Terphenyl compound, electrophotographic photosensitive member, and method for producing terphenyl compound

Patent metadata

Field	Value
Publication number	US-11067909-B2
Application number	US-201816632197-A
Country	US
Kind code	B2
Filing date	Jul 17, 2018
Priority date	Jul 21, 2017
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

A compound is represented by general formula (1). In general formula (1), R1 and R2 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R1 and the number of carbon atoms of the chemical group represented by R2 is 2. R3 and R4 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R3 and the number of carbon atoms of the chemical group represented by R1 is 2. A photosensitive layer of an electrophotographic photosensitive member contains at least a charge generating material, a hole transport material, and a binder resin. The hole transport material includes a compound represented by general formula (1)

First claim

The invention claimed is:

1. An electrophotographic photosensitive member comprising a conductive substrate and a photosensitive layer, wherein
the photosensitive layer contains at least a charge generating material, a hole transport material, and a binder resin,
the hole transport material includes a compound represented by general formula (1) shown below,
the binder resin includes a polyarylate resin,
the polyarylate resin is
a polyarylate resin including repeating units represented by chemical formula (10-2), chemical formula (11-X1), and chemical formula (11-X2), or
a polyarylate resin including repeating units represented by chemical formula (10-1), chemical formula (12-1), and chemical formula (11-X3), and

the photosensitive layer includes a charge generating layer containing the charge generating material and a charge transport layer containing the hole transport material and the binder resin, or the photosensitive layer is a single-layer photosensitive layer containing the charge generating material, the hole transport material, and the binder resin,

wherein in the general formula (1),
R 1 and R 2 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R 1 and the number of carbon atoms of the chemical group represented by R 2 is 2, and
R 3 and R 4 each represent, independently of one another, a hydrogen atom, a methyl group, or an ethyl group, and a sum of the number of carbon atoms of the chemical group represented by R 3 and the number of carbon atoms of the chemical group represented by R 4 is 2

2. The electrophotographic photosensitive member according to claim 1 , wherein
a ratio of mass of the hole transport material to mass of the binder resin is at least 0.50.

3. The electrophotographic photosensitive member according to claim 1 , wherein
the polyarylate resin is
the polyarylate resin including repeating units represented by chemical formula (10-2), the chemical formula (11-X1), and the chemical formula (11- X2).

4. The electrophotographic photosensitive member according to claim 1 , wherein
the polyarylate resin is the polyarylate resin including repeating units represented by the chemical formula (10-1), the chemical formula (12-1), and the chemical formula (11-X3).

5. The electrophotographic photosensitive member according to claim 1 , wherein
the photosensitive layer includes the charge generating layer and the charge transport layer,
the charge transport layer further contains an electron acceptor compound, and
a ratio of mass of the electron acceptor compound to mass of the hole transport material is at least 0.01 and no greater than 0.50.

6. The electrophotographic photosensitive member according to claim 5 , wherein
the electron acceptor compound includes a compound represented by general formula (20), (21), (22), (23), or (24),

where in the general formula (20), Q 1 , Q 2 , Q 3 , and Q 4 each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 6, an alkoxy group having a carbon number of at least 1 and no greater than 6, a cycloalkyl group having a carbon number of at least 5 and no greater than 7, or an aryl group having a carbon number of at least 6 and no greater than 14,
in the general formula (21), Q 11 and Q 12 each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 6, an alkoxy group having a carbon number of at least 1 and no greater than 6, a cycloalkyl group having a carbon number of at least 5 and no greater than 7, or an aryl group having a carbon number of at least 6 and no greater than 14,
in the general formula (22), Q 21 and Q 22 each represent, independently of one another, an aryl group having a carbon number of at least 6 and no greater than 14 and optionally having an alkyl group having a carbon number of at least 1 and no greater than 6 or an alkoxy group having a carbon number of at least 1 and no greater than 6,
in the general formula (23), Q 31 represents an alkoxycarbonyl group having a carbon number of at least 2 and no greater than 7, and
in the general formula (24), Q 41 and Q 42 each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 6, and Q 43 represents a halogen atom.

7. The electrophotographic photosensitive member according to claim 5 , wherein
the electron acceptor compound includes a compound represented by chemical formula (20-E1), (20-E2), (21-E3), (22-E4), (23-E5), or (24-E6)

8. The electrophotographic photosensitive member according to claim 1 , wherein
the photosensitive layer is the single-layer photosensitive layer,
the photosensitive layer further contains an electron transport material, and
a ratio of mass of the electron transport material to mass of the hole transport material is at least 0.01 and no greater than 1.50.

9. The electrophotographic photosensitive member according to claim 1 , wherein the general formula (1) is represented by chemical formula (1-1), (1-2), or (1-3)

Assignees

• Kyocera Document Solutions Inc

Inventors

• Azuma Jun
• Kojima Kensuke
• Shimizu Tomofumi
• Okada Hideki

Classifications

• C07C211/54

  having amino groups bound to two or three six-membered aromatic rings · CPC title

• G03G5/0618

  containing oxygen and nitrogen · CPC title

• G03G5/0546

  Polymers comprising at least one carboxyl radical, e.g. polyacrylic acid, polycrotonic acid, polymaleic acid; Derivatives thereof, e.g. their esters, salts, anhydrides, nitriles, amides · CPC title

• G03G5/0609

  containing oxygen · CPC title

• C07C209/06

  by substitution of halogen atoms · CPC title