Unconventionally modified dibenzoylmethane (dbm) ligands have been synthesized and successfully utilized as ancillary ligands for neutral iridium(III) complexes of the formula [Ir(dFppy)2(LX)], where dFppyH is 2‐(2,4‐difluorophenyl)pyridine and LX is tribenzoylmethane (tbm) or 1‐phenyl‐3‐(4‐(pyridin‐2‐yl)phenyl)propane‐1,3‐dione (pydbm). The modification of the ligands aims to prevent or enhance possible intermolecular interactions between the dFppy and/or the LX moiety in comparison with the previously reported [Ir(dFppy)2(dbm)] complex. The aggregation induced emission (AIE) properties of these complexes are significantly modulated, as a consequence of the different π–π interactions revealed by X‐ray crystallography.