# US 4,395,497 A · Preparation of electrically conductive soluble heteropolyphenylenes

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- Number: US 4,395,497 A
- Document ID: US4395497A
- Status: Granted
- Kind: A
- Application number: 06/273,688
- Filed: 1981-06-15
- Granted: 1983-07-26
- Earliest claimed: 1980-07-08
- Assignees: BASF SE
- Inventors: Herbert Naarmann; Dieter Naegele; Klaus Penzien; Johannes Schlag
- Web page: https://patentgrep.com/patent/US4395497A

## CPC

- H01B 1/128: {comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes}
- C08G 61/123: {derived from five-membered heterocyclic compounds}
- C08L 65/00: Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C08L7/00 - C08L57/00, C08L61/00 take precedence); Compositions of derivatives of such polymers
- H01B 1/127: {comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes}
- H10K 85/111: {comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene}
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- Y02E 10/549: Organic PV cells
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A process for the preparation of electrically conductive heteropolyphenylenes, wherein from 0.5 to 5 per cent by weight of an activating additive is introduced, in the absence of moisture and of oxygen, into a heteropolyphenylene of the general formula ##STR1## where X is O, S, Se, SO or SO.sub.2 and Y has one of the meanings given for X or is NH, CH.sub.2, CO or C.sub.6 H.sub.4, and n is from 2 to 250. The activating additive is preferably one of the compounds AsF.sub.5, SbF.sub.5, UF.sub.6, HClO.sub.4, NO.sup.+ SbF.sub.6.sup.-, NO.sub.2.sup.+ SbF.sub.6.sup.-, NO.sup.+ PF.sub.6.sup.-, SbCl.sub.5, NO.sub.2.sup.+ PF.sub.6.sup.-, NO.sup.+ BF.sub.4.sup.-, NO.sup.+ ClO.sub.4.sup.-, (CF.sub.3).sub.2 SO.sub.4, 2,4,6-trinitrophenol, 2,4,6-trinitrophenylsulfonic acid and 2,4,6-trinitrophenylcarboxylic acid, or is sodium, potassium, rubidium, cesium, calcium or barium or one of their amides, the latter being added, if appropriate, in tetrahydrofuran, dimethoxyglycol, anthracene, naphthalene or 2-methylstyrene. The conductive heteropolyphenylenes may be used in the electrical industry for the production of solar cells, for conversion and fixing of radiation and for the production of electrical and magnetic switches, or may be used for the antistatic treatment of plastics.

## Claims

### Claim 1

A process for the preparation of an electrically conductive heteropolyphenylene having a conductivity greater than 10.sup.-2 S/cm, wherein from 0.5 to 5 percent by weight, based on heteropolyphenylene employed, of an activating additive is introduced, in the absence of moisture and of oxygen, into a heteropolyphenylene of the formula ##STR6## where X is O, S or Se, Y has one of the meanings given for X or is SO, SO.sub.2 NH, CH.sub.2, CO or phenylene and n is from 2 to 250.

### Claim 2 (depends on 1)

A process as claimed in claim 1, wherein the activating additive is a strong Lewis acid, having a pK.sub.a of from 10 to 14.

### Claim 3 (depends on 1, 2)

A process as claimed in claim 1 or 2, wherein the Lewis acid is AsF.sub.5, SbF.sub.5, UF.sub.6, HClO.sub.4, NO.sup.+ SbF.sub.6.sup.-, NO.sup.+ AsF.sub.6.sup.-, NO.sub.2 AsF.sub.6.sup.-, NO.sub.2.sup.+ SbF.sub.6.sup.-, NO.sup.+ PF.sub.6.sup.-, SbCl.sub.5, NO.sub.2.sup.+ PF.sub.6.sup.-, NO.sup.+ BF.sub.4.sup.-, NO.sup.+ ClO.sub.4.sup.-, (CF.sub.3).sub.2 SO.sub.4, 2,4,6-trinitrophenol, 2,4,6-trinitrophenylsulfonic acid or 2,4,6-trinitrobenzoic acid.

### Claim 4 (depends on 1)

A process as claimed in claim 1, wherein sodium, potassium, rubidium, cesium, calcium or barium or an amide thereof is introduced, as an activating additive, into the heteropolyphenylene (I).

### Claim 5 (depends on 1, 4)

A process as claimed in claim 1 or 4, wherein Na, K, Rb, Cs, Ca or Ba or an amide thereof is added in tetrahydrofuran, dimethoxyglycol, anthracene, naphthalene or 2-methylstyrene, in each case in a molar ratio of the former component to the latter component of from 1:1 to 1:5.

### Claim 6 (depends on 1)

A process as claimed in claim 1, wherein n is from 5 to 50.

### Claim 7 (depends on 5)

A process as claimed in claim 5, wherein the molar ratio of the former component to the latter component is from 1:2 to 1:3.