Polymeric Mixture Patents (Class 430/192)
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Publication number: 20010024762Abstract: A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 &mgr;m and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.Type: ApplicationFiled: February 28, 2001Publication date: September 27, 2001Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Publication number: 20010019808Abstract: A single layer lift-off resist composition comprising a novolac resin, a quinonediazidosulfonate photosensitive agent, and an aromatic hydroxy compound having at least one phenolic hydroxyl group in which the phenolic hydroxyl group is partially acylated is improved in adhesion to a substrate.Type: ApplicationFiled: February 22, 2001Publication date: September 6, 2001Inventors: Kazumi Noda, Tomoyoshi Furihata, Hideto Kato
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Patent number: 6284439Abstract: A photoresist having both positive and negative tone components resulting in a lower “k” factor than the single tone photoresist is disclosed. The hybrid resist may either have the negative tone resist or the positive tone resist as the major portion, while the other tone is a relatively minor portion. For examples, a positive tone resist may include a minor portion of a negative tone cross-linker or a negative tone resist may include positively acting functional groups. The hybrid resist of the present invention allows for wider exposure dosage windows, therefore increasing the yield or performance and line is density.Type: GrantFiled: June 30, 1998Date of Patent: September 4, 2001Assignee: International Business Machines CorporationInventors: Steven J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
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Publication number: 20010018160Abstract: A positive resist composition contains (A) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-20,000 wherein 2.5-27 mol % of the hydrogen atom of a hydroxyl group is replaced by a 1,2-naphthoquinonediazidosulfonyl group and (B) a low molecular aromatic compound having phenolic hydroxyl groups and 2-20 benzene rings wherein the ratio of the number of phenolic hydroxyl groups to the number of benzene rings is between 0.5 and 2.5. By forming a resist layer on a substrate from the positive resist composition and baking the resist layer at 90-130° C., followed by exposure and development, there is formed a resist pattern having an undercut of desired configuration. Owing to high resolution and improved dimensional control, heat resistance and film retention, the resist pattern lends itself to a lift-off technique.Type: ApplicationFiled: February 14, 2001Publication date: August 30, 2001Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
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Patent number: 6274287Abstract: A positive resist composition excellent in resolution, having a good balance with other performances required to resists and comprising an alkali-soluble resin, a radiation-sensitive ingredient and a hydroxyphenyl ketone compound represented by the following formula (I): wherein R1, R2, R3, R4 and R5 independently represent hydrogen, alkyl or alkoxy and n represents an integer of 1 to 3 is provided.Type: GrantFiled: June 22, 2000Date of Patent: August 14, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroshi Moriuma, Yoshiyuki Takata
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Patent number: 6270939Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymonocarboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.Type: GrantFiled: August 16, 2000Date of Patent: August 7, 2001Assignee: JSR CorporationInventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Publication number: 20010009746Abstract: Disclosed are a photosensitive polymer composition comprising (a) a polymer soluble in an aqueous alkaline solution, (b) an o-quinonediazide compound, and (c) a dissolution inhibitor for the component (a) in an aqueous alkaline solution; a method of using the composition for forming relief patterns; and electronic parts having, as a passivating film or an interlayer insulating film, the relief pattern as formed in the method. The composition has high sensitivity, and give fine relief patterns having a good profile.Type: ApplicationFiled: February 6, 2001Publication date: July 26, 2001Inventors: Masataka Nunomura, Noriyuki Yamazaki
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Patent number: 6265129Abstract: Improved positive photosensitive composition for application of the lift-off technique comprises (A) an alkali-soluble resin and (B) a mixture of two photosensitive agents in admixture with the alkali-soluble resin, one being (i) a photosensitive agent which shows the tendency to form a resist pattern of a feature profile having a micro-groove upon exposure and the other being (ii) a photosensitive agent which does not show the stated tendency but shows the tendency to form a resist pattern having a rectangular or tapered cross-sectional feature profile upon exposure and using the composition, one can form half-a-micron meter and even finer conducting patterns, electrodes or insulation patterns in a highly reproducible manner.Type: GrantFiled: November 7, 1997Date of Patent: July 24, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Koichi Takahashi, Tetsuya Kato, Tomosaburo Aoki
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Patent number: 6245478Abstract: A resist composition exhibiting an improved profile performance without impairing the resolution, the sensitivity, etc. which comprises a binder component; a radiation-sensitive component; and a succinimide compound represented by the following formula (I): wherein Q1 represents an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group; and Q2, which may be the same as or different from Q1, represents hydrogen, an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group.Type: GrantFiled: September 17, 1999Date of Patent: June 12, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Ichiki Takemoto
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Patent number: 6242151Abstract: The invention provides a novel polymer in the form of a novolac resin in which some of the hydrogen atoms of the hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted carbonyl or sulfonyl groups. The polymer has a weight average molecular weight calculated as polystyrene of 1,000-30,000. The polymer is formulated into a resist composition having improved uniformity, sensitivity, resolution and pattern geometry in microfabrication.Type: GrantFiled: August 11, 1999Date of Patent: June 5, 2001Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tomoyoshi Furihata, Hideto Kato, Satoshi Okazaki
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Patent number: 6232031Abstract: A positive-working, infrared imageable coating and a lithographic printing plate or other element with the coating are described. The coating is a phenolic resin containing an o-diazonaphthoquinone derivative which couples or reacts with the resin to partially insolubilize the coating and an infrared absorbing dye or pigment which further insolubilizes the coating and which renders the coating imageable by infrared radiation. The coating contains only that quantity of infrared radiation absorber necessary to be imageable and only that small quantity of o-diazonaphthoquinone derivative necessary to supplement the insolubilizing function of the absorber. Specifically, the absorber is from 1 to 10 weight percent of the total dry weight of the coating and the dry weight ratio of the absorber to the diazonaphthoquinone moiety is greater than 1:5 and preferably 1:2 or greater.Type: GrantFiled: March 30, 2000Date of Patent: May 15, 2001Assignee: Ano-Coil CorporationInventors: Robert F. Gracia, Yijin Ren, William J. Rozell, Howard A. Fromson
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Patent number: 6232032Abstract: Disclosed are a photosensitive polymer composition comprising (a) a polymer soluble in an aqueous alkaline solution, (b) an o-quinonediazide compound, and (c) a dissolution inhibitor for the component (a) in an aqueous alkaline solution; a method of using the composition for forming relief patterns; and electronic parts having, as a passivating film or an interlayer insulating film, the relief pattern as formed in the method. The composition has high sensitivity, and give fine relief patterns having a good profile.Type: GrantFiled: May 27, 1999Date of Patent: May 15, 2001Assignees: Hitachi Chemical DuPont Microsystems L.L.C., Hitachi Chemical DuPont Microsystems Ltd.Inventors: Masataka Nunomura, Noriyuki Yamazaki
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Patent number: 6228552Abstract: A photosensitive material, which comprises, an alkali-soluble resin moiety having an alicyclic skeleton, a polycyclic condensation skeleton, or both alicyclic and polycyclic condensation skeletons, and a diazo compound moiety. The diazo compound moiety may be contained in a side chain of the alkali-soluble resin moiety or included in the photosensitive material in separate from the alkali-soluble resin moiety.Type: GrantFiled: September 10, 1997Date of Patent: May 8, 2001Assignee: Kabushiki Kaisha ToshibaInventors: Takeshi Okino, Koji Asakawa, Naomi Shida, Toru Ushirogouchi, Makoto Nakase
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Patent number: 6228554Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymono-carboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.Type: GrantFiled: October 8, 1999Date of Patent: May 8, 2001Assignee: JSR CorporationInventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Patent number: 6218083Abstract: A method for producing a predetermined resist pattern on e.g. a lithographic printing plate, circuit board or mask comprises the imagewise exposure of a radiation sensitive diazide-containing coating (conventionally considered as a UV sensitive material), to non-UV radiation, such as direct heat radiation or infra-red radiation. A positive of the exposed image is revealed on development. Additionally, it has been found that a flood exposure to UV radiation after the imagewise exposure to the non-UV radiation means that a negative of the exposed image is revealed, on development.Type: GrantFiled: March 5, 1999Date of Patent: April 17, 2001Assignee: Kodak Plychrome Graphics, LLCInventors: Christopher D. McCullough, Kevin B. Ray, Alan S. Monk, Stuart Bayes, Anthony P. Kitson
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Patent number: 6218069Abstract: A photosensitive resin composition contains a photosensitive resin comprising recurring units of formula (1) and having a Mw of 1,300-11,000 and 20-5,000 ppm of a tertiary amine compound of formula (2). R is hydrogen or a 1,2-naphthoquinonediazido-5-sulfonic acid residue, the content of 1,2-naphthoquinonediazido-5-sulfonic acid residue in R is 3-27 mol %, and m is a number from 0 to 3, X is a C6-20 alkyl, aryl or aralkyl group, Y and Z each are a C1-20 alkyl group. The composition is improved in sensitivity stability and adhesion to substrates and eliminates the risk of causing corrosion of metal substrates.Type: GrantFiled: January 10, 2000Date of Patent: April 17, 2001Assignee: Shin-Etsu Chemical Co. Ltd.Inventors: Hideto Kato, Tomoyoshi Furihata, Satoshi Okazaki
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Patent number: 6214516Abstract: A positive photosensitive resin composition comprising (a) a silane diol such as diarylsilane diol or dialkylsilane diol, (b) one or more polybenzoxazole precursors having the structure: wherein Ar1 is a tetravalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Ar2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; (c) a photosensitive agent, and (d) a solvent. The composition optionally includes an adhesion promoter, leveling agent, or mixtures thereof.Type: GrantFiled: March 24, 2000Date of Patent: April 10, 2001Assignee: Arch Specialty Chemicals, Inc.Inventors: Pamela J. Waterson, Ahmad Naiini, Steve Lien-Chung Hsu, William D. Weber
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Patent number: 6207356Abstract: A method of pattern-processing a photosensitive resin composition which comprises coating on a substrate a positive photosensitive resin composition of a polyamide of formula (1) below and a diazoquinone compound, subjecting the same to prebaking and then to irradiation with light, thereafter dissolving the exposed portion in an alkaline aqueous solution containing an alkylbenzenesulfonic acid to remove the same, thereby obtaining a pattern. wherein X is a tetravalent aromatic group; Y is a divalent aromatic group; Z is in which R1 and R2 are divalent organic groups and R3 and R4 are nonvalent organic groups; a and b are mole fractions; a+b=100 mole %; a=60.0-100 mole %; b=0-40.0 mole % and n=2-500. When the development is effected with the alkaline aqueous solution containing the alkylbenzenesulfonic acid, a scum-free, very high resolution pattern is obtained.Type: GrantFiled: April 7, 1999Date of Patent: March 27, 2001Assignee: Sumitomo Bakelite Company LimitedInventors: Toshio Banba, Toshiro Takeda
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Patent number: 6207788Abstract: A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho—ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.Type: GrantFiled: July 24, 1998Date of Patent: March 27, 2001Assignee: Tokyo Ohka Kogya Co., Ltd.Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6207340Abstract: A positive photoresist composition for forming a contact hole which comprises (A) an alkali-soluble resin; (B) a naphthoquinonediazide group-containing compound; and (C) a solvent, wherein the ingredient (B) comprises: at least one naphthoquinonediazidesulfonic ester of a polyphenol compound, where said polyphenol compound is composed of from 4 to 6 benzene rings each bonding via a methylene chain, each of the methylene chains is in a meta position to other methylene chains, and each of the benzene rings has a hydroxyl group is provided. According to the present invention, a positive photoresist composition and a process for forming a contact hole can be provided each of which gives a contact hole pattern image in exact accordance with a mask pattern without dimple formation, in the contact hole forming technologies using the phaseshift method.Type: GrantFiled: March 31, 2000Date of Patent: March 27, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6197473Abstract: The objectives of the present invention are to provide a photosensitive composition having high solubility to organic solvents as well as to alkaline developers or water-base developers of pH 11 or less, and to provide a pattern forming process for obtaining a high-resolution resist pattern. These objectives are achieved by means of a photosensitive composition comprising a compound which is glassy at room temperature and has a cyclic structure with three or more aromatic rings containing an acid-decomposable substituent, and a pattern forming process wherein a photosensitive material using said photosensitive composition is exposed to a light pattern and developed with an aqueous solution of an alkali or with a water-base developer of pH 11 or less.Type: GrantFiled: September 17, 1998Date of Patent: March 6, 2001Assignee: Kabushiki Kaisha ToshibaInventors: Naoko Kihara, Satoshi Saito, Toru Ushirogouchi
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Patent number: 6190829Abstract: A photoresist having both positive and negative tone components resulting in a lower “k” factor than the single tone photoresist is disclosed. The hybrid resist may either have the negative tone resist or the positive tone resist as the major portion, while the other tone is a relatively minor portion. For examples, a positive tone resist may include a minor portion of a negative tone cross-linker or a negative tone resist may include positively acting functional groups. The hybrid resist of the present invention allows for wider exposure dosage windows, therefore increasing the yield or performance and line density.Type: GrantFiled: September 16, 1996Date of Patent: February 20, 2001Assignee: International Business Machines CorporationInventors: Steve J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
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Patent number: 6190833Abstract: A radiation-sensitive resin composition comprising: (A) a phenol resin, (B) an amino resin, (C) a compound having two or more crosslinking groups in a molecule, and (D) a halomethyl-1,3,5-triazine compound. The composition can form insulating layers exhibiting high resolution, high plating solution resistance, high adhesion to conductor wiring, and developability using an alkaline aqueous solution, producing cured insulating layers with superior solvent resistance, excellent waterproofing characteristics, and high heat resistance. The composition is useful for fabricating multilayered wiring boards.Type: GrantFiled: September 30, 1998Date of Patent: February 20, 2001Assignee: JSR CorporationInventors: Atsushi Shiota, Masako Suzuki, Hozumi Sato
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Patent number: 6190825Abstract: The invention relates to polymers containing N-substituted maleimide units, to a positive- or negative-working radiation-sensitive mixture comprising a) a polymeric binder which is insoluble in water, but soluble in aqueous-alkaline solutions, and b) at least one radiation-sensitive compound, where the binder comprises a polymer containing N-substituted maleimide units of the formula (I) The invention furthermore relates to a recording material having a support and a radiation-sensitive layer, where the layer includes the mixture. The recording material is particularly suitable for the production of chemical-resistant relief recordings. The planographic printing plates produced from the recording material allow long print runs and are resistant to processing chemicals.Type: GrantFiled: January 29, 1999Date of Patent: February 20, 2001Assignee: Agfa-Gevaert N.V.Inventors: Steffen Denzinger, Andreas Elsaesser
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Patent number: 6187500Abstract: In a positive photoresist composition including (A) an alkali-soluble novolak resin and (B) a naphthoquinonediazide ester, the alkali-soluble novolak resin is obtained synthetically by condensation of phenol compounds and an aldehyde or ketone, and the phenol compounds include, for example, 1% to 20% by mole of hydroquinone, 30% to 95% by mole of m-cresol and 2% to 50% by mole of 2,5-xylenol. Thus, a high-definition positive photoresist composition can be obtained, which inhibits the formation of scum, and is satisfactory in sensitivity, sectional shape, focal depth range and other properties even in a process for the formation of an ultrafine resist pattern of 0.30 &mgr;m or below by lithography using i-ray.Type: GrantFiled: November 2, 1999Date of Patent: February 13, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Ken Miyagi, Kousuke Doi, Atsuko Hirata, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6177225Abstract: A positive photosensitive resin composition. The composition comprising: (a) a capped polybenzoxazole precursor polymer having the structure; wherein Ar1 is a tetravalent aromatic group, aliphatic group, heterocylic group, or mixtures thereof; Ar2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Z is one of the following groups: x is 10 to 1000; y is 0 to 900; and b is 0.10 to 350; (b) a photosensitive agent; and (c) a solvent.Type: GrantFiled: September 24, 1999Date of Patent: January 23, 2001Assignee: Arch Specialty Chemicals, Inc.Inventors: William D. Weber, Pamela J. Waterson, Steve Lien-Chung Hsu, Ahmad Naiini
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Patent number: 6177226Abstract: A positive photoresist composition for forming a contact hole which comprises (A) an alkali-soluble resin; (B) a naphthoquinonediazide group-containing compound; and (C) a solvent, wherein the ingredient (B) comprises: at least one naphthoquinonediazidesulfonic ester of a polyphenol compound, where said polyphenol compound is composed of from 4 to 6 benzene rings each bonding via a methylene chain, each of the methylene chains is in a meta position to other methylene chains, and each of the benzene rings has a hydroxyl group is provided. According to the present invention, a positive photoresist composition and a process for forming a contact hole can be provided each of which gives a contact hole pattern image in exact accordance with a mask pattern without dimple formation, in the contact hole forming technologies using the phaseshift method.Type: GrantFiled: April 29, 1998Date of Patent: January 23, 2001Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6171750Abstract: A radiation-sensitive resin composition including (A) an alkali-soluble novolak resin obtained by condensing a particular combination of a first phenol having formula: wherein R1 and R2 are the same or different and each represent an alkyl group, a cycloalkyl group, an alkoxyl group or an aryl group; and a second phenol selected from the group consisting of phenol, o-cresol, m-cresol, p-cresol, 2,3-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, resorcinol, 2-methylresorcinol, 4-ethylresorcinol, hydroquinone, methylhydroquinone, catechol, 4-methyl-catechol, pyrogallol, phloroglucinol, thymol and isothymol with an aldehyde in the presence of an acidic catalyst; and (B) a quinonediazidosulfonic acid ester compound. This composition exhibits good resolution, developability, heat resistance, pattern shape, exposure margin and focal latitude in a well balanced state.Type: GrantFiled: June 10, 1998Date of Patent: January 9, 2001Assignee: JSR CorporationInventors: Katsumi Inomata, Katsuji Douki, Tooru Mizumachi, Shin-ichiro Iwanaga
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Patent number: 6156474Abstract: To provide a positive type photoresist composition which is capable of forming a resist pattern having an excellent adhesion to a substrate, a positive type photoresist composition comprising a polymer containing a specified amount of a polypropylene oxide group and a polyethylene oxide group is provided.Type: GrantFiled: December 2, 1998Date of Patent: December 5, 2000Assignee: Shipley Company, L.L.C.Inventors: Sigeki Nakano, Akira Awaji, Teruaki Ogawa, Kenta Takahashi
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Patent number: 6153350Abstract: The polybenzoxazole and polybenzothiazole precursors of the invention have the following partial structure: ##STR1## where: A.sup.1 to A.sup.6 are--independently of one another--H, F, CH.sub.3, CF.sub.3, OCH.sub.3, OCF.sub.3, CH.sub.2 CH.sub.3, CF.sub.2 CF.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.3 CF.sub.3 ;T is O or S, and m is 1;Z is a carbocyclic or heterocyclic aromatic radical.Type: GrantFiled: September 25, 1998Date of Patent: November 28, 2000Assignee: Siemens AktiengesellschaftInventors: Recai Sezi, Michael Keitmann, Gunther Schmid
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Patent number: 6140019Abstract: A radiation sensitive composition comprising (A) a colorant containing a quinacridone pigment, a mixture of an isoindolinone pigment and a yellow organic pigment or a mixture of copper phthalocyanine blue and a green pigment, (B) an alkali-soluble resin, (C) a polyfunctional monomer and (D) a photopolymerization initiator. The composition is useful for production of an additive or subtractive color filter which is used in a reflection-type color liquid crystal display device.Type: GrantFiled: July 23, 1998Date of Patent: October 31, 2000Assignee: JSR CorporationInventors: Kouichi Sakurai, Hiroaki Nemoto, Atsushi Kumano
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Patent number: 6140026Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.Type: GrantFiled: December 8, 1999Date of Patent: October 31, 2000Assignee: Arch Specialty Chemicals, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
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Patent number: 6127086Abstract: A positive photosensitive resin composition comprising (a) a silane diol such as diarylsilane diol or dialkylsilane diol, (b) one or more capped polybenzoxazole precursors having the structure: ##STR1## wherein Ar.sub.1 is a tetravalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Ar.sub.2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar.sub.3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof;Z is one of the following groups: ##STR2## x is 10 to 1000; y is 0 to 900; and b is 0.10 to 350; (c) a photosensitive agent, and (d) a solvent. The composition optionally includes an adhesion promoter, leveling agent, or mixtures thereof.Type: GrantFiled: September 24, 1999Date of Patent: October 3, 2000Assignee: Arch Specialty Chemicals, Inc.Inventors: Pamela J. Waterson, Ahmad Naiini, Steve Lien-Chung Hsu, William D. Weber
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Patent number: 6127087Abstract: A positive photoresist composition comprises (A) an alkali-soluble resin, and (B) at least one quinonediazide group-containing compound in which part or all of the hydroxyl groups of a compound represented by the following formula (I) are esterified with a quinonediazidesulfonic acid: ##STR1## wherein each of R.sup.1 and R.sup.2 is an alkyl group having 1 to 5 carbon atoms, and "a" is 0 or 1. The present invention provides a positive photoresist composition which can form a resist pattern having high film residual rate, improved development contrast between exposed portions and unexposed portions, and satisfactory definition, exposure margin, focal depth range properties and sectional shape.Type: GrantFiled: June 17, 1998Date of Patent: October 3, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Miki Kobayashi, Kousuke Doi, Sachiko Tamura, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6120969Abstract: Disclosed is, for example, bis(2,5-dimethyl-3-(2-hydroxy-5-ethylbenzyl)-4-hydroxyphenyl)methane and quinonediazide ester thereof. These are used for positive photoresist compositions. According to the invention, positive photoresist compositions having a high definition, a high sensitivity and a large exposure margin can be provided.Type: GrantFiled: April 2, 1999Date of Patent: September 19, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Mitsuo Hagihara, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama, Tetsuya Nakajima
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Patent number: 6120970Abstract: The polybenzoxazole and polybenzothiazole precursors of the invention have the following partial structure: ##STR1## where: A.sup.1 to A.sup.7 are--independently of one another--H, F, CH.sub.3, CF.sub.3, OCH.sub.3, OCF.sub.3, CH.sub.2 CH.sub.3, CF.sub.2 CF.sub.3, OCH.sub.2 CH.sub.3 or OCF.sub.2 CF.sub.3 ;T is O or S, and m is 1;Z is a carbocyclic or heterocyclic aromatic radical.Type: GrantFiled: September 25, 1998Date of Patent: September 19, 2000Assignee: Siemens AktiengesellschaftInventors: Recai Sezi, Michael Keitmann
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Patent number: 6117610Abstract: An infrared imaging composition contains two essential components, a non-basic infrared radiation absorbing material (such as carbon black), and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in positive-working or negative-working imaging elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.Type: GrantFiled: August 8, 1997Date of Patent: September 12, 2000Assignee: Kodak Polychrome Graphics LLCInventors: Eugene L. Sheriff, Paul R. West, Jeffery A. Gurney, Thap DoMinh
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Patent number: 6106994Abstract: A process for producing a polyphenol diester comprises esterifying a polyphenol compound and a naphthoquinone-1,2-diazidesulfonyl halide in the presence of for example monomethyldicyclohexylamine, and a positive photosensitive composition contains the resultant ester. According to this process, a diester of any polyphenol compound can be obtained with ease in a good yield, and a composition using the diester can achieve a high definition and a satisfactory exposure margin.Type: GrantFiled: December 14, 1998Date of Patent: August 22, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6103443Abstract: A photoresist composition comprising a film forming resin obtained by condensing a phenol derivative and a substituted diphenyl ether, a photoactive compound, and a solvent. The photoresist composition may also contain an alkali-soluble, film-forming resin, such as a novolak resin. The photoresist of the instant invention improves the photospeed, resolution and thermal stability of the photoresist images.Type: GrantFiled: November 21, 1997Date of Patent: August 15, 2000Assignee: Clariant Finance LmitedInventors: Stanley F. Wanat, Kathryn H. Jensen, Ping-Hung Lu, Douglas McKenzie
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Patent number: 6100004Abstract: A positive-working or negative-working radiation-sensitive mixture includes as an IR absorbing component a carbon black pigment having a primary particle size smaller than 80 nm. The carbon black pigment is predispersed in a polymer containing acidic units having a pK.sub.a of less than 13. The radiation-sensitive component may include an ester of (i) a 1,2-naphthoquinone-2-diazide-4-sulfonic acid or a 1,2-naphthoquinone-2-diazide-5-sulfonic acid and (ii) a compound having at least one phenolic hydroxyl group, such as 3 to 6 phenolic hydroxyl groups. After imagewise radiation exposure, the recording material including the radiation-sensitive mixture can be developed without difficulties in an aqueous alkaline solution without leaving residual coating on the areas that became soluble or that remained soluble upon exposure.Type: GrantFiled: March 11, 1998Date of Patent: August 8, 2000Assignee: Agfa-Gevaert N.V.Inventors: Andreas Elsaesser, Otfried Gaschler, Helmut Haberhauer, Mathias Eichhorn, Fritz-Feo Grabley, Thomas Leichsenring, Gabor I. Koletar, Douglas A. Seeley
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Patent number: 6090526Abstract: The present invention provides novel polymers and photoresist compositions that contain such polymers as a resin binder component. The polymers of the invention include repeating units that contain an acetalester or ketalester moiety. Preferred photoresists of the invention are chemically-amplified positive-acting compositions that contain a polymer with acetalester or ketalester unit as a resin binder component and that can react to provide solubility differences in the presence of photo-generated acid.Type: GrantFiled: September 13, 1996Date of Patent: July 18, 2000Assignee: Shipley Company, L.L.C.Inventor: Uday Kumar
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Patent number: 6083657Abstract: Phenolic compound (a) is polycondensed with mixed aldehyde (b) consisting essentially of 5-30 mol % of unsaturated aliphatic aldehyde (b-1) and 70-95 mol % of saturated aliphatic aldehyde (b-2) to give alkali-soluble novolak resin (A) as the product of polycondensation reaction. The alkali-soluble novolak resin (A) is used with quinonediazido group containing compound (B) to produce a positive photoresist composition. According to the present invention, there are specifically provided a positive photoresist composition that has high feature integrity in spite of high sensitivity and which yet provides a great depth of focus, a process for producing such positive photoresist composition, as well as an alkali-soluble novolak resin that can advantageously be used in such composition, and a method of forming patterns with high reproducibility using such positive photoresist composition.Type: GrantFiled: January 15, 1999Date of Patent: July 4, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Shinichi Kono, Yasuo Masuda, Atsushi Sawano, Hayato Ohno, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6080522Abstract: A radiation sensitive resist composition with high sensitivity, capable of forming a highly heat-resistant resist pattern. The radiation-sensitive resist composition contains, together with a resist material, a polymer which is obtained by reacting (a) a xylylene compound, (b) salicylic acid and (c) 9,9'-bis(hydroxyphenyl)fluorene derivatives or diol compounds of 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene, and which has a weight average molecular weight of 1,000 to 5,000 and Tg of 100 to 150.degree. C. Examples of (c) include 9,9'-bis(4-hydroxyphenyl)fluorene and 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene-6,6'-diol. As the resist material, any of positive- and negative-working resists may be used, with that comprising an alkali-soluble resin and a quinonediazide photo-sensitizer being preferably used.Type: GrantFiled: February 26, 1999Date of Patent: June 27, 2000Assignee: Clariant Internaitonal, Ltd.Inventors: Hiromi Ito, Hatsuyuki Tanaka
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Patent number: 6071666Abstract: A positive type photosensitive resin composition which comprises (A) 100 parts by weight of a polyamide represented by the general formula (1): ##STR1## wherein X represents a tetravalent aromatic group; Y represents a divalent aromatic group; Z represents a group represented by the formula: ##STR2## in which R.sub.1 and R.sub.2 represent organic groups and R.sub.3 and R.sub.4 represent monovalent organic groups; a and b represent molar fractions; a+b=100 mole %; a=60.0-100.0 mole %; b=0-40.0 mole %; and n represents an integer of 2 to 500, (B) 1 to 100 parts by weight of a photosensitive diazoquinone compound and (C) 1 to 50 parts by weight of a phenol compound represented by a specific structural formula and/or (D) 0.1 to 20 parts by weight of an organosilicon compound represented by a specific structural formula; and a semiconductor device in which a pattern of a polybenzoxazole resin obtained by using the above photosensitive resin composition is formed in a thickness of 0.1 to 20 .mu.Type: GrantFiled: May 12, 1997Date of Patent: June 6, 2000Assignee: Sumitomo Bakelite Company, Ltd.Inventors: Takashi Hirano, Toshio Banba, Hiroaki Makabe, Naoshige Takeda, Toshiro Takeda
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Patent number: 6068962Abstract: A non-chemically enhanced type positive resist composition includes an alkali-soluble novolak resin, a quinonediazide type sensitizer and at least one of the following compounds (a) and (b):(a) an acid-generator which is decomposed by the action of an alkali developer and generates an acid, and(b) compounds represented by the following formula (IV) or (V): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently represents hydrogen, halogen, hydroxy, alkyl, alkoxy, aryl or nitro, each of R.sup.9 and R.sup.10 independently represents hydrogen, halogen, alkyl, aryl, nitro, a group of --(CH.sub.2).sub.n --OR.sup.11 or a group of --(CH.sub.2).sub.n --COOR.sup.12 in which R.sup.11 represents hydrogen, alkyl, aryl or alkanoyl and R.sup.12 represents hydrogen, alkyl or aryl, and n is a number from 0 to 3 and R.sup.13 represents hydrogen, halogen, alkyl, alkoxy or aryl.Type: GrantFiled: September 19, 1997Date of Patent: May 30, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Yasunori Uetani, Hiroshi Moriuma, Jun Tomioka
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Patent number: 6066438Abstract: A method for fixing, on a substrate, functional material such as proteins, enzymes, polysaccharides, nucleic acids, microorganisms, viruses and cultured cells, includes the steps of (i) forming on the substrate a photosensitive layer containing DNQ, novolak, and optionally imidazole; (ii) applying onto the substrate functional material containing at least one amino group; (iii) before or after step (ii), irradiating in a pattern the photosensitive layer with light of appropriate wavelength(s) to convert DNQ to a ketene compound; and (iv) reacting the amino group with the ketene compound to fix via amido bonding the functional material to the substrate via the photosensitive layer along the pattern.Type: GrantFiled: March 10, 1997Date of Patent: May 23, 2000Assignee: Director General of Industrial Science & TechnologyInventors: Dan V. Nicolau, Takahisa Taguchi, Susumu Yoshikawa
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Patent number: 6051358Abstract: An unsymetrical photoactive compound having the formula ##STR1## where Z is hydrogen, a hydrocarbon having from 1 to 8 carbon atoms, or halogen; D is hydrogen or diazo-oxo-naphthalene-sulfonyl; n is equal to 1 to 4; R.sub.1, R.sub.5 and R.sub.6 are independently a hydrocarbon or halogen; R.sub.2 is the same as R.sub.1 or hydrogen; each R.sub.3 is the same as R.sub.2, hydroxyl or --OD; and each R.sub.4 is the same as R.sub.2 or another substituent provided that at least one R.sub.2, or one or both R.sub.4 is other than hydrogen, at least 2 Ds are diazo-oxo-sulfonyl group and at least 50 mole percent of the mixture conforms to the formula where n equals 1. The compounds of the invention are suitable for formation of storage stable photoresist compositions.Type: GrantFiled: November 4, 1997Date of Patent: April 18, 2000Assignee: Shipley Company, L.L.C.Inventors: Anthony Zampini, Harold F. Sandford
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Patent number: 6048659Abstract: A radiation-sensitive resin composition including (1) an alkali-soluble resin, (2) a quinonediazide compound and (3) a mixed solvent including a monoketone having 7 to 14 carbon atoms and an alkoxypropionic acid alkyl ester is provided. The composition can be coated in a uniform thickness in a small coating weight. The composition has a high sensitivity and a high resolution, and also enables formation of resist patterns having a superior pattern shape with less pattern defects. Thus, it is suitable as a positive resist.Type: GrantFiled: October 2, 1998Date of Patent: April 11, 2000Assignee: JSR CorporationInventors: Masaaki Inoue, Katsumi Inomata, Hiromichi Hara, Yoshiji Yumoto
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Patent number: 6040107Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.Type: GrantFiled: February 6, 1998Date of Patent: March 21, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
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Patent number: RE37179Abstract: A radiation sensitive resin composition which comprises (A) a polymer which becomes alkali-soluble in the presence of an acid and (B) a radiation sensitive acid generator which generates an acid upon irradiation with a radiation, said polymer (A) comprising two recurring units represented by the general formulas (1) and (2) and a recurring unit which acts to reduce the solubility of the polymer is an alkali developer after the irradiation: wherein R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or a methyl group. Said composition provides a chemically amplified positive resist which can give a fine pattern with a good pattern shape, and said resist is freed from volume shrinkage, peeling failure and adhesive failure, is excellent in dry etching resistance and effectively reacts with various radiations to give a good pattern shape which is excellent in photolithographic process stability, said pattern shape having no thinned portion at the upper part.Type: GrantFiled: October 21, 1999Date of Patent: May 15, 2001Assignee: JSR CorporationInventors: Mikio Yamachika, Eiichi Kobayashi, Akira Tsuji, Toshiyuki Ota