And Monomeric Processing Ingredient Patents (Class 430/191)
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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: 6210855Abstract: 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: GrantFiled: December 14, 1999Date of Patent: April 3, 2001Assignee: Shin Etsu Chemical Co., Ltd.Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
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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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 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: 6030741Abstract: The present invention provides a positive resist composition and method capable of achieving a resist pattern whose photosensitivity is less variable relative to its thickness, which exhibits small thickness reduction even when the pattern is fine, is capable of coping with irregularities in the exposure value since it has a wide focal-depth range, and exhibits reduced size-deviation from the mask size. The positive resist composition comprises (A) an alkali-soluble resin, (B) a quinonediazide-group-containing compound, and (C) an organic solvent, wherein the ingredient (C) is a mixture solvent containing (i) 2-heptanone, (ii) ethyl lactate, and (iii) a high-boiling organic solvent having a boiling point of 200 to 350.degree. C. The above-described resist pattern can be formed by using the positive resist composition.Type: GrantFiled: August 28, 1997Date of Patent: February 29, 2000Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kousuke Doi, Takako Suzuki, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 6020104Abstract: 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: January 27, 1999Date of Patent: February 1, 2000Assignee: JSR CorporationInventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
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Patent number: 6013407Abstract: A positive resist composition is excellent in sensitivity, film loss after development, resolution, thermal-flow resistance, storage stability, exposure margin and focus margin and comprises in combination (A) an alkali-soluble phenol resin, (B) a quinonediazide sulfonate type photosensitive agent and (C) a phenolic compound, wherein the phenolic compound (C) is at least one phenolic compound selected from the group consisting of phenolic compounds (CX) having a structural unit represented by the following formula (I) and phenolic compounds (CD) having a structural unit represented by the following formula (II): ##STR1## wherein R.sup.1 to R.sup.3 are, independently of one another, a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkenyl group which may be substituted, an alkoxy group which may be substituted, or an aryl group which may be substituted, R.sup.4 to R.sup.Type: GrantFiled: July 8, 1997Date of Patent: January 11, 2000Assignee: Nippon Zeon Co., Ltd.Inventors: Shoji Kawata, Hiroshi Hayashi, Hirokazu Higashi, Takeyoshi Kato, Masahiro Nakamura
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Patent number: 6007961Abstract: A radiation-sensitive resin composition including an alkali soluble resin and a quinonediazide compound is provided. The quinonediazide compound has the formula (1), for example: ##STR1## wherein, R.sup.1 to R.sup.6 are an alkyl, cycloalkyl or aryl group; a and b are an integer of 1 to 3; D.sup.1 and D.sup.2 are independently a hydrogen atom or a 1,2-quinonediazidosulfonyl group, provided that at least one of D.sup.1 is a 1,2-quinonediazidosulfonyl group; A is a bonding such as single bond; and x and y are an integer of 0 to 2. The composition is suitable as a positive resist, which effectively restrains the occurrence of scum, and excellent in developability, pattern shape, sensitivity, resolution and focus latitude.Type: GrantFiled: December 10, 1997Date of Patent: December 28, 1999Assignee: JSR CorporationInventors: Katsumi Inomata, Masahiro Akiyama, Shin-ichiro Iwanaga, Akira Tsuji
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Patent number: 6001517Abstract: A positive photosensitive polymer composition, which comprises a thermosetting polymer precursor which can be cured through cyclodehydration upon heating, and a photosensitive cure accelerator which can be inactivated of its cure accelerating property by irradiation of light.Type: GrantFiled: October 29, 1997Date of Patent: December 14, 1999Assignee: Kabushiki Kaisha ToshibaInventor: Yoshiaki Kawamonzen
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Patent number: 5998084Abstract: A positive-working, radiation-sensitive recording material capable of being used for the production of planographic printing plates, comprising: an aluminum support and a radiation-sensitive layer coated thereon, whereinthe aluminum support has been grained in nitric acid, then cleaned in sulfuric acid, anodized in sulfuric acid, and subsequently hydrophilized with a compound comprising at least one unit with a phosphonic acid or phosphonate group; andthe radiation-sensitive layer comprisesa) a radiation-sensitive 1,2-naphthoquinone-2-diazide-4- or -5-sulfonic acid ester of a polycondensate having phenolic hydroxy groups, said polycondensate being obtained by reacting a phenolic compound with an aldehyde or ketone,b) a novolak or a polycondensation product obtained by reacting a polyphenol with an aldehyde or ketone, as an alkali-soluble resin,c) a vinyl-type polymer comprising at least one unit having a lateral hydroxyphenyl group,d) a clathrate-forming compound,e) a low-molecular weight compound which comprType: GrantFiled: November 15, 1996Date of Patent: December 7, 1999Assignee: Agfa-Gevaert N.V.Inventors: Andreas Elsaesser, Raimund Haas, Guenter Hultzsch, Peter Lehmann, Rudolf Neubauer, Rudolf Zertani
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Patent number: 5985507Abstract: A high thermal alkali-soluble novolak binder resin, comprising the addition-condensation reaction product of a phenolic mixture with at least one aldehyde source, the feedstock of the phenolic mixture for the reaction comprising:(1) about 25 to about 40 weight percent of the phenolic mixture being a monomer selected from meta-cresol 2,5-xylenol or the combination thereof;(2) about 50 to about 70 weight percent of the phenolic mixture being para-cresol; and(3) about 3 to about 20 weight percent of the phenolic mixture being acetamidophenol; all percentages based on the weight of total phenol monomer feedstock.The invention is also directed to a positive working photoresist made from the composition.Type: GrantFiled: February 18, 1998Date of Patent: November 16, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
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Patent number: 5981135Abstract: A positive acting photoresist composition (e.g., a monolayer dry film) which is strippable in aqueous alkaline solution comprises a photo acid generator and a UV-transparent resin binder system which allows efficient photo bleaching of the photoactive component. An acid functional cellulosic resin may be the only binder resin, an acidic acrylate resin being optional. The dry coating is flexible and may be used as an etch and plating resist.Type: GrantFiled: August 13, 1997Date of Patent: November 9, 1999Assignee: Morton International, Inc.Inventors: Thomas A. Koes, Grieg B. Beltramo
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Patent number: 5958645Abstract: A radiation-sensitive resin composition comprising:(i) an alkali-soluble resin;(ii) a phenol compound represented by the following formula (1): ##STR1## wherein R.sub.1 to R.sub.4 each represent halogen, alkyl, alkoxyl, aryl, nitro, cyano, hydroxyalkyl, hydroxyalkoxyl or hydroxyl; a, b, c and d each represent an integer of 0 to 4 and satisfying 0.ltoreq.a+b.ltoreq.4 and 0.ltoreq.c+d.ltoreq.4, provided that when a+b is 1 and c+d is 1 at least one of R.sub.1 (or R.sub.2) and R.sub.3 (or R.sub.4) is alkyl, hydroxyalkyl or hydroxyalkoxyl; R.sub.5 to R.sub.10 each represent hydrogen, alkyl or aryl; and X.sub.1 and X.sub.2 each represent oxygen or sulfur atom; and(iii) a 1,2-quinonediazide compound. This composition has good resolution, sensitivity and developability, as well as has as a positive resist good focal latitude and heat resistance. The patterns formed have good shapes, and the composition may cause no fine particles during storage.Type: GrantFiled: August 27, 1997Date of Patent: September 28, 1999Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Kouichi Hirose, Masahiro Akiyama, Katsumi Inomata, Yoshiji Yumoto
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Patent number: 5948587Abstract: Provided is a positive working photoresist composition comprising (A) an alkali-soluble novolak resin obtained by condensation reaction of a mixture of phenols, which are constituted of specified proportions of m-cresol and two kinds of specific phenols, with an aldehyde and having a Mw/Mn ratio of from 1.5 to 4.0 (wherein Mw stands for a weight-average molecular weight, and Mn stands for a number-average molecular weight); (B) a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic acid ester as a photosensitive material; and (C) a low molecular weight compound having from 12 to 50 carbon atoms per molecule and from 2 to 8 phenolic hydroxy groups per molecule.Type: GrantFiled: September 19, 1996Date of Patent: September 7, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Yasumasa Kawabe, Shiro Tan
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Patent number: 5942368Abstract: A composition dispersing a colorant is disclosed. The dispersion composition comprises a compound represented by formula; ##STR1## Detailed definition is disclosed in the specification.Type: GrantFiled: April 22, 1997Date of Patent: August 24, 1999Assignee: Konica CorporationInventors: Takeo Akiyama, Shinya Watanabe
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Patent number: 5932389Abstract: This invention relates to alternating and block copolymer resins of uniform and controlled chain length and methods for preparing the same. The alternating copolymer resins are formed from the reaction of a bisoxymethylphenol, a reactive phenolic compound and a monooxymethylphenol. The alternating copolymer may then be further reacted with a second reactive compound in the presence of an aldehyde to form the substantially blocked copolymer. The resins of the invention are characterized by a low molecular weight distribution. The resins are useful for the formulation of high resolution photoresist materials.Type: GrantFiled: February 20, 1998Date of Patent: August 3, 1999Assignee: Shipley Company, L.L.C.Inventor: Anthony Zampini
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Patent number: 5912102Abstract: A positive resist composition comprising an alkali-soluble phenolic resin, a photosensitive agent composed of a quinonediazide sulfonate of a specific polyhydroxy compound, and an aromatic compound having at least one phenolic hydroxyl group.Type: GrantFiled: June 26, 1997Date of Patent: June 15, 1999Assignee: Nippon Zeon Co., Ltd.Inventors: Shoji Kawata, Motofumi Kashiwagi, Teturyo Kusunoki, Masahiro Nakamura
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Patent number: 5876895Abstract: A photosenstive resin composition for color filter having excellent resolution, heat resistance and transparency, etc., characterized in that it contains a novolak resin having the recurring units such as those represented by the general formula (I): ##STR1## ?wherein R.sub.1 to R.sub.5 represent hydrogen, alkyl, etc., and R.sub.6 and R.sub.7 represent hydrogen, alkyl, etc., provided that ##STR2## is coordinated at the o- or p-position in relation to the --OH group! and having a molecular weight of about 1,000-50,000, a solvent and a dye or pigment.Type: GrantFiled: May 24, 1996Date of Patent: March 2, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
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Patent number: 5861229Abstract: A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:X--.alpha.--H (I)wherein x is a group of the formula: ##STR1## and .alpha. is a divalent group which comprises a repeating unit of the formula: ##STR2## in which n is a number of not less than 1; a, b, c, d, e and f are the same or different and a number of 0-3, provided that d+f is not less than 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or an aryl group, which resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.Type: GrantFiled: September 22, 1992Date of Patent: January 19, 1999Assignee: Sumitomo Chemical Company, LimitedInventors: Haruyoshi Osaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
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Patent number: 5856058Abstract: Proposed is a novel chemical sensitization-type positive-working photoresist composition used for the photolithographic patterning works in the manufacture of semiconductor devices exhibiting an excellent halation-preventing effect in the patternwise exposure to light. The composition comprises, in addition to conventional ingredients including an acid-generating agent capable of releasing an acid by the irradiation with actinic rays and a resinous ingredient capable of being imparted with increased solubility in an aqueous alkaline developer solution in the presence of an acid, a unique halation inhibitor which is an esterification product between a specified phenolic compound and a naphthoquinone-1,2-diazide sulfonic acid.Type: GrantFiled: June 7, 1996Date of Patent: January 5, 1999Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Kazufumi Sato, Kazuyuki Nitta, Akiyoshi Yamazaki, Yoshika Sakai, Toshimasa Nakayama
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Patent number: 5853947Abstract: A photosensitive positive working photosensitive composition suitable for use as a photoresist, which comprises an admixture of at least one water insoluble, aqueous alkali soluble, film forming novolak resin; at least one o-diazonaphthoquinone photosensitizer; and a photoresist solvent mixture comprising a propylene glycol alkyl ether acetate and 3-methyl-3-methoxy butanol and process for producing such a composition.Type: GrantFiled: December 21, 1995Date of Patent: December 29, 1998Assignee: Clariant Finance (BVI) LimitedInventors: Stanley F. Wanat, M. Dalil Rahman, Dinesh N. Khanna, Daniel P. Aubin, Sunit S. Dixit
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Patent number: 5853949Abstract: Provided are a method of synthesizing a highly pure polyphenol compound, which comprises (i) introducing at least one --CHRNR'R" group onto aromatic ring(s) of a phenol compound having from one to ten aromatic ring(s), wherein R represents a hydrogen atom, an alkyl group which may contain a hetero atom, a cycloalkyl group which may contain a hetero atom, an aralkyl group which may contain a hetero atom, or an aryl group, and R' and R", which may be the same or different, each represents an alkyl group which may contain a hetero atom, a cycloalkyl group which may contain a hetero atom, an aralkyl group which may contain a hetero atom, or an aryl group, and R' and R" may combine with each other to form a ring, (ii) converting the --CHRNR'R" group into a --CHRA group via one to three steps, wherein A represents a hydroxyl group, an alkoxy group, an acyloxy group, a halogen atom, a quaternary ammonium salt or a sulfonyloxy group, and (iii) condensing the thus converted phenol compound and a phenol compound, and aType: GrantFiled: May 31, 1996Date of Patent: December 29, 1998Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Makoto Momota
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Patent number: 5853948Abstract: A positive photoresist composition comprising (A) an alkali-soluble resin; (B) a quinonediazido group containing compound; and (C) at least one sulfonyl halide represented by the following general formula (I):R.sup.1 --SO.sub.2 --X (I)where R.sup.1 is an alkyl group, a substituted alkyl group, an alkenyl group, an aryl group or a substituted aryl group; X is a halogen atom, as well as a multilayer resist material using this composition. Very fine (<0.4 .mu.m) resist patterns can be formed that have high feature or edge integrity, that provide good contrast between exposed and unexposed areas after development and that assure a wider margin of exposure, better depth-of-focus characteristics and sharper cross-sectional profiles.Type: GrantFiled: October 29, 1997Date of Patent: December 29, 1998Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Atsushi Sawano, Junichi Mizuta, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
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Patent number: 5849457Abstract: A positive-working resist composition comprising (A) a quinonediazide compound, (B) an alkali-soluble resin, and (C) a solvent system comprising 2-heptanone, ethyl lactate and .gamma.-butylactone in which the quinonediazide compound exhibits a very high solubility and which characteristics such as sensitivity, profile and coatability are excellent.Type: GrantFiled: October 24, 1997Date of Patent: December 15, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Katsuhiko Namba, Kaoru Tatekawa, Hiroshi Moriuma, Yasunori Uetani
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Patent number: 5837417Abstract: Process for producing a photosensitizer comprising a diazo ester of a p-cresol oligomer where at least one of the hydroxy groups on the p-cresol ring has been esterified with diazo-sulfonyl chloride comprising from about 60 to 100 mole % 2,1,4 or 2,1,5-diazo sulfonyl chloride, or a mixture thereof; and a photoresist comprising an admixture of the photosensitizer, which is present in the photoresist composition in an amount sufficient to uniformly photosensitive the photoresist composition, a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition, and a suitable solvent.Type: GrantFiled: December 30, 1994Date of Patent: November 17, 1998Assignee: Clariant Finance (BVI) LimitedInventors: M. Dalil Rahman, Dinesh N. Khanna, Daniel Aubin, Douglas McKenzie
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Patent number: 5827634Abstract: The invention comprises an acid hardened resist system consisting of a resin binder having acid labile blocking groups and inert blocking groups and a photoacid generator. The inclusion of inert blocking groups on the resin improves shelf life without deleteriously affecting photolithographic properties of the resist.Type: GrantFiled: March 12, 1997Date of Patent: October 27, 1998Assignee: Shipley Company, L.L.C.Inventors: James W. Thackeray, Roger F. Sinta, Mark D. Denison, Sheri L. Ablaza
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Patent number: 5807656Abstract: A polyhydroxy compound represented by the following formula (I): ##STR1## and a positive resist composition which comprises an alkali-soluble resin, a quinonediazide sulfonic acid ester, and a polyhydroxy compound of formula (I) or a polyhydroxy compound represented by the following formula (C): ##STR2## which is satisfactory in properties such as sensitivity, resolution, .tau.-value and peeling off resistance.Type: GrantFiled: September 4, 1996Date of Patent: September 15, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Haruyoshi Osaki, Yasunori Uetani, Yoshiyuki Takata
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Patent number: 5798201Abstract: A radiation sensitive resin composition containing an alkali soluble resin and a 1,2-quinonediazide compound of a polyphenol or a radiation sensitive resin composition containing an alkali soluble resin and a 1,2-quinonediazide compound and a polyphenol compound.Type: GrantFiled: July 2, 1997Date of Patent: August 25, 1998Assignees: Japan Synthetic Rubber Co., Ltd., Arakawa Chemical Industries, Ltd.Inventors: Katsumi Inomata, Nasahiro Akiyama, Toshiyuki Ota, Akira Tsuji
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Patent number: 5792585Abstract: A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, 1, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: March 25, 1994Date of Patent: August 11, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
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Patent number: 5783355Abstract: A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, 1, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.Type: GrantFiled: June 14, 1995Date of Patent: July 21, 1998Assignee: Sumitomo Chemical Company, LimitedInventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
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Patent number: 5776652Abstract: The invention relates to aromatic or heteroaromatic mono- or bis-diazonium 1,1,2,3,3,3-hexafluoro-propanesulfonates. They are employed in positive-working or negative-working radiation-sensitive mixtures which are used for coating radiation-sensitive recording material.Type: GrantFiled: October 14, 1997Date of Patent: July 7, 1998Assignee: Agfa-Gevaert AGInventors: Mathias Eichhorn, Gerhard Buhr
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Patent number: 5773200Abstract: A positive resist composition contains (1) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-10,000 as an alkali-soluble resin, (2) a low nucleus compound having a phenolic hydroxyl group and 2-5 benzene rings as a dissolution promoter, and (3) a compound having a 1,2-naphthoquinonediazidosulfonyl group in a molecule and a degree of esterification of at least 65% as a photosensitive agent. By forming a resist layer on a substrate from the positive resist composition, and baking the resist layer at 100.degree.-130.degree. C. before exposure or before development, followed by exposure and development, there is formed a resist pattern having a micro-groove of desired configuration. This resist pattern lends itself to a lift-off technique.Type: GrantFiled: December 15, 1995Date of Patent: June 30, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Okazaki, Kazuhiro Nishikawa, Masaru Kobayashi, Miki Kobayashi, Mitsuo Umemura, Toshinobu Ishihara