Electrophotographic organophotoreceptors with novel charge transport compounds

An organic photoreceptor that includes:

• (a) a charge transport compound having the formula
• (R—Q)n-Y Formula I
• wherein R is selected from the group consisting of julolidine ring groups, carbazole ring groups, and triarylmethane ring groups;
• Q comprises an aromatic hydrazone linking group;
• Y comprises a bridging group between R—Q— groups;
• n is an integer between 2 and 6, inclusive;
• (b) a charge generating compound;
• and
• (c) an electrically conductive substrate.

An organic photoreceptor comprising:

• (a) a charge transport compound having the formula
• where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, or an aryl group;
• R2 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, an aryl group, or a —NR1R5 group where R4 and R5 are, independently, hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, a cycloalkyl group, an aryl group, or R4 and R5 combine with the nitrogen atom to form a ring;
• R3 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, or an aryl group;
• X is a linking group having the formula —(CH2)m—, branched or linear, where m is an integer between 0 and 20, inclusive, and one or more of the methylene groups is optionally replaced by an oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR6 group, a CHR7 group, or a CR8R9 group where R6, R7, R8, and R9 are, independently, H, an alkyl group, or aryl group;
• and
• Y is a bond, carbon atom, nitrogen atom, oxygen atom, sulfur atom, a branched or linear —(CH2)p— group where p is an integer between 0 and 10, an aryl group, a cycloalkyl group, a cyclosiloxyl group, a heterocyclic group, or a CR10 group where R10 is hydrogen atom, an alkyl group, or aryl group;
• (b) a charge generating compound;
• and
• (c) an electrically conductive substrate.

An electrophotographic imaging apparatus comprising:

• (a) a plurality of support rollers, at least one having a diameter no greater than about 40 mm;
• and
• (b) an organic photoreceptor in the form of a flexible belt threaded around said support rollers, said organic photoreceptor comprising:
• (i) a charge transport compound having the formula
• where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, or an aryl group;
• R2 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, an aryl group, or a —NR4R5 group where R4 and R5 are, independently, hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, a cycloalkyl group, an aryl group, or R4 and R5 combine with the nitrogen atom to form a ring;
• R3 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, or an aryl group;
• X is a linking group having the formula —(CH2)m—, branched or linear, where m is an integer between 0 and 20, inclusive, and one or more of the methylene groups is optionally replaced by an oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR6 group, a CHR7 group, or a CR8R9 group where R6, R7, R8, and R9 are, independently, H, an alkyl group, or aryl group;
• and
• Y is a bond, carbon atom, nitrogen atom, oxygen atom, sulfur atom, a branched or linear —(CH2)p— group where p is an integer between 0 and 10, an aryl group, a cycloalkyl group, a cyclosiloxyl group, a heterocyclic group, or a CR10 group where R10 is hydrogen atom, an alkyl group, or aryl group;
• (ii) a charge generating compound;
• and
• (iii) an electrically conductive substrate.

An electrophotographic imaging process comprising:

• (a) applying an electrical charge to a surface of an organic photoreceptor comprising:
• (i) a charge transport compound having the formula
• where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, or an aryl group;
• R2 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, an aryl group, or a —NR4R5 group where R4 and R5 are, independently, hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, a cycloalkyl group, an aryl group, or R4 and R5 combine with the nitrogen atom to form a ring;
• R3 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, or an aryl group;
• X is a linking group having the formula —(CH2)m—, branched or linear, where m is an integer between 0 and 20, inclusive, and one or more of the methylene groups is optionally replaced by an oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR6 group, a CR7 group, or a CR8R9 group where R6 , R7, R8, and R9 are, independently, H, an alkyl group, or aryl group;
• and
• Y is a bond, carbon atom, nitrogen atom, oxygen atom, sulfur atom, a branched or linear —(CH2)p— group where p is an integer between 0 and 10, an aryl group, a cycloalkyl group, a cyclosiloxyl group, a heterocyclic group, or a CR10 group where R10 is hydrogen atom, an alkyl group, or aryl group;
• (ii) a charge generating compound;
• and
• (iii) an electrically conductive substrate;
• (b) imagewise exposing said surface of said organic photoreceptor 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.

A charge transport compound having the formula

• where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, or an aryl group;
• R2 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, an aryl group, or a —NR4R5 group where R4 and R5 are, independently, hydrogen, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, a cycloalkyl group, an aryl group, or R4 and R5 combine with the nitrogen atom to form a ring;
• R3 is hydrogen, a halogen, hydroxy group, thiol group, an alkoxy group, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, an ether group, a cycloalkyl group, or an aryl group;
• X is a linking group having the formula —(CH2)m—, branched or linear, where m is an integer between 0 and 20, inclusive, and one or more of the methylene groups is optionally replaced by an oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR6 group, a CHR7 group, or a CR8R9 group where R6, R7, R8, and R9 are, independently, H, an alkyl group, or aryl group;
• and
• Y is a bond, carbon atom, nitrogen atom, oxygen atom, sulfur atom, a branched or linear —(CH2)p— group where p is an integer between 0 and 10, an aryl group, a cycloalkyl group, a cyclosiloxyl group, a heterocyclic group, or a CR10 group where R10 is hydrogen atom, an alkyl group, or aryl group.

A charge transport compound having the formula:

• R1, R2, and R3 are, independently, a branched or linear alkyl group, a branched or linear unsaturated hydrocarbon group, a cycloalkyl group, a heterocyclic group, or an aryl group;
• R4, R5, and R6 are, independently, triarylamine, diaryl alkylamine, dialkyl arylamine, a carbocyclic ring, or a heterocyclic ring group;
• and
• X is a linking group having the formula
• where m, n, and o are independently an integer between 0 and 50, inclusive;
• one or more of the methylene groups is optionally replaced by a bond, an oxygen atom, a sulfur atom, a carbonyl group, an urethane group, an urea group, an ester group, an aryl group, a heterocyclic group, a NR5 group, a CHR6 group, or a CR7R8 group where R5, R6, R7, and R8 are, independently, H, an alkyl group, or an aryl group;
• and the C—H group is optionally replaced by a nitrogen atom, a boron atom, a metal atom, and a CR9 group where R9 is an alkyl group or an aryl group.