For an improved performance of organic tandem solar cells, efficient organic infrared absorber materials are necessary. A promising class already used successfully in organic solar cells are 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs). Based on a comparative study of the intramolecular electronic properties as well as the intermolecular coupling in the crystal phase of three potential candidates, we find that the benzannulation of the molecular core improves both electron and hole transfer. As the frontier molecular orbitals are delocalized over the entire molecule also by attaching additional functional groups to the molecular core, the intermolecular coupling and especially the performance in amorphous phase can be optimized further. However, an immobilization of these substituents is necessary to regulate an increase in the reorganization energy for hole transfer. Based on these design rules, BODIPYs with optimized charge transfer properties can be synthesized increasing also the performance of the devices.