And Monomeric Processing Ingredient Patents (Class 430/191)
  • Patent number: 7462436
    Abstract: 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: Grant
    Filed: July 13, 2004
    Date of Patent: December 9, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuo Masuda, Toshiki Okui
  • Patent number: 7455948
    Abstract: 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: Grant
    Filed: November 16, 2005
    Date of Patent: November 25, 2008
    Assignee: Toray Industries, Inc.
    Inventors: Ryuichiro Taniguchi, Tomoyuki Yuba, Masao Tomikawa
  • Patent number: 7435525
    Abstract: 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: Grant
    Filed: March 11, 2005
    Date of Patent: October 14, 2008
    Assignee: Hitachi Chemical Dupont Microsystems Ltd.
    Inventors: Takashi Hattori, Yasuharu Murakami, Hiroshi Matsutani, Masayuki Ooe, Hajime Nakano
  • Patent number: 7416822
    Abstract: 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: Grant
    Filed: January 18, 2005
    Date of Patent: August 26, 2008
    Assignee: Asahi Kasei EMD Corporation
    Inventors: Takayuki Kanada, Yasuhiro Kataoka, Motohiro Niwa
  • Patent number: 7416830
    Abstract: 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: Grant
    Filed: February 18, 2005
    Date of Patent: August 26, 2008
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, Richard Hopla, David B. Powell, Jon Metivier, Il'ya Rushkin
  • Patent number: 7407731
    Abstract: 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: Grant
    Filed: March 22, 2006
    Date of Patent: August 5, 2008
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Donald F. Perry
  • Patent number: 7378215
    Abstract: 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: Grant
    Filed: December 12, 2006
    Date of Patent: May 27, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hiromasa Yamaguchi, Hideto Kato
  • Patent number: 7378230
    Abstract: 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: Grant
    Filed: January 5, 2004
    Date of Patent: May 27, 2008
    Assignee: 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
  • Patent number: 7374856
    Abstract: 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: Grant
    Filed: November 15, 2005
    Date of Patent: May 20, 2008
    Assignee: Toray Industries, Inc.
    Inventors: Mitsuhito Suwa, Takenori Fujiwara, Masahide Senoo, Hirokazu Iimori
  • Patent number: 7371501
    Abstract: A photosensitive resin composition comprises: a polybenzoxazole precursor (A); a naphthoquinone diazide photosensitizer (B); and a specific phenolic hydroxyl group-containing compound (C).
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: May 13, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Tsukasa Yamanaka, Kenichiro Sato
  • Patent number: 7371499
    Abstract: 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: Grant
    Filed: October 19, 2006
    Date of Patent: May 13, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Young-Tae Noh, Yun-Jung Na, Eun-Joon Park
  • Patent number: 7371500
    Abstract: 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: Grant
    Filed: March 28, 2007
    Date of Patent: May 13, 2008
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Takashi Nishioka, Atsushi Itou, Masayoshi Suzuki, Shin-ichirou Iwanaga
  • Patent number: 7368205
    Abstract: 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: Grant
    Filed: August 6, 2004
    Date of Patent: May 6, 2008
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Toshio Banba, Takashi Hirano
  • Patent number: 7368216
    Abstract: 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: Grant
    Filed: January 22, 2007
    Date of Patent: May 6, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Tsukasa Yamanaka
  • Patent number: 7361445
    Abstract: 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: Grant
    Filed: July 6, 2005
    Date of Patent: April 22, 2008
    Assignee: Sumitomo Bakelite Company
    Inventors: Toshio Banba, Takuji Ikeda, Tatsuya Yano, Takashi Hirano
  • Patent number: 7348122
    Abstract: 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 same
    Type: Grant
    Filed: August 29, 2006
    Date of Patent: March 25, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Tsukasa Yamanaka
  • Patent number: 7338737
    Abstract: 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: Grant
    Filed: December 13, 2005
    Date of Patent: March 4, 2008
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hi-Kuk Lee, Yuko Yako, Dong-Ki Lee, Kyu-Young Kim
  • Patent number: 7332254
    Abstract: 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: Grant
    Filed: August 18, 2006
    Date of Patent: February 19, 2008
    Assignee: JSR Corporation
    Inventors: Hirofumi Sasaki, Atsushi Ito, Hirofumi Goto, Yuichi Hashiguchi
  • Patent number: 7297452
    Abstract: 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: Grant
    Filed: December 23, 2005
    Date of Patent: November 20, 2007
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hi-Kuk Lee, Yako Yuko, Kyu-Young Kim
  • Patent number: 7291439
    Abstract: 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: Grant
    Filed: July 7, 2006
    Date of Patent: November 6, 2007
    Assignee: 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
  • Patent number: 7279263
    Abstract: 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: Grant
    Filed: June 20, 2005
    Date of Patent: October 9, 2007
    Assignee: Kodak Graphic Communications Canada Company
    Inventor: Jonathan W. Goodin
  • Patent number: 7255970
    Abstract: 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: Grant
    Filed: July 12, 2005
    Date of Patent: August 14, 2007
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Medhat A. Toukhy, Ping-Hung Lu, Salem K. Mullen
  • Patent number: 7238455
    Abstract: 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: Grant
    Filed: June 23, 2004
    Date of Patent: July 3, 2007
    Assignee: Sumitomo Bakelite Company, Ltd.
    Inventors: Toshio Banba, Takuji Ikeda, Tatsuya Yano, Takashi Hirano
  • Patent number: 7220520
    Abstract: 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 precursor
    Type: Grant
    Filed: June 2, 2006
    Date of Patent: May 22, 2007
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Il'ya Rushkin, Richard Hopla
  • Patent number: 7214455
    Abstract: 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: Grant
    Filed: May 28, 2003
    Date of Patent: May 8, 2007
    Assignee: Toray Industries, Inc.
    Inventors: Kazuto Miyoshi, Ryoji Okuda, Masao Tomikawa
  • Patent number: 7214454
    Abstract: 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: Grant
    Filed: January 15, 2003
    Date of Patent: May 8, 2007
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Takashi Nishioka, Atsushi Itou, Masayoshi Suzuki, Shin-ichirou Iwanaga
  • Patent number: 7195854
    Abstract: 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: Grant
    Filed: July 5, 2005
    Date of Patent: March 27, 2007
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Hoon Kang, Seung-uk Lee, Woo-sik Jun, Dae-youn Park, Ju-hyuk Kim, Byung-uk Kim
  • Patent number: 7195849
    Abstract: 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: Grant
    Filed: March 4, 2004
    Date of Patent: March 27, 2007
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, Pamela J. Waterson, William D. Weber, Ilya Rushkin, Richard Hopla, Jon Metivier
  • Patent number: 7175960
    Abstract: 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: Grant
    Filed: September 9, 2004
    Date of Patent: February 13, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato
  • Patent number: 7144662
    Abstract: 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: Grant
    Filed: February 20, 2002
    Date of Patent: December 5, 2006
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Dong-Ki Lee, Sung-Chul Kang, You-Kyoung Lee, Jin-Ho Ju
  • Patent number: 7132213
    Abstract: 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: Grant
    Filed: July 15, 2004
    Date of Patent: November 7, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuo Masuda, Toshiki Okui
  • Patent number: 7101650
    Abstract: 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: Grant
    Filed: August 20, 2002
    Date of Patent: September 5, 2006
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Byung-Uk Kim, Joon-Yeon Cho, Kyong-Il Kwon, Soo-Jung Park, Jae-Won Yoo
  • Patent number: 7101652
    Abstract: 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: Grant
    Filed: March 9, 2004
    Date of Patent: September 5, 2006
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, Ilya Rushkin, Richard Hopla, Donald Racicot
  • Patent number: 7060410
    Abstract: 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: Grant
    Filed: April 15, 2003
    Date of Patent: June 13, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Ohnishi, Yusuke Nakagawa, Kousuke Doi
  • Patent number: 7056641
    Abstract: 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: Grant
    Filed: July 8, 2005
    Date of Patent: June 6, 2006
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
  • Patent number: 7026080
    Abstract: 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: Grant
    Filed: September 18, 2002
    Date of Patent: April 11, 2006
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tomonari Nakayama, Masakazu Kato, Takayasu Nihira
  • Patent number: 7026091
    Abstract: 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: Grant
    Filed: July 22, 2004
    Date of Patent: April 11, 2006
    Assignee: Industrial Technology Research Institute
    Inventors: Wei-Chan Tseng, Tsing-Tang Song, Chih-Shin Chuang, Kuen-Yuan Hwang, An-Pang Tu
  • Patent number: 7001705
    Abstract: 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: Grant
    Filed: April 18, 2003
    Date of Patent: February 21, 2006
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Tadashi Hatanaka, Takayasu Nihira
  • Patent number: 6984476
    Abstract: 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: Grant
    Filed: April 10, 2003
    Date of Patent: January 10, 2006
    Assignees: Sharp Kabushiki Kaisha, JSR Corporation
    Inventors: Kazuki Kobayashi, Ikuo Sakono, Shinji Shiraki, Hirofumi Sasaki, Kazuaki Niwa
  • Patent number: 6964838
    Abstract: 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: Grant
    Filed: January 4, 2002
    Date of Patent: November 15, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Takako Suzuki, Kenji Maruyama, Satoshi Niikura, Kousuke Doi
  • Patent number: 6939926
    Abstract: 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: Grant
    Filed: February 9, 2004
    Date of Patent: September 6, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6939659
    Abstract: 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: Grant
    Filed: March 4, 2004
    Date of Patent: September 6, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
  • Patent number: 6933087
    Abstract: 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: Grant
    Filed: February 21, 2002
    Date of Patent: August 23, 2005
    Assignee: Toray Industries, Inc.
    Inventors: Mitsuhito Suwa, Kazuto Miyoshi, Masao Tomikawa
  • Patent number: 6929890
    Abstract: 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: Grant
    Filed: April 7, 2004
    Date of Patent: August 16, 2005
    Assignee: Toray Industries, Inc.
    Inventors: Kazuto Miyoshi, Ryoji Okuda, Masao Tomikawa
  • Patent number: 6929891
    Abstract: 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 irr
    Type: Grant
    Filed: March 8, 2004
    Date of Patent: August 16, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ilya Rushkin, Ahmad A. Naiini, Richard Hopla, Pamela J. Waterson, William D. Weber
  • Patent number: 6913865
    Abstract: 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: Grant
    Filed: February 25, 2002
    Date of Patent: July 5, 2005
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 6911293
    Abstract: 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: Grant
    Filed: April 11, 2002
    Date of Patent: June 28, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, Joseph E. Oberlander, Robert R. Plass, Douglas McKenzie
  • Patent number: 6908717
    Abstract: 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: Grant
    Filed: October 9, 2001
    Date of Patent: June 21, 2005
    Assignees: Sumitomo Bakelite Company Limited, Intel Corporation
    Inventors: Takashi Hirano, Shusaku Okaaki, Michael D. Goodner, Robert P. Meagley
  • Patent number: 6905809
    Abstract: 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: Grant
    Filed: April 1, 2003
    Date of Patent: June 14, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventor: J. Neville Eilbeck
  • Patent number: 6893791
    Abstract: 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: Grant
    Filed: September 27, 2002
    Date of Patent: May 17, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: You-Kyoung Lee, Sung-Chul Kang, Jin-Ho Ju, Dong-Ki Lee, Seung-Uk Lee, Hoon Kang