Triarylamine derivative, electrophotographic photosensitive member, and method for producing electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-9964869-B2
Application number	US-201615345726-A
Country	US
Kind code	B2
Filing date	Nov 8, 2016
Priority date	Nov 9, 2015
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

A triarylamine derivative represented by general formula (1) below. In the general formula (1), R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 each represent, independently from one another, a hydrogen atom, an optionally substitute alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 14, R 3 represents an alkyl group having a carbon number of at least 1 and no greater than 4, X represents an alkylene group having a carbon number of at least 1 and no greater than 6 or an oxygen atom, and n represents an integer of 1 to 3.

First claim

What is claimed is:

1. A triarylamine derivative represented by general formula (1) below:

wherein in the general formula (1),
R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 each represent a hydrogen atom,
R 2 represents an alkyl group having a carbon number of at least 1 and no greater than 4,
R 3 represents an alkyl group having a carbon number of at least 1 and no greater than 4, the alkyl group being different from the alkyl group represented by R 2 ,
X represents an alkylene group having a carbon number of at least 1 and no greater than 6 or an oxygen atom, and
n represents 2.

2. The triarylamine derivative according to claim 1 , wherein
in the general formula (1), R 1 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each represent a hydrogen atom,
R 2 represents an alkyl group having a carbon number of at least 1 and no greater than 4,
R 3 represents an alkyl group having a carbon number of at least 1 and no greater than 4, the alkyl group being different from the alkyl group represented by R 2 ,
X represents an alkylene group having a carbon number of at least 1 and no greater than 3, and
n represents 2.

3. An electrophotographic photosensitive member comprising
a conductive substrate; and
a photosensitive layer containing a charge generating material and a hole transport material, wherein
the hole transport material is a triarylamine derivative represented by chemical formula (H-1), (H-3), or (H-5)

4. The electrophotographic photosensitive member according to claim 3 , wherein
a charge generating layer containing the charge generating material and a charge transport layer containing the hole transport material are included as the photosensitive layer, or a single-layer type photosensitive layer containing the charge generating material and the hole transport material is included as the photosensitive layer.

5. The electrophotographic photosensitive member according to claim 3 , wherein
the photosensitive layer includes: a charge generating layer containing the charge generating material; and a charge transport layer containing the hole transport material and a binder resin, and
the binder resin is a polycarbonate resin having a repeating unit represented by general formula (2) below:

where
R 21 and R 22 each represent, independently from each other, a hydrogen atom, an alkyl group, or an aryl group, and
R 23 and R 24 each represent, independently from each other, a hydrogen atom, an alkyl group, or an aryl group, or R 23 and R 24 bond to each other to represent a cycloalkylidene group.

6. The electrophotographic photosensitive member according to claim 5 , wherein
in the general formula (2),
R 21 and R 22 each represent, independently from each other, a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4, and
R 23 and R 24 each represent, independently from each other, a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4, or R 23 and R 24 bond to each other to represent a cycloalkylidene group having a carbon number of at least 5 and no greater than 7.

7. The electrophotographic photosensitive member according to claim 5 , wherein
in the general formula (2),
R 21 and R 22 each represent, independently from each other, a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4, and
R 23 and R 24 each represent, independently from each other, an alkyl group having a carbon number of at least 1 and no greater than 4, or R 23 and R 24 bond to each other to represent a cycloalkylidene group having a carbon number of at least 5 and no greater than 7.

8. The electrophotographic photosensitive member according to claim 3 , wherein
the photosensitive layer is a single-layer type photosensitive layer containing the charge generating material, the hole transport material, and an electron transport material, and
the electron transport material is a compound represented by general formula (8) below:

where
R 14 and R 15 each represent, independently from each other, a hydrogen atom, a cyano group, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkoxy group, an optionally substituted alkoxycarbonyl group, an optionally substituted aryl group, or an optionally substituted heterocyclic group.

9. The electrophotographic photosensitive member according to claim 3 , wherein
the charge generating material is titanyl phthalocyanine having a y-form crystal structure.

10. The electrophotographic photosensitive member according to claim 5 , wherein
the polycarbonate resin having a repeating unit represented by the general formula (2) is a resin having a repeating unit represented by chemical formula (Resin-1) or (Resin-4) below:

11. The electrophotographic photosensitive member according to claim 5 , wherein
the charge transport layer further contains silica particles surface-treated with hexamethyldisilazane,
the triarylamine derivative is represented by the chemical formula (H-1), (H-3), or (H-5), and
the polycarbonate resin having a repeating unit represented by the general formula (2) is a resin having a repeating unit represented by chemical formula (Resin-1) or (Resin-4) below:

Assignees

• Kyocera Document Solutions Inc

Inventors

• Okawa Kensuke
• Okada Hideki
• Azuma Jun
• Sugai Fumio
• Kojima Kensuke

Classifications

• G03G5/0618

  containing oxygen and nitrogen · CPC title

• G03G5/0672

  containing two or more methine or polymethine groups · CPC title

• C07C211/54 Primary

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

• G03G5/0609

  containing oxygen · CPC title

• G03G5/0525

  Coating methods · CPC title