Quinone Diazide Containing Patents (Class 430/189)
  • Patent number: 5340684
    Abstract: A photosensitive composition contains a polyimide constituted by a repeating unit having a hydroxyl group and a repeating unit having a siloxane bond, or a repeating unit having a hydroxyl group, a repeating unit having a siloxane bond, and a repeating unit other than these two repeating units, and a photosensitive agent consisting of an ester compound or an amide-ester compound of naphthoquinonediazidesulfonic acid or benzoquinonediazidesulfonic acid. The photosensitive composition is used as a passivation film of a semiconductor device or a photoresist.
    Type: Grant
    Filed: November 29, 1993
    Date of Patent: August 23, 1994
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Rumiko Hayase, Masayuki Oba, Naoko Kihara, Yukihiro Mikogami
  • Patent number: 5338641
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.,.alpha.-bis(sulfonyl)diazomethane, which forms a strong acid on irradiation, of the general formula ##STR1## in which R is an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound having at least one C--O--C or C--O--Si--bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert
  • Patent number: 5332650
    Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5 which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.
    Type: Grant
    Filed: September 4, 1992
    Date of Patent: July 26, 1994
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5308744
    Abstract: A new photoacid generator having the formula ##STR1## wherein R=hydrogen, hydroxyl, or the --O--S(.dbd.O).sub.2 --Q moiety;R.sup.1 =CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.2 =CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.3 =lower alkyl or hydrogen;R.sup.4 =hydrogen, --CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ;R.sup.5 =hydrogen, --CH.sub.2 OS(.dbd.O).sub.2 --Q, or --NO.sub.2 ; andQ is a diazonaphthoquinone moiety; with the proviso that R.sup.3 is lower alkyl when R.sup.2 and R.sup.4 are NO.sub.2, and with the proviso that R.sup.1 .noteq.R.sup.2 and R.sup.4 .noteq.R.sup.5.exhibits unprecedented sensitivity to actinic radiation. This compound is photochemically transformed from a non-acidic entity to photoproducts which contain both sulfonic and carboxylic acid functuional groups. The acid generator is effective with polymers having acid labile groups, converting them into alkaline-soluble polymers, and with polymers which do not have such acid labile groups.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: May 3, 1994
    Assignee: Morton International, Inc.
    Inventor: Thomas A. Koes
  • Patent number: 5290656
    Abstract: A quinone diazide sulfonic acid ester of a phenol compound of the general formula (I): ##STR1## wherein Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 are the same or different and each a hydrogen atom, an alkyl group, a halogen atom or a hydroxyl group, provided that at least one of Y.sub.1, Y.sub.2, Y.sub.3 and Y.sub.4 is a hydroxyl group; Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 are the same or different and each a hydrogen atom, an alkyl, an aryl group, a halogen atom or a hydroxyl group, provided that at least one of Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5 and Z.sub.6 is a hydroxyl group; X is ##STR2## in which R.sub.1 and R.sub.2 are the same or different and each a hydrogen atom, an alkyl group, an alkenyl group, a cyclo-alkyl group, an alkoxy group or an aryl group, provided that when at least one of R.sub.1 and R.sub.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: March 1, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Makoto Hanabata, Hirotoshi Nakanishi, Koji Kuwana, Yukio Hanamoto, Fumio Oi, Jun Tomioka
  • Patent number: 5256517
    Abstract: A positive-working radiation-sensitive mixture is described which essentially contains a photoactive component and a water-insoluble binder which is soluble, or at least swellable, in aqueous alkaline solution, wherein a compound is used, as photoactive component, which contains .alpha.-diazo-.beta.-keto ester units and sulfonate units of the formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are an unsubstituted or substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical having 4 to 20 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by N or NH groups and/or contain keto groups,X is an unsubstituted or substituted aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, it being possible for individual CH.sub.2 groups to be replaced by oxygen or sulfur atoms or by the groups --NR.sup.3 --, --C(O)--0--, --C(O)--NR.sup.3 --, ##STR2## --NR.sup.3 --C(O)--NR.sup.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: October 26, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Georg Pawlowski, Hans-Joachim Merrem, Ralph Dammel, Walter Spiess
  • Patent number: 5250669
    Abstract: Photosensitive compounds having preferably a functional group such as --SO.sub.2 Cl, --SO.sub.3 H, --SO.sub.3 R, ##STR1## (R, R', R" being alkyl) on a terminal benzene or naphthalene ring connected via a methylene group and ##STR2## moiety are improved in sensitivity to light and thermal stability, and thus useful in a photo resist.
    Type: Grant
    Filed: April 23, 1992
    Date of Patent: October 5, 1993
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Kazufumi Ogawa, Masayuki Endo, Keiji Ohno, Mamoru Nagoya
  • Patent number: 5227473
    Abstract: A quinone diazide of formula (I) or formula (II):(S)l--(L.sup.1)m=-(Q).sub.n (I)--(L.sup.2 (-S))o-(L.sup.3 (--Q))p- (II)wherein S is a light absorbing portion having an absorption coefficient of greater than 1000 in wavelengths longer than 360 nm; Q is a quinone diazide residue; L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and Q, provided, however, that L.sup.1, L.sup.2 and L.sup.3 do not conjugate S and Q; l, m, n, o and p are integers; andwherein the emission intensity of the compound of formulas (I) and (II) is smaller than the emission intensity of the chromophoric group alone. Also disclosed is a light sensitive composition comprising an alkali soluble resin and the above quinone diazide compound. The quinone diazide compound of the present invention have spectral sensitization with respect to visible light and are useful in visible light projection plates and as visible laser sensing materials.
    Type: Grant
    Filed: May 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Satoshi Takita
  • Patent number: 5212042
    Abstract: A positive type light-sensitive composition is disclosed, comprising an alkali-soluble high-molecular binder and at least one p-iminoquinonediazido-N-sulfonyl compound. This composition can be used for forming a resist for an IC board, a printing plate, a silver-free, image-forming material, etc.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: May 18, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumiaki Shinozaki, Akira Umehara, Sadao Ishige
  • 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: 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: 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: 5169741
    Abstract: The present invention provides a method for forming resist patterns for exposure to a KrF excimer laser of 248.4 nm. The method includes supplying a pattern-forming material containing a photosensitive compound having a diazo group as a photosensitive group, an alkaline soluble polymer, and a solvent capable of solving the photosensitive compound and the polymer, with the pattern-forming material being adapted to a pH of 4 or less, onto a substrate to form a film. The pattern-forming material applied on the substrate is exposed to a light of about 248.4 nm. The exposed pattern-forming material is developed with an alkaline developing solution. The pattern-forming material contains a compound capable of releasing an acid when exposed to light of about 248.4 nm. The substrate is baked between the exposure and developing steps. The compound capable of releasing the acid is selected from an onium salt and a nitrobenzyl tosylate compound.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: December 8, 1992
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Yoshiyuki Tani, Masayuki Endo
  • 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: 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: 5094936
    Abstract: A process for silylation of positive or negative photosensitive resist layer on a semiconductor wafer after the resist layer has been exposed to radiant energy through a mask which includes introducing a silylating agent to the wafer at high pressure over 760 torr and, usually, at temperatures less than 180.degree. C. Increased pressure increases the rate of silylation, allows practical use of lower process temperatures, and, therefore, allows better process control. Also an apparatus is disclosed for applying the high pressure silylation process to a wafer.
    Type: Grant
    Filed: June 26, 1990
    Date of Patent: March 10, 1992
    Assignee: Texas Instruments Incorporated
    Inventors: George R. Misium, Cesar M. Garza, Cecil J. Davis
  • Patent number: 5075193
    Abstract: The invention relates to desensitized quinone diazide compounds for use as photoactive components in radiation-sensitive compositions, such as, especially, photoresists, which compounds contain microcrystalline cellulose as desensitizing agent.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: December 24, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Stefan Dresely, Ditmar Raulin
  • Patent number: 5024921
    Abstract: A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-napthoquinone diazide sensitizers) to prepare a light-sensitive composition useful in a method for forming a positive photoresist image.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: June 18, 1991
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Alfred T. Jeffries, III, Thomas R. Sarubbi
  • Patent number: 5011753
    Abstract: Heat resistant, shapable, hydroxy and/or alkoxy-substituted polyamides derived from at least one diamine selected from unsubstituted and substituted 4,4'-bis[2-(4-amino-3-hydroxyphenyl)hexafluoroisopropyl)]diphenyl ether 4,4'-bis-[2-(3-amino-4-hydroxyphenyl)hexafluoroisopropyl]diphenyl ether and a dicarboxylic acid or a derivative thereof e.g. its acid halo or ester. The polyamides of the invention may be thermally cured to form polybenzoxazoles of higher heat resistance which are stable to hydrolytic, chemical and radiation attack.The polyamides of the invention may be formed into shaped articles by molding, extrusion and solvent casting processes preferably in the presence of a solvent or diluent and then optionally converted into heat resistant, insoluble polybenzoxazoles. These shaped articles are useful in aircraft, electronic and other commercial applications where heat, chemical and radiation resistance are desired in conjunction with good mechanical and electrical properties.
    Type: Grant
    Filed: February 7, 1990
    Date of Patent: April 30, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Werner H. Mueller, Dinesh N. Khanna
  • Patent number: 4996301
    Abstract: Polyfunctional .alpha.-diazo-.beta.-keto esters of the general formula I are described ##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 N-- 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 ##STR2## in which R.sup.2 and R.sup.3 independently of one another represent hydrogen or an aliphatic, carbocyclic or araliphatic radical,m denotes an integer from 2 to 10 andn denotes an integer from 0 to 2,whereinm-n is .gtoreq.2.The compounds mentioned are used as photoactive components in radiation-sensitive mixtures.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Wilharm, Hans-Joachim Merrem, Georg Pawlowski
  • Patent number: 4959293
    Abstract: 2-diazo-1-ones are useful deep UV photoresist solubility modification agents exhibiting improved photosensitivity allowing shorter deep UV exposure times to achieve the same extent of photoreaction as with prior art solubility modification agents. The 2-diazo-1-one solubility modification agents when used as photoactive solubility modification components in photoresist compositions permit the photoresist compositions to act as either positive or negative photoresist compositions depending upon the developer employed, namely, as a positive resist when a metal ion containing developer is employed and as a negative resist when a metal ion free developer is employed.
    Type: Grant
    Filed: October 28, 1988
    Date of Patent: September 25, 1990
    Assignee: J. T. Baker, Inc.
    Inventors: George Schwartzkopf, John B. Covington, Kathleen B. Gabriel
  • Patent number: 4880724
    Abstract: Disclosed is a method for the manufacture of a lithographic printing plate where a photosensitive lithographic printing plate precursor is imagewise exposed, a determined about of a developer is supplied to the exposed surface and the developer is the disposed of. A surfactant is added to the developer so that the surface tension of the developer is about 50 dyne/cm or less at 25.degree. C. By the addition of the surfactant, a stable and economical development of an exposed plate is possible with a small amount of the surfactant-containing developer.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: November 14, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tadao Toyama, Hisao Ohba, Kenji Kunichika
  • Patent number: 4880722
    Abstract: The dissolution rate in alkaline developer solutions of image-wise exposed photoresist systems based on diazoquinone sensitized polyamic acid is reduced to prepare relief images of fine line resolution by reducing the acidity of the polyamic acid prior to exposure.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: November 14, 1989
    Assignee: International Business Machines Corporation
    Inventors: Wayne M. Moreau, Kaolin N. Chiong
  • Patent number: 4871644
    Abstract: Photoresist compositions which operate positively and contain at least one ocmpound of the formula I ##STR1## in which X is --C.sub.n H.sub.2n --, --O--, --S-- or --C(O)--, n being a number from 1 to 6. These compositions are particularly suitable for use as positively-operating copying lacquers.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4857435
    Abstract: Actinic (deep ultraviolet, ultraviolet and visible) light sensitive positive photoresist compositions containing a mixture of an alkali-insoluble photoactive compound capable of being transformed into an alkali-soluble species upon exposure to actinic radiation, in an amount sufficient to render the mixture relatively alkali insoluble and a polymer comprising an amount of --CO--NH--CO-- groups, such as maleimide and especially maleimide-substituted styrene copolymers, sufficient to render the mixture readily alkali soluble upon exposure to actinic radiation are disclosed. The preferred copolymers include maleimide/styrene or .alpha.-methylstyrene in a 1:1 molar ratio. The preferred photoactive compound suitable for a positive photoresist composition responsive to deep UV actinic radiation has the formula 18-B in Table I. The present invention also contemplates photosensitive elements and thermally stable photochemically imaged systems based on the actinic light sensitive positive photoresist compositions.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: August 15, 1989
    Assignee: Hoechst Celanese Corporation
    Inventors: Frederick R. Hopf, Michael J. McFarland, Christopher E. Osuch
  • Patent number: 4853314
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C-O-C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: August 1, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher
  • Patent number: 4837121
    Abstract: A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers ) to prepare a light-sensitive composition useful as a positive-working photoresist.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: June 6, 1989
    Assignee: Olin Hunt Specialty Products Inc.
    Inventors: Andrew J. Blakeney, Alfred T. Jeffries, III, Thomas R. Sarubbi
  • Patent number: 4835085
    Abstract: Compounds of the general formula (I) or (II) ##STR1## in which R is 1,2-naphthoquinone-2-diazide-4- or -5-sulfonyl and X is a straight-chain or branched C.sub.1 -C.sub.12 -alkylene group, which is unsubstituted or mono- or disubstituted by OH group or is --CH.dbd.CH--, are suitable as the light-sensitive component in photoresist materials. Both positive and negative images can be prepared with light-sensitive mixtures containing these compounds and a binder.
    Type: Grant
    Filed: October 7, 1987
    Date of Patent: May 30, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4812551
    Abstract: A novolak resin for a positive photoresist is provided herein, which resin is produced by the addition condensation reaction of a phenol with formaldehyde. This novolak resin has improved heat resistant and sensitivity properties and the thickness retention of the novolak resins are very high.
    Type: Grant
    Filed: November 9, 1987
    Date of Patent: March 14, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Fumio Oi, Haruyoshi Osaki, Akihiro Furuta, Yukikazu Uemura, Takao Ninomiya, Yasunori Uetani, Makoto Hanabata
  • Patent number: 4789619
    Abstract: A positive-working radiation-sensitive mixture is described that contains (a) a radiation-sensitive compound which forms a strong acid under the action of actinic radiation, (b) a compound with at least one C--O--C bond cleavable by acid, (c) a binder which is insoluble in water but soluble in aqueous-alkaline solutions, and (d) a polymethine dye. The polymethine dyes used are hemioxonol dyes or symmetrical cyanine dyes. In the light-sensitive mixture, these dyes effect high sensitization and high image sharpness contrast which, in addition, is substantially irreversible.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: December 6, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Joachim Knaul
  • Patent number: 4764450
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C--O--C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: December 29, 1986
    Date of Patent: August 16, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher
  • Patent number: 4746591
    Abstract: A process for preparing a lithographic support, and the printing plate made therefrom, are described, wherein the process comprises the steps of (a) liquid-honing a surface of an aluminum sheet, and (b) electrochemically graining the surface of the aluminum sheet in an electrolyte comprises hydrochloric acid, nitric acid, or a mixture thereof.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: May 24, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hirokazu Sakaki, Akira Shirai, Akio Uesugi, Tsutomu Kakei
  • Patent number: 4745045
    Abstract: A method which provides for a permanent planarization layer on a multilayer integrated circuit. The planarization layer resides above other circuit layers which reflect incident light. A layer of photoresist is formed over the planarization layers and imaged through a mask with circuit defining structure. During exposure of the photoresist, incident light passes through the planarization layer. Scattering from the boundary of the planarization layer and photoresist is minimized because the index of refraction of the planarization layer is substantially equal to the index of refraction of the photoresist. Light reflected from the underlaying layers is substantially absorbed by the planarization layer. Reduction of the reflected and scattered light results in improved resolution of developed images in photoresist.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: May 17, 1988
    Assignee: International Business Machines Corporation
    Inventors: Edward C. Fredericks, Giorgio G. Via
  • Patent number: 4737426
    Abstract: Compounds of formula I ##STR1## in conjunction with compounds that donate acid when exposed to actinic radiation, are suitable for use as positive photoresists. In formula I, R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, cycloalkyl, aralkyl or alkaryl, R.sup.3 to R.sup.8 are hydrogen or lower alkyl, X is --O-- or --NR.sup.9 --, where R.sup.9 is hydrogen or C.sub.1 -C.sub.4 alkyl, n is 0 or 1, m is 2, 3 or 4 and Q is an organic radical of valency m.The photoresists are suitable for making printing forms, printed circuits, integrated circuits or silver-free photographic films.
    Type: Grant
    Filed: May 5, 1986
    Date of Patent: April 12, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Martin Roth
  • Patent number: 4710449
    Abstract: A novel low metal ion developer composition used in a two step process which provided high contrast images and long developer bath life is provided. The process gives high contrast images. The substrate coated with positive photoresist is exposed then immersed in a "predip" bath, rinsed, and then, immersed in the developer bath, rinsed and dried. This process provided high contrast which does not decrease over the life of the developer system. The system consists of (1) a predip solution containing aqueous non-metal ion organic base and a cationic surfactant adjusted to a concentration that does not give development, and (2) a developer solution containing an aqueous solution of an non-metal ion organic base and a fluorochemical surfactant adjusted to a concentration that provides development. The high contrast is achieved by the cationic surfactant coating the resist and inhibiting the attack on the unexposed resist by the developer while permitting the developer to dissolve away the exposed resist.
    Type: Grant
    Filed: January 29, 1986
    Date of Patent: December 1, 1987
    Assignee: Petrarch Systems, Inc.
    Inventors: James M. Lewis, Andrew J. Blakeney
  • Patent number: 4642282
    Abstract: A light-sensitive mixture is disclosed which contains a binder comprising a polycondensation product of a phenol corresponding to the formula ##STR1## wherein R.sub.1 is a hydrogen atom, an alkyl group or a hydroxy group,R.sub.2 is a hydrogen atom, an alkyl group, a hydroxy group or an acetyl group, andR.sub.3 is a hydrogen atom or a halogen atom, an alkyl group, an alkoxy group, a carboxyl group or a carboxylic acid ester group,and a compound corresponding to the formulaROCH.sub.2 --X--CH.sub.2 OR,whereinR is a hydrogen atom, a methyl group, an ethyl group or an acetyl group andX is a phenylene group or a binuclear aromatic group.The mixture yields printing plates which have a high resistance to developing solutions and which show a low degree of soiling upon baking.
    Type: Grant
    Filed: June 20, 1984
    Date of Patent: February 10, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 4640884
    Abstract: Quinone diazide derivatives of adamantane, and especially quinone diazide derivatives of 1,3-dialkyl-5,7-bis(hydroyphenol) adamantanes, have been found to provide unique properties when coated on metal substrate in the preparation of both positive and negative working lithographic plates. The improved lithographic plates are characterized by enhanced speed, coating oleophilicity, alkali resistance, developer latitude and development speed.
    Type: Grant
    Filed: March 29, 1985
    Date of Patent: February 3, 1987
    Assignee: Polychrome Corp.
    Inventors: William Rowe, Thomas Dooley
  • Patent number: 4609615
    Abstract: A process for forming patterns with a negative type resist which comprises the steps of forming a negative type resist film made of quinone diazide oligomer having a polymerization degree of 10 or less, such as a quinone diazide sulfonic ester on a substrate, irradiating the resist film selectively with far ultraviolet rays having a wavelength of 180-300 nm to expose the above film, and then developing the film thus exposed by the use of a suitable developer such as a solution containing any one of an acetic ester, an alkyl ketone and cyclohexanone, and another process wherein the above described exposing step is carried out in such a manner that the quinone diazide sulfonic ester film is subjected to blanket exposure by means of ultraviolet rays having a longer wavelength than 300 nm, and then the resist film, thus exposed, is further subjected to selective exposure by means of far ultraviolet rays of 300 nm or less.
    Type: Grant
    Filed: March 27, 1984
    Date of Patent: September 2, 1986
    Assignee: Oki Electric Industry Co., Ltd.
    Inventors: Yoshio Yamashita, Ryuji Kawazu
  • Patent number: 4606999
    Abstract: A method of developing a positive photoresist layer which has been image-wise-exposed comprising contacting the layer with an alkaline developing composition to remove exposed areas of the layer, the developing composition comprising a solution containing a cyclic quaternary ammonium hydroxide developing agent in a sufficient concentration to remove exposed areas of the layer. The present invention also includes a developing composition for use in the method.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: August 19, 1986
    Assignee: Thiokol Corporation
    Inventors: Susan B. Poulin, Ann B. Salamone
  • Patent number: 4601969
    Abstract: A lithographic resin for use with deep ultraviolet radiation comprises a weakly acidic resin and an alpha phosphoryl substituted diazo carbonyl compound as a sensitizer.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: July 22, 1986
    Assignee: International Business Machines Corporation
    Inventors: Nicholas J. Clecak, Barbara D. Grant, Robert D. Miller, Terry C. Tompkins, Carlton G. Willson
  • Patent number: 4596763
    Abstract: The invention provides a method for producing a positive working photoresist which comprises coating at least one novolak resin, and 1-naphthalenesulfonic acid, 3-diazo-3,4-dihydro-4-oxo-,4-benzoyl-1,2,3-benzenetriyl ester onto a substrate, exposing to a u.v. light source having a wavelength of less than 380 nanometers and developing with an aqueous alkaline solution.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: June 24, 1986
    Assignee: American Hoechst Corporation
    Inventors: John DiCarlo, Jonas St. Alban, Donald C. Mammato, Bruce M. Stevens
  • Patent number: 4591544
    Abstract: A metal image forming material in which the thin metal layer can be etched in short period to provide a sharp image without a strong etchant is disclosed. Said metal image forming material comprises a support, at least one metal layer and an overlying light sensitive layer. Said metal layer is formed by vapor-depositing a metal on the support at an angle with respect to the surface of the support.
    Type: Grant
    Filed: January 2, 1985
    Date of Patent: May 27, 1986
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Nobumasa Sasa, Yuzuru Sato, Tatsuo Ohta, Masanari Shindo
  • Patent number: 4588671
    Abstract: A photo- and electron resist distributed in an organic solvent, and including an additive which forms a donor-acceptor complex to eliminate luminescence effects and increase the stability of the resist.The photo- and electron resist can be used in microelectronics, optics, printing and precision machine building industry when resists are employed to manufacture structures of semiconductor devices and solid-state circuits.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: May 13, 1986
    Assignee: Institut Khimii Akademii Nauk SSSR
    Inventors: Sergei P. Molodnyakov, Jury I. Fedorov, Vitaly A. Kuznetsov, Alexei N. Egorochkin, Tamara G. Birjukova, Grigory A. Razuvaev
  • Patent number: 4564575
    Abstract: Reduction of the alkaline developer solubility of novolak-diazoquinone positive resists by acylation of phenolic hydroxyl groups of the novolak resin.
    Type: Grant
    Filed: January 30, 1984
    Date of Patent: January 14, 1986
    Assignee: International Business Machines Corporation
    Inventors: Stanley E. Perreault, Robert L. Wood
  • Patent number: 4544627
    Abstract: A negative-working image forming process which comprises uniformly exposing a photosensitive material comprising a support having thereon a sensitive layer comprising (i) an o-quinonediazide compound and (ii) a second compound, to actinic radiation which is able to convert the o-quinonediazide compound to the corresponding indenecarboxylic acid compound, and subsequent to said uniformly exposing imagewise exposing said exposed photosensitive material to a laser beam to thereby render the indenecarboxylic acid compound of the imagewise exposed areas convert to the corresponding indene compound and developing with an alkaline developing solution to dissolve out the unexposed area to the laser beam, wherein said second compound reduces the rate of dissolution of the laser exposed areas in the developing solution by converting the indenecarboxylic acid to the corresponding indene compound, whereby said image results.
    Type: Grant
    Filed: November 3, 1983
    Date of Patent: October 1, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yonosuke Takahashi, Hiromichi Tachikawa, Fumiaki Shinozaki, Tomoaki Ikeda
  • Patent number: 4506006
    Abstract: A process is described for preparing relief images, in which a light-sensitive material composed of a support and a light-sensitive layer which contains as essential constituents(a) a compound which has at least one C-O-C bond which is cleavable by acid,(b) a compound which forms a strong acid on irradiation and(c) a binder which is insoluble in water and soluble in aqueous-alkaline solutions is imagewise irradiated, warmed to an elevated temperature, cooled down and then irradiated over its entire area, whereafter those parts of the layer which have not been imagewise irradiated are then washed out by developing. The process makes it possible to prepare positive or negative copies by means of the same light-sensitive material in a simple way.
    Type: Grant
    Filed: December 14, 1982
    Date of Patent: March 19, 1985
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans Ruckert
  • Patent number: 4460674
    Abstract: A posi-type photosensitive composition having enhanced sensitivity is prepared by incorporating a specific sensitizer selected from gallic acid, its derivative, naphthoquinone compound and its derivative in a quinonediazide type photosensitive material. The composition is free from lowering in development tolerance and other properties.
    Type: Grant
    Filed: January 4, 1982
    Date of Patent: July 17, 1984
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Masafumi Uehara, Takeshi Yamamoto, Atsuo Yamazaki, Tohru Aoki
  • Patent number: 4458000
    Abstract: Disclosed is a light-sensitive mixture comprising (a) a 1,2-quinonediazide or a mixture of (a.sup.1) a compound forming an acid on exposure and (a.sup.2) a compound having at least one C--O--C bond cleavable by acid; (b) a water-insoluble binder soluble in aqueous-alkaline solutions; (c) a photolytically cleavable organic halogen compound of one of the formulae ##STR1## in which R.sup.1 denotes an aromatic radical bonded directly or via a conjugated chain, and X denotes a halogen atom; and (d) an azo dyestuff containing at least one nitro group in the molecule. Also disclosed are light-sensitive copying materials produced from these mixtures.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: July 3, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 4457999
    Abstract: Disclosed is a light-sensitive mixture comprising (a) a 1,2-quinonediazide or a mixture of (a.sup.1) a compound forming an acid on exposure and (a.sup.2) a compound having at least one C--O--C bond cleavable by acid; (b) a water-insoluble binder soluble in aqueous-alkaline solutions; (c) an organic compound forming an acid on exposure of the general formula I ##STR1## in which X is a single bond or one of the groups CO, SO.sub.2, N=N or CR.sup.7 R.sup.8, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are hydrogen atoms, halogen atoms or nitro groups, with not more than two of these radicals being hydrogen atoms and at least one thereof being a nitro group, R.sup.5 and R.sup.6 are hydrogen atoms or 1,2-naphthoquinone-2-diazide-4-sulfonyloxy radicals, with R.sup.5 and R.sup.6 being always different from each other, and R.sup.7 and R.sup.8 are hydrogen atoms or lower alkyl radicals, and (d) an azo dyestuff containing at least one nitro group in the molecule.
    Type: Grant
    Filed: September 28, 1982
    Date of Patent: July 3, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 4421839
    Abstract: A heat-sensitive recording sheet is proposed which has a heat-sensitive recording layer laminated on one surface of a support body and containing a diasosulfonate; a acid coupling agent comprising a compound having aromatic ring, hetroaromatic ring or substituted aromatic ring bonded thereto OH group and COOH group; and a thermoplastic resin having a glass transition point of 70.degree.-150.degree. C. or a photocuring resin.
    Type: Grant
    Filed: March 3, 1982
    Date of Patent: December 20, 1983
    Assignees: Dai Nippon Printing Co., Ltd., Tokyo Shibaura Denki Kabushiki Kaisha
    Inventors: Ryohei Takiguchi, Masayoshi Nagashima