Poly(azine)-based charge transport materials

Abstract

The present invention provides organophotoreceptors comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula; where X1 and X2 are, each independently, a linking group; Ar comprises an aromatic group; R1, R2, and R3 comprise, each independently, H, an alkyl group, an alkenyl group, an alkynyl group, an aromatic group, or a heterocyclic group; and n is a distribution of integers between 1 and 100,000 with an average value of greater than one; and (b) a charge generating compound. Corresponding electrophotographic apparatuses, imaging methods (processes), and methods of forming the charge transport material are described.

Description

technical field

[0001] The present invention relates to an organic photoreceptor suitable for electrophotography, and more particularly, to an organic photoreceptor having a charge transport material comprising a polymer having repeating aromatic azine groups. Furthermore, the present invention also relates to a process for preparing charge transport materials comprising polymers having repeating aromatic azine groups. Background technique

[0002] In electrophotography, an organic photoreceptor in the form of a plate, a disk, a sheet, a belt or a drum has an electrically insulating photoconductive element (photoconductive element) on a conductive substrate, and the imaging steps of the organic photoreceptor are: first The surface of the photoconductive layer is uniformly electrostatically charged, and then the charged surface is exposed to a light pattern. Exposure selectively dissipates charge in illuminated areas where light reaches the surface, thereby forming a pattern...

Examples

Embodiment 1-

[0116] Example 1- Synthesis and Characterization of Charge Transport Materials

[0117] This example describes the synthesis and characterization of compound (1). Characterization includes chemical characterization of the compound. And the electrostatic properties of materials formed from said compounds, such as mobility and ionization potential, are described in the subsequent examples.

[0118] Bis(4,4′-diethylamino)benzophenone hydrazone

[0119] Bis(4,4'-diethylamino)benzophenone (108.1 g, 0.335 mol, obtained from Aldrich), hydrazine monohydrate (98%, 244 ml, 5 mol, obtained from Aldrich) in 250 ml 2-propanol ) and 10 ml of concentrated hydrochloric acid (obtained from Aldrich) were added to a 1000 ml three-necked round bottom flask equipped with a reflux condenser and a mechanical stirrer. With vigorous stirring, the solution was refluxed for about 6 hours until bis(4,4'-diethylamino)benzophenone disappeared. The solution was left to stand overnight. Crystals for...

Embodiment 2-

[0126] Example 2- Measuring Charge Mobility

[0127] This example describes the measurement of the charge mobility and ionization potential of charge transport materials, in particular the charge mobility and ionization potential of compound (1) described above.

[0128] Sample 1

[0129] A mixture of 0.1 g of compound (1) and 0.1 g of polycarbonate Z was dissolved in 2 ml of tetrahydrofuran. The solution was applied to a polyester film with a conductive aluminum layer by means of a dip roller. When the coating was dried at 80° C. for 1 hour, a 10 μm thick transparent layer was formed. The hole mobility of the samples was measured, and the results are listed in Table 1.

[0130] Measuring Mobility

[0131] Each sample was positively corona charged until the surface potential was U and irradiated with 2 ns long nitrogen laser pulses. Hole mobility μ was measured according to Kalade et al., "Investigation of charge carrier transferin electrophotographic layers of chal...

Embodiment 3

[0135] Example 3 - Measurement of ionization potential

[0136] This example describes the measurement of the ionization potential of the charge transport material described in Example 1.

[0137] To measure the ionization potential, a solution of 2 mg of charge transport material in 0.2 ml of tetrahydrofuran was placed at 20 cm 2 A thin layer of charge transport material about 0.5 μm thick is coated on the surface of the substrate. The substrate was an aluminized polyester film coated with a 0.4 μm thick sublayer of methylcellulose.

[0138] According to the method described by Grigalevicius et al. in "3,6-Di(N-diphenylamino)-9-phenylcarbazole and its methyl-substituted derivative as novel hole-transporting amorphous molecular materials" Synthetic Metals 128 (2002), Pp.127-131 The ionization potential was measured, which document is incorporated herein by reference. Specifically, each sample was illuminated with monochromatic light from a quartz monochromator with a deuter...

technical field

[0001] The present invention relates to an organic photoreceptor suitable for electrophotography, and more particularly, to an organic photoreceptor having a charge transport material comprising a polymer having repeating aromatic azine groups. Furthermore, the present invention also relates to a process for preparing charge transport materials comprising polymers having repeating aromatic azine groups. Background technique

[0002] In electrophotography, an organic photoreceptor in the form of a plate, a disk, a sheet, a belt or a drum has an electrically insulating photoconductive element (photoconductive element) on a conductive substrate, and the imaging steps of the organic photoreceptor are: first The surface of the photoconductive layer is uniformly electrostatically charged, and then the charged surface is exposed to a light pattern. Exposure selectively dissipates charge in illuminated areas where light reaches the surface, thereby forming a pattern...

Examples

Embodiment 1-

[0116] Example 1- Synthesis and Characterization of Charge Transport Materials

[0117] This example describes the synthesis and characterization of compound (1). Characterization includes chemical characterization of the compound. And the electrostatic properties of materials formed from said compounds, such as mobility and ionization potential, are described in the subsequent examples.

[0118] Bis(4,4′-diethylamino)benzophenone hydrazone

[0119] Bis(4,4'-diethylamino)benzophenone (108.1 g, 0.335 mol, obtained from Aldrich), hydrazine monohydrate (98%, 244 ml, 5 mol, obtained from Aldrich) in 250 ml 2-propanol ) and 10 ml of concentrated hydrochloric acid (obtained from Aldrich) were added to a 1000 ml three-necked round bottom flask equipped with a reflux condenser and a mechanical stirrer. With vigorous stirring, the solution was refluxed for about 6 hours until bis(4,4'-diethylamino)benzophenone disappeared. The solution was left to stand overnight. Crystals for...

Embodiment 2-

[0126] Example 2- Measuring Charge Mobility

[0127] This example describes the measurement of the charge mobility and ionization potential of charge transport materials, in particular the charge mobility and ionization potential of compound (1) described above.

[0128] Sample 1

[0129] A mixture of 0.1 g of compound (1) and 0.1 g of polycarbonate Z was dissolved in 2 ml of tetrahydrofuran. The solution was applied to a polyester film with a conductive aluminum layer by means of a dip roller. When the coating was dried at 80° C. for 1 hour, a 10 μm thick transparent layer was formed. The hole mobility of the samples was measured, and the results are listed in Table 1.

[0130] Measuring Mobility

[0131] Each sample was positively corona charged until the surface potential was U and irradiated with 2 ns long nitrogen laser pulses. Hole mobility μ was measured according to Kalade et al., "Investigation of charge carrier transferin electrophotographic layers of chal...

Embodiment 3

[0135] Example 3 - Measurement of ionization potential

[0136] This example describes the measurement of the ionization potential of the charge transport material described in Example 1.

[0137] To measure the ionization potential, a solution of 2 mg of charge transport material in 0.2 ml of tetrahydrofuran was placed at 20 cm 2 A thin layer of charge transport material about 0.5 μm thick is coated on the surface of the substrate. The substrate was an aluminized polyester film coated with a 0.4 μm thick sublayer of methylcellulose.

[0138] According to the method described by Grigalevicius et al. in "3,6-Di(N-diphenylamino)-9-phenylcarbazole and its methyl-substituted derivative as novel hole-transporting amorphous molecular materials" Synthetic Metals 128 (2002), Pp.127-131 The ionization potential was measured, which document is incorporated herein by reference. Specifically, each sample was illuminated with monochromatic light from a quartz monochromator with a deuter...

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