Electrophotographic organophotoreceptors with novel charge transport compounds

Abstract

A novel charge transport compound, a novel process using that novel compound and an organophotoreceptor includes: (a) a novel charge transport compound having the formula  where R 1 and R 2 are selected so that R 1 and R 2 form, with the included nitrogen atom, a group selected from the group consisting of heterocyclic rings, aromatic rings, and dinaphthylamine; or R 1 comprises an aryl group and R 2 comprises a group selected from the group consisting of sulfolanyl, 4-(9H-fluoren-9-ylidene)benzyl, pyrrolyl, pyrazolyl, benzotriazolyl, stilbenyl, tetrazolyl; or R 1 comprises hydrogen, an alkyl group, an aryl group and R 2 comprises sulfonylphenyl.  R 3 is hydrogen, an alkyl group, an aryl group, a heterocyclic group or a hydrocarbon group; and  Q is a 3-carbazole group; (b) a charge generating compound; and (c) an electrically conductive substrate.

1 . An electrophotographic imaging process comprising: 
 (a) applying an electrical charge to a surface of an organophotoreceptor comprising 
 (i) a charge transport compound having the formula  
                     
    where R 1  comprises an aryl group and R 2  comprises a group selected from the group consisting of sulfolanyl, 4-(9H-fluoren-9-ylidene)benzyl, pyrrolyl, pyrazolyl, benzotriazolyl, stilbenyl, and tetrazolyl group; or R 1  comprises hydrogen atom, an alkyl group, or an aryl group and R 2  comprises a sulfonylphenyl group;     R 3  is hydrogen, an alkyl group, an aryl group, a heterocyclic group or a hydrocarbon group; and     Q is a 3-carbazole group; 
 (ii) a charge generating compound; and  
 (iii) an electrically conductive substrate;  
   (b) imagewise exposing said surface of said organophotoreceptor to radiation to dissipate charge in selected areas and thereby form a pattern of charged and uncharged areas on said surface;    (c) contacting said surface with a liquid toner comprising a dispersion of colorant particles in an organic liquid to create a toned image; and    (d) transferring said toned image to a substrate.    
     
     
         2 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a sulfolanyl group.  
     
     
         3 . The electrophotographic imaging process of  claim 2  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2  and L 3  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         4 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a 4-(9H-fluoren-9-ylidene)benzyl group.  
     
     
         5 . The electrophotographic imaging process of  claim 4  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2  and L 3  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         6 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a pyrrolyl group.  
     
     
         7 . The electrophotographic imaging process of  claim 6  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2 , L 3  and L 4  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         8 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a pyrazolyl group.  
     
     
         9 . The electrophotographic imaging process of  claim 8  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2 , L 3  and L 4  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         10 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a benzotriazolyl group.  
     
     
         11 . The electrophotographic imaging process of  claim 10  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2 , L 3  and L 4  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         12 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a stilbenyl group.  
     
     
         13 . The electrophotographic imaging process of  claim 12  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2  and L 3  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         14 . The electrophotographic imaging process of  claim 1  wherein R 2  comprises a tetrazolyl group.  
     
     
         15 . The electrophotographic imaging process of  claim 14  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises an aryl group, and L 2  and L 3  are, each independently, selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         16 . The electrophotographic imaging process of  claim 1  wherein R 1  comprises hydrogen, an alkyl or an aryl and R 2  comprises a sulfonylphenyl group.  
     
     
         17 . The electrophotographic imaging process of  claim 16  wherein the charge transport compound has a central nucleus of the formula:  
       
         
           
           
               
               
           
         
       
       wherein L 1  comprises a hydrogen atom, an alkyl group, or an aryl group, and L 2  is selected from the group consisting of hydrogen and hydrocarbons.  
     
     
         18 . The electrophotographic imaging process of  claim 1  wherein the charge transport compound is a compound selected from the group consisting of