Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
-
Patent number: 6632586Abstract: 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: GrantFiled: September 9, 1999Date of Patent: October 14, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kenichiro Sato
-
Publication number: 20030190554Abstract: 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: ApplicationFiled: August 29, 2002Publication date: October 9, 2003Inventor: Kazuto Kunita
-
Publication number: 20030186161Abstract: 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: ApplicationFiled: July 3, 2002Publication date: October 2, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventor: Toru Fujimori
-
Photoresist composition for resist flow process, and process for forming contact hole using the same
Patent number: 6627379Abstract: 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: GrantFiled: April 18, 2001Date of Patent: September 30, 2003Assignee: Hynix Semiconductor Inc.Inventors: Jin Soo Kim, Jae Chang Jung, Geun Su Lee, Ki Ho Baik -
Publication number: 20030180662Abstract: 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: ApplicationFiled: March 13, 2003Publication date: September 25, 2003Applicant: Daicel Chemical Industries, Ltd.Inventor: Tatsuya Nakano
-
Publication number: 20030180665Abstract: 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: ApplicationFiled: March 21, 2003Publication date: September 25, 2003Inventor: Ying Wang
-
Publication number: 20030180661Abstract: 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: ApplicationFiled: March 11, 2003Publication date: September 25, 2003Inventors: Sang-jun Choi, Woo-sung Han, Sang-gyun Woo
-
Patent number: 6623907Abstract: 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: GrantFiled: February 1, 2001Date of Patent: September 23, 2003Assignee: JSR CorporationInventors: Jun Numata, Aki Suzuki, Hiromichi Hara, Norihiro Natsume, Kiyoshi Murata, Masafumi Yamamoto, Akimasa Soyano, Toru Kajita, Tsutomu Shimokawa
-
Patent number: 6617086Abstract: 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: GrantFiled: March 2, 2001Date of Patent: September 9, 2003Assignee: International Business Machines CorporationInventors: Marie Angelopoulos, Edward D. Babich, Inna V. Babich, Katherina E. Babich, James J. Bucchignano, Karen E. Petrillo, Steven A. Rishton
-
Publication number: 20030165776Abstract: 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: ApplicationFiled: December 30, 2002Publication date: September 4, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shoichiro Yasunami, Kunihiko Kodama
-
Patent number: 6613844Abstract: 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: GrantFiled: March 19, 2002Date of Patent: September 2, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Osamu Watanabe, Shimada Junji, Nagura Shigehiro, Takeda Takanobu
-
Publication number: 20030162128Abstract: 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: ApplicationFiled: December 4, 2002Publication date: August 28, 2003Applicant: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Tsing-Tang Song, Weir-Torn Jiang, Shung-Jim Yang, Sheng-Min Wang, Kom-Bei Shiu
-
Publication number: 20030157434Abstract: 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: ApplicationFiled: June 26, 2002Publication date: August 21, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Akio Oda, Hideo Miyake, Tomoyoshi Mitsumoto, Takeshi Serikawa, Ikuo Kawauchi, Ippei Nakamura
-
Publication number: 20030148211Abstract: The present invention provides a sulfonium salt represented by the following formula (I): 1Type: ApplicationFiled: November 27, 2002Publication date: August 7, 2003Inventors: Akira Kamabuchi, Kaoru Araki
-
Publication number: 20030148213Abstract: 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: ApplicationFiled: December 19, 2002Publication date: August 7, 2003Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Isamu Kaneko, Yoko Takebe, Shun-Ichi Kodama
-
Patent number: 6602650Abstract: 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: GrantFiled: March 13, 2002Date of Patent: August 5, 2003Assignee: Hynix Semiconductor IncInventors: Sung-eun Hong, Min-ho Jung, Jae-chang Jung, Geun-su Lee, Ki-ho Baik
-
Patent number: 6599678Abstract: 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: GrantFiled: June 25, 2001Date of Patent: July 29, 2003Assignee: Hynix Semiconductor IncInventors: Sung-eun Hong, Min-ho Jung, Jae-chang Jung, Geun-su Lee, Ki-ho Baik
-
Patent number: 6596458Abstract: 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: GrantFiled: May 3, 2000Date of Patent: July 22, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Kunihiko Kodama, Toshiaki Aoai, Yasumasa Kawabe
-
Patent number: 6596460Abstract: 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: GrantFiled: December 29, 2000Date of Patent: July 22, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Hans-Joachim Timpe, Ursula Müller
-
Patent number: 6589707Abstract: 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: GrantFiled: February 15, 2001Date of Patent: July 8, 2003Assignee: Hyundai Electronics Industries Co., Ltd.Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
-
Patent number: 6586152Abstract: 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: GrantFiled: June 12, 2000Date of Patent: July 1, 2003Assignee: Wako Pure Chemical Industries, Ltd.Inventors: Fumiyoshi Urano, Naoki Katano, Tomoko Kiryu
-
Publication number: 20030118942Abstract: 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: ApplicationFiled: August 14, 2002Publication date: June 26, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Tomoyoshi Mitsumoto, Noriaki Watanabe, Kazuo Maemoto
-
Publication number: 20030118939Abstract: 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: ApplicationFiled: November 9, 2001Publication date: June 26, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventors: Heidi Munnelly, Paul West
-
Patent number: 6582882Abstract: 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: GrantFiled: April 4, 2001Date of Patent: June 24, 2003Assignee: Kodak Polychrome Graphics LLCInventors: S. Peter Pappas, Shashikant Saraiya
-
Patent number: 6582880Abstract: 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: GrantFiled: September 7, 2001Date of Patent: June 24, 2003Assignees: 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: 20030111771Abstract: 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: ApplicationFiled: December 13, 2001Publication date: June 19, 2003Inventors: Alexander Sergeievich Gybin, Toshifumi Komatsu
-
Patent number: 6579659Abstract: 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: GrantFiled: April 3, 2001Date of Patent: June 17, 2003Inventors: Yasunori Uetani, Airi Yamada, Yoshiko Miya, Yoshiyuki Takata
-
Publication number: 20030108814Abstract: 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: ApplicationFiled: June 19, 2002Publication date: June 12, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Hideo Miyake, Akio Oda, Tomoyoshi Mitsumoto
-
Patent number: 6576392Abstract: 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: GrantFiled: December 6, 1999Date of Patent: June 10, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Kunihiko Kodama, Toshiaki Aoai, Hidekazu Ohashi
-
Patent number: 6576398Abstract: 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: GrantFiled: March 6, 2001Date of Patent: June 10, 2003Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Shinji Kishimura, Masaru Sasago, Masamitsu Shirai, Masahiro Tsunooka
-
Patent number: 6576400Abstract: 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: GrantFiled: May 10, 2000Date of Patent: June 10, 2003Assignee: Toray Industries, Inc.Inventor: Kazutaka Tamura
-
Publication number: 20030104314Abstract: 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: ApplicationFiled: September 5, 2001Publication date: June 5, 2003Applicant: Eastman Kodak CompanyInventors: Shiying Zheng, Kevin W. Williams
-
Publication number: 20030099897Abstract: 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: ApplicationFiled: February 25, 2002Publication date: May 29, 2003Applicant: MASS INSTITUTE OF TECHNOLOGY (MIT)Inventor: Theodore H. Fedynyshyn
-
Publication number: 20030099900Abstract: 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) 1Type: ApplicationFiled: September 26, 2002Publication date: May 29, 2003Inventors: Airi Yamada, Masumi Suetsugu, Yasunori Uetani
-
Patent number: 6569599Abstract: 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: GrantFiled: May 10, 2001Date of Patent: May 27, 2003Assignee: Hynix Semiconductor Inc.Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
-
Patent number: 6569602Abstract: 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: GrantFiled: May 18, 1999Date of Patent: May 27, 2003Assignee: E. I. du Pont de Nemours and CompanyInventor: Ying Wang
-
Patent number: 6566037Abstract: 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: GrantFiled: March 5, 2001Date of Patent: May 20, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeru Watanabe, Takeshi Kinsho, Jun Hatakeyama
-
Patent number: 6566038Abstract: 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: GrantFiled: April 26, 2001Date of Patent: May 20, 2003Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Takeshi Kinsho, Koji Hasegawa, Takeru Watanabe, Jun Hatakeyama
-
Publication number: 20030091927Abstract: 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: ApplicationFiled: August 22, 2002Publication date: May 15, 2003Applicant: HYNIX SEMICONDUCTOR INC.Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin, Se Jin Choi, Deog Bae Kim, Jae Hyun Kim
-
Publication number: 20030091926Abstract: 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: ApplicationFiled: December 11, 2002Publication date: May 15, 2003Applicant: Shipley Company, L.L.C.Inventor: James G. Shelnut
-
Publication number: 20030087183Abstract: 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: ApplicationFiled: August 29, 2002Publication date: May 8, 2003Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeshi Kinsho
-
Publication number: 20030087180Abstract: 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: ApplicationFiled: November 7, 2001Publication date: May 8, 2003Inventors: Takanori Kudo, Ralph R. Dammel, Munirathna Padmanaban
-
Publication number: 20030082479Abstract: 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: ApplicationFiled: June 25, 2002Publication date: May 1, 2003Applicant: 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: 6555289Abstract: 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: GrantFiled: April 6, 2001Date of Patent: April 29, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Tomoya Sasaki, Kazuyoshi Mizutani, Shoichiro Yasunami
-
Publication number: 20030077540Abstract: 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: ApplicationFiled: May 21, 2002Publication date: April 24, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
-
Patent number: 6551756Abstract: 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: GrantFiled: July 24, 2000Date of Patent: April 22, 2003Assignee: Napp Systems, Inc.Inventors: Yuxin Hu, Nathan J. Jacobsen
-
Patent number: 6551763Abstract: 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: GrantFiled: June 2, 2000Date of Patent: April 22, 2003Assignee: Kodak Polychrome Graphics LLCInventors: Anthony Paul Kitson, Peter Andrew Reath Bennett, Christopher David McCullough, Stuart Bayes, Kevin Barry Ray
-
Patent number: 6548219Abstract: 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: GrantFiled: January 26, 2001Date of Patent: April 15, 2003Assignee: International Business Machines CorporationInventors: Hiroshi Ito, Phillip Joe Brock, Gregory Michael Wallraff
-
Publication number: 20030068573Abstract: 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): 1Type: ApplicationFiled: July 31, 2002Publication date: April 10, 2003Inventors: Yoshiyuki Takata, Hiroaki Fujishima, Yasunori Uetani
-
Patent number: RE38256Abstract: 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: GrantFiled: November 24, 1999Date of Patent: September 23, 2003Assignee: Kabushiki Kaisha ToshibaInventors: Toru Ushirogouchi, Naomi Shida, Takuya Naito, Koji Asakawa, Akinori Hongu, Makoto Nakase, Hirokazu Niki