EP0258417A1 - Composition de depouillement de photoreserves et procede d'utilisation - Google Patents

Composition de depouillement de photoreserves et procede d'utilisation

Info

Publication number
EP0258417A1
EP0258417A1 EP87901962A EP87901962A EP0258417A1 EP 0258417 A1 EP0258417 A1 EP 0258417A1 EP 87901962 A EP87901962 A EP 87901962A EP 87901962 A EP87901962 A EP 87901962A EP 0258417 A1 EP0258417 A1 EP 0258417A1
Authority
EP
European Patent Office
Prior art keywords
stripping
composition
photoresist
stripping composition
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP87901962A
Other languages
German (de)
English (en)
Inventor
Edwin J. Turner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MacDermid Inc
Original Assignee
MacDermid Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by MacDermid Inc filed Critical MacDermid Inc
Publication of EP0258417A1 publication Critical patent/EP0258417A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen

Definitions

  • This invention relates to improved resist stripping 5 compositions and to processes for stripping resists from substrates using said stripping compositions and is more particularly concerned with stripping compositions comprising a mixture of morpholine or an N-substituted
  • Various types of resist materials are employed to protect selected areas of a substrate, such as a wafer
  • This step is generally accomplished by the use of stripper solvent compositions. It is essen ⁇ tial that the stripper remove the resist completely i.e., without leaving any residue, and that this be done with ⁇ out the necessity for scrubbing or like abrasive tech-
  • the stripping composition be free of any material which could cause corrosion of the substrate or affect the latter deleteriously in any manner.
  • stripper compositions have been 30 disclosed in the prior art.
  • stripper compositions have been described containing one or more components such :- as halogenated hydrocarbons (methylene chloride, tetrachloroethylene) , phenols and phenolic compounds, glycol ethers, ketones (acetone, methylethyl ketone) , dioxane, sulfonic acids and the like.
  • halogenated hydrocarbons methylene chloride, tetrachloroethylene
  • phenols and phenolic compounds glycol ethers, ketones (acetone, methylethyl ketone) , dioxane, sulfonic acids and the like.
  • U.S. Patent 3,075,923 discloses a methylene chloride-based stripper composition containing benzenesulfoni ⁇ acid or an alkylbenzenesulfonic acid as activator.
  • U.S. Patent 4,011,351 describes the removal of polymethacrylate positive resists using solvents such as chloroform, nitromethane, dioxane, formamides and the like.
  • U.S. Patent 4,165,294 teaches the use of stripper compositions comprising a mixture of an alkarylsulfonic acid, a hydrotropic aromatic sulfonic acid and, optional ⁇ ly, a halogen-free aromatic hydrocarbon having a boiling point about 150°C.
  • U.S. Patent 4,165,295 discloses stripper composi ⁇ tions comprising an organic sulfonic acid, in association with a source of fluoride ions, optionally phenol, and a solvent.
  • the solvents listed include N-methylpyrroli- done.
  • Related U.S. Patent 4,215,005 describes stripper compositions comprising an organic sulfonic acid in association with a complex of hydrogen fluoride and a complexing agent of which morpholine is an example.
  • U.S. Patent 4,242,218 teaches the use of an alkarylsulfonic acid in a hydrocarbon solvent which can include chlori ⁇ nated aromatic hydrocarbons. All of the above patents disclose stripper composi ⁇ tions: which are clearly undesirable for use commercially either by reason of exposure of workers to potentially toxic materials or by reason of the difficulty or expense of disposing of the composition in an environmentally acceptable manner after use.
  • compositions containing N-methylpyrroli- done as active ingredient have been described. Illustra ⁇ tively, U.S. Patent 3,673,099 describes a stripper com- position for removing cured resins such as silicones and polyvinylcinnamate from substrates. The composition com ⁇ prises a mixture of N-methyl-2-pyrrolidone, a strong base and optionally ethylene glycol mono-ethyl ether.
  • U.S. Patent 4,276,186 discloses a composition comprising N-methyl-2-pyrrolidone and an alkanolamine for cleaning substrates such as integrated circuit carriers to remove contaminants such as solder flux.
  • U.S. Patent 4,428,871 describes a stripper com ⁇ position which is a mixture of about 55 to 80 percent by weight of pyrrolidone or certain N-substituted pyrroli- dones and about 20 to 45 percent by weight of diethylene glycol monoalkyl ether. It is specifically stated that N-methylpyrrolidone alone has proved not effective as a stripper for certain positive resists and that the mix- tures disclosed in the patent are more effective than either of the components when used alone. The disclosure and experimental data in the patent are confined to the stripping of positive photoresists.
  • the speci ⁇ fication states that the stripper compositions are effective at about 75 ⁇ C or less the bulk of the data was derived using stripping temperatures of 75°C with only 3 exceptions each carried out at 25°C. Of the latter 3 experiments only one resulted in 100 percent removal of photoresist. Further, all the data was derived using -H - photoresists which had been baked at 150°C for 45 minutes to 1 hour. No data is given for photoresists baked at higher temperatures. In actual practice, the photo ⁇ resists are frequently exposed to temperatures signifi- cantly in excess of 150°C and even as high as 220°C, during the processing of substrate to achieve pattern generation using the techniques discussed previously.
  • stripping compositions which contain as the principal active components a mix- ture of (a) morpholine or certain derivatives thereof and (b) pyrrolidone or certain derivatives thereof possess markedly improved properties in terms of their ability to strip a wide variety of resists including resists which have been exposed to processing temperatures of the order of 180°C or higher.
  • These stripper compositions can be employed effectively at temperatures approximating room temperature in most cases and certainly at temperatures which are safely below the flash point of the composi ⁇ tions.
  • Other advantages in these compositions will become apparent form the description and specific exemplification which follows.
  • R and R 1 are independently selected from the group consisting of hydrogen, alkyl from 1 to 3 carbon atoms, inclusive, and hydroxyalkyl from 1 to 3 carbon atoms, inclusive.
  • alkyl from 1 to 3 carbon atoms include ⁇ sive, means methyl, ethyl, propyl and isopropyl. - ⁇ >-
  • hydroxyalkyl from 1 to 3 carbon atoms, inclusive means hydroxymethyl, 1- and 2- hydroxyethyl, 1-, 2- and 3-hydroxypropy1, and 1-hydroxymeth lethyl.
  • the invention also comprises a process for stripp- ing a resist from a substrate after the protective func ⁇ tion of the resist with respect to the substrate has been completed wherein the process comprises employing a stripper composition of the invention to effect the stripping.
  • compositions and process of the invention can be employed to strip a wide variety of resist mate ⁇ rials from a wide variety of substrates known in the art they are particularly adapted for use in stripping posi ⁇ tive photoresists from wafers employed in fabrication of microelectronic circuitry.
  • Illustrative of the latter substrates are silicon wafers whose surface has been treated to form a layer of silicon oxide, aluminum, alloys of aluminum with copper and like metals, chromium, chromium alloys, silicon nitride and the like.
  • the stripper compositions of the invention comprise, as the principal active component, a mixture of a compound of the formula (I) above and a com ⁇ pound of the formula (II) above.
  • the ratio by weight of the compound of formula (I) to the com ⁇ pound of formula (II) is within the range of about 4:1 to about 0.25:1 and preferably is within the range of about 2:1 to about 0.5:1.
  • N-(2-hydroxyethyl)morpholine and the like Illustrative of compounds of the formula (II) above are pyrrolidone, N-methylpyrrolidone, N-ethylpyrrolidone, N-(2-hydroxy- ethyl) pyrrolidone and the like.
  • a preferred stripper composition in accordance with the invention is one which comprises a mixture of morpho ⁇ line and N-methylpyrrolidone in a volume ratio within the ranges set forth above.
  • a particularly preferred range of proportions by weight is about 1:1.
  • compositions of the invention there may also be pre ⁇ sent one or more diluents provided that said diluents are free from corrosive properties, do not attack the sub ⁇ strate, do not present any significant toxicity or environmental hazards, or interfere in any way with the efficacy of the compositions of the invention as resist strippers.
  • diluents can be present in the composi ⁇ tions of the invention in amounts up to about 70 percent by weight based on total weight of the compositions of the invention. The actual amount of such diluents employed in any given instance will vary depending on the relative ease with which the particular resist can be stripped.
  • diluents are polar organic solvents such as glycols of which ethylene glycol, propy- lene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol and the like are typical, glycol mono-alkyl ethers such as the monomethyl, monoethyl, mono- propyl and mono-hexyl ethers of diethylene glycol and dipropylene glycol, glycol esters such as ethyleneglycol mono-acetate, ethyleneglycol diacetate, and the like, and glycol ether esters such as 2-ethoxyethyl acetate (cello- solve acetate), 2-butoxyethyl acetate (butylcellosolve acetate) and the like.
  • polar organic solvents such as glycols of which ethylene glycol, propy- lene glycol, dipropylene glycol, tripropylene glycol, tetrapropylene glycol and the like are typical
  • Particularly advantageous diluents for use in the compositions of the invention are the ono-lower-alkyl ethers of dipropylene glycol.
  • the term "lower-alkyl” means alkyl from 1 to 6 carbon atoms, inclusive, such as methyl, ethyl, propyl, butyl, pentyl, hexyl and isomeric forms thereof.
  • the mono-methyl ether of dipropylene glycol is a particularly preferred diluent.
  • compositions of the invention can also contain water in amounts up to about 70 percent by weight, based on total weight of the composition.
  • the composi ⁇ tions of the invention are preferably substantially free of any water other than that which may be inherently pre ⁇ sent and introduced in association with one or more of the other components. This is particularly the case where the substrate to be stripped is likely to be corroded by exposure to water.
  • compositions of the invention can be employed to strip any of a wide variety of resists, including both positive and negative photoresists, from a substrate after the resist has performed its protective function in respect of the substrate.
  • the stripping of the resist is the final step in a process which includes the following steps.
  • the substrate is first coated with a layer of the resist and an image is developed in the photoresist layer by exposure of the latter to actinic radiation via an appropriate mask followed by removal of the unexposed material (in the case of a negative resist) or the exposed material (in the case of a positive resist) using the appropriate developer.
  • the substrate with photoresist image formed thereon is generally subjected to a post-bake treatment at temperatures up to about- 220°C and or other thermal hardening techniques known in the art as discussed above, before being exposed to pattern generation by any of the procedures known in the art such as etching, ion implantation doping, metal deposition and the like.
  • the step of pattern generation may also give rise to exposure of the resist material to elevated temperatures which can reach as high as about 180°C or even higher.
  • the resist material is stripped from the substrate using a stripping composition of the invention.
  • this stripping can be accomplished in many cases at temperatures approximating ambient tem ⁇ perature (circa 20-25°C) in a relatively short time mea- sured in minutes.
  • relatively high temperatures up to about 180°C or higher
  • the stripper composi ⁇ tion should be employed at elevated temperature up to about 100°C in order that the stripping of the resist can be accomplished completely in a short period of time i.e., of the order of about 10 minutes.
  • the exact temperature and time at which to employ the stripper composition in any given instance is principally a function of the temperature to which the resist has been exposed during post-bake and or other resist hardening techniques and or pattern generation.
  • the temperature of stripping should be less than the flash point of the stripper composition.
  • the flash point of the compositions of the invention is, unlike most prior art strippers, relatively high and of the order of at least about 88°C depending upon the exact formulation employed in the stripper composition.
  • the mode of contacting the stripper composition with the resist to be stripped is not critical. Advantag- eously the resist and substrate is sprayed with or immersed in a bath of the stripper composition which is maintained at the appropriate temperature. Completion of stripping can be readily determined by visual inspection of the substrate if necessary using a microscope or like means.
  • the substrate is washed with water or dilute aqueous solu ⁇ tions of surfactant in order to remove any residual stripper composition, the latter being soluble in, or miscible with, water.
  • positive resists which generally comprise a novolak resin, polyacrylamide or acrylic copolymer resin in association with photosensitizer such as an ester of l-oxo-2-diazo-naphthoquinone-5-sulfonic acid
  • negative resists which generally comprise polyvinylcinnamates, styrene-maleic anhydride and like resins in association with a free radical generating photoinitiator and a photosensitizer
  • other types of resist such as poly- olefinsulfone based resins of which those described in U.S. Patent 4,513,077 are typical.
  • stripper compositions of the invention are particularly well adapted to the stripping of positive photoresists which latter are the type of photoresist most commonly employed in fabricating high resolution geometries in microelectronic applications.
  • the stripping compositions possess a number of advantages over those hitherto employed in the art. Thus they are capable of stripping a wide variety of resists from metallic and other substrates without attacking the substrate or any circuitry or the like which may have been generated on the substrate while the resist was in place " thereon.
  • the compositions pose no significant toxicity hazard to qualified personnel handling the same.
  • the compositions are miscible with water and therefore readily washed from the substrate after the stripping operation has been completed.
  • the compositions possess a relatively high flash point of the order of at least about 88°C which is generally in excess of the temperatures to which the compositions may have to be heated in order to strip the resist.
  • resists can be stripped in a very short time, of the order of several minutes, using bath operating temperatures of the order of 20-25°C, i.e., without the need to employ elevated temperatures.
  • the stripping bath is stable and can be re-used many times over a prolonged period without losing its efficacy. Further the two principal components can be readily recovered by distillation and recycled if and when the bath is finally retired from use.
  • stripper compositions of the invention are effective in most cases at temperatures at, or close to, room temperature, it is possible to use a wide range of engineering materials such as fiberglass reinforced resins, low thermal flow plastics and the like in fabricating the stripping bath and accessories such as ductwork and like installations.
  • Stripping compositions hitherto employed in the art required higher operating temperatures which involved vaporization of solvents and led in many instances to corrosion of ductwork and other equipment with consequent and possibly undesirable contamination of the stripping bath. Operation at temperatures which led to vaporization of stripping elements also caused change in composition of the stripping bath where the latter contained two or more components of different volatility.
  • the following examples illustrate specific embodi ⁇ ments of the compositions and process of the invention and the best mode currently known to the inventors for carrying out the same but are not to be construed as limiting.
  • a silicon wafer with a silicon dioxide coating was spuncoated at 5000 rpm with a high resolution, high contrast, high aspect ratio positive photoresist system comprising a solvent blend solution of a novolak resin and a trihydroxybenzophenone ester of 2-diazo-l-oxo- naphthoquinone ⁇ -sulfonic acid [ULTRAMACtr ⁇ PR914: MacDermid, Inc., Waterbury, Ct.].
  • the resulting coating had an average thickness of 1.2 microns.
  • the coated wafer was baked at 100°C for 30 minutes in a convection oven to evaporate the solvents from the coating before being exposed through a mask to UV light in a broad band contact exposure mode using an Oriel printer.
  • the exposed photoresist was developed using an alkaline developer [ULTRAMAC MF-28: MacDermid Inc.] to give an image of high resolution with walls approaching 90 degrees.
  • the imaged wafer was then baked at 150°C for 30 minutes in a forced air convection oven.
  • the resulting wafer was then immersed in a stripper composition of the invention consisting of a 1:1 mixture by weight of morpholine and N-methylpyrrolidone and having a flash point of 38 ⁇ C.
  • the temperature of the bath was circa 25 ⁇ C. It was found by visual inspection that the photoresist image had been completely stripped from the substrate within 5 minutes after immersion. No damage was found in the substrate itself.
  • Stripper compositions were prepared by admixture of the components shown below in the proportions stated (all parts are percent by volume) .
  • Example 1 The process set forth in Example 1 for preparation and post-baking of a photoresist image on a substrate was repeated exactly as described.
  • the photoresist was com- pletely stripped from the substrate by immersion for 5 minutes at 25°C in a stripper composition of the inven ⁇ tion consisting of a 1:1 by weight admixture of 4-(2-hydr- oxyethyl) morpholine and N-methylpyrrolidone having a flash point of 88°C.
  • the substrate suffered no damage during the stripping.
  • An arsenic implant wafer was prepared as follows. A silicon wafer coated with silicon oxide was spun-coated with a novolak-based positive photoresist (Eastman Kodak EK-820 resist) and soft-baked at 100 ⁇ C before being exposed to actinic radiation via a mask. The image was developed using a proprietary developer [Eastman Kodak EK-809] and post-baked at approximately 150°C. Arsenic implantation was then effected using a beam energy of 140 Kev at 10" 7 Torr with a dosage rate of IO 15 atoms/cm ⁇ . The temperature to which the resist was exposed during this treatment is estimated to be in excess of 200°C making the resist extremely resistant to solvent stripping.
  • the bath temperature was only 30-31 ⁇ C and the extent of stripping under these conditions was. approximately 50 percent.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)

Abstract

Une composition, servant à dépouiller des substrats de leur photoréserve une fois terminée la fonction protectrice de la photoréserve, comprend un mélange (a) de morpholine ou d'un N-alkyle ou N-hydroxyalkylmorpholine et (b) de pyrrolidone ou d'un N-alkyle ou N-hydroxyalkylpyrrolidone, selon une proportion en poids de (a) sur (b) d'environ 4/1 à environ 0,25/1. Ladite composition est efficace dans le dépouillement rapide et complet d'une grande variété de photoréserves à température ambiante ou à des températures élevées se situant au-dessous du point d'inflammabilité de la composition.
EP87901962A 1986-02-28 1987-02-27 Composition de depouillement de photoreserves et procede d'utilisation Withdrawn EP0258417A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83521886A 1986-02-28 1986-02-28
US835218 1986-02-28

Publications (1)

Publication Number Publication Date
EP0258417A1 true EP0258417A1 (fr) 1988-03-09

Family

ID=25268951

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87901962A Withdrawn EP0258417A1 (fr) 1986-02-28 1987-02-27 Composition de depouillement de photoreserves et procede d'utilisation

Country Status (4)

Country Link
EP (1) EP0258417A1 (fr)
AU (1) AU7163187A (fr)
WO (1) WO1987005314A1 (fr)
ZA (1) ZA87922B (fr)

Cited By (1)

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CN110484126A (zh) * 2019-07-16 2019-11-22 福建中安高新材料研究院有限公司 用稀释液减压蒸馏残液制备的大红透明漆及其制备方法

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JP4224651B2 (ja) 1999-02-25 2009-02-18 三菱瓦斯化学株式会社 レジスト剥離剤およびそれを用いた半導体素子の製造方法
JP4810764B2 (ja) * 2001-06-29 2011-11-09 三菱瓦斯化学株式会社 レジスト剥離剤組成物
JP4314320B2 (ja) * 2002-04-10 2009-08-12 三菱電機株式会社 化合物半導体装置の製造方法

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CN110484126A (zh) * 2019-07-16 2019-11-22 福建中安高新材料研究院有限公司 用稀释液减压蒸馏残液制备的大红透明漆及其制备方法
CN110484126B (zh) * 2019-07-16 2021-04-30 福建中安高新材料研究院有限公司 用稀释液减压蒸馏残液制备的大红透明漆及其制备方法

Also Published As

Publication number Publication date
ZA87922B (en) 1987-09-30
WO1987005314A1 (fr) 1987-09-11
AU7163187A (en) 1987-09-28

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