We introduce a new family of stable high-mobility organic pi-type semiconductors based on the electron-rich 10,15-dihydro-5H-diindolo[3,2-a:3',2'-c]carbazole (triindole) extended pi-conjugated system. This platform tends to form columnar stacks of the aromatic cores maximizing pi-orbital overlap between adjacent molecules, thus paving the way for the one-dimensional migration of charge carriers along the columns. In addition these compounds have two different types of positions that can be functionalized independently offering the possibility of tuning their electronic properties as well as their morphology through chemical functionalization. The integration of the optimized triindole derivatives into solution processed devices as active layer is explored in this work.