O-quinone Diazide Patents (Class 430/193)
  • Patent number: 8198002
    Abstract: Disclosed is a positive photosensitive resin composition that includes (A) a first polybenzoxazole precursor that includes: a repeating unit of Chemical Formula 1 and a thermally polymerizable functional group at at least one terminal end; (B) a second polybenzoxazole precursor that includes a repeating unit of Chemical Formula 3; (C) a photosensitive diazoquinone compound; (D) a silane compound; and (E) a solvent.
    Type: Grant
    Filed: October 20, 2009
    Date of Patent: June 12, 2012
    Assignee: Cheil Industries Inc.
    Inventors: Doo-Young Jung, Ji-Young Jeong, Hyun-Yong Cho, Yong-Sik Yoo, Min-Kook Chung, Jong-Hwa Lee, Kil-Sung Lee, Myoung-Hwan Cha
  • Patent number: 8158324
    Abstract: 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: Grant
    Filed: February 5, 2008
    Date of Patent: April 17, 2012
    Assignee: TORAY Industries, Inc.
    Inventors: Yoji Fujita, Shinji Arimoto, Rinsei Ike
  • Patent number: 8080350
    Abstract: Disclosed is a positive photosensitive resin composition containing (A) an alkali-soluble resin, (B) a diazoquinone compound, (d1) an activated silicon compound and (d2) an aluminum complex. Also disclosed is a positive photosensitive resin composition containing (A) an alkali-soluble resin, (B) a diazoquinone compound, (C) a compound having two or more oxetanyl groups in one molecule and (D) a catalyst for accelerating the ring-opening reaction of the oxetanyl groups of the compound (C).
    Type: Grant
    Filed: November 17, 2006
    Date of Patent: December 20, 2011
    Assignee: Sumitomo Bakelite Company, Ltd.
    Inventors: Toshio Banba, Ayako Mizushima
  • Patent number: 8034529
    Abstract: 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: Grant
    Filed: July 19, 2006
    Date of Patent: October 11, 2011
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Ken Sawabe, Takeshi Nojiri
  • Patent number: 8012664
    Abstract: 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: Grant
    Filed: November 6, 2006
    Date of Patent: September 6, 2011
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Wolfgang Zahn, Ralf Grottenmüller, Dieter Wagner
  • Patent number: 7955784
    Abstract: A photoresist composition includes about 100 parts by weight of resin mixture including novolak resin and acryl resin and about 10 parts to about 50 parts by weight of naphthoquinone diazosulfonic acid ester. A weight-average molecular weight of the novolak resin is no less than about 30,000. A weight-average molecular weight of the acryl resin is no less than about 20,000. The acryl resin makes up about 1% to about 15% of the total weight of the resin mixture. When a photoresist film formed using the photoresist composition is heated, a profile variation of the photoresist composition is relatively small. Therefore, a residual photoresist film has a uniform thickness, and a short circuit and/or an open defect in a TFT substrate may be reduced.
    Type: Grant
    Filed: October 30, 2006
    Date of Patent: June 7, 2011
    Assignees: Samsung Electronics Co., Ltd., AZ Electronic Materials (Japan) K.K.
    Inventors: Hi-Kuk Lee, Woo-Seok Jeon, Doo-Hee Jung, Jeong-Min Park, Deok-Man Kang, Si-Young Jung, Jae-Young Choi
  • Patent number: 7932012
    Abstract: A heat resistant photosensitive resin composition having excellent film properties is provided by constituting a photosensitive resin composition containing (A) a polymer having an acid functional group and/or a substituent derived therefrom, (B) a compound having at least one substituent derived from an amine functional group, (C) a photoreactive compound, and (D) a solvent. Using this composition, a pattern with high resolution can be produced, and thus an electronic part having a high quality can be produced.
    Type: Grant
    Filed: March 31, 2004
    Date of Patent: April 26, 2011
    Assignee: Hitachi Chemical Dupont Microsystems Ltd.
    Inventors: Hiroshi Komatsu, Nagatoshi Fujieda, Hajime Nakano
  • Patent number: 7910281
    Abstract: A positive resist composition for a thin-film implantation process of the present invention includes: a resin component (A) with an acid-dissociable dissolution inhibiting group, whose alkali solubility increases by the action of an acid; an acid generator component (B) which generates an acid by irradiation with radiation; and a compound (C) having a radiation absorbing ability, wherein said resin component (A) comprises a structural unit (a1) derived from a hydroxystyrene and a structural unit (a2) obtained by substituting the hydrogen atom in a hydroxyl group of said structural unit (a1) with an acid-dissociable dissolution inhibiting group, and said acid-dissociable dissolution inhibiting group contains an acid-dissociable dissolution inhibiting group (II) represented by the following general formula (II) as a main component.
    Type: Grant
    Filed: February 1, 2006
    Date of Patent: March 22, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Ken Tanaka, Koji Yonemura, Shoichi Fujita
  • Patent number: 7858275
    Abstract: A positive photosensitive resin composition with favorable heat resistance and transparency is provided. The photosensitive resin composition contains a resin component (A1) having a structural unit (a1?) obtained by substituting at least a portion of hydrogen atoms of phenolic hydroxyl groups within a structural unit represented by a general formula (a1) shown below with a naphthoquinone-1,2-diazide-5-(and/or -4-) sulfonyl group. (In the above general formula, R0 represents a hydrogen atom or methyl group, R1 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R2 represents an alkyl group of 1 to 5 carbon atoms, a represents an integer from 1 to 5, b represents either 0 or an integer from 1 to 4, and a+b is no greater than 5. If two or more R2 groups exist, then these R2 groups may be either the same or mutually different.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: December 28, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Ohnishi, Yasuaki Sugimoto, Isao Tateno, Masaru Shida
  • Patent number: 7851121
    Abstract: There is provided a photosensitive composition including a polyimide or polyimide precursor. The polyimide and polyimide precursor of the present invention includes a group of a first acid-cleavable group, a first base-cleavable group or a first thermally-cleavable group, and another group of a hydrophilic group, or a protected hydrophilic group by a second acid-cleavable group, a second base-cleavable group, or a crosslinkable group.
    Type: Grant
    Filed: February 10, 2006
    Date of Patent: December 14, 2010
    Assignees: Central Glass Co., Ltd., Georgia Tech Research Corporation
    Inventors: Kazuhiro Yamanaka, Michael Romeo, Clifford Henderson, Kazuhiko Maeda
  • Patent number: 7847003
    Abstract: 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: Grant
    Filed: July 28, 2004
    Date of Patent: December 7, 2010
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Shinsuke Tsuji, Yosuke Iinuma, Shinya Arase
  • Patent number: 7803510
    Abstract: A heat resistant positive-working photosensitive PBO precursor composition comprising: (a) at least one polybenzoxazole precursor polymer; (a) at least one plasticizer compound; (b) at least one solvent; wherein the amount of the plasticizer present in the composition is an amount effective to reduce the sidewall angle of imaged and cured features in the coated film on the substrate to prevent stress failures in subsequent metallization of the substrate due to steep angles of the imaged features, and with the proviso that if the polybenzoxazole precursor polymer solely consists of polybenzoxazole precursor polymers that do not contain a photoactive moiety on the polymer, then (c) at least one photoactive compound is also present in the composition.
    Type: Grant
    Filed: August 7, 2006
    Date of Patent: September 28, 2010
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, Donald W. Racicot, Il'ya Rushkin, William D. Weber
  • Patent number: 7799509
    Abstract: A photosensitive resin composition for an organic layer pattern includes about 100 parts by weight of an acryl-based copolymer and about 5 to about 100 parts by weight of a 1,2-quinonediazide compound. The acryl-based copolymer is prepared by copolymerizing about 5 to about 60 percent by weight of an isobonyl carboxylate-based compound based on a total weight of the acryl-based copolymer, about 10 to about 30 percent by weight of an unsaturated compound carrying an epoxy group, about 20 to about 40 percent by weight of an olefin-based unsaturated compound, and about 10 to about 40 percent by weight of one selected from unsaturated carboxylic acid, unsaturated carboxylic acid anhydride, and a mixture thereof. Methods of manufacturing a TFT substrate and a common electrode substrate using the photosensitive resin composition are also provided. Advantageously, the organic layer pattern may have a mountain structure having an improved local flatness without concave and convex structures.
    Type: Grant
    Filed: June 2, 2006
    Date of Patent: September 21, 2010
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hi-Kuk Lee, Dong-Ki Lee, Jae-Sung Kim, Byung-Uk Kim, Hyoc-Min Youn, Ki-Hyuk Koo, Joo-Pyo Yun, Sang-Gak Choi
  • Patent number: 7790345
    Abstract: 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: Grant
    Filed: December 7, 2005
    Date of Patent: September 7, 2010
    Assignee: Kolon Industries, Inc.
    Inventors: Byoung-Kee Kim, Se-Hyung Park, Jong-Min Park, Seong-In Baek
  • Patent number: 7781131
    Abstract: 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: Grant
    Filed: August 20, 2008
    Date of Patent: August 24, 2010
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventor: Hiroaki Makabe
  • Patent number: 7777184
    Abstract: A method for photoresist characterization includes forming a photoresist on a supportive structure; and characterizing the photoresist using a metrology tool selected from the group consisting of a transmission electron microscope (TEM), a scanning electron microscope (SEM), an atomic force microscope (AFM), a small angle X-ray scattering (SAXS) and a laser diffraction particle analyzer.
    Type: Grant
    Filed: October 2, 2007
    Date of Patent: August 17, 2010
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Hsiao-Wei Yeh, Jen-Chieh Shih
  • Patent number: 7749676
    Abstract: 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: Grant
    Filed: December 7, 2005
    Date of Patent: July 6, 2010
    Assignee: Kolon Industries, Inc.
    Inventors: Se-Hyung Park, Byoung-Kee Kim, Jong-Min Park, Seong-In Baek
  • Patent number: 7740996
    Abstract: A positive photosensitive resin composition exhibiting excellent heat resistance is provided, which comprises an alkali-soluble resin component (A) and a photosensitizer (B), the component (A) including a resin component (A1) having a structural unit (a1) represented by general formula (a1) shown below: wherein R0 represents a hydrogen atom or a methyl group; R1 represents a single bond or an alkylene group of 1 to 5 carbon atoms; R2 represents an alkyl group of 1 to 5 carbon atoms; and a represents an integer of 1 to 5, and b represents 0 or an integer of 1 to 4, with the proviso that the sum of a and b is 5 or less, and when two or more R2 are present, R2 may be the same or different.
    Type: Grant
    Filed: December 2, 2005
    Date of Patent: June 22, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Ohnishi, Yasuaki Sugimoto
  • Patent number: 7687208
    Abstract: A positive photosensitive resin composition excellent in sensitivity and resolution, characterized by comprising 100 parts by mass of (A) a hydroxypolyamide comprising repeating units represented by the general formula (1), 1 to 50 parts by mass of (B) a photoacid generator, 5 to 20 parts by mass of (C) a carboxylic acid compound having 6 to 18 carbon atoms as represented by the general formula (2), and 0.01 to 70 parts by mass of (D) an alcohol having 4 to 14 carbon atoms as represented by the general formula (3).
    Type: Grant
    Filed: August 10, 2007
    Date of Patent: March 30, 2010
    Assignee: Asahi Kasei EMD Corporation
    Inventor: Satoshi Shibui
  • Patent number: 7678514
    Abstract: A positive-type photosensitive resin composition that exhibits excellent adhesion to a substrate after a humidification treatment includes (A) an alkali-soluble resin, (B) a photosensitive diazoquinone compound, and (C-1) a silicon compound shown by the following formula (1), wherein R1 and R2 represent alkyl groups having 1 to 10 carbon atoms, R3 represents an organic group, and R4 represents an alkylene group having 1 to 10 carbon atoms, and i represents an integer from 0 to 2.
    Type: Grant
    Filed: December 24, 2008
    Date of Patent: March 16, 2010
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Hiromichi Sugiyama, Toshio Banba, Shusaku Okamyo
  • Patent number: 7674566
    Abstract: The present invention provides a positive photosensitive resin composition, characterized by comprising 1 to 50 parts by mass of a photo-acid generator and 0.01 to 70 parts by mass of a terpene compound in combination with 100 parts by mass of a hydroxypolyamide having repeating units. A terpene compound can be combined with a hydroxypolyamide having a particular structure to provide a positive photosensitive resin composition excellent in positive lithography performance such as sensitivity and resolution.
    Type: Grant
    Filed: October 20, 2006
    Date of Patent: March 9, 2010
    Assignee: Asahi Kasei EMD Corporation
    Inventor: Satoshi Shibui
  • Patent number: 7638254
    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: September 10, 2008
    Date of Patent: December 29, 2009
    Assignee: Hitachi Chemical Dupont Microsystems Ltd
    Inventors: Takashi Hattori, Yasuharu Murakami, Hiroshi Matsutani, Masayuki Ooe, Hajime Nakano
  • Patent number: 7638253
    Abstract: In one example, a photoresist composition includes about 1 to about 70 parts by weight of a first binder resin including a repeat unit represented by the following Chemical Formula 1, about 1 to about 70 parts by weight of a second binder resin including a repeat unit represented by the following Chemical Formula 2, about 0.5 to about 10 parts by weight of a photo-acid generator, about 1 to about 20 parts by weight of a cross-linker and about 10 to about 200 parts by weight of a solvent. The photoresist composition may improve the heat resistance and adhesion ability of a photoresist pattern. wherein R1 and R2 independently represent an alkyl group having 1 to 5 carbon atoms, and n and m independently represent a natural number.
    Type: Grant
    Filed: April 11, 2008
    Date of Patent: December 29, 2009
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jeong-Min Park, Doo-Hee Jung, Hi-Kuk Lee, Hyoc-Min Youn, Ki-Hyuk Koo
  • Patent number: 7635551
    Abstract: A poly(imide-azomethine)copolymer that has a low linear thermal expansion coefficient and a method for producing the same copolymer are provided. Also provided are a poly(amic acid-azomethine)copolymer that is a precursor polymer of the poly(imide-azomethine)copolymer; a positive photosensitive resin composition composed of the precursor polymer and a photosensitizer; and a method for making a fine pattern of poly(imide-azomethine) copolymer from the resin composition.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: December 22, 2009
    Assignees: Sony Corporation, Sony Chemical & Information Device Corporation
    Inventors: Masatoshi Hasegawa, Junichi Ishii
  • Patent number: 7629091
    Abstract: A polyimide compound has a low coefficient of linear thermal expansion comparable to the coefficient of linear thermal expansion of a conductor to be covered by the polyimide. The polyimide compound is less susceptible to contraction caused by dehydration process. The compound is obtained by the reaction of a highly linear acid dianhydride with a highly linear diamine and has a high imidization rate. Having a low coefficient of linear thermal expansion comparable to the conductor to be covered by the polyimide, the polyimide compound of the present invention is less susceptible to contraction that occurs during polyimide formation. The polyimide compound is suitable for making curl-free flexible wiring boards.
    Type: Grant
    Filed: October 28, 2005
    Date of Patent: December 8, 2009
    Assignees: Sony Corporation, Sony Chemical and Device Information
    Inventors: Junichi Ishii, Tadashi Akamatsu
  • Patent number: 7615331
    Abstract: A photosensitive resin composition contains: a polymer represented by the formula (I) as defined herein, in which 0.5 mol % or more of A in the polymer represented by the formula (I) is a protective group; a photosensitizing agent; a compound containing a methacryloyl or acryloyl group within a molecule of the compound; and a solvent.
    Type: Grant
    Filed: September 7, 2007
    Date of Patent: November 10, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Tsukasa Yamanaka, Kenichiro Sato
  • Patent number: 7615324
    Abstract: A photosensitive resin composition includes (a) a resin comprising a repeating unit represented by a following formula (1); (b) a photosensitive agent; (c) a thermo-acid generator; and (d) a compound having at least one of an alkoxymethyl group and an acyloxymethyl group, wherein R1 represents a divalent to octavalent organic group containing 2 or more carbon atoms, R2 represents a divalent to hexavalent organic group containing 2 or more carbon atoms, each of R0 and R3 independently represents a hydrogen atom or an organic group containing 1 to 20 carbon atoms, m represents an integer of 0 to 2, and each of p and q represents an integer of 0 to 4, provided that p+q>0.
    Type: Grant
    Filed: March 14, 2008
    Date of Patent: November 10, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Naoya Sugimoto
  • Patent number: 7598009
    Abstract: According to the present invention, there is provided: a photosensitive resin composition comprising a polyamide resin having a specific structure, a photosensitive agent, and a compound having at least two sulfonate ester groups; a production method for a cured relief pattern using the photosensitive resin composition; and a semiconductor device containing the cured relief pattern formed according to the production method.
    Type: Grant
    Filed: July 30, 2008
    Date of Patent: October 6, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Naoya Sugimoto
  • Patent number: 7592119
    Abstract: The developability of a photosensitive polyimide resin composition with a weakly alkaline aqueous solution is improved without reduction in the solubility in general-purpose organic solvents even when a part of the diamine component is replaced with a diaminopolysiloxane-based compound or a bis(aminobenzoate)-based compound in order to reduce the warpage characteristics of the photosensitive polyimide resin composition by reducing its modulus of elasticity. The photosensitive polyimide resin composition is capable of being developed in a positive manner with a weakly alkaline aqueous solution and is soluble in an organic solvent. The photosensitive polyimide resin composition contains: a polyimide resin including a polyimide unit represented by formula (1) and a polyimide unit represented by one of formulas (2) and (3); an analogue of melamine cyanurate; and an analogue of diazonaphthoquinone.
    Type: Grant
    Filed: January 23, 2008
    Date of Patent: September 22, 2009
    Assignees: Sony Corporation, Sony Chemical & Information Device Corporation
    Inventor: Mamiko Nomura
  • Patent number: 7524594
    Abstract: Some embodiments in accordance with the present invention relate to norbornene-type polymers and to photosensitive dielectric resin compositions formed therefrom. Other embodiments relate to films formed from such compositions and to devices, such as electrical, electronic and optoelectronic devices, that encompass such films.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: April 28, 2009
    Assignee: Promerus LLC
    Inventors: Dino Amoroso, Brian Bedwell, Andrew Bell, Edmund Elce, Rajesh Raja Puthenkovilakom, Ramakrishna Ravikiran, Robert Shick, Xiaoming Wu, Hiroaki Makabe, Yasunori Takahashi, Etsu Takeuchi, Daoji Gan, Seok Ho Kang
  • Patent number: 7521167
    Abstract: Provided are an ester group-containing poly(imide-azomethine)copolymer having low linear thermal expansion coefficient; a production method thereof; an ester group-containing poly(amide acid-azomethine)copolymer to serve as the precursor of the poly(imide-azomethine)copolymer; a positive photosensitive composition including the poly(amide acid-azomethine)copolymer and a photosensitizer; a method for forming a fine pattern of an ester group-containing poly(imide-azomethine)copolymer from the composition; and a method for forming a fine pattern of an ester group-containing poly(imide-azomethine)copolymer by etching a photosensitizer-free, ester group-containing poly(imide-azomethine)copolymer in an alkaline solution.
    Type: Grant
    Filed: May 15, 2006
    Date of Patent: April 21, 2009
    Assignees: Sony Corporation, Sony Chemical & Information Device Corporation
    Inventors: Masatoshi Hasegawa, Junichi Ishii
  • Patent number: 7507518
    Abstract: 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: Grant
    Filed: July 7, 2004
    Date of Patent: March 24, 2009
    Assignee: Toray Industries, Inc.
    Inventors: Yoji Fujita, Tomoyuki Yuba, Mitsuhito Suwa
  • 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: 7439005
    Abstract: There is disclosed a photosensitive resin composition for interlayer insulating films, surface protection films or the like, which exhibits excellent resolution and can be developed with an aqueous alkaline solution. The photosensitive resin composition is prepared using a polymer at least having a constitutional repeating unit represented by general formula II: wherein R1 represents hydrogen atom or methyl group; R2 to R9 independently represent hydrogen atom, halogen atom or alkyl group having 1 to 4 carbon atoms; X represents —CH?N—, —CONH—, —(CH2)n—CH?N— or —(CH2)n—CONH— and the N atom in X is bonded to a carbon atom in the benzene ring having AO— at an o-position; A represents hydrogen atom or a group being decomposed by an acid; and n represents a positive integer of 1 to 3.
    Type: Grant
    Filed: February 25, 2005
    Date of Patent: October 21, 2008
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Kaichiro Nakano
  • 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: RE41083
    Abstract: 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: Grant
    Filed: July 26, 2005
    Date of Patent: January 19, 2010
    Assignee: Eastman Kodak Company
    Inventor: Mathias Jarek