Aromatic heterocyclic-based charge transport materials having two amino groups

An electrophotographic imaging apparatus comprising:

• (a) a light imaging component;
• and
• (b) an organophotoreceptor oriented to receive light from the light imaging component, the organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising:
• (i) a charge transport material having the formula
• where Y comprises an aromatic heterocyclic group;
• X is a bond or a linking group;
• E comprises a reactive ring group, a reactive functional group, or an ethylenically unsaturated group;
• and
• R1, R2, R3, and R4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group;
• and
• (ii) a charge generating compound.

An electrophotographic imaging process comprising;

• (a) applying an electrical charge to a surface of an organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising
• (i) a charge transport material having the formula
• where Y comprises an aromatic heterocyclic group;
• X is a bond or a linking group;
• E comprises a reactive ring group, a reactive functional group, or an ethylenically unsaturated group;
• and
• R1, R2, R3, and R4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group;
• and
• (ii) a charge generating compound.
• (b) imagewise exposing the surface of the organophotoreceptor to radiation to dissipate charge in selected areas and thereby form a pattern of charged and uncharged areas on the surface;
• (c) contacting the surface with a toner to create a toned image;
• and
• (d) transferring the toned image to substrate.

A charge transport material having the formula

• where Y comprises an aromatic heterocyclic group;
• X is a bond or a linking group;
• E comprises a reactive ring group, a reactive functional group, or an ethylenically unsaturated group;
• and
• R1, R2, R3, and R4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group.

A method of preparing a bridged charge transport material by reacting a bridging compound having the formula HQ1-Z-Q2H with at least a reactive ring compound having the following formula:

• where Y comprises an aromatic heterocyclic group;
• X and Z comprise, each independently, a bond or a linking group;
• E comprises a reactive ring group;
• Q1 and Q2 are each independently, O, S, and NR;
• and
• R, R1, R2, R3, and R4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group.

A method of preparing a bridged charge transport material by reacting a reactive functional compound having the following formula:

• with a reactive ring compound having the following formula:
• where Y and Y′, each independently, comprise an aromatic heterocyclic group;
• X and X′ comprise, each independently, a bond or a linking group;
• E comprises a reactive ring group;
• E′ comprises a reactive functional group;
• R1′, R2′, R3′, R4′, R1, R2, R3, and R4 comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group.

A bridged charge transport material having the following formula:

• where Y and Y′, each independently, comprise an aromatic heterocyclic group;
• X1 is a first linking group;
• and
• R1, R2, R3, R4, R1′, R2′, R3′, and R4′ comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group.

An organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising:

• (b) a bridged charge transport material having the formula
• where Y and Y′, each independently, comprise an aromatic heterocyclic group;
• X1 is a first linking group;
• and
• R1, R2, R3, R4, R1′, R2′, R3′, and R4′ comprise, each independently, H, an alkyl group, an acyl group, an ether group, an alkenyl group, an alkynyl group, a heterocyclic group, an aromatic group, or a part of a ring group;
• and
• (b) a charge generating compound.