In this article, a series of fluorene/2,5-dithenyl-1H-pyrrole-based electroactive polymers (HS-X) with different feed ratio of SC12F/OF were synthesized via Suzuki coupling reactions. Chemical characterization of polymers was elucidated by(1)H NMR and Fourier-transform infrared spectroscopy. Electrochemical and electrophysical characterization of the synthesized polymers were investigated by cyclic voltammetry, UV-vis spectroscopy, and fluorescence spectroscopy. Thermal stability of polymers were studied with differential scanning calorimetry and manipulation of the Tg values of HS-X polymers was managed by increasing the numbers of the spiroalkylated fluorene (SAF) moieties incorporated into the polymer backbone. Five different conjugated polymers (HS-1, HS-2, HS-3, HS-4, and HS-5) were used as hole transport layer material in the fabrication of organic light-emitting diode (OLED) devices. The energy levels of the highest occupied molecular orbital as well as the lowest unoccupied molecular orbital and photoluminescence intensities were independent of the number of SAF units. OLED devices based on HS-X polymers were fabricated according to ITO/PEDOT:PSS/HS-X/Alq3/LiF:Al device configuration. Their electroluminescence performances were investigated and the best performance were obtained with the polymer containing 20% SC12F (HS-4) in an OLED device with a turn on voltage of 11.8 V, a maximum luminance of 1202 cd/m(2)and a maximum luminous efficiency of 0.30 cd/A compared to other polymers with different feed ratio.