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WO1997034200A1 - Procede de developpement d'une resine photosensible positive - Google Patents

Procede de developpement d'une resine photosensible positive Download PDF

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Publication number
WO1997034200A1
WO1997034200A1 PCT/US1997/003092 US9703092W WO9734200A1 WO 1997034200 A1 WO1997034200 A1 WO 1997034200A1 US 9703092 W US9703092 W US 9703092W WO 9734200 A1 WO9734200 A1 WO 9734200A1
Authority
WO
WIPO (PCT)
Prior art keywords
seconds
developer
development
temperature
photoresist film
Prior art date
Application number
PCT/US1997/003092
Other languages
English (en)
Inventor
William C. Nelson
James Neville Eilbeck
Original Assignee
Hoechst Celanese Corporation
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 Hoechst Celanese Corporation filed Critical Hoechst Celanese Corporation
Publication of WO1997034200A1 publication Critical patent/WO1997034200A1/fr

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Classifications

    • 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
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions
    • 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
    • G03F7/30—Imagewise removal using liquid means

Definitions

  • the present invention relates to the aqueous alkali development of positive photoresist materials used for patterning a positive photoresist coated on a semiconductor wafer, micromachining, printed wire board and the like.
  • Photoresists are well known to those skilled in the art. Generally speaking, they must be sensitive to light so that patterns can be formed in them and they must selectively resist subsequent etching or other processing so that the pattern can be transferred to the underlying substrate.
  • the dominant photoresist system employed in integrated circuit manufacturing today is the novolak/diazonaphthoquinone combination.
  • Diazonaphthoquinones of the class employed in positive photoresists are typically formed by the reaction of a naphthoquinone diazide sulfonyl chloride with a phenolic compound.
  • Reaction products thus formed might include the naphthoquinone (1,2) diazide (5)- sulf ⁇ nyl, naphthoquinone (1,2) diazide (4)-sulfonyl, naphthoquinone (2,1) diazide (5)- sulfonyl, or naphthoquinone (2,1) diazide 4-sulfonyl radicals or mixtures thereof.
  • the sulfonate esters thus synthesized might include the residue of any suitable phenolic compound.
  • These diazides are fairly nonpolar organic molecules that are soluble in organic solvents, but not very soluble in water.
  • diazonaphthoquinone photoactive compounds Upon exposure to light, diazonaphthoquinone photoactive compounds form a polar, base-soluble carboxylic acid in accordance with mechanisms known to skilled artisans.
  • the exposed photoactive compound is relatively soluble, while the unexposed photo active compound is relatively insoluble; creating a solubility difference which forms the basis of image formation.
  • positive photoresist compositions generally include a phenol-formaldehyde resin of the Novolak class or sometimes a hydroxystyrene polymer such as poly(4-hydroxystyrene).
  • a phenol-formaldehyde resin of the Novolak class or sometimes a hydroxystyrene polymer such as poly(4-hydroxystyrene).
  • Other polymeric components including styrene, methyl styrene, styrene-maleic anhydride components in combination with the foregoing may also be employed. See, generally,
  • a method of developing a positive photoresist film subsequent to exposure includes applying the developer to the photoresist on the substrate at a specified and desired normality, and developing the exposed photoresist at a specified and desired temperature for a specified and desired development time to achieve the desired performance characteristics of the photoresist developer system.
  • the basic and novel characteristics of the process are that the performance characteristics, e.g. contrast, for a given photoresist composition developed using a given developer and a given development process, are overwhelmingly the function of the developer normality, the development temperature and the development time.
  • a single developer such as that supplied from a central supply system, can be used to produce a variety of performance parameters, extremely high contrast or resolution on the one hand, or high throughput (high photospeed) on the other hand.
  • a suitable temperature range for development is from about 15°C to about 40°C perferably from about 20°C to about 30°C, preferably for from about 20 seconds to about 180 seconds, more preferably from about 40 seconds to about 80 seconds.. Use of the present process allows one to control developer performance characteristics, without the addition of a surfactant.
  • the present invention specifically relates to a process for improving the contrast and resolution of a positive photoresist, the process consisting essentially of coating a positive photoresist film on a substrate, exposing the photoresist film on the substrate to actinic radiation, baking the photoresist film after exposure to actinic radiation (post exposure baking) at a temperature of from about 120°C to about 160°C, more preferably from about 130°C to about 150°C, for a period of time of from about 5 seconds to about 30 seconds, more preferably from about 5 seconds to about 20 seconds, and developing the photoresist film with a single developer, wherein for a constant Normality developer, the contrast and resolution are improved by increasing the development temperature, while maintaining the development temperature within the range of from about 15°C to about 40°C, preferably from about 20°C to about 30°C, and/or increasing the time of development while mamtaining the time of development within the range of from about 20 seconds to about 180 seconds, preferably from about 40 seconds to about 80 seconds.
  • the present invention also relates to a process for improving the photospeed of a positive photoresist, the process consisting essentially of coating a positive photoresist film on a substrate, exposing the photoresist film on the substrate to actinic radiation, baking the photoresist after exposure to actinic radiation (post exposure baking) at a temperature of from about 120°C to about 160°C, preferably from about 130°C to about
  • the photospeed is improved by decreasing the development temperature, while maintaining the development temperature within the range of from about 15°C to about 40°C, preferably from about 20°C to about 30°C while maintaining the time of development within range of from about 20 to about 180 seconds, preferably from about 40 seconds to about 80 seconds.
  • the developer utilized in the present process preferably has a Normality of from about 0.15 to about 0.5, preferably from about 0.2 to about 0.35.
  • the present invention is described in detail below with reference to the examples provided for purposes of illustration and not by way of limitation. Modifications to specific embodiments will be readily apparent to those skilled in the art, which modifications are within the spirit and scope of the present invention as herealter claimed.
  • the base is from about 0.15 to about 0.5 Normal (N) in the hydroxide component, about 0.2 to about 0.35 N being more typical, with about 0.261 N being preferred as an industry standard.
  • the development temperatures are between about 15°C and about 40°C, preferably from about 20°C to about 30°C, typically about 25°C.
  • the time for development is preferably from about 20 seconds to about 180 seconds, more preferably from about 40 seconds to about 80 seconds.
  • the classical remedy for improving developer performance is to in corporate a surfactant into the developer composition. This has the effect of lowering the surface tension at the interface between the developer and the surface of the exposed photoresist film deposited on the substrate. Good wetability results in reduced amounts of developer being required to develop the image.
  • the process of the present invention allows the use of non-surfactant developers to increase the wetability of the surface of the photoresist to be developed. Without surfactant, the development of fine lines is not acceptably achieved, normally because of the formation of web-like configurations between the lines (webbing) at the end of the development. This results in whole areas appearing to either have not started to develop or to be in the initial stages of the development process.
  • the present process provides a substantial reduction in the surface tension at the developer/photoresist interface which results in the substantial absence of webbing, and vastly improved CD control.
  • PEB post exposure bake
  • the process of the present invention is an effective method for substantially improving the performance of the photoresist by controling the normality of the developer, and the development temperature and time.
  • the ammonium hydroxide component may be tetramethylammonium hydroxide (TMAH), trimethylethanol ammonium hydroxide (choline), tetra(2-hydroxyethyl) ammonium hydroxide, mixtures thereof or like compounds.
  • TMAH tetramethylammonium hydroxide
  • choline trimethylethanol ammonium hydroxide
  • TMAH is particularly preferred, while other ammonium hydroxide compounds may be employed if so desired.
  • any positive photoresist substrate ⁇ u ⁇ e suitable the inventive process is particularly applicable to photoresist comp .aons containing a phenol-formaldehyde resin known as a Novolak resin and a diazonaphthoquinone photoactive compound.
  • the terminology "consists essentially of refers to the fact that the developing process of the present invention does not require substantial steps other than applying the developer at a suitable temperature and rinsing it away after a suitable time interval. This is contrasted with the process disclosed by Japanese Application 05181286-A which describes a two-step developing process using a developer first at a higher temperature then at a lower temperature. Similarly, IP 95021640 teaches the use of various developers at a single temperature. Other patents such as JP 58102942 and US 5342738 teach that constant temperature is important. Finally, US 5474877 teaches that heating the substrate while applying the developer.
  • the present invention teaches using a single developer, such as would be used in a modem semiconductor factory, supplied from a central storage tank, and that the process contrast of the developer can be altered by merely changing the developer temperature during the develop cycle, in such a manner as to give performance similar to using multiple concentrations of developers at varying normalities.
  • This photoresist film was image-wise exposed on a Nikon® 1755i7B Nikon Stepper equipped with a 0.54 NA lens using a reticule with varying line-space dimensions.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

Procédé permettant d'améliorer le contraste, la résolution et la photosensibilité d'une résine photosensible positive, dans lequel on applique une couche de résine photosensible sur un substrat, on expose ladite couche à un rayonnement actinique, on la cuit après exposition au rayonnement actinique, puis on la développe avec un seul révélateur. Pour un révélateur à normalité constante, on améliore le contraste et la résolution en augmentant la température et/ou le temps de développement, tandis qu'on améliore la photosensibilité en diminuant la température et/ou le temps de développement.
PCT/US1997/003092 1996-03-12 1997-02-28 Procede de developpement d'une resine photosensible positive WO1997034200A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US1328796P 1996-03-12 1996-03-12
US60/013,287 1996-03-12

Publications (1)

Publication Number Publication Date
WO1997034200A1 true WO1997034200A1 (fr) 1997-09-18

Family

ID=21759190

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/003092 WO1997034200A1 (fr) 1996-03-12 1997-02-28 Procede de developpement d'une resine photosensible positive

Country Status (1)

Country Link
WO (1) WO1997034200A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7846648B2 (en) * 2003-12-18 2010-12-07 Tokyo Electron Limited Substrate developing method, substrate processing method and developing solution supply nozzle

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0195315A2 (fr) * 1985-03-11 1986-09-24 Hoechst Celanese Corporation Procédé pour la fabrication de photoréserves structurées
US4784937A (en) * 1985-08-06 1988-11-15 Tokyo Ohka Kogyo Co., Ltd. Developing solution for positive-working photoresist comprising a metal ion free organic base and an anionic surfactant
JPH03196516A (ja) * 1989-12-25 1991-08-28 Nec Corp レジストパターンの現像方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0195315A2 (fr) * 1985-03-11 1986-09-24 Hoechst Celanese Corporation Procédé pour la fabrication de photoréserves structurées
US4784937A (en) * 1985-08-06 1988-11-15 Tokyo Ohka Kogyo Co., Ltd. Developing solution for positive-working photoresist comprising a metal ion free organic base and an anionic surfactant
JPH03196516A (ja) * 1989-12-25 1991-08-28 Nec Corp レジストパターンの現像方法

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "Resist Development Process. August 1980.", IBM TECHNICAL DISCLOSURE BULLETIN, vol. 23, no. 3, August 1980 (1980-08-01), NEW YORK, US, pages 1003, XP002035219 *
PATENT ABSTRACTS OF JAPAN vol. 015, no. 459 (E - 1136) 21 November 1991 (1991-11-21) *
SPAK M A: "High temperature post exposure bake (HTPEB) for AZ 4000 photoresist", ADVANCES IN RESIST TECHNOLOGY AND PROCESSING II, SANTA CLARA, CA, USA, 11-12 MARCH 1985, ISSN 0277-786X, PROCEEDINGS OF THE SPIE - THE INTERNATIONAL SOCIETY FOR OPTICAL ENGINEERING, 1985, USA, PAGE(S) 299 - 307, XP000677800 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7846648B2 (en) * 2003-12-18 2010-12-07 Tokyo Electron Limited Substrate developing method, substrate processing method and developing solution supply nozzle
US20110027727A1 (en) * 2003-12-18 2011-02-03 Tokyo Electron Limited Substrate developing method, substrate processing method and developing solution supply nozzle
US8415092B2 (en) * 2003-12-18 2013-04-09 Tokyo Electron Limited Substrate developing method, substrate processing method and developing solution supply nozzle

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