Four pyrene-based discotic compounds with trialkylsilylethynyl groups in the side chains were prepared and characterized by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. All of the compounds were highly soluble in organic solvents, and two of the compounds exhibited a columnar phase, Colr, and the others were crystalline. The hole transport ability in the liquid-crystalline phases was determined by the time-of-flight (TOF) method to be on the order of 10-2cm2V-1s-1, the highest hole mobilities for pyrene derivatives yet observed.