Quinone Diazide Containing Layer Patents (Class 430/165)
  • 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: 5843616
    Abstract: A positive resist composition sensitive to radiations such as ultraviolet rays, far ultraviolet rays, which comprises;an o-quinonediazide compound; anda novolac resin(1) obtained by allowing an aromatic aldehyde of the formula(I) ##STR1## wherein R.sub.4 to R.sub.6 represents hydrogen, alkyl, cycloalkyl, alkoxy, alkenyl or aryl, k'0 represents an integer not smaller than 0 and p represents 1, 2 or 3, to react with a phenol compound of the formula (II) ##STR2## wherein R.sub.7 to R.sub.9 represents hydrogen, hydroxy, alkyl, cycloalkyl, alkoxy, alkenyl or aryl, provided that at least one of R.sub.7 to R.sub.9 is cycloalkyl having 6 or less carbon atoms, in the presence of an acid catalyst to obtain a reaction product(1) containing low molecular weight ingredients;and, then, allowing the reaction product(1) to further react with a phenol compound(1) and formaldehyde.
    Type: Grant
    Filed: April 10, 1995
    Date of Patent: December 1, 1998
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Kunishige Edamatsu, Yuji Yoshida, Kazuhiko Hashimoto, Haruyoshi Osaki
  • Patent number: 5840467
    Abstract: Disclosed is an image recording material which comprises a binder, a substance capable of generating heat by the absorption of light and a heat decomposable substance capable of substantially lowering the solubility of the binder when the substance is in an undecomposed state.
    Type: Grant
    Filed: October 28, 1996
    Date of Patent: November 24, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Katsuji Kitatani, Keitaro Aoshima, Yuichi Shiraishi, Kazuto Kunita, Hiroaki Yokoya
  • Patent number: 5821036
    Abstract: A method and composition for developing positive photoresists is illustrated. The developer of the present invention includes an ammonium hydroxide aqueous base and a surfactant of the fluorinated alkyl alkoxylate class most preferably present in an amount of from 10 to 30 ppm. A particularly preferred surfactant includes sulfonyl and amine moieties.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: October 13, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley A. Ficner, John Magvas, Christopher F. Lyons, Wayne M. Moreau, Marina V. Plat
  • Patent number: 5792586
    Abstract: The present invention provides a positive photoresist composition comprising a 1,2-naphthoquinonediazide compound and a novolac resin obtained through a condensation reaction between an aldehyde compound and a phenol compound represented by the following general formula (I): ##STR1## wherein R.sub.5, R.sub.6 and R.sub.7 each independently represents hydrogen atom, hydroxyl group or alkyl, cycloalkyl, alkoxy or alkenyl group having 6 or less carbon atoms or aryl group, provided that at least one of R.sub.5, R.sub.6 and R.sub.7 represents a cycloalkyl group having 6 or less carbon atoms. The composition of the present invention is excellent in the balance between properties such as sensitivity, resolution, heat resistance, profile, depth of focus, etc. and free from scum.
    Type: Grant
    Filed: November 3, 1994
    Date of Patent: August 11, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuhiko Hashimoto, Haruyoshi Osaki, Yasunori Uetani
  • 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: 5753405
    Abstract: A positive-working recording material is disclosed that has an aluminum base and a mat-finished radiation-sensitive layer that contains a 1,2-naphthoquinone-2-diazide as radiation-sensitive compound and a binder which is insoluble in water but soluble or swellable in aqueous alkali. The radiation-sensitive 1,2-naphthoquinone-2-diazide is an ester of 1,2-naphthoquinone-2-diazide-4- or -5-sulfonic acid and a phenolic compound that contains at least 2, preferably at least 3, phenolic hydroxyl groups, which ester has a phenolic hydroxyl group content of at least 0.5 mmol/g and a diazo unit content of at least 1.5 mmol/g. The binder is a phenol/formaldehyde novolak that contains at least 5 mmol/g phenolic hydroxyl groups, the phenol component of which contains at least 30 mol percent m-cresol and at least 10 mol percent of at least one xylenol and which has a weight-average M.sub.w of 2,000 to 12,000 (determined by means of GPC with polystyrene as standard).
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: May 19, 1998
    Assignee: AGFA-Gevaert AG
    Inventors: Andreas Elsaesser, Gerhard Buhr
  • Patent number: 5750310
    Abstract: There are provided a positive photoresist composition comprising an alkali-soluble resin and a 1,2-naphthoquinonediazide-5-(and/or-4-) sulfonic ester of a tetrahydroxy compound having a specific structure, said ester component having a pattern area in the high-performance liquid chromatography determined using ultraviolet rays of 254 nm accounting for 50% or more of the entire pattern area and a positive photoresist composition comprising an alkali-soluble resin and 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic esters of two kinds of specific polyhydroxy compounds. The positive photoresist is suitable for ultrafine working and ensures high sensitivity and high resolution and is improved with respect to film thickness dependency and standing wave.
    Type: Grant
    Filed: April 23, 1996
    Date of Patent: May 12, 1998
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Shinji Sakaguchi, Makoto Momota
  • Patent number: 5747198
    Abstract: A resist pattern formed on a substrate has a T-shaped cross section including a stem portion extending from the substrate surface and a cap portion connected to the stem portion and spaced from the substrate surface. Provided that .alpha. is a minimum of the angle which is defined between a tangent at the lower edge of the cap portion and the substrate surface, and h is the spacing between the lower edge of the cap portion and the substrate surface at an intermediate position, .alpha. and h fall within a range defined and encompassed by tetragon ABCD wherein A: .alpha.=0.degree., h=0.01 .mu.m, B: .alpha.=20.degree., h=0.01 .mu.m, C: .alpha.=20.degree., h=0.2 .mu.m, and D: .alpha.=0.degree., h=0.3 .mu.m.
    Type: Grant
    Filed: December 2, 1996
    Date of Patent: May 5, 1998
    Assignee: TDK Corporation
    Inventor: Akifumi Kamijima
  • Patent number: 5736292
    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, l, 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: April 7, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ayako Ida, Haruyoshi Osaki, Takeshi Hioki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
  • Patent number: 5731110
    Abstract: An azo dye for use in color filters soluble in alkaline aqueous solutions and organic solvents and having in one molecule at least one sulfonamido group of which one hydrogen atom is substituted; and a method for producing a color filter having a plurality of color filter elements which comprises the steps of a) coating a substrate with an organic solvent solution of a photoresist composition containing said azo dye and drying the coat to form an adhering layer, b) exposing a specific part of said layer to radiation ray, c) developing the exposed or unexposed region with alkali to form a colored pattern, and d) repeating the steps a)-c) on every dye of different color present in said composition.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: March 24, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
  • Patent number: 5731127
    Abstract: A photosensitive composition which comprises a resin (A) having urea bonds in its side chains and a photosensitive compound (B), wherein the resin (A) contains at least one resin selected from the group consisting of a vinyl polymer resin and a condensation polymer resin, provides a coating layer with excellent resistance to solvents and abrasion. The photosensitive composition is suitable for use in the production of planographic printing plates, integrated circuits (IC) or photomasks. A photosensitive planographic printing plate produced usig the photosensitive composition has superior press-life.
    Type: Grant
    Filed: April 9, 1996
    Date of Patent: March 24, 1998
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Yasuhiro Ishizuka, Maru Aburano, Eiji Hayakawa, Koji Oe
  • Patent number: 5728504
    Abstract: A positive photoresist composition comprising (A) an alkali-soluble resin and (B) a light-sensitive component comprising at least one compound represented by the following general formula (I): ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each independently a hydrogen atom, an alkyl group having 1-3 carbon atoms or an alkoxy group having 1-3 carbon atoms; R.sup.4 is a hydrogen atom or an alkyl group having 1-3 carbon atoms; a, b and c are an integer of 1-3; l, m and n are an integer of 1-3, in which at least part of the hydroxyl groups present are esterified with a quinonediazidosulfonic acid and a sulfonic acid which has a group represented by the following formula (II):--SO.sub.2 --R.sup.5 (II)where R.sup.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: March 17, 1998
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroshi Hosoda, Satoshi Niikura, Atsushi Sawano, Tatsuya Hashiguchi, Kazuyuki Nitta, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5723253
    Abstract: Disclosed is a light-sensitive composition containing an o-quinonediazide compound, a novolak resin and a polymer,characterized in that the polymer contains a constitutional unit selected from the group consisting of constitutional units represented by the formulae (I), (II) and (III): ##STR1## wherein R.sup.1 to R.sup.12 each represent a hydrogen atom, an alkyl group or a phenyl group,and a lithographic printing plate using the same.
    Type: Grant
    Filed: December 4, 1995
    Date of Patent: March 3, 1998
    Assignees: Konica Corporation, Mitsubishi Chemical Corporation
    Inventors: Katuhiko Higashino, Tomohisa Ohta, Shinichi Matsubara
  • Patent number: 5719004
    Abstract: A light-sensitive positive photoresist composition containing a film forming novolak resin, a quinone-diazide photoactive compound, a solvent, and a 2,4-dinitro-1-naphthol dye, where the dye is present at a level greater than 0.5 weight percent of the total photoresist composition. The dye reduces the linewidth variation of the resist pattern on a reflective substrate without significantly reducing the lithographic performance of the light-sensitive composition.
    Type: Grant
    Filed: August 7, 1996
    Date of Patent: February 17, 1998
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Ping-Hung Lu, Ralph R. Dammel, Elaine G. Kokinda, Sunit S. Dixit
  • Patent number: 5716753
    Abstract: A positive-working photosensitive composition comprises:(1) an alkali-soluble resin;(2) a quinonediazide compound;(3) an organic phosphoric compound; and(4) at least one of a phenylenediamine compound and a derivative thereof, 2-amino-1-phenylethanol, N-phenyldiethanolamine, N-phenylethanolamine, N-ethyldiethanolamine, and N-ethylethanolamine. The resist composition exhibits so higher an adhesion to a substrate than ever as to provide an enhanced accuracy in processing during etching, enabling subsequent faithful transfer of a finer pattern to the substrate.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: February 10, 1998
    Assignees: Fuji Photo Film Co., Ltd., Fuji Film Olin Co., Ltd.
    Inventors: Hiroshi Yoshimoto, Nobuo Suzuki, Wataru Ishii, Shinya Katoh, Hiroaki Matsuura
  • Patent number: 5707558
    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: October 2, 1995
    Date of Patent: January 13, 1998
    Assignees: Japan Synthetic Rubber Co., Ltd., Arakawa Chemical Industries, Ltd.
    Inventors: Katsumi Inomata, Nasahiro Akiyama, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5705308
    Abstract: An infrared imaging composition contains two essential components, namely an infrared absorbing compound, and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in photosensitive elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: January 6, 1998
    Assignee: Eastman Kodak Company
    Inventors: Paul Richard West, Eugene Lynn Sheriff, Jeffrey Allen Gurney, Ralph Scott Schneebeli, Thomas Robert Jordan, Gary Roger Miller
  • Patent number: 5702861
    Abstract: A positive photoresist composition comprising: (A) an alkali-soluble resin; (B) a quinone diazide group-containing compound; and (C) at least one compound selected from the polyhydroxy compounds, such as 1,3-bis?2-(5-cyclohexyl-2-methyl-4-hydroxyphenyl)-2-propyl!benzene. The composition of the present invention exhibits excellent image contrast between exposed portions and unexposed portions, and actualizes formation of a resist pattern with excellent resolution, exposure range, and focal depth range.
    Type: Grant
    Filed: January 30, 1997
    Date of Patent: December 30, 1997
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Satoshi Niikura, Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5700621
    Abstract: A polymer comprising repeating units of the formula ##STR1## wherein R.sup.1 , R.sup.2 and R.sup.3 are, independently of one another, hydrogen atoms or alkyl groups,X is CO or SO.sub.2, andY and Z are, independently of one another, alkyl, alkenyl, cycloalkyl, aryl or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered hetero-cyclic ring.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: December 23, 1997
    Assignee: Agfa-Gevaert AG
    Inventors: Mathias Eichhorn, Andreas Elsaesser
  • Patent number: 5683851
    Abstract: Provided is a positive photoresist composition comprising (A) an alkali-soluble resin prepared by condensation of aldehydes and a mixture of phenols, which comprises (i) thymol, isothymol or a thymol-isothymol mixture and (ii) one or more of a phenol compound represented by the following formula (I); ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different, and each of them represents a hydrogen atom or a methyl group, and optionally, as a third monomer, (iii) a phenol compound other than m-cresol; (B) 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic acid esters as photosensitive agent; and (C) a low molecular weight compound having from 12 to 50 carbon atoms in all and from 2 to 8 phenolic hydroxy groups.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: November 4, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Shinji Sakaguchi
  • Patent number: 5679495
    Abstract: A radiation sensitive resin composition which comprises (A) a polymer which becomes alkali-soluble in the presence of an acid and (B) a radiation sensitive acid generator which generates an acid upon irradiation with a radiation, said polymer (A) comprising two recurring units represented by the general formulas (1) and (2) and a recurring unit which acts to reduce the solubility of the polymer in an alkali developer after the irradiation: ##STR1## wherein R.sup.1 represents a hydrogen atom or a methyl group and R.sup.2 represents a hydrogen atom or a methyl group. Said composition provides a chemically amplified positive resist which can give a fine pattern with a good pattern shape, and said resist is freed from volume shrinkage, peeling failure and adhesive failure, is excellent in dry etching resistance and effectively reacts with various radiations to give a good pattern shape which is excellent in photolithographic process stability, said pattern shape having no thinned portion at the upper part.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: October 21, 1997
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Mikio Yamachika, Eiichi Kobayashi, Toshiyuki Ota, Akira Tsuji
  • Patent number: 5677103
    Abstract: A positive photoresist composition which is of high resolution, high sensitivity and wide focusing range and suitable for high integration of semiconductor devices and shows superior resist pattern profile, comprising quinonediazide sulfonic acid ester as a photoresist, an alkali soluble resin, a solvent, and additives, said quinonediazide sulfonic acid ester being prepared through the esterification of 1,2-naphthoquinonediazidesulfonyl halide or 1,2-benzoquinonediazidesulfonyl halide with an aromatic hydroxy compound represented by the following structural formula I: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, an alkyl group or an alkoxy group; a is an integer of 1 to 3; b is an integer of 1 to 8; c is an integer of 1 to 12; and R.sub.3 is an alkyl group containing ether, mercapthane, sulfoxide, sulfone, aryl group or hydroxy group.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: October 14, 1997
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Seong-Ju Kim, Joo-Hyeon Park, Ji-Hong Kim, Sun-Yi Park
  • Patent number: 5677101
    Abstract: Disclosed is a light-sensitive lithographic printing plate which comprises an aluminum plate having a surface subjected to roughening treatment and then anodization treatment and colored by a solution containing a UV absorber so that at an absorption local maximum wavelength between 340 and 450 nm, reflection optical density DS is higher by 0.02 to 0.5 than that obtained when the surface is not colored, and a positive light-sensitive composition layer containing an o-quinonediazide compound and a clathrate compound provided by coating on the aluminum plate after coloration.
    Type: Grant
    Filed: June 19, 1995
    Date of Patent: October 14, 1997
    Assignee: Konica Corporation
    Inventors: Kazuo Noguchi, Kaori Fukumuro, Shinichi Matsubara, Yoshihiro Koya, Hiroshi Tomiyasu, Shigeru Kajiwara
  • Patent number: 5670294
    Abstract: The present invention relates to an aqueous alkaline developing solution comprising an alkaline mixture of an alkali metal silicate and/or an alkali metal metasilicate, wherein the M.sub.2 O/SiO.sub.2 molar ratio of said alkaline mixture is in the range of from 0.5 to 1.2, the total content of said alkaline mixture being in the range of from 6 to 15% by weight of the total developing solution, and wherein said developing solution comprises a non-ionic surfactant and at least another surfactant selected from the group consisting of anionic surfactants and amphoteric surfactants. An alkali metal hydroxide can be optionally added to the alkaline mixture. Also claimed is the concentrated developing solution to be diluted to the desired strength.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: September 23, 1997
    Assignee: Imation Corp
    Inventor: Mario Piro
  • Patent number: 5670293
    Abstract: Disclosed are a positive type lead-frame forming material which contains a light-sensitive material comprising an o-quinonediazide compound and a novolak resin, and a positive type lead-frame forming material which contains a positive resist composition comprising (1) a water-insoluble but alkaline water-soluble resin, (2) a compound capable of generating an acid by irradiation with active rays or radiant rays, and (3) a compound containing a group decomposable by acid which can increase its solubility in an alkaline developer through the action of the acid.
    Type: Grant
    Filed: March 10, 1995
    Date of Patent: September 23, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuhito Naruse, Kiyoshi Kamitani, Akio Uesugi, Tsutomu Kakei, Gouichi Morohoshi
  • Patent number: 5667932
    Abstract: Disclosed is a positive photoresist composition comprising an alkali-soluble resin and 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic esters of a polyhydroxy compound having a particular structure consisting of 5 aromatic rings linked linearly, in which each of the aromatic rings contains a hydroxyl group and the respective aromatic rings next to both the terminal rings contains a substituent group at the 5-position to the hydroxyl group thereof. The positive photoresist composition which has high resolution, low dependence of the resolution on film thickness, and broad latitude of development, leaves little development residue, and has very excellent storage stability without separation of photosensitive materials and generation of microgel (no increase in particle) with a lapse of time.
    Type: Grant
    Filed: May 21, 1996
    Date of Patent: September 16, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Kunihiko Kodama, Makoto Momota
  • Patent number: 5652081
    Abstract: Provided is a positive working photoresist composition which comprises an alkali-soluble resin and a 1,2-quinonediazide compound, with the resin being a novolak resin obtained by the condensation reaction of monomers comprising specified phenol compounds with formaldehyde.
    Type: Grant
    Filed: September 5, 1996
    Date of Patent: July 29, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Shinji Sakaguchi, Yasumasa Kawabe
  • Patent number: 5648194
    Abstract: A photoresist composition comprising an alkali soluble resin, an o-naphthoquinone diazide sulfonic acid ester photoactive compound, and a vinyl ether compound. The o-naphthoquinone diazide sulfonic acid ester is replaced in part with the vinyl ether composition to decrease the concentration of the photoactive compound while increasing the photospeed of the composition.
    Type: Grant
    Filed: August 3, 1995
    Date of Patent: July 15, 1997
    Assignee: Shipley Company, L.L.C.
    Inventors: Daniel Y. Pai, Robert E. Hawkins
  • Patent number: 5645969
    Abstract: A photosensitive composition comprising a quinonediazide compound and a binder resin, wherein said resin is a resin obtained by condensing a phenol component comprising the following (1) to (3), and an aldehyde or a ketone, and X.gtoreq.0.57, where X=A/B, where A is an integrated value of peaks from 23.0 to 31.0 ppm, and B is an integrated value of peaks from 23.0 to 37.0 ppm, in the .sup.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: July 8, 1997
    Assignees: Mitsubishi Chemical Corporation, Konica Corporation
    Inventors: Fumiyuki Matsuo, Daisuke Kanazawa, Mitsuru Sasaki, Shinichi Matsubara, Katsuhiko Higashino, Toshiaki Yokoo
  • Patent number: 5645970
    Abstract: A positive photoresist composition is disclosed which comprises a photosensitive compound, a phenolic resin, and an organic solvent. The phenolic resin is prepared from a monomeric composition comprises formaldehyde and a mixture of phenol monomers. The mixture of phenol monomers comprises: (a) no more than 98 mole percent of a mixture of monohydroxy phenols, the mixture of monohydroxy phenols comprises: (I) about 50.about.80 mole percent of meta-methylphenol; (ii) about 10.about.30 mole percent of 2,5-dimethylphenol; and (iii) about 10.about.40 mole percent of 2,3,5-trimethylphenol; and (b) at least 2 mol percent of at least one polyhydroxybenzene which is presented by the following formula: ##STR1## wherein n is an integer of 1 or 2. Preferably, the polyhydroxybenzene is a mixture of trihydroxybenzene and dihydroxybenzene in a molar ratio of about 40 to 60.
    Type: Grant
    Filed: October 25, 1995
    Date of Patent: July 8, 1997
    Assignee: Industrial Technology Research Institute
    Inventors: Hua-Chi Cheng, Chao H. Tseng, Pao-Ju Hsieh
  • Patent number: 5635329
    Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide-type photosensitive compound and a solvent, wherein the alkali-soluble resin is a polycondensation product of 1 at least one phenolic compound (A) of the following formula (A) with 2 formaldehyde (a) and at least one carbonyl compound (b) of the following formula (B), in which the mixing ratio of the formaldehyde (a) to the carbonyl compound (b) is within a range of from 1/99 to 99/1 in terms of the molar ratio of (a)/(b), and the alkaline soluble resin has partial structures of the following formula (C), in which the weight ratio of repeating units (.beta.) wherein m is from 1 to 5, to repeating units (.alpha.) wherein m is 0, i.e. the weight ratio of (.beta.)/(.alpha.), is at most 0.25: ##STR1## wherein R.sup.1 is a group of the formula R.sup.2, OR.sup.3, COOR.sup.4 or CH.sub.2 COOR.sup.5, wherein R.sup.2 is a C.sub.1-4 alkyl group, each of R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: June 3, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mineo Nishi, Koji Nakano, Makoto Ikemoto
  • Patent number: 5635328
    Abstract: Disclosed are a light-sensitive lithographic printing plate which comprises a support subjected to graining treatment and anodization treatment and a layer of a positive light-sensitive composition containing a o-quinonediazide compound, an alkali-soluble resin and a clathrate compound provided on the support, and a method of processing the same which comprises subjecting the plate to image exposure and then development processing with a developing agent containing an alkali metal silicate.
    Type: Grant
    Filed: August 16, 1994
    Date of Patent: June 3, 1997
    Assignees: Konica Corporation, Mitsubishi Chemical Corporation
    Inventors: Katuhiko Higashino, Kaori Fukumuro, Shinichi Matsubara, Mitsuru Sasaki, Katsuko Ohta, Fumiyuki Matsuo
  • Patent number: 5633111
    Abstract: A positive type or negative type photoresist composition for fine processing having excellent resolution, sensitivity, adhesive-ness and developability comprising:(a) an alkali soluble resin or a resin having anti-alkali dissolution groups in the molecules thereof,(b) a light-sensitive compound, and(c) at least one organic compound selected from the group consisting of organic phosphorus acid compounds and esters thereof in an amount of 0.001 to 10% by weight based on a weight of the resin. In addition, the present invention is directed to an etching method utilizing the positive type or negative type photoresist composition.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: May 27, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Yoshimoto, Kesanao Kobayashi
  • Patent number: 5624781
    Abstract: A positive type anionic electrodeposition photoresist composition comprising, as a main component, a dispersion obtained by neutralizing, with a base, a mixture comprising:(A) an acrylic resin containing carboxyl group(s) and hydroxyl group(s),(B) a vinylphenol resin containing a hydroxystyrene unit in an amount of at least 25% by weight based on the resin, and(C) an ester between a polyhydroxybenzophenone and 1,2-naphthoquinone diazide sulfonic acid or benzoquinone diazide sulfonic acid, and dispersing the resulting neutralization product in water.This composition is superior in running stability during electrodeposition and is useful for formation of highly reliable resist pattern or conductor pattern.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: April 29, 1997
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Keisuke Naruse, Yukari Takeda, Naozumi Iwasawa, Hideo Kogure
  • Patent number: 5612164
    Abstract: A photosensitizer comprising a trishydroxyphenylethane 80/20 to 50/50 2,1,5-/2,1,4-diazonaphthoquinone sulfonate, and a trishydroxybenzophenone 0/100 to 20/80 2,1,5-/2,1,4-diazonaphthoquinone sulfate, and a photoresist composition containing such photosensitizer, the photosensitizer being present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; and 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.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: March 18, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: Anthony Canize, Stanley A. Ficner, Ping-Hung Lu, Walter Spiess
  • Patent number: 5580702
    Abstract: Disclosed herein is a resist for forming patterns, which is greatly sensitive to ultraviolet rays an ionizing radiation, and which can therefore form a high-resolution resist pattern if exposed to ultra violet rays or an unionizing radiation. Hence, the resist is useful in a method of manufacturing semicon ductor devices having high integration densities. The resist comprises tert-butoxycarbonyl methoxypolyhydroxy styrene and an o-quinonediazide compound.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: December 3, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Noahiko Oyasato, Yoshihito Kobayashi, Shuzi Nayase
  • Patent number: 5576137
    Abstract: The invention relates to a non-continuous matte layer that can be used with a recording material having a substrate and a radiation-sensitive layer which contains a 1,2-naphthoquinone-2-diazide and an organic, polymeric binder which is insoluble in water but soluble in aqueous alkaline solutions. This matte layer comprises 100 to 10,000 particles per square centimeter which have a mean diameter of less than 40 .mu.m and a maximum diameter of less than 80 .mu.m and a mean height of 2 to 6 .mu.m and a maximum height of 10 .mu.m, and contains a resin which has up to 0.80 mmol of acid groups and/or salt groups per gram. The matte layer is obtained by spraying on and drying an aqueous, anionically or anionically/nonionically stabilized dispersion of the resin.
    Type: Grant
    Filed: September 14, 1994
    Date of Patent: November 19, 1996
    Assignee: Agfa-Gevaert AG
    Inventors: Werner Frass, Otfried Gaschler, Klaus Joerg, Guenter Hultzsch, Andreas Elsaesser
  • Patent number: 5573886
    Abstract: A photosensitive resin composition which comprises (A) a polyimide resin precursor of recurring units of a specific type, (B) at least one member selected from the group consisting of photosensitive diazoquinone compounds of the following formulas ##STR1## wherein R.sup.2 represents an organic group having from 1 to 50 carbon atoms, i is an integer of from 1 to 7, and i is an integer of from 1 to 7, and (C) a phenolic novolac resin. A method for forming a polyimide film pattern on various types of substrates is also described wherein a composition film is alkali-developed after imagewise exposure and cured to provide a heat-resistant polyimide film pattern suitable for protecting the substrate.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: November 12, 1996
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Satoshi Toyoda
  • Patent number: 5565300
    Abstract: A photoresist composition is disclosed containing an alkali-soluble resin and a photosensitive substance obtained by reaction of a polyhydroxy compound and (a) a 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonyl chloride(s), said photosensitive substance being a mixture of photosensitive compounds (1) to (3):(1) a photosensitive compound having at least one hydroxyl group per molecule and having a number ratio of 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonyl chloride sulfonate groups to hydroxyl groups within the range of from 3 to 20, contained in the photosensitive substance in an amount of 50 wt % or more;(2) a photosensitive compound where all the hydroxyl groups in the polyhydroxy compound have been 1,2-naphthoquinonediazidosulfonyl-esterified, contained in the photosensitive substance in an amount of 30 wt % to 0 wt %; and(3) a photosensitive compound having three or more hydroxyl groups which have not been 1,2-naphthoquinonediazidosulfonyl-esterified per molecule, contained in the photosensitive subs
    Type: Grant
    Filed: January 30, 1991
    Date of Patent: October 15, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Shinji Sakaguchi, Tadayoshi Kokubo
  • Patent number: 5563023
    Abstract: A photoimageable element comprising: a substrate; a layer of a photosensitive composition comprising a photosensitive material coated on the substrate; and a protective overcoating comprising an oxygen barrier polymeric material and antiblocking particulate material wherein the oxygen barrier component has an oxygen permeability of no greater than about 10.sup.-14 cc(cm)/cm.sup.2 (sec)(Pa).
    Type: Grant
    Filed: November 2, 1994
    Date of Patent: October 8, 1996
    Assignee: Minnesota Mining and Manufacturing Co.
    Inventors: Steven L. Kangas, Emil D. Sprute, Dean J. Stych
  • Patent number: 5563018
    Abstract: The invention relates to 2,3,4-trihydroxy-3'-methyl-, -ethyl-, -propyl- or -isopropylbenzophenone which is completely esterified with (1,2-naphthoquinone 2-diazide)-4-sulfonic acid and/or (7-methoxy-1,2-naphthoquinone 2-diazide)-4-sulfonic acid, a radiation-sensitive mixture prepared therewith, and a radiation-sensitive recording material comprising a substrate and a radiation-sensitive layer which is composed of the mixture according to the invention.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: October 8, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Buhr, Wolfgang Zahn, Fritz Erdmann, Siegfried Scheler
  • Patent number: 5554481
    Abstract: A positive working photoresist composition sensitive to radiation, having high resolving power, high sensitivity, and excellent storage stability, and further forming a pattern capable of accurately reproducing a mask size in a wide range of photomask line width. The present invention has been obtained by a composition containing at least one of a 1,2-napthoquinonediazido-5-sulfonic acid ester of a polyhydroxy compound and a 1,2-napthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound in combination with at least one alkali-soluble resin.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: September 10, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Satoh, Toshiaki Aoai
  • Patent number: 5552255
    Abstract: Proposed is an alkali-soluble, positive-working photo-sensitive resin composition which can be used as a material for forming a finely patterned resist layer on the surface of a metallic substrate such as tantalum to exhibit excellent adhesion of the patterned resist layer to the substrate surface. The composition comprises, in addition to a novolac resin as a film-forming agent and a naphthoquinone diazide group-containing compound as a photosensitizer, an aromatic compound having two benzene rings and at least five phenolic hydroxy groups in a molecule such as pentahydroxy and hexahydroxy benzophenone compounds as an adhesion improver.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: September 3, 1996
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tetsuya Kato, Kouichi Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5550001
    Abstract: A radiation-sensitive plate comprises a substrate coated with a radiation-sensitive composition including a component having groups imparting solubility in aqueous solutions and a component having functional groups capable of reacting with a silane compound. The surface of the composition is modified by reaction with a silane compound. The plate gives rise to images of improved ink receptivity and can be developed in aqueous developer liquids after image-wise exposure.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: August 27, 1996
    Assignee: DuPont (U.K.) Limited
    Inventors: John R. Wade, Michael J. Pratt, Robert A. W. Johnstone, David I. Smith
  • Patent number: 5547814
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: August 20, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
  • Patent number: 5541033
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a positive photoresist composition and process for forming patterned image. Further the invention is drawn to a positive photoresist composition comprising an alkali-soluble resin and quinone diazide sulfonic acid triesters and diesters characterized by their HPLC peak areas.
    Type: Grant
    Filed: February 1, 1995
    Date of Patent: July 30, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
  • Patent number: 5538820
    Abstract: The invention provides a method for forming a photoresist mask on a substrate resistant to reticulation during plasma etching. The method comprises the steps of forming an imaged and developed photoresist coating over an integrated circuit substrate where the photoresist contains an essentially unreacted acid activated cross linking agent, and subjecting said substrate to an etching plasma in a gaseous stream that contains a Lewis acid. Contact of the surface of the photoresist film with the Lewis acid causes cross linking of the surface of the photoresist film during plasma etching with the formation of a reticulation resistant surface layer.
    Type: Grant
    Filed: August 18, 1993
    Date of Patent: July 23, 1996
    Assignee: Shipley Company Inc.
    Inventor: Thomas A. Fisher
  • Patent number: 5536616
    Abstract: A photoresist is provided. The photoresist comprises a polymer, a photoactive agent, and a crosslinking agent. The crosslinking agent comprises a water soluble sugar. The present invention also provides a method of making microelectronic structures.
    Type: Grant
    Filed: September 21, 1994
    Date of Patent: July 16, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Sze-Ming Lee
  • Patent number: 5534382
    Abstract: Disclosed is a positive photoresist composition comprising an alkali-soluble resin and the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonate acid ester of a polyhydroxy compound represented by formula (I): ##STR1## wherein R.sub.1 to R.sub.3 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, or an alkoxy group; and m, n and o each represent an integer of from 1 to 3. The photoresist composition has a high resolving power and a less layer thickness reliance of the resolving power, and a wide development latitude, is reluctant to form a development residue, and further has a very excellent storage stability, and does not deposit the photosensitive material and does not form microgels, i.e., shows no increase in the particles, with the passage of time.
    Type: Grant
    Filed: March 27, 1995
    Date of Patent: July 9, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Sato