Abstract: A photosensitive resin composition comprising: (a) at least one polybenzoxazole precursor polymer; (b) at least one compound having Structure VI ?wherein, V is CH or N, Y is O or NR3 wherein R3 is H, CH3 or C2H5, R1 and R2 each independently are H, C1-C4 alkyl group, C1-C4 alkoxy group, cyclopentyl or cyclohexyl, or alternatively, R1 and R2 can be fused to produce a substituted or unsubstituted benzene ring; and (c) at least one solvent; wherein the amount of the compound of Structure VI present in the composition is effective to inhibit residue from forming when the composition is coated on a substrate and the coated substrate is subsequently processed to form an image on the substrate, and with the proviso that if the polybenzoxazole precursor polymer solely consists of polybenzoxazole precursor polymers that do not contain a photoactive moiety in the polymer, then (d) at least one photoactive compound is also present in the composition.Type: GrantFiled: March 22, 2006Date of Patent: August 5, 2008Assignee: Fujifilm Electronic Materials U.S.A., Inc.Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Donald F. Perry
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Patent number: 7378215Abstract: A positive photoresist composition comprising an alkali-soluble resin, a 1,2-quinonediazide compound, an organic solvent, and a fluorinated organosilicon compound of formula (1) serving as a surfactant can be effectively coated to uniformity over large areas and is improved in resist pattern profile. Rf is a C5-C30 perfluoroalkyl group containing at least one ether bond, Q is a polyether group consisting of an ethylene glycol and/or propylene glycol polymer chain, R is H or C1-C4 alkyl, X is a divalent linking group exclusive of oxygen, Y is a divalent linking group, p is an integer of at least 3, and 0<n<3.Type: GrantFiled: December 12, 2006Date of Patent: May 27, 2008Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiromasa Yamaguchi, Hideto Kato
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Patent number: 7378230Abstract: The present invention relates to a photoresist composition for an MMN (multi-micro nozzle) head coater, more particularly to a photoresist composition comprising a novolak resin with a molecular weight ranging from 2000 to 12,000, a diazide photoactive compound, an organic solvent, and a Si-based surfactant for use in liquid crystal display circuits. The photoresist composition for liquid crystal display circuits of the present invention solves the stain problem, which occurs in MMN head coaters used for large-scale substrate glass, and improves coating characteristics, so that it can be utilized industrially and is expected to significantly improve productivity.Type: GrantFiled: January 5, 2004Date of Patent: May 27, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Sung-Chul Kang, Jin-Ho Ju, You-Kyoung Lee, Dong-Ki Lee, Hyo-Youl Kim, Hoon Kang, Seung-Uk Lee, Byung-Uk Kim
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Patent number: 7374856Abstract: A positive photosensitive siloxane composition having high photosensitivity and having such properties as high heat resistance, high transparency and low dielectric constant may be used to form a planarization film for a TFT substrate, an interlayer dielectrics or a core or cladding of an optical waveguide. The positive photosensitive siloxane composition includes a siloxane polymer, quinonediazide compound and solvent, and a cured film formed of the composition has a light transmittance per 3 ?m of film thickness at a wavelength of 400 nm of 95% or more.Type: GrantFiled: November 15, 2005Date of Patent: May 20, 2008Assignee: Toray Industries, Inc.Inventors: Mitsuhito Suwa, Takenori Fujiwara, Masahide Senoo, Hirokazu Iimori
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Photosensitive resin composition and method for manufacturing semiconductor apparatus using the same
Patent number: 7371501Abstract: A photosensitive resin composition comprises: a polybenzoxazole precursor (A); a naphthoquinone diazide photosensitizer (B); and a specific phenolic hydroxyl group-containing compound (C).Type: GrantFiled: March 9, 2007Date of Patent: May 13, 2008Assignee: FUJIFILM CorporationInventors: Tsukasa Yamanaka, Kenichiro Sato -
Patent number: 7371499Abstract: A photoresist resin composition comprises about 10 to about 35% by weight of an acryl-based copolymer, about 5 to about 10% by weight of a quinone diazide compound, about 55 to about 80% by weight of a solvent, and about 0.01 to about 0.5% by weight of a silane-based surfactant where the weights of each of the acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant are based on the total weight of acryl-based copolymer, quinone diazide compound, solvent, and silane-based surfactant. An overcoating layer formed using the photoresist resin composition has improved flatness, and thus defects on a display screen may be prevented and/or reduced.Type: GrantFiled: October 19, 2006Date of Patent: May 13, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Young-Tae Noh, Yun-Jung Na, Eun-Joon Park
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Patent number: 7371500Abstract: Positive photosensitive insulating resin compositions of the invention contain at least (A) an alkali soluble resin having a phenolic hydroxyl group, (B) a compound having a quinonediazido group, (C) crosslinked fine particles, (D) a compound containing at least two alkyletherified amino groups in the molecule, and (F) a solvent The resin compositions have excellent resolution, electrical insulating properties and thermal shock properties. Cured products of the invention are obtained by curing these resin compositions, and they show good adhesive properties.Type: GrantFiled: March 28, 2007Date of Patent: May 13, 2008Assignee: JSR CorporationInventors: Katsumi Inomata, Takashi Nishioka, Atsushi Itou, Masayoshi Suzuki, Shin-ichirou Iwanaga
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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: 7368216Abstract: A positive photosensitive resin composition, which contains a polybenzoxazole precursor, a quinonediazide photosensitizer and a carbonate solvent, and a method of manufacturing a semiconductor device using the composition.Type: GrantFiled: January 22, 2007Date of Patent: May 6, 2008Assignee: FUJIFILM CorporationInventors: Kenichiro Sato, Tsukasa Yamanaka
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Patent number: 7361445Abstract: A positive-working photosensitive resin composition containing an alkali soluble resin (A), a diazoquinone compound (B) and a compound (C) which contains a —CH2OH group but not a phenolic hydroxyl group, 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.Type: GrantFiled: July 6, 2005Date of Patent: April 22, 2008Assignee: Sumitomo Bakelite CompanyInventors: Toshio Banba, Takuji Ikeda, Tatsuya Yano, Takashi Hirano
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Patent number: 7348122Abstract: A photosensitive resin composition comprising: a quinone diazide sulfonic acid ester of a phenol compound represented by formula (I) as defined in the specification; and a polybenzoxazole precursor, and a method for manufacturing a semiconductor device using the sameType: GrantFiled: August 29, 2006Date of Patent: March 25, 2008Assignee: FUJIFILM CorporationInventors: Kenichiro Sato, Tsukasa Yamanaka
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Patent number: 7338737Abstract: A photosensitive resin composition includes an alkali-soluble resin, a quinone diazide, a surfactant, and a solvent. The solvent includes a diethylene glycol dialkyl ether that includes an alkyl group including one to five carbon atoms, an ethyl 3-ethoxy propionate, an alkyl acetate that includes an alkyl group including three to eight carbon atoms, and an alkyl lactate that includes an alkyl group including one to six carbon atoms. The composition may be used to make high-quality display panels with uniformly-coated insulating layers.Type: GrantFiled: December 13, 2005Date of Patent: March 4, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Hi-Kuk Lee, Yuko Yako, Dong-Ki Lee, Kyu-Young Kim
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Patent number: 7332254Abstract: Disclosed is a positive photosensitive insulating resin composition including: (A) an alkali soluble resin, (B) a compound having a quinonediazide group, and (C) an epoxy resin having a softening point of not lower than 30° C.; and a cured product which is obtained by curing the composition. The cured product obtained by curing the composition is excellent in resolution, electrical insulation, thermal shock resistance and adhesion, and exhibits reduced deformation after post-baking.Type: GrantFiled: August 18, 2006Date of Patent: February 19, 2008Assignee: JSR CorporationInventors: Hirofumi Sasaki, Atsushi Ito, Hirofumi Goto, Yuichi Hashiguchi
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Patent number: 7297452Abstract: A photosensitive resin composition includes an alkali-soluble resin, a quinone diazide, a surfactant, and a solvent. The surfactant includes an organic fluorine compound having the structure a first silicone compound having the structure a second silicone compound having the structure The resin composition may be used in display panels.Type: GrantFiled: December 23, 2005Date of Patent: November 20, 2007Assignee: Samsung Electronics Co., Ltd.Inventors: Hi-Kuk Lee, Yako Yuko, Kyu-Young Kim
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Patent number: 7291439Abstract: A photoresist composition, a method for forming a film pattern using the photoresist composition, and a method for manufacturing a thin film transistor array panel using the photoresist composition are provided. In one embodiment, a photoresist composition includes an alkali-soluble resin, a photosensitive compound, and an additive, for advantageously providing a uniform photoresist in a channel region.Type: GrantFiled: July 7, 2006Date of Patent: November 6, 2007Assignee: Samsung Electronics Co., Ltd.Inventors: Jeong-Min Park, Hi-Kuk Lee, Jin-Ho Ju, Woo-Seok Jeon, Doo-Hee Jung, Dong-Min Kim, Ki-Sik Choi
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Patent number: 7279263Abstract: A positive-working radiation-sensitive composition for use with a radiation source comprises one or more polymers capable of being eluted in an alkaline aqueous solution and a development-enhancing compound. The invention provides a positive-working photosensitive composition of good sensitivity for use with one or both of ultra-violet radiation and an infrared laser radiation source. The composition is stable in its state before exposure and has an excellent handling property. The sensitivity of a radiation-sensitive coating based on the composition of this invention is increased without compromising the handling characteristics. Radiation-sensitive elements based on the composition of the invention have good development latitude. A positive-working lithographic printing precursor is based on the radiation-sensitive composition coated on a hydrophilic surface.Type: GrantFiled: June 20, 2005Date of Patent: October 9, 2007Assignee: Kodak Graphic Communications Canada CompanyInventor: Jonathan W. Goodin
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Patent number: 7255970Abstract: The present invention provides for a light-sensitive photoresist composition useful for imaging thick films, comprising a polymer which is insoluble in an aqueous alkali developer but becomes soluble prior to development, a photoacid generator which produces a strong acid upon irradiation and a photobleachable dye. The invention further provides for a process for imaging the photoresist of the present invention, especially where the thickness of the photoresist is up to 200 microns and where the process comprises a single exposure step.Type: GrantFiled: July 12, 2005Date of Patent: August 14, 2007Assignee: AZ Electronic Materials USA Corp.Inventors: Medhat A. Toukhy, Ping-Hung Lu, Salem K. Mullen
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Patent number: 7238455Abstract: The invention provides a positive-working photosensitive resin composition comprising an alkali soluble resin (A), a diazoquinone compound (B) and a compound (C) which contains a —CH2OH group but not a phenolic hydroxyl group, 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.Type: GrantFiled: June 23, 2004Date of Patent: July 3, 2007Assignee: Sumitomo Bakelite Company, Ltd.Inventors: Toshio Banba, Takuji Ikeda, Tatsuya Yano, Takashi Hirano
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Patent number: 7220520Abstract: A photosensitive resin composition comprising: (d) at least one polybenzoxazole precursor polymer (e) at least one compound having structure VI V1—Y—V2 VI wherein Y is selected from S, O, NR2, (HOCH)p, and each R1 is selected H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or a halogen, each R2 is selected from H, SH, CH3, C2H5, and a linear or branched C1–C4 alkyl group containing a thiol group; p is an integer of from 1 to 4, and wherein V1 and V2 are independently selected from the group consisting of wherein, m is independently an integer from 0 to 4 with the proviso that m=0 only when Y= n is an integer from 1 to 5; and each R1 is defined as above; and (f) at least one solvent; wherein the amount of the compound of Structure VI present is an amount effective to inhibit residue from forming when the composition is coated on a substrate and the substrate is subsequently processed to form an image, and with the proviso that if the polybenzoxazole precursorType: GrantFiled: June 2, 2006Date of Patent: May 22, 2007Assignee: Fujifilm Electronic Materials U.S.A., Inc.Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Il'ya Rushkin, Richard Hopla
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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: 7214454Abstract: Positive photosensitive insulating resin compositions of the invention contain at least (A) an alkali soluble resin having a phenolic hydroxyl group, (B) a compound having a quinonediazido group, (C) crosslinked fine particles, (D) a compound containing at least two alkyletherified amino groups in the molecule, and (F) a solvent. The resin compositions have excellent resolution, electrical insulating properties and thermal shock properties. Cured products of the invention are obtained by curing these resin compositions, and they show good adhesive properties.Type: GrantFiled: January 15, 2003Date of Patent: May 8, 2007Assignee: JSR CorporationInventors: Katsumi Inomata, Takashi Nishioka, Atsushi Itou, Masayoshi Suzuki, Shin-ichirou Iwanaga
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Patent number: 7195854Abstract: The present invention provides a photoresist composition and more particularly, a photoresist composition comprising a) a novolak resin, b) a diazide compound, and c) a solvent containing propylene glycol methyl ether acetate (PGMEA) and 2,2,4-triemthyl-1,3-penthanediolmonoisobutylate (TMPMB). The photoresist composition according to the invention has excellent coating uniformity and stain inhibitory properties after coating so that it can be easily applied to real industrial fields and it can improve working environments due to the reduction of amounts to be consumed, the decrease of time to be required for manufacture, etc. when manufactured on a large scale.Type: GrantFiled: July 5, 2005Date of Patent: March 27, 2007Assignee: Dongjin Semichem Co., Ltd.Inventors: Hoon Kang, Seung-uk Lee, Woo-sik Jun, Dae-youn Park, Ju-hyuk Kim, Byung-uk Kim
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Patent number: 7195849Abstract: A positive photosensitive resin composition comprising: (a) at least one polybenzoxazole precursor polymer having structure I or II; (b) at least one photosensitive compound selected from compounds described by structures III–V, (c) at least one solvent; and (d) optionally an adhesion promoter.Type: GrantFiled: March 4, 2004Date of Patent: March 27, 2007Assignee: Arch Specialty Chemicals, Inc.Inventors: Ahmad A. Naiini, Pamela J. Waterson, William D. Weber, Ilya Rushkin, Richard Hopla, Jon Metivier
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Patent number: 7175960Abstract: A positive resist composition comprising a mixture of an alkali-soluble novolak resin prepared using m-cresol, p-cresol and 2,5-xylenol as starting reactants and a phenolic compound, wherein the hydrogen atoms of all hydroxyl groups are substituted in a proportion of 0.03–0.05 mol per hydrogen atom with 1,2-naphthoquinonediazidosulfonyl ester groups, has uniformity, high sensitivity and high resolution, and is improved in heat resistance, film retention, substrate adhesion, and storage stability.Type: GrantFiled: September 9, 2004Date of Patent: February 13, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomoyoshi Furihata, Hideto Kato
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Patent number: 7144662Abstract: The present invention relates to a photoresist composition having high heat resistance used in the production process of an LCD, and more particularly, to a photoresist composition having high heat resistance, capable of decreasing process tact (a way), of process simplification, and of the retrenchment of expenditures. The inventive composition facilitates this through making it possible to skip 5 processes, such as Cr metal deposition forming a metal film, and the photo/etch/PR strip/etch steps of the whole surface of the metal, by substituting the inventive composition for the usual metal film, such that N+ ion doping in production of TFT-LCD can take place due its high heat resistance.Type: GrantFiled: February 20, 2002Date of Patent: December 5, 2006Assignee: Samsung Electronics Co., Ltd.Inventors: Dong-Ki Lee, Sung-Chul Kang, You-Kyoung Lee, Jin-Ho Ju
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Patent number: 7132213Abstract: A positive photoresist composition comprising an alkali-soluble novolak resin (A) containing a structural unit (a1) represented by a general formula (I) shown below, and a structural unit (a2) represented by a general formula (II) shown below, and a photosensitizer (B)Type: GrantFiled: July 15, 2004Date of Patent: November 7, 2006Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yasuo Masuda, Toshiki Okui
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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: 7101652Abstract: New photosensitive PBO precursor polymers which contain diazoquinone moieties attached to its backbone and in which all amino end groups are converted into amide groups. The photosensitive formulation based on the disclosed PBO precursor polymers have good imaging and mechanical properties as well as superior shelf life stability. Photosensitive polybenzoxazole precursor polymers having (sulfon)amide end groups (with or without attached diazoquinone groups) can be formulated into photosensitive compositions with diazoquinone photoactive compounds which lack benzylic hydrogens on the backbone to yield compositions producing films significantly lighter in color after curing.Type: GrantFiled: March 9, 2004Date of Patent: September 5, 2006Assignee: Arch Specialty Chemicals, Inc.Inventors: Ahmad A. Naiini, Ilya Rushkin, Richard Hopla, Donald Racicot
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Patent number: 7060410Abstract: There is provided a method of producing a resist composition which yields a resist composition with good storage stability, and no fluctuation in characteristics between production lots. There are provided: a novolak resin solution formed by adding benzoquinone to a novolak resin solution produced by dissolving a novolak resin in an organic solvent; a positive photoresist composition comprising the novolak resin solution and a photosensitive component; a positive photoresist composition comprising the novolak resin solution, a photosensitive component, and hydroquinone; and a method of producing a positive photoresist composition involving mixing the novolak resin solution described above and a photosensitive component.Type: GrantFiled: April 15, 2003Date of Patent: June 13, 2006Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroyuki Ohnishi, Yusuke Nakagawa, Kousuke Doi
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Patent number: 7056641Abstract: A positive photosensitive resin composition of at least one uncapped polybenzoxazole precursor polymer, at least one capped polybenzoxazole precursor polymer, at least one photosensitive agent and at least one solvent, use of such compositions to pattern an image on a substrate and the resulting relied patterned substrates and electronic parts therefrom.Type: GrantFiled: July 8, 2005Date of Patent: June 6, 2006Assignee: Arch Specialty Chemicals, Inc.Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
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Patent number: 7026080Abstract: The invention provides a positive photosensitive resin composition which is free from film reduction, swelling or peeling at the time of development with an aqueous alkaline solution and which provides a dimensionally stable patterns after curing, and of which the final cured film has a low water absorption and excellent alkaline resistance. A positive photosensitive polyimide resin composition characterized by comprising an organic solvent-soluble polyimide having repeating units represented by the formula (1): (wherein m is an integer of from 3 to 10,000, R1 is a tetravalent organic group, R2 is a bivalent organic group, provided that from 5 to 100 mol % of R2 is a bivalent organic group having fluorine), a polyamic acid and a compound capable of generating an acid by irradiation with light.Type: GrantFiled: September 18, 2002Date of Patent: April 11, 2006Assignee: Nissan Chemical Industries, Ltd.Inventors: Tomonari Nakayama, Masakazu Kato, Takayasu Nihira
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Patent number: 7026091Abstract: A positive photoresist with uniform reactivity for use in a thick film lithography process, includes thermal curing during soft-baking and photo dissociation through UV exposure. The positive photoresist comprises a phenolic resin, a resin with acid labile groups, a photoacid generator (PAG), and a reactive monomer with vinyl ether or epoxy group. First, the resins react with the reactive monomer to perform a thermal curing step by soft-baking to form network polymers. In the UV lithography process, the exposed network polymers perform both deprotection and depolymerization simultaneously and are rendered alkali-soluble. The resulting photoresist patterns have a high aspect ratio and resolution profile, due to the good alkali dissolution contrast and uniform reactivity.Type: GrantFiled: July 22, 2004Date of Patent: April 11, 2006Assignee: Industrial Technology Research InstituteInventors: Wei-Chan Tseng, Tsing-Tang Song, Chih-Shin Chuang, Kuen-Yuan Hwang, An-Pang Tu
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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: 6984476Abstract: The invention provides a radiation-sensitive resin composition, by which a patterned insulation film whose water repellency varies is easily formed with high precision, a process for forming a patterned insulation film using this composition, a display element and an flat-panel disply device using the composition, and a process for producing the flat-panel disply device. The resin composition comprises (A) an alkali-soluble copolymer, (B) a 1,2-quinonediazide compound and (C) a water-repellent siloxane resin in particular proportions. In the production process of the patterned insulation film, patterning exposure and development are conducted on a coating formed of the resin composition. The display element and flat-panel disply device are equipped with an interlayer insulation film formed by the resin composition.Type: GrantFiled: April 10, 2003Date of Patent: January 10, 2006Assignees: Sharp Kabushiki Kaisha, JSR CorporationInventors: Kazuki Kobayashi, Ikuo Sakono, Shinji Shiraki, Hirofumi Sasaki, Kazuaki Niwa
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Patent number: 6964838Abstract: A composition includes (A) an alkali-soluble resin, (B) a quinonediazide ester of a compound represented by the following formula: and (C) a compound represented by the following formula: This composition is a positive photoresist composition that is excellent in sensitivity and definition and causes less shrink.Type: GrantFiled: January 4, 2002Date of Patent: November 15, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaki Kurihara, Takako Suzuki, Kenji Maruyama, Satoshi Niikura, Kousuke Doi
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Patent number: 6939926Abstract: A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 ?m and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.Type: GrantFiled: February 9, 2004Date of Patent: September 6, 2005Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6939659Abstract: A positive photosensitive resin composition of at least one uncapped polybenzoxazole precursor polymer, at least one capped polybenzoxazole precursor polymer, at least one photosensitive agent and at least one solvent, use of such compositions to pattern an image on a substrate and the resulting relied patterned substrates and electronic parts therefrom.Type: GrantFiled: March 4, 2004Date of Patent: September 6, 2005Assignee: Arch Specialty Chemicals, Inc.Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
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Patent number: 6933087Abstract: A positive photosensitive resin precursor composition which can be can be developed in an alkaline developer is provided. The positive photosensitive resin precursor composition comprises (a), one of (b1) and (b2), and (c): (a) a polyamic acid ester and/or a polyamic acid polymer, both of which are soluble in an alkaline aqueous solution; (b1) a phenolic-hydroxyl-group-containing thermally crosslinkable compound comprising an organic-group-R1-substituted methylol group represented by formula (1) (wherein R1 is not a hydrogen atom), CH2—OR1)??(1); (b2) a thermally crosslinkable compound containing a ureal organic group substituted by an organic group R1 and represented by formula (2) (c) an esterified quinone diazide compound.Type: GrantFiled: February 21, 2002Date of Patent: August 23, 2005Assignee: Toray Industries, Inc.Inventors: Mitsuhito Suwa, Kazuto Miyoshi, Masao Tomikawa
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Patent number: 6929890Abstract: Disclosed is a positive-type photosensitive resin composition comprising: (a) an alkali-soluble resin; (b) a quinone diazide compound; (c) a heatsensitive compound which colors upon being heated and which shows an absorption maximum at a wavelength of not less than 350 nm and not more than 700 nm; and (d) a compound which does not have an absorption maximum at a wavelength of not less than 350 nm to less than 500 nm, and has an absorption maximum at a wavelength of not less than 500 nm and not more than 750 nm. The composition is preferably used for forming light-blocking separators or black matrices of organic electroluminescent devices and liquid crystal display elements.Type: GrantFiled: April 7, 2004Date of Patent: August 16, 2005Assignee: Toray Industries, Inc.Inventors: Kazuto Miyoshi, Ryoji Okuda, Masao Tomikawa
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Patent number: 6929891Abstract: A heat resistant negative working photosensitive composition that comprises (a) one or more polybenzoxazole precursor polymers (I): wherein x is an integer from about 10 to about 1000, y is an integer from 0 to about 900 and (x+y) is about less then 1000; Ar1 is selected from the group consisting of a tetravalent aromatic group, a tetravalent heterocyclic group, or mixtures thereof; Ar2 is selected from the group consisting a divalent aromatic, a divalent heterocyclic, a divalent alicyclic, a divalent aliphatic group that may contain silicon, or mixtures thereof; Ar3 is selected from the group consisting a divalent aromatic group, a divalent aliphatic group, a divalent heterocyclic group, or mixtures thereof; Ar4 is selected from the group consisting Ar1 (OH)2 or Ar2; G is an organic group selected from the group consisting groups having a carbonyl, carbonyloxy or sulfonyl group attached directly to the terminal NH group of the polymer; (b) one or more photo-active compounds which release acid upon irrType: GrantFiled: March 8, 2004Date of Patent: August 16, 2005Assignee: Arch Specialty Chemicals, Inc.Inventors: Ilya Rushkin, Ahmad A. Naiini, Richard Hopla, Pamela J. Waterson, William D. Weber
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Patent number: 6913865Abstract: The present invention describes encapsulated inorganic resists which are compatible with conventional resist processing and development. The encapsulated inorganic materials increase the plasma etch selectivity of the resists compared to conventional polymeric resists. In effect, these resist systems can act as photoimagable single layer hard mask. In a preferred embodiment, the encapsulated material includes inorganic core particles that are at least partially coated with a moiety having an acid labile or photo-labile protected acidic group such that, upon deprotection, the encapsulated material exhibits greater base solubility.Type: GrantFiled: February 25, 2002Date of Patent: July 5, 2005Assignee: Massachusetts Institute of TechnologyInventor: Theodore H. Fedynyshyn
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Patent number: 6911293Abstract: Disclosed is a photoresist composition comprising: a) at least one film forming resin selected from the group consisting of novolak resins, and polyhydroxystyrenes; b) at least one photoactive compound or photoacid generator; and c) a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a photoresist composition comprising a polycarbonate resin and a solvent composition comprising at least one solvent selected from the group consisting of acetals and ketals. Also disclosed is a process for imaging a photoresist composition, comprising the steps of: a) coating a suitable substrate with any of the aforementioned photoresist compositions; b) baking the substrate to substantially remove the solvent; c) imagewise irradiating the photoresist film; and d) removing the imagewise exposed or, alternatively, the unexposed areas of the coated substrate with a suitable developer.Type: GrantFiled: April 11, 2002Date of Patent: June 28, 2005Assignee: Clariant Finance (BVI) LimitedInventors: Stanley F. Wanat, Joseph E. Oberlander, Robert R. Plass, Douglas McKenzie
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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: 6905809Abstract: 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 photosensitive the photoresist composition; and 3) at least one solvent.Type: GrantFiled: April 1, 2003Date of Patent: June 14, 2005Assignee: Clariant Finance (BVI) LimitedInventor: J. Neville Eilbeck
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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