Perovskite solar cells (PSCs) have recently achieved over 26 % power conversion efficiency, challenging the dominance of silicon-based alternatives. This progress is significantly driven by innovations in hole transport materials (HTMs), which notably influence the efficiency and stability of PSCs. However, conventional organic HTMs like Spiro-OMeTAD and PTAA, although highly efficient, suffer from thermal degradation, moisture ingress, and high cost. This study explores the potential of iminodibenzyl, a moiety known for its strong electron-donating capabilities in pharmaceutical applications, as a novel HTM. A series of fluorene-based derivatives incorporating iminodibenzyl (TMF-2 and TDF-2) and diphenylamine (TMF-1 and TDF-1) units were synthesized and characterized. The new HTMs demonstrated commendable optical, electrochemical, and thermal properties, as well as enhanced photostability. Among them, TDF-2 achieved a power conversion efficiency (PCE) of 19.38 %, the highest of the new materials. Although these efficiencies are slightly lower than the benchmark PTAA (20.20 %), the study underscores the potential of iminodibenzyl to enhance photostability and increase HOMO levels, making it a promising candidate for future HTM development in PSCs.