WO1994011788A1 - Procede de production de microstructures - Google Patents

Procede de production de microstructures Download PDF

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Publication number
WO1994011788A1
WO1994011788A1 PCT/NL1993/000240 NL9300240W WO9411788A1 WO 1994011788 A1 WO1994011788 A1 WO 1994011788A1 NL 9300240 W NL9300240 W NL 9300240W WO 9411788 A1 WO9411788 A1 WO 9411788A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
siliceous
polymers
side groups
group
Prior art date
Application number
PCT/NL1993/000240
Other languages
English (en)
Inventor
Emile Willebrordus Jacobus Marie Van Der Drift
Johan Christoph Van De Grampel
Robert Puyenbroek
Bernard André Corneille ROUSSEEUW
Original Assignee
Technische Universiteit Delft
Rijksuniversiteit Te Groningen
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 Technische Universiteit Delft, Rijksuniversiteit Te Groningen filed Critical Technische Universiteit Delft
Priority to AU56599/94A priority Critical patent/AU5659994A/en
Publication of WO1994011788A1 publication Critical patent/WO1994011788A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/148—Polysiloxanes
    • 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
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • 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
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
    • H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
    • H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
    • H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
    • H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
    • H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials

Definitions

  • the invention relates to a method of providing a microstructure in electric conductors, semiconductors and insulators utilizing a multilayer resist system, to a multilayer resist system having positive and/or negative tone for producing microstructures, and to siliceous polymers suitable therefor.
  • Resists with a catalyzed exposure reaction are subtantially purely organochemical polymers.
  • a so-called initiator is added to the polymer .
  • an irradiated quantum for instance a photon or an electron
  • a reactive product for instance a proton
  • This so-called chemical amplification has been developed in all sorts of forms.
  • the most common variant is the acid-catalyzed exposure reaction in which a H + ion is formed by exposure, subsequently effecting a multiplicity of polymer conversions. Positive as well as negative resists have been realized.
  • the initiators have been designed such that the exposure reaction can be effected by photons (deep UV) , electrons or X-ray quanta. All ⁇ these resists are used in a one-layer mask and are not suitable for the ultra-high resolution which can be realized in multilayer approaches.
  • Siliceous resist systems are based on the principle that after exposure, silicon is selectively left behind in the top layer of the mask. This may take place in a two-layer configuration, wherein the bottom layer is an organoche ical polymer and the top layer consists of a siliceous polymer, via exposure, the pattern is generated in the top layer.
  • this is also possible in a one-layer configuration, wherein, after exposure of a normal organochemical resist sytem, silicon-containing molecules are selectively incorporated into the unexposed surfaces by exposure to suitable vapors or liquids.
  • an oxygen plasma follows, with the non-siliceous portions being etched in the plasma and the siliceous portions remaining unaffected with a high lateral precision.
  • siliceous resists have been developed on the basis of polysiloxanes which have an excellent etching resistance due to the high silicon content, but which are not very sensitive from a lithographic viewpoint. These resist systems all have a negative tone: what is exposed will remain unaffected after development.
  • siliceous polymers have been synthesized wherein the main chain is purely organic and the silicon is incorporated via side chains. These polymers may have an excellent sensitivity, but the etching resistance is insufficient because of the relatively low silicon content. In this class, both positive and negative resists have been realized.
  • the imaging function and the actual mask function are separated in two separate layers, with the advantage that a superior resolution is obtained.
  • the procedure of a two-layer mask is as follows (se also Fig. l) : after exposure and development of the pattern i the top (image) layer, the pattern is subsequently transferred, via dry-etching in oxygen plasmas, into the bottom mask layer with a lateral precision of ca. 5 nm. After this, the actual pattern transfer into the underlying materia layer can take place in plasmas containing fluorine (F) and/o chlorine (Cl) .
  • F fluorine
  • Cl chlorine
  • the following main characteristics are essential to the top layer: l. High sensitivity and high contrast during the pattern definition; 2. High etching resistance to oxygen plasmas during the pattern transfer.
  • the object of the invention is to provide siliceous resist systems for two-layer mask purposes, having:
  • a next object is the realization of resists having a positive and/or negative tone, depending on the polarity of the developer. More particularly, the present invention is directed to the lithographic action of new siliceous resist systems for microfabrication. These systems are both resist systems having a positive tone and resist systems having a negative tone or a combination of the two.
  • the invention relates to a method of providing a microstructure in electric conductors, semiconductors and insulators utilizing a multilayer resist system, wherein in the image layer a siliceous polymer, comprising chemically unstable side groups, and an initiator are used, which initiator generates, under the influence of radiation, a catalyst which in turn chemically modifies these side groups, the silicon content of this polymer being such that upon treatment with oxygen plasm a closed network of silica is formed on the surface of the polymer.
  • the invention relates to a multilayer resist system having positive and/or negative tone for producing microstructures, characterized in that the image layer contains a siliceous polymer comprising chemically unstable side groups, and an initiator, which initiator, under the influence of radiation, generates a catalyst, which in turn modifies these side groups, the silicon content of this polymer being such that upon treatment with oxygen plasma a closed network of silica is formed on the surface of the polymer.
  • the invention relates to three groups of new polymers which are suitable for use in the first two aspects of the invention.
  • the invention is based on, for instance, the use of the specific polymers in microlithography, one of the essential aspects being that under the influence of a catalyzed exposure reaction, one or more groups are modified chemically in the siliceous polymer, after which, by means of a suitable developer, the exposed or, conversely, the unexposed portion can be removed.
  • siliceous polymer Another important aspect of the siliceous polymer is that the silicon content is so high that upon treatment with oxygen plasma, as is also used for etching, a substantially closed network of silica is formed.
  • a layer of silica is formed at the surface of the mask.
  • a first group consists of the polymers having a SiO main chain, having attachted thereto the , wherein
  • a second group also has a SiO-based structure, but in the form of a so-called ladder polymer (formula 13) , wherein R represents a dihydropyrane or a methoxy- dihydropyrane group.
  • a third group consists of organochemical copolymers having chemically unstable side groups and siloxane macromers grafted thereon.
  • siloxane macromers or siliceous macromers siloxane polymers are meant that can be grafted on the main chain.
  • An example thereof is the compound of formula 8 of the formulae sheet, wherein n is an integer indicating the degree of polymerization of the siloxane. The amount of silicon in the polymer is of importance to the properties thereof.
  • Suitable monomers containing unstable side groups are the monomers such as the modified styrenes (4-t-butoxy- carbonyloxystyrene, or 4-t-butoxystyrene) , or t-butyl methacrylate, but it is also possible to use, for instance, a monomer containing a glycidyl group, such as glycidyl methacrylate. Examples of suitable combinations of monomers in a polymer of this third group are given in formulae 9-12 and 14 of the formulae sheet.
  • the indicated components in the copolymers will be randomly present in the copolymer, v, x and y indicating the molar proportions of each monomer in the copolymer.
  • m equals 0 or 1, i.e. the formula relates both to 4-t-butoxycarbonyloxy and to 4-t- butoxystyrene.
  • the side chains comprise unstable chemical groups, such as, for instance t-butoxy groups, or t- butoxycarbonyloxy groups or epoxy groups, producing a positiv and/or negative tone on the basis of a catalyzed exposure reaction.
  • these chemically unstable side groups can take place in various manners.
  • this can for instance be effected through hydrosilylation of a polyhydrosiloxane with a suitable , ⁇ -unsaturated compound, for instance 4-t-butoxycarbonyloxy- styrene, 4-t-butoxystyrene or t-butyl methacrylate.
  • a suitable , ⁇ -unsaturated compound for instance 4-t-butoxycarbonyloxy- styrene, 4-t-butoxystyrene or t-butyl methacrylate.
  • the addition of this ⁇ , ⁇ -unsaturated compound can take place both via the ⁇ and via the ⁇ carbon, resulting in the two given meanings of the term A in for instance formula 3.
  • the chemically unstable group can later be attached to the main chain, or, preferably, a monomer containing the chemically unstable side group can be polymerized into the main chain.
  • the side group containing silicon macromer (or siliceous macromonomer) can simultaneously be incorporated as comonomer, but it is also possible to graft the macromer on the main chain later.
  • other substantially non-reactive monomers can be incorporated as well to improve the properties of the polymer. Suitable monomers are for instance styrene, cc-methylstyrene, bromostyrene, acrylates, methacrylates and other ⁇ , ⁇ -unsaturated compounds.
  • the initiator Another component of the top layer is the initiator. Under the influence of radiation, this initiator should generate a catalyst, which catalyzes a multiplicity of conversions in the polymer. Such catalysts are known per se, for instance for the use in one-layer masks with completely organochemical polymers. According to the invention, preferably an initiator is used generating a catalyst for the acid-catalyzed chemical amplification. Examples of such initiators are sulfonium salts or iodonium salts.
  • Tetrahydrofuran (THF) (Janssen) is dried on molecular sieves (4A) and subsequently distilled from sodium/benzophenone under nitrogen.
  • Toluene (Janssen) is dried on sodium and distilled from this drying agent under nitrogen.
  • Diethyl ether is dried with anhydrous calcium chloride and subsequently distilled from sodium under nitrogen.
  • n-Hexane (Merck) is dried on sodium and subsequently distilled from sodium under nitrogen.
  • the p.a. solvents 2-propanol (Merck) , methanol (Merck) , chloroform (Merck) and dichloromethane (Merck) are used as received.
  • TBCS 4-1-Butoxycarbonyloxystyrene
  • TBCS 4-1-Butoxycarbonyloxystyrene
  • p-Bromostyrene (Janssen) is used as obtained, t-Butyl methacrylate (TBMA, formula 5) (Tokyo Kasei Kogyo Co.) is distilled in vacuum over calcium hydride and stored under nitrogen at -20 °C. Glycidyl methacrylate (GMA) (Janssen) is distilled in vacuum over calcium hydride. Benzoyl peroxide (BPO) (Aldrich) is used as obtained. The liquids 3,4 dihydro-2H-pyran (Janssen) and 3,4-dihydro-2-methoxy-2H-pyran (Janssen) are distilled over calcium hydride and stored under dry nitrogen.
  • TBMA t-Butyl methacrylate
  • BPO Benzoyl peroxide
  • Hexamethyl- cyclotrisiloxane (D 3 , formula 6) (H ⁇ ls-Petrarch) is sublimed under vacuum and stored under nitrogen at -20°C.
  • the polymethylhydrosiloxanes PMHS 35 (Merck) and PMHS 8 o (Petrarch) are dried before use under vacuum at 40°C.
  • Karstedt catalyst (Petrarch) is used as obtained.
  • Azobis(isobutyronitril) (AIBN, Janssen) is recrystallized from methanol and stored at 10°C.
  • the active carbon is filtered off, after which the toluene solution is precipitated in 150 ml methanol.
  • the methanol is decanted and subsequently the white solid polymer is dried under high vacuum at room temperature.
  • the total yield is 0.95 g (53%) .
  • hydrosilylation reactions are also carried out with 4-t-butoxystyrene (TBS) and t-butyl methacrylate (TBMA) . Yield for combination of TBS with PMHS 35 40%; for PMHSao 50%. Yield for combination of TBMA with PMHS 35 30%; for PMHS 80 40%.
  • TBS 4-t-butoxystyrene
  • TBMA t-butyl methacrylate
  • the resist system has a positive or negative tone.
  • the t-butoxy-ether and t-butoxy-ester groups in the compounds of polysiloxanes with TBS and TBMA change into the corresponding alcohol and carboxylic acid respectively: h v +
  • the mechanisme is as indicated in Example 1. Accordingly, depending on the polarity of the developer, the resist system has a positive or negative tone.
  • the mechanism is as indicated in example l. Accordingly, depending on the polarity of the developer, the resist system has a positive or negative tone.
  • the initiator molecule Under the influence of the exposure, the initiator molecule generates an acid which subsequently causes the below condensation reaction to proceed catalytically.
  • the product is insoluble.
  • the resist system has a negative tone.
  • the mechanism is as indicated in example 4.
  • the resist system has a negative tone.
  • Tetrahydropyranyl protected polys ilsesquioxane
  • the initiator Under the influence of the exposure, the initiator generates an acid which subsequently causes a condensation reaction to proceed catalytically.
  • the product is insoluble.
  • the resist system has a negative tone.
  • the mechanism is as indicated in example .
  • the resist system has a negative tone.

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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Computer Hardware Design (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Materials For Photolithography (AREA)

Abstract

Procédé de production de microstructures pour conducteurs électriques, semi-conducteurs et isolants utilisant un système de résist multicouche. Dans la couche représentée, on utilise un polymère siliceux comportant des groupes latéraux à instabilité chimique et un excitant produisant, sous l'action d'un rayonnement, un catalyseur pouvant à son tour modifier chimiquement ces groupes latéraux. La teneur en silicium dudit polymère est telle que lors d'un traitement au plasma d'oxygène, un réseau fermé de silice se forme à la surface du polymère. On a également prévu un système de résist multicouche à comportement de positif et/ou de négatif pour la production de microstructures, et des polymères siliceux utilisables à cette fin.
PCT/NL1993/000240 1992-11-16 1993-11-16 Procede de production de microstructures WO1994011788A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU56599/94A AU5659994A (en) 1992-11-16 1993-11-16 Method of producing microstructures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NL9201996 1992-11-16
NL9201996A NL9201996A (nl) 1992-11-16 1992-11-16 Werkwijze voor het vervaardigen van microstructuren.

Publications (1)

Publication Number Publication Date
WO1994011788A1 true WO1994011788A1 (fr) 1994-05-26

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Application Number Title Priority Date Filing Date
PCT/NL1993/000240 WO1994011788A1 (fr) 1992-11-16 1993-11-16 Procede de production de microstructures

Country Status (3)

Country Link
AU (1) AU5659994A (fr)
NL (1) NL9201996A (fr)
WO (1) WO1994011788A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0758102A1 (fr) * 1995-08-08 1997-02-12 Olin Microelectronic Chemicals, Inc. Terpolymères présentant des chaînes latérales organosiliciées et leur utilisation dans la fabrication de structures en relief
DE102013003329A1 (de) 2013-02-25 2014-08-28 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Silane, Hybridpolymere und Photolack mit Positiv-Resist Verhalten sowie Verfahren zur Herstellung
US8920702B2 (en) 2008-12-19 2014-12-30 Andreas Hettich Gmbh & Co. Kg Device and method for producing a moulded body having microstructures

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4481049A (en) * 1984-03-02 1984-11-06 At&T Bell Laboratories Bilevel resist
JPS61294432A (ja) * 1985-06-24 1986-12-25 Nippon Telegr & Teleph Corp <Ntt> パタ−ン形成材料及びパタ−ン形成方法
EP0393348A2 (fr) * 1989-04-17 1990-10-24 International Business Machines Corporation Résine négative sensible au rayonnement et emploi
EP0466025A2 (fr) * 1990-07-06 1992-01-15 Nippon Telegraph And Telephone Corporation Matériau formant réserve, méthode pour produire ledit matériau et procédé pour former un motif sur ledit matériau formant réserve

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4481049A (en) * 1984-03-02 1984-11-06 At&T Bell Laboratories Bilevel resist
JPS61294432A (ja) * 1985-06-24 1986-12-25 Nippon Telegr & Teleph Corp <Ntt> パタ−ン形成材料及びパタ−ン形成方法
EP0393348A2 (fr) * 1989-04-17 1990-10-24 International Business Machines Corporation Résine négative sensible au rayonnement et emploi
EP0466025A2 (fr) * 1990-07-06 1992-01-15 Nippon Telegraph And Telephone Corporation Matériau formant réserve, méthode pour produire ledit matériau et procédé pour former un motif sur ledit matériau formant réserve

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 11, no. 162 (P - 579)<2609> 26 May 1987 (1987-05-26) *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0758102A1 (fr) * 1995-08-08 1997-02-12 Olin Microelectronic Chemicals, Inc. Terpolymères présentant des chaînes latérales organosiliciées et leur utilisation dans la fabrication de structures en relief
US5886119A (en) * 1995-08-08 1999-03-23 Olin Microelectronic Chemicals, Inc. Terpolymers containing organosilicon side chains
US6028154A (en) * 1995-08-08 2000-02-22 Olin Microelectronic Chemicals, Inc. Terpolymers containing organosilicon side chains
US6042989A (en) * 1995-08-08 2000-03-28 Olin Microelectronic Chemicals, Inc. Radiation sensitive compositions of terpolymers containing organosilicon side chains
US8920702B2 (en) 2008-12-19 2014-12-30 Andreas Hettich Gmbh & Co. Kg Device and method for producing a moulded body having microstructures
US9022775B2 (en) 2008-12-19 2015-05-05 Andreas Hettich Gmbh & Co. Kg Device and method for producing a moulded body having microstructures
DE102013003329A1 (de) 2013-02-25 2014-08-28 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Silane, Hybridpolymere und Photolack mit Positiv-Resist Verhalten sowie Verfahren zur Herstellung
US9625817B2 (en) 2013-02-25 2017-04-18 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Photoresist with positive-resist behaviour, method for photochemical structuring thereof, method for the production of silanes and of silicic acid (hetero)poly(co)condensates with positive-resist behaviour and also silicic acid (hetero)poly(co)condensates

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Publication number Publication date
AU5659994A (en) 1994-06-08
NL9201996A (nl) 1994-06-16

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