Polymeric Quinone Diazide Patents (Class 430/190)
  • Patent number: 10818703
    Abstract: A method for manufacturing a semiconductor device includes: forming a photocatalytic layer and an organic compound layer in contact with the photocatalytic layer over a substrate having a light transmitting property; forming an element forming layer over the substrate having the light transmitting property with the photocatalytic layer and the organic compound layer in contact with the photocatalytic layer interposed therebetween; and separating the element forming layer from the substrate having the light transmitting property after the photocatalytic layer is irradiated with light through the substrate having the light transmitting property.
    Type: Grant
    Filed: July 20, 2016
    Date of Patent: October 27, 2020
    Assignee: Semiconductor Energy Laboratory Co., Ltd.
    Inventors: Masafumi Morisue, Yasuhiro Jinbo, Gen Fujii, Hajime Kimura
  • Patent number: 10793741
    Abstract: Organic-inorganic composite particles including: inorganic particles; and an organic polymer, wherein the inorganic particles have surfaces on which no modification treatment for introducing a polymerizable reactive group is conducted, the organic polymer comprises a hydrophilic block arranged on the surfaces of the inorganic particles and made of a first polymer, and a hydrophobic block stacked on an outside of the hydrophilic block and made of a second polymer, and the inorganic particles, the first polymer, and the second polymer have surface free energies satisfying a condition expressed by the following formula: ENP>EA>EB [in the formula, ENP represents the surface free energy of the inorganic particles, EA represents the surface free energy of the first polymer, and EB represents the surface free energy of the second polymer].
    Type: Grant
    Filed: May 4, 2018
    Date of Patent: October 6, 2020
    Assignee: TOHOKU UNIVERSITY
    Inventor: Toshihiko Arita
  • Patent number: 10719015
    Abstract: A laminate comprising a thermoplastic film and a positive resist film is provided, the positive resist film comprising (A) a novolak resin-naphthoquinone diazide (NQD) base resin composition, (B) a polyester, and (C) 3-30 wt % of an organic solvent. The resist film may be transferred to a stepped support without forming voids.
    Type: Grant
    Filed: April 11, 2018
    Date of Patent: July 21, 2020
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Yoshinori Hirano, Satoshi Asai, Kazunori Kondo
  • Patent number: 10414850
    Abstract: Provided are a resin containing phenolic hydroxyl groups having excellent developability, heat resistance, and substrate followability, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl group. The resin containing phenolic hydroxyl groups obtained by reacting a novolac resin intermediate obtained by reacting a triarylmethane compound (A) with an aldehyde compound (B) as essential components, with an alkene compound (C) having 9 to 24 carbon atoms, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl groups.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: September 17, 2019
    Assignee: DIC Corporation
    Inventors: Tomoyuki Imada, Yusuke Sato
  • Patent number: 9983477
    Abstract: The invention relates to new polymers that comprise units that contain one or more photoacid generator groups and photoresists that contain the polymers. Preferred polymers of the invention are suitable for use in photoresists imaged at short wavelengths such as sub-250 nm or sub-200 nm, particularly 248 nm and 193 nm.
    Type: Grant
    Filed: November 22, 2010
    Date of Patent: May 29, 2018
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Roger A. Nassar
  • Patent number: 9650538
    Abstract: A micro-structure is manufactured by patterning a sacrificial film, forming an inorganic material film on the pattern, providing the inorganic material film with an aperture, and etching away the sacrificial film pattern through the aperture to define a space having the contour of the pattern. The patterning stage includes the steps of (A) forming a sacrificial film using a composition comprising a cresol novolac resin and a crosslinker, (B) exposing patternwise the film to first high-energy radiation, (C) developing, and (D) exposing the sacrificial film pattern to second high-energy radiation and heat treating for thereby forming crosslinks within the cresol novolac resin.
    Type: Grant
    Filed: June 16, 2014
    Date of Patent: May 16, 2017
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Hideto Kato, Hiroshi Kanbara, Tomoyoshi Furihata, Yoshinori Hirano
  • Patent number: 9625812
    Abstract: The photosensitive resin composition of the present invention contains a vinyl-based (co)polymer (I) obtained by polymerizing a monomer mixture (?) containing a vinyl-based monomer (a) having a phenolic hydroxyl group, a vinyl-based copolymer (II) having a weight-average molecular weight of 15,000 to 120,000, obtained by polymerizing a monomer mixture (?) containing a vinyl-based monomer (b) represented by CH2?CR1COO(R2O)kR3 (wherein R1=a hydrogen atom or a methyl group, R2=a hydrocarbon group having a carbon number of 1 to 4, R3=a hydrogen atom or a methyl group, and k=1 to 90) and a carboxyl group-containing vinyl-based monomer (c), a photosensitive substance (III), and a compound (IV) which is a specific aromatic polyhydroxy compound.
    Type: Grant
    Filed: July 2, 2013
    Date of Patent: April 18, 2017
    Assignee: MICRO PROCESS INC.
    Inventors: Akifumi Ueda, Hidetaka Nakagawara, Shintaro Okada, Saki Fujita, Kazuo Watanabe, Shigeki Watanabe
  • Patent number: 9429842
    Abstract: Disclosed are a positive photosensitive resin composition including (A) an alkali soluble resin, (B) a photosensitive diazoquinone compound, (C) a thermosetting cross-linking agent represented by the following Chemical Formula 1, wherein each substituent of Chemical Formula 1 is the same as defined in the detailed description, and (D) a solvent, a photosensitive resin film using the same, and a display device.
    Type: Grant
    Filed: July 30, 2014
    Date of Patent: August 30, 2016
    Assignee: Samsung SDI Co., Ltd.
    Inventors: Ji-Yun Kwon, Jin-Young Lee, Bum-Jin Lee, Jae-Hwan Song
  • Patent number: 9323147
    Abstract: Disclosed are a photosensitive resin composition including (A) an alkali soluble resin; (B) a photosensitive diazoquinone compound; (C) a phenol compound; (D) a thermal acid generator; and (E) a solvent, wherein the solvent includes an organic solvent having a boiling point of less than about 160° C. under an atmospheric pressure and an organic solvent having a boiling point of greater than or equal to about 160° C. under an atmospheric pressure, wherein the organic solvent having a boiling point of less than about 160° C. is included in an amount of greater than or equal to about 90 wt % and less than about 100 wt % based on the total amount of the solvent, and the organic solvent having a boiling point of greater than or equal to about 160° C. is included in an amount of greater than about 0 wt % and less than or equal to about 10 wt % based on the total amount of the solvent, a photosensitive resin film using the same, and a display device.
    Type: Grant
    Filed: July 29, 2014
    Date of Patent: April 26, 2016
    Assignee: Samsung SDI Co., Ltd.
    Inventors: Jong-Hwa Lee, Ji-Yun Kwon, Sang-Soo Kim, Kun-Bae Noh, Eun-Bi Park, Jae-Yeol Baek, Bum-Jin Lee, Sang-Haeng Lee, Eun-Ha Hwang
  • Patent number: 8993209
    Abstract: The present invention relates to a positive type photosensitive resin composition and an organic light emitting device black bank comprising the same, and more particularly, an organic light emitting device black bank comprising the photosensitive resin composition according to the exemplary embodiment of the present invention may further have a function of a black matrix without an additional process, such that it is possible to simplify a manufacturing process of the organic light emitting device and largely improve visibility.
    Type: Grant
    Filed: July 12, 2011
    Date of Patent: March 31, 2015
    Assignee: LG Chem, Ltd.
    Inventors: Sang-Woo Kim, Se-Jin Shin, Kyung-Jun Kim
  • Patent number: 8835091
    Abstract: A micro-structure is manufactured by patterning a sacrificial film, forming an inorganic material film on the pattern, and etching away the sacrificial film pattern through an aperture to define a space having the contour of the pattern. The patterning stage includes the steps of (A) coating a substrate with a composition comprising a cresol novolac resin, a crosslinker, and a photoacid generator, (B) heating to form a sacrificial film, (C) patternwise exposure, (D) development to form a sacrificial film pattern, and (E) forming crosslinks within the cresol novolac resin.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yoshinori Hirano, Hideyoshi Yanagisawa
  • Patent number: 8785103
    Abstract: Disclosed is a photosensitive novolac resin including a structural unit represented by the following Chemical Formula 1 and structural unit represented by the following Chemical Formula 2, wherein R11, R12, R13, and R14 in Chemical Formulae 1 and 2 are the same as defined in the detailed description, a positive photosensitive resin composition including the same, a photosensitive resin film fabricated using the same, and a semiconductor device including the photosensitive resin composition.
    Type: Grant
    Filed: August 21, 2012
    Date of Patent: July 22, 2014
    Assignee: Cheil Industries Inc.
    Inventors: Jong-Hwa Lee, Hyun-Yong Cho, Min-Kook Chung, Ji-Young Jeong, Myoung-Hwan Cha
  • Patent number: 8785114
    Abstract: A micro-structure is manufactured by patterning a sacrificial film, forming an inorganic material film on the pattern, providing the inorganic material film with an aperture, and etching away the sacrificial film pattern through the aperture to define a space having the contour of the pattern. The patterning stage includes the steps of (A) forming a sacrificial film using a composition comprising a cresol novolac resin and a crosslinker, (B) exposing patternwise the film to first high-energy radiation, (C) developing, and (D) exposing the sacrificial film pattern to second high-energy radiation and heat treating for thereby forming crosslinks within the cresol novolac resin.
    Type: Grant
    Filed: June 10, 2011
    Date of Patent: July 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Hiroshi Kanbara, Tomoyoshi Furihata, Yoshinori Hirano
  • Patent number: 8753790
    Abstract: Embodiments in accordance with the present invention encompass self-imageable film forming compositions that comprise norbornene-type polymers and that can be formulated to be either positive tone imaging or negative tone. The films formed thereby are useful in the forming of microelectronic and optoelectronics devices.
    Type: Grant
    Filed: June 30, 2010
    Date of Patent: June 17, 2014
    Assignee: Promerus, LLC
    Inventors: Osamu Onishi, Haruo Ikeda, Larry Rhodes, Paul Evans, Edmund Elce, Andrew Bell, Chad Brick, Hendra Ng, Pramod Kandanarachchi
  • Patent number: 8748850
    Abstract: An energy application device applies optical energy on an adhesion sheet by a light radiator and, subsequently, applies heat energy on the adhesion sheet by a heater. With this arrangement, even the adhesion sheet, which includes an adhesive layer having an energy barrier that cannot be overcome only with optical energy, is enabled to start a photoreaction by overcoming an energy barrier with the heat energy from the heater.
    Type: Grant
    Filed: August 2, 2010
    Date of Patent: June 10, 2014
    Assignee: Lintec Corporation
    Inventor: Kimihiko Kawasaki
  • Patent number: 8709552
    Abstract: The resin composition of the present invention is a resin composition characterized by including (a) a polyimide, a polybenzoxazole, a polyimide precursor or a polybenzoxazole precursor, (b) 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, or 2,3-dihydroxynaphthalene, and (c) a thermal cross-linking agent having a specific structure. By the use of the resin composition of the present invention, it is possible to reduce the transmittance in the visible region of a cured film while maintaining the transmittance of a resin film before curing.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: April 29, 2014
    Assignee: Toray Industries, Inc.
    Inventors: Kazuto Miyoshi, Mika Koshino, Masao Tomikawa
  • Patent number: 8133650
    Abstract: A polyester resin which includes acid components having aromatic dibasic acid component and trivalent or higher acid component; alcohol components including aliphatic, aromatic or cycloaliphatic diol component, and trihydric or higher alcohol component; polyolefin polyol having 1,800 to 2,500 number average molecular weight and hydroxyl value of 40 to 55 KOHmg/g; and wax having melting point of 80 to 110, wherein the amount of the polyolefin polyol is 0.1 to 2 weight % and the amount of the wax is 0.5 to 15 weight % with respect to the total polyester resin. Also disclosed is a method for preparing polyester resin by (a) carrying out an esterification reaction or an ester exchange reaction with the acid components, the alcohol components, and the polyolefin polyol; and (b) carrying out a polycondensation reaction for reaction product of the esterification or ester exchange reaction in the presence of the wax.
    Type: Grant
    Filed: July 10, 2008
    Date of Patent: March 13, 2012
    Assignee: SK Chemicals Co., Ltd.
    Inventors: Young-Man Yoo, Jae-Kyoung Roh, Kye-Yune Lee, Tae-Woong Lee
  • Patent number: 7858275
    Abstract: A positive photosensitive resin composition with favorable heat resistance and transparency is provided. The photosensitive resin composition contains a resin component (A1) having a structural unit (a1?) obtained by substituting at least a portion of hydrogen atoms of phenolic hydroxyl groups within a structural unit represented by a general formula (a1) shown below with a naphthoquinone-1,2-diazide-5-(and/or -4-) sulfonyl group. (In the above general formula, R0 represents a hydrogen atom or methyl group, R1 represents a single bond or an alkylene group of 1 to 5 carbon atoms, R2 represents an alkyl group of 1 to 5 carbon atoms, a represents an integer from 1 to 5, b represents either 0 or an integer from 1 to 4, and a+b is no greater than 5. If two or more R2 groups exist, then these R2 groups may be either the same or mutually different.
    Type: Grant
    Filed: March 10, 2006
    Date of Patent: December 28, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroyuki Ohnishi, Yasuaki Sugimoto, Isao Tateno, Masaru Shida
  • Patent number: 7803510
    Abstract: A heat resistant positive-working photosensitive PBO precursor composition comprising: (a) at least one polybenzoxazole precursor polymer; (a) at least one plasticizer compound; (b) at least one solvent; wherein the amount of the plasticizer present in the composition is an amount effective to reduce the sidewall angle of imaged and cured features in the coated film on the substrate to prevent stress failures in subsequent metallization of the substrate due to steep angles of the imaged features, and with the proviso that if the polybenzoxazole precursor polymer solely consists of polybenzoxazole precursor polymers that do not contain a photoactive moiety on the polymer, then (c) at least one photoactive compound is also present in the composition.
    Type: Grant
    Filed: August 7, 2006
    Date of Patent: September 28, 2010
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, Donald W. Racicot, Il'ya Rushkin, William D. Weber
  • Patent number: 7736833
    Abstract: Multilayered resist structures including bilayer and top surface imaging which utilize tuned underlayers functioning as ARCs, planarizing layers, and etch resistant hard masks whose properties such as optical, chemical and physical properties are tailored to give a multilayer resist structure exhibiting high resolution, residue free lithography and methods of preparing these materials.
    Type: Grant
    Filed: October 2, 2007
    Date of Patent: June 15, 2010
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Katherina E. Babich, Douglas Charles LaTulipe, Qinghuang Lin, David R. Medeiros, Wayne Martin Moreau, Karen E. Petrillo, John P. Simons
  • Patent number: 7462436
    Abstract: There is provided a positive photoresist composition capable of forming a pattern with excellent resolution, excellent resistance to reflection off the substrate, and excellent perpendicularity. The positive photoresist composition comprises (A) an alkali-soluble novolak resin in which a portion of the hydrogen atoms of all the phenolic hydroxyl groups are substituted with 1,2-naphthoquinonediazidesulfonyl groups, and (B) a dissolution promoter represented by a general formula (b-1) and/or a general formula (b-11) shown below.
    Type: Grant
    Filed: July 13, 2004
    Date of Patent: December 9, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuo Masuda, Toshiki Okui
  • Patent number: 7416830
    Abstract: A positive-working photosensitive composition comprising one or more polybenzoxazole precursor polymers, a diazonaphthoquinone photoactive compound which is the condensation product of a compound containing from 2 to about 9 aromatic hydroxyl groups with a 5-naphthoquinone diazide sulfonyl compound and a 4-naphthoquinone diazide sulfonyl compound, and at least one solvent, and the use of such compositions to form a relief pattern on a substrate thereby forming a coated substrate.
    Type: Grant
    Filed: February 18, 2005
    Date of Patent: August 26, 2008
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, Richard Hopla, David B. Powell, Jon Metivier, Il'ya Rushkin
  • Patent number: 7407731
    Abstract: A photosensitive resin composition comprising: (a) at least one polybenzoxazole precursor polymer; (b) at least one compound having Structure VI ?wherein, V is CH or N, Y is O or NR3 wherein R3 is H, CH3 or C2H5, R1 and R2 each independently are H, C1-C4 alkyl group, C1-C4 alkoxy group, cyclopentyl or cyclohexyl, or alternatively, R1 and R2 can be fused to produce a substituted or unsubstituted benzene ring; and (c) at least one solvent; wherein the amount of the compound of Structure VI present in the composition is effective to inhibit residue from forming when the composition is coated on a substrate and the coated substrate is subsequently processed to form an image on the substrate, and with the proviso that if the polybenzoxazole precursor polymer solely consists of polybenzoxazole precursor polymers that do not contain a photoactive moiety in the polymer, then (d) at least one photoactive compound is also present in the composition.
    Type: Grant
    Filed: March 22, 2006
    Date of Patent: August 5, 2008
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Donald F. Perry
  • Patent number: 7361444
    Abstract: Disclosed are multilayered resist structures including bilayer and top surface imaging which utilize tuned underlayers functioning as ARCs, planarizing layers, and etch resistant hard masks whose properties such as optical, chemical and physical properties are tailored to give a multilayer resist structure exhibiting high resolution, residue free lithography and methods of preparing these materials.
    Type: Grant
    Filed: February 23, 1999
    Date of Patent: April 22, 2008
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Katherina E. Babich, Douglas Charles LaTulipe, Qinghuang Lin, David R. Medeiros, Wayne Martin Moreau, Karen E. Petrillo, John P. Simons
  • Patent number: 7348122
    Abstract: A photosensitive resin composition comprising: a quinone diazide sulfonic acid ester of a phenol compound represented by formula (I) as defined in the specification; and a polybenzoxazole precursor, and a method for manufacturing a semiconductor device using the same
    Type: Grant
    Filed: August 29, 2006
    Date of Patent: March 25, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kenichiro Sato, Tsukasa Yamanaka
  • Patent number: 7220520
    Abstract: A photosensitive resin composition comprising: (d) at least one polybenzoxazole precursor polymer (e) at least one compound having structure VI V1—Y—V2 VI wherein Y is selected from S, O, NR2, (HOCH)p, and each R1 is selected H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group or a halogen, each R2 is selected from H, SH, CH3, C2H5, and a linear or branched C1–C4 alkyl group containing a thiol group; p is an integer of from 1 to 4, and wherein V1 and V2 are independently selected from the group consisting of wherein, m is independently an integer from 0 to 4 with the proviso that m=0 only when Y= n is an integer from 1 to 5; and each R1 is defined as above; and (f) at least one solvent; wherein the amount of the compound of Structure VI present is an amount effective to inhibit residue from forming when the composition is coated on a substrate and the substrate is subsequently processed to form an image, and with the proviso that if the polybenzoxazole precursor
    Type: Grant
    Filed: June 2, 2006
    Date of Patent: May 22, 2007
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, David B. Powell, N. Jon Metivier, Il'ya Rushkin, Richard Hopla
  • Patent number: 7205085
    Abstract: A radiation sensitive dielectric constant changing composition comprising (A) a decomposable compound, (B) a nondecomposable compound, (C) a radiation sensitive decomposer and (D) a stabilizer. The composition allows its dielectric constant to be changed by a simple method, has a sufficiently large difference between its changed dielectric constant and its original dielectric constant and can provide a dielectric constant pattern and an optical material which are stable regardless of their use conditions.
    Type: Grant
    Filed: July 25, 2002
    Date of Patent: April 17, 2007
    Assignee: JSR Corporation
    Inventors: Isao Nishimura, Nobuo Bessho, Atsushi Kumano, Kenji Yamada
  • Patent number: 7205084
    Abstract: A heat-sensitive lithographic printing plate precursor is disclosed which comprises a hydrophilic support and an oleophilic coating thereon which comprises an infrared light-to-heat converter, an alkali-soluble binder and a polymeric developer accelerator. The polymeric developer accelerator is preferably a phenolic formaldehyde resin comprising at least 70 mol % of meta-cresol as recurring unit or at least 40 mol % of monohydroxy benzene cresol as recurring unit. The PDA may also be a phenolic resin which comprises at least 5 mol % of a recurring monomeric unit having at least one phenolic hydroxyl group and at least one alkali solubilising group. The polymeric developer accelerator improves the sensitivity while maintaining a good under-exposure latitude and a good developer resistance of the printing plate.
    Type: Grant
    Filed: April 29, 2004
    Date of Patent: April 17, 2007
    Assignee: AGFA-Gevaert
    Inventors: Marc Van Damme, Huub Van Aert
  • Patent number: 7198878
    Abstract: The invention is a photoswitchable benzocyclobutene-based polymer that while remaining aqueous developable, avoids the problem of significant moisture uptake. The oligomer or polymer comprises a polymeric backbone, benzocyclobutene reactive groups, and photoswitchable pendant groups. The pendant groups are bonded to the polymeric backbone and are characterized by the presence of a moiety that converts to carboxylic acid upon exposure to activating wavelengths of radiation a carboxylic acid. When the oligomer or polymer is subsequently heated to cause cure of the oligomer or polymer, carbon dioxide is emitted and the group forms a substantially non-polar moiety. The invention is also a method of making such a polymer and a method of forming a patterned film using such a polymer.
    Type: Grant
    Filed: June 7, 2005
    Date of Patent: April 3, 2007
    Assignee: The Dow Chemical Company
    Inventors: Ying Hung So, Scott J. Bis, Keith J. Watson
  • Patent number: 7198877
    Abstract: A heat-sensitive lithographic printing plate precursor is disclosed which comprises a hydrophilic support and an oleophilic coating comprising an infrared absorbing agent and a polymer, which comprises a phenolic monomeric unit wherein the phenyl group of the phenolic monomeric unit is substituted by a group having the structure —N?N-Q wherein the —N?N— group is covalently bound to a carbon atom of the phenyl group and wherein Q is an aromatic group and wherein the substitution increases the chemical resistance of the coating.
    Type: Grant
    Filed: September 29, 2003
    Date of Patent: April 3, 2007
    Assignee: Agfa-Gevaert
    Inventors: Marc Van Damme, Johan Loccufier, Bert Groenendaal, Huub Van Aert
  • Patent number: 7195849
    Abstract: A positive photosensitive resin composition comprising: (a) at least one polybenzoxazole precursor polymer having structure I or II; (b) at least one photosensitive compound selected from compounds described by structures III–V, (c) at least one solvent; and (d) optionally an adhesion promoter.
    Type: Grant
    Filed: March 4, 2004
    Date of Patent: March 27, 2007
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, Pamela J. Waterson, William D. Weber, Ilya Rushkin, Richard Hopla, Jon Metivier
  • Patent number: 7175960
    Abstract: A positive resist composition comprising a mixture of an alkali-soluble novolak resin prepared using m-cresol, p-cresol and 2,5-xylenol as starting reactants and a phenolic compound, wherein the hydrogen atoms of all hydroxyl groups are substituted in a proportion of 0.03–0.05 mol per hydrogen atom with 1,2-naphthoquinonediazidosulfonyl ester groups, has uniformity, high sensitivity and high resolution, and is improved in heat resistance, film retention, substrate adhesion, and storage stability.
    Type: Grant
    Filed: September 9, 2004
    Date of Patent: February 13, 2007
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato
  • Patent number: 7132213
    Abstract: A positive photoresist composition comprising an alkali-soluble novolak resin (A) containing a structural unit (a1) represented by a general formula (I) shown below, and a structural unit (a2) represented by a general formula (II) shown below, and a photosensitizer (B)
    Type: Grant
    Filed: July 15, 2004
    Date of Patent: November 7, 2006
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuo Masuda, Toshiki Okui
  • Patent number: 7101652
    Abstract: New photosensitive PBO precursor polymers which contain diazoquinone moieties attached to its backbone and in which all amino end groups are converted into amide groups. The photosensitive formulation based on the disclosed PBO precursor polymers have good imaging and mechanical properties as well as superior shelf life stability. Photosensitive polybenzoxazole precursor polymers having (sulfon)amide end groups (with or without attached diazoquinone groups) can be formulated into photosensitive compositions with diazoquinone photoactive compounds which lack benzylic hydrogens on the backbone to yield compositions producing films significantly lighter in color after curing.
    Type: Grant
    Filed: March 9, 2004
    Date of Patent: September 5, 2006
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, Ilya Rushkin, Richard Hopla, Donald Racicot
  • Patent number: 7056641
    Abstract: A positive photosensitive resin composition of at least one uncapped polybenzoxazole precursor polymer, at least one capped polybenzoxazole precursor polymer, at least one photosensitive agent and at least one solvent, use of such compositions to pattern an image on a substrate and the resulting relied patterned substrates and electronic parts therefrom.
    Type: Grant
    Filed: July 8, 2005
    Date of Patent: June 6, 2006
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
  • Patent number: 7019093
    Abstract: The invention is a photoswitchable benzocyclobutene-based polymer that while remaining aqueous developable, avoids the problem of significant moisture uptake. The oligomer or polymer comprises a polymeric backbone, benzocyclobutene reactive groups, and photoswitchable pendant groups. The pendant groups are bonded to the polymeric backbone and are characterized by the presence of a moiety that converts to carboxylic acid upon exposure to activating wavelengths of radiation a carboxylic acid. When the oligomer or polymer is subsequently heated to cause cure of the oligomer or polymer, carbon dioxide is emitted and the group forms a substantially non-polar moiety. The invention is also a method of making such a polymer and a method of forming a patterned film using such a polymer.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: March 28, 2006
    Assignee: Dow Global Technologies Inc.
    Inventors: Ying Hung So, Keith J. Watson, Scott J. Bis
  • Patent number: 7005227
    Abstract: In one embodiment, a photoactive compound may be attached to a polymer backbone. This embodiment may be more resistant to the generation of reactive outgassing components and may exhibit better contrast.
    Type: Grant
    Filed: January 21, 2004
    Date of Patent: February 28, 2006
    Assignee: Intel Corporation
    Inventors: Wang Yueh, Heidi Cao
  • Patent number: 6939659
    Abstract: A positive photosensitive resin composition of at least one uncapped polybenzoxazole precursor polymer, at least one capped polybenzoxazole precursor polymer, at least one photosensitive agent and at least one solvent, use of such compositions to pattern an image on a substrate and the resulting relied patterned substrates and electronic parts therefrom.
    Type: Grant
    Filed: March 4, 2004
    Date of Patent: September 6, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Ahmad A. Naiini, William D. Weber, Pamela D. Waterson, Steve Lien-Chung Hsu
  • Patent number: 6911292
    Abstract: A positive resist composition contains a novolak resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl ester groups, a methyl vinyl ether-monoalkyl maleate copolymer and optionally, an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate. The composition is useful as a thick film photoresist which is subject to a plating step and offers many advantages including high sensitivity, perpendicular geometry, high resolution, and crack resistance during and after the plating step.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: June 28, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato
  • Patent number: 6905809
    Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: 1) a film-forming novolak resin wherein the hydrogen atom of a hydroxyl group in the novolak resin is substituted with a naphthoquinonediazidosulfonyl (DNQ) group in a proportion of less than 3.0 mol % per hydrogen atom to form a partially esterified novolak resin; 2) at least one photosensitive component present in an amount sufficient to photosensitive the photoresist composition; and 3) at least one solvent.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: June 14, 2005
    Assignee: Clariant Finance (BVI) Limited
    Inventor: J. Neville Eilbeck
  • Patent number: 6869742
    Abstract: A positive photoresist composition includes (A) an alkali-soluble novolak resin containing 1,2-naphthoquinonediazidosulfonyl groups substituting for part of hydrogen atoms of phenolic hydroxyl groups, (B) an ester of, for example, a compound represented by the following formula with a naphthoquinonediazidosulfonyl compound, and (C) a sensitizer:
    Type: Grant
    Filed: April 1, 2002
    Date of Patent: March 22, 2005
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jyunichi Mizuta, Kouji Yonemura, Akira Katano, Satoshi Niikura, Kousuke Doi
  • Patent number: 6858359
    Abstract: Multi-layer, positive working, thermally sensitive imageable elements, useful as lithographic printing plate precursors, are disclosed. The elements comprises a substrate, an underlayer over the substrate, and a top layer over the underlayer. The top layer comprises polymeric material, which is a solvent soluble novolac resin or a derivative thereof. The polymeric material is a (a) novolac that has a weight average molecular weight of at least 10,000, a derivative thereof functionalized with polar groups, or a derivative thereof functionalized with quadruple hydrogen bonding entities; (b) a solvent soluble m-cresol/p-cresol novolac resins that comprises at least 10 mol % p-cresol and has a weight average molecular weight of at least 8,000, a derivative thereof functionalized with polar groups, or a derivative thereof functionalized with quadruple hydrogen bonding entities; or (c) a mixture thereof. The imageable elements have increased scuff resistance and are thus less susceptible to damage during handling.
    Type: Grant
    Filed: October 4, 2002
    Date of Patent: February 22, 2005
    Assignee: Kodak Polychrome Graphics, LLP
    Inventors: Anthony P. Kitson, Kevin B. Ray, Eugene L. Sheriff
  • Patent number: 6849372
    Abstract: The present invention provides methods of forming and using thermally imageable composite elements which may be developed into lithographic printing plates. More specifically, the present invention provides a method of forming thermally imageable composite elements which provide substantial developer resistance in desired regions, while maintaining white light desensitivity and durability.
    Type: Grant
    Filed: July 30, 2002
    Date of Patent: February 1, 2005
    Assignee: Kodak Polychrome Graphics
    Inventors: Kevin Ray, Anthony Paul Kitson, Jian Bing Huang
  • Patent number: 6846616
    Abstract: A process for the production of a pattern-forming body, the process including the steps of disposing a catalyst-containing layer-side substrate containing at least a photo catalyst-containing layer and a pattern-forming body substrate containing a characteristic-changeable layer which is changed in characteristics by the action of the photocatalyst in at least said photocatalyst-containing layer such that the photocatalyst-containing layer is in contact with the characteristic-changeable layer followed by performing exposure to thereby change the characteristics of the exposed portion of the characteristic-changeable layer and thereafter dismounting the photocatalyst-containing layer-side substrate, thereby obtaining a pattern-forming body having a pattern which has been changed in characteristics on the characteristic-changeable layer.
    Type: Grant
    Filed: September 12, 2001
    Date of Patent: January 25, 2005
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Hironori Kobayashi, Masato Okabe, Manabu Yamamoto
  • Patent number: 6838223
    Abstract: A composition for an anti-reflective layer capable of simultaneously being developed together with a photoresist layer after exposure of the photoresist layer in a photolithography process and a method for forming patterns in a semiconductor device using the composition, wherein the anti-reflective light absorbing layer composition includes a polymer having a (meth)acrylate repeating unit, a light-absorbing group of diazoquinones chemically bound to the (meth)acrylate repeating unit, a photoacid generator, a cross-linker which thermally cross-links the polymer and is decomposed from the polymer by an acid, and a catalyst for the cross-linking reaction of the polymer. The method for forming patterns in a semiconductor device involves forming an anti-reflective layer on a semiconductor substrate using the composition and simultaneously exposing the anti-reflective layer and a photoresist layer, thereby chemically transforming the anti-reflective layer so it is able to be developed.
    Type: Grant
    Filed: February 12, 2003
    Date of Patent: January 4, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-woong Yoon, Hoe-sik Chung, Jin-a Ryu, Young-ho Kim
  • Patent number: 6824947
    Abstract: Photosensitive compositions comprising a phenol resin having a urea bond in the main chain, planographic printing plate precursors containing the photosensitive compositions, and methods for preparing planographic printing plates using the planographic printing plate precursors are disclosed. Planographic printing plates that exhibit good durability, good exposure visual image property, and good solvent resistance; particularly superior resistance to washing oil used in UV ink printing; and superior baking property are produced.
    Type: Grant
    Filed: February 19, 2003
    Date of Patent: November 30, 2004
    Assignee: Kodak Polychrome Graphics, LLC
    Inventors: Yasuhiro Ishizuka, Yasuhiko Kojima
  • Patent number: 6803167
    Abstract: Processes for imaging and developing imageable elements useful as lithographic printing plate precursors either thermally or with ultraviolet radiation that use the same developer are disclosed. The imageable elements comprise a top layer and an underlayer. The top layer contains a phenolic polymer and a material that has either the o-benzoquinonediazide functionality or the o-diazonaphthoquinone functionality. The developer is a 20:80 to 80:20 mixture of (1) an aqueous alkaline developer that has a pH greater than 11 and contains about 2 wt % to about 8 wt % of an alkali metal silicate, and (2) a solvent based developer that contains about 0.5 wt % to about 15 wt % of an organic solvent or mixture of organic solvents.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: October 12, 2004
    Assignee: Kodak Polychrome Graphics, LLC
    Inventors: Jayanti Patel, Kevin B. Ray, Jianbing Huang
  • Publication number: 20040197696
    Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: 1) a film-forming novolak resin wherein the hydrogen atom of a hydroxyl group in the novolak resin is substituted with a naphthoquinonediazidosulfonyl (DNQ) group in a proportion of less than 3.0 mol % per hydrogen atom to form a partially esterified novolak resin; 2) at least one photosensitive component present in an amount sufficient to photosensitize the photoresist composition; and 3) at least one solvent.
    Type: Application
    Filed: April 1, 2003
    Publication date: October 7, 2004
    Inventor: J. Neville Eilbeck
  • Patent number: 6790582
    Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: a) a novolak resin partially esterified with from about 3 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; and c) at least one solvent.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: September 14, 2004
    Assignee: Clariant Finance BVI Limited
    Inventor: J. Neville Eilbeck
  • Patent number: RE41083
    Abstract: A radiation-sensitive composition for use in printing plates is described. The composition comprises: (a) at least one novolak; (b) at least one naphthoquinone diazide derivative; and (c) a copolymer comprising units A, B, and a unit C comprising a cyclic terminal urea group, wherein unit A is present in an amount of about 5 to about 50 mol % and has the formula is represented by wherein R1 is selected such that the homopolymer of A is alkali-soluble, unit B is present in an amount of about 20 to about 70 mol % and has the following formula is represented by wherein R2 is selected such that the homopolymer of B has a glass transition temperature greater than 100° C., preferably a glass transition temperature in the range from about 100 to about 380° C.
    Type: Grant
    Filed: July 26, 2005
    Date of Patent: January 19, 2010
    Assignee: Eastman Kodak Company
    Inventor: Mathias Jarek