Polymers comprising olig-p-phenylene units, a process for their

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate

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528125, 528212, 528218, 528219, 528220, 528225, 528370, 528394, C08G 802, C08G 6100, C08G 6538

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061144908

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BRIEF SUMMARY
There is a great industrial need for large-area solid-state light sources for a range of applications, predominantly in the field of display elements, VDU technology and light engineering. The demands made of these light sources can at present not be met completely satisfactorily by any of the existing technologies.
As an alternative to conventional display and/or lighting elements such as incandescent lamps, gas discharge lamps and non-self-illuminating liquid crystal display elements, use has for some time been made of electroluminescence (EL) materials and devices such as light-emitting diodes (LEDs).
Apart from inorganic electroluminescence materials and devices, low molecular weight, organic electroluminescence materials and devices have been known for about 30 years (see, for example, U.S. Pat. No. 3,172,862). However, until recently such devices have been greatly restricted in their practical usability.
WO 90/13148 and EP-A 0 443 861 describe electroluminescence devices comprising a film of a conjugated polymer as light-emitting layer (semiconductor layer). Such devices offer numerous advantageous such as the opportunity to produce large-area, flexible displays simply and inexpensively. In contrast to liquid crystal displays, electroluminescent displays are self-illuminating and therefore require no additional backward lighting source.
A typical electroluminescence device as described in WO 90/13148 comprises a light-emitting layer in the form of a thin, coherent polymer film (semiconductor layer) comprising at least one conjugated polymer. A first contact layer is in contact with a first surface of the semiconductor layer and a second contact layer is in contact with a further surface of the semiconductor layer. The polymer film of the semiconductor layer has a sufficiently low concentration of extrinsic charge carriers for charge carriers to be introduced into the semiconductor layer on application of an electric field between the two contact layers, so that one contact layer becomes positive compared with the other and the semiconductor layer emits radiation. The polymers used in such devices are conjugated. For the purposes of the present invention, a conjugated polymer is a polymer which has a delocalized electron system along the main chain. The delocalized electron system gives the polymer semiconductor properties and enables it to transport positive and/or negative charge carriers with high mobility.
WO 90/13148 describes poly(p-phenylene-vinylene) as polymer material for the light-emitting layer, and it is proposed that the phenyl group in such a material be replaced by a heterocyclic or condensed, carbocyclic ring system. In addition, poly(p-phenylene), PPP, is also used as electroluminescent material (G. Grem, G. Ledetzky, B. Ullrich, G. Leising, Synth. Met. 1992, 51, 383) The main problem in the synthesis and processing of PPP is that this material is insoluble and infusible even at very low degrees of polymerization. Using precursor routes (see, for example, D. G. H. Ballard et al., J. Chem. Soc. Chem. Com. 1983, 954), it has been possible to synthesize relatively high molecular weight PPP and process it at the stage of a prepolymer. However, these materials display incomplete aromatization and/or ortho-linkages and also other structural defects. In order to increase the processability of the PPP and to make possible the synthesis of material having a higher degree of polymerization, derivatives having alkyl or alkoxy side chains and an increased solubility have already been prepared (F. L. Klavetter, G. G. Gustavson, A. J. Heeger, PMSE-Meeting Chicago 1993, 69, 153).
GB-A-1 092 824 describes poly(p-biphenylene-vinylene) which can be prepared by dehydrohalogenation of dihalo-p-xylene derivatives or by the Wittig reaction (H. H. Horhold, J. Opfermann, Faserforschung und Textiltechnik 1974, 25, 108). However, the first method does not achieve complete elimination. Furthermore, in both syntheses the content of double bonds having a cis configuration is sometimes considerable. In addition,

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