Electrophotographic organophotoreceptors with novel charge transport materials

An organophotoreceptor comprising:

• (a) a charge transport material having a formula selected from the group consisting of:
• 10
• A) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is an alkylsulfonylphenyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• B) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is pyrrolyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• C) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is benzotriazolyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• D) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is sulfolanyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• E) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is a pyrazolyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• F) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is tetrazolyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• G) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is stilbenyl or one of its derivatives;
• 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• H) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is (9H-fluoren-9-ylidene)benzyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• and
• I) where n is an integer between 2 and 6, inclusive;
• R1 is hydrogen, an alkyl group, or an aryl group;
• R2 is naphthyl 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 oxygen atom, a carbonyl group, urethane, urea, an ester group, a —NR3 group, a CHR4 group, or a CR5R6 group where R3, R4, R5, and R6 are, independently, H, an alkyl group, or an 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 CR7 group where R7 is hydrogen atom, an alkyl group, or an aryl group;
• (b) a charge generating compound;
• and
• (c) an electrically conductive substrate.

An electrophotographic imaging apparatus comprising:

• (a) a plurality of support rollers;
• and
• (b) an organophotoreceptor in the form of a flexible belt threaded around said support rollers, said organophotoreceptor comprising:
• (i) a charge transport material comprising a fluorenone hydrazones having a) least two fluorenone alkylsulfonylphenylhydrazone groups, b) at least two fluorenone pyrrolylhydrazone groups, c) at least two fluorenone benzotriazolylhydrazone groups, d) at least two fluorenone sulfolanylhydrazone, groups, e) at least two fluorenone pyrazolylhydrazone groups, f) at least two fluorenone naphthylhydrazone groups, g) at least two fluorenone tetrazolylhydrazone groups, h) at least two fluorenone stilbenylhydrazone groups, and i) at least two fluorenone (9H-fluoren-9-ylidene)benzylhydrazone groups;
• (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 organophotoreceptor comprising:
• (i) a charge transport material comprising a fluorenone hydrazones having a) least two fluorenone alkylsulfonylphenylhydrazone groups, b) at least two fluorenone pyrrolylhydrazone groups, c) at least two fluorenone benzotriazolylhydrazone groups, d) at least two fluorenone sulfolanylhydrazone groups, e) at least two fluorenone pyrazolylhydrazone groups, f) at least two fluorenone naphthylhydrazone groups, g) at least two fluorenone tetrazolylhydrazone groups, h) at least two fluorenone stilbenylhydrazone groups, and i) at least two fluorenone (9H-fluoren-9-ylidene)benzylhydrazone groups;
• (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.