Radiation-sensitive Composition Patents (Class 430/170)
  • Patent number: 10450417
    Abstract: Provided is a resin capable of yielding a cured film with less warp and good uniformity, and of yielding a cured film (pattern) with less scum; a composition using the resin; a cured film; and a method for manufacturing a cured film and a semiconductor device. The resin is selected from polyimide precursor, polyimide, polybenzoxazole precursor, and, polybenzoxazole, and has a polymerizable group, and has a total content of a component with a molecular weight of 1,000 or smaller of 0.005 to 1.0% by mass.
    Type: Grant
    Filed: March 28, 2018
    Date of Patent: October 22, 2019
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Yu Iwai, Akinori Shibuya
  • Patent number: 10377692
    Abstract: A photoresist composition comprising a resin which comprises a structural unit derived from a compound having an acid-labile group and which is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, an acid generator and a compound represented by the formula (I?): wherein R51, R52, R53 and R54 independently each represent a C1-C8 alkyl group, and A11 represents a C3-C36 divalent saturated cyclic hydrocarbon group which can contain one or more heteroatoms and which have one or more substituents or a C6-C20 divalent aromatic hydrocarbon group which can contain one or more heteroatoms and which have one or more substituents.
    Type: Grant
    Filed: September 3, 2010
    Date of Patent: August 13, 2019
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Akira Kamabuchi, Yuko Yamashita
  • Patent number: 10202493
    Abstract: Provided are a thermosetting resin composition which is soluble in a general-purpose solvent and which can obtain a cured product (cured film) having high optical transparency to the ultraviolet region (approximately 300 nm) from the visible region, and a polyamide-imide resin suitable for use in preparing the thermosetting resin composition. Specifically, provided are an alcohol-modified polyamide-imide resin, which is obtained by reacting an isocyanurate type polyisocyanate (a1) synthesized from an isocyanate having an aliphatic structure with a tricarboxylic anhydride (a2) to prepare a polyamide-imide resin (a), and then reacting the polyamide-imide resin (a) with an alcohol compound (b); a curable resin composition containing the polyamide-imide resin; and a cured product of the curable resin composition.
    Type: Grant
    Filed: July 15, 2014
    Date of Patent: February 12, 2019
    Assignee: DIC Corporation
    Inventors: Kouichi Murakami, Atsushi Miyagaki
  • Patent number: 10120278
    Abstract: A carboxylic acid onium salt of formula (1) exerts a satisfactory acid diffusion control (or quencher) function. A resist composition comprising the carboxylic acid onium salt can be processed by DUV or EUV lithography to form a resist pattern with improved resolution, reduced LWR and minimal defects after development.
    Type: Grant
    Filed: April 17, 2017
    Date of Patent: November 6, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masahiro Fukushima, Kazuhiro Katayama
  • Patent number: 9944804
    Abstract: A water washable resin formulation for 3D printing having at least one water-soluble and/or water-dispersible ingredient such as an oligomer and/or monomer. In one example, a water-soluble ingredient is greater than 1% by weight of the resin formulation. A water-soluble or water-dispersible filler may also be used as an ingredient in the resin formulation. The water-washable photopolymer resin formulation allows printed 3D objects to be cleaned with water rather than organic solvents. Because the water-washable photopolymer resin formulation is insoluble when cured, only the uncured water-washable photopolymer resin formulation is washed away. Depending on the filler's property and compatibility with the other ingredients of the resin formulation, the blending of filler therein can be used to modify the mechanical and chemical properties of the printed 3D objects.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: April 17, 2018
    Inventors: Henry Liu, Chunlin He
  • Patent number: 9944805
    Abstract: A water washable resin formulation for 3D printing having at least one water-soluble and/or water-dispersible ingredient such as an oligomer and/or monomer. In one example, a water-soluble ingredient is greater than 1% by weight of the resin formulation. A water-soluble or water-dispersible filler may also be used as an ingredient in the resin formulation. The water-washable photopolymer resin formulation allows printed 3D objects to be cleaned with water rather than organic solvents. Because the water-washable photopolymer resin formulation is insoluble when cured, only the uncured water-washable photopolymer resin formulation is washed away. Depending on the filler's property and compatibility with the other ingredients of the resin formulation, the blending of filler therein can be used to modify the mechanical and chemical properties of the printed 3D objects.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: April 17, 2018
    Inventors: Henry Liu, Chunlin He
  • Patent number: 9921480
    Abstract: The present disclosure provides a method for lithography patterning in accordance with some embodiments. The method includes forming a photoresist layer over a substrate; performing an exposing process to the photoresist layer; and developing the photoresist layer, thereby forming a patterned photoresist layer. The photoresist layer includes a polymer backbone, an acid labile group (ALG) bonded to the polymer backbone, a first sensitizer that is bonded to the polymer backbone, a second sensitizer that is not bonded to the polymer backbone, and a photo-acid generator (PAG).
    Type: Grant
    Filed: February 10, 2016
    Date of Patent: March 20, 2018
    Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD
    Inventors: Wei-Han Lai, Ching-Yu Chang, Chien-Wei Wang
  • Patent number: 9911591
    Abstract: Methods of depositing a film selectively onto a first substrate surface relative to a second substrate surface. Methods include soaking a substrate surface comprising hydroxyl-terminations with a silylamine to form silyl ether-terminations and depositing a film onto a surface other than the silyl ether-terminated surface.
    Type: Grant
    Filed: April 29, 2016
    Date of Patent: March 6, 2018
    Assignee: APPLIED MATERIALS, INC.
    Inventors: David Thompson, Mark Saly, Bhaskar Jyoti Bhuyan
  • Patent number: 9891546
    Abstract: An ultraviolet-curable liquid developer containing a cationically polymerizable liquid monomer, a photoinitiator according to formula (1), and a toner particle. In the developer the cationically polymerizable liquid monomer contains a vinyl ether compound, the molar average SP value of the cationically polymerizable liquid monomer is not more than 9.0, the molar average number of functional groups for the cationically polymerizable liquid monomer is at least 1.8, the photoinitiator contains a specified compound, and the content of the specified compound is at least 0.01 mass parts and not more than 5.00 mass parts per 100 mass parts of the cationically polymerizable liquid monomer.
    Type: Grant
    Filed: May 27, 2016
    Date of Patent: February 13, 2018
    Assignee: CANON KABUSHIKI KAISHA
    Inventors: Junji Ito, Yasuhiro Aichi, Naotake Sato, Hiroshi Tanabe
  • Patent number: 9885955
    Abstract: A thinner composition including an acetate-based compound in an amount in a range of about 30 weight percent to about 70 weight percent, a lactate-based compound in an amount in a range of about 1 weight percent to about 20 weight percent, a propionate-based compound in an amount in a range of about 30 weight percent to about 60 weight percent, and an ether-based additive in an amount in a range of about 10 ppm to about 500 ppm, based on a total amount of the composition.
    Type: Grant
    Filed: January 11, 2016
    Date of Patent: February 6, 2018
    Assignees: Samsung Electronics Co., Ltd., Dongwoo Fine-Chem
    Inventors: Ahn-Ho Lee, Seung-Hyun Ahn, Jin-Seok Yang, Sang-Tae Kim, Shi-Jin Sung, Kyong-Ho Lee
  • Patent number: 9588424
    Abstract: A photosensitive resin composition is prepared by dispersing at least one of a hydrophobic polymer and a mixture of an oil-soluble photopolymerization initiator and a water-insoluble or sparingly water-soluble compound having at least one photoactive, ethylenically unsaturated group in an aqueous solution that contains both a water-soluble polymer and a diazo resin is obtained by condensing a water-soluble salt of an optionally substituted 4-diazodiphenylamine with formaldehyde in the presence of sulfuric acid and phosphoric acid. This photosensitive resin composition gives a photosensitive film having excellent stability over time and a wide exposure latitude. By adding a specific fluorine compound to the photosensitive resin composition, a screen plate has an excellent discharge performance.
    Type: Grant
    Filed: September 25, 2012
    Date of Patent: March 7, 2017
    Assignee: SUNTYPE CO., LTD.
    Inventors: Yoshio Umeda, Kenji Ota, Yuichi Ono, Taichi Okada, Yukina Kuwahara, Takafumi Somei, Setsuka Nakajima, Masataka Miyazaki, Toru Mori, Suguru Komatsu, Michihiro Iljima
  • Patent number: 9551928
    Abstract: According to one embodiment, An actinic-ray- or radiation-sensitive resin composition comprises a basic compound (C) having n basic groups and m groups that when exposed to actinic rays or radiation, generate an acid, provided that n and m satisfy the relationships n?1, m?2 and n<m.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: January 24, 2017
    Assignee: FUJIFILM Corporation
    Inventors: Shuhei Yamaguchi, Hisamitsu Tomeba, Mitsuhiro Fujita
  • Patent number: 9551933
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising: (A) a resin containing a repeating unit represented by the first specific formula and a repeating unit represented by the second specific formula, wherein the content of the repeating unit represented by the first specific formula is 35 mol % or more based on all repeating units in the resin (A), a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition.
    Type: Grant
    Filed: January 26, 2015
    Date of Patent: January 24, 2017
    Assignee: FUJIFILM Corporation
    Inventors: Hiroo Takizawa, Shuji Hirano, Natsumi Yokokawa, Wataru Nihashi
  • Patent number: 9405200
    Abstract: A method of forming a resist pattern, including: a step (1) in which a resist film is formed by coating a resist composition including a base component (A) that exhibits increased solubility in an alkali developing solution, a photo-base generator component (C) that generates a base upon exposure, an acid supply component (Z) and a compound (F) containing at least one selected from the group consisting of a fluorine atom and a silicon atom and containing no acid decomposable group which exhibits increased polarity by the action of acid on a substrate; a step (2) in which the resist film is subjected to exposure; a step (3) in which baking is conducted after the step (2); and a step (4) in which the resist film is subjected to an alkali development, thereby forming a negative-tone resist pattern, and a resist composition used in the step (1).
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: August 2, 2016
    Assignee: TOYKO OHKA KOGYO CO., LTD.
    Inventors: Tsuyoshi Nakamura, Jiro Yokoya, Hiroaki Shimizu, Hideto Nito
  • Patent number: 9188862
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, which is excellent in sensitivity, resolution, a pattern profile and a depth of focus (DOF), and, an actinic ray-sensitive or radiation-sensitive film and a pattern forming method, each using the same, are provided. The actinic ray-sensitive or radiation-sensitive resin composition includes a nitrogen-containing compound and a resin (Ab) capable of varying a polarity or an alkali solubility thereof by the action of an acid.
    Type: Grant
    Filed: June 12, 2014
    Date of Patent: November 17, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Shuji Hirano, Hiroo Takizawa, Hideaki Tsubaki
  • Patent number: 9182663
    Abstract: A photoresist composition comprising: a resin which shows an increase in solubility in an aqueous alkali solution by an action of an acid; an acid generator; a compound represented by formula (I); and a solvent the amount of which is from 40 to 75% by mass of the total amount of the photoresist composition: wherein the ring W1 is a nitrogen-containing heterocyclic ring, or a benzene ring having a substituted or unsubstituted amino group, A1 represents a phenyl group or a naphtyl group, and n represents an integer of 2 or 3.
    Type: Grant
    Filed: May 28, 2013
    Date of Patent: November 10, 2015
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masako Sugihara, Maki Kawamura
  • Patent number: 8846295
    Abstract: The present invention relates to a photoresist composition capable of negative development and a pattern forming method using the photoresist composition. The photoresist composition includes an imaging polymer, a crosslinking agent and a radiation sensitive acid generator. The imaging polymer includes a monomeric unit having an acid-labile moiety-substituted hydroxyl group. The patterning forming method utilizes an organic solvent developer to selectively remove an unexposed region of a photoresist layer of the photoresist composition to form a patterned structure in the photoresist layer. The photoresist composition and the pattern forming method are especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.
    Type: Grant
    Filed: April 27, 2012
    Date of Patent: September 30, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Wu-Song Huang, Wai-Kin Li
  • Patent number: 8741542
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition comprising (A) a specific compound represented by a general formula, (B) a resin which is alkali-insoluble or sparingly alkali-soluble and becomes easily alkali-soluble in the presence of an acid, and (C) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; a film formed using the composition; and a pattern forming method using the same.
    Type: Grant
    Filed: November 30, 2010
    Date of Patent: June 3, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Takayuki Ito, Toru Fujimori, Kana Fujii
  • Patent number: 8632943
    Abstract: An infrared sensitive, positive-working, image forming composition and element are disclosed. The image forming composition comprises a 1,1-di[(alkylphenoxy)ethoxy]cyclohexane, an infrared absorbing dye having a maximum absorption peak in the range of from about 700 nm to about 1100 nm, and a novolac polymer. The composition is applied and dried on a planar, hydrophilic substrate to form an image forming element, in particular, a planographic printing plate. Upon imagewise exposure to a near-infrared radiation source, the infrared dye absorbs light in the exposed areas and converts it to heat, which causes a disruption in the matrix of the image forming composition. Upon development with an aqueous alkaline developer, the exposed areas are removed while the nonexposed areas remain, thus forming a positive image.
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: January 21, 2014
    Assignee: Southern Lithoplate, Inc.
    Inventors: Stephan J. W. Platzer, James A. Bonham, Kimberly R. Kukla, Richard C. Wax, Teresa Baker, Ella Ross Ryan
  • Patent number: 8617784
    Abstract: Two acids may be formed per exposed photon using free radical promotion so that two acid products are produced via two parallel pathways. This results in increased fabrication facility throughput. In some embodiments, this may be achieved while reducing side-lobe defect liability.
    Type: Grant
    Filed: May 26, 2006
    Date of Patent: December 31, 2013
    Assignee: Intel Corporation
    Inventors: David Fryer, Vivek Singh, Nikolay Suetin, Alex A. Granovsky
  • Patent number: 8541534
    Abstract: A resin composition for laser engraving, including: a compound (A) having at least one of a hydrolyzable silyl group or a silanol group; and a binder polymer (B) having a functional group capable of forming a crosslinked structure by reacting with at least one of a hydrolyzable silyl group or a silanol group.
    Type: Grant
    Filed: February 5, 2010
    Date of Patent: September 24, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Atsushi Sugasaki, Takashi Kawashima
  • Patent number: 8198007
    Abstract: This disclosure provides a negative-working resist composition comprising a calix resorcinarene derivative (A) of specific structure, an acid generator (B) which directly or indirectly generates an acid when exposed to an active energy ray having a wavelength of 248 nm or less, and a cross-linking agent (C).
    Type: Grant
    Filed: November 5, 2008
    Date of Patent: June 12, 2012
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Kenichi Okuyama, Satoru Kanke
  • Patent number: 8053158
    Abstract: Disclosed herein are compositions useful in forming organic active patterns that may, in turn, be incorporated in organic memory devices. The compositions comprise N-containing conjugated electroconductive polymer(s), photoacid generator(s) and organic solvent(s) capable of dissolving suitable quantifies of both the electroconductive polymer and the photoacid generator. Also disclosed are methods for patterning organic active layers formed using one or more of the compositions to produce organic active patterns, portions of which may be arranged between opposed electrodes to provide organic memory cells. The methods include directly exposing and developing the organic active layer to obtain fine patterns without the use of a separate masking pattern, for example, a photoresist pattern, thereby tending to simplify the fabrication process and reduce the associated costs.
    Type: Grant
    Filed: January 19, 2007
    Date of Patent: November 8, 2011
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang Kyun Lee, Won Jae Joo, Kwang Hee Lee, Tae Lim Choi, Myung Sup Jung
  • Patent number: 7794913
    Abstract: A chemically amplified positive resist composition comprising (A) a resin which comprises (i) a polymerization unit represented by the formula (I): (ii) a polymerization unit represented by the formula (II): and (iii) at least one polymerization unit selected from the group consisting of a polymerization unit represented by the formula (III): and a polymerization unit represented by the formula (IV): and (B) at least one acid generator.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: September 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Masumi Suetsugu, Kazuhiko Hashimoto
  • 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: 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: 7638264
    Abstract: A positive photoresist composition comprises a radiation sensitive acid generator, and a polymer that includes a first repeating unit derived from a sulfonamide monomer including a fluorosulfonamide functionality, a second repeating unit having a pendant acid-labile moiety, and a third repeating unit having a lactone functionality. The positive photoresist composition may be used to form patterned features on a substrate, such as those used in the manufacture of a semiconductor device.
    Type: Grant
    Filed: May 23, 2006
    Date of Patent: December 29, 2009
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi
  • Patent number: 7592118
    Abstract: A positive resist composition, includes: (B) a resin containing a repeating unit represented by formula (Ia) or (Ib) as defined in the specification, which decomposes under an action of an acid to increase a solubility of the resin (B) in an aqueous alkali solution; and (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and a pattern forming method uses the composition.
    Type: Grant
    Filed: March 24, 2008
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Shuji Hirano, Shinichi Sugiyama
  • Patent number: 7468228
    Abstract: A light shielding film for a display device, comprising a polymer binder, metal particles dispersed in the polymer binder, and a compound including a sulfur atom or a nitrogen atom. A substrate for a display device comprising the light shielding film. And a color filter comprising the light shielding film.
    Type: Grant
    Filed: February 4, 2005
    Date of Patent: December 23, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Akira Hatakeyama
  • Patent number: 7399576
    Abstract: Radiation-sensitive compositions can be used to prepare imageable elements useful for example to make lithographic printing plates. The compositions include an aqueous alkaline solvent soluble phenolic resin or poly(vinyl acetal) as a polymeric binder. The compositions also include a fluorinated compound that has a urethane moiety and a fluorinated alkyleneoxy moiety to provide improved coating and friction properties particularly when stacked with interleaf papers. The radiation-sensitive composition can be coated as an imageable layer that further includes a radiation absorbing compound that is sensitive, for example, to infrared radiation.
    Type: Grant
    Filed: February 28, 2007
    Date of Patent: July 15, 2008
    Assignee: Eastman Kodak Company
    Inventor: Moshe Levanon
  • Patent number: 7381516
    Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: June 3, 2008
    Assignee: 3M Innovative Properties Company
    Inventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
  • Patent number: 7364831
    Abstract: A positive resist composition includes a resin component (A) whose alkaline solubility changes by an action of an acid, an acid generator component (B), and polypropylene glycol, wherein the component (A) includes a resin component (A1) including a constitutional unit (a1) represented by general formula (I), a constitutional unit (a2) represented by general formula (II), and a constitutional unit (a3) having an acid dissociable dissolution inhibiting group, wherein R represents a hydrogen atom or a methyl group, and m represents an integer of 1 to 3, wherein R represents a hydrogen atom or a methyl group, and R1 represents alkyl group having a carbon number of 1 to 5, and l represents an integer of 0 to 3.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: April 29, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kouji Yonemura, Taku Nakao
  • Patent number: 7329478
    Abstract: To provide a chemical amplification type positive photoresist composition, which has high sensitivity, high heat resistance and high resolution (high contrast) and is capable of suppressing an undulation phenomenon, and a method for formation of a resist pattern, a chemical amplification type positive photoresist composition comprising (A) an alkali soluble resin comprising a hydroxystyrene constituent unit (a1) and a styrene constituent unit (a2), (B) a crosslinking agent, (C) a photo acid generator, and an organic solvent is prepared and a resist pattern is formed by using the same.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: February 12, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yusuke Nakagawa, Shinichi Hidesaka, Kenji Maruyama, Satoshi Shimatani, Masahiro Masujima, Kazuyuki Nitta
  • Patent number: 7323284
    Abstract: A negative type radiation sensitive resin composition comprising: (A) an alkali-soluble resin containing the polymerized unit of a polymerizable unsaturated compound having a phenolic hydroxyl group and having a weight average molecular weight of 4,100 to 20,000 and a weight average molecular weight/number average molecular weight ratio of more than 1.25 to not more than 2.00; (B) a radiation sensitive acid generating agent; and (C) an acid crosslinking agent. This composition can be used with an alkali developer having a normal concentration, can form a high-resolution rectangular line-and-space resist pattern, and provides a chemically amplified negative type resist which is free from a resist pattern defect (bridging or chip line) after development and has excellent sensitivity, developability and dimensional fidelity.
    Type: Grant
    Filed: June 17, 2002
    Date of Patent: January 29, 2008
    Assignee: JSR Corporation
    Inventors: Toshiyuki Kai, Daigo Ichinohe
  • Patent number: 7282316
    Abstract: Provided are sulfonyldiazomethane compounds and photoacid generators suited for resist materials which generate less foreign matters after application, development and peeling, and in particular, are excellent in the pattern profile after the development; and resist materials and patterning process using them. Provided are sulfonyldiazomethane compounds represented by formula (1): Also provides are photoacid generators containing the sulfonyldiazomethane compounds, and a chemical amplification resist material comprising (A) a resin which changes its solubility in an alkali developer by action of an acid, and (B) a sulfonyldiazomethane compound of formula (1) capable of generating an acid by exposure to radiation. Provided is a patterning process comprising steps of applying the above-described resist material onto a substrate to form a coating, heating the coating, exposing the coating, and developing the exposed coating in a developer after an optional heat treatment.
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: October 16, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Eiji Fukuda, Shigeo Tanaka
  • Patent number: 7226717
    Abstract: The present invention relates to a resin composition comprising: an alkali-soluble resin (A); an infrared absorbing agent (B); and a thiol compound (C), wherein a solubility thereof in an alkaline aqueous solution is changed by exposure with a infrared laser ray, and a positive or negative-type image recording layer containing the resin composition.
    Type: Grant
    Filed: July 14, 2003
    Date of Patent: June 5, 2007
    Assignee: Fujifilm Corporation
    Inventors: Ippei Nakamura, Akihiro Endo
  • Patent number: 7214465
    Abstract: A positive photosensitive composition comprising (A1) a compound that generates an aromatic sulfonic acid substituted with at least one fluorine atom and/or a group having at least one fluorine atom upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a compound that has at least three hydroxy or substituted hydroxy groups and at least one cyclic structure or (A2) an onium salt of an alkanesulfonic acid in which the ?-position of the sulfonic acid is not substituted with a fluorine atom and/or an onium salt of a carboxylic acid.
    Type: Grant
    Filed: January 9, 2003
    Date of Patent: May 8, 2007
    Assignee: Fujifilm Corporation
    Inventors: Hajime Nakao, Yasumasa Kawabe, Toru Fujimori, Kunihiko Kodama
  • Patent number: 7150956
    Abstract: The present invention provides a resist composition comprising (A) polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with an acid-dissociable dissolution inhibiting group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the acid-dissociable dissolution inhibiting group is eliminated by an action of an acid, and (B) a component capable of generating an acid by irradiation with radiation, wherein a retention rate of the acid-dissociable dissolution inhibiting group of the component (A) after a dissociation test using hydrochloric acid is 40% or less, and also provides a chemical amplification type positive resist composition which contains polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with a lower alkoxy-alkyl group having a straight-chain or branched alkoxy group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the lower alkoxy-alkyl group
    Type: Grant
    Filed: January 3, 2005
    Date of Patent: December 19, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazuyuki Nitta, Takeyoshi Mimura, Satoshi Shimatani, Waki Okubo, Tatsuya Matsumi
  • Patent number: 7141351
    Abstract: Resist compositions comprising basic compounds having an imidazole skeleton and a polar functional group have an excellent resolution and an excellent focus margin and are useful in microfabrication using electron beams or deep-UV light.
    Type: Grant
    Filed: May 20, 2004
    Date of Patent: November 28, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa
  • Patent number: 7118845
    Abstract: A process for fabricating of an article by exposing a photoreactive composition to light under multiphoton absorption conditions. The light passes through an optical system having a final optical element having a numeric aperture in a range of from 0.65 to 1.25, inclusive.
    Type: Grant
    Filed: June 5, 2003
    Date of Patent: October 10, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Robert J. DeVoe, Harvey W. Kalweit, Catherine A. Leatherdale, Todd R. Williams
  • Patent number: 7109311
    Abstract: A chemical amplification type resist composition comprising a specific benzenesulfonyldiazomethane containing a long-chain alkoxyl group at the 2-position on benzene ring has many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development and is thus suited for microfabrication.
    Type: Grant
    Filed: February 12, 2004
    Date of Patent: September 19, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Yoshitaka Yanagi, Kazunori Maeda
  • Patent number: 7101651
    Abstract: A chemical amplification type resist composition comprising a specific sulfonyldiazomethane containing long-chain alkoxyl groups has many advantages including improved resolution, improved focus latitude, minimized line width variation or shape degradation even on long-term PED, minimized debris left after coating, development and peeling, and improved pattern profile after development and is thus suited for microfabrication.
    Type: Grant
    Filed: February 12, 2004
    Date of Patent: September 5, 2006
    Assignee: Shin-Etsu Chemical Co.,Ltd.
    Inventors: Youichi Ohsawa, Katsuhiro Kobayashi, Yoshitaka Yanagi, Kazunori Maeda
  • Patent number: 7056640
    Abstract: Sulfonyldiazomethane compounds containing a long-chain alkyl- or alkoxy-naphthyl group are novel and useful as photoacid generators. Chemical amplification type resist compositions comprising the same are suited for microfabrication because of many advantages including improved resolution, improved focus latitude, and minimized line width variation or shape degradation even on long-term PED.
    Type: Grant
    Filed: August 8, 2003
    Date of Patent: June 6, 2006
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Satoshi Watanabe, Kazunori Maeda
  • 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: 7015256
    Abstract: A photosensitive composition for forming a dielectric of the present invention comprising inorganic particles, an alkali developable resin and additives, wherein the additives comprise a compound having a quinonediazido group (C1), a compound containing at least two alkyletherified amino groups in the molecule (C2) and a thermal acid generator (C3), or wherein the inorganic particles comprise inorganic superfine particles (A-I) having a mean particle diameter of less than 0.05 ?m and inorganic fine particles (A-II) having a mean particle diameter of not less than 0.05 ?m. The composition can be calcined at low temperatures to form a dielectric layer with high dimensional precision, said layer having a high dielectric constant and a low dielectric loss. Also provided are a dielectric and an electronic part prepared from the composition.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: March 21, 2006
    Assignee: JSR Corporation
    Inventors: Nobuyuki Ito, Hideaki Masuko, Satomi Hasegawa, Atsushi Ito, Katsumi Inomata
  • Patent number: 7005229
    Abstract: A method of multiphoton photosensitizing comprises (a) providing a multiphoton-activatable, photoreactive composition comprising (1) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction, and (2) a photoinitiator system comprising photochemically-effective amounts of (i) at least one type of semiconductor nanoparticle that has at least one electronic excited state that is accessible by absorption of two or more photons, and (ii) a composition that is capable of interacting with the excited state of the semiconductor nanoparticle to form at least one reaction-initiating species; and (b) irradiating the multiphoton-activatable, photoreactive composition with light sufficient to cause absorption of at least two photons, thereby inducing at least one acid- or radical-initiated chemical reaction where the composition is exposed to the light.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: February 28, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Manoj Nirmal, Catherine A. Leatherdale, David S. Arney
  • Patent number: 6927274
    Abstract: Polyimide precursors contained in resin compositions of the present invention have a polymer structure unit represented by formula (1) below: wherein chemical structure A2 includes an alicyclic compound but not an aromatic compound such as a benzene ring so that they provide excellent light transmission over a wide wavelength range. The polyimide precursors are imidized at 7.5% or more and 36% or less so that they are less soluble in developing solutions and therefore are not dissolved in the developing solutions at unexposed parts. Thus, the resin compositions of the present invention can be used to form a resin film having a precise pattern by exposure and development.
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: August 9, 2005
    Assignee: Sony Chemicals Corp.
    Inventors: Mamiko Nomura, Masatoshi Hasegawa, Junichi Ishii, Tadashi Akamatsu
  • Patent number: 6924323
    Abstract: A compound shown by the general formula [1] (wherein R1, R2 and R3 are each independently an aromatic hydrocarbon residual group, Yn? is an anion derived from a carboxylic acid having 3 or more carbon atoms with substituted fluorine atoms, and n is 1 or 2, provided that R1, R2 and R3 each is not a phenyl group having substituents at an ortho and/or a meta position), and a composition consisting of the compound and a diazodisulfone compound are disclosed. Use of the compound or the compound as an acid generator for resists produces the effects of improving the profiles of ultra-fine patterns or diminishing sidewall irregularities in ultra-fine patterns. The compound is also useful as a cationic photopolymerization initiator.
    Type: Grant
    Filed: June 27, 2001
    Date of Patent: August 2, 2005
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Masami Ishihara, Motoshige Sumino, Kazuhito Fukasawa, Naoki Katano, Shigeaki Imazeki
  • Patent number: 6921621
    Abstract: The present invention provides a resist composition comprising (A) polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with an acid-dissociable dissolution inhibiting group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the acid-dissociable dissolution inhibiting group is eliminated by an action of an acid, and (B) a component capable of generating an acid by irradiation with radiation, wherein a retention rate of the acid-dissociable dissolution inhibiting group of the component (A) after a dissociation test using hydrochloric acid is 40% or less, and also provides a chemical amplification type positive resist composition which contains polyhydroxystyrene in which at least a portion of hydrogen atoms of hydroxyl groups are substituted with a lower alkoxy-alkyl group having a straight-chain or branched alkoxy group, and the solubility in an alkali solution of the polyhydroxystyrene increasing when the lower alkoxy-alkyl group
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: July 26, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazuyuki Nitta, Takeyoshi Mimura, Satoshi Shimatani, Waki Okubo, Tatsuya Matsumi
  • Patent number: 6908727
    Abstract: This invention describes a heat sensitive composition comprising: (A-I) a compound which is represented by the following general formula (I) and generates a radical when heated, and (B-I) a compound having physical and chemical properties that are changed irreversibly by a radical, R—SO2?M+??General formula (I) wherein R represents an alkyl group or aryl group, and M+ represents a counter cation selected from sulfonium, iodonium, diazonium, ammonium and azinium; and a negative planographic printing plate precursor which can be recorded by heat mode using this composition. This invention also describes a planographic printing plate precursor comprising a substrate having disposed thereon a photosensitive layer containing (C-II) a light-heat converting agent, (B-II) a compound having a polymerizable unsaturated group, and (A-II) an onium salt having at least two cation parts in one molecule.
    Type: Grant
    Filed: March 11, 2004
    Date of Patent: June 21, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuto Shimada, Tadahiro Sorori, Morio Yagihara