WO2007137581A1 - ProcÉdÉ de fixation d'un polymÈre Électriquement conducteur À un substrat polymÈre rigide, semi-rigide ou flexible, et produits obtenus par ce procÉdÉ - Google Patents

ProcÉdÉ de fixation d'un polymÈre Électriquement conducteur À un substrat polymÈre rigide, semi-rigide ou flexible, et produits obtenus par ce procÉdÉ Download PDF

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Publication number
WO2007137581A1
WO2007137581A1 PCT/DK2007/000251 DK2007000251W WO2007137581A1 WO 2007137581 A1 WO2007137581 A1 WO 2007137581A1 DK 2007000251 W DK2007000251 W DK 2007000251W WO 2007137581 A1 WO2007137581 A1 WO 2007137581A1
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WIPO (PCT)
Prior art keywords
polymer
conductive polymer
substrate
rigid
poly
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PCT/DK2007/000251
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English (en)
Inventor
Thomas Steen Hansen
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Danmarks Tekniske Universitet - Dtu
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Application filed by Danmarks Tekniske Universitet - Dtu filed Critical Danmarks Tekniske Universitet - Dtu
Publication of WO2007137581A1 publication Critical patent/WO2007137581A1/fr

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    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/24—Electrically-conducting paints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/16—Chemical modification with polymerisable compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes

Definitions

  • the present invention relates to a method for attaching an electrically conductive polymer to a rigid, semi-rigid or flexible polymer substrate.
  • the invention also relates to products obtained by the method and to the use of said products for the manufacture of inter alia microflow devices, circuits in active implants, sensors, e.g. disposable strips for measurement of blood sugar, medical devices and utensils, circuits in optical devices or circuits and components for electronic and photographic devices, e.g. OLED screens.
  • a conjugated polymer can be deposited on a substrate by direct in situ polymerisation on the surface of the substrate. This can be done by chemical oxidation, e.g. by coating the surface with a mixture of the monomer and the oxidant chosen. The resulting spontaneous reaction is suppressed in such a way that it will not occur until after the mixture has been spread on the substrate surface. Often such mixtures will have an insufficient stability, and more freedom in the design of the coating process can be achieved if the monomer and the oxidant are applied separately.
  • One way to achieve this is to apply the oxidant by solvent coating and subsequently expose the coated surface to monomer vapour, a process termed vapour phase polymerisation. Regardless of the chosen polymerisation route the adhesion or bonding of the polymer to the underlying substrate has always caused problems due to the large difference in surface energy between the polymers and almost any substrate chosen.
  • EP 0 825 219 A describes an electrically conductive polythiophene salt composition to be used as a clear and scratch-proof antistatic coating on articles of glass or plastics, e.g. television or computer screens.
  • the coatings are applied by methods known per se, e.g. spraying or spin coating.
  • DE 42 29 192 A1 concerns glass mouldings, especially television screens, provided with an antistatic polythiophene finish.
  • the polymer layer is preferably applied in a thickness of between 20 nm and 10 ⁇ m to obtain a sufficient protection against electrostatic charging with simultaneous high transparency.
  • a display screen of a cathode ray tube is provided with an electroconductive coating of poly-3,4-ethylenedioxythiophene.
  • the coating pro- vides an effective shield against electromagnetic radiation.
  • the coating can contain additional layers of e.g. silicon dioxide to improve the mechanical properties.
  • WO 2005/092521 A2 relates to a method for the preparation of a layer of a plasma-polymerised material on the surface of a substrate, e.g. a substrate of glass, an organosiloxane-based or polysiloxane-based material, silicon, Teflon® etc.
  • a substrate e.g. a substrate of glass, an organosiloxane-based or polysiloxane-based material, silicon, Teflon® etc.
  • Novel articles and microstructured or micropattemed devices having layers of electrically con- ductive materials, that give a conductivity of at least 0.01 S/cm, are also described.
  • a special feature is the plasma-polymerisation of 3,4-ethylenedioxythiophene (EDT), forming layers of poly(3,4-ethylenedioxythiophene) (PEDT).
  • EDT 3,4-ethylenedioxythiophene
  • PEDT poly(3,4-ethylenedioxythiophen
  • a commercial product is available from Agfa- Gevaert Group, Mortsel, Belgium (Tehrani, P. et al., Smart Mater. Struct. 2005; 14, N21 - N25), which can be applied to various substrates by spin coating.
  • the surface conductivity of films resulting from this product is significantly lower than that from films produced by in situ polymerisation.
  • the present invention overcomes the above mentioned drawbacks by providing a method for attaching an electrically conductive polymer to a rigid, semi-rigid or flexible polymer substrate, said method comprising the following steps:
  • a layer of the monomer to be polymerised to the desired conductive polymer is applied onto the surface of the polymer substrate or, alternatively, onto the surface of a carrier;
  • the applied monomer layer is polymerised in situ by means of chemical oxidation with an oxidising agent to form the conductive polymer on the surface;
  • the surface of the substrate comprising the conductive polymer and residual salt from the oxidation is washed with a solvent, which removes the salt and partly dissolves the surface, or, alternatively, the surface of the carrier comprising the conductive polymer and residual salt from the oxidation is provided with a film of the poly- mer substrate, which has previously been sprayed with or immersed in the solvent;
  • the composite polymer product is dried, if necessary by heating, whereby the solvent evaporates off and the conductive polymer is integrated into the top layer of the substrate structure, and
  • the polymer substrate with the attached conductive polymer is peeled off the carrier and immersed in a solvent for approximately 1 hour to remove the salt from the conductive polymer.
  • the method according to the invention permits facile attachment of a conductive poly- mer layer, especially poly(3,4-ethylenedioxythiophene) (PEDT), onto the surface of polymer substrates, preferably poly(methacrylate) (PMMA).
  • PEDT poly(3,4-ethylenedioxythiophene)
  • PMMA poly(methacrylate)
  • the present invention concerns a new method for intimate integration of conductive polymers onto polymer substrates.
  • a layer of the conductive polymer is made by polymerisation by chemical oxidation, e.g. using Fe(lll)-tosylate, followed by washing with a specifically selected solvent which simultaneously removes residual salt and dissolves the surface of the polymer substrate sufficiently for the conductive polymer to be integrated onto the polymer substrate.
  • PEDT poly(3,4-ethylenedioxythiophene)
  • PMMA poly(methacrylate)
  • the crucial step in the method according to the invention is not the in-situ polymerisation per se, which is well-documented in the prior art, but rather the washing step (i.e. step (c)) in the sequence of steps outlined above.
  • This step (c) has never been described before.
  • the in-situ polymerisation of films as described in the documents cited above in all cases yields layers of pure conductive polymer on a substrate, whereas the method according to the present invention yields a layer of conductive polymer blended with the top layer of the substrate, no matter if an intermediate carrier substrate is used or not.
  • the method according to the invention therefore results in a conductive polymer blend, which has advantageous mechanical properties while still being highly conduc- tive. In other words, it is surprising that the conductive polymer fully retains its conductivity after being incorporated in the substrate polymer.
  • the end product obtained according to the invention is significantly different from any prior art end product.
  • the advantage of the method according to the present invention is that a layer is obtained, which consists of a blend of the substrate polymer and the conductive polymer.
  • the layer adapts the mechanical properties of the substrate polymer, which in most cases would be much more preferable than the mechanical properties of the pure con- ductive polymer.
  • the blend remains exactly as conductive as the pure conductive polymer.
  • the polymer substrate can consist of a pure polymer or a mixture of polymers, optionally containing various fillers, such as glass fibres, carbon particles etc.
  • the polymer substrate is often non-conductive or has a poor conductivity, but otherwise has desirable physical and mechanical properties. By using the method according to the invention it has become possible to impart conductivity to such a polymer substrate while maintaining the physical and mechanical properties thereof.
  • the preparation of the conductive polymer PEDT is known, e.g. from a number of the patents cited above.
  • the polymer is prepared by heating a butanol solution of mono- meric 3,4-ethylenedioxythiophene (EDT) and Fe(III)(ToS) 3 , where Tos stands for p- toluenesulfonyl. After heating and polymerisation an even layer is obtained, which consists of the conductive polymer PEDT (approximately 10 %) and Fe(ll)(Tos) 2 /H-Tos (approximately 90 %). This layer is a very poor conductor and does not become electrically conductive until the salt has been washed out with water, ethanol or butanol.
  • the PEDT layer which has a porous structure, collapses to approximately 1/20 of its original thickness. It is known that if e.g. a polymer is admixed with the washing solvent, then it can be irreversibly trapped within the PEDT structure when the structure collapses.
  • the polymerisation of the electrically conductive polymer is carried out in situ on a selected polymer substrate, and the residual salt is washed out with a solvent which partially dissolves the substrate.
  • the polymer shrinks, and the upper layer of the substrate is "washed" into the electrically conductive polymer layer resulting in an interface between the conductive polymer layer and the polymer sub- strate, in which the conductive polymer layer is effectively integrated into the upper layer of the substrate due to mutual intertwinement of polymer chains from the conductive polymer and the polymer substrate in the interface.
  • the surface of the substrate has become electrically conductive, but otherwise the mechanical characteristics of the polymer substrate are retained.
  • the surface of the substrate has approximately the same conductivity as that which would have been obtained from the electrically conductive polymer, if said polymer had not been washed down in the substrate but merely had been washed with water. Thereby it is possible to obtain conductivities which are substantially higher than those obtainable by other methods.
  • the surface resistance of the conductive polymer layer remains low while the surface layer at the same time adapts some of the mechanical properties of the substrate yielding a high conductivity surface with very good wear resistance.
  • PEDT poly(3,4- ethylenedioxythiophene)
  • the applicant has integrated PEDT into poly(methylmethacrylate) (PMMA), polycarbonate (PC), cyclic olefin polymers (COC), poly(ethylene terephthalate) (PET), polyurethane (PUR) and polystyrene (PS) with the best results observed on PMMA, PUR, PC and COC. While the in- vestigation of the integration of conductive polymers into various polymer substrates mainly has been focused on the PEDT on PMMA system, the favourable results can be extended to other combinations of conductive polymers and non-conductive polymer substrates.
  • the polymer product consisting of a rigid, semi-rigid or flexible polymer substrate provided with an electrically conductive polymer integrated into the surface, which is made by the method according to the invention, has many favourable utilities.
  • the product is used for the manufacture of microflow devices, circuits in active implants, sensors, e.g. disposable strips for measurement of blood sugar, medical devices and utensils, circuits in optical devices or circuits and components for electronic and photographic devices, e.g. OLED screens.
  • the EDT monomer (Baytron M) and Fe(lll)-tosylate (40 % in butanol) were purchased from Bayer AG, Leverkusen, Germany.
  • the PMMA substrates were purchased from Nordisk Plast A/S, Auning, Denmark.
  • Other polymer substrates employed resulted from injection molding polycarbonate (DPI-1265, BASF, Ludwigshafen, Germany) or polystyrene (Bayer AG, Leverkusen, Germany), hot pressing of COC (Topas 8007, Ticona, Frankfurt, Germany) or curing of poly(dimethylsiloxane) (Sylgard 184, Dow Chemicals, Midland, Michigan, USA). All other chemicals were purchased from Sigma-Aldrich, Taufmün, Germany. Ultra-pure water with a resistivity of >18.2 M ⁇ was used. Examples
  • the polymerisation was carried out starting from a solution containing 6.5 ml Baytron C, 2.0 ml water, 0.22 ml EDT and 0.15 ml pyridine.
  • the purpose of adding water is to decrease the viscosity and prolong the pot life of the solution.
  • the solution was applied onto 50 x 50 x 1.5 mm PMMA sheets by spin coating using a Delta 10TT (S ⁇ ss Mictrotec, Kunststoff, Germany) spin coater. Spin velocities/times of 250 to 4000 rpm for 30 seconds were employed.
  • the coated substrates were baked at 65 0 C for 10 minutes on a hot plate to evaporate any remaining solvent and initiate the polymerisation.
  • the substrates were subsequently washed by applying 3 ml of a 1 :1 (v/v) mixture of butanol and anisole to the polymer coated substrate surface while spinning at 1000 rpm for 20 seconds.
  • the washed substrates were further dried for 5 minutes at 65 0 C on a hot plate.
  • a mixture of 6.5 ml Baytron C, 0.22 ml EDT, 0.15 ml pyridine and 2 ml butanol is prepared and applied onto a silicon wafer by spin coating.
  • the substrate may be glass or silicon as long as the material is able to withstand organic solvents.
  • the silicon wafer is heated to 60 0 C to evaporate the solvent and initiate the polymerisation. After the polymerisation the PEDT-coated wafer is cooled to room temperature.
  • a polyurethane film is immersed in or sprayed with a solution of butanol/THF and subsequently placed on top of the PEDT-coated side of the wafer.
  • the wa- fer/PEDT/polyurethane composite is slowly heated to a temperature below the boiling point of the solvent to make the solvent diffuse out through the polyurethane layer.
  • the PEDT/polyurethane layer is peeled off the wafer.
  • the PEDT is integrated into the polyure- thane, but the salts formed during the polymerisation have not yet been removed. Therefore the PEDT/polyurethane sample must be immersed in e.g. ethanol for approximately one hour after the integration.
  • Example 2 Employing the procedure of Example 1 other combinations of conductive polymers and non-conductive polymer substrates were produced using other washing solvents or solvent mixtures. The tested combinations are summarised in the table below.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)

Abstract

L'invention concerne un nouveau procédé de fixation d'un polymère électriquement conducteur à un substrat polymère rigide, semi-rigide ou flexible. Une couche du polymère conducteur est polymérisée par oxydation chimique, par ex. en utilisant du ferritosylate, puis lavée avec un solvant qui élimine le sel résiduel et dissout simultanément la surface du substrat polymère, ce qui entraîne l'intégration du polymère conducteur dans le réseau polymère du substrat. Plusieurs combinaisons de polymères conducteurs et de substrats peuvent être utilisées, la combinaison la plus préférée étant du poly(3,4-éthylènedioxythiophène) (PEDT) sur des substrats de poly(méthacrylate)(PNNA). Les propriétés mécaniques et chimiques de la surface du polymère conducteur/substrat ressemblent étroitement à celles de la surface du substrat. La résistance de surface de la couche de polymère conducteur reste basse tandis que la couche de surface adapte dans le même temps certaines des propriétés mécaniques du substrat, pour aboutir à une surface de conductivité élevée avec une très bonne résistance à l'usure. Le procédé peut être employé pour la fabrication de dispositifs à micro-écoulement, de circuits pour des implants actifs, de capteurs, par ex. de bandes jetables pour la mesure de la glycémie, de dispositifs et d'ustensiles médicaux, de circuits pour des dispositifs optiques ou des circuits et de composants pour des dispositifs électroniques et photographiques, par ex. des écrans OLED.
PCT/DK2007/000251 2006-05-31 2007-05-30 ProcÉdÉ de fixation d'un polymÈre Électriquement conducteur À un substrat polymÈre rigide, semi-rigide ou flexible, et produits obtenus par ce procÉdÉ WO2007137581A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US80949306P 2006-05-31 2006-05-31
EP06388039 2006-05-31
EPEP06388039.7 2006-05-31
USUS60/809,493 2006-05-31

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WO2007137581A1 true WO2007137581A1 (fr) 2007-12-06

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111902498A (zh) * 2018-04-10 2020-11-06 拓自达电线株式会社 导电性涂料及使用该导电性涂料的屏蔽封装体的制造方法
CN111892306A (zh) * 2020-07-23 2020-11-06 安徽晶驰光电科技有限公司 一种防眩光涂膜ag玻璃的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339340A2 (fr) * 1988-04-22 1989-11-02 Bayer Ag Polythiophènes, procédé pour leur préparation et leur utilisation
WO2005092521A2 (fr) * 2004-03-26 2005-10-06 Forskningscenter Risø Polymerisation au plasma de composes polycycliques

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0339340A2 (fr) * 1988-04-22 1989-11-02 Bayer Ag Polythiophènes, procédé pour leur préparation et leur utilisation
WO2005092521A2 (fr) * 2004-03-26 2005-10-06 Forskningscenter Risø Polymerisation au plasma de composes polycycliques

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
"BAYTRON Coating Guide, Issue 10/2002", INTERNET CITATION, October 2002 (2002-10-01), XP002322056, Retrieved from the Internet <URL:http://www.hcstarck.de/pages/334/baytron_coatingguide_01035997.pdf> [retrieved on 20061108] *
ANONYMOUS: "High conductive Baytron coatings by in-situ Polymerisation", INTERNET ARTICLE, 5 August 2003 (2003-08-05), pages 1 - 6, XP002406106, Retrieved from the Internet <URL:http://www.baytron.com/pages/983/insitumanual.pdf> [retrieved on 20061108] *
AVLYANOV ET AL: "In-situ deposited thin films of polypyrrole: conformational changes induced by variation of dopant and substrate surface", SYNTHETIC METALS, ELSEVIER SEQUOIA, LAUSANNE, CH, vol. 84, no. 1-3, January 1997 (1997-01-01), pages 153 - 154, XP005261092, ISSN: 0379-6779 *
PETTERSSON L A A ET AL: "Spectroscopic ellipsometry studies of the optical properties of doped poly(3,4-ethylenedioxythiophene): an anisotropic metal", THIN SOLID FILMS, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 313-314, 13 February 1998 (1998-02-13), pages 356 - 361, XP004133012, ISSN: 0040-6090 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111902498A (zh) * 2018-04-10 2020-11-06 拓自达电线株式会社 导电性涂料及使用该导电性涂料的屏蔽封装体的制造方法
CN111902498B (zh) * 2018-04-10 2022-07-19 拓自达电线株式会社 导电性涂料及使用该导电性涂料的屏蔽封装体的制造方法
US11912897B2 (en) 2018-04-10 2024-02-27 Tatsuta Electric Wire & Cable Co., Ltd. Electroconductive coating material and method for producing shielded package using said electroconductive coating material
CN111892306A (zh) * 2020-07-23 2020-11-06 安徽晶驰光电科技有限公司 一种防眩光涂膜ag玻璃的制备方法
CN111892306B (zh) * 2020-07-23 2022-09-06 安徽晶驰光电科技有限公司 一种防眩光涂膜ag玻璃的制备方法

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