Substituted triphenylamines as building blocks for star shaped organic electronic materials

Abstract

A versatile synthetic protocol toward a series of various substituted triphenylamine derivatives serving as building blocks for organic electronic materials was developed. Key steps during synthesis were either Ullmann condensations or nucleophilic aromatic substitutions giving rise to structural modification of triphenylamines and their electronic nature. In turn, these scaffolds were exemplarily attached to a dendritic tris(2-thienyl)benzene core affording star shaped organic semiconducting materials which were characterized regarding their photo-physical, electro-chemical and thermal properties. A strong influence of the substituent's nature on both photo-physical and morphological thin film characteristic of star shaped target compounds was observed. The applicability of these materials in organic electronic devices was demonstrated in an organic field effect transistor configuration yielding a hole mobility of nearly 10⁻³ cm² V⁻¹ s⁻¹. The performance of the materials can be correlated to the substituents applied.