The absorption, photoluminescence and electroluminescence properties of systematically modified poly(1,3,4-oxadiazole)s are reported and compared with low molar mass compounds. Poly(1,3,4-oxadiazole)s are functionalised by introducing pendent alkyl side chains and tetraphenylsilane or hexafluoroisopropylidene group (6F) into the main chain, respectively. The photo-and electroluminescence of single layer devices was found to be in the blue and green spectral range. A further strategy was to start with the optimisation of the substituents of low molar mass compounds followed by bonding the optimised structure to a flexible PMMA main chain. It was demonstrated that it is possible to preserve the optical properties of the oxadiazole unit and at the same time to improve film forming properties of the final polymer.