In the study, fluorine atoms with high electronegativity and the chiral side chain were introduced onto hexa(difluoroalkoxyphenyl)benzenes to show columnar liquid crystal phase due to hydrogen bonding and the close packing of chiral chain. The melting point lowerd and clearling points raised by modifying fluorine atoms with different numbers and positions. On the other part, different halogen atoms were induced on 1,2,3,4,5-pentaylpentakis(ethyne-2,1-diyl))pentabenzene. The clearing point increased with larger van der waals radius of halogen atom. The compound which was introduced one 2-fluoro-4-alkoxychainbenzene exhibited discotic nematic liquid crystal phase due to the weak hydrogen bonding from smaller numbers of fluorine atoms.