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

  • Andrew C. Grimsdale
  • Klaus MüllenEmail author
Chapter
Part of the Advances in Polymer Science book series (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.

Poly(para-phenylene)s Ladder polymers Photoluminescence Electroluminescence Light-emitting diodes 

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

Mn

number-averaged molecular weight

Mw

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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Notes

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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© Springer-Verlag Berlin Heidelberg  2006

Authors and Affiliations

  1. 1.Max-Planck-Institut für PolymerforschungMainzGermany

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