Using 9,9-dialkyl-functionalized fluorenes as monomers, novel fluorene-based oligomers were prepared in order to improve the thermal stability of a typical hole-transport material (HTM), N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine (TPD), in organic light emitting diodes (OLEDs). 2,7-Bis(diphenylamino)fluorene was utilized as a TPD unit throughout the present synthetic work. 9,9-Bis(2-methylallyl)fluorene and its TPD congener underwent a new cyclopolymerization reaction affording six-membered oligomers under acid catalysis with p-toluenesulfonic acid. Intermolecular Suzuki coupling of a 9,9-bis(p-bromobenzyl)fluorene analogue with the corresponding bis-boronate afforded a new oligomer containing the TPD substructure. These oligomers (3 and 6) for use as HTMs have high glass-transition temperatures (T-g's) (147 and 167 degrees C, respectively); the values are much higher than the T-g for TPD (63 degrees C). These materials are soluble in organic solvents to allow easy processing for preparing layered devices, though their electroluminescent performances were lower than that of the single molecule TPD.