Electrophotographic photosensitive member and process for producing the same

Abstract

An electrophotographic photosensitive member, including: a conductive substrate; an undercoat layer formed on the conductive substrate, which contains a binder resin and metal oxide particles treated with an organic metal compound represented by formula (1): where M is —SiR 3 , —TiR 3 or Al; R is a hydrogen atom or a C 1 to C 6 alkyl group; R 1 and R 2 are each, independently, a C 1 to C 6 alkyl group; R 3 is a C 1 to C 6 alkyl group which may be substituted with an alkoxy group or a C 1 to C 6 alkoxy group which may be substituted with an alkoxy group; and a photosensitive layer formed on the undercoat layer.

What is claimed is:  
     
         1 . An electrophotographic photosensitive member, comprising: 
 a conductive substrate;    an undercoat layer on the conductive substrate, comprising a binder resin and metal oxide particles treated with an organic metal compound represented by formula (1);  
                 
   wherein    M is —SiR 3 , —TiR 3  or Al;    R is a hydrogen atom or a C 1  to C 6  alkyl group;    R 1  and R 2  are each, independently, a C 1  to C 6  alkyl group;    R 3  is a C 1  to C 6  alkyl group which may be substituted with an alkoxy group or a C 1  to C 6  alkoxy group which may be substituted with an alkoxy group; and    a photosensitive layer on the undercoat layer.    
     
     
         2 . The electrophotographic photosensitive member of    claim 1   , wherein the organic metal compound is an organic silicon compound represented by formula (2):  
                   
       wherein  
       R 4  and R 5  are each, independently, methyl or ethyl; and 
 R 6  is selected from the group consisting of methyl, ethyl, methoxy and ethoxy.  
 
     
     
         3 . The electrophotographic photosensitive member of    claim 1   , wherein the metal oxide particles are titanium oxide particles.  
     
     
         4 . The electrophotographic photosensitive member of    claim 1   , wherein the metal oxide particles have an average primary particle size of not more than 100 nm when measured from a TEM micrograph.  
     
     
         5 . The electrophotographic photosensitive member of    claim 1   , wherein the binder resin is an alcohol-soluble resin.  
     
     
         6 . The electrophotographic photosensitive member of    claim 1   , wherein M is —SiR 3 .  
     
     
         7 . The electrophotographic photosensitive member of    claim 1   , wherein R 3  is a C 1  to C 6  alkyl group.  
     
     
         8 . The electrophotographic photosensitive member of    claim 1   , wherein the weight ratio of the metal oxide particles treated with the organic metal compound to the binder resin is 0.5:1 to 10:1.  
     
     
         9 . The electrophotographic photosensitive member of    claim 1   , wherein the binder resin is selected from the group consisting of thermoplastic resins, cellulose-based resins, polyamide resins, epoxy resins, urethane resins, acrylic acid-based resins, methacrylic acid-based resins, thermosetting resins, and photo-curable resins.  
     
     
         10 . The electrophotographic photosensitive member of    claim 1   , wherein the photosensitive layer is a laminate comprising a charge-generating layer on the undercoat layer and a and a charge-transport layer on the charge-generating layer.  
     
     
         11 . The electrophotographic photosensitive member of    claim 1   , wherein the conductive substrate is aluminum, stainless steel, copper, nickel, or is a coated substrate obtained by forming a conductive layer comprising aluminum, copper, palladium, tin oxide, indium oxide on an insulating substrate  
     
     
         12 . The electrophotographic photosensitive member of    claim 1     1 , wherein the insulating substrate is a polyester film, paper, or glass.  
     
     
         13 . The electrophotographic photosensitive member of    claim 1   , wherein the binder resin is a polyamide resin.  
     
     
         14 . The electrophotographic photosensitive member of    claim 1   , wherein the binder resin is a polyamide resin containing a diamine component represented by formula (3):  
                   
       wherein  
                 
 
       and  
                 
 
       are each, independently, a substituted or unsubstituted cyclohexyl ring; and 
 R 7  and R 8  are each, independently, a hydrogen atom, an alkyl group, am alkoxy group or an aryl group.  
 
     
     
         15 . A process for producing the electrophotographic photosensitive member of    claim 1   , comprising forming the undercoat layer on the conductive substrate by coating.  
     
     
         16 . The process of    claim 15   , wherein the binder resin is an alcohol-soluble resin, and a coating solution comprising the binder resin and an alcohol as a main solvent is coated on the conductive substrate.  
     
     
         17 . A process for producing the electrophotographic photosensitive member of    claim 1   , comprising: 
 applying the undercoat layer on the conductive substrate, and    applying the photosensitive layer on the undercoat layer.    
     
     
         18 . A coating film, comprising: 
 a binder resin; and    metal oxide particles treated with an organic metal compound represented by formula (1) or formula (2):  
                 
   wherein    M is —SiR 3 , 'TiR 3  or Al;    R is a hydrogen atom or a C 1  to C 6  alkyl group;    R 1  and R 2  are each, independently, a C 1  to C 6  alkyl group;    R 3  is a C 1  to C6 alkyl group which may be substituted with an alkoxy group or a C 1  to C 6  alkoxy group which may be substituted with an alkoxy group; or  
                 
   wherein    R 4  and R 5  are each, independently, methyl Or ethyl; and    R 6 is selected from the group consisting of methyl, ethyl, methoxy and ethoxy.    
     
     
         19 . The coating film of    claim 18   , wherein the metal oxide is titanium oxide.  
     
     
         20 . Titanium oxide treated with an organic metal compound represented by formula (1) or formula (2):  
                   
       wherein 
 M is —SiR 3 , —TiR 3  or Al:  
 R is a hydrogen atom or a C 1  to C 6  alkyl group;  
 R 1  and R 2  are each, independently, a C 1  to C 6  alkyl group;  
 R 3  is a C 1  to C 6  alkyl group which may be substituted with an alkoxy group or a C 1  to C 6  alkoxy group which may be substituted with an alkoxy group; or  
                 
 
 wherein  
 R 4  and R 5  are each, independently, methyl or ethyl; and  
 R 6  is selected from the group consisting of methyl, ethyl, methoxy and ethoxy.