Identified Overlayer On Radiation-sensitive Layer Patents (Class 430/273.1)
  • Patent number: 8889334
    Abstract: Anti-reflective coating materials for ultraviolet photolithography include at least one absorbing compounds and at least one pH tuning agent that are incorporated into spin-on materials. Suitable absorbing compounds are those that absorb around wavelengths such as 365 nm, 248 nm, 193 nm and 157 nm that may be used in photolithography. Suitable pH tuning agents not only adjust the pH of the final spin-on composition, but also influence the chemical performance and characteristics, mechanical performance and structural makeup of the final spin-on composition that is part of the layered material, electronic component or semiconductor component, such that the final spin-on composition is more compatible with the resist material that is coupled to it. A method of making absorbing and pH tuned spin-on materials includes combining at least one organic absorbing compound and at least one pH tuning agent with at least one silane reactant during synthesis of the spin-on materials and compositions.
    Type: Grant
    Filed: December 3, 2012
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Joseph T Kennedy, Teresa Baldwin-Hendricks
  • Patent number: 8883379
    Abstract: A pattern is printed by forming a photoresist layer on a wafer, forming a protective film thereon, exposure, and development. The protective film is formed from a protective film-forming composition comprising a novolak resin of a bisphenol compound and a mixture of an alcohol solvent and an ether or aromatic solvent.
    Type: Grant
    Filed: December 6, 2012
    Date of Patent: November 11, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Daisuke Kori
  • Patent number: 8883407
    Abstract: In one aspect, organic coating compositions, particularly antireflective coating compositions, are provided that comprise a diene/dienophile reaction product. In another aspect, organic coating compositions, particularly antireflective coating compositions, are provided that comprise a component comprising a hydroxyl-naphthoic group, such as a 6-hydroxy-2-naphthoic group Preferred compositions of the invention are useful to reduce reflection of exposing radiation from a substrate back into an overcoated photoresist layer and/or function as a planarizing, conformal or via-fill layer.
    Type: Grant
    Filed: June 10, 2010
    Date of Patent: November 11, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: John P. Amara, James F. Cameron, Jin Wuk Sung, Gregory P. Prokopowicz
  • Patent number: 8883399
    Abstract: A photosensitive resin structure having an ablation layer for a photosensitive resin for a relief printing that is capable of being processed by infrared radiation and containing an anionic polymer, a relief printing plate is produced by drawing a pattern by irradiating the ablation layer with infrared radiation; exposing the pattern by irradiating the photosensitive resin layer with ultraviolet radiation; and removing the ablation layer and unexposed photosensitive resin layer with a developer.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: November 11, 2014
    Assignee: Asahi Kasei E-Materials Corporation
    Inventor: Chisato Iso
  • Patent number: 8883400
    Abstract: Topcoat layer compositions are provided that are applied above a photoresist composition. The compositions find particular applicability to immersion lithography processing.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: November 11, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu
  • Patent number: 8877467
    Abstract: Biomass feedstocks (e.g., plant biomass, animal biomass, and municipal waste biomass) are processed to produce useful products, such as fuels. For example, systems are described that can use feedstock materials, such as cellulosic and/or lignocellulosic materials and/or starchy materials, to produce a product or intermediate, e.g., energy, a food, a fuel, or a material.
    Type: Grant
    Filed: March 6, 2013
    Date of Patent: November 4, 2014
    Assignee: Xyleco, Inc.
    Inventors: Marshall Medoff, Thomas Craig Masterman
  • Publication number: 20140315129
    Abstract: An imageable material can be used to form a mask image for providing a relief image. This imageable material has a simplified structure and consists essentially of, in order: a transparent polymeric carrier sheet and a barrier layer comprising a first infrared radiation absorbing compound. A first ultraviolet radiation absorbing compound is provided in the transparent polymeric carrier sheet or the barrier layer. A non-silver halide thermally sensitive imageable layer is disposed on the barrier layer and comprises a second infrared radiation absorbing compound and a second ultraviolet radiation absorbing compound. A relief image is formed by imaging the imageable material to form an imaged mask material, exposing a relief-forming material with curing radiation through the imaged mask material to form exposed regions and non-exposed regions, and developing the imaged relief-forming material to form a relief image by removing its non-exposed regions.
    Type: Application
    Filed: April 18, 2013
    Publication date: October 23, 2014
    Inventor: Kevin M. Kidnie
  • Patent number: 8865391
    Abstract: A chemically amplified negative resist composition is provided comprising (A) a resin having a crosslinking group, (B) a crosslinker, (C) a photoacid generator capable of generating an acid upon exposure to light of wavelength 190-500 nm, (D) a solvent, and (E) an isocyanuric acid. The resist composition overcomes the stripping problem that the film is stripped from metal wirings of Cu or Al, electrodes, and SiN substrates.
    Type: Grant
    Filed: December 5, 2012
    Date of Patent: October 21, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Takashi Miyazaki, Hiroyuki Urano
  • Patent number: 8859194
    Abstract: A polymer compound and a resist protective film composition for an immersion lithography process including the same.
    Type: Grant
    Filed: May 17, 2013
    Date of Patent: October 14, 2014
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Man Ho Han, Jong Kyoung Park, Hyun Jin Kim, Jae Hyun Kim
  • Patent number: 8852855
    Abstract: [Object] To provide a top anti-reflection coating composition equal or superior to known products in film-formability, in refractive index, in temporal stability and in safety; and also to provide a pattern formation method using the same. [Means] A top anti-reflection coating composition comprising a solvent, an alkylsulfonic acid having 10 to 18 carbon atoms, and a fluorine-containing polymer having a weight average molecular weight of 300000 to 800000 and represented by the formula (1): -Ax-By- (1). In the formula (1), A is a repeating unit represented by the formula (A): (R is a fluorine-containing alkylene group having 1 to 40 carbon atoms or R is a fluorine-containing alkylene group having 2 to 100 carbon atoms and an ether bond); B is a repeating unit capable of combining with A to form a copolymer; x and y are numbers indicating the polymerization ratios, provided that x is not equal to 0; and A and B may randomly combine with each other or may form blocks.
    Type: Grant
    Filed: April 11, 2012
    Date of Patent: October 7, 2014
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Takayuki Sao, Tomohide Katayama
  • Patent number: 8852848
    Abstract: The present invention relates to an aqueous composition for coating over a photoresist pattern comprising a first water soluble compound comprising at least a silicon moiety and at least one amino group, and a second compound comprising at least 1 carboxylic acid group. The invention further relates to processes for using the novel invention.
    Type: Grant
    Filed: July 28, 2010
    Date of Patent: October 7, 2014
    Assignee: Z Electronic Materials USA Corp.
    Inventors: Hengpeng Wu, Meng Li, Yi Cao, Jian Yin, DongKwan Lee, SungEun Hong, Margareta Paunescu
  • Patent number: 8846303
    Abstract: There is disclosed a resist top coat composition, used in a patterning process onto a photoresist film, wherein a resist top coat is formed by using the resist top coat composition onto a photoresist film formed on a wafer, and then, after exposure, removal of the resist top coat and development of the photoresist film are performed to effect the patterning on the photoresist film, wherein the resist top coat composition contains a truxene compound having phenol groups shown by the following general formula (1). As a result, there is provided a resist top coat composition not only having an effect from an environment to a resist film reduced and effectively shielding an OOB light, but also reducing film loss of a resist pattern and bridging between patterns and having an effect to enhance sensitivity of the resist; and a patterning process using this.
    Type: Grant
    Filed: September 25, 2012
    Date of Patent: September 30, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Daisuke Kori
  • Patent number: 8841058
    Abstract: A photolithography material is provided. The photolithography material is a surface modifying material. The photolithography material includes a polymer (e.g., fluorine polymer) that includes less than approximately 80% hydroxyl groups. In an embodiment, the photolithography material includes less than approximately 80% fluoro-alcohol functional units. Methods of using the photolithography material include as an additive to a photoresist or topcoat layer. The photolithography material may be used in an immersion lithography process.
    Type: Grant
    Filed: October 27, 2010
    Date of Patent: September 23, 2014
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventor: Ching-Yu Chang
  • Patent number: 8828646
    Abstract: To provide a lithographic printing plate precursor which is excellent in the gum development property, running processing property and scratch resistance and a lithographic printing plate precursor which is good in all performances of the on-press development property, ink receptivity, sensitivity and printing durability, and a method of producing thereof. A lithographic printing plate precursor has a support, an image-recording layer containing a radical polymerization initiator and a radical polymerizable compound, and an overcoat layer containing a polymer resin which has a cloud point in an aqueous solution and includes a monomer unit containing at least any of an amino group and an amido bond, in this order.
    Type: Grant
    Filed: March 15, 2011
    Date of Patent: September 9, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Yuzo Fujiki, Shota Suzuki
  • Publication number: 20140242517
    Abstract: Negative-working lithographic printing plate precursor a negative-working imageable layer and an outermost water-soluble overcoat layer that is disposed directly on the negative-working imageable layer. The outermost water-soluble overcoat layer comprises: (1) one or more film-forming water-soluble polymeric binders, (2) organic wax particles, and (3) non-wax matte particles. The outermost water-soluble overcoat layer has a dry thickness (t) that is defined by the following equation (I): t=w/r wherein w is the dry coverage of the outermost water-soluble overcoat layer in g/m2, and r is 1 g/cm3. The organic wax particles have an average largest dimension D(wax) that is less than 0.9 of t (in ?m), and the non-wax matte particles have an average largest dimension D(matte) that defined by the following equation (II): 1.5 times t?D(matte)?40 times t (in ?m).
    Type: Application
    Filed: February 28, 2013
    Publication date: August 28, 2014
    Inventors: AKIRA IGARASHI, YUKKI TORIHATA, HARALD BAUMANN, UDO DWARS, CHRISTOPHER D. SIMPSON, SAIJA WERNER, MICHAEL FLUGEL
  • Patent number: 8808967
    Abstract: Topcoat layer compositions are provided that are applied above a photoresist composition. The compositions find particular applicability to immersion lithography processing.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: August 19, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu
  • Patent number: 8808968
    Abstract: A photocurable relief image printing element is described. The photocurable relief image printing element comprises (a) a support layer; (b) one or more photocurable layers disposed on the support layer, wherein the one or more photocurable layers comprise: (i) a binder; (ii) one or more monomers; (iii) a photoinitiator; and (iv) an additive selected from the group consisting of phosphites, phosphines, thioether amine compounds, and combinations of one or more of the foregoing; (c) a laser ablatable masking layer disposed on the one or more photocurable layers, the laser ablatable masking layer comprising a radiation opaque material; and (d) optionally, a removable coversheet. The photocurable relief image printing element provides improved surface cure in digital relief image printing elements.
    Type: Grant
    Filed: August 22, 2012
    Date of Patent: August 19, 2014
    Inventors: Jonghan Choi, Kerry O'Brate
  • Patent number: 8802357
    Abstract: A method of forming an image on a photoresist. The method includes: forming a photoresist over a substrate; applying a topcoat composition, the topcoat composition comprising at least one fluorine-containing polymer and a casting solvent, onto the photoresist; removing the casting solvent of the topcoat composition resulting in the formation of a topcoat material over the photoresist; exposing the photoresist to radiation, the radiation changing a chemical composition of the regions of the photoresist exposed to the radiation, forming exposed and unexposed regions in the photoresist; and removing i) the topcoat material and ii) the exposed regions of the photoresist or the unexposed regions of the photoresist.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: August 12, 2014
    Assignee: International Business Machines Corporation
    Inventors: Hiroshi Ito, Linda Karin Sundberg
  • Patent number: 8795949
    Abstract: To provide a resist pattern improving material, containing: a compound represented by the following general formula (1), or a compound represented by the following general formula (2), or both thereof; and water: where R1 and R2 are each independently a hydrogen atom, or a C1-C3 alkyl group; m is an integer of 1 to 3; and n is an integer of 3 to 30, where p is an integer of 8 to 20; q is an integer of 3 to 30; and r is an integer of 1 to 8.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: August 5, 2014
    Assignee: Fujitsu Limited
    Inventors: Miwa Kozawa, Koji Nozaki
  • Patent number: 8771919
    Abstract: A process to mark a multilayered article with a laser (20). The multilayered article (10) includes a laser-markable layer (14) having at least one organic polymer and at least one light-sensitive pigment therein, and including at least one release agent associated with the laser-markable layer. Laser-marking of the laser-markable layer is accomplished by directing laser radiation (22) into the multilayered article through the release agent (12) to induce an interaction between the light-sensitive pigment and the organic polymer. As a result of the interaction, a visually perceptible marking (16) is formed in the article. The laser-marked article includes a laser-markable layer and a first release agent associated with a surface of the laser-markable layer. The marking(s) in the laser-markable layer is visible through the layer of release agent, and the marking is a result of the laser-induced interaction between the light-sensitive pigment and the organic polymer.
    Type: Grant
    Filed: August 31, 2010
    Date of Patent: July 8, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Pingfan Wu, Junkang Jacob Lui, Robert L. W. Smithson, Rachel M. Lucking, Panu K. Zoller, Jeffrey O. Emslander, Kanta Kumar
  • Publication number: 20140178814
    Abstract: There is provided a dry film photoresist including: a base film having an oxygen permeable barrier layer formed thereon; a photosensitive resin layer formed on the oxygen permeable barrier layer; and a protective film formed on the photosensitive resin layer. According to the present invention, the dry film photoresist includes the oxygen permeable barrier layer formed on the base film to prevent a curing reaction from being deteriorated by oxygen permeation in the dry film photoresist, such that residue that is not peeled off may be decreased, thereby significantly decreasing process defects.
    Type: Application
    Filed: March 11, 2013
    Publication date: June 26, 2014
    Applicant: SAMSUNG ELECTRO-MECHANICS CO., LTD.
    Inventor: SAMSUNG ELECTRO-MECHANICS CO. LTD.
  • Patent number: 8748060
    Abstract: A coating including an oligomer is disclosed, the oligomer being the reaction product of an epoxy silane, a multifunctional (meth)acrylate; and a polymerizable fluorochemical. The polymerizable fluorochemical can be fluorinated (meth)acrylate or a polymerizable fluorinated urethane. Phototools having a layer of the coating on a substrate can be made. A method of making a printed assembly such as a printed circuit board is also disclosed.
    Type: Grant
    Filed: September 14, 2010
    Date of Patent: June 10, 2014
    Assignee: 3M Innovative Properties Company
    Inventor: Zai-Ming Qiu
  • Patent number: 8748080
    Abstract: Topcoat layer compositions are provided that are applied above a photoresist composition. The compositions find particular applicability to immersion lithography processing.
    Type: Grant
    Filed: December 31, 2009
    Date of Patent: June 10, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu
  • Patent number: 8748077
    Abstract: To provide a resist pattern improving material, containing: water; and benzalkonium chloride represented by the following general formula (1): where n is an integer of 8 to 18.
    Type: Grant
    Filed: January 26, 2012
    Date of Patent: June 10, 2014
    Assignee: Fujitsu Limited
    Inventors: Koji Nozaki, Miwa Kozawa
  • Patent number: 8741536
    Abstract: A radiation sensitive composition which is primarily sensitive in the near UV and visible region of the electromagnetic spectrum is composed of a polymeric binder, an ethylenically unsaturated monomer, a radiation absorbing compound, a photoaccelerator, an onium compound, and an adhesion promoter, which are overcoated with an oxygen barrier layer. When applied to the proper support and processed, the composition is useful as an offset lithographic printing plate, color proofing film or image resist.
    Type: Grant
    Filed: September 24, 2003
    Date of Patent: June 3, 2014
    Assignee: IBF Industria Basileira de Filmes S/A
    Inventors: André Luiz Arias, Luiz Nel Arias, Marjorie Arias, Mario Italo Provenzano
  • Patent number: 8728779
    Abstract: Biomass (e.g., plant biomass, animal biomass, microbial, and municipal waste biomass) is processed to produce useful products, such as food products and amino acids.
    Type: Grant
    Filed: December 6, 2011
    Date of Patent: May 20, 2014
    Assignee: XYLECO, Inc.
    Inventor: Marshall Medoff
  • Patent number: 8728706
    Abstract: A radiation-sensitive resin composition includes a first polymer including an acid-labile group, an acid generator to generate an acid upon exposure to radiation, and a second polymer including a fluorine atom and a functional group shown by a general formula (x). The second polymer has a fluorine atom content higher than a fluorine atom content of the first polymer. R1 represents an alkali-labile group. A represents an oxygen atom, —NR?—, —CO—O—# or —SO2—O—##, wherein the oxygen atom represented by A is not an oxygen atom bonded directly to an aromatic ring, a carbonyl group, or a sulfoxyl group, R? represents a hydrogen atom or an alkali-labile group, and “#” and “##” indicates a bonding hand bonded to R1.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: May 20, 2014
    Assignee: JSR Corporation
    Inventors: Yuusuke Asano, Mitsuo Satou, Hiromitsu Nakashima, Kazuki Kasahara, Yoshifumi Oizumi, Masafumi Hori, Takanori Kawakami, Yasuhiko Matsuda, Kazuo Nakahara
  • Patent number: 8715907
    Abstract: A negative developable bottom antireflective coating (NDBARC) material includes a polymer containing an aliphatic alcohol moiety, an aromatic moiety, and a carboxylic acid moiety. The NDBARC composition is insoluble in a typical resist solvent such as propylene glycol methyl ether acetate (PGMEA) after coating and baking. The NDBARC material also includes a photoacid generator, and optionally a crosslinking compound. In the NDBARC material, the carboxylic acid provides the developer solubility, while the alcohol alone, the carboxylic acid alone, or their combination provides the PGMEA resistance. The NDBARC material has resistance to the resist solvent, and thus, intermixing does not occur between NDBARC and resist during resist coating over NDBARC.
    Type: Grant
    Filed: August 10, 2011
    Date of Patent: May 6, 2014
    Assignee: International Business Machines Corporation
    Inventors: Kuang-Jung Chen, Steven J. Holmes, Wu-Song Huang, Sen Liu
  • Patent number: 8715911
    Abstract: Provided are a coating composition for deep ultraviolet (DUV) filtering during an extreme ultraviolet (EUV) exposure, the coating composition including about 100 parts by weight of a solvent including a first solvent (the first solvent being an alcoholic solvent); and about 0.05 parts by weight to about 5 parts by weight of a coating polymer having a degree of absorption of about 50%/?m or greater with respect to 193-nm incident light.
    Type: Grant
    Filed: July 22, 2011
    Date of Patent: May 6, 2014
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyun-woo Kim, Hai-sub Na, Chil-hee Chung, Han-ku Cho
  • Patent number: 8697330
    Abstract: There is disclosed a thermosetting silicon-containing antireflection film-forming composition, to form a silicon-containing antireflection film in a multilayer resist process used in a lithography, wherein the composition is at least capable of forming—on an organic film that is an underlayer film having a naphthalene skeleton—a silicon-containing antireflection film whose refractive index “n” and extinction coefficient “k” at 193 nm satisfy the following relationship: 2n?3.08?k?20n?29.4 and 0.01?k?0.5.
    Type: Grant
    Filed: April 23, 2010
    Date of Patent: April 15, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsutomu Ogihara, Toshiharu Yano, Takafumi Ueda
  • Patent number: 8697344
    Abstract: A composition for forming an upper layer film includes a solvent and a resin component including a first resin having a first repeating unit and a second repeating unit. The first repeating unit is a repeating unit represented by a formula (1-1), a repeating unit represented by a formula (1-2), a repeating unit represented by a formula (1-3), or a combination thereof. The second repeating unit is a repeating unit represented by a formula (2-1), a repeating unit represented by a formula (2-2), or both thereof. The composition is to be used for forming the upper layer film in liquid immersion lithography.
    Type: Grant
    Filed: April 1, 2013
    Date of Patent: April 15, 2014
    Assignee: JSR Corporation
    Inventors: Daita Kouno, Norihiko Sugie, Gouji Wakamatsu, Norihiro Natsume, Yukio Nishimura, Makoto Sugiura
  • Patent number: 8685623
    Abstract: Embodiments of the present invention involve three-layer printing members having a central layer that is non-conductive yet abalatable at commercially realistic fluence levels. In various embodiments, the central layer is polymeric with a dispersion of nonconductive carbon black particles therein at a loading level sufficient to provide at least partial layer ablatability and water compatibility of the resulting ablation debris.
    Type: Grant
    Filed: January 25, 2013
    Date of Patent: April 1, 2014
    Assignee: Presstek, Inc.
    Inventors: Sonia Rondon, Kevin Ray
  • Patent number: 8679727
    Abstract: A developing method for immersion lithography is provided, realizing a process that is simple and low-cost and enables high repellency sufficient to allow high-speed scanning. The developing method for immersion lithography improved by inexpensive material without introducing any new facility, a solution to be used in the developing method, and an electronic device formed by using the developing method are provided. The developing method for immersion lithography is a method of developing for immersion lithography of an electronic device with a resist containing a surface segregation agent and chemically-amplified resist, including the step of development with alkali immersion, characterized by the dissolving and removing step, conducted using a dissolving and removing solution that selectively dissolves and removes the surface segregation agent of the resist.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: March 25, 2014
    Assignee: Renesas Electronics Corporation
    Inventors: Mamoru Terai, Takuya Hagiwara, Miwako Ishibashi
  • Patent number: 8673537
    Abstract: The invention relates to a photo-curable resin composition, which contains a polyimide silicone having a primary alcoholic hydroxyl group, as a component (A); at least one compound selected from the group consisting of an amino condensation product modified with formalin or a formalin-alcohol and a phenol compound having two or more in average of methylol group or alkoxymethylol group in one molecule thereof, as a component (B); and a photo-acid generator as a component (C). When used as an adhesive, the photo-curable resin composition further contains a multifunctional epoxy compound as a component (D).
    Type: Grant
    Filed: December 9, 2010
    Date of Patent: March 18, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masahiro Furuya, Michihiro Sugo, Hideto Kato, Kazunori Kondo, Shohei Tagami, Tomoyuki Goto
  • Patent number: 8669041
    Abstract: A method of making a relief image printing element having a relief pattern comprising a plurality of relief dots, wherein the photocurable printing blank comprises a backing layer having at least one photocurable layer disposed thereon and a masking layer on the at least one photocurable layer is provided. The method comprising the steps of: a) selectively ablating the masking layer to create an overall image in the masking layer, such that the overall image comprises a sub-image, comprising a pattern of cells, in it; b) applying an oxygen barrier layer on top of the masking layer; c) exposing the printing element to actinic radiation through the oxygen barrier layer and the masking layer; and d) developing the printing blank by removing the barrier layer and the uncured portions of the photocurable layer to reveal the relief image.
    Type: Grant
    Filed: July 15, 2011
    Date of Patent: March 11, 2014
    Inventors: Brian Cook, David A. Recchia, Timothy Gotsick
  • Patent number: 8663904
    Abstract: Embodiments in accordance with the present invention provide for non-self imageable norbornene-type polymers useful for immersion lithographic processes, methods of making such polymers, compositions employing such polymers and immersion lithographic processes that make use of such compositions. More specifically the embodiments of the present invention are related to norbornene-type polymers useful for forming top-coat layers for overlying photoresist layers in immersion lithographic process and the process thereof.
    Type: Grant
    Filed: August 7, 2013
    Date of Patent: March 4, 2014
    Assignee: Promerus, LLC
    Inventors: Pramod Kandanarachchi, Kazuyoshi Fujita, Steven Smith, Larry F Rhodes
  • Patent number: 8663903
    Abstract: Disclosed is a top coating composition formed on a resist film, for protecting the resist film, the top coating composition being a top coating composition for photoresist, characterized by containing a fluorine-containing polymer having a repeating unit represented by the following general formula (1). This composition is capable of controlling developing solution solubility and has a high water repellency. [In the formula, R1 represents a hydrogen atom, fluorine atom, methyl group or trifluoromethyl group, R2 represents a heat-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W is a bivalent linking group.
    Type: Grant
    Filed: April 20, 2010
    Date of Patent: March 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazuhiko Maeda, Takamasa Kitamoto, Haruhiko Komoriya, Satoru Narizuka, Yoshimi Isono, Kazunori Mori
  • Publication number: 20140057204
    Abstract: A negative-working lithographic printing plate precursor comprises a negative-working radiation-sensitive imageable layer and an outermost layer comprising a vinyl alcohol copolymer comprising at least one unit of each of the (a), (b), and (c) recurring units, in any order, defined in the disclosure. The (c) recurring units are present in the vinyl alcohol copolymer in an amount of at least 0.5 mol %, based on the total recurring units. These precursors can be used to prepare lithographic printing plates either on-press or off-press after imaging using near-UV, visible, or infrared radiation.
    Type: Application
    Filed: August 22, 2012
    Publication date: February 27, 2014
    Inventors: Saija Werner, Harald Bauman, Udo Dwars, Christopher D. Simpson, Axel Draber
  • Patent number: 8658341
    Abstract: There is provided to a pattern reversal film forming composition that is capable of forming a pattern reversal film which is not mixed with a resist pattern formed on a substrate, and that is only capable of forming a pattern reversal film advantageously covering the pattern, but also irrespective of whether the resist pattern is coarse or fine, capable of forming a planar film excellent in temporal stability on the pattern. A pattern reversal film forming composition including a polysiloxane, an additive and an organic solvent, characterized in that the polysiloxane is a product of a hydrolysis and/or condensation reaction of a silane compound containing a tetraalkoxysilane of Si(OR1)4 and an alkoxysilane of XnSi(OR2)4-n, and the tetraalkoxysilane is used in a ratio of 1 to 50% by mole based on the number of moles of the whole silane compound; and a pattern reversal film and a method of forming a reversed pattern in which the composition is used.
    Type: Grant
    Filed: April 21, 2010
    Date of Patent: February 25, 2014
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Daisuke Maruyama, Hiroaki Yaguchi, Yasushi Sakaida
  • Patent number: 8652761
    Abstract: A method of thermally developing photocurable printing blank to produce a relief pattern comprising a plurality of relief dots. The photocurable printing blank comprises a backing layer having at least one photocurable layer disposed thereon and a laser ablatable mask layer disposed on top of the at least one photocurable layer. The method includes the steps of (1) imaging the at least one photocurable layer by ablating portions of the laser ablatable mask layer; (2) laminating an oxygen barrier membrane to a top of the laser ablated mask layer; (3) exposing the printing blank to actinic radiation through the oxygen barrier membrane and mask layer to actinic radiation, thereby creating the relief pattern; (4) removing the oxygen barrier membrane; and (5) thermally developing the printing blank to remove the laser ablated mask layer and uncured portions of the photocurable layer and reveal the relief pattern. The presence of the oxygen harrier membrane produces printing dots having desired characteristics.
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: February 18, 2014
    Inventors: David A. Recchia, Joseph H. Blair, Ryan W. Vest
  • Patent number: 8647809
    Abstract: Metal-oxide films for lithographic applications are provided. The films are formed from compositions comprising metal-oxide precursor compounds including metals and metalloids other than silicon. These films are easily produced and can be modified with a variety of ligands, including alkoxides, phenoxides, carboxylates, beta-diketones, and beta-ketoesters.
    Type: Grant
    Filed: July 7, 2011
    Date of Patent: February 11, 2014
    Assignee: Brewer Science Inc.
    Inventors: Daniel M. Sullivan, Charles J. Neef, Yubao Wang, Tantiboro Ouattara
  • Publication number: 20140038104
    Abstract: A water dispersible composition comprises a polyaniline copolymer having a weight average molecular weight of at least 30,000 and a polymeric acid comprising sulfonic acid groups. The polyaniline copolymer comprises i) about 10 mol % to about 15 mol % of a fluorine-containing first aniline repeat unit based on total moles of repeat units in the polyaniline copolymer, and ii) a second aniline repeat unit comprising no fluorine. The sulfonic acid groups of the polymeric acid are present in a molar amount greater than or equal to total moles of repeat units of the polyaniline copolymer. The composition has a conductivity of at least 0.0001 S/cm.
    Type: Application
    Filed: July 31, 2012
    Publication date: February 6, 2014
    Applicants: SHIN-ETSU CHEMICAL CO., LTD., INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Luisa Dominica Bozano, Takayuki Nagasawa, Mark Hull Sherwood, Ratnam Sooriyakumaran, Linda Karin Sundberg, Satoshi Watanabe
  • Patent number: 8632959
    Abstract: A printing plate assembly for use in flexographic printing application is provided which includes an integral carrier layer, one or more cushion layers, and one or more photopolymer layers. The photopolymer layer(s) in the integral assembly are provided with relief images using digital imaging photopolymerization, which eliminates the need for a back exposure step and provides a precise relief depth for the plate.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: January 21, 2014
    Assignee: Day International, Inc.
    Inventors: Michael E. McLean, William Krebs Goss
  • Patent number: 8632942
    Abstract: A method of forming patterns includes (a) coating a substrate with a resist composition for negative development to form a resist film having a receding contact angle of 70 degrees or above with respect to water, wherein the resist composition for negative development contains a resin capable of increasing the polarity by the action of an acid and becomes more soluble in a positive developer and less soluble in a negative developer upon irradiation with an actinic ray or radiation, (b) exposing the resist film via an immersion medium, and (c) performing development with a negative developer.
    Type: Grant
    Filed: November 29, 2011
    Date of Patent: January 21, 2014
    Assignee: FUJIFILM Corporation
    Inventor: Hideaki Tsubaki
  • Patent number: 8632948
    Abstract: The invention relates to a photoimageable antireflective coating composition capable of forming a pattern by development in an aqueous alkaline solution, comprising, (i) a polymer A soluble in a coating solvent and comprises a chromophore, a crosslinking moiety, and optionally a cleavable group which under acid or thermal conditions produces a functionality which aids in the solubility of the polymer in an aqueous alkaline solution and; (ii) at least one photoacid generator; (iii) a crosslinking agent; (iv) optionally, a thermal acid generator; (v) a polymer B which is soluble in an aqueous alkaline solution prior to development, where polymer B is non-miscible with polymer A and soluble in the coating solvent, and; (vi) a coating solvent composition, and (vii) optionally, a quencher. The invention also relates to a process for imaging the antireflective coating.
    Type: Grant
    Filed: September 30, 2009
    Date of Patent: January 21, 2014
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Munirathna Padmanaban, Srinivasan Chakrapani, Francis M. Houlihan, Shinji Miyazaki, Edward Ng, Mark O. Neisser
  • Patent number: 8632940
    Abstract: Electrochemically grained and anodized aluminum supports are treated with a post-treatment coating solution containing a polymer derived at least in part from vinyl phosphonic acid and phosphoric acid. This post-treated support is useful as substrates in the preparation of lithographic printing plate precursors. The post-treatment substrate treatment enables wide latitude in manufacturing and compatibility with silicate-free developers to achieve negligible background staining and oxide attack.
    Type: Grant
    Filed: April 19, 2011
    Date of Patent: January 21, 2014
    Assignee: Eastman Kodak Company
    Inventors: Gerhard Hauck, Celin Savariar-Hauck, Oliver R. Blum, Michael Nielinger
  • Patent number: 8628896
    Abstract: A member for masking films including a base film transparent to ultraviolet rays, an ultraviolet-shielding resin layer capable of being removed by irradiation with a laser light beam and having an average thickness of 0.1 to 30 ?m, and a protective layer having a thickness of 0.05 to 1.5 ?m and comprising, as a resin component, a polyester-base resin having a glass-transition temperature of not less than 40° C. laminated to a surface of the outermost layer of the ultraviolet-shielding resin layer, wherein the ultraviolet-shielding resin layer is a multilayer structure composed of two or more layers including a resin layer (A) having a high carbon black content and a resin layer (B) having a low carbon black content, the layer (A) and the layer (B) being located on the base-film side and on the printing-plate side of the ultraviolet-shielding resin layer, respectively.
    Type: Grant
    Filed: March 25, 2010
    Date of Patent: January 14, 2014
    Assignee: LINTEC Corporation
    Inventors: Takeshi Ikeda, Toshihiro Tsutsui, Masafumi Mitsuhashi
  • Patent number: 8618217
    Abstract: A topcoat composition to be applied on a resist film is provided, the topcoat composition including: (A) an alkali-soluble resin; (B) a compound containing at least one of an Si atom and an F atom, and increasing a contact angle on a surface of the topcoat film; and (C) a solvent.
    Type: Grant
    Filed: November 14, 2008
    Date of Patent: December 31, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shinichi Kanna
  • Patent number: 8617794
    Abstract: A method of forming patterns includes (a) coating a substrate with a resist composition for negative development to form a resist film, wherein the resist composition contains a resin capable of increasing the polarity by the action of the acid and becomes more soluble in a positive developer and less soluble in a negative developer upon irradiation with an actinic ray or radiation, (b) forming a protective film on the resist film with a protective film composition after forming the resist film and before exposing the resist film, (c) exposing the resist film via an immersion medium, and (d) performing development with a negative developer.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: December 31, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Hideaki Tsubaki
  • Patent number: 8603729
    Abstract: A lithographic printing plate precursor includes, in the following order: a support; an image-recording layer which is capable of forming an image by removing an unexposed area with at least one of printing ink and dampening water on a printing machine after exposure and contains (A) an infrared absorbing dye, (B) a polymerization initiator, (C) a polymerizable compound and (D) a binder polymer having an alkylene oxide group; and a protective layer containing (E) a hydrophilic polymer containing at least a repeating unit represented by the formula (1) as defined herein and a repeating unit represented by the formula (2) as defined herein.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: December 10, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Shota Suzuki, Yuriko Ishiguro