Organic photoconductive members comprising dicyanomethylene substituted fluorene sensitizers

Abstract

Organic photoconductive systems which employ organic polymers containing aromatic or heterocyclic nuclei are combined with amounts of π acid type additives for the purpose of extending the spectral response to the visible portion of the spectrum. The sensitizing compounds are dicyanomethylene substituted fluorenes which are added in an amount expressed in moles of sensitizer per 100 moles of the organic photoconductor calculated as the monomer. The amount of sensitizer to be added may range from 0.1 to about 100 moles per 100 moles of organic photoconductor based on the molecular weight of the monomer.

What is claimed is: .[.1. A photoelectrostatic member comprising a conductive base support coated with a photoconductive film comprising an organic photoconductive polymer of the electron donor type and a sensitizer having the formula: ##STR2## wherein R 1 , R 2 , R 3  and R 4  are each substituents selected from the group consisting of nitro, cyano, halogen, trifluoromethyl, lower alkyl, substituted lower alkyls, lower alkoxy and 
     
        hydrogen..]. .[.2.  A photoelectrostatic member as claimed in claim 1 in which the amount of sensitizer present ranges from 0.1 mole to 100 moles per 100 moles of organic photoconductive donor..]. .[.3. A photoelectrostatic member as claimed in claim 1 in which the polymer is polyvinylcarbazole..]. .[.4. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-2,4,7-trinitrofluorene..]. .[.5. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 
     
     
        9-(dicyanomethylene)-2,7-dinitrofluorene..]. .[.6.  The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-2,4,5,7-tetranitrofluorene..]. .[.7. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-2,4,7-trichlorofluorene..]. .[.8. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-3-nitrofluorene..]. .[.9. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-2,4,7-tricyanofluorene..]. .[.10. The photoelectrostatic member as claimed in claim 1 in which the sensitizer is 9-(dicyanomethylene)-fluorene..]. .[.11. The photoelectrostatic member as claimed in claim 3 in which the molecular weight of the polyvinylcarbazole 
     
     
        polymer is in the range of 200,000-5,000,000..]. .[.12.  A photoelectrostatic member comprising a conductive base support coated with a photoconductive film comprising an organic photoconductor of the electron donor type and a sensitizer having the formula:.]. ##STR3## .[.wherein R 1 , R 2 , R 3  and R 4  are each substituents selected from the group consisting of nitro, cyano, halogen, trifluoromethyl, lower alkyl, substituted lower alkyls, lower alkoxy and 
     
     
        hydrogen..]. .[.13.  A photoelectrostatic member comprising a conductive base support coated with a photoconductive film comprising an organic photoconductor of the electron donor type sensitized with a 9-(dicyanomethylene)-polynitrofluorene compound..]. .[.14. A photoelectrostatic member comprising a conductive base support coated with a photoconductive film comprising an organic photoconductor of the electron donor type sensitized with a compound selected from the group consisting of.]. .[.a 9-(dicyanomethylene)-monoitrofluorene,.].   .[.a 9-(dicyanomethylene)-polynitrofluorene,.].   .[.a 9-(dicyanomethylene)-monocyanofluorene, and.].   
     
     
       .[.a 9-(dicyanomethylene)-polycyanofluorene..]. .[.15.  The method of making a reproduction comprising the steps of applying a sensitizing charge to an organic photoconductive medium of the electron donor type sensitized with a compound having the formula:.]. ##STR4## .[.wherein R 1 , R 2 , R 3  and R 4  are each substituents selected from the group consisting of nitro, cyano, halogen, trifluoromethyl, lower alkyl, substituted lower alkyls, lower alkoxy and hydrogen, said compound being present in an amount ranging from 10 moles to 35 moles per 100 moles of organic photoconductor taken as the weight of the monomer;.]. .[.exposing said charged member to a pattern of light and shadow comprising electromagnetic radiation in the visible range to produce a latent image thereon; and.].   .[.applying electroscopic powder to produce a material image corresponding   
     
     
        to said pattern of light and shadow..]. .Iadd. 16.  A photoelectrostatic member comprising a conductive base support coated with a photoconductive film comprising an organic photoconductive polymer of the electron donor type and incorporating therein one or more of the following sensitizers: 9-(dicyanomethylene)-2,4-dicyanofluorene   9-(dicyanomethylene)-2,4,7-tricyanofluorene   9-(dicyanomethylene)-2,4,5,7-tetracyanofluorene   9-(dicyanomethylene)-2,4-ditrifluoromethylfluorene   9-(dicyanomethylene)-2,4,7-tritrifluoromethylfluorene   9-(dicyanomethylene)-2,4,5,7-tetratrifluoromethylfluorene   9-(dicyanomethylene)-2,4-dimethylfluorene   9-(dicyanomethylene)-2,4,7-trimethylfluorene   9-(dicyanomethylene)-2,4,5,7-tetramethylfluorene   9-(dicyanomethylene)-2,4-dibutoxyfluorene   9-(dicyanomethylene)-2,4,7-tributoxyfluorene   9-(dicyanomethylene)-2,4,5,7-tetrabutoxyfluorene   9-(dicyanomethylene)-2,4-dichlorofluorene   9-(dicyanomethylene)-2,4,7-trichloro-fluorene   9-(dicyanomethylene)-2,4,5,7-tetrachloro-fluorene. .Iaddend..Iadd. 17. The method of making a reproduction comprising the steps of applying a sensitizing charge to an organic photoconductive medium of the electron donor type and having incorporated therein one or more of the following sensitizers:   9-(dicyanomethylene)-2,4-dicyanofluorene   9-(dicyanomethylene)-2,4,7-tricyanofluorene   9-(dicyanomethylene)-2,4,5,7-tetracyanofluorene   9-(dicyanomethylene)-2,4-ditrifluoromethylfluorene   9-(dicyanomethylene)-2,4,7-tritrifluoromethylfluorene   9-(dicyanomethylene)-2,4,5,7-tetratrifluoromethylfluorene   9-(dicyanomethylene)-2,4-dimethylfluorene   9-(dicyanomethylene)-2,4,7-trimethylfluorene   9-(dicyanomethylene)-2,4,5,7-tetramethylfluorene   9-(dicyanomethylene)-2,4-dibutoxyfluorene   9-(dicyanomethylene)-2,4,7-tributoxyfluorene   9-(dicyanomethylene)-2,4,5,7-tetrabutoxyfluorene   9-(dicyanomethylene)-2,4-dichlorofluorene   9-(dicyanomethylene)-2,4,7-trichloro-fluorene   9-(dicyanomethylene)-2,4,5,7-tetrachloro-fluorene..Iaddend.