Polymeric Mixture Patents (Class 430/192)
  • Patent number: 5206111
    Abstract: A silylated polymeric binder, which is soluble or swellable in alkali, bears a plurality of at least one of aliphatic and aromatic hydroxyl groups, at least a portion of which are derivatized by units of the formulae I and II:[(A--B.sub.n).sub.m C]--[(D.sub.o E.sub.p)BC].sub.u (I)and[(D.sub.o E.sub.p)BC].sub.v (II)which are side chains of the polymeric binder, whereinA denotes a silanyl group containing at least 2 silicon atoms in total linked to each other, but not more than 3 silicon atoms linked to each other in an unbranched chain of silicon atoms;B denotes a bridging group;C denotes a functional group which has formed a covalent bond with an aromatic, aliphatic, or cycloaliphatic hydroxyl group of the binder, the group D, or the group E;D denotes a grafted monohydric or polyhydric aliphatic alcohol;E denotes a grafted monohydric or polyhydric aromatic alcohol;n denotes 0 or 1;m denotes 1 or 2; ando, p, u and v each denote 0 or 1.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: April 27, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Wilharm, Gerhard Buhr, Juergen Fuchs
  • Patent number: 5202216
    Abstract: A positive working photosensitive composition comprising a polymeric compound insoluble in water but soluble in an aqueous alkaline solution and an aromatic sulfonic acid salt of an onium compound. The positive working photosensitive composition having high sensitivity and being capable of forming high-contrast images.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: April 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yoshimasa Aotani, Akira Umehara, Tsuguo Yamaoka
  • Patent number: 5202217
    Abstract: A positive resist composition comprising an aromatic group-containing alkali-soluble resin and a compound having an ammonium salt as skeleton, as the main components.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: April 13, 1993
    Assignee: Tosoh Corporation
    Inventors: Masaaki Todoko, Takashi Taniguchi, Toru Seita, Shinji Sato, Katuya Shibata
  • Patent number: 5202221
    Abstract: The present invention relates to a light-sensitive composition comprising (a) a photo-crosslinkable polymer having a maleimido group at a side chain and (b) a sensitizer such as the following compounds: ##STR1## The present invention provides a light-sensitive composition having very high sensitivity; providing excellent images during only a short exposure time; and being sensitive to light of long wave length.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: April 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masanori Imai, Noriaki Watanabe, Kouichi Kawamura
  • Patent number: 5200293
    Abstract: Positive-working photoresist compositions containing 23-27%, based on said composition, of at least one compound of formula (I) ##STR1## wherein one of the substituents X is hydrogen or a group of formula II ##STR2## and the other substituents X are a group of formula II; and 6-11%, based on said composition, of at least one polyhydroxy compound of formula III ##STR3## wherein X is a direct bond, --O--, --S--, --SO.sub.2 --, --CO-- or C(R.sub.6 (R.sub.7)--, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxy, and R.sub.6 and R.sub.7 are each independently of the other hydrogen, --CH.sub.3 or --CF.sub.3.These compositions have particularly good profile contrast and exhibit insignificant fluctuations in line width.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: April 6, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Reinhard Schulz, Horst Munzel, Ekkehard Bartmann
  • Patent number: 5200292
    Abstract: A light-sensitive composition is provided comprising (a) an aromatic diazo compound and (b) a cationic dye/borate anion complex.In a preferred embodiment, the cationic dye/anionic borate dye complex is represented by the general formula (I): ##STR1## wherein D.sup.+ represents a cationic dye; and R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, each represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted alkenyl group, an unsubstituted or substituted alkynyl group, an unsubstituted or substituted alicyclic group, or an unsubstituted or substituted heterocyclic group.The aromatic diazo compound can be a nonionic diazo compound.The light-sensitive compound can further comprise a radical-polymerizable unsaturated compound.
    Type: Grant
    Filed: January 17, 1990
    Date of Patent: April 6, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiaki Shinozaki, Junichi Fujimori
  • Patent number: 5198322
    Abstract: A positively operating radiation-sensitive mixture comprising a binder which is insoluble in water but soluble or at least swellable in aqueous alkaline solution, and as a photoactive component a polyfunctional .alpha.-diazo-.beta.-keto ester of the general formula I ##STR1## in which R.sup.1 denotes an aliphatic, cycloaliphatic or araliphatic or aromatic radical having 4 to 20 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by ##STR2## or NH groups and/or contain keto groups, X denotes an aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by the groups --NR.sup.2 --, --C(O)--O--, --C(O)--NR.sup.2 --, --C(O)-- ##STR3## --NR.sup.2 --C(O)--NR.sup.3 --, --O--C(O)--NR.sup.2 --, --C(O)-- ##STR4## or --O--C(O)--O--, or CH groups can be replaced by ##STR5## in which R.sup.2 and R.sup.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: March 30, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Wilharm, Hans-Joachim Merrem, Georg Pawlowski, Ralph Dammel
  • Patent number: 5196517
    Abstract: A trihydroxybenzophenone compound of the formula (I): ##STR1## wherein R.sub.1 is selected from the group consisting of hydroxyl group, halide group, a lower alkyl group having 1 to 4 carbon atoms, and a lower alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: March 23, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Medhat A. Toukhy, Alfred T. Jeffries, III
  • Patent number: 5196289
    Abstract: Block phenolic oligomers of the formula (I): ##STR1## These may be reacted alone or with selected phenolic monomers during or after the formation of a phenolic novolak resin thereby said resin having at least one unit of formula (II): ##STR2##
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: March 23, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5188921
    Abstract: A block copolymer novolak resin composition comprising at least one unit of the reaction product of an alkali-soluble phenolic moiety having at least two phenolic nuclei and at least two unsubstituted positions ortho and para to the hydroxyls in the moiety and a reactive ortho, ortho bonded oligomer having the formula: ##STR1## wherein x is from 2 to 7; wherein R is selected from hydrogen a lower alkyl group or lower alkoxy group having 1-4 carbon atoms and a halogen group; and Y.sub.1 is either a hydroxyl group; an alkoxy group or a halogen group; and Y.sub.2 is hydrogen, alkyl, alkoxy, halogen, hydroxyl, --CH.sub.2 OH, --CH.sub.2 -- halogen, or --CH.sub.2 -alkoxy group.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: February 23, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Kenji Honda, Andrew J. Blakeney, Sobhy Tadros
  • Patent number: 5188920
    Abstract: A positive resist composition comprising a radiation-sensitive component and an alkali-soluble resin and a phenol compound of the formula: ##STR1## wherein R is a hydrogen atom, a lower alkyl group or a phenyl group, R' is an alkyl group or an alkoxy group, and n is a number of 0 to 3, which has well balanced good properties such as sensitivity, resolution, heat resistance and adhesiveness.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: February 23, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Moriuma, Haruyoshi Osaki, Takeshi Hioki, Yasunori Uetani
  • Patent number: 5183722
    Abstract: A positive photosensitive composition for forming lenses, which comprises a polymer, a photosensitive agent, a thermosetting agent and a solvent, wherein said polymer is an alkali-soluble resin, said photosensitive agent is a 1,2-naphthoquinone diazide sulfonate, and said thermosetting agent is a thermosetting agent capable of imparting heat resistance and solvent resistance at the time of forming lenses by heat treatment.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: February 2, 1993
    Assignee: Tosoh Corporation
    Inventors: Yoshitaka Tsutsumi, Teruhisa Uemura, Masazumi Hasegawa
  • Patent number: 5182185
    Abstract: Photosensitizers containing saturated and unsaturated polycyclic compounds containing the cyclopentane-2-diazo-1,3-dione structural unit.These compounds have their maximum u.v. absorption at around 248 nm, decompose into polar products upon irradiation, and can be used as photosensitizers in positive deep u.v. or excimer laser (248 nm) lithography. They are most preferably useful with deep u.v. transparent resins for forming photoresists.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: January 26, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Chengjiu Wu, Anne Mooring, James T. Yardley
  • Patent number: 5182183
    Abstract: A positive photosensitive planographic printing plate is disclosed which has a photosensitive layer comprising in combination a specific o-naphthoquinonediazidosulfonic ester and a resin having a specific structural unit(s). Said photosensitive layer may also contain a novolak resin and/or an organic acid.
    Type: Grant
    Filed: November 8, 1991
    Date of Patent: January 26, 1993
    Assignees: Mitsubishi Kasei Corporation, Konica Corporation
    Inventors: Hiroshi Tomiyasu, Yoshiko Kobayashi, Kiyoshi Goto, Takeshi Yamamoto, Hideyuki Nakai
  • Patent number: 5182184
    Abstract: Novolak resins are provided which are the condensation product of (a) a phenol, phenol derivative, or mixtures thereof, and (b) a mixture of formaldehyde or a formaldehyde precursor and (1) a monohydroxy aromatic aldehyde and wherein at least a portion of the hydroxyl groups thereof are esterified or (2) a mixture of at least one monohydroxy aromatic aldehyde and at least one non-hydroxylic aromatic aldehyde; the novolak resins having a hydroxyl number of from about 120 to about 180 grams of resin per equivalent of hydroxyl. The novolak resins are especially useful in positive photoresist formulations and have enhanced photospeed and film loss characteristics as well as improved thermal stability.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: January 26, 1993
    Assignee: Morton International, Inc.
    Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
  • Patent number: 5178986
    Abstract: A radiation sensitive oligomeric compound is described as the photoactive component with a base soluble phenolic matrix resin to provide improved photo-resist composition having high light-sensitivity, high resolution, excellent developer resistance and excellent resistance to thermal flow.
    Type: Grant
    Filed: June 19, 1992
    Date of Patent: January 12, 1993
    Assignee: Shipley Company Inc.
    Inventors: Anthony Zampini, David C. Madoux, Peter Trefonas, III, Charles R. Szmanda
  • Patent number: 5177172
    Abstract: A methylol-substituted trihydroxybenzophenone of the formula (I): ##STR1## This methylol-substituted trihydroxybenzophenone may be reacted with selected phenolic monomers during or after the formation of a phenolic novolak resin thereby said resin having at least one unit of formula (II): ##STR2## wherein R and R.sub.1 are individually selected from hydrogen, a lower alkyl group having 1 to 4 carbon atoms or a lower alkoxy group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: February 13, 1991
    Date of Patent: January 5, 1993
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5175078
    Abstract: A positive type photoresist developer which comprises an aqueous solution of quaternary ammonium hydroxide represented by the general formula; ##STR1## (wherein all the symbols are as defined in the appended claims) and hydrazine or hydrazine and a nonionic surfactant is disclosed.The developer can form a fine pattern having a high degree of resolution and can provide an excellent profile with few irregularities in pattern dimensions.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: December 29, 1992
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tetsuo Aoyama, Susumu Kaneko
  • Patent number: 5173393
    Abstract: A photoresist system that is easily structurable and, in particular, is suitable for the deep ultraviolet range is provided. An increased etching resistance to a halogen-containing plasma is produced in a lithographically generated photoresist structure by treatment with a reactant. The reactant comprises predominantly aromatic structures and includes reactive groups that are suitable for chemical reaction with further reactable groups of the photoresist. In an embodiment, the photoresist includes anhydride or epoxy groups that are suitable for structuring with deep ultraviolet light.
    Type: Grant
    Filed: April 24, 1990
    Date of Patent: December 22, 1992
    Assignee: Siemens Aktiengesellschaft
    Inventors: Recai Sezi, Michael Sebald, Rainer Leuschner, Siegfried Birkle, Hellmut Ahne
  • Patent number: 5173390
    Abstract: A water soluble contrast enhancement compound and composition, and a method of use thereof, are disclosed for improving sidewall profiles in photoresist patterning and developing. The compound consists of a 1-oxy-2-diazonaphthalene sulfonamide salt.
    Type: Grant
    Filed: September 13, 1990
    Date of Patent: December 22, 1992
    Assignee: Texas Instruments Incorporated
    Inventors: John B. Covington, Vic B. Marriott, Larry G. Venable, Peter Kim
  • Patent number: 5173389
    Abstract: A positive-working photoresist composition is disclosed, which comprises (1) a light-sensitive material obtained by reacting a polyhydroxy compound containing at least one group represented by the following general formula (I) per molecule with at least one of 1,2-naphthoquinonediazido-5-sulfonyl chloride and 1,2-naphthoquinonediazido-4-sulfonyl chloride, and (2) an alkali-soluble novolak resin: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a C.sub.1 -C.sub.4 straight or branched alkyl or alkoxy group, provided that R.sub.1 and R.sub.2 do not represent hydrogen atoms at the same time; and X represents a divalent organic group.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: December 22, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Shinji Sakaguchi, Tadayoshi Kokubo
  • Patent number: 5171656
    Abstract: Photosensitive compositions comprising a polymer and a photoactive constituent, which are able to be developed with aqueous, alkaline agents exhibit good bleaching properties in the DUV range, whereby the photoactive constituent has good solubility-inhibiting properties and does not evaporate during the drying process, when the photoactive constituent comprises diazo tetronic acid or a diazo tetronic acid derivative of the following structure: ##STR1## where the residues R are the same or different and signify H, alkyl, cycloalkyl, aryl or a silicon-containing residue.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: December 15, 1992
    Assignee: Siemens Aktiengesellschaft
    Inventors: Michael Sebald, Juergen Beck, Rainer Leuschner, Recai Sezi, Hans J. Bestmann
  • Patent number: 5169740
    Abstract: Resist containing novolak prepared by condensating halogenated phenol represented by the following formula (III) and one or more phenol derivatives selected from the group consisting of cresol, xylenol, tet-butylphenol and propenylphenol, with a carbonyl compound ##STR1## wherein R.sub.3 is an halogen atom selected from the group consisting of F, Cl, and Br. If the resist is used as a positive-type one, it further contains a photo-sensitive agent, and R.sub.3 in the formula (III) is either F or Br. If the resist is used as a negative-type one, it further contains a photosensitive agent and/or a sensitizer, and R.sub.3 in the formula (III) is either Cl or Br.
    Type: Grant
    Filed: March 29, 1990
    Date of Patent: December 8, 1992
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Toru Ushirogouchi, Tsukasa Tada, Akitoshi Kumagae
  • Patent number: 5168030
    Abstract: Disclosed herein is an antistatic photo-resist containing an antistatic agent. Since antistatic photo-resist according to the present invention is hardly charged, it can be suitably used as a mask in implanting ions into semiconductor substrate.
    Type: Grant
    Filed: August 5, 1991
    Date of Patent: December 1, 1992
    Assignees: Mitsubishi Denki Kabushiki Kaisha, Mitsubishi Kasei Corporation
    Inventors: Konoe Miura, Tameichi Ochiai, Yasuhiro Kameyama, Tooru Koyama, Takashi Okabe, Tomoharu Mametani
  • Patent number: 5166033
    Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and the quinonediazide sulfonate of at least one phenolic compound selected from vinylphenol compounds and isopropenylphenol compounds as a photosensitive agent. It is suitable for use in minute processing.
    Type: Grant
    Filed: September 25, 1990
    Date of Patent: November 24, 1992
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada
  • Patent number: 5166036
    Abstract: The invention provides an aqueous electrodeposition coating composition for a positive working resist and an image-forming method using the same. The coating composition is very stable under storage conditions and is capable of resulting in a positive working resist which is specifically useful in the preparation of a printed circuit board with mini-via-holes.
    Type: Grant
    Filed: July 9, 1991
    Date of Patent: November 24, 1992
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mamoru Seio, Takeshi Ikeda, Kanji Nishijima, Katsukiyo Ishikawa
  • Patent number: 5164279
    Abstract: This invention provides improved positive photoresist compositions containing a bis(azophenyl)resorcinol as a dye.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: November 17, 1992
    Assignee: Shipley Company Inc.
    Inventors: Peter Trefonas, III, Anthony Zampini, David C. Madoux
  • Patent number: 5162190
    Abstract: A compound of the general formula I ##STR1## in which D denotes a 1,2-naphthoquinone-2-diazide-4-sulfonyl or - 5-sulfonyl radical,R.sup.1 denotes an alkylene group andR.sup.2 denotes a hydrogen atom, an alkyl group or a group R.sup.1 --OH,or of the general formula II ##STR2## in which X denotes an alkylene group, an arylene group or a group of the formulaNH--Y--NH,wherein Y is an alkylene group or an arylene group,R.sup.3 denotes an alkylene group, which may be interrupted by ether oxygen atoms,n is a number from 1 to 40 andm is a number from 0 to 50,the ratio m:(m+n) being from 0:100 to 95:100 and R.sup.1 and D having the above-indicated meaning, are disclosed. The compounds may be used in positive-working photosenitive materials for the production of printing plates and photoresists. Compounds according to formula II do not require an addition of polymeric binders.
    Type: Grant
    Filed: June 29, 1989
    Date of Patent: November 10, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Zahn, Gerhard Buhr, Hartmut Steppan
  • Patent number: 5162510
    Abstract: The invention relates to new mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitizer compositions exhibit excellent solution stability and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: November 10, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Robert E. Potvin, Jonas O. St. Alban, Chester J. Sobodacha
  • Patent number: 5158855
    Abstract: An .alpha.-diazoacetoacetic acid ester derived from cholic acid, deoxycholic acid, lithocholic acid or a derivative thereof is effective as a sensitizer in a photosensitive resin composition containing an alkali-soluble resin to form a resist for lithography using KrF excimer laser.
    Type: Grant
    Filed: September 22, 1988
    Date of Patent: October 27, 1992
    Assignee: Hitachi, Ltd.
    Inventors: Hisashi Sugiyama, Kazuo Nate, Akiko Mizushima, Keisuke Ebata
  • Patent number: 5158854
    Abstract: Present invention provides a photosensitive and high energy beam sensitive resin composition which may be used as a resist material for forming both of the positive and negative patterns. The resin composition comprises: a substituted polysiloxane having the main polysiloxane chain and a substituent hydrophilic group or groups; and a solvent for the substituted polysiloxane. The substituted polysiloxane used in preferred embodiments of the invention are produced by acylating polysiloxanes including polydiphenylsiloxane and polyphenylsilsesquioxane to introduce acyl groups, followed by oxidation of the thus introduced acyl groups to convert them into carboxyl groups or by reducing the thus introduced acyl groups to convert them into alpha-hydroxyalkyl groups. The acyl, carboxyl or alpha-hydroxyalkyl groups are further substituted to obtain substituted polysiloxanes which are soluble in an aqueous alkali.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: October 27, 1992
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Saburo Imamura, Akinobu Tanaka, Katsuhide Onose
  • Patent number: 5157018
    Abstract: Polymers comprising perfluoroalkyl groups, reproduction layers containing these polymers and use thereof for waterless offset printing. The novel perfluoroalkyl group-containing polymers comprise polymers or polycondensates and have, in each case as substituents on different carbon atoms of benzene rings, phenolic OH groups and perfluoroalkyl groups which are optionally attached through intermediate members. In particular, at least 10% of the polymer units carry perfluoroalkyl groups. These polymers are either formed by condensation of substituted phenols (e.g., 4-hydroxybenzoic acid-perfluoroalkyl ester) with an aldehyde, a ketone, or a reactive bismethylene compound or by reacting polymers containing phenolic OH groups (e.g., hydroxypolystyrene) or polycondensates containing reactive OH groups (e.g., phenol-formaldehyde resins) with a perfluoroalkyl group-containing compound (e.g., 2,2-dihydroperfluorodecanoic acid chloride).
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: October 20, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Werner H. Muller
  • Patent number: 5153096
    Abstract: A positive type photoresist composition comprising at least one light-sensitive material, as defined herein, and an alkali-soluble novolak resin, has a high resolving power, particularly when used in semiconductor devices, accurately reproduces mask dimensions over a wide photomask line width range, from a resist pattern in a cross-sectional form having a high aspect ratio in a pattern having a line width of no greater than 1 .mu.m, has a wide developing latitude and excellent heat resistance.
    Type: Grant
    Filed: March 18, 1991
    Date of Patent: October 6, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5151339
    Abstract: Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: September 29, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Thomas R. Sarubbi
  • Patent number: 5151340
    Abstract: A photoactive compound having formula (I): ##STR1## wherein R is selected from the group consisting of hydrogen or a lower alkyl group having 1-4 carbon atoms and each D is individually selected from the group consisting of a hydrogen or photoactive o-quinonediazide sulfonyl group; subject to the proviso that at least two of the four D's in formula (I) are photoactive o-naphthoquinonediazide sulfonyl moieties.
    Type: Grant
    Filed: July 2, 1990
    Date of Patent: September 29, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Sobhy Tadros
  • Patent number: 5149614
    Abstract: A developer composition for presensitized plates for use in making lithographic printing plates comprises water, an alkali silicate and at least one compound having at least one aryl group, at least one oxyalkylene group and at least one sulfate ester group or sulfonic acid group. The composition is excellent in developing stability and processability. It is less foamable and seldom generates deposits even when it is deteriorated. Moreover, the composition makes it possible to develop both positive- and negative-working PS plates.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: September 22, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiji Akiyama, Hiroshi Misu
  • Patent number: 5145763
    Abstract: A positive photoresist composition containing (i) a quinone diazide polymer formed by reacting a cresol-formaldehyde novolac resin and an o-quinonediazide compound, and (ii) a sulfonamide development enhancement agent.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: September 8, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: David R. Bassett, Gary A. Amstutz
  • Patent number: 5143814
    Abstract: The invention provides a method for producing a positive working photosensitive element with increased photospeed which comprises coating a formulation containing at least one novolak or polyvinyl phenol resin, at least one o-quinone diazide and a propylene glycol alkyl ether acetate on a substrate, drying, exposing to imaging energy and developing.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: September 1, 1992
    Assignee: Hoechst Celanese Corporation
    Inventor: Thomas R. Pampalone
  • Patent number: 5143815
    Abstract: A light-sensitive mixture is disclosed which contains a 1,2-naphthoquinone-2-diazide-sulfonic acid ester and a binder. A reproduction material produced with this mixture is also disclosed. The naphthoquinone-diazide-sulfonic acid ester is a compound of the general formula I ##STR1## in which D is a 1,2-naphthoquinone-2-diazide-4-sulfonyl or 1,2-naphthoquinone-2-diazide-5-sulfonyl radical,R.sub.1 is hydrogen or an -OD group, andR.sub.2 is alkyl or substituted or unsubstituted aryl, preferably alkyl having 1 to 10 carbon atoms or substituted or unsubstituted phenyl.The light-sensitive mixture is highly photosensitive, has good overdevelopment resistance and is resistant to fountain solutions and petroleum hydrocarbons.
    Type: Grant
    Filed: August 24, 1988
    Date of Patent: September 1, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 5143816
    Abstract: A light-sensitive composition comprising:(a) a polysiloxane compound having at least 1 mol % of a structural unit derived from a product of a thermal cycloaddition reaction between a compound of formula (I), (II), (III) or (IV) and a compound of formula (V), (VI), (VII) or (VIII), and(b) an orthoquinonediazide compound.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: September 1, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Toshiaki Aoai
  • Patent number: 5141838
    Abstract: A photosensitive composition is described, wherein it comprises a high-molecular compound having sulfonamide group to be insoluble in water, but soluble in an aqueous alkaline solution and a positive working photosensitive compound. The photosensitive composition is excellent in coatability and in developability when the composition is used for photosensitive lithographic printing plates.
    Type: Grant
    Filed: February 24, 1989
    Date of Patent: August 25, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keitaro Aoshima, Akira Nagashima
  • Patent number: 5134054
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising(A) a photosensitive compound having a molecular weight of less than 6,000 and containing at least one modified quinonediazidesulfone units represented by the following formula (I) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group or an alkylene ether group,in the molecule and(B) an acrylic resin having a salt-forming group.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: July 28, 1992
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5132376
    Abstract: Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: July 21, 1992
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Thomas R. Sarubbi
  • Patent number: 5130225
    Abstract: A positive resist composition comprising an alkali-soluble resin, a quinone diazide compound and a specific hydroxyl group-containing compound can improve sensitivity without deterioration of heat resistance and film thickness retention.
    Type: Grant
    Filed: May 6, 1991
    Date of Patent: July 14, 1992
    Assignee: Sumitomo Chemical Co. Ltd.
    Inventor: Yasunori Uetani
  • Patent number: 5130224
    Abstract: A positive-working photoresist composition is disclosed comprising an alkali-soluble resin and a 1,2-naphthoquinonediazido group-containing compound, and further contains at least one light absorber selected from the group consisting of the azo compounds represented by the following formulae (I), (II), (III), (IV), (V) and (VI) in a proportion of from about 0.1 to about 10% by weight based on the total solid content of the photoresist composition, and is useful for forming a fine pattern of excellent quality even on a substrate with unevenness or high reflectivity: ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group; and X represents a sulfur atom or an oxygen atom; ##STR2## wherein R.sub.2 represents a hydroxyl group or a di(lower alkyl)amino group; R.sub.3 and R.sub.4 each represents a hydrogen atom or a carboxyl group, provided that at least one of R.sub.3 and R.sub.4 represents a carboxyl group; and R.sub.
    Type: Grant
    Filed: February 28, 1990
    Date of Patent: July 14, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5130409
    Abstract: Novolak resins are provided which are the condensation product of (a) a phenol, phenol derivative, or mixtures thereof, and (b) a mixture of formaldehyde or a formaldehyde precursor and an aromatic aldehyde. When the aromatic aldehyde is a monohydroxy aromatic aldehyde, the novolak resin is especially useful in positive photoresist formulations.
    Type: Grant
    Filed: November 16, 1990
    Date of Patent: July 14, 1992
    Assignee: Morton International, Inc.
    Inventors: Richard M. Lazarus, Randall Kautz, Sunit S. Dixit
  • Patent number: 5128230
    Abstract: This invention is directed to novel photoresist processes and compositions having high resolution novalac resins, high resolution photoactive components with several diazoquinone groups per molecule, and solvents having a high solvency power, better safety, improved photospeed, higher contrast and equivalent cast film thickness from lower percent solids formulations.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: July 7, 1992
    Assignee: Shipley Company Inc.
    Inventors: Michael K. Templeton, Anthony Zampini, Peter Trefonas, III, James C. Woodbrey, David C. Madoux, Brian K. Daniels
  • Patent number: 5128232
    Abstract: A photoresist that utilizes a copolymer of a phenol and a cyclic alcohol having increased optical transmission properties relative to photoresists using fully aromatic phenolic resins. Preferred binders are hydrogenated novolak resins and hydrogenated polyvinyl phenol resins.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: July 7, 1992
    Assignee: Shiply Company Inc.
    Inventors: James Thackeray, George W. Orsula, Roger Sinta
  • Patent number: 5124228
    Abstract: A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I) or (II): ##STR1## wherein a, c and d are the same or different and a number of 0 to 3, provided that when a is 0 or 3, b is a number of 0 to 3 or when a is 1 or 2, b is 0, 1 or 2, and a+b and c+d are not less than 2; R and R' are the same or different and an alkyl group or an aryl group provides a positive resist composition having a high .gamma.-value.
    Type: Grant
    Filed: July 18, 1989
    Date of Patent: June 23, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Yasunori Uetani, Makoto Hanabata, Hirotoshi Nakanishi, Koji Kuwana, Fumio Oi
  • Patent number: 5116715
    Abstract: A photosensitive composition having increased contrast and selectivity, useful in forming high resolution patterns. The composition comprises a phenolic resin, a diazoquinone compound and an aromatic fused polycyclic sulfonic or carboxylic acid, in the form of the free acid and/or an ammonium salt and/or an acid halide, the cation component of the ammonium salt having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, each represent hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl.In forming a negative pattern, the composition is coated on a substrate and exposed imagewise to ultraviolet radiation, thereafter treated with a silicon compound, whereby the silicon compound is selectively absorbed into the irradiated portions and the nonirradiated portions are then removed by dry etching.
    Type: Grant
    Filed: March 8, 1991
    Date of Patent: May 26, 1992
    Assignee: U C B S.A.
    Inventors: Bruno Roland, Jan Vandendriessche, Catherine Jakus