New conjugated polymers that incorporate dihexylanthradithiophene (DHADT) in the main chain were prepared by Stille, Sonogashira, and Yamamoto cross-coupling polymerization reactions. The polymerization chemistry is enabled by a soluble 5,11-dibromodihexylanthradithiophene monomer that is capable of cross-coupling reactions. Five readily soluble DHADT containing polymers were prepared and characterized experimentally and computationally. These polymers possess HOMO energies of −5.18 eV to −5.43 eV and LUMO energies of −3.0 eV to −2.82 eV. The notable optical features include broad absorption and band gaps ranging from 1.62 eV to 2.15 eV. Polymers were tested in organic field effect transistors and were found to operate in the p-type regime.