Spectral Sensitizer Containing Patents (Class 430/926)
  • Patent number: 8871430
    Abstract: The present invention relates to a photoactive compound having a novel structure and a photosensitive resin composition including the same, and the photoactive compound according to the present invention has excellent sensitivity due to efficient absorption to a UV light source by including a nitro group and a phosphonate structure, and has excellent retention rate, mechanical strength, heat resistance, chemical resistance and developing resistance by improving solubility of the photosensitive resin composition by excellent compatibility of the phosphonate structure and a binder resin. Therefore, the photosensitive resin composition according to the present invention is useful to cure a column spacer, an overcoat, a passivation material and the like of a liquid crystal display device, and is useful in view of a high temperature process property.
    Type: Grant
    Filed: May 14, 2012
    Date of Patent: October 28, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Changho Cho, Won Jin Chung, Raisa Kharbash, Sunghyun Kim, Dongchang Choi, Sang Chul Lee, Han Soo Kim, Yoon Hee Heo, Sunhwa Kim
  • Patent number: 8592131
    Abstract: An ortho-nitrobenzyl ester compound including a compound represented by Chemical Formula 1, and a positive photosensitive resin composition including the same are provided.
    Type: Grant
    Filed: September 22, 2011
    Date of Patent: November 26, 2013
    Assignee: Cheil Industries Inc.
    Inventors: Min-Kook Chung, Ji-Young Jeong, Hyun-Yong Cho, Yong-Sik Yoo, Jeong-Woo Lee, Jong-Hwa Lee, Hwan-Sung Cheon, Soo-Young Kim, Young-Ho Kim, Jae-Hyun Kim, Su-Min Park
  • Patent number: 8586279
    Abstract: The present invention provides dual wavelength imaging compositions, processes for forming dual wavelength imaging compositions, methods for forming images using dual wavelength imaging compositions and substrate (e.g., paper web) treated (e.g., coated) on one or both sides with dual wavelength imaging compositions. Also provided is a dual wavelength imaging particulate comprising a matrix of polymer material and containing: one or more image-forming agents; a photo-oxidizing agent which is activated at a first wavelength of light to cause the one or more image-forming agents to form one or more images; and a reducing agent which is activated at a second wavelength of light to cause termination of the formation of the one or more images.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: November 19, 2013
    Assignee: International Paper Company
    Inventors: Richard C. Williams, Richard D. Faber, Oleg Grinevich, John Malpert, Alexandre Mejiritski, Douglas C. Neckers
  • Patent number: 8586280
    Abstract: The present invention provides dual energy imaging compositions, processes for forming dual energy imaging compositions, methods for forming images using dual energy imaging compositions and substrate (e.g., paper web) treated (e.g., coated) on one or both sides with a dual energy imaging composition. Also provided is a particulate comprising a matrix of polymer material and containing one or more image-forming agents and a photo-oxidizing agent useful in making dual energy imaging compositions.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: November 19, 2013
    Assignee: International Paper Company
    Inventors: Richard C. Williams, Richard D. Faber, Oleg Grinevich, John Malpert, Alexandre Mejiritski, Douglas C. Neckers
  • Patent number: 8563222
    Abstract: A lithographic printing plate precursor comprising an image-recording layer, said image-recording layer being photopolymerizable upon exposure to light having a wavelength of from 300 to 500 nm and containing a mixture of sensitizers.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: October 22, 2013
    Assignee: Agfa Graphics NV
    Inventors: Jan Venneman, Peter Hendrikx, Paul Callant, Alexander Williamson
  • Patent number: 8445176
    Abstract: A lithographic printing plate precursor comprising an image-recording layer, said image-recording layer being photopolymerizable upon exposure to light having a wavelength of from 300 to 500 nm and containing a mixture of sensitizers.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: May 21, 2013
    Assignee: Agfa Graphics NV
    Inventors: Jan Venneman, Peter Hendrikx, Paul Callant, Alexander Williamson
  • Patent number: 8383316
    Abstract: New routes involving multi-step reversible photo-chemical reactions using two-step techniques to provide non-linear resist for lithography are described in this disclosure. They may provide exposure quadratically dependant on the intensity of the light. Several specific examples, including but not limited to using nanocrystals, are also described. Combined with double patterning, these approaches may create sub-diffraction limit feature density.
    Type: Grant
    Filed: July 6, 2007
    Date of Patent: February 26, 2013
    Assignee: Pixelligent Technologies, LLC
    Inventors: Gregory D. Cooper, Zhiyun Chen, Z Serpil Gonen Williams, Larry F. Thompson
  • Patent number: 8323866
    Abstract: Methods and compositions for enhancing the sensitivity of an inorganic resist composition are disclosed. In one aspect, compositions for use with a matrix material (e.g., a lithographically sensitive polymeric material such as a hydrogen-bearing siloxane material) can be formulated with a sensitizer, where the sensitizer can be present in a relatively small amount. The sensitizer can include a radical generator, and can act to enhance the efficiency of radical generation and/or resist crosslinking when the resist is impinged by a selected lithographic radiation. The methods of the present invention can be especially useful in performing short wavelength (e.g., less than 200 nm) lithography, or for processes such as e-beam lithography, which traditionally suffer from low throughput. Methods of utilizing one or more of these aspects are also disclosed.
    Type: Grant
    Filed: July 6, 2009
    Date of Patent: December 4, 2012
    Assignee: Massachusetts Institute of Technology
    Inventors: Theodore H. Fedynyshyn, Russell B. Goodman
  • Patent number: 8227180
    Abstract: An anti-reflective coating material, a microelectronic structure that includes an anti-reflective coating layer formed from the anti-reflective coating material and a related method for exposing a resist layer located over a substrate while using the anti-reflective coating layer provide for attenuation of secondary reflected vertical alignment beam radiation when aligning the substrate including the resist layer located thereover. Such enhanced vertical alignment provides for improved dimensional integrity of a patterned resist layer formed from the resist layer, as well as additional target layers that may be fabricated while using the resist layer as a mask.
    Type: Grant
    Filed: June 13, 2011
    Date of Patent: July 24, 2012
    Assignee: International Business Machines Corporation
    Inventors: Timothy Allan Brunner, Sean David Burns, Kuang-Jung Chen, Wu-Song Huang, Kafai Lai, Wai-Kin Li, Bernhard R. Liegl
  • Patent number: 8168369
    Abstract: The present invention relates to a photoactive compound of a novel structure represented by Chemical Formula 1 below In Chemical Formula 1, R1 and R2, R3, and A are as defined in the specification, and a photosensitive resin composition comprising the same. The photoactive compound of the present invention comprises a nitro group and a phosphonate structure and thus exhibits excellent sensitivity through efficient absorption for UV light, excellent compatibility between the photoactive compound and the alkali-soluble binder resin, and an improved solubility of the photosensitive resin composition. Furthermore, the photosensitive resin composition of the present invention has excellent residual film thickness and mechanical strength characteristics and heat-resistant, chemical-resistant, and development-resistant properties.
    Type: Grant
    Filed: February 12, 2010
    Date of Patent: May 1, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Chang Ho Cho, Sung Hyun Kim, Raisa Kharbash, Keon Woo Lee, Dong Kung Oh, Won Jin Chung, Sang Kyu Kwak, Chang Soon Lee
  • Patent number: 8163462
    Abstract: The present invention relates to a photosensitive composition, which is capable of being irradiated with high energy beam having a wave length of 1 to 300 nm band. The photosensitive composition includes a binder resin; and a photoelectron absorbent, capable of being excited with photoelectron emitted from the binder resin that absorbs the high energy beam, when the binder resin is irradiated with the high energy beam.
    Type: Grant
    Filed: June 17, 2009
    Date of Patent: April 24, 2012
    Assignee: Renesas Electronics Corporation
    Inventors: Minoru Toriumi, Toshiro Itani
  • Patent number: 8158338
    Abstract: Methods and compositions for enhancing the sensitivity of a resist composition are disclosed. In one aspect, compositions for use with a matrix material (e.g., a lithographically sensitive polymeric material) can be formulated with an acid generator and a sensitizer, where the sensitizer can be present in a relatively small amount. The sensitizer can include a compound with one or more silicon-silicon bonds, and can act to enhance the efficiency of acid generation when the resist is impinged by a selected lithographic radiation. The methods of the present invention can be especially useful in performing short wavelength (e.g., less than 200 nm) lithography, or for processes such as e-beam lithography, which traditionally suffer from low throughput.
    Type: Grant
    Filed: July 8, 2008
    Date of Patent: April 17, 2012
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 8142983
    Abstract: A lithographic printing plate precursor is provided that, using laser exposure, exhibits an excellent capacity for plate inspection, an excellent on-press development performance or gum development performance, and an excellent scumming behavior, while maintaining a satisfactory printing durability. There is also provided a method of lithographic printing that uses this lithographic printing plate precursor. The lithographic printing plate precursor comprises an image recording layer having (A) a nonionic polymerization initiator that contains at least two cyclic imide structures, and (B) a compound that has at least one addition-polymerizable ethylenically unsaturated bond.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: March 27, 2012
    Assignee: Fujifilm Corporation
    Inventor: Shota Suzuki
  • Patent number: 8105759
    Abstract: A photosensitive resin composition comprising (A) a binder polymer, (B) a photopolymerizing compound with a polymerizable ethylenic unsaturated bond, (C) a photoradical polymerization initiator containing a 2,4,5-triarylimidazole dimer or its derivative, and (D) a compound represented by the following general formula (1) (wherein R1 and R2 each independently represent C1-20 alkyl, etc., and R3, R4, R5, R6, R7, R8, R9 and R10 each independently represent hydrogen, etc.).
    Type: Grant
    Filed: January 3, 2006
    Date of Patent: January 31, 2012
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Masahiro Miyasaka, Takashi Kumaki
  • Patent number: 8048613
    Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.
    Type: Grant
    Filed: October 13, 2008
    Date of Patent: November 1, 2011
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
  • Patent number: 7977030
    Abstract: A photosensitive resin composition, a photosensitive resin laminate, and a method for forming a pattern capable of realizing high hardness while using an epoxy group-containing acrylic resin are provided. In a photosensitive resin composition including (A) an epoxy group-containing acrylic resin, (B) a photopolymerization initiator, and (C) a sensitizer, an onium salt having a specific structure is used as the component (B), and at least one kind selected from 1,5-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene is used as the component (C).
    Type: Grant
    Filed: June 10, 2008
    Date of Patent: July 12, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Senzaki, Koichi Misumi, Koji Saito
  • Patent number: 7964654
    Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.
    Type: Grant
    Filed: September 14, 2010
    Date of Patent: June 21, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Patent number: 7927781
    Abstract: The present invention relates to a photosensitive resin composition including a) an alkali-soluble acrylate resin, b) a cross-linking monomer having at least two ethylenic double bonds, and c) a phosphinoxide based photopolymerization initiator and an acridon based photopolymerization initiator; a preparation method thereof; and a dry film resist comprising the same.
    Type: Grant
    Filed: December 4, 2008
    Date of Patent: April 19, 2011
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: In-Ho Yoon, Bong-Gi Kim, Chang-Seok Rho, Sang-Ki Kang, Kyung-Rock Byun, Chan-Seok Park
  • Patent number: 7901871
    Abstract: A composition containing a photoacid generator monomer and surfactant, and a method for synthesizing a compound on a substrate using the composition are provided. The method includes bonding a layer of first molecules having an acid labile protecting group to a solid substrate; coating a layer of the photoacid generator monomer composition according to the present invention on the layer of first molecules; exposing the composition layer to light and then heat-treating to remove the acid labile protecting group from the first molecules corresponding to the exposed portion; washing and removing the composition layer from the exposed and unexposed portions; and bonding second molecules to the exposed first molecules.
    Type: Grant
    Filed: January 9, 2008
    Date of Patent: March 8, 2011
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
  • Patent number: 7863344
    Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.
    Type: Grant
    Filed: November 3, 2008
    Date of Patent: January 4, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Patent number: 7811742
    Abstract: A lithographic printing plate precursor includes: a support; and a photosensitive layer containing a binder polymer containing a positively charged nitrogen atom in at least one of a main chain and a side chain of the binder polymer, a compound containing an ethylenically unsubstituted bond; and a radical polymerization initiator.
    Type: Grant
    Filed: February 22, 2008
    Date of Patent: October 12, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Yoshinori Taguchi, Keiichi Adachi, Shigekatsu Fujii
  • Patent number: 7781143
    Abstract: Negative-working imageable elements that can be imaged using infrared radiation comprise an imageable layer and a protective overcoat on a hydrophilic substrate. The imageable layer includes an IR-sensitive cyanine dye. The protective overcoat predominantly comprises one or more poly(vinyl alcohol) resins, each of which has a hydrolysis level of 85% or less. The use of this particular overcoat composition used in combination with the IR-sensitive cyanine dye provides improved tolerance to fogging by white light while maintaining desired imaging speed.
    Type: Grant
    Filed: May 31, 2007
    Date of Patent: August 24, 2010
    Assignee: Eastman Kodak Company
    Inventors: Jianfei Yu, Kevin B. Ray
  • Patent number: 7776507
    Abstract: A photosensitive paste is provided with which a member for a display panel having superior visibility can be manufactured with simple steps, and with the photosensitive paste including a soft magnetic powder, a glass powder, and a photosensitive organic component, in which the mass ratio of the soft magnetic powder (A) to the glass powder (B) is in the range of 20/80 to 70/30.
    Type: Grant
    Filed: July 14, 2005
    Date of Patent: August 17, 2010
    Assignee: Toray Industries, Inc.
    Inventors: Kazutaka Kusano, Yuko Fujiwara, Yuichiro Iguchi
  • Patent number: 7771916
    Abstract: The present invention provides a polymerizable composition comprising (A) a compound represented by the following formula (I), (B) an infrared absorbent, and (C) a compound having at least one addition-polymerizable ethylenically unsaturated bond, and a negative planographic printing plate precursor having a recording layer containing the polymerizable composition. In the formula (I), R1, R2, R3, R4, R5, and R6 each independently represent a hydrogen atom or a monovalent organic group; and X? represents an anion.
    Type: Grant
    Filed: July 29, 2005
    Date of Patent: August 10, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Yoshinori Taguchi, Kazuhiro Fujimaki
  • Patent number: 7635552
    Abstract: A photoresist composition, e.g., a positive acting resist, for use in the formation of circuit patterns and the like on printed circuit boards and the like circuitized substrates, the photoresist composition including a quantity of silver therein in a sufficient amount to substantially prevent bacteria formation within said composition. A method of making the composition is also provided.
    Type: Grant
    Filed: July 25, 2006
    Date of Patent: December 22, 2009
    Assignee: Endicott Interconnect Technologies, Inc.
    Inventors: Ross W. Keesler, John J. Konrad, Roy H. Magnuson, Robert A. Sinicki
  • Patent number: 7632630
    Abstract: The present invention provides new photoresist compositions that comprise a resin binder, a photoactive component, particularly an acid generator, and a dye material that contains one or more chromophores that can reduce undesired reflections of exposure radiation. Preferred dye compounds are polymeric materials that include one or more chromophores such as anthracene and other polycyclic moieties that effectively absorb deep UV exposure radiation.
    Type: Grant
    Filed: May 3, 2006
    Date of Patent: December 15, 2009
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James Michael Mori, James W. Thackeray, Roger F. Sinta, Rosemary Bell, Robin L. Miller-Fahey, Timothy G. Adams, Thomas M. Zydowsky, Edward K. Pavelchek, Manual doCanto
  • Patent number: 7615323
    Abstract: Lithographic printing plate precursor comprising (a) a lithographic substrate with a hydrophilic surface and (b) a radiation-sensitive coating on the hydrophilic surface comprising (i) one or more types of monomers and/or oligomers and/or polymers, each comprising at least one ethylenically unsaturated group accessible to a free radical polymerization, (ii) at least one sensitizer, and at least one coinitiator capable of forming free radicals together with the sensitizer (ii); characterized in that the at least one sensitizer is an oligomeric or polymeric compound comprising the following structural unit (Formula (I)), wherein ?1 is an aromatic or heteroaromatic unit or a combination of the two so that a conjugated n-system is present between the two groups Z in structure (I), each Z independently represents a heteroatom, each R1 and R2 is independently selected from a halogen atom, an alkyl, aryl, alkylaryl or aralkyl group, a group —NR3R4 and a group —OR5, each R3, R4 and R5 is independently selected from a
    Type: Grant
    Filed: November 11, 2005
    Date of Patent: November 10, 2009
    Assignee: Kodak Graphic Communications, GmbH
    Inventors: Bernd Strehmel, Harald Baumann, Udo Dwars, Detlef Pietsch, Axel Draber, Michael Mursal
  • Patent number: 7582407
    Abstract: Single- and multi-layer positive-working imageable elements include an ink receptive outer layer includes a primary polymeric binder that is a poly(vinyl phenol) or a phenolic polymer having certain acidic groups. The use of this type of polymeric binder makes the imaged elements developable in low pH (11 or less) alkaline developers.
    Type: Grant
    Filed: July 9, 2007
    Date of Patent: September 1, 2009
    Assignee: Eastman Kodak Company
    Inventors: Celin Savariar-Hauck, Alan S. Monk, Gerhard Hauck
  • Patent number: 7579134
    Abstract: The present invention is directed to coverlay compositions derived from two-layer polyamic acid-based composites having a cover layer and adjacent thereto an adhesive layer wherein the cover layer comprises polyamic acid and other additives allowing the composition to be photosensitive and aqueous base developable, and where the adhesive layer can form a polyimide having a glass transition temperature between 170 and 250° C. The two-layer coverlay compositions of the present invention are used to encapsulate metal circuit traces formed on a flexible printed circuit base substrate. These two-layer compositions are particularity useful due to having an overall in-plane CTE between 10 and 40 ppm/° C. a range that is useful in avoiding unwanted curling of a flexible printed circuit when used as a polyimide-based coverlay material.
    Type: Grant
    Filed: March 15, 2005
    Date of Patent: August 25, 2009
    Assignee: E. I. Dupont de Nemours and Company
    Inventors: Thomas Eugene Dueber, Brian C. Auman, Kuppusamy Kanakarajan
  • Patent number: 7524611
    Abstract: Image formation via photoinduced fluorescence changes in a polymeric medium with two-photon fluorescence readout of a multi-layer structure. Fluorophore-containing polymers, possessing one or more basic functional groups, underwent protonation in the presence of a photoinduced acid generator upon exposure to a broad-band UV light source or fast-pulsed red to near-IR laser irradiation. Solution studies demonstrated formation of monoprotonated and diprotonated species upon irradiation, each resulting in distinctly different absorption and fluorescence properties. The fluorescence of the original, neutral, fluorophore was reduced upon monoprotonation, leading to a concomitant increase in fluorescence at longer wavelengths due to the monoprotonated form, the basis for multichannel data readout.
    Type: Grant
    Filed: September 26, 2007
    Date of Patent: April 28, 2009
    Assignee: University of Central Florida Research Foundation, Inc.
    Inventor: Kevin D. Belfield
  • Patent number: 7476489
    Abstract: The invention relates to low-temperature curable photosensitive compositions containing a polyamic acid, which compositions are developable in aqueous alkaline solutions and are curable, at a temperature of at least 160° C. and up to 200° C., to low modulus polyimides suitable for use in electronic circuitry applications, and which are particularly suitable for use in flexible circuit applications where low curl, low temperature curing, and good adhesion is a significant advantage.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: January 13, 2009
    Assignee: E.I. DuPont de Nemours
    Inventors: Thomas E. Dueber, Michael W. J. West, Kuppusamy Kanakarajan, Brian C. Auman
  • Patent number: 7407735
    Abstract: Disclosed are a light sensitive planographic printing plate precursor and its processing method, the precursor comprising a hydrophilic support and provided thereon, a photopolymerizable light sensitive layer containing a compound represented by the following formula (1) or (2) and a compound represented by the following formula (3) or (4):
    Type: Grant
    Filed: January 18, 2006
    Date of Patent: August 5, 2008
    Assignee: Konica Corporation
    Inventor: Kazuhiko Hirabayashi
  • Patent number: 7368224
    Abstract: The invention provides a photopolymerizable composition having a high photosensitivity, which comprises a metal complex of a squarylium compound, a radical generator, and a compound having at least one ethylenically unsaturated double bond. The photopolymerizable composition of the present invention is advantageously used for a visible laser recording material such as a PS (Presensitized Plate) for laser direct plate-making, a dry film resist, a digital proof, a hologram, or the like, a panchromatic sensitive material (e.g., a sensitive material for a color hologram and a sensitive material used for full-color display and containing a photopolymerizable composition in a microcapsule), paints, adhesives, and so on.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: May 6, 2008
    Assignee: Kyowa Hakko Chemical Co., Ltd.
    Inventors: Tsuguo Yamaoka, Ikuo Shimizu, Hiroshi Toyoda, Motoharu Kinugasa, Masanori Ikuta, Kyoko Katagi
  • Patent number: 7354692
    Abstract: A class of lithographic photoresist combinations is disclosed which is suitable for use with visible light and does not require a post-exposure bake step. The disclosed photoresists are preferably chemical amplification photoresists and contain a photosensitizer having the structure of formula (I): where Ar1 and Ar2 are independently selected from monocyclic aryl and monocyclic heteroaryl, R1 and R2 may be the same or different, and have the structure —X—R3 where X is O or S and R3 is C1-C6 hydrocarbyl or heteroatom-containing C1-C6 hydrocarbyl, and R4 and R5 are independently selected from the group consisting of hydrogen and —X—R3, or, if ortho to each other, may be taken together to form a five- or six-membered aromatic ring, with the proviso that any heteroatom contained within Ar1, Ar2, or R3 is O or S. The use of the disclosed photoresists, particularly for the manufacture of holographic diffraction gratings, is also disclosed.
    Type: Grant
    Filed: May 9, 2005
    Date of Patent: April 8, 2008
    Assignee: International Business Machines Corporation
    Inventors: Gregory Breyta, Daniel Joseph Dawson, Carl E. Larson, Gregory Michael Wallraff
  • Patent number: 7341828
    Abstract: A photopolymerization initiator composition containing a thiol compound having a mercapto group-containing group that has at least one substituent on the carbon atoms on carbon atom(s) at the ?- and/or ?-position with respect to the mercapto group and a photopolymerization initiator; a photosensitive composition containing the composition; and a novel thiol compound for use in these compositions. The photosensitive composition containing the photopolymerizazion initiator composition of the present invention has high sensitivity and excellent storage stability and enables reduction in cost due by increasing productivity.
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: March 11, 2008
    Assignee: Showa Denko K.K.
    Inventors: Tsuyoshi Katoh, Hirotoshi Kamata, Mina Onishi
  • Patent number: 7335457
    Abstract: A positive-tone radiation-sensitive resin composition containing an anthracene-based carboxylic acid component with low sublimation properties and excellent compatibility with other components is provided. The composition exhibits optimum controllability of radiation transmittance as a chemically amplified positive-tone resist effectively responding to active radiation, particularly to deep ultraviolet rays, effectively controlling line width variation in resist patterns due to fluctuation in the resist film thickness on a highly refractive substrate, and exhibiting excellent focal depth allowance. The composition comprises (A) an anthracene derivative of the following formula (1), (B) a photoacid generator comprising a sulfonimide compound, and, (C) a resin containing an acid-dissociable group, wherein R1 is a hydrogen atom or a monovalent organic group, R2 is a monovalent organic group, e is an integer of 0-3, and f is an integer of 0-8.
    Type: Grant
    Filed: September 27, 2005
    Date of Patent: February 26, 2008
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Tomoki Nagai, Yuuji Yada, Kentarou Gotou
  • Patent number: 7326517
    Abstract: A photosensitive composition containing: (A) a sensitizing dye; (B) a photopolymerization initiator; (c) a polymerizable compound having an ethylenically unsaturated bond; and (D) a polymer binder, wherein the photopolymerization initiator exhibits a reaction rate constant with a semiquinone radical anion in the range of 2.0×102 to 1.0×108 (mol?1·l·s?1).
    Type: Grant
    Filed: April 4, 2005
    Date of Patent: February 5, 2008
    Assignee: Konica Minolta Medical & Graphic, Inc.
    Inventor: Toshiyuki Matsumura
  • Patent number: 7270932
    Abstract: Imaging compositions and methods of using the compositions are disclosed. The imaging compositions are sensitive to low levels of energy such that upon application of the low levels of energy the compositions change color or shade. The compositions may be used in methods of marking.
    Type: Grant
    Filed: February 6, 2004
    Date of Patent: September 18, 2007
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Robert K. Barr, James T. Fahey, Corey O'Connor, James G. Shelnut, John J. Piskorski
  • Patent number: 7267925
    Abstract: A photosensitive composition containing: a sensitizing dye represented by the formula (1) as defined herein; an initiator compound capable of generating a radical, an acid, or a base; and a compound whose physical or chemical characteristic irreversibly changes by at least one of a radical, an acid, and a base.
    Type: Grant
    Filed: March 31, 2004
    Date of Patent: September 11, 2007
    Assignee: Fujifilm Corporation
    Inventor: Akinori Shibuya
  • Patent number: 7258962
    Abstract: A positive-tone radiation-sensitive resin composition comprising: (A) a carbazole derivative shown by the following formula (1), (B) a photoacid generator containing a sulfonimide compound and an iodonium salt compound as essential components, and (C) an acid-dissociable group-containing resin which is insoluble or scarcely soluble in alkali, but becomes soluble in alkali when the acid-dissociable group dissociates is disclosed. wherein R1 and R2 are individually halogen atom, methyl, cyano, or nitro group, X is a C1-20 organic group, and h and i are 0-4. The resin composition is useful as a chemically amplified positive-tone resist excelling in focal depth allowance, sensitivity, resolution, pattern profile, and PED stability.
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: August 21, 2007
    Assignee: JSR Corporation
    Inventors: Tomoki Nagai, Takayuki Tsuji
  • 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: 7252925
    Abstract: Resist compositions comprising nitrogen-containing organic compounds having a benzimidazole structure and a specific ether chain moiety have an excellent resolution, form precisely configured patterns with minimized roughness of sidewalls and are useful in microfabrication using electron beams or deep-UV light.
    Type: Grant
    Filed: October 28, 2004
    Date of Patent: August 7, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Katsuya Takemura, Akihiro Seki
  • Patent number: 7241557
    Abstract: A composition that is photopolymerizable upon absorption of light in the wavelength range from 300 to 450 nm, the composition comprising a binder, a polymerizable compound, a sensitizer and a photoinitiator, wherein the sensitizer is a fluorene compound that is conjugated via a double or triple bond with an aromatic or heteroaromatic group, and is characterized by a high sensitivity.
    Type: Grant
    Filed: July 29, 2005
    Date of Patent: July 10, 2007
    Assignee: Agfa Graphics NV
    Inventors: Alexander Williamson, Paul Callant
  • Patent number: 7223519
    Abstract: Imaging compositions and methods of using the compositions are disclosed. The imaging compositions are sensitive to low levels of energy such that upon application of the low levels of energy the compositions change color or shade. The compositions may be applied to a work piece to mark it and removed from the work piece by peeling.
    Type: Grant
    Filed: July 13, 2005
    Date of Patent: May 29, 2007
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Robert K. Barr, Corey O'Connor
  • Patent number: 7175967
    Abstract: Positive-working imageable elements are prepared by providing a first layer and second layers onto a substrate. Both layers include the same or different radiation absorbing compounds dispersed within different polymeric binders. After both layers are dried, they are heat treated at from about 40 to about 90° C. for at least 4 hours under conditions that inhibit the removal of moisture from the dried first and second layers. This method of preparation provides elements with improved imaging speed and good shelf life.
    Type: Grant
    Filed: March 2, 2006
    Date of Patent: February 13, 2007
    Assignee: Eastman Kodak Company
    Inventors: James L. Mulligan, Eric Clark, Kevin B. Ray
  • Patent number: 7147983
    Abstract: The present invention provides new photoresist compositions that comprise a resin binder, a photoactive component, particularly an acid generator, and a dye material that contains one or more chromophores that can reduce undesired reflections of exposure radiation. Preferred dye compounds are polymeric materials that include one or more chromophores such as anthracene and other polycyclic moieties that effectively absorb deep UV exposure radiation.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: December 12, 2006
    Assignee: Shipley Company, L.L.C.
    Inventors: James Michael Mori, James W. Thackeray, Roger F. Sinta, Rosemary Bell, Robin L. Miller-Fahey, Timothy G. Adams, Thomas M. Zydowsky, Edward K. Pavelchek, Manuel doCanto
  • Patent number: 7144676
    Abstract: Imaging compositions and methods of using the compositions are disclosed. The imaging compositions are sensitive to low levels of energy such that upon application of the low levels of energy the compositions change color or shade. The compositions may be applied to a work piece to mark it and removed from the work piece by peeling.
    Type: Grant
    Filed: July 12, 2004
    Date of Patent: December 5, 2006
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Robert K. Barr, Corey O'Connor
  • Patent number: 7141692
    Abstract: A nonpolymeric silsesquioxane is provided wherein at least one silicon atom of the silsesquioxane is directly or indirectly bound to an acid-cleavable substituent RCL. The silsesquioxane has a glass transition temperature Tg of greater than 50° C., and the RCL substituent can be cleaved from the silsesquioxane at a temperature below Tg, generally at least 5° C. below Tg. The remainder of the silicon atoms within the silsesquioxane structure may be bound to additional acid-cleavable groups, acid-inert polar groups RP, and/or acid-inert nonpolar groups RNP. The nonpolymeric silsesquioxane can be a polyhedral silsesquioxane optionally having one to three open vertices, such that the polyhedron appears to be a “partial cage” structure, or a macromer of two to four such polyhedral silsesquioxanes. Photoresist compositions containing the novel nonpolymeric silsesquioxanes are also provided, as is a method for using the compositions in preparing a patterned substrate.
    Type: Grant
    Filed: November 24, 2003
    Date of Patent: November 28, 2006
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Wu-Song Huang, Mahmoud Khojasteh, Qinghuang Lin, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7011928
    Abstract: Disclosed is a method of forming an image on a light sensitive planographic printing plate material comprising a hydrophilic support and provided thereon, a light sensitive layer containing an addition polymerizable ethylenically unsaturated monomer, a photopolymerization initiator, a polymer binder, and a sensitizing dye having an absorption maximum in the wavelength regions of from 390 to 430 nm, the minimum laser exposure amount necessary to form an image on the material being from 1.0 to 100 ?J/cm2, the method comprising the step of imagewise exposing the light sensitive planographic printing plate material to laser under a non-yellow safelight to form an image, the non-yellow safelight having an optical filter cutting out light with a wavelength of less than 440 nm, and satisfying the following expression: 0.800<I/I700<1.00.
    Type: Grant
    Filed: January 16, 2004
    Date of Patent: March 14, 2006
    Assignee: Konica Minolta Holdings, Inc.
    Inventor: Yasuhiko Takamuki
  • Patent number: 6953652
    Abstract: A positive working printing plate precursor is disclosed which comprises a hydrophilic support and a coating provided thereon which comprises in the order given a first layer containing an oleophilic resin soluble in an aqueous alkaline developer and a second layer comprising a water repellent-compound. Furthermore, the coating comprises an infrared absorbing dye containing a polysiloxane group providing a printing plate precursor with high sensitivity.
    Type: Grant
    Filed: January 23, 2004
    Date of Patent: October 11, 2005
    Assignee: Agfa-Gevaert
    Inventors: Marc Van Damme, Geert Deroover