EP0556177A1 - Revetement superficiel pour vernis a masquer catalyses par acide - Google Patents

Revetement superficiel pour vernis a masquer catalyses par acide

Info

Publication number
EP0556177A1
EP0556177A1 EP19910906782 EP91906782A EP0556177A1 EP 0556177 A1 EP0556177 A1 EP 0556177A1 EP 19910906782 EP19910906782 EP 19910906782 EP 91906782 A EP91906782 A EP 91906782A EP 0556177 A1 EP0556177 A1 EP 0556177A1
Authority
EP
European Patent Office
Prior art keywords
acid
resist
polymeric film
film forming
acid catalyzed
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Withdrawn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
EP19910906782
Other languages
German (de)
English (en)
Inventor
Willard Earl Conley
Ranee Wai-Ling Kwong
Richard Joseph Kvitek
Robert Neal Lang
Christopher Francis Lyons
Steve Seiichi Miura
Wayne Martin Moreau
Harbans Singh Sachdev
Robert Lavin Wood
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.)
International Business Machines Corp
Original Assignee
International Business Machines Corp
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 International Business Machines Corp filed Critical International Business Machines Corp
Publication of EP0556177A1 publication Critical patent/EP0556177A1/fr
Withdrawn legal-status Critical Current

Links

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
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/092—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means

Definitions

  • the invention relates to acid catalyzed resist formulations. More particularly, the present invention is concerned with a protective topcoat material for use as an overcoating film for acid catalyzed resist compositions.
  • U.S. Patent No. 3,753,715 discloses the use of certain water soluble macromolecular organic polymers in controlling oxygen diffusion in photopolymerizable copying process.
  • the barrier materials include polyvinyl alcohol and its partial esters, and partial acetals, as well as other natural and synthetic materials of higher molecular weights such as gelatin, gum arabi ⁇ , copolymer of methylvinyl ether and maleic anhydride, polyvinyl pyrrolidones, and water soluble polymers of ethylene oxide with molecular weights in the range from 100,000 to 3,000,000. Wetting agents in relatively small quantities have been included in such aqueous coating solutions.
  • the drawbacks of such barrier materials include the necessity for certain minimum drying times to form homogeneous coatings and the impermeability of the layers to light that an effective oxygen transfer cannot be maintained.
  • U.S. Patent No. 3,652,273 discloses the use of polyvinyl butyral as a topcoat for photoresist. This topcoat provides protection against oxygen and high humidity and results in less scumming of and pinholing in the hydrophobic resist. The topcoat film is soluble in the developer and does not interfere with imaging.
  • U.S. Patent No. 4,756,988 discloses the use of a non-photosensitive crosslinkable adhesive layer to provide performance improvements in the areas of resistance to crazing of the film during storage, photosensitivity in that the photospeed is increased to make the films more processable, enabling the fabrication of photoresists without using alkoxysilane adhesion promoters, and improving thermal dimensional stability of the film during
  • the topcoat compositions include terpolymers of ethylacrylate, methylacrylate and acrylic acid.
  • IBM Technical Disclosure Bulletin, Vol. 12, No. 9, pp. 1418-19, discloses the use of azidosulfono-stilbene films as a topcoat to prevent oxygen diffusion into photoresist films to consume sensitizer radicals.
  • the polyvinyl acetate impedes oxygen diffusion.
  • Japanese Patent Publication 58-178340 is directed to a process for forming images by exposing a photosensitive material prepared by coating a substrate with a photosensitive layer and a protective layer of polyvinyl alcohol which is water insoluble but is water swellable after exposure to light, removing the polyvinyl alcohol layer with water and developing the photosensitive layer.
  • European Patent Application 0160468 is directed to the use of a number of materials including polyethylene oxide as a protective topcoat against ozone generated in a flexographic printing process.
  • the use of this topcoat leads to the improved adhesion of inks to corona treated cardboard.
  • Japanese Patent Publication No. 60 200249 relates to the use of a polyvinyl alcohol as an antisticking layer between a topcoat layer and a photosensitive layer on a substrate.
  • p 6521 discloses the use of polyvinyl alcohol as a top depth-of-focus enhancement layer owing to the optical properties of the polyvinyl alcohol film. No suggestion of barrier properties is made.
  • Acid catalyzed resists are based upon mechanisms which involve the radiation induced generation of a Lewis or Bronsted acid from acid precursors such as sulfonates and triflates of onium salts and oxime and dicarboximide derivatives.
  • the radiation induced formation of acid catalyzes the decarbonylation of the resist such as the poly-p-tertbutyloxycarbonyloxystyrene compositions as set forth in U.S. Patent No. 4,491,628.
  • Other acid catalyzed reactions include the cleaving of diacetals of novolaks and the acid catalyzed crosslinking of epoxy and melamine based resists.
  • acid catalyzed image amplified resist are very reactive compositions, i.e., they have a high photospeed, they also exhibit an extreme sensitivity to environmental chemicals present in the process areas, even when they are present only at the p.p.b. level. If wafers having an imaged and exposed acid catalyzed resist such as poly-p-tertbutyloxycarbonyloxystyrene are left open to process air, they suffer from profile deterioration and eventually no discernible images will be formed. The desensitization of the resist is believed to be due to the poisoning of the acid generator and the acids formed by the absorption of vapors of organic amines and/or inorganic bases.
  • compositions were exposed to ppb levels of organic vapors of N-methyl-2-pyrrolidone(NMP) , ammonia, pyridine and triethylamine and rapid desensitization of the resists was noted. Since these resists are sensitive to organic vapors at the ppb levels, it is not practical or economical to remove all of these vapors from a manufacturing process area or from inside of those tools, designed to operate at atmospheric conditions. Additionally, a wafer may be exposed to process air for up to 15 minutes inside a deep UV stepper or scanning tool. Different portions of large wafers, e.g., 200 mm diameter wafers may experience different periods of exposure to process air. Desensitization may cause certain portions of the wafer to be undeveloped or have localized distorted images.
  • the barrier layer has also been found to increase the sensitivity of coated acid sensitized resists when such resists are used in electron beam tools. Uncoated resists tend to experience an outgassing of acid and acid-degraded fragments due to their partial pressures.
  • the use of the barrier inhibits the removal of acid from the resist film and, therefore, enhances the effect of the acid in promoting the patterned exposure.
  • Barrier topcoats have been previously used to protect free radical based resist systems which are oxygen sensitive. These include a 25 um Mylar film on DuPont Riston acrylate crosslinking resist and the use of 2 um film of polyvinylalcohol on top of a free radical polyolefin sulfone-novolak based x-ray resist. For such uses, films of polyvinylalcohol thinner than about 0.5um does not function as an -6- effective oxygen barrier topcoat. The thicker barriers are thought to prevent oxygen from diffusing into the exposed resist films and consuming some or all of the radical initiators. Topcoats which
  • a protective topcoat has to be thin and permeable in order to allow the gaseous reaction products formed during post exposure bake to diffuse through the resist and the topcoat film without bubble formation or distortion of the
  • topcoat (2) a low sodium metal or ammonium ion content ⁇ 100 ppm.
  • Metallic or basic impurities in topcoat can desensitize the acid formed during exposure;
  • Example 1 A lym film on silicon wafer of an acid catalyzed resist comprising poly-, p-tertbutyloxycarbonyloxystyrene resist containing 4% by weight of triphenysulfonium hexafluoroantimonate made in accordance with the method set forth in U.S. Patent 4,491,628 was exposed on Perkin-Elmer deep UV scanner (200-290 nm exposure band) and left standing for several minutes in a lab before post-exposure baking. After post expose baking and development in anisole, the 1 um lines of resist images were found to have overhanging "T" shapes.
  • a companion wafer processed with a topcoat of 100 nm of polyvinylbutyral cast from butanol was found to form good straight wall profiles without "T" overhangs. hen the uncoated resist was exposed to longer periods of time of process air (25 hours) no images were formed in the uncoated resist film and only slight traces of overhang formation in the polyvinylbutyral topcoated acid catalyzed resist. A protection time of 30 minutes is considered adequate for even the slowest exposure tools.
  • Example 2 - A l.O ⁇ m film on silicon wafer of an acid catalyzed resist comprising a partially t-butyloxycarbonyloxylated poly-p-hydroxystyrene sensitized with 8% MDT was exposed by Perkin-Elmer
  • Example 3 A 1.0 y m film on a silicon wafer of the partially t-butyloxycarbonyloxylated poly-p-hydroxystyrene sensitized with MDT was exposed at 2.5 ⁇ C/c with a 25 KeV electrons. A faint image which was not developed out was formed. A similar
  • Example 4 A l.O ⁇ m film on silicon of Ray PF
  • topcoat polymeric materials which have the properties and performances as here set forth are within the teaching of the present invention and within its scope as set forth in the claims which follow.

Landscapes

  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Materials For Photolithography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

Matériau protecteur destiné à être utilisé en tant que couche de revêtement pour des compositions de vernis à masquer catalysés par acide comprenant un composé polymère filmogène dont les couches sont imperméables aux vapeurs de bases organiques et inorganiques.
EP19910906782 1990-09-18 1990-12-21 Revetement superficiel pour vernis a masquer catalyses par acide Withdrawn EP0556177A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58727390A 1990-09-18 1990-09-18
US587273 2004-07-12

Publications (1)

Publication Number Publication Date
EP0556177A1 true EP0556177A1 (fr) 1993-08-25

Family

ID=24349129

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19910906782 Withdrawn EP0556177A1 (fr) 1990-09-18 1990-12-21 Revetement superficiel pour vernis a masquer catalyses par acide

Country Status (4)

Country Link
EP (1) EP0556177A1 (fr)
JP (1) JPH05507154A (fr)
CA (1) CA2090039A1 (fr)
WO (1) WO1992005474A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5506090A (en) * 1994-09-23 1996-04-09 Minnesota Mining And Manufacturing Company Process for making shoot and run printing plates
US6984482B2 (en) 1999-06-03 2006-01-10 Hynix Semiconductor Inc. Top-coating composition for photoresist and process for forming fine pattern using the same
KR100401116B1 (ko) * 1999-06-03 2003-10-10 주식회사 하이닉스반도체 아민오염방지 물질 및 이를 이용한 미세패턴 형성방법
DE102004030861A1 (de) * 2004-06-25 2006-01-19 Infineon Technologies Ag Verfahren zum Strukturieren eines Halbleitersubstrats unter Verwendung einer Schutzschicht, die das Ausgasen während der Belichtung verringert oder verhindert
KR100966197B1 (ko) 2004-12-03 2010-06-25 제이에스알 가부시끼가이샤 반사 방지막 형성용 조성물, 적층체 및 레지스트 패턴의형성 방법
JP4595606B2 (ja) 2005-03-17 2010-12-08 Ｊｓｒ株式会社 反射防止膜形成用組成物、積層体およびレジストパターンの形成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50152803A (fr) * 1974-05-29 1975-12-09
JPS57183030A (en) * 1981-05-07 1982-11-11 Toshiba Corp Manufacture of semiconductor device
DE3715790A1 (de) * 1987-05-12 1988-11-24 Hoechst Ag Strahlungsempfindliches aufzeichnungsmaterial

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9205474A1 *

Also Published As

Publication number Publication date
WO1992005474A1 (fr) 1992-04-02
CA2090039A1 (fr) 1992-03-19
JPH05507154A (ja) 1993-10-14

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