Polycarbonate resin and electrophotographic photosensitive member using same

Abstract

Provided are a polycarbonate resin which can solve problems present in an electrophotographic photoreceptor and an electrophotographic photoreceptor in which the above polycarbonate resin is used and which is improved in a cleaning property, a lubricity and an abrasion resistance. The polycarbonate resin comprises a repetitive unit represented by the following Formula (1), and the electrophotographic photoreceptor in which a photosensitive layer is provided on a conductive substrate contains the above polycarbonate resin in the above photosensitive layer. In the following Formula (1), R represents an alkyl group having 1 to 3 carbon atoms; n1 is an integer of 2 to 4; and n2 is an integer of 1 to 200.

1. A polycarbonate resin comprising a repetitive unit represented by the following Formula (1) and a repetitive unit represented by the following Formula (2): 
       
         
           
           
               
               
           
         
         (wherein R represents an alkyl group having 1 to 3 carbon atoms; n1 is an integer of 2 to 4; and n2 is an integer of 1 to 200), 
       
       
         
           
           
               
               
           
         
         (wherein Ar represents a divalent aromatic group which comprises at least one of groups represented by the following Formula (3): 
       
       
         
           
           
               
               
           
         
         [wherein R 1  and R 2  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms; and X represents a group selected from a single bond, —O—, —S—, —SO—, —SO 2 —, —CO—, —CR 3 R 4 — (wherein R 3  and R 4  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms), a substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms, a substituted or unsubstituted α,ω-alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted 9,9-fluorenylidene group, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a divalent group derived from natural terpenes represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 5  to R 7  represent the same groups as those represented by R 1  and R 2 ) and an alkylidenearylenealkylidene group having 8 to 16 carbon atoms represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 8  to R 11  represent the same groups as those represented by R 1  and R 2 )], and 
       
       wherein the group represented by formula (3) is
 (i) the group represented by formula (3) is a combination of the group in which X is a single bond and the group in which X is a group other than a single bond, or 
 (ii) the group represented by formula (3) is a combination of the group in which all X are a single bond and n2 in formula (1) is an integer of 39 to 200. 
 
     
     
       2. The polycarbonate resin as described in  claim 1 , wherein the group represented by Formula (3) is a combination of the group in which X is a single bond and the group in which X is a group other than a single bond. 
     
     
       3. The polycarbonate resin as described in  claim 1 , wherein n2 is an integer of 10 to 100. 
     
     
       4. An electrophotographic photoreceptor in which a photosensitive layer is provided on a conductive substrate, wherein
 (1) the photosensitive layer is comprised of a laminate comprising at least one charge generating layer and at least one charge transporting layer comprising a charge transporting material and a polycarbonate resin, wherein the polycarbonate resin comprises a repetitive unit represented by the following formula (1): 
 
       
         
           
           
               
               
           
         
         (wherein R represents an alkyl group having 1 to 3 carbon atoms; n1 is an integer of 2 to 4; and n2 is an integer of 1 to 200); 
         wherein the ratio of charge transporting material to polycarbonate resin is 20:80 to 80:20 by mass; or 
         (2) the photosensitive layer is comprised of a single layer comprising at least one polycarbonate resin represented by said formula (1), at least one charge generating material and at least one charge transporting material; 
         wherein the ratio of the at least one charge transporting material to the at least one polycarbonate resin is 5:95 to 80:20 by mass. 
       
     
     
       5. The electrophotographic photoreceptor as described in  claim 4 , wherein the polycarbonate resin contained in the photosensitive layer further comprises a repetitive unit represented by the following Formula (2): 
       
         
           
           
               
               
           
         
         (wherein Ar represents a divalent aromatic group). 
       
     
     
       6. The electrophotographic photoreceptor as described in  claim 5 , wherein Ar in Formula (2) comprises at least one of groups represented by the following Formula (3) 
       
         
           
           
               
               
           
         
         [wherein R 1  and R 2  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms; and X represents a group selected from a single bond, —O—, —S—, —SO—, —SO 2 —, —CO—, —CR 3 R 4 — (wherein R 3  and R 4  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms), a substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms, a substituted or unsubstituted α,ω-alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted 9,9-fluorenylidene group, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a divalent group derived from natural terpenes represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 5  to R 7  represent the same groups as those represented by R 1  and R 2 ) and an alkylidenearylenealkylidene group having 8 to 16 carbon atoms represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 8  to R 11  represent the same groups as those represented by R 1  and R 2 )]. 
       
     
     
       7. The electrophotographic photoreceptor as described in  claim 6 , wherein X in Formula (3) is a group selected from —CR 3 R 4 —, a single bond, a substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms and a substituted or unsubstituted 9,9-fluorenylidene group. 
     
     
       8. The electrophotographic photoreceptor as described in  claim 6 , wherein X in Formula (3) is —CR 3 R 4 —, and a proportion of the repetitive unit represented by Formula (1) is 0.01 to 3.9 mass % based on the whole part of the polycarbonate resin. 
     
     
       9. The electrophotographic photoreceptor as described in  claim 6 , wherein the group represented by Formula (3) is (a) a combination of the group in which X is a single bond and the group in which X is a group other than a single bond, (b) a combination of the group in which X is the substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms and the group in which X is a group other than the substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms, (c) a combination of the group in which X is the substituted or unsubstituted 9,9-fluorenylidene group and the group in which X is a group other than the substituted or unsubstituted 9,9-fluorenylidene group, (d) a combination of the group in which X is the alkylidenearylenealkylidene group having 8 to 16 carbon atoms and the group in which X is a group other than the alkylidenearylenealkylidene group having 8 to 16 carbon atoms, (e) a combination of the group in which X is —SO— and the group in which X is a group other than —SO—, (f) a combination of the group in which X is —O— and the group in which X is a group other than —O— or (g) a combination of the group in which X is —CO— and the group in which X is a group other than —CO—. 
     
     
       10. The electrophotographic photoreceptor as described in  claim 4 , wherein the polycarbonate resin is used as a binder resin in the charge transporting layer. 
     
     
       11. A polycarbonate resin comprising a repetitive unit represented by the following Formula (1) and a repetitive unit represented by the following Formula (2): 
       
         
           
           
               
               
           
         
         (wherein R represents an alkyl group having 1 to 3 carbon atoms; n1 is an integer of 2 to 4; and n2 is an integer of 1 to 200) 
       
       
         
           
           
               
               
           
         
         (wherein Ar represents a divalent aromatic group, and comprises at least one of groups represented by the following formula (3)) 
       
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms; X represents a group selected from a single bond, —O—, —S—, —SO—, —SO 2 —, —CO—, —CR 3 R 4 — (wherein R 3  and R 4  each represent independently a group selected from a hydrogen atom, a trifluoromethyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and a substituted or unsubstituted aryl group having 6 to 12 carbon atoms), a substituted or unsubstituted cycloalkylidene group having 5 to 11 carbon atoms, a substituted or unsubstituted α, ω-alkylene group having 2 to 12 carbon atoms, a substituted or unsubstituted 9,9-fluorenylidene group, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a divalent group derived from natural terpenes represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 5  to R 7  represent the same groups as those represented by R 1  and R 2 ) and an alkylidenearylenealkylidene group having 8 to 16 carbon atoms represented by the following formula: 
       
       
         
           
           
               
               
           
         
         (wherein R 8  to R 11  represent the same groups as those represented by R 1  and R 2 ; 
         and the group represented by Formula (3) is a combination of a group in which X is a substituted or unsubstituted 9,9-fluorenylidene group and a group in which X is a group other than a substituted or unsubstituted 9,9-fluorenylidene group. 
       
     
     
       12. The polycarbonate resin as described in claim 1, wherein R 1  and R 2  each represent independently a group selected from a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms. 
     
     
       13. The polycarbonate resin as described in claim 1, wherein at least one of R 1  and R 2  represents a hydrogen atom. 
     
     
       14. The polycarbonate resin as described in claim 1, wherein both R 1  and R 2  represent a hydrogen atom. 
     
     
       15. The electrophotographic photoreceptor as described in claim 6, wherein R 1  and R 2  each represent independently a group selected from a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms. 
     
     
       16. The electrophotographic photoreceptor as described in claim 6, wherein at least one of R 1  and R 2  represents a hydrogen atom. 
     
     
       17. The electrophotographic photoreceptor as described in claim 6, wherein both R 1  and R 2  represent a hydrogen atom. 
     
     
       18. The polycarbonate resin as described in claim 11, wherein R 1  and R 2  each represent independently a group selected from a trifluoromethyl group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 6 carbon atoms and an aryloxy group having 6 to 12 carbon atoms. 
     
     
       19. The polycarbonate resin as described in claim 11, wherein at least one of R 1  and R 2  represents a hydrogen atom. 
     
     
       20. The polycarbonate resin as described in claim 11, wherein both R 1  and R 2  represent a hydrogen atom. 
     
     
       21. The polycarbonate resin as described in claim 1, wherein n2 is an integer of 100 to 200.