EP0183977B1 - Mélanges fusibles électriquement conducteurs - Google Patents

Mélanges fusibles électriquement conducteurs Download PDF

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Publication number
EP0183977B1
EP0183977B1 EP85113674A EP85113674A EP0183977B1 EP 0183977 B1 EP0183977 B1 EP 0183977B1 EP 85113674 A EP85113674 A EP 85113674A EP 85113674 A EP85113674 A EP 85113674A EP 0183977 B1 EP0183977 B1 EP 0183977B1
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
araliphatic
tcnq
fusible
aromatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP85113674A
Other languages
German (de)
English (en)
Other versions
EP0183977A1 (fr
Inventor
Friedrich Dr. Jonas
Jürgen Dr. Hocker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0183977A1 publication Critical patent/EP0183977A1/fr
Application granted granted Critical
Publication of EP0183977B1 publication Critical patent/EP0183977B1/fr
Expired legal-status Critical Current

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Classifications

    • 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
    • H01B1/121—Charge-transfer complexes

Definitions

  • a TCNQ molecule is reduced by iodide to the TCNQ anion with the release of iodine.
  • Another method consists in the reaction of nitrogen-containing heteroaromatics or tertiary amines with P-phenylene-1,4-dimalodinitrile of the formula H 2 TCNQ (11) and TCNQ, e.g. B.
  • TCNQ 1,11,12,12-tetracyano-2,6-naphthoquinone dimethane
  • Electron number is formed.
  • Melting points of suitable organic compounds are generally above 30 ° C., preferably above 60 ° C., but below the melting point of the TCNQ complex. A typical range is 60 to 180 ° C.
  • the organic compounds can be used individually or as mixtures.
  • the mixtures according to the invention with TCNQ complexes contain 0.5 to 99% by weight, preferably 10 to 90% by weight, of TCNQ complex of the formula III and 1 to 99.5% by weight, preferably 10 to 90% by weight. % of one or more of the organic compounds described.
  • TCNQ complexes suitable for the preparation of the mixtures according to the invention are known per se. Their composition can be determined by Formula III are described in which D is an electron donor or a cation and n is a number from 1 to 5, preferably 2.
  • CT complexes correspond to the formula wherein D + is a cation and in 1, 2, 3 or 4, in particular 1.
  • CT batch transfer
  • CT complexes whose donor part is easily accessible and which is derived from an organic compound containing nitrogen and / or oxygen and / or sulfur and / or phosphorus and is present as a cation.
  • these are the cations of the following compounds or the corresponding quaternary ammonium, sulfonium or phosphonium ions:
  • the mixtures according to the invention can be mixed by mixing the individual components in the solid state by known methods, for. B. by grinding, mortars.
  • the TCNQ complex can also be introduced into a melt of the organic compounds.
  • the conductivity of the mixtures can be varied within wide limits by changing the ratio of TCNQ complex to organic compound.
  • the mixtures can generally be kept in the melt for at least 5 minutes without losing their electrical properties. Repeated melting of the mixtures is also possible.
  • the melting points of the mixtures according to the invention depend on the mixing ratio and on the melting points of the individual components. However, they are always well below the melting points of the pure TCNQ complexes, which means that the thermal stress on the TCNQ complexes is lower and processing is easier.
  • the mixtures according to the invention can also contain further constituents, such as polymeric binders, stabilizers, pigments.
  • the mixtures according to the invention can be used to produce electrically conductive coatings on substrates by melting.
  • Suitable substrates include: glass, metals, metal oxides, organic polymers. Such substrates can be coated by applying melts of the mixtures according to the invention to preheated substrates. The mixtures according to the invention can also be applied to the substrates to be coated at room temperature and then melted in a preheated oven. Both processes lead to electrically conductive, well-adhering coatings.
  • the coatings produced in this way can be used in electrical engineering and electronics.
  • the conductivity of the mixtures was determined by means of two-electrode measurement at a pressure of 1960 bar (2000 kp / cm 2 ).
  • X g TCNQ complex of formula A and Y g of compound * are intimately mixed by mortar and then melted for z-minutes in a glass sample tube by heating in a metal bath of temperature T. Low-viscosity melts were obtained in all cases. The conductivities of the re-solidified melts were determined.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Claims (2)

1. Mélanges fusibles de haute conductibilité thermique composés de 0,5 à 99 % en poids d'un complexe de TCNQ de formule
Figure imgb0018
dans laquelle
D représente un donneur d'électrons ou un cation et
n est un nombre de 1 à 5,

et de 1 à 99,5 % en poids d'un ou plusieurs des composés organiques fusibles suivants, solides à la température ambiante:
hydrocarbures linéaires ou cycliques éventuellement substitués, esters d'acides carboxyliques aliphatiques, cétones et alcools linéaires ou cycliques, hydrocarbures aromatiques ou araliphatiques éventuellement substitués, cétones aromatiques ou araliphatiques éventuellement substituées, éthers aromatiques ou araliphatiques éventuellement substitués, thioéthers et sulfones aromatiques ou araliphatiques éventuellement substitués, esters d'acides carboxyliques aromatiques, nitriles d'acides carboxyliques aromatiques et composés hétérocycliques.
2. Mélanges fusibles suivant la revendication 1, caractérisés en ce que l'ion complémentaire relatif à l'anion radicalaire TCNQ est représenté par un cation organique, notamment par l'une des formules A à C,
Figure imgb0019
où
R représente un reste aliphatique, cycloaliphatique ou araliphatique de 1 à 30 atomes de carbone, éventuellement substitué, et
n a une valeur de 1 à 2.
EP85113674A 1984-11-09 1985-10-28 Mélanges fusibles électriquement conducteurs Expired EP0183977B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843440914 DE3440914A1 (de) 1984-11-09 1984-11-09 Schmelzbare, elektrisch leitfaehige mischungen
DE3440914 1984-11-09

Publications (2)

Publication Number Publication Date
EP0183977A1 EP0183977A1 (fr) 1986-06-11
EP0183977B1 true EP0183977B1 (fr) 1988-03-16

Family

ID=6249861

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85113674A Expired EP0183977B1 (fr) 1984-11-09 1985-10-28 Mélanges fusibles électriquement conducteurs

Country Status (4)

Country Link
US (1) US4663078A (fr)
EP (1) EP0183977B1 (fr)
JP (1) JPS61118904A (fr)
DE (2) DE3440914A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2564231B1 (fr) * 1984-05-10 1986-09-05 Commissariat Energie Atomique Films conducteurs de l'electricite comprenant au moins une couche monomoleculaire d'un complexe organique a transfert de charge et leur procede de fabrication
DE3607668A1 (de) * 1986-03-08 1987-09-10 Bayer Ag Schmelzbare, elektrisch leitfaehige mischungen
DE3828758A1 (de) * 1988-08-25 1990-03-01 Bayer Ag Verfahren zur erzeugung elektrisch leitender schichten auf substraten und in dem verfahren zu verwendende druckpasten
US5091285A (en) * 1989-04-28 1992-02-25 Fujitsu Limited Method of forming pattern by using an electroconductive composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES316614A1 (es) * 1964-08-24 1966-07-01 Gen Electric Un procedimiento para preparar una composicion electronicamente conductora.
US4026905A (en) * 1972-12-26 1977-05-31 Monsanto Company Electrically conducting organic salts
US4293452A (en) * 1980-01-31 1981-10-06 The United States Of America As Represented By The Secretary Of The Navy Electrically conductive polymeric compositions
US4359411A (en) * 1980-10-03 1982-11-16 The United States Of America As Represented By The Secretary Of The Navy Flexible semiconductive polymers
DE3133738A1 (de) * 1981-08-26 1983-03-10 Bayer Ag, 5090 Leverkusen Neue komplexsalze mit hoher elektrischer leitfaehigkeit
US4529538A (en) * 1983-08-09 1985-07-16 The United States Of America As Represented By The Secretary Of The Navy Electrically conductive polymer compositions
DE3335513A1 (de) * 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen Gegen hcn-abspaltung stabilisierte, tcnq-komplexe enthaltende organische polymere
DE3335589A1 (de) * 1983-09-30 1985-04-18 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von tcnq-komplexen

Also Published As

Publication number Publication date
JPS61118904A (ja) 1986-06-06
US4663078A (en) 1987-05-05
DE3440914A1 (de) 1986-05-15
DE3561911D1 (en) 1988-04-21
EP0183977A1 (fr) 1986-06-11

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