And Monomeric Processing Ingredient Patents (Class 430/191)
  • Patent number: 6214516
    Abstract: 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: Grant
    Filed: March 24, 2000
    Date of Patent: April 10, 2001
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Pamela J. Waterson, Ahmad Naiini, Steve Lien-Chung Hsu, William D. Weber
  • Patent number: 6210855
    Abstract: 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: Grant
    Filed: December 14, 1999
    Date of Patent: April 3, 2001
    Assignee: Shin Etsu Chemical Co., Ltd.
    Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
  • Patent number: 6207788
    Abstract: 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: Grant
    Filed: July 24, 1998
    Date of Patent: March 27, 2001
    Assignee: Tokyo Ohka Kogya Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6207340
    Abstract: 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: Grant
    Filed: March 31, 2000
    Date of Patent: March 27, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6197473
    Abstract: 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: Grant
    Filed: September 17, 1998
    Date of Patent: March 6, 2001
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naoko Kihara, Satoshi Saito, Toru Ushirogouchi
  • Patent number: 6190829
    Abstract: 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: Grant
    Filed: September 16, 1996
    Date of Patent: February 20, 2001
    Assignee: International Business Machines Corporation
    Inventors: Steve J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
  • Patent number: 6187500
    Abstract: 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: Grant
    Filed: November 2, 1999
    Date of Patent: February 13, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Atsuko Hirata, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6177226
    Abstract: 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: Grant
    Filed: April 29, 1998
    Date of Patent: January 23, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6177225
    Abstract: 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: Grant
    Filed: September 24, 1999
    Date of Patent: January 23, 2001
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: William D. Weber, Pamela J. Waterson, Steve Lien-Chung Hsu, Ahmad Naiini
  • Patent number: 6171750
    Abstract: 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: Grant
    Filed: June 10, 1998
    Date of Patent: January 9, 2001
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Katsuji Douki, Tooru Mizumachi, Shin-ichiro Iwanaga
  • Patent number: 6156474
    Abstract: 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: Grant
    Filed: December 2, 1998
    Date of Patent: December 5, 2000
    Assignee: Shipley Company, L.L.C.
    Inventors: Sigeki Nakano, Akira Awaji, Teruaki Ogawa, Kenta Takahashi
  • Patent number: 6127087
    Abstract: 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: Grant
    Filed: June 17, 1998
    Date of Patent: October 3, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Miki Kobayashi, Kousuke Doi, Sachiko Tamura, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6127086
    Abstract: 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: Grant
    Filed: September 24, 1999
    Date of Patent: October 3, 2000
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Pamela J. Waterson, Ahmad Naiini, Steve Lien-Chung Hsu, William D. Weber
  • Patent number: 6120969
    Abstract: 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: Grant
    Filed: April 2, 1999
    Date of Patent: September 19, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuo Hagihara, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama, Tetsuya Nakajima
  • Patent number: 6117610
    Abstract: 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: Grant
    Filed: August 8, 1997
    Date of Patent: September 12, 2000
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Eugene L. Sheriff, Paul R. West, Jeffery A. Gurney, Thap DoMinh
  • Patent number: 6103443
    Abstract: 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: Grant
    Filed: November 21, 1997
    Date of Patent: August 15, 2000
    Assignee: Clariant Finance Lmited
    Inventors: Stanley F. Wanat, Kathryn H. Jensen, Ping-Hung Lu, Douglas McKenzie
  • Patent number: 6100004
    Abstract: 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: Grant
    Filed: March 11, 1998
    Date of Patent: August 8, 2000
    Assignee: Agfa-Gevaert N.V.
    Inventors: Andreas Elsaesser, Otfried Gaschler, Helmut Haberhauer, Mathias Eichhorn, Fritz-Feo Grabley, Thomas Leichsenring, Gabor I. Koletar, Douglas A. Seeley
  • Patent number: 6083657
    Abstract: 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: Grant
    Filed: January 15, 1999
    Date of Patent: July 4, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Kono, Yasuo Masuda, Atsushi Sawano, Hayato Ohno, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6071666
    Abstract: 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: Grant
    Filed: May 12, 1997
    Date of Patent: June 6, 2000
    Assignee: Sumitomo Bakelite Company, Ltd.
    Inventors: Takashi Hirano, Toshio Banba, Hiroaki Makabe, Naoshige Takeda, Toshiro Takeda
  • Patent number: 6068962
    Abstract: 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: Grant
    Filed: September 19, 1997
    Date of Patent: May 30, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Hiroshi Moriuma, Jun Tomioka
  • Patent number: 6066438
    Abstract: 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: Grant
    Filed: March 10, 1997
    Date of Patent: May 23, 2000
    Assignee: Director General of Industrial Science & Technology
    Inventors: Dan V. Nicolau, Takahisa Taguchi, Susumu Yoshikawa
  • Patent number: 6048659
    Abstract: 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: Grant
    Filed: October 2, 1998
    Date of Patent: April 11, 2000
    Assignee: JSR Corporation
    Inventors: Masaaki Inoue, Katsumi Inomata, Hiromichi Hara, Yoshiji Yumoto
  • Patent number: 6030741
    Abstract: 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: Grant
    Filed: August 28, 1997
    Date of Patent: February 29, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kousuke Doi, Takako Suzuki, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6020104
    Abstract: 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: Grant
    Filed: January 27, 1999
    Date of Patent: February 1, 2000
    Assignee: JSR Corporation
    Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
  • Patent number: 6013407
    Abstract: 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: Grant
    Filed: July 8, 1997
    Date of Patent: January 11, 2000
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shoji Kawata, Hiroshi Hayashi, Hirokazu Higashi, Takeyoshi Kato, Masahiro Nakamura
  • Patent number: 6007961
    Abstract: 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: Grant
    Filed: December 10, 1997
    Date of Patent: December 28, 1999
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Masahiro Akiyama, Shin-ichiro Iwanaga, Akira Tsuji
  • Patent number: 6001517
    Abstract: 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: Grant
    Filed: October 29, 1997
    Date of Patent: December 14, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Yoshiaki Kawamonzen
  • Patent number: 5998084
    Abstract: 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 compr
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: December 7, 1999
    Assignee: Agfa-Gevaert N.V.
    Inventors: Andreas Elsaesser, Raimund Haas, Guenter Hultzsch, Peter Lehmann, Rudolf Neubauer, Rudolf Zertani
  • Patent number: 5985507
    Abstract: 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: Grant
    Filed: February 18, 1998
    Date of Patent: November 16, 1999
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
  • Patent number: 5981135
    Abstract: 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: Grant
    Filed: August 13, 1997
    Date of Patent: November 9, 1999
    Assignee: Morton International, Inc.
    Inventors: Thomas A. Koes, Grieg B. Beltramo
  • Patent number: 5958645
    Abstract: 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: Grant
    Filed: August 27, 1997
    Date of Patent: September 28, 1999
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Kouichi Hirose, Masahiro Akiyama, Katsumi Inomata, Yoshiji Yumoto
  • Patent number: 5948587
    Abstract: 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: Grant
    Filed: September 19, 1996
    Date of Patent: September 7, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Shiro Tan
  • Patent number: 5942368
    Abstract: 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: Grant
    Filed: April 22, 1997
    Date of Patent: August 24, 1999
    Assignee: Konica Corporation
    Inventors: Takeo Akiyama, Shinya Watanabe
  • Patent number: 5932389
    Abstract: 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: Grant
    Filed: February 20, 1998
    Date of Patent: August 3, 1999
    Assignee: Shipley Company, L.L.C.
    Inventor: Anthony Zampini
  • Patent number: 5912102
    Abstract: 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: Grant
    Filed: June 26, 1997
    Date of Patent: June 15, 1999
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shoji Kawata, Motofumi Kashiwagi, Teturyo Kusunoki, Masahiro Nakamura
  • Patent number: 5876895
    Abstract: 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: Grant
    Filed: May 24, 1996
    Date of Patent: March 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
  • Patent number: 5861229
    Abstract: 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: Grant
    Filed: September 22, 1992
    Date of Patent: January 19, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Osaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
  • Patent number: 5856058
    Abstract: 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: Grant
    Filed: June 7, 1996
    Date of Patent: January 5, 1999
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Kazuyuki Nitta, Akiyoshi Yamazaki, Yoshika Sakai, Toshimasa Nakayama
  • Patent number: 5853947
    Abstract: 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: Grant
    Filed: December 21, 1995
    Date of Patent: December 29, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, M. Dalil Rahman, Dinesh N. Khanna, Daniel P. Aubin, Sunit S. Dixit
  • Patent number: 5853949
    Abstract: 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 a
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: December 29, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Makoto Momota
  • Patent number: 5853948
    Abstract: 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: Grant
    Filed: October 29, 1997
    Date of Patent: December 29, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Atsushi Sawano, Junichi Mizuta, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5849457
    Abstract: 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: Grant
    Filed: October 24, 1997
    Date of Patent: December 15, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Katsuhiko Namba, Kaoru Tatekawa, Hiroshi Moriuma, Yasunori Uetani
  • Patent number: 5837417
    Abstract: 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: Grant
    Filed: December 30, 1994
    Date of Patent: November 17, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: M. Dalil Rahman, Dinesh N. Khanna, Daniel Aubin, Douglas McKenzie
  • Patent number: 5827634
    Abstract: 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: Grant
    Filed: March 12, 1997
    Date of Patent: October 27, 1998
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, Roger F. Sinta, Mark D. Denison, Sheri L. Ablaza
  • Patent number: 5807656
    Abstract: 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: Grant
    Filed: September 4, 1996
    Date of Patent: September 15, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Haruyoshi Osaki, Yasunori Uetani, Yoshiyuki Takata
  • Patent number: 5798201
    Abstract: 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: Grant
    Filed: July 2, 1997
    Date of Patent: August 25, 1998
    Assignees: Japan Synthetic Rubber Co., Ltd., Arakawa Chemical Industries, Ltd.
    Inventors: Katsumi Inomata, Nasahiro Akiyama, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5792585
    Abstract: 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: Grant
    Filed: March 25, 1994
    Date of Patent: August 11, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
  • Patent number: 5783355
    Abstract: 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: Grant
    Filed: June 14, 1995
    Date of Patent: July 21, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
  • Patent number: 5776652
    Abstract: 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: Grant
    Filed: October 14, 1997
    Date of Patent: July 7, 1998
    Assignee: Agfa-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5773200
    Abstract: 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: Grant
    Filed: December 15, 1995
    Date of Patent: June 30, 1998
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Satoshi Okazaki, Kazuhiro Nishikawa, Masaru Kobayashi, Miki Kobayashi, Mitsuo Umemura, Toshinobu Ishihara