Three low-cost propeller-shaped small molecules based on a triphenylamine core and the high-performance donor molecule 7,7′-[4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl]bis[6-fluoro-4-(5′-hexyl-[2,2′-bithiophen]-5-yl)benzo[c][1,2,5]thiadiazole] (DTS(FBTTh2)2) were investigated as hole-transporting materials in perovskite solar cells. Each hole-transporting material was designed with highly modular side arms, allowing for different bandgaps and thin-film properties while maintaining a consistent binding energy of the highest occupied molecular orbitals to facilitate hole extraction from the perovskite active layer. Perovskite solar cell devices were fabricated with each of the three triphenylamine-based hole-transporting materials and DTS(FBTTh2)2 and were compared to devices with 2,2′,7,7′-tetrakis(N,N-di-p-methoxyphenylamine)-9,9′-spirobifluorene (spiro-OMeTAD) hole-transporting layers. Each of our triphenylamine hole-transporting materials and DTS(FBTTh2)2 displayed surface morphologies that were considerably rougher than that of spiro-OMeTAD; a factor that may contribute to lower device performance. It was found that using inert, insulating polymers as additives with DTS(FBTTh2)2 reduced the surface roughness, resulting in devices with higher photocurrents.