Synthesis and properties of new derivatives of poly[9‐(2,3‐epoxypropyl)carbazole]

BACKGROUND: Carbazole derivatives are well known to exhibit interesting electro‐ and photo‐active properties due to their hole‐transporting ability, strong absorption in the ultraviolet spectral region and blue‐light emission. One of the most widely studied materials among carbazole‐containing oligomers is poly9‐(2,3‐epoxypropyl)carbazole] (PEPK). The main field of application of this oligomer is electrophotographic microfilming. It is also used for the manufacture of multicolour slides and in the photothermoplastic recording of information. Unfortunately, due to its high ionization potential, which reaches 5.86 eV, the possibilities of application of this compound in optoelectronic devices are rather limited. RESULTS: PEPK‐based charge transporting oligomers, incorporating hydrazone moieties, are reported. The oligomers were prepared by chemical modification of PEPK. The materials obtained were examined using various techniques including differential scanning calorimetry and ultraviolet, infrared and NMR spectroscopy. Electron photoemission spectra of layers of the synthesized oligomers showed ionization potentials (I_p) in the range 5.4–5.5 eV. CONCLUSION: The synthesized oligomers possess a larger π‐conjugated system and show ionization potentials of ca 5.4 eV. Therefore, they are more suitable for use in optoelectronic devices with quicker photoresponse than unmodified PEPK. Copyright © 2008 Society of Chemical Industry