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DE3344753A1 - Preparation of electroconductive polymers, and their use in electrical engineering and as antistatics - Google Patents

Preparation of electroconductive polymers, and their use in electrical engineering and as antistatics

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Publication number
DE3344753A1
DE3344753A1 DE19833344753 DE3344753A DE3344753A1 DE 3344753 A1 DE3344753 A1 DE 3344753A1 DE 19833344753 DE19833344753 DE 19833344753 DE 3344753 A DE3344753 A DE 3344753A DE 3344753 A1 DE3344753 A1 DE 3344753A1
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Prior art keywords
polymers
alkali metal
electrical
lewis acid
electrically conductive
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DE19833344753
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German (de)
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Gernot Dr. 6700 Ludwigshafen Köhler
Herbert Dr. 6719 Wattenheim Naarmann
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BASF SE
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BASF SE
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Priority to DE19833344753 priority Critical patent/DE3344753A1/en
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    • 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
    • H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to a process for the preparation of electroconductive polymers having electroconductivity values of greater than 10<-2> S/cm, in which polymers of propargyl halides are dehydrogenated using a dehydrogenating agent to give polymers, which are subsequently reacted with a Lewis acid, alkali metal or alkali metal derivative. The electroconductive polymers obtained can be used in electrical engineering for the production of solar cells, for the conversion and fixation of radiation, for production of electrical and magnetic switches and electrical stores and for the antistatic finishing of plastics.

Description

Herstellung von elektrisch leitfähigen Polymeren und deren Verwendung inManufacture of electrically conductive polymers and their use in

der Elektrotechnik und als Antistatika Die Erfindung betrifft ein Verfahren zur Herstellung von elektrisch leitfähigen Polymeren mit elektrischen Leitfähigkeiten größer als 10 2 S/cm aus Polymerisaten von Propargylhalogeniden und deren Verwendung in der Elektrotechnik und als Antistatika.of electrical engineering and as antistatic agents The invention relates to a Process for the production of electrically conductive polymers with electrical Conductivities greater than 10 2 S / cm from polymers of propargylic halides and their use in electrical engineering and as antistatic agents.

Der Erfindung lag die Aufgabe zugrunde, nach neuer einfacher, chemischer Verfahrensweise elektrisch leitfähige Polymere mit Leitfähigkeiten größer als 10 2 S/cm zu schaffen, wobei von fertigen Vorpolymerisaten ausgegangen werden soll.The invention was based on the object of new, simpler, more chemical Procedure electrically conductive polymers with conductivities greater than 10 2 S / cm, assuming finished prepolymers.

Die Aufgabe wurde dadurch gelöst, daß Polymerisate von Propargylhalogeniden dehydriert und anschließend mit einer Lewis-Säure oder einem Alkalimetall oder Alkalimetallderivat in Mengen von 1 bis 70, vorzugsweise 5 bis 45 Gew.%, bezogen auf das dehydrierte Polymere, umsetzt.The object was achieved in that polymers of propargyl halides dehydrated and then with a Lewis acid or an alkali metal or alkali metal derivative In amounts of 1 to 70, preferably 5 to 45% by weight, based on the dehydrated Polymers.

Unter elektrisch leitfähigen Polymeren mit elektrischen Leitfähigkeiten größer als 10 2 S/cm werden Substanzen verstanden, die nach der Meßmethode von F. Beck, Berichte der Bunsengesellschaft 68, (1964), Seite 559 eine elektrische Leitfähigkeit von über 10 2 S/cm aufweisen.Among electrically conductive polymers with electrical conductivities substances greater than 10 2 S / cm are understood to be substances which, according to the measuring method of F. Beck, reports of the Bunsengesellschaft 68, (1964), page 559 an electrical conductivity of over 10 2 S / cm.

Die Polymerisate von Propargylhalogeniden, welche erfindungsgemäß zur Anwendung kommen, werden hergestellt durch Polymerisation von Propargylchlorid bzw. Propargylbromid mit Hilfe von PdCl2 in Dimethylformamid, analog der Lit. Vysokomol. soyed. A 17, Nr. 11, 2514-2520 (1975), jedoch mit deutlich höheren Katalysatorkonzentrationen. Es werden insbesondere 1 bis 25 Gew.% als Katalysator verwendet. Als Katalysatoren eignen sich z.B. Nickelchelate wie beispielsweise Nickel11acetylacetonat oder Kobaltchelate wie beispielsweise Kobalt 111benzoylacetonat. Man polymerisiert die Propargylhalogenide bei Temperaturen von +60 bis 1600C. Als Lösungsmittel verwendet man Dimethylformamid, Dimethylsulfoxid oder N-Methyl--pyrrolidon.The polymers of propargyl halides which according to the invention are used, are produced by the polymerization of propargyl chloride or propargyl bromide with the help of PdCl2 in dimethylformamide, analogous to Ref. Vysokomol. soyed. A 17, No. 11, 2514-2520 (1975), but with significantly higher catalyst concentrations. In particular, 1 to 25% by weight are used as the catalyst. As catalysts Nickel chelates such as nickel 11 acetylacetonate or cobalt chelates are suitable, for example such as cobalt 111 benzoylacetonate. The propargyl halides are polymerized at temperatures from +60 to 1600C. The solvent used is dimethylformamide, Dimethyl sulfoxide or N-methyl pyrrolidone.

Es entstehen Polymerisate der allgemeinen Formel I worin n gleich 5 bis 500 und X gleich C;oder ;Br sein kann. Nach dem erfindungsgemäßen Verfahren werden die Polymerisate der Propargylhalogenide mit einem der Dehydrierungsmittel umgesetzt, wobei ein dehydriertes Polymeres der allgemeinen Formel II entsteht, worin n und X die oben angegebene Bedeutung haben. Hierzu kann man die Polymerisate der Propargylhalogenide, die analog der oben genannten Literatur hergestellt wurden, in Gegenwart von 1 bis 30 Gew.% der Dehydriermittel 0,1 bis 5 Stunden auf 50 bis 2500C erhitzen und das erhaltene dehydrierte Polymere mit Wasser und Hilfsflüssigkeiten waschen. Als Dehydrierungsmittel werden bevorzugt Schwefel, Selendioxid, Mangandioxid oder Mangan-III-acetat verwendet.Polymers of the general formula I are formed where n can be 5 to 500 and X can be C; or; Br. In the process according to the invention, the polymers of the propargyl halides are reacted with one of the dehydrogenating agents, a dehydrogenated polymer of the general formula II arises, in which n and X have the meaning given above. For this purpose, the polymers of the propargyl halides, which were prepared analogously to the literature mentioned above, can be heated to 50-2500C for 0.1 to 5 hours in the presence of 1 to 30% by weight of the dehydrating agents and the dehydrogenated polymer obtained can be washed with water and auxiliary liquids. Sulfur, selenium dioxide, manganese dioxide or manganese III acetate are preferably used as dehydrating agents.

Das so gewonnene Polymere wird dann mit 1 bis 70, bevorzugt 5 bis 45 Gew.%, bezogen auf das dehydrierte Polymere, einer Lewis-Säure oder einem Alkalimetall oder Alkalimetallderivat umgesetzt. Bevorzugt wird erfindungsgemäß als Lewis-Säure ein Halogenderivat von Elementen der III., IV., V., VI., VII. oder VIII. Gruppe des Periodensystems der Elemente verwendet.The polymer obtained in this way is then with 1 to 70, preferably 5 to 45% by weight, based on the dehydrogenated polymer, of a Lewis acid or an alkali metal or alkali metal derivative implemented. According to the invention, it is preferred as the Lewis acid a halogen derivative of elements of the III., IV., V., VI., VII. or VIII. group of the Periodic Table of the Elements.

Von den Alkalimetallen eignen sich Natrium, Kalium, Lithium, Rubidium oder Cäsium, bevorzugt eignen sich insbesondere Lithium, Natrium und/oder Kalium. Von den Alkalimetallderivaten eignen sich insbesondere Naphthalin -Natrium, -Methylstyrol-Natrium, die Amide der Alkalimetalle oder Natrium oder Kalium, das in flüssigem Ammoniak gelöst ist.Of the alkali metals, sodium, potassium, lithium and rubidium are suitable or cesium, lithium, sodium and / or potassium are particularly suitable. Of the alkali metal derivatives, naphthalene-sodium, -methylstyrene-sodium, the amides of the alkali metals or sodium or potassium that exist in liquid ammonia is resolved.

Die Umsetzung wird in Tetrahydrofuran, Ammoniak, Hexan oder Benzol vorgenommen.The reaction is carried out in tetrahydrofuran, ammonia, hexane or benzene performed.

Nach besonderer bevorzugter Verfahrensweise wird als Lewis-Säure die Verbindung AsF5, SbF5, UF6, SbCl5, AlCl3, BF3, FeCl3, CF3SO3H, VoCl3, HClO4, NO+SbF6, NO2+SbF6-, NO+AsF6-, XeF4, NO+PF6, I2, Br2, ICL, PF5, CrO2Cl2, NO@+PF@-@ NO+BF@- NO+Cl@- (C@@)@SO@ NbF@ T@F- @F@ F@Cl- T@Cl-NO2 PF6 , NO BF4 , NO+ClO4-, (CF3)2S04, NbF5, TaF5, WF6, FeC13, TaCl3, WCl6 oder BF3/CrOC12 eingesetzt.According to a particularly preferred procedure, the Lewis acid is the Compound AsF5, SbF5, UF6, SbCl5, AlCl3, BF3, FeCl3, CF3SO3H, VoCl3, HClO4, NO + SbF6, NO2 + SbF6-, NO + AsF6-, XeF4, NO + PF6, I2, Br2, ICL, PF5, CrO2Cl2, NO @ + PF @ - @ NO + BF @ - NO + Cl @ - (C @@) @ SO @ NbF @ T @ F- @ F @ F @ Cl- T @ Cl-NO2 PF6, NO BF4, NO + ClO4-, (CF3) 2S04, NbF5, TaF5, WF6, FeC13, TaCl3, WCl6 or BF3 / CrOC12 are used.

Als Lewis-Säuren nach dem erfindungsgemäßen Verfahren kommen ferner in Frage: Die Reaktion kann mit den gasförmigen Reaktanten oder mit Hilfssäuren wi EF, ROSeF5, HOTeF5, CF3SO3H, CF3COOll, CF3P03H> (CF3)2, HPF6, H2SiF6, H2PO2F2, oder gegebenenfalls in inerten Lösungsmitteln, wie SO2, S02C12, S02F2, S02CIF, CFC13 (Frigen 11), HF, CE3CN, CH3N02, C2H5N02 durchgeführ werden.Also suitable as Lewis acids in the process according to the invention are in question: The reaction can be carried out with the gaseous reactants or with auxiliary acids like EF, ROSeF5, HOTeF5, CF3SO3H, CF3COOll, CF3P03H> (CF3) 2, HPF6, H2SiF6, H2PO2F2, or optionally in inert solvents such as SO2, S02C12, S02F2, S02CIF, CFC13 (Frigen 11), HF, CE3CN, CH3N02, C2H5N02.

Die Umsetzung der dehydrierten Polymeren, also der dehydrierten Polymeri sate der Propargylhalogenide mit den Lewis-Säuren oder mit den Alkalimetallen oder Alkalimetallderivaten wird auch als Komplexierung', bezeichnet, die Lewis-Säuren und Alkalimetalle als "Komplexierungsmittel".The implementation of the dehydrated polymers, i.e. the dehydrated polymers sate the propargyl halides with the Lewis acids or with the alkali metals or Alkali metal derivatives is also called complexation ', the Lewis acids and alkali metals as "complexing agents".

Die erfindungsgemäß hergestellten elektrisch leitfähigen polymeren Systeme mit elektrischen Leitfähigkeiten größer als 10-2 S/cm sind zur antistatischen Ausrüstung von Kunststoffen, zur Herstellung von Sonnenzellen, zur Umwandlung und Fixierung von Strahlung sowie zur Herstellung elektrischer und magnetischer Schalter, elektrischer Schalter oder Speicher geeignet. Durch die Zusätze der starken Lewis-Säure entstehen sog. p-Leiter (vgl. "Journal Chemical Education", 46, (1969), Nr. 2, Seite 82).The electrically conductive polymers produced according to the invention Systems with electrical conductivity greater than 10-2 S / cm are antistatic Equipment of plastics, for the manufacture of solar cells, for conversion and Fixation of radiation as well as for the production of electrical and magnetic switches, electrical switch or memory suitable. With the addition of the strong Lewis acid so-called p-conductors arise (cf. "Journal Chemical Education", 46, (1969), No. 2, page 82).

Die in den folgenden Beispielen genannten Teile sind Gewichtsteile, die Prozente sind Gewichtsprozente.The parts mentioned in the following examples are parts by weight, the percentages are percentages by weight.

Beispiele 1 bis 10 100 Teile Polypropargylchlorid, hergestellt durch Polymerisation von Propargylchlorid in Dimethylformamid mit Hilfe von 10 % Palladiumchlorid, bezogen auf Propargylchlorid, werden mit den in der Tabelle angegebenen Teilen eines Komplexierungsmittels versetzt und 3 Stunden am Rückfluß erhitzt. Anschließend wird die Lösung mit Wasser gewaschen und die organische Phase abgetrennt und eingeengt. Das so gewonnene und getrocknets Polymere mit der Struktur entsprechend der obigen Formel (II) wird dann mit 10 Teilen AsF5 versetzt. Hierdurch wird ein elektrisch leitfähiges Polymerisat erhalten.Examples 1 to 10 100 parts of polypropargyl chloride manufactured by Polymerization of propargyl chloride in dimethylformamide with the help of 10% palladium chloride, based on propargyl chloride, with the parts given in the table are a Complexing agent is added and the mixture is refluxed for 3 hours. Then will the solution is washed with water and the organic phase is separated off and concentrated. The thus obtained and dried polymer having the structure corresponding to the above Formula (II) is then mixed with 10 parts AsF5. This makes an electric conductive polymer obtained.

Die Dehydrierung mit Mangan-III-acetat erfolgt bei 1100C in Toluol. Werden andere Dehydrierungsmittel eingesetzt, so erfolgt das Dehydrieren bei Temperaturen von 150 bis 20O0O. Vor dem Komplexieren werden die Dehydriei mittel durch Säure ausgewaschen. Das verbleibende organische Polymere wird dann mit dem angegebenen Komplexierungsmittel komplexiert.The dehydrogenation with manganese (III) acetate takes place at 1100C in toluene. If other dehydrating agents are used, the dehydration takes place at temperatures from 150 to 20O0O. Before complexing, the dehydrating agents are acidified washed out. The remaining organic polymer is then given with the Complexing agent complexed.

In der folgenden Tabelle werden die Eigenschaften der erfindungsgemäß hergestellten Polymeren zusammengefaßt.The following table shows the properties of the invention produced polymers summarized.

Aus der Gruppe VIII KrF2, XeOF4, XeF6, XeO2F2, HXeO4 sowie der Gruppe VII ClF3, ClF5, BrF3, IF5, BrCl, BrI, HClO3, HClO4, HIO3, HIO4, FClO3 wie aus der Gruppe VI FSO3H, R(SO2F)x = 2 für NH; x = 3 für CH mit R = NH, CH, sowie den Nebengruppen OsF5, CrF5, MoF6, WF5, MoF5, VF5, NbF5, TaF5, CrO2F2, CrO3, PtCl4, AuCl3, TaCl5, MoCl5.From group VIII KrF2, XeOF4, XeF6, XeO2F2, HXeO4 and the group VII ClF3, ClF5, BrF3, IF5, BrCl, BrI, HClO3, HClO4, HIO3, HIO4, FClO3 as from the Group VI FSO3H, R (SO2F) x = 2 for NH; x = 3 for CH with R = NH, CH, and the subgroups OsF5, CrF5, MoF6, WF5, MoF5, VF5, NbF5, TaF5, CrO2F2, CrO3, PtCl4, AuCl3, TaCl5, MoCl5.

Es kommen ferner in Frage: Aus der VI. Gruppe CF3(CF2)nSO3H, ClSO3H, Cl2CHSO3H, sowie der V. Gruppe HP02F2, BiX3 mit X = F, C1, Br oder I.The following also come into question: From VI. Group CF3 (CF2) nSO3H, ClSO3H, Cl2CHSO3H, as well as the V group HP02F2, BiX3 with X = F, C1, Br or I.

VI. Gruppe SiF4, H2SiF6, GeX4, SnX4, PbX4 mit X = F, C1, Br der III. Gruppe BX3, AlX3, GaX3, T1X3 mit X = F, C1, Br, I sowie der Nebengruppen RaCl4, RaOF4, VOF3, NbOF3, TaOF3, VCl3, VF3, NbCl5, TaCl5, NbOCl3, UCl5, CuX2, ZnX2, FeX3, RuX2, OsX2 (X = Cl, Br, I), TiX4, ZrX4, HfF4 (X = F, C1, Br, I), Y3X, LaX3 Lanthanide X3 (X = F, Cl, Br, I),VI. Group SiF4, H2SiF6, GeX4, SnX4, PbX4 with X = F, C1, Br of III. Group BX3, AlX3, GaX3, T1X3 with X = F, C1, Br, I and the subgroups RaCl4, RaOF4, VOF3, NbOF3, TaOF3, VCl3, VF3, NbCl5, TaCl5, NbOCl3, UCl5, CuX2, ZnX2, FeX3, RuX2, OsX2 (X = Cl, Br, I), TiX4, ZrX4, HfF4 (X = F, C1, Br, I), Y3X, LaX3 lanthanides X3 (X = F, Cl, Br, I),

Claims (7)

Patentansprüche Verfahren zur Herstellung von elektrisch leitfähigen Polymeren mit elektrischen Leitfähigkeiten größer als 10 2 S/cm, dadurch gekennzeichnet, daß Polymerisate von Propargylhalogeniden dehydriert und anschließend mit einer Lewis-Säure oder einem Alkalimetall oder Alkalimetallderivat in Mengen von 1 bis 70 Gew.%, bezogen auf das dehydrierte Polymere, ungesetzt werden. Method for the production of electrically conductive Polymers with electrical conductivities greater than 10 2 S / cm, characterized in that that polymers of propargylic halides are dehydrated and then with a Lewis acid or an alkali metal or alkali metal derivative in amounts of 1 to 70% by weight, based on the dehydrated polymer, are unset. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Dehydrierungsmittel Schwefel, Selendioxid, Mangandioxid oder Mangan(III)-acetat verwendet. 2. The method according to claim 1, characterized in that as Dehydrating agents sulfur, selenium dioxide, manganese dioxide or manganese (III) acetate used. 3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man als Lewis--Säure ein Halogenderivat von Elementen der III., IV., V., VI., VII. 3. The method according to claim 1, characterized in that as Lewis acid a halogen derivative of elements of III., IV., V., VI., VII. oder VIII. Gruppe des Periodensystems der Elemente verwendet. or VIII. Group of the Periodic Table of the Elements is used. 4. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man Lewis--Säure in Mengen von 5 bis 45 Gew.%, bezogen auf das Polymere, verwendet. 4. The method according to claim 1, characterized in that one Lewis acid Used in amounts of 5 to 45% by weight, based on the polymer. 5. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß ein Alkalimetall oder ein Alkalimetallderivat in Mengen von 5 bis 45 Gew.%, bezogen auf das Polymere, verwendet. 5. The method according to claim 1, characterized in that an alkali metal or an alkali metal derivative in amounts of 5 to 45% by weight, based on the polymer, used. 6. Verwendung der nach Anspruch 1 hergestellten elektrisch leitfähigen Polymeren in der Elektrotechnik zur Herstellung von Sonnenzellen, zu Umwandlung und Fixierung von Strahlung und zur Herstellung eiektrischer und magnetischer Schalter und elektrischer Speicher.6. Use of the electrically conductive produced according to claim 1 Polymers in electrical engineering for the production of solar cells, for conversion and fixation of radiation and for making electrical and magnetic switches and electrical storage. 7. Verwendung der nach Anspruch 1 hergestellten elektrisch leitfähigen Polymeren zur antistatischen Ausrüstung von Kunststoffen. 7. Use of the electrically conductive produced according to claim 1 Polymers for the antistatic treatment of plastics.
DE19833344753 1983-12-10 1983-12-10 Preparation of electroconductive polymers, and their use in electrical engineering and as antistatics Withdrawn DE3344753A1 (en)

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