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Polyphenylene-type Emissive Materials: Poly(para-phenylene)s,Polyfluorenes, and Ladder Polymers

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Emissive Materials Nanomaterials

Part of the book series: Advances in Polymer Science ((POLYMER,volume 199))

Abstract

This ‘chapter’ reviews the synthesis of the various classes of polyphenylene-based materials that have been investigated as active materials in light-emitting applications. In particular, it is shown how the electronic properties may be controlled by synthetic design. Insoluble poly(para-phenylene) can be made by a variety of precursor routes. Attachment of solubilising side chains gives soluble polyphenylenes in which a high degree of torsion between adjacent benzene rings produced by steric interactions between the substituents strongly reduces their electronic interaction. The phenylene units can be made coplanar by bridging them with methine or other bridges to produce ladder-type polymers, which show excellent photophysical properties, but strong intermolecular interactions lead to problems in obtaining blue emission. Similar problems are seen for ‘stepladder’ polymers such as polyfluorenes with only partial bridging of the phenylene rings. These interactions may be controlled by introduction of bulky substituents. The electroluminescence efficiency of these materials can also be enhanced by use of charge-transporting substituents. Copolymerisation with lower-band-gap units enables tuning of the emission colour across the entire visible range.

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Abbreviations

Ac:

acetyl

AIBN:

azabis(isobutyronitrile)

Boc:

tert-butoxycarbonyl

Bu:

butyl

sec-Bu:

sec-butyl

tBu:

tert-butyl

Cp:

cyclopentadienyl

DMSO:

dimethyl sulfoxide

ECL:

effective conjugation length

EL:

electroluminescence

eV:

electron volt

HOMO:

highest occupied molecular orbital

IR:

infrared

ITO:

indium tin oxide

LB:

Langmuir–Blodgett

LEC:

light-emitting electrochemical cell

LED:

light-emitting diode

LPPP:

ladder-type poly(para-phenylene)

LUMO:

lowest unoccupied molecular orbital

MALDI-TOF:

matrix assisted laser desorption ionisation–time of flight mass spectrometry

Me:

methyl

Me-LPPP:

methyl-substituted LPPP

M n :

number-averaged molecular weight

M w :

weight-averaged molecular weight

NMR:

nuclear magnetic resonance spectroscopy

PANI:

polyaniline

PDAF:

poly(dialkylfluorene)

PEDOT:

poly(3,4-ethylenedioxythiophene)

PEO:

poly(ethylene oxide)

PF:

polyfluorene

Ph:

phenyl

Ph-LPPP:

phenyl-substituted LPPP

PIF:

polyindenofluorene

PMMA:

poly(methyl methacrylate)

PPP:

poly(para-phenylene)

PPV:

poly(para-phenylene vinylene)

PS:

polystyrene

PSS:

poly(styrene sulfonate)

PVK:

poly(N-vinyl carbazole)

TGA:

thermal gravimetric analysis

UV-VIS:

ultraviolet–visible

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Acknowledgments

We gratefully acknowledge the financial support given to our research into emissive polyphenylenes by the Bundesministerium für Bildung und Forschung. We also thank Prof. Ullrich Scherf for communicating to us some of his unpublished results and manuscripts.

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  1. Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany

    Andrew C. Grimsdale & Klaus Müllen

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Correspondence to Klaus Müllen .

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Grimsdale, A.C., Müllen, K. (2006 ). Polyphenylene-type Emissive Materials: Poly(para-phenylene)s,Polyfluorenes, and Ladder Polymers. In: Emissive Materials Nanomaterials. Advances in Polymer Science, vol 199. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_076

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