WO2008046398A2 - Procédé de production de monocouches autoassembleuses sur des surfaces de corps solides - Google Patents

Procédé de production de monocouches autoassembleuses sur des surfaces de corps solides Download PDF

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Publication number
WO2008046398A2
WO2008046398A2 PCT/DE2007/001833 DE2007001833W WO2008046398A2 WO 2008046398 A2 WO2008046398 A2 WO 2008046398A2 DE 2007001833 W DE2007001833 W DE 2007001833W WO 2008046398 A2 WO2008046398 A2 WO 2008046398A2
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WO
WIPO (PCT)
Prior art keywords
sams
solid surfaces
solid
aggregated
monolayers
Prior art date
Application number
PCT/DE2007/001833
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German (de)
English (en)
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WO2008046398A3 (fr
Inventor
Bernd Holzapfel
Original Assignee
Philipps-Universität Marburg
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Publication date
Application filed by Philipps-Universität Marburg filed Critical Philipps-Universität Marburg
Publication of WO2008046398A2 publication Critical patent/WO2008046398A2/fr
Publication of WO2008046398A3 publication Critical patent/WO2008046398A3/fr

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0218—Pretreatment, e.g. heating the substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/60—Deposition of organic layers from vapour phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/18—Processes for applying liquids or other fluent materials performed by dipping
    • B05D1/185—Processes for applying liquids or other fluent materials performed by dipping applying monomolecular layers

Definitions

  • the present invention describes a process for the preparation of self-aggregating monolayers (SAMs) in a high vacuum in the gas phase with oxygen exclusion in the protective gas stream.
  • SAMs self-aggregating monolayers
  • the surface to be vaporized is cleaned and heated in a high vacuum to a temperature ⁇ 100 O.
  • the substance to be aggregated is heated until it evaporates and this vapor is vaporized onto the surface via an introduction system together with an oxygen-free inert gas.
  • Monolayers form within 30 to 60 minutes.
  • the present invention relates to the fields of physical solid state chemistry, surface chemistry and materials science.
  • Self-assembling monolayers also known as self-assembling monolayers or SAMs for short, are used in electronic switches, microelectronic and nanoelectronic components, optical and electro-optical devices, gates, storage media and sensors, since they offer a variety of surface modification possibilities.
  • SAMs self-assembling monolayers
  • the interest in these monolayers is due to applications in terms of settable wettability, biocompatibility and corrosion resistance of surfaces.
  • SAMs are highly ordered molecular assemblies that form spontaneously by chemisorption of functionalized molecules on a variety of solid-state surface substrates.
  • the molecules that make up the self-aggregating monolayer organize laterally; This is usually done by van der Waals interactions between long aliphatic chains.
  • SAMs for example, is of interest for many electronic, optical and electro-optical devices, as SAMs allow the targeted modification of surface areas, such as the modification of surface hydrophobicity, packing of the layers and electrical insulation. Since SAMs have excellent barrier properties, their use as a protective layer on metallic surfaces is considered because they are thin, highly crystalline Form barrier films.
  • Gold is widely used as a surface material and is used extensively in the electronics industry, for example, for the manufacture of integrated circuits. As a relatively inert metal, it is also used as a protective layer in certain chemical environments; for example, as liner material for the ink chambers in printheads of ink jet printers. However, gold dissolves under suitable chemical or electrochemical conditions, therefore the ability of SAMs to form a very thin protective layer for such metallic surfaces under such chemical conditions is considered a very attractive utility of self-aggregating monolayers.
  • SAMs also have some disadvantages that still limit their commercial applicability in industrial processes.
  • the deposition of the SAMs from suitable solvents As a rule, the surface of a solid to be coated contains discontinuities which result from the production process determined by the desired application, so that the deposition of a monolayer in the form of a flat layer on the solid surface is difficult to control.
  • impurities of the solvent lead to impurities in the self-aggregating monolayer and the deposition proceeds very slowly. Typical deposition times range from a few hours to several days.
  • US 2006/008678 A1 describes the preparation of SAMs comprising dendrimers, the dendrimers being precipitated from a solution. or the substrate to be coated is exposed to a dendrimer in compressed or supercritical CO2.
  • compressed CO2 as a solvent medium for a substance to be deposited as SAM is also disclosed in US 2002/0197879 A1 and US 2002/0164419 A1.
  • No. 5,514,501 A1 describes a process for the photostructuring of thiolate SAMs in which two SAM layers of thiolates are deposited successively on a noble metal substrate, the thiolates being in solution before deposition.
  • 6,821,485 B2 discloses a device for guiding a microfluidic flow within canals and a method for the production thereof, wherein the channels are coated with a SAM and the SAM is precipitated from solution.
  • US Pat. No. 6,485,984 B2 discloses a method for producing biochips which contain calixarene SAMs on a gold carrier, wherein the SAMs are precipitated from solution.
  • US 2006/0062921 A1 describes a method for producing a gradient on a surface by means of vapor diffusion, in which a surface is held under a set of one or more conditions, wherein the set of conditions is selected from pressure, pH, temperature and combinations thereof. Subsequently, a stamp comprising a fugitive stencil material is positioned adjacent to that surface and then varying the one or more conditions to thereby deposit variable concentrations of the stencil material at various points on the surface.
  • DE 10 2004 009 600 A1. Describes the deposition of a substrate on a gate electrode, wherein the material for the gate electrode is present in solution. Then the gate electrode becomes .
  • US 2004/0223256 A1 discloses a coating method for applying corrosion protection to magnetic read-write heads, in which the monolayer surface passes through. a vacuum coating process can be applied; however, this process does not include a permanent inert gas flow.
  • US 2004/0025733 A1 describes a method for surface modification of optical elements by applying a SAM in order to adjust the hydrophilicity or hydrophobicity of the element, wherein the modifying agent from which the SAM is formed is released into a vacuum chamber and the surface to be coated also located in this vacuum chamber. However, no inert gas is used in this process. In the known processes which deposit SAMs from the gas phase, the deposition does not take place in a permanent stream of inert gas; therefore, impurities of the SAMs to be formed by oxygen can not be excluded.
  • the present invention is based on the deposition of a SAM on a solid surface in the permanent, oxygen-free gas stream at pressures between 10 "6 and 10 " 8 mbar and provides within a few minutes SAMs 1 which are substantially free of contaminants.
  • the adhesion of the SAMs on the solid surfaces is achieved by adhesion.
  • the process according to the invention therefore offers the following advantages over known processes: time savings in the production, saving of chemicals (solvents) and devices (stamps) as well as higher purity of the products.
  • the object of the present invention is to provide a process for the production of self-aggregating monolayers (SAMs) on solid surfaces, in which contamination of the surfaces by solvents and / or oxygen is minimized.
  • SAMs self-aggregating monolayers
  • This object is achieved by the substance to be aggregated or the substances to be aggregated is heated to evaporation and this steam in a permanent, oxygen-free gas stream at a temperature of ⁇ 100 O and a pressure of 10 '6 to 10 ' 8 mbar within from 30 to 60 minutes on the coated solid surface is evaporated.
  • the adhesion of the self-aggregating monolayers to the solid surface occurs by adhesion.
  • the deposition of the SAM molecules takes place in the permanent gas stream.
  • metals and metal oxides are selected from titanium, titanium dioxide, tin, tin oxide, silicon, silica, iron, iron 111 oxide, silver, gold, copper, platinum, palladium, nickel, aluminum, steel, indium. indium tin oxide, fluoride doped tin oxide, ruthenium oxide, germanium cadmium selenide, cadmium selenide, cadmium sulfide, titanium alloys.
  • the surface may be a single substrate, for example, a semiconductor material such as silicon, silicon germanium, silicon carbide, a disk substrate for magnetic recording media, or a composite substrate in which one or more films of one or more further materials were deposited on the single substrate.
  • the film materials may be, for example, a metal such as gold or silver or an insulator such as silicon oxide, silicon nitride, silicon oxynitride, a dielectric material, a polysilicon or a metal silicide, a glass or an indium tin oxide.
  • the surfaces on which a self-aggregating monolayer is to be applied are preferably cleaned beforehand.
  • cleaning methods include rinsing the surface with an organic solvent such as ethanol, acetone, isopropanol, further purification by oxidation with Caro's acid H 2 SO 5 or by UV light and cleaning in an ultrasonic bath followed by drying.
  • the oxygen-free gas for generating the permanent gas stream is selected from the group helium, neon, argon, krypton, xenon, nitrogen, carbon monoxide, carbon dioxide.
  • High purity gas is used, i. the degree of purity is at least 3.5 according to dot notation.
  • the substance to be aggregated on the solid surface is selected from Biphenyls, for example nitrobiphenylthiol, hydroxybiphenyl,
  • Alkylchlorosilanes for example monochlorosilanes, perfluorooctadecyltrichlorosilanes, tridecafluoro-x-tetrahydrooctyltrichlorosilanes or, generally, alkylhalosilanes, non-chlorine-containing dimethylaminosilanes
  • a precursor material can also be used.
  • a precursor here is to be understood as meaning a precursor substance whose molecules contain the material-constituting chemical constituents of the layer, i.
  • Precursor materials which can be used according to the invention consist of molecules having a functional group which reacts with a surface of silicon if silicon is chosen as the solid surface to be coated. These include, for example, all organic chlorosilanes, including perfluoroalkylchlorosilanes and dimethyldichlorosilanes.
  • a mixture to aggregating substances or their precursors can be evaporated, if the vapor pressures of substances to be aggregated or precursors differ by a maximum of 2 4 IO "4 mbar.
  • Self-aggregating monolayers which are produced on solid surfaces by means of the method according to the invention can be used, for example, in the production of electronic, optical and electro-optical components, for example in sensor technology or in microswitches for airbag deployment.
  • the person skilled in the art knows how to use mask-lithographic methods for nano-structuring of semiconductors on solid surfaces with SAMs.
  • the SAMs produced by the method according to the invention can be chemically changed by means of electron beams. SAMs are also suitable as corrosion protection and as adhesion promoters in composite materials.
  • the inventive method is also suitable for the production of medical stents, wherein the metallic solid state materials of the stents for the purpose of better tissue compatibility with SAMs are coated from a physiologically acceptable material.
  • Semipermeable membranes and substrates for biological cell cultures can also be produced by SAMs according to the method of the invention.
  • Caro's acid is freshly made from 30% hydrogen peroxide and concentrated sulfuric acid (1: 3 v / v).
  • Silicon wafers (3 cm * 1 cm * 0.5 mm) are placed in the freshly prepared Caro's acid for 30 minutes, then rinsed with water with a maximum conductivity of 0.05 ⁇ S and then with methanol pa and dried in a stream of nitrogen. Thereafter, the wafers are placed in 48% hydrofluoric acid for 5 minutes to 10 minutes, rinsed with anhydrous toluene and first pre-dried in a stream of nitrogen. Thereafter, the wafer (FIG. 1) are in an argon-purged vaporization converted in vacuo at 9 * 10 "7 mbar within 30 min dried.
  • valve A (2) After completion of vapor deposition, the argon supply is terminated by valve A (2) is closed
  • the heater (thermostat, 6) is switched off, after another 5 min, the argon supply is stopped by closing valve A (2), the vaporised wafers are allowed to cool for 1 h within the evaporator, then valve B (5) is closed and the Evaporating system ventilated by opening valve A (2) with argon.
  • the coated with a Hydroxybiphenyl monolayer silicon wafers are then rinsed with ethyl acetate pa, cleaned for 5 ⁇ 2 min in an ultrasonic bath, dried in a nitrogen stream and stored under argon atmosphere.
  • Argon used has a purity of 4.8 after dot notation; the purity of the nitrogen used is 4.6 after dot notation.
  • the vaporization system is shown schematically in FIG.
  • the XPS diagram (X-ray photoelectron spectroscopy) of the hydroxybiphenyl-SAM (HBP-SAM) formed is shown in FIG. 2.
  • An aluminum anode served as a source for the X-radiation;
  • the energy of K ⁇ -ünie is 1486.6 eV with a half-width of about 1 eV.
  • Gold wafers (3 cm * 1 cm * 0.5 mm) are subjected to ozonolysis with UV light for two hours and then rinsed with DMF pa. Then they are cleaned for 5 minutes in an ultrasonic bath, rinsed with DMF pa and then with ethanol pa and finally dried in a stream of nitrogen, purity 4.6 according to dot notation.
  • the wafers are removed and rinsed with DMF.
  • the wafers are then treated in a DMF-filled beaker for 5 minutes in an ultrasonic bath.
  • the wafers will now multiply with DMF pa and then Rinsed several times with ethanol pa, preferably 5 rinses are carried out with DMF or ethanol.
  • the wafers are treated in an ethanol pa filled beaker for 5 minutes in an ultrasonic bath, rinsed with ethanol pa, dried in a stream of nitrogen and stored until further use under a nitrogen atmosphere.
  • Figure 3 shows the XPS plot of the NBPT SAMs so obtained on gold wafer (NBPT / Au s ).
  • Anode material and energy of K ⁇ radiation were as described in Example 1.
  • An AFM (Force Field Microscopy) image was taken using silicon nitride vane valve (tip radius 10 nm, spring constant 0.2 N / m).
  • the scan area of the AFM / LFM head was 80 ⁇ m * 80 ⁇ m in the x, y plane. It was scanned in contact mode with a force of 12 nN.
  • the height difference (in the z-direction) of the deposited NBPT molecules was at most 10 nm.
  • the gold wafers are prepared as described in Example 2.
  • the wafer be in a purged with argon vaporization exceeded resulting in vacuo at 9 * 10 -7 mbar within 30 min.
  • piston (1) is summed twice at 80 O nitrobiphenylthiol at 80 ⁇ C and a pressure of 10 "5 mbar under an argon atmosphere (3) is evaporated. Subsequently, the valve is opened A (2) and the gold wafers at 10 '5 mbar and 80 0 C steamed with NBPT within 30 min to 60 min. After completion of the evaporation, the argon supply is stopped by valve A (2) is closed. The heating (thermostat, 6) is switched off. After a further 5 minutes, the argon supply is terminated by closing valve A (2). The vapor-deposited wafers cool for 1 h within the vaporization unit. Then valve B (5) is closed and the steaming system is vented by opening valve A (2) with argon.
  • FIG. 1 shows the XPS plot of the NBPT SAMs so obtained on gold wafers (NBPT / Au G ).
  • Anode material and energy of K ⁇ radiation were as described in Example 1.
  • An AFM (Force Field Microscopy) image was taken using silicon nitride vane valve (tip radius 10 nm, spring constant 0.2 N / m).
  • the scan area of the AFM / LFM head was 80 ⁇ m * 80 ⁇ m in the x, y plane. It was scanned in contact mode with a force of 12 nN. The height difference (in the z-direction) of the deposited NBPT molecules was at most 10 nm. LIST OF REFERENCE NUMBERS
  • Fig. 1 shows schematically a vapor deposition system.
  • the substance to be aggregated is evaporated; the heating takes place via the thermostat (6).
  • the vaporized substance can be directed into the vessel with the wafers (4) to be vaporized.
  • the vessel with the wafers to be vaporized (4) further oxygen-free gas (3) is introduced.
  • X-ray photoemission diagram (XPS diagram) of hydroxybiphenyl SAMs on silicon wafers, cf. Embodiment 1.
  • An aluminum anode served as a source of X-radiation.
  • the energy of the K ⁇ line is 1486.6 eV with a half width of about 1 eV.
  • XPS diagram X-ray photoemission diagram
  • NBPT-SAMs on Goldwafem.
  • An aluminum anode served as a source of X-radiation.
  • the energy of the K ⁇ line is 1486.6 eV with a half width of about 1 eV.
  • the upper curve shows an NBPT-SAM, which was deposited from the gas phase by means of the method according to the invention (NBPT / AU G ), cf.
  • Exemplary embodiment 3 The lower curve shows an NBPT-SAM which has been deposited from solution (NBPT / Aus), cf.

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  • Physical Vapour Deposition (AREA)
  • Chemical Vapour Deposition (AREA)

Abstract

L'invention concerne un procédé de production de monocouches autoassembleuses (SAM) sur des surfaces de corps solides, procédé selon lequel des impuretés des surfaces sont minimisées par l'usage de solvants et/ou d'oxygène. A cet effet, les substances à assembler sont évaporées et déposées par évaporation dans un flux gazeux exempt d'oxygène, sur la surface à revêtir des corps solides, sous des pressions comprises entre 10-6 et 10-8 mbar. Les procédés conventionnels, dans lesquels les SAM sont déposés à partir d'une solution, nécessitent des temps de dépôt allant de quelques heures à plusieurs jours. Le procédé selon l'invention permet par contre un dépôt de monocouches en 30 à 60 minutes.
PCT/DE2007/001833 2006-10-16 2007-10-16 Procédé de production de monocouches autoassembleuses sur des surfaces de corps solides WO2008046398A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006049432.6 2006-10-16
DE200610049432 DE102006049432A1 (de) 2006-10-16 2006-10-16 Verfahren zur Herstellung von selbst aggregierenden Monolagen auf Festkörperoberflächen

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WO2008046398A2 true WO2008046398A2 (fr) 2008-04-24
WO2008046398A3 WO2008046398A3 (fr) 2008-09-25

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN102552977A (zh) * 2012-01-19 2012-07-11 上海交通大学医学院附属第九人民医院 金属表面刻蚀纳米孔阵列的制备方法及其用途

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102017216028A1 (de) * 2017-09-12 2019-03-14 Robert Bosch Gmbh Elektrochemische Zelle mit beschichteten Oberflächen

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EP0547550A1 (fr) * 1991-12-16 1993-06-23 Matsushita Electric Industrial Co., Ltd. Procédé pour fabriquer un film adsorbé chimiquement
US6365229B1 (en) * 1998-09-30 2002-04-02 Texas Instruments Incorporated Surface treatment material deposition and recapture
US20040071863A1 (en) * 2002-10-11 2004-04-15 Xiaoyang Zhu Methods for forming coatings on MEMS devices
WO2004037446A1 (fr) * 2002-10-18 2004-05-06 Ecole Polytechnique Federale De Lausanne Depot en phase gazeuse d'alkylsilanes perfluores
US20040198898A1 (en) * 2001-08-03 2004-10-07 Arora Pramod K. Method for vapor deposition of hydrophobic films on surfaces

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US6576489B2 (en) * 2001-05-07 2003-06-10 Applied Materials, Inc. Methods of forming microstructure devices
US20020182385A1 (en) * 2001-05-29 2002-12-05 Rensselaer Polytechnic Institute Atomic layer passivation
TWI249651B (en) * 2002-06-14 2006-02-21 Asml Netherlands Bv EUV lithographic projection apparatus comprising an optical element with a self-assembled monolayer, optical element with a self-assembled monolayer, method of applying a self-assembled monolayer, device manufacturing method and device manufactured there
US7327535B2 (en) * 2003-05-08 2008-02-05 Sae Magnetics (H.K.) Ltd. Hybrid coating for magnetic heads
DE102004009600B4 (de) * 2004-02-27 2008-04-03 Qimonda Ag Selbstorganisierende organische Dielektrikumsschichten auf der Basis von Phosphonsäure-Derivaten

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0547550A1 (fr) * 1991-12-16 1993-06-23 Matsushita Electric Industrial Co., Ltd. Procédé pour fabriquer un film adsorbé chimiquement
US6365229B1 (en) * 1998-09-30 2002-04-02 Texas Instruments Incorporated Surface treatment material deposition and recapture
US20040198898A1 (en) * 2001-08-03 2004-10-07 Arora Pramod K. Method for vapor deposition of hydrophobic films on surfaces
US20040071863A1 (en) * 2002-10-11 2004-04-15 Xiaoyang Zhu Methods for forming coatings on MEMS devices
WO2004037446A1 (fr) * 2002-10-18 2004-05-06 Ecole Polytechnique Federale De Lausanne Depot en phase gazeuse d'alkylsilanes perfluores

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102552977A (zh) * 2012-01-19 2012-07-11 上海交通大学医学院附属第九人民医院 金属表面刻蚀纳米孔阵列的制备方法及其用途

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WO2008046398A3 (fr) 2008-09-25

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