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WO1990013058A1 - Composes hexahydroxybenzophenone comme activateurs de sensibilite pour melanges sensibles aux rayonnement - Google Patents

Composes hexahydroxybenzophenone comme activateurs de sensibilite pour melanges sensibles aux rayonnement Download PDF

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Publication number
WO1990013058A1
WO1990013058A1 PCT/US1990/001660 US9001660W WO9013058A1 WO 1990013058 A1 WO1990013058 A1 WO 1990013058A1 US 9001660 W US9001660 W US 9001660W WO 9013058 A1 WO9013058 A1 WO 9013058A1
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Prior art keywords
amount
radiation
weight
compound
substrate
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Application number
PCT/US1990/001660
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English (en)
Inventor
Tripunithura V. Jayaraman
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Olin Hunt Specialty Products Inc.
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Application filed by Olin Hunt Specialty Products Inc. filed Critical Olin Hunt Specialty Products Inc.
Publication of WO1990013058A1 publication Critical patent/WO1990013058A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/0226—Quinonediazides characterised by the non-macromolecular additives

Definitions

  • the present invention relates to radiation sensitive mixtures (e.g. those particularly useful as positive-working resist compositions) containing the admixture of an alkali-soluble binder resin, a photoactive compound and an effective sensitivity enhancing amount of a hexahydroxybenzophenone compound all dissolved in a solvent. Furthermore, the present invention also relates to substrates coated with these radiation sensitive mixtures as well as the process of coating, imaging and developing these radiation sensitive mixtures on these substrates. Photoresist compositions are used in microlithographic processes for making miniaturized electronic components such as in the fabrication of integrated circuits and printed wiring board circuitry.
  • a thin coating or film of a photo- resist composition is generally first applied to a substrate material, such as silicon wafers used for making integrated circuits or aluminum or copper plates of printed wiring boards.
  • the preferred method of applying this film is spin coating. By this method, much of the solvent in the photoresist formulation is removed by the spinning operation.
  • the coated substrate is then baked to evaporate any remaining solvent in the photoresist composition and to fix the coating onto the substrate.
  • the baked coated surface of the substrate is next subjected to an image-wise exposure of radiation. This radiation exposure causes a chemical transformation in the exposed areas of the coated surface. Visible light, ultraviolet (UV) light, electron beam, ion beam and X-ray radiant energy are radiation types commonly used today in microlithographic processes.
  • the coated substrate is treated with a developer solution to dissolve and remove either the radiation-exposed or the unexposed areas of the coated surface of the substrate.
  • a developer solution to dissolve and remove either the radiation-exposed or the unexposed areas of the coated surface of the substrate.
  • PEB post-exposure bake
  • treatment of an exposed negative-working resist with a developer solution causes removal of the non-exposed areas of the resist coating and the creation of a negative image in the photoresist coating, and thereby uncovering a desired portion of the underlying substrate surface on which the photoresist composition was deposited but not exposed to the radiation.
  • positive-working photoresist compositions are exposed image-wise to radiation, those areas of the resist composition exposed to the radiation become more soluble to the developer solution (e.g. the Wolff rearrangement reaction of the photoactive compound occurs) while those areas not exposed remain relatively insoluble to the developer solution.
  • treatment of an exposed positive-working resist with the developer solution causes removal of the exposed areas of the resist coating and the creation of a positive image in the photoresist coating.
  • the desired portion of the underlying substrate surface is uncovered where the photoresist was exposed to the radiation.
  • Positive-working photoresist compositions are currently favored over negative-working resists because the former generally have better resolution capabilities and pattern transfer characteristics.
  • the now partially unprotected substrate may be treated with a substrate-etchant solution or plasma gases and the like.
  • This etchant solution or plasma gases etch the portion of the substrate where the photoresist coating was removed during development.
  • the areas of the substrate are protected where the photoresist coating still remains and, thus, an etched pattern is created in the substrate material which corresponds to the photomask used for the image-wise exposure of the radiation.
  • the remaining areas of the photoresist coating may be removed during a stripping operation, leaving a clean etched substrate surface.
  • it is desirable to heat treat the remaining resist layer after the development step and before the etching step to increase its adhesion to the underlying substrate and its resistance to etching solutions.
  • lithographic properties which are critical to positive-working photoresist end-users include the following: (1) good resolution capabilities in both the micron and submicron ranges without incomplete development in the exposed areas (i.e. scumming); (2) higher thermal image deformation temperatures (e.g.
  • sensitivity enhancers also known as photospeed enhancers or speed enhancers
  • resist formulation to increase the solubility of the resist coating in both the exposed and unexposed areas when the speed of development is an overriding processing consideration.
  • some degree of contrast may be sacrificed, e.g., in positive-working resists, while the exposed areas of the resist coating will be more quickly developed, the sensitivity enhancers will also cause a larger loss of the resist coating from the unexposed areas.
  • film defects such as pinholes may be introduced into the coating or subsequent plasma etching steps may cause unwanted break-throughs in the unexposed areas. Accordingly, sensitivity enhancers should provide the desired increased speed of development without too much more film loss in the unexposed areas.
  • Patent Nos. 3,661,582; 4,009,033; 4,036,644; 4,115,128; 4,275,139; 4,365,019; 4,650,745 and 4,738,915 for examples of known sensitivity enhancers. While their known sensitivity enhancers may be suitable for some resist formulation or for some particular end uses, there is a need for new sensitivity enhancers which have better sensitivity enhancement without significant film loss in other resist formulations or in other end uses, or are suitable in a certain combination of resist formulations or a combination of end uses to which the previously known sensitivity enhancers are not suitable. The present invention is believed to be an answer to this need.
  • the present invention is directed to a radiation sensitive composition useful as a positive- working resist characterized by an admixture in a solvent of:
  • At least one alkali-soluble binder resin at least one alkali-soluble binder resin; and (c) an effective sensitivity enhancing amount of at least one hexahydroxybenzophenone compound; the amount of said photoactive compound or compounds being about 5% to about 40% by weight and the amount of said binder resin or resins being about 60% to 95% by weight, based on the total solids content of said radiation sensitive mixture.
  • the present invention also encompasses the process of coating substrates with these radiation sensitive mixtures and their exposing and developing these coated substrates.
  • the present invention encompasses said coated substrates (both before and after imaging) as novel articles of manufacture.
  • the radiation-sensitive compositions of the present invention have three critical ingredients; at least one alkali-soluble binder resin; at least one photoactive compound; and a hexahydroxybenzophenone compoun .
  • binder resins commonly employed in photoresist compositions may be used herein.
  • the preferred class of binder resins is alkali-soluble resin or resins which are useful in positive-working photoresist compositions.
  • alkali-soluble binder resin is used herein to mean a resin which will dissolve completely in an aqueous alkaline developing solution conventionally used with positive-working photoresist compositions.
  • Suitable alkali-soluble resins include phenolic novolaks such as phenol-formaldehyde novolak resins, cresol- formaldehyde novolak resins, or polyvinyl phenol resins, preferably those having an average molecular weight of about 500 to about 40,000, and more preferably from about 800 to 20,000.
  • the novolak resins are preferably prepared by the condensation reaction of phenol or cresols with formaldehyde and are characterized by being light-stable, water-insoluble, alkali-soluble and film-forming.
  • the most preferred class of novolak resins is formed by the condensation reaction between a mixture of meta- and para-cresols with formaldehyde.
  • photoactive compounds which make radiation-sensitive mixtures useful as photoresists may be employed herein.
  • the preferred class of photoactive compounds (sometimes called "sensitizers") is o-quinonediazide compounds, particularly esters derived from polyhydric phenols, alkyl-polyhydroxyphenones, aryl-polyhydroxyphenones, and the like which can contain up to six or more sites for esterification.
  • the most preferred o-quinonediazide esters are derived from
  • 3-diazo-3,4-dihydro-4-oxo-naphthalene-l-sulfonic acid chloride also know as 1,2-naphthoquinonediazide -4-sulfinyl chloride
  • 6-diazo-5,6-dihydro- 5-oxo-naphthalene-l-sulfonic acid chloride also known as l,2-naphthoquinonediazide-5-sulfonyl chloride.
  • resorcinol l,2-naphthoquinonediazide-4-sulfonic acid esters pyrogallol l,2-naphthoquinonediazide-5-sulfonic acid esters, 1,2-quinonediazidesulfonic acid esters of (poly)hydroxyphenyl alkyl ketones or ( ⁇ oly)hydroxyphenyl aryl ketones such as 2,4-dihydroxyphenyl propyl ketone l,2-benzoquinonediazide-4-sulfonic acid esters, 2,4,dihydroxyphenyl hexyl ketone 1,2-naphthoquinone- diazide-4-sulfonic acid esters, 2,4-dihydroxy- benzophenone l,2-naphthoquinonediazide-5-sulfonic acid esters, 2,3,4-trihydroxyphenyl hexyl ketone, l,2-naphthoquinonediazinediazi
  • these materials may be used in combinations of two or more.
  • mixtures of substances formed when less than all esterification sites present on a particular polyhydric phenol, alkyl-polyhydroxyphenone, aryl- polyhydroxyphenone and the like have combined with o-quinonediazides may be effectively utilized in positive acting photoresists.
  • 1,2-quinonediazide compounds mentioned above l,2-naphthoquinonediazide-5-sulfonic acid di-, tri-, tetra-, penta- and hexa-esters of polyhydroxy compounds having at least 2 hydroxyl groups, i.e. about 2 to 6 hydroxyl groups, are one class of preferred compounds.
  • 1,2- naphthoquinonediazide compounds are 2,3,4-trihydroxy- benzophenone 1,2-naphthoquinonediazide—sulfonic acid esters, 2,3,4,4'-tetrahydroxybenzophenone l,2-naphthoquinonediazide-5-sulfonic acid esters, and 2,2' ,4,4'-tetra-hydroxybenzophenone 1,2-naphtho- quinonediazide-5-sulfonic acid esters.
  • Another preferred 1,2-quinonediazide compound is mixed l,2-naphthoquinonediazide-5-sulfonic acid esters of 2,2'3,3'-tetrahydro-3 ,3,3' ,3'-tetramethyl-1,1-spirobi (lH-indene)-5,5'6,6'7,7'-hexol (C.A.S. Reg. No. 32737-33-0).
  • These 1,2-napthoquinonediazide compounds may be used alone or in combination of two or more.
  • the third critical ingredient of the radiation-sensitive composition of the present invention is the hexahydroxybenzophenone compound or mixture of such compounds.
  • the preferred hexahydroxybenzophenone is 2,3,4,3',4* ,5'-hexahydroxybenzophenone.
  • the proportion of the photoactive compound in the radiation-sensitive mixture may range from about 5% to about 40%, more preferably from about 10% to about 25% by weight of the non-volatile (e.g. non-solvent) content of the radiation-sensitive mixture.
  • the proportion of total binder resin of this present invention in the radiation-sensitive mixture may range from about 60% to about 95%, preferably, from about 75% to 90% by weight, of the non-volatile (e.g. excluding solvents) content of the radiation-sensitive mixture.
  • the preferred proportion of hexahydroxy ⁇ benzophenone compound in the radiation-sensitive mixture may range from about 0.5% to about 10%, preferably about 2% to 4% by weight of the non-volatile (e.g., excluding solvents) content of the radiation-sensitive mixture.
  • These radiation-sensitive mixtures may also contain, besides the resin, photoactive compound and hexahydroxybenzophenone compound, conventional photoresist composition ingredients such as other resins, solvents, actinic and contrast dyes, anti-striation agents, plasticizers, other sensitivity enhancers, and the like. These additional ingredients may be added to the binder resin, photoactive compound and hexahydroxybenzophenone compound solution before the solution is coated onto the substrate.
  • the binder resin, photoactive compound or sensitizer, and hexahydroxybenzophenone compound may be dissolved in a solvent or solvents to facilitate their application to the substrate.
  • suitable solvents include methoxyacetoxy propane, toluene, ethyl cellosolve acetate, n-butyl acetate, ethyl lactate, propylene glycol alkyl ether acetates, or mixtures thereof and the like.
  • Cosolvents such as xylene, n-butylacetate, or ethyl ethoxy propionate or the like may also be used.
  • the preferred amount of solvent may be from about 50% to about 500%, or higher, by weight, more preferably, from about 100% to about 400% by weight, based on combined resin, sensitizer, and hexahydroxbenzophenone compound weight.
  • Actinic dyes help provide increased resolution on highly reflective surfaces by inhibiting back scattering of light off the substrate. This back scattering causes the undesirable effect of optical notching, especially on a substrate topography.
  • actinic dyes include those that absorb light energy at approximately 400-460 nm [e.g. Fat Brown B (C.I. No. 12010); Fat Brown RR (C.I. No. 11285); 2-hydroxy-l,4-naphthoquinone (C.I. No. 75480) and Quinoline Yellow A (C.I. No. 47000) and Macrolex
  • Fluoroyellow 10GN C. I. No. Sovent Yellow 16:1
  • those that absorb light energy at approximately 300-340 nm e.g. 2,5-diphenyloxazole (PPO-Chem. Abs. Reg. No. 92-71-7) and 2-(4-biphenyl)-6-phenyl-benzoxazole (PBBO-Chem. Abs. Reg. No. 17064-47-0)].
  • the amount of actinic dyes may be up to 10% weight levels, based on the combined weight of resin and sensitizer.
  • Contrast dyes enhance the visibility of the developed images and facilitate pattern alignment during manufacturing.
  • contrast dye additives that may be used together with the radiation-sensitive mixtures of the present invention include Solvent Red 24 (C.I. No. 26105), Basic Fuchsin (C.I. 42514), Oil Blue N (C.I. No. 61555) and Calco Red A (C.I. No. 26125) up to ⁇ o% weight levels, based on the combined weight of resin and sensitizer.
  • Anti-striation agents level out the photoresist coating or film to a uniform thickness. Anti-striation agents may be used up to five percent by weight levels, based on the combined weight of resin and sensitizer.
  • One suitable class of anti-striation agents is nonionic silicon-modified polymers. Nonionic surfactants may also be used for this purpose. including, for example, nonylphenoxy poly(ethyleneoxy) ethanol; octylphenoxy (ethyleneoxy) ethanol; and dinonyl phenoxy poly(ethyleneoxy) ethanol. Fluorine-substituted nonionic surfactants may also be used for this purpose.
  • Plasticizers improve the coating and adhesion properties of the photoresist composition and better allow for the application of a thin coating or film of photoresist which is smooth and of uniform thickness onto the substrate.
  • Plasticizers which may be used include, for example, phosphoric acid tri-(B- chloroethyl)-ester; stearic acid; dicamphor; polypropylene; acetal resins; phenoxy resins; and alkyl resins up to 10% weight levels, based on the combined weight of resin and sensitizer.
  • Other speed enhancers may be used at weight levels of up to 20%, based on the combined weight of resin and sensitizer. These include, for example, picric acid, nicotinic acid or nitrocinnamic acid.
  • the prepared radiation-sensitive resist mixture can be applied to a substrate by any conventional method used in the photoresist art, including dipping, spraying, whirling and spin coating. Whfen spin coating, for example, the resist mixture can be adjusted as to the percentage of solids content in order to provide a coating of the desired thickness given the type of spinning equipment and spin speed utilized and the amount of time allowed for the spinning process.
  • Suitable substrates include silicon, doped silicon, aluminum, polymeric resins, silicon dioxide, doped silicon dioxide, silicon resins, gallium arsenide, aluminum gallium arsenide, titanium, tantalum, molybdenum, tungsten, titanium suicides, tantalum suicides, molybdenum suicides, tungsten suicides, silicon nitride, copper, polysilicon, ceramics and aluminum/copper mixtures.
  • the photoresist coatings produced by the above described procedure are particularly suitable for application to silicon/silicon dioxide-coated or polysilicon or silicon nitride wafers such as are utilized in the production of microprocessors and other miniaturized integrated circuit components.
  • An aluminum/aluminum oxide wafer can be used as well.
  • the substrate may also comprise various polymeric resins especially transparent polymers such as polyesters and polyolefins.
  • the coated substrate may be preferably baked at approximately 70 ⁇ C to 125°C until substantially all the solvent has evaporated and only a uniform radiation- sensitive coating remains on the substrate.
  • the coated substrate can then be exposed to radiation, in any desired exposure pattern, produced by use of suitable masks, negatives, stencils, templates, and the like.
  • Conventional imaging process or apparatus currently used in processing photoresist-coated substrates may be employed with the present invention. While ultraviolet (UV) light and electron beam radiations are the preferred sources of radiation, other sources such as visible light, ion beam and X-ray radiant energy may be instead used.
  • UV light and electron beam radiations are the preferred sources of radiation
  • other sources such as visible light, ion beam and X-ray radiant energy may be instead used.
  • a post-exposure bake at a temperature about 10°C higher than the soft bake temperature for about 30-300 seconds is used to enhance image quality and resolution.
  • aqueous alkaline developing solution This solution is preferably agitated, for example, by nitrogen gas agitation.
  • aqueous alkaline developers include aqueous solutions of tetra- methylammonium hydroxide, sodium hydroxide, potassium hydroxide, ethanolamine, choline, sodium phosphates, sodium carbonate, sodium metasilicate, and the like.
  • the preferred developers for this invention are aqueous solutions of either alkali metal hydroxides, phosphates or silicates, or mixtures thereof, or tetramethyl- ammonium hydroxide.
  • Alternative development techniques such as spray development or puddle development, or combinations thereof, may also be used.
  • the substrates are allowed to remain in the developer until all of the resist coating has dissolved from the exposed areas. Normally, development times from about 10 seconds to about 3 minutes are employed.
  • the coated wafers After selective dissolution of the coated wafers in the developing solution, they are preferably subjected to a deionized water rinse to fully remove the developer or any remaining undesired portions of the coating and to stop further development.
  • This rinsing operation (which is part of the development process) may be followed by blow drying with filtered air to remove excess water.
  • a post-development heat treatment or bake may then be employed to increase the coating's adhesion and chemical resistance to etching solutions and other substances.
  • the post-development heat treatment can comprise the baking of the coating and substrate below the coating's thermal deformation temperature.
  • the developed substrates may then be treated with a plasma gas etch employing conventional plasma processing parameters (e.g., pressure and gas flow rates) and conventional plasma equipment. Later, the remaining areas of the photoresist coating may be removed from the etched substrate surface by conventional photoresist stripping operations.
  • 2,3,4,3' ,4' ,5'-Hexahydroxybenzophenone [0.84 grams (0.003 mole)] was added to 100 grams of a commercially available resist (HEBR-214-1 available from Olin Hunt Specialty Products Inc. of West Paterson, NJ) consisting of a mixed meta- and para-cresol novolak resin and a naphthoquinone diazide ester photoactive compound in a mixed solvent.
  • the resulting resist composition contained about 27% by weight solids.
  • the resist made according to Part A and a control resist (i.e. HEBR-214 with no additive) were coated on oxidized four inch silicon wafers with a MTC resist spinner at 5000 rpm for 30 seconds and then soft baked at 100°C for 30 minutes in a convection oven.
  • the resulting soft baked resist coatings were measured in Angstroms on a Rudolph Film Thickness Monitor FTM-R using a refractive index of 1.63. These thicknesses are shown in Table 1.
  • the resist coated substrate samples of Part B were then image-wise exposed to an electron beam energy source using a JEOL 845/TM 5500 system at an acceleration voltage of 20 KV at a constant beam current.
  • the electron beam dwell time was varied to obtain various exposure doses at different parts of the coating.
  • the resist coatings on the silicon wafers were developed by immersion for two minutes in diluted WAYCOAT LSI developer (5 parts developer diluted with 4 parts deionized water on a volume basis), then rinsed in deionized water and blow-dried with nitrogen.
  • the developed photoresist coatings were measured for film thickness loss and the sensitivities of the resist of this Example 1 and its control were measured.
  • the film thickness loss measurements were carried out on a Rudolph Film Thickness Monitor FTM-R using a refractive index of 1.63.
  • the sensitivities were carried out on a Rudolph Film Thickness Monitor FTM-R using a refractive index of 1.63.
  • Control 9780 300 30 The data in this Table 1 indicates that the addition of 2,3, ,3', ',5'-hexahydroxybenzophenone increased the electron beam sensitivity of HEBR 214-1 from 30 to 15
  • the resist of this Example 2 was then prepared by adding 0.5 grams of Macrolex Fluoroyellow 10GN dye (available from Mobay Corporation of Pittsburgh, PA) and 1 gram of 2 ,3,4,3',4',5'-hexahydroxybenzophenone to 100 grams of a commercially available resist consisting of a mixed meta- and para-cresol novolak resin and a naphthoquinone diazide ester photoactive compound (HiPR-6517 available from Olin Hunt Specialty Products, Inc. of West Paterson, NJ) and filtered through a 0.2 micron filter.
  • a control resist was also prepared by adding only 0.5 grams of Macrolex Fluoroyellow 10GN dye to 100 grams of this same commercial resist and filtered through a 0.2 micron filter.
  • the resist made according to Part A and the control resist were spin coated onto six inch aluminum wafers at appropriate spin speeds and times to yield 1.8 micron thick films (after soft-baking) using a resist spin coater.
  • the resist-coated substrate samples of Part B were then image-wise exposed with a Canon FPA-1550 Mil G-line stepper having a numerical aperature equal to 0.43.
  • the image-wise exposed resists were post exposure baked at 125°C for 60 seconds on a hot plate.
  • the sensitivity in mJ/cm is shown in Table 2 below to be the amount of energy needed to reproduce the mask pattern at 1 micron geometries.
  • the sensitivity was measured by a Scanning Electron Microscopy (SEM) .

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

Une composition sensible aux rayonnements est caractérisée par l'incorporation dans un solvant de: au moins une résine liante soluble dans l'alcali, au moins un composé photo-actif et une quantité suffisante d'activateur de sensibilité hexahydroxybenzophenone; la quantité de cette résine liante se situant aux environs de 60 à 95 % du poids, la quantité du composé photo-actif se situant aux environs de 5 à 50 % du poids, sur la base du contenu total des solides de cette composition sensible aux rayonnements.
PCT/US1990/001660 1989-04-27 1990-03-30 Composes hexahydroxybenzophenone comme activateurs de sensibilite pour melanges sensibles aux rayonnement WO1990013058A1 (fr)

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US34355589A 1989-04-27 1989-04-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0780730A3 (fr) * 1995-12-22 1998-07-15 Fuji Photo Film Co., Ltd. Plaque d' impression photosensible de type positif

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3661582A (en) * 1970-03-23 1972-05-09 Western Electric Co Additives to positive photoresists which increase the sensitivity thereof
US4275139A (en) * 1978-11-04 1981-06-23 Hoechst Aktiengesellschaft Light-sensitive mixture and copying material produced therefrom
US4365019A (en) * 1981-08-06 1982-12-21 Eastman Kodak Company Positive-working resist quinone diazide containing composition and imaging method having improved development rates
US4594306A (en) * 1975-10-25 1986-06-10 Hoechst Aktiengesellschaft Light-sensitive copying material with o-quinone diazide and phenolic hydroxy compound
US4738915A (en) * 1984-12-14 1988-04-19 Tokyo Ohka Kogyo Co., Ltd. Positive-working O-quinone diazide photoresist composition with 2,3,4-trihydroxybenzophenone
JPS63178228A (ja) * 1987-01-20 1988-07-22 Fuji Photo Film Co Ltd ポジ型フオトレジスト組成物
US4871645A (en) * 1987-06-05 1989-10-03 Fuji Photo Film Co., Ltd. Positive-working photoresist composition

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3661582A (en) * 1970-03-23 1972-05-09 Western Electric Co Additives to positive photoresists which increase the sensitivity thereof
US4594306A (en) * 1975-10-25 1986-06-10 Hoechst Aktiengesellschaft Light-sensitive copying material with o-quinone diazide and phenolic hydroxy compound
US4275139A (en) * 1978-11-04 1981-06-23 Hoechst Aktiengesellschaft Light-sensitive mixture and copying material produced therefrom
US4365019A (en) * 1981-08-06 1982-12-21 Eastman Kodak Company Positive-working resist quinone diazide containing composition and imaging method having improved development rates
US4738915A (en) * 1984-12-14 1988-04-19 Tokyo Ohka Kogyo Co., Ltd. Positive-working O-quinone diazide photoresist composition with 2,3,4-trihydroxybenzophenone
JPS63178228A (ja) * 1987-01-20 1988-07-22 Fuji Photo Film Co Ltd ポジ型フオトレジスト組成物
US4863828A (en) * 1987-01-20 1989-09-05 Fuji Photo Film Co., Ltd. Positive-working o-quinone diazide photoresist composition
US4871645A (en) * 1987-06-05 1989-10-03 Fuji Photo Film Co., Ltd. Positive-working photoresist composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0780730A3 (fr) * 1995-12-22 1998-07-15 Fuji Photo Film Co., Ltd. Plaque d' impression photosensible de type positif

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