Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 6632586
    Abstract: A positive resist composition which comprises (A) a compound which generates an acid upon irradiation with an actinic ray or radiation, and (B) a resin which is decomposed by the action of an acid to increase solubility in an alkaline developing solution and contains repeating units represented by formulae (I) and (V):
    Type: Grant
    Filed: September 9, 1999
    Date of Patent: October 14, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Kenichiro Sato
  • Publication number: 20030190554
    Abstract: A plate-making method of a printing plate comprising exposing a printing plate precursor having a photosensitive layer comprising a photopolymerizable composition containing (i) a crosslinking agent having two ethylenic polymerizable groups and (ii) a crosslinking agent having three or more ethylenic polymerizable groups, and development processing the exposed printing plate precursor with an alkali developer having a pH of not more than 12.5.
    Type: Application
    Filed: August 29, 2002
    Publication date: October 9, 2003
    Inventor: Kazuto Kunita
  • Publication number: 20030186161
    Abstract: A positive photosensitive composition comprising (A) an acid generator that generates an acid upon irradiation of an actinic ray or radiation, (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution, and (C) a specific basic compound.
    Type: Application
    Filed: July 3, 2002
    Publication date: October 2, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventor: Toru Fujimori
  • Patent number: 6627379
    Abstract: Photoresist compositions which are useful in a resist flow process are disclosed. A process for forming a contact hole pattern using the disclosed photoresist compositions is also disclosed. The disclosed photoresist resin includes a mixture of two or more polymers. Preferably, a mixture of a first copolymer and a second copolymer are cross-linked, and thus it prevents a contact hole from being collapsed due to over flow which is typically observed during a conventional resist flow process. In addition, the disclosed photoresist compositions allow formation of uniform sized patterns.
    Type: Grant
    Filed: April 18, 2001
    Date of Patent: September 30, 2003
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jin Soo Kim, Jae Chang Jung, Geun Su Lee, Ki Ho Baik
  • Publication number: 20030180662
    Abstract: The photoresist resin composition comprises a polymer containing an acid-responsive compound unit of the following formula (e.g. an adamantane skeleton) and a photoactive acid precursor. R1 may be an alkyl group having a tertiary carbon atom in the 1-position and the Z ring is a bridged-ring hydrocarbon ring comprising 2 to 4 rings.
    Type: Application
    Filed: March 13, 2003
    Publication date: September 25, 2003
    Applicant: Daicel Chemical Industries, Ltd.
    Inventor: Tatsuya Nakano
  • Publication number: 20030180665
    Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.
    Type: Application
    Filed: March 21, 2003
    Publication date: September 25, 2003
    Inventor: Ying Wang
  • Publication number: 20030180661
    Abstract: A polymer having a repeating unit comprising a copolymer of butadiene sulfone and maleic anhydride, and a chemically amplified resist composition comprising the polymer.
    Type: Application
    Filed: March 11, 2003
    Publication date: September 25, 2003
    Inventors: Sang-jun Choi, Woo-sung Han, Sang-gyun Woo
  • Patent number: 6623907
    Abstract: A positive-tone radiation-sensitive resin composition comprising: (A) a low molecular weight compound having at least one amino group in which the nitrogen atom has at least one hydrogen atom bonded thereto and at least one of the hydrogen atoms is replaced by a t-butoxycarbonyl group, (B) a photoacid generator, and (C-1) a resin insoluble or scarcely soluble in alkali which is protected by an acid-dissociable group and becomes soluble in alkali when the acid-dissociable group dissociates or (C-2) an alkali-soluble resin and an alkali solubility control agent is disclosed. Also disclosed is a negative-tone radiation-sensitive resin composition comprising the low molecular weight compound (A), the photoacid generator (B), an alkali-soluble resin (D), and a compound capable of crosslinking with the alkali-soluble resin in the presence of an acid(E).
    Type: Grant
    Filed: February 1, 2001
    Date of Patent: September 23, 2003
    Assignee: JSR Corporation
    Inventors: Jun Numata, Aki Suzuki, Hiromichi Hara, Norihiro Natsume, Kiyoshi Murata, Masafumi Yamamoto, Akimasa Soyano, Toru Kajita, Tsutomu Shimokawa
  • Patent number: 6617086
    Abstract: A new group of non-chemically amplified negative tone water/aqueous base developable (photo) resists based on redistribution of carbon-oxygen bonds in pendant ester groups of the polymers has been found.
    Type: Grant
    Filed: March 2, 2001
    Date of Patent: September 9, 2003
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Edward D. Babich, Inna V. Babich, Katherina E. Babich, James J. Bucchignano, Karen E. Petrillo, Steven A. Rishton
  • Publication number: 20030165776
    Abstract: A negative resist composition comprising (A) an alkali-soluble polymer, (B) a cross-linking agent forming cross-links between molecules of the alkali-soluble polymer (A) under the action of an acid and (C) a specified acid generator, which can satisfy all of performance requirements concerning sensitivity, resolution, pattern profile and line-edge roughness in the pattern formation by irradiation with electron beams or X-rays.
    Type: Application
    Filed: December 30, 2002
    Publication date: September 4, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Shoichiro Yasunami, Kunihiko Kodama
  • Patent number: 6613844
    Abstract: A chemically amplified positive resist composition comprising a styrene polymer represented by formula (1), terminated with P, and having a weight average molecular wherein R is OH or OR3, R1 is H or CH3, R2 is alkyl, R3 is acid labile group, x≧0, y>0, k≧0, m≧0, n>0, 0<q≦0.8, p+q=1, P is H, alkyl, alkenyl, aromatic, carboxyl, OH, —R4(COR5)r, —R4O(OH)r or —R4 (OR5)r. A chemically amplified positive resist composition comprising the polymer as a base resin has high sensitivity and resolution and forms resist patterns having plasma etching resistance, heat resistance, and reproducibility.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: September 2, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Osamu Watanabe, Shimada Junji, Nagura Shigehiro, Takeda Takanobu
  • Publication number: 20030162128
    Abstract: A photosensitive thick film composition. The photosensitive thick film composition can produce electrode material with high resolution and high contrast. The photosensitive thick film composition includes an acrylic copolymer, a photoinitiator, a reactive monomer, a conductive metal, glass powder, an additive, and an organic solvent.
    Type: Application
    Filed: December 4, 2002
    Publication date: August 28, 2003
    Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
    Inventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
  • Publication number: 20030157434
    Abstract: A positive planographic printing plate precursor includes a support having disposed thereon a lower thermosensitive layer containing a water-insoluble but alkali-soluble polymer compound and an upper thermosensitive layer containing a water-insoluble but alkali-soluble polymer compound, with alkali-solubility increasing under heat, wherein (i) both the upper thermosensitive layer and the lower thermosensitive layer contain an IR absorbing dye, with the ratio of the IR absorbing dye concentration in the upper thermosensitive layer to the IR absorbing dye concentration in the lower thermosensitive layer is 1.6 to 10.0, and/or (ii) the upper thermosensitive layer and the lower thermosensitive layer contain different IR absorbing dyes, and/or (iii) at least one of the upper thermosensitive layer and the lower thermosensitive layer contains an IR absorbent having, in one molecule, at least two chromophoric groups that absorb IR light, with the chromophoric groups bonding to each other via a covalent bond.
    Type: Application
    Filed: June 26, 2002
    Publication date: August 21, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Akio Oda, Hideo Miyake, Tomoyoshi Mitsumoto, Takeshi Serikawa, Ikuo Kawauchi, Ippei Nakamura
  • Publication number: 20030148211
    Abstract: The present invention provides a sulfonium salt represented by the following formula (I): 1
    Type: Application
    Filed: November 27, 2002
    Publication date: August 7, 2003
    Inventors: Akira Kamabuchi, Kaoru Araki
  • Publication number: 20030148213
    Abstract: The following resist composition which is excellent particularly in transparency to light beams and dry etching properties and gives a resist pattern excellent in sensitivity, resolution, evenness, heat resistance, etc., as a chemical amplification type resist, is presented.
    Type: Application
    Filed: December 19, 2002
    Publication date: August 7, 2003
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Isamu Kaneko, Yoko Takebe, Shun-Ichi Kodama
  • Patent number: 6602650
    Abstract: A compound of Formula 10, an organic anti-reflective polymer having the structure of Formula 1 synthesized from the compound of Formula 1 and a preparation method thereof. An anti-reflective coating composition including the above organic anti-reflective polymer, as well as a preparation method of an anti-reflective coating. The anti-reflective coating comprising the disclosed polymer eliminates standing waves caused by the optical properties of lower layers on the wafer and by the changes in the thickness of the photoresist, prevents back reflection and also solves the problem of CD alteration cause by the diffracted and reflected light from such lower layers. Such advantages enable the formation of stable ultrafine patterns suitable for 64M, 256M, 1G, 4G, and 16G DRAM semiconductor devices and an increase of the production yields.
    Type: Grant
    Filed: March 13, 2002
    Date of Patent: August 5, 2003
    Assignee: Hynix Semiconductor Inc
    Inventors: Sung-eun Hong, Min-ho Jung, Jae-chang Jung, Geun-su Lee, Ki-ho Baik
  • Patent number: 6599678
    Abstract: An organic anti-reflective polymer having the following Formula 1, its preparation method, an anti-reflective coating composition comprising the said organic anti-reflective polymer and a preparation method of an anti-reflective coating made therefrom. The anti-reflective coating comprising the disclosed polymer eliminates standing waves caused by the optical properties of lower layers on the wafer and by the thickness changes of the photoresist, prevents back reflection and CD alteration caused by the diffracted and reflected light from such lower layers. Such advantages enable the formation of stable ultrafine patterns suitable for 64M, 256M, 1G, 4G, and 16G DRAM semiconductor devices and improve the production yields. Further, it is also possible to control the k value and the increased hydrophobicity facilitates EBR (Edge Bead Removal).
    Type: Grant
    Filed: June 25, 2001
    Date of Patent: July 29, 2003
    Assignee: Hynix Semiconductor Inc
    Inventors: Sung-eun Hong, Min-ho Jung, Jae-chang Jung, Geun-su Lee, Ki-ho Baik
  • Patent number: 6596458
    Abstract: Disclosed is a positive-working photoresist composition having reduced development defects, and excellent in resist pattern profiles and in the resolving power of contact holes, which comprises (i) a compound generating an acid by irradiation of active light or radiation, and (ii) a resin containing repeating units of at least one kind selected from the group consisting of (a) repeating units having alkali-soluble groups each protected with at least one group selected from the group consisting of groups containing alicyclic hydrocarbon structures represented by specific general formulas (pI) to (pVI), (b) repeating units represented by specific general formula (II) and (c) repeating units represented by specific general formulas (III-a) to (III-d), and decomposed by the action of an acid to increase the solubility of the resin into an alkali.
    Type: Grant
    Filed: May 3, 2000
    Date of Patent: July 22, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Kunihiko Kodama, Toshiaki Aoai, Yasumasa Kawabe
  • Patent number: 6596460
    Abstract: A copolymer useful in radiation sensitive compositions for lithographic printing plates comprises the units A, B, C and D, wherein A is present in an amount of 0.5 to 30 wt.-% and is of the formula wherein R is hydrogen, C1-C4 alkyl, —CH═COOH or B is present in an amount of 5 to 35 wt.-% and is of the formula C is present in an amount of 10 to 55 wt.
    Type: Grant
    Filed: December 29, 2000
    Date of Patent: July 22, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Hans-Joachim Timpe, Ursula Müller
  • Patent number: 6589707
    Abstract: The present invention provides photoresist monomers, photoresist polymers derived from the same, processes for producing such photoresist polymers, photoresist compositions comprising such polymers, and processes for producing a photoresist pattern using such photoresist compositions. In particular, photoresist monomers of the present invention comprise a moiety of Formula 4: where R1, R2, R3 and R4 are those defined herein. Photoresist polymers of the present invention have a relatively high etching resistance, and therefore are useful in a thin resist process and a bilayer photoresist process. Moreover, photoresist polymers of the present invention have a high contrast ratio between an exposed region and a non-exposed region.
    Type: Grant
    Filed: February 15, 2001
    Date of Patent: July 8, 2003
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6586152
    Abstract: The present invention relates to an agent for reducing substrate dependence useful as an ingredient of a resist composition used for preparation of semiconductor devices and the like, which comprises a compound shown by the following general formula [1]: wherein R41 is a hydrogen atom or a methyl group, R42 is a hydrogen atom, a methyl group, an ethyl group or a phenyl group, R43 is a straight chained, branched or cyclic alkyl group having 1 to 6 carbon atoms, and n is 0 or 1.
    Type: Grant
    Filed: June 12, 2000
    Date of Patent: July 1, 2003
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Naoki Katano, Tomoko Kiryu
  • Publication number: 20030118942
    Abstract: A lithographic printing plate for infrared laser is provided which shows an excellent coated surface state and an excellent stability with time against scratch, and which has a heat-sensitive layer containing the following (A) to (D):
    Type: Application
    Filed: August 14, 2002
    Publication date: June 26, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Tomoyoshi Mitsumoto, Noriaki Watanabe, Kazuo Maemoto
  • Publication number: 20030118939
    Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.
    Type: Application
    Filed: November 9, 2001
    Publication date: June 26, 2003
    Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.
    Inventors: Heidi Munnelly, Paul West
  • Patent number: 6582882
    Abstract: The present invention includes an imageable element, comprising a substrate and a thermally imageable composition which includes a graft copolymer having hydrophobic and hydrophilic segments. Upon imagewise exposure to thermal energy, the graft copolymer produces exposed regions that are less soluble in a developer than the unexposed regions. Also included is a method of producing an imaged element which includes a graft copolymer according to the present invention.
    Type: Grant
    Filed: April 4, 2001
    Date of Patent: June 24, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: S. Peter Pappas, Shashikant Saraiya
  • Patent number: 6582880
    Abstract: An acrylate resin containing fluorinated alkyl groups in ester side chains has high transmittance to VUV radiation. A resist composition using the resin as a base polymer is sensitive to high-energy radiation, has excellent sensitivity and resolution, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: September 7, 2001
    Date of Patent: June 24, 2003
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co. Ltd., Central Glass Co., Ltd.
    Inventors: Yuji Harada, Jun Watanabe, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Publication number: 20030111771
    Abstract: Methods and materials used to make detailed cast objects are disclosed. The cast objects are formed in mold created from a photosensitive laminate. The mold is formed by selectively removing portions of the photosensitive laminate. The invention is particularly well suited to make thin molded articles, but can also be used to make thicker molded articles by using multiple photosensitive layers or laminates.
    Type: Application
    Filed: December 13, 2001
    Publication date: June 19, 2003
    Inventors: Alexander Sergeievich Gybin, Toshifumi Komatsu
  • Patent number: 6579659
    Abstract: A chemical amplification type positive resist composition excellent in balance of properties such as resolution, profile, sensitivity, dry etching resistance, adhesion and the like which comprises a resin which has the following polymeric units (A), (B) and (C); and an acid generating agent.
    Type: Grant
    Filed: April 3, 2001
    Date of Patent: June 17, 2003
    Inventors: Yasunori Uetani, Airi Yamada, Yoshiko Miya, Yoshiyuki Takata
  • Publication number: 20030108814
    Abstract: A lithographic printing plate precursor comprising a hydrophilic support, an alkali-soluble layer and provided on the alkali-soluble layer a recording layer which contains an infrared ray absorbent, an alkali-soluble resin and an inhibitor of inhibiting the alkali-soluble resin from dissolving in an alkali aqueous developer and increases in the solubility in an alkaline aqueous solution upon irradiation of infrared light, and a developing method of the lithographic printing plate precursor with a non-silicate developer.
    Type: Application
    Filed: June 19, 2002
    Publication date: June 12, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Hideo Miyake, Akio Oda, Tomoyoshi Mitsumoto
  • Patent number: 6576392
    Abstract: A positive photoresist composition comprising a photo-acid gererator and a specific resin. The resin contains repeating units each having a group represented by formula (I): —SO2—O—R wherein R represents an optionally substituted alkyl, cycloalkyl, or alkenyl group and comes to have an increased rate of dissolution in an alkaline developing solution by the action of an acid, or contains alkali-soluble groups protected by partial structures containing an alicyclic hydrocarbon and represented by at least one of formulae (pI) to (pVI) defined in the specification and which decomposes by the action of an acid to have enhanced solubility in an alkali. The latter is used in combination with a compound which decomposes by the action of an acid to generate a sulfonic acid.
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: June 10, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Kunihiko Kodama, Toshiaki Aoai, Hidekazu Ohashi
  • Patent number: 6576398
    Abstract: In the pattern formation method of this invention, a resist film is formed by applying, on a substrate, a pattern formation material containing a polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2, and an acid generator, wherein R1 and R2 are the same or different and selected from the group consisting of an alkyl group, a chlorine atom and an alkyl group including a chlorine atom; and R3 is a protecting group released by an acid. Then, the resist film is irradiated with exposing light of a wavelength of a 1 nm through 30 nm band or a 110 nm through 180 nm band for pattern exposure, and a resist pattern is formed by developing the resist film after the pattern exposure.
    Type: Grant
    Filed: March 6, 2001
    Date of Patent: June 10, 2003
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masaru Sasago, Masamitsu Shirai, Masahiro Tsunooka
  • Patent number: 6576400
    Abstract: The present invention relates to a positive-working radiation-sensitive composition which is characterized in that it is a positive-working radiation-sensitive composition containing polymer the solubility of which is increased in aqueous alkali by the action of acid, and a compound which generates acid by irradiation with radiation, and the ease of occurrence of main chain scission of said polymer by means of radiation is greater than that of polymethyl methacrylate, and it also relates to a positive-working radiation-sensitive composition which is characterized in that it contains an alkali-soluble polymer, a compound having the effect of suppressing the alkali-solubility of said alkali-soluble polymer and the suppression effect of which is lowered or eliminated by the action of acid, and a compound which generates acid by irradiation with radiation, and the ease of occurrence of main chain scission of said alkali-soluble polymer by radiation is greater than that of polymethyl methacrylate.
    Type: Grant
    Filed: May 10, 2000
    Date of Patent: June 10, 2003
    Assignee: Toray Industries, Inc.
    Inventor: Kazutaka Tamura
  • Publication number: 20030104314
    Abstract: An imaging member, such as a negative-working printing plate or on-press cylinder, can be prepared with a hydrophilic imaging layer comprised of a heat-sensitive hydrophilic charged polymer (ionomer) and an infrared radiation sensitive negatively-charged oxonol dye that has a &lgr;max of greater than 700 nm. The heat-sensitive polymer and IR dye can be formulated in water or water-miscible solvents to provide highly thermal sensitive imaging compositions. In the imaging member, the polymer reacts to provide increased hydrophobicity in areas exposed to energy that provides or generates heat. For example, heat can be supplied by laser irradiation in the IR region of the electromagnetic spectrum. The heat-sensitive polymer is considered “switchable” in response to heat, and provides a lithographic image without conventional alkaline processing.
    Type: Application
    Filed: September 5, 2001
    Publication date: June 5, 2003
    Applicant: Eastman Kodak Company
    Inventors: Shiying Zheng, Kevin W. Williams
  • Publication number: 20030099897
    Abstract: The present invention describes encapsulated inorganic resists which are compatible with conventional resist processing and development. The encapsulated inorganic materials increase the plasma etch selectivity of the resists compared to conventional polymeric resists. In effect, these resist systems can act as photoimagable single layer hard mask. In a preferred embodiment, the encapsulated material includes inorganic core particles that are at least partially coated with a moiety having an acid labile or photo-labile protected acidic group such that, upon deprotection, the encapsulated material exhibits greater base solubility.
    Type: Application
    Filed: February 25, 2002
    Publication date: May 29, 2003
    Applicant: MASS INSTITUTE OF TECHNOLOGY (MIT)
    Inventor: Theodore H. Fedynyshyn
  • Publication number: 20030099900
    Abstract: A chemical amplification type positive resist composition, which can reduce cost steeply without significantly decreasing basic abilities, is provided, and the chemical amplification type positive resist composition comprises (A) a resin having a polymerization unit derived from p-hydroxystyrene and a polymerization unit of the formula (1) or formula (2) 1
    Type: Application
    Filed: September 26, 2002
    Publication date: May 29, 2003
    Inventors: Airi Yamada, Masumi Suetsugu, Yasunori Uetani
  • Patent number: 6569599
    Abstract: The present invention provides photoresist polymers, processes for producing the same, photoresist compositions comprising such polymers, and processes for producing a photoresist pattern using such photoresist compositions. In particular, photoresist polymers of the present invention comprise a moiety of the Formula: where R1, R2, R3 and R4 are those defined herein. Photoresist polymers of the present invention have a relatively high etching resistance, and therefore are useful in thin resist processes and bilayer photoresist processes. Moreover, photoresist polymers of the present invention have a high contrast ratio between the exposed region and the non-exposed region.
    Type: Grant
    Filed: May 10, 2001
    Date of Patent: May 27, 2003
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6569602
    Abstract: This invention discloses compositions that can be polymerized/crosslinked imagewise upon exposure to ionization radiation such as x-ray, electron beam, ion beam, and gamma-ray. This invention also discloses methods of use for these compositions for microfabrication of ceramics, for stereolithography, and for x-ray, e-beam, and ion-beam lithography which can be used for photoresists.
    Type: Grant
    Filed: May 18, 1999
    Date of Patent: May 27, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Ying Wang
  • Patent number: 6566037
    Abstract: A polymer comprising recurring units of formula (1) and having a Mw of 1,000-500,000 is provided. R1 is H, methyl or CH2CO2R3, R2 is H, methyl or CO2R3, R3 is alkyl, R4 is H, alkyl, alkoxyalkyl or acyl, R5 and R15 are acid labile groups, and at least one of R6 to R9 is a carboxyl or hydroxyl-containing monovalent hydrocarbon group, and the reminders are H or alkyl, at least one of R10 to R13 is a monovalent hydrocarbon group containing a —CO2— partial structure, and the reminders are H or alkyl, R14 is a polycyclic hydrocarbon group or polycyclic hydrocarbon-containing alkyl group, Z is a trivalent hydrocarbon group, k=0 or 1, x is>0, a, b, c and d are≧0, satisfying x+a+b+c+d=1. A resist composition comprising the polymer has significantly improved sensitivity, resolution and etching resistance and is very useful in microfabrication.
    Type: Grant
    Filed: March 5, 2001
    Date of Patent: May 20, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Jun Hatakeyama
  • Patent number: 6566038
    Abstract: A polymer comprising units of formulas (1) and (2) and having a Mw of 1,000-500,000 is provided. R1 is H, CH3 or CH2CO2R3, R2 is H, CH3 or CO2R3, R3 is alkyl, R4 is halogen or acyloxy, alkoxycarbonyloxy or alkylsulfonyloxy group which may be substituted with halogen, R5 is H or alkyl, R6 is an acid labile group, Z is a single bond or a divalent hydrocarbon group, k is 0 or 1, and W is —O— or —(NR)— wherein R is H or alkyl. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation, has excellent sensitivity, resolution, and etching resistance, and lends itself to micropatterning with electron beams or deep-UV rays.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: May 20, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Takeshi Kinsho, Koji Hasegawa, Takeru Watanabe, Jun Hatakeyama
  • Publication number: 20030091927
    Abstract: Photoresist monomers, polymers thereof, photoresist compositions containing the same for preventing acid generated in the exposed area during the course of a photolithography process from being diffused to the unexposed area. The line edge roughness and slope pattern are improved when an ultrafine photoresist pattern is formed using photoresist copolymer having a multi-oxygen-containing compound as a repeating unit such as an ethyleneoxy moiety represented by Formula 1 with at least one polymerizable carbon-carbon double bond. In addition, the shape of pattern is improved by eliminating top loss and the adhesion of pattern to the substrate is improved.
    Type: Application
    Filed: August 22, 2002
    Publication date: May 15, 2003
    Applicant: HYNIX SEMICONDUCTOR INC.
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin, Se Jin Choi, Deog Bae Kim, Jae Hyun Kim
  • Publication number: 20030091926
    Abstract: A dry film photoresist having a glass transition temperature (Tg) above room temperature. The dry film photoresist is tack free. An artwork may be placed directly on the photoresist without concern that the artwork may stick to the dry film photoresist or become contaminated with photoresist. The dry film photoresist may be laminated on a support sheet and wound into a roll without concern that the photoresist will stick to the backside of the support sheet. The dry film photoresist also has reduced cold flow problems.
    Type: Application
    Filed: December 11, 2002
    Publication date: May 15, 2003
    Applicant: Shipley Company, L.L.C.
    Inventor: James G. Shelnut
  • Publication number: 20030087183
    Abstract: A polymer comprising recurring units of formula (1) wherein R1 is H or methyl, R2 is H or C1-8 alkyl, R3 is CO2R4, and R4 is C1-15 alkyl and recurring units having a carboxylic acid protected with an acid-decomposable protecting group containing an adamantane structure or tetracyclo-[4.4.0.12,5.17,10]dodecane structure and having a Mw of 1,000-500,000 is novel. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation, has excellent sensitivity, resolution and etching resistance and lends itself to micropatterning with electron beams or deep-UV.
    Type: Application
    Filed: August 29, 2002
    Publication date: May 8, 2003
    Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeshi Kinsho
  • Publication number: 20030087180
    Abstract: The present invention relates to a photoresist composition sensitive to radiation in the deep ultraviolet, particularly a positive working photoresist sensitive in the range of 100-200 nanometers(nm). The photoresist composition comprises a) a polymer that is insoluble in an aqueous alkaline solution and comprises at least one acid labile group, and furthermore where the polymer is essentially non-phenolic, b) a compound capable of producing an acid upon radiation, and c) an additive that reduces the effect of electrons and ions on the photoresist image.
    Type: Application
    Filed: November 7, 2001
    Publication date: May 8, 2003
    Inventors: Takanori Kudo, Ralph R. Dammel, Munirathna Padmanaban
  • Publication number: 20030082479
    Abstract: A copolymer of an acrylic monomer having at least one C6-20 alicyclic structure with a norbornene derivative or styrene monomer having a hexafluoroalcohol pendant is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.
    Type: Application
    Filed: June 25, 2002
    Publication date: May 1, 2003
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Michitaka Ootani, Satoru Miyazawa, Kentaro Tsutsumi, Kazuhiko Maeda
  • Patent number: 6555289
    Abstract: Provided is a positive photoresist composition for use in the production of a semiconductor device, which ensures high resolution, reduced edge roughness of a line pattern and a small number of development defects. The positive photoresist composition comprises a resin having a specific silicon-containing group on the side chain, the solubility of which resin in an alkali developer increases under the action of an acid.
    Type: Grant
    Filed: April 6, 2001
    Date of Patent: April 29, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tomoya Sasaki, Kazuyoshi Mizutani, Shoichiro Yasunami
  • Publication number: 20030077540
    Abstract: A positive photosensitive composition comprising (A) a specific acid generator that generates an acid upon irradiation of an actinic ray or radiation, and (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution.
    Type: Application
    Filed: May 21, 2002
    Publication date: April 24, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
  • Patent number: 6551756
    Abstract: The present invention relates to solvent-developable printing formulations useful for the manufacture of printing plates. In particular, the present invention provides formulations which exhibit markedly improved processing characteristics when deposited on a printing plate, such as reduced tack, increased image resolution, and/or improved mechanical properties, e.g., tensile strength, elongation. In accordance with another aspect of the invention, there are provided methods for the preparation of said formulations and methods for use thereof.
    Type: Grant
    Filed: July 24, 2000
    Date of Patent: April 22, 2003
    Assignee: Napp Systems, Inc.
    Inventors: Yuxin Hu, Nathan J. Jacobsen
  • Patent number: 6551763
    Abstract: A composition used as a resist in the manufacture of electronic parts, for example printed circuits, and which is rendered soluble in a developer by pattemwise delivery of heat, comprises a polymer and optionally an infrared absorbing compound. However in contrast to conventional compositions no compound is present which alters the solubility of the polymer in an aqueous developer.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: April 22, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Anthony Paul Kitson, Peter Andrew Reath Bennett, Christopher David McCullough, Stuart Bayes, Kevin Barry Ray
  • Patent number: 6548219
    Abstract: Copolymers prepared by radical polymerization of a substituted norbornene monomer and a fluoromethacrylic acid, fluoromethacrylonitrile, or fluoromethacrylate comonomer are provided. The polymers are useful in lithographic phtoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, i.e., radiation of a wavelength less than 250 nm, including 157 nm, 193 nm and 248 nm radiation, and are thus useful in DUV lithographic photoresist compositions. A process for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: April 15, 2003
    Assignee: International Business Machines Corporation
    Inventors: Hiroshi Ito, Phillip Joe Brock, Gregory Michael Wallraff
  • Publication number: 20030068573
    Abstract: A chemical amplification type positive resist composition is provided which gives resist patterns showing remarkably improved line edge roughness and comprises an acid generator containing a benzenesulfonate ion of the formula (I): 1
    Type: Application
    Filed: July 31, 2002
    Publication date: April 10, 2003
    Inventors: Yoshiyuki Takata, Hiroaki Fujishima, Yasunori Uetani
  • Patent number: RE38256
    Abstract: Disclosed are a safe slurry photosensitive composition superior in image formation capabilities such as resolution and sensitivity and containing no harmful compound, and a safe water-soluble photosensitive composition capable of being dissolved in water without using any organic solvent while maintaining a sufficient sensitivity as a resist and containing no harmful substance. The slurry photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, at least one type of a resin with acid-crosslinkability or acid-decomposability, and a powder. Various devices can be manufactured by forming a layer of this photosensitive composition on a substrate, exposing the layer to light in accordance with a desired pattern, and heating the layer. The water-soluble photosensitive composition contains a compound which generates an acid when irradiated with light or ionizing radiation, and an acetal resin.
    Type: Grant
    Filed: November 24, 1999
    Date of Patent: September 23, 2003
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Naomi Shida, Takuya Naito, Koji Asakawa, Akinori Hongu, Makoto Nakase, Hirokazu Niki