Dibenzothiophene oxide compound, and process for producing the same

Abstract

There are disclosed novel compounds, liquid crystal compositions, polymers, optically anisotropic products, and optical or liquid or liquid crystal elements that have large refractive index anisotropy, mix easily with other liquid crystals, have advantageous stability against light, and exhibit absorption at practically short wavelength in the ultraviolet region. The compounds are represented by the formula (1) and have a phenylacetylene structure, wherein difference ΔE in energy of HOMO of parts (1-1), (1-2) and (1-3) calculated by the method of molecular orbitals is not less than 0.3 electronvolt, and the polarizability anisotropy Δα of a molecule represented by the formula (1) calculated in the same way is not lower than 500 A.U.: (A 1 to A 4 : H, F, alkyl or alkoxy group of C1 to C10 optionally substituted with F; P 1 , P 2 ; structure fulfilling the conditions of HOMO energy and polarizability).

1 . A dibenzothiophene compound represented by the formula (A-1): 
       
         
           
           
               
               
           
         
         wherein A 1  to A 6  each independently stands for a hydrogen atom, a fluorine atom, an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom, X stands for a halogen atom, and Y stands for a halogen atom or a hydroxyl group. 
       
     
     
         2 . A dibenzothiophene compound represented by the formula (A-2): 
       
         
           
           
               
               
           
         
         wherein A 1  to A 6  each independently stands for a hydrogen atom, a fluorine atom, an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom, and X stands for a halogen atom. 
       
     
     
         3 . A method for producing the dibenzothiophene compound of  claim 1  comprising:
 diazotizing a dibenzothiophene compound represented by the formula (A-2) to obtain a diazonium salt,   
       
         
           
           
               
               
           
         
         wherein A 1  to A 6  each independently stands for a hydrogen atom, a fluorine atom, an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom, and X stands for a halogen atom, and 
         decomposing said diazonium salt in the presence of an anion corresponding to Y in the formula (A-1): 
       
       
         
           
           
               
               
           
         
         wherein A 1  to A 6  and X mean the same as those in the formula (A-2), and Y stands for a halogen atom or a hydroxyl group. 
       
     
     
         4 . A method for producing the dibenzothiophene compound of  claim 2  comprising reducing a dibenzothiophene oxide compound represented by the formula (A-3): 
       
         
           
           
               
               
           
         
         wherein A 1  to A 6  each independently stands for a hydrogen atom, a fluorine atom, an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom, and X stands for a halogen atom.