Three novel 2-trifluoromethyl-activated bisfluoro monomers have been synthesized successfully using a Suzuki-coupling reaction of 4-fluoro-3-trifluoromethyl phenyl boronic acid with 4,4’-dibromo-p-terphenyls with varied phenyl substitution on the middle phenylene ring. Three monomers were converted to a series of phenyl substituted poly(arylene ether)s by nucleophilic displacement of the fluorine atoms on the benzene ring with 1,1 dihydroxydiphenyl cyclododecane. Thermal analysis studies indicated that these polymers did not show melting endotherms but showed ultrahigh Tg values up to 320ºC in DSC and good thermal stability up to 460ºC for 5% weight loss in TGA under nitrogen atmosphere. These polymers are soluble in a wide range of organic solvents. Transparent and flexible films were easily prepared by solution casting from chloroform solution of each of the polymers. The UV absorption spectra of thin films showed no absorption and transparencies greater than 90% in the visible light region of the spectrum. The refractive indexes of these polymer thin films were identified by an elipsometer, proving non-birefringence; the measured surface contact angles and estimated surface energies implied that there are weak polarities and hydrophobic properties. According to the above-mentioned results, polymers constructed from poly arylene ethers with high transparencies within the range of visible light, good thermal stabilities (high Tg), low polarities, and hydrophobicities were successfully prepared. This reveals the great potential of such materials in industrial applications, such as plastic substrate for devices.