Polymeric Mixture Patents (Class 430/192)
  • Patent number: 5639587
    Abstract: A positive photoresist composition is disclosed, which comprises an alkali-soluble resin, at least one of 1,2-naphthoquinonediazidesulfonic monoesters of specific polyhydroxy compounds, and at least one of 1,2-naphthoquinonediazidesulfonic ester of specific polyhydroxy compounds. The positive photoresist composition exhibits remarkably improved sensitivity and resolution, and broad development latitude regardless of the film thickness, and further, low film thickness dependence of resist performances.
    Type: Grant
    Filed: March 14, 1996
    Date of Patent: June 17, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Koji Shirakawa, Shinji Sakaguchi
  • 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: 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: 5631119
    Abstract: The present invention provides an image-forming material which comprises a support having thereon, in the following order, (1) a photosensitive composition layer comprising (a) an o-quinonediazide compound, and (b) an additive which reacts with a photoreaction product of the o-quinonediazide compound on heating to produce an alkali-insoluble matter, and (2) a water-soluble high molecular compound layer or a silicone rubber layer. The present invention also provides an image formation process which comprises exposing an entire surface of the image-forming material to light rays which render the o-quinonediazide compound soluble in an alkaline developer, imagewise heating the image-forming material, and then developing the image forming material with an alkaline developer to remove those areas which have not been heated.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: May 20, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Fumiaki Shinozaki
  • Patent number: 5629127
    Abstract: The present invention relates to a positive electron beam resist composition containing a cresolnovolak resin, a lower molecular additive with a specific structure and a quinonediazide compound with a specific structure, and a developer for the positive electron beam resist, containing specific amounts of alkali metal ions, weak acid radical ions and a water soluble organic compound. The present invention can provide a positive electron beam resist composition with a novolak and a quinonediazide as main ingredients, excellent in dry etching resistance and resolution, and it if is used, a fine pattern can be obtained at high sensitivity especially when the developer of the present invention is used.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: May 13, 1997
    Assignee: Toray Industries, Inc.
    Inventors: Hiroki Oosedo, Mutsuo Kataoka, deceased, Mayumi Kataoka, legal representative, Shigeyoshi Kanetsuki, Kazutaka Tamura, Masaya Asano
  • Patent number: 5629128
    Abstract: A positive photoresist composition is described, which comprises an alkali-soluble resin and 1,2-naphthoquinone-diazido-5-(and/or -4-)sulfonate of a polyhydroxy compound represented by the following formula (I): ##STR1## wherein R.sub.1 to R.sub.11 are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxyl group, an acyl group or a cycloalkyl group, provided that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group; A represents -CH(R.sub.12)-, in which R.sub.12 represents a hydrogen atom or an alkyl group; and m represents 2 or 3.
    Type: Grant
    Filed: September 20, 1995
    Date of Patent: May 13, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koji Shirakawa, Kenichiro Sato, Kunihiko Kodama, Yasumasa Kawabe, Shinji Sakaguchi
  • Patent number: 5627006
    Abstract: A photoresist composition comprising (a) a difficultly alkali-soluble special resin, (b) a photo-sensitive compound capable of generating a carboxylic acid, and (c) a solvent, is effective for pattern formation using deep ultraviolet light, KrF excimer laser beams, etc.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: May 6, 1997
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
  • 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: 5624788
    Abstract: Disclosed are an organic silicon compound having a repeating unit represented by general formula (I) shown below, a resist, a thermal polymerization composition and a photopolymerization composition containing the organic silicon compound, ##STR1## wherein R.sup.1 is a t-butyl group or a tetrahydropyranyl group, R.sup.2 is an hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 1 to 24 carbon atoms, or a substituted or unsubstituted aralkyl having 7 to 24 carbon atoms, R.sup.3 is a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms or an alkoxyl group, and k represents an integer from 0 to 4.
    Type: Grant
    Filed: June 15, 1995
    Date of Patent: April 29, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shinji Murai, Yoshihiko Nakano, Ken Uchida, Shuji Hayase
  • Patent number: 5620828
    Abstract: A positive photoresist composition is disclosed, which comprises prescribed amounts of an alkali-soluble novolak resin which is obtained from prescribed amounts of m- and p-cresols and at least one xylenol selected from 2,3-, 3,4- and 3,5-xylenols and an aldehyde, a 1,2-quinonediazide compound which is an esterified product of a polyhydroxy compound having from 3 to 7 phenolic hydroxyl groups in the molecule with 1,2-naphthoquinonediazido-5(and/or 4)-sulfonyl chloride(s) and an alkali dissolution accelerator which is a polyhydroxy compound having a molecular weight of 1,000 or less and from 2 to 7 phenolic hydroxyl groups in the molecule.
    Type: Grant
    Filed: December 27, 1995
    Date of Patent: April 15, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Yasumasa Kawabe
  • Patent number: 5614349
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a precise and consistent molecular weight, by adjusting the concentration of Lewis base. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: March 25, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Daniel P. Aubin, Dana L. Durham, Ralph R. Dammel
  • 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: 5609983
    Abstract: There is provided a positive working photosensitive composition suitable for photosensitive lithographic printing plate or photoresist for fine processing, which comprises a quinonediazide ester compound having the structure characterized by containing in the same molecule both quinonediazide structure and N-sulfonylamide [--C(.dbd.O)--NHSO.sub.2 --] or sulfonamide [--NHSO.sub.2 --] structure which are positioned independently of each other.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Kenichiro Sato, Shinji Sakaguchi
  • Patent number: 5609982
    Abstract: The present invention provides a positive-working photoresist composition comprising an alkali-soluble resin and a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic ester of a specific water-insoluble alkali-soluble low molecular compound, wherein the high-performance liquid chromatography of the ester with an ultraviolet ray at 254 nm shows that the patterns corresponding to the diester components and complete ester component of the ester each fall within the specific range and a positive-working photoresist composition comprising a water-insoluble alkali-soluble resin, a water-insoluble alkali-soluble low molecular compound, and an ionization-sensitive radioactive compound which comprises a mixture of a naphthoquinone-diazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having three phenolic hydroxyl groups as an ionization-sensitive radioactive compound (A) and a naphthoquinonediazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having four phenoli
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Yasumasa Kawabe, Toshiaki Aoai, Shinji Sakaguchi
  • Patent number: 5609994
    Abstract: A method for patterning a photoresist film, capable of preventing a notching phenomenon occurring upon forming a pattern of the photoresist film having a single layer structure and thereby accurately forming a pattern of a metal wiring or a gate with a desired dimension even on a layer exhibiting a severe topology by removing a portion of the photoresist film coated over the layer having a severe topology up to a depth corresponding to 30% or below of the thickness of the photoresist film to form a recess, forming an planarized inorganic material layer on the recess, and selectively removing a predetermined portion of the photoresist film under a condition that the inorganic material layer is used as a mask.
    Type: Grant
    Filed: December 21, 1994
    Date of Patent: March 11, 1997
    Assignee: Goldstar Electron Co., Ltd.
    Inventor: Jun Seok Lee
  • Patent number: 5604077
    Abstract: Proposed is an improved positive-working photoresist composition for use in the photolithographic patterning works for the manufacture of semiconductor devices, which is capable of giving a patterned resist layer on a substrate surface having excellent resolution and heat resistance without formation of scum in the development treatment. The photoresist composition comprises: (a) an alkali-soluble novolac resin as a film-forming ingredient and (b) a naphthoquinone diazide group-containing compound as a photosensitizing ingredient, of which the novolac resin is a condensation product of a phenolic compound and an aldehyde compound, the condensation reaction being undertaken in a solvent system containing, in addition to water, .gamma.-butyrolactone or a combination of .gamma.-butyrolactone and a propyleneglycol monoalkyl ether in a limited proportion.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: February 18, 1997
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Kono, Hayato Ohno, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5601961
    Abstract: Disclosed is an improved positive-working photoresist composition comprising an alkali-soluble resin as a film-forming agent and a quinone diazide group-containing compound as a photosensitive agent. The most characteristic feature of the inventive composition consists in the unique formulation of the alkali-soluble resin which is a combination of two or three kinds of novolac resins selected from novolac resins (a), (b1) or (b2) and (c1) or (c2), each of which is characterized by the unique formulation of the phenolic compounds as a mixture to be subjected to a condensation reaction with an aldehyde compound to form the novolac resin.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: February 11, 1997
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazuhiko Nakayama, Taku Nakao, Kousuke Doi, Nobuo Tokutake, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5585217
    Abstract: Disclosed herein is a polyamic acid composition which comprises an aromatic carboxylic acid compound having phenolic hydroxyl groups, polyamic acid, and a photosensitizer made of a diazide compound, and which can form a polyimide film pattern having a high resolution and capable of firmly adhering to a substrate.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: December 17, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Masayuki Oba
  • 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: 5576139
    Abstract: A novel positive type photoresist composition is provided, comprising an alkali-soluble novolak resin obtained by the condensation of substituted or unsubstituted phenols and aldehydes in the presence of a silica-magnesia solid catalyst and a light-sensitive material containing 1,2-naphthoquinone-diazido-5-(and/or -4-) sulfonate as main component.
    Type: Grant
    Filed: October 28, 1991
    Date of Patent: November 19, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Shiro Tan, Yasumasa Kawabe, Tadayoshi Kokubo
  • 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: 5576138
    Abstract: Disclosed is a positive-working photoresist composition used in the photolithographic patterning work for the manufacture of various electronic devices such as VLSIs having improved characteristics, in particular, in respect of the halation-preventing effect. In addition to the conventional ingredients of (a) an alkali-soluble novolac resin as a film-forming agent and (b) a naphthoquinonediazide group-containing compound as a photosensitizing agent, the composition is formulated by the admixture of a specific amount of (c) a halation-preventing agent which is a combination of, one, (c1) a 4,4'-bis(dialkylamino) benzophenone compound and, the other, (c2) a compound selected from the group consisting of polyhydroxy benzophenone compounds, amino- and hydroxy-containing benzophenone compounds and 4-pyrazolylazo compounds in a specific weight proportion of (c1):(c2).
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: November 19, 1996
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshito Ando, Atsushi Sawano, Nobuo Tokutake, Hidekatsu Kohara, Toshimasa Nakayama
  • 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: 5571886
    Abstract: An essentially aromatic alkali soluble novolak resin comprising the product resulting from the acid condensation of an aromatic aldehyde and a phenol where the resin has a molecular weight in excess of 1500 and a glass transition temperature in excess of 125.degree. C. If desired, the aromatic novolak resin may be blended with a conventional novolak resin to regulate the glass transition temperature of the resin. The aromatic novolak resin and blends formed therefrom are especially suitable as coating resins and are useful for the formation of photoresist coating compositions.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: November 5, 1996
    Assignee: Shipley Company, Inc.
    Inventor: Anthony Zampini
  • 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: 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: 5556734
    Abstract: A radiation sensitive resin composition which comprises (A) a copolymer represented by the following general formula and (B) a radiation sensitive acid generator and, if necessary, (C) an alkali-soluble resin: ##STR1## wherein R represents a hydrogen atom or a methyl group and m and n are integers representing the numbers of the respective recurring units and satisfying the relations 0.1.gtoreq.m/(m+n)<0.6 and 0.4<n/(m+n).ltoreq.0.9. Said radiation sensitive resin composition is excellent in resolution and pattern profile and also excellent in sensitivity and developability and is useful as a chemically amplified resist good in contrast and heat resistance.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: September 17, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Mikio Yamachika, Eiichi Kobayashi, Toshiyuki Ota, Akira Tsuji
  • 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: 5554465
    Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: September 10, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5552256
    Abstract: Quinone diazo compounds having bonded to the diazo ring or directly bonded to a ring of the compound, certain non-metallic atoms that improve the photosensitivity thereof are provided. These quinone diazo compounds are useful as photoactive compounds in photoresist compositions, and particularly positive photoresist composition employed in x-ray or electron beam radiation. Also provided is a method for preparing compounds of the present invention.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: September 3, 1996
    Assignee: International Business Machines Corporation
    Inventors: Ari Aviram, William R. Brunsvold, Daniel Bucca, Willard E. Conley, Jr., David E. Seeger
  • 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: 5547808
    Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: August 20, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5543265
    Abstract: Changing (varying, irregular) resist thickness on semiconductor wafers having irregular top surface topography or having different island sizes, affects the percent reflectance (and absorption efficiency) of incident photolithographic light, and consequently the critical dimensions of underlying features being formed (e.g., polysilicon gates). A low solvent content resist solution that can be applied as an aerosol provides a more uniform thickness resist film, eliminating or diminishing photoresist thickness variations. A top antireflective coating (TAR) also aids in uniformizing reflectance, despite resist thickness variations. The two techniques can be used alone, or together. Hence, better control over underlying gate size can be effected, without differential biasing.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 6, 1996
    Assignee: LSI Logic Corporation
    Inventor: Mario Garza
  • Patent number: 5543263
    Abstract: The present invention provides methods for producing photoresist compositions having a very low level of metal ions, utilizing specially treated ion exchange resins. A method is also provided for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: August 6, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Dana L. Durham
  • 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: 5541263
    Abstract: An alkali soluble resin, preferably a phenolic resin, having a portion of its phenolic hydroxyl groups reacted to form a blocking group inert to acid or base. The polymer is used for the formulation of acid hardening photoresists and the presence of the inert blocking group enables development of an exposed photoresist with a strong developer without formation of microbridges between fine line features.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: July 30, 1996
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, George W. Orsula, Mark D. Denison, Roger Sinta, Sheri L. Ablaza
  • 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
  • Patent number: 5532107
    Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and a photosensitive agent, characterized in that the positive resist composition contains, as the photosensitive agent, the quinonediazide sulfonate of at least one of phenolic compounds represented by the following general formulae (I) and (II): ##STR1## wherein R.sub.1 through R.sub.4 mean individually a hydrogen or halogen atom, a hydroxyl group, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.5 denotes a hydrogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or an aryl group with the proviso that the number of hydroxyl groups is 3 or 4; and ##STR2## wherein R.sub.6 through R.sub.9 mean individually a hydrogen or halogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: July 2, 1996
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
  • Patent number: 5532106
    Abstract: A positive-tone photoresist is provided. The photoresist comprises a polymer, a photoactive agent, and a dissolution inhibitor. The dissolution inhibitor comprises a compound of Formula I: ##STR1## wherein R.sub.1 is a C.sub.1 -C.sub.20 alkyl, cyclo alkyl, bensyl, phenyl, alkyl substituted cyclo alkyl, alkoxy substituted cyclo alky, alkyl substituted phenyl, alkoxy substituted phenyl, acetoxy substituted phenyl, hydroxy substituted phenyl, t-butyloxycarbonyloxy substituted phenyl, diphenyl alkyl, alkyl substituted diphenyl, alkoxy substituted diphenyl, alkyl substituted diphenyl alkyl, or alkoxy substituted diphenyl alkyl; and R.sub.2 is a C.sub.1 -C.sub.20 alkyl, cyclo alkyl, benzyl, phenyl, alkyl substituted cyclo alkyl, alkoxy substituted cyclo alkyl, alkyl substituted phenyl, alkoxy substituted phenyl, hydroxy substituted phenyl, acetoxy substituted phenyl, or t-butyloxycarbonyloxy substituted phenyl.The present invention also provides a method of making microelectronic structures.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: July 2, 1996
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Jean M. J. Frechet, Sze-Ming Lee
  • Patent number: 5529882
    Abstract: The present invention provides a positive type photosensitive anionic electrocoating composition having excellent running stability and highly reliable image formability, and a process for pattern formation using said composition. Said composition comprises, as essential components, a resin (A) containing polyethylene glycol or polypropylene glycol chains each having a substituted or unsubstituted phenyl group at the end and a compound (B) containing at least one quinone diazide sulfone unit, and contains carboxyl groups in an amount of 0.2-3 moles per kg (solid content) of the composition.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: June 25, 1996
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Koji Takezoe, Noboru Nakai, Kenji Seko
  • Patent number: 5529881
    Abstract: A positive photoresist composition for super fine working is disclosed, which comprises (a) an alkali-soluble resin and (b) as a photosensitive compound the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid ester of a polyhydroxy compound represented by formula (I) or (II), wherein in a high-speed liquid chromatography measured using a ultraviolet ray of 254 nm, the pattern of the diester component and the pattern of the complete ester component of said 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic acid of the polyhydroxy compound shown by formula (I) or (II) are at least 50% and less than 40%, respectively, of the whole pattern areas; ##STR1## wherein R.sub.1 to R.sub.11, which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group, and R.sub.12 to R.sub.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: June 25, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Sato, Toshiaki Aoai, Kazuya Uenishi
  • Patent number: 5529880
    Abstract: A photoresist that is a mixture of the esterification product of an o-quinonediazide compound and a novolak resin and a high molecular weight phenol having from 2 to 5 phenolic groups and at least 4 diazo naphthoquinone groups. The extent of esterification of the novolak resin is up to 20 percent of the hydroxyl groups and the degree of esterification of the phenol is at least 50 percent of the phenolic hydroxyl groups. The preferred novolak resins are the aromatic novolak resin that are the condensation product of a reactive phenol with a bis(hydroxymethyl)phenol or an aromatic aldehyde, each alone or in the presence of a reactive phenol.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: June 25, 1996
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Peter Trefonas, III
  • Patent number: 5529886
    Abstract: The invention relates to monomers of the formulae R.sup.1 -SO.sub.2 -N(CO-OR.sup.2)-R3-O-CO-CR.sup.4 =CH.sub.2 and R.sup.1 -N(CO-OR.sup.2) -SO.sub.2 -R.sup.3 -O-CO-CR.sup.4 =CH.sub.2, in which R.sup.1 is a (C.sub.1 -C.sub.20)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical, individual methylene groups in the radicals containing alkyl being optionally replaced by heteroatoms, R.sup.2 is a (C.sub.3 -C.sub.11)alkyl, C.sub.3 -C.sub.11) alkenyl or (C.sub.7 -C.sub.11)aralkyl radical, R.sup.3 is an unsubstituted or substituted (C.sub.1 -C.sub.6)alkyl, (C.sub.3 -C.sub.6)cycloalkyl, (C.sub.6 -C.sub.14)aryl or (C.sub.7 -C.sub.20)aralkyl radical and R.sup.4 is a hydrogen atom or a methyl group. It further relates to polymers having at least 5 mol % of units with pendent groups of the formula(e) -R.sup.3 -N(CO-OR.sup.2)-SO.sub.2 -R.sup.1 (I) and/or -R.sup.3 -SO.sub.2 -N(CO-OR.sup.2)-R.sup.
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: June 25, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5523191
    Abstract: There are disclosed novel photoresist compositions employing phosphazene compounds as ballast, unabsorbent of light at a band of i-line and g-line and superior in thermal resistance and sensitivity as well as resolution, characterized by introducing photosensitive groups into phosphazene type ballast represented by the following formula I: ##STR1##
    Type: Grant
    Filed: January 27, 1995
    Date of Patent: June 4, 1996
    Assignee: Korea Kumho Chemical Co., Ltd.
    Inventors: Seong-Ju Kim, Ki-Dae Kim, Hosull Lee, Dae Y. Lee
  • Patent number: 5518864
    Abstract: Disclosed is a photosensitive resin composition, containing a polyamic acid derivative having a repeating unit represented by general formula (1) given below and a photosensitive agent: ##STR1## where, R.sup.1 represents a tetravalent organic group, R.sup.2 represents a divalent organic group, and R.sup.3 and R.sup.4 represent a monovalent organic group, at least one of R.sup.3 and R.sup.4 being an organic group having at least on hydroxyl group bonded to an aromatic ring. A semiconductor substrate is coated with the photosensitive resin composition, followed by exposing the coated film to light through a patterning mask and subsequently applying a development and a heat treatment so as to form a polyimide film pattern. A baking treatment also be applied immediately after the exposure step. The photosensitive resin composition of the present invention performs the function of a positive or negative photoresist film and the function of a polyimide protective film on a semiconductor substrate.
    Type: Grant
    Filed: March 30, 1994
    Date of Patent: May 21, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Masayuki Oba, Rumiko Hayase, Naoko Kihara, Shuzi Hayase, Yukihiro Mikogami, Yoshihiko Nakano, Naohiko Oyasato, Shigeru Matake, Kei Takano
  • Patent number: 5518860
    Abstract: A positive-working photoresist composition comprising a cresol novolac resin as the film-forming agent and a quinonediazido group-containing compound as the photosensitizing agent is admixed with a limited amount of a hydroxyalkyl-substituted pyridine compound so that great improvements can be obtained in the adhesive bonding of the resist layer to the substrate surface and in the stability of the composition by storage still without the problem due to the sublimed material from the resist layer during the patterning process.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: May 21, 1996
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Satoshi Niikura, Jun Koshiyama, Tetsuya Kato, Kouichi Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5518859
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##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, an alkylene ether group, a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: May 21, 1996
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5514520
    Abstract: A photoresist composition consisting of an acid or base generator, a crosslinking agent activated in the presence of an acid or base and an alkali soluble resin, preferably a phenolic resin, having a portion of its phenolic hydroxyl groups reacted to form a blocking group inert to acid or base. The presence of the inert blocking group enables development of an exposed photoresist with a strong developer without formation of microbridges between fine line features.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: May 7, 1996
    Assignee: Shipley Company, L.L.C.
    Inventors: James W. Thackeray, George W. Orsula, Mark D. Denison, Roger Sinta, Sheri L. Ablaza