We tried to refine our previous method, which suggests a guideline to design new high mobility hole carrier transport molecules (CTMs) from polarizability and dipole moment of CTM, by considering intermolecular interaction and molecular deformation effects as well as polarizability and dipole moment of CTM. The molecular structure differences between neutral CTMs and their cations were investigated by using semiempirical molecular orbital theory. Semiempirical molecular orbital theory was also used to analyze intermolecular interactions of CTM dimers, where the structures of CTM dimers were optimized by molecular mechanics and semiempirical molecular orbital calculations. Intermolecular interactions of CTM dimers and the molecular structure deformation effect were analyzed to consider how these factors affected hole mobility in molecularly doped polymers. Our results suggested that the effects of intramolecular reorganization and intermolecular interaction between neighboring CTMs upon hole mobility were smaller than those of the electronic cloud extension and dipole moment of CTM.