Polyarylate resin and electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-12339618-B2
Application number	US-202217705063-A
Country	US
Kind code	B2
Filing date	Mar 25, 2022
Priority date	Apr 7, 2021
Publication date	Jun 24, 2025
Grant date	Jun 24, 2025

Abstract

A polyarylate resin includes repeating units represented by formulas (1), (2), (3), and (4).

A third percentage is greater than 0% and less than 50%. The third percentage is a percentage of the number of repeats of the repeating unit represented by formula (3) relative to the total of the number of repeats of the repeating unit represented by formula (1) and the number of repeats of the repeating unit represented by formula (3). A fourth percentage is at least 35% and less than 70%. The fourth percentage is a percentage of the number of repeats of the repeating unit represented by formula (4) relative to the total of the number of repeats of the repeating unit represented by formula (2) and the number of repeats of the repeating unit represented by formula (4).

First claim

What is claimed is:

1. A polyarylate resin comprising
repeating units represented by formulas (1), (2), (3), and (4), wherein
a third percentage is greater than 0% and less than 50%, the third percentage being a percentage of the number of repeats of the repeating unit represented by the formula (3) relative to a total of the number of repeats of the repeating unit represented by the formula (1) and the number of repeats of the repeating unit represented by the formula (3), and
a fourth percentage is at least 35% and less than 70%, the fourth percentage being a percentage of the number of repeats of the repeating unit represented by the formula (4) relative to a total of the number of repeats of the repeating unit represented by the formula (2) and the number of repeats of the repeating unit represented by the formula (4),

where in the formula (1),
R 1 and R 2 each represent a methyl group and X represents a divalent group represented by formula (X1), or
R 1 and R 2 each represent a hydrogen atom and X represents a divalent group represented by formula (X2),

where in the formulas (X1) and (X2), * represents a bond, and

wherein
a first percentage differs from a second percentage and the fourth percentage,
the third percentage differs from the second percentage and the fourth percentage,
the first percentage is a percentage of the number of repeats of the repeating unit represented by the formula (1) relative to the total of the number of repeats of the repeating unit represented by the formula (1) and the number of repeats of the repeating unit represented by the formula (3), and
the second percentage is a percentage of the number of repeats of the repeating unit represented by the formula (2) relative to the total of the number of repeats of the repeating unit represented by the formula (2) and the number of repeats of the repeating unit represented by the formula (4).

2. The polyarylate resin according to claim 1 , wherein
in the formula (1), R 1 and R 2 each represent a methyl group and X represents a divalent group represented by the formula (X1).

3. The polyarylate resin according to claim 1 , wherein
in the formula (1), R 1 and R 2 each represent a methyl group and X represents a divalent group represented by the formula (X1), and
the fourth percentage is at least 40% and less than 70%.

4. The polyarylate resin according to claim 1 , wherein
in the formula (1), R 1 and R 2 each represent a methyl group and X represents a divalent group represented by the formula (X1), and
the third percentage is at least 30% and less than 50%.

5. The polyarylate resin according to claim 1 , wherein
in the formula (1), R 1 and R 2 each represent a methyl group and X represents a divalent group represented by the formula (X1), and
the polyarylate resin further comprises an end group having a halogen atom.

6. The polyarylate resin according to claim 1 , wherein
in the formula (1), R 1 and R 2 each represent a hydrogen atom and X represents a divalent group represented by the formula (X2), and
the fourth percentage is at least 35% and no greater than 45%.

7. The polyarylate resin according to claim 1 , wherein
the third percentage is greater than 30% and less than 50%.

8. The polyarylate resin according to claim 1 , wherein
the polyarylate resin does not comprise a repeating unit represented by formula (5)

9. An electrophotographic photosensitive member comprising:
a conductive substrate; and
a photosensitive layer, wherein
the photosensitive layer contains a charge generating material, a hole transport material, and a binder resin, and
the binder resin includes the polyarylate resin according to claim 1 .

10. The electrophotographic photosensitive member according to claim 9 , wherein
the hole transport material includes a compound represented by formula (19), (20), (21), or (22),

in the formula (19), R 16 , R 17 , R 18 , and R 19 each represent, independently of one another, an alkyl group with a carbon number of at least 1 and no greater than 6 or an alkoxy group with a carbon number of at least 1 and no greater than 6, and a6, a7, a8, and a9 each represent, independently of one another, an integer of at least 0 and no greater than 5,
in the formula (20): R 21 and R 22 each represent, independently of one another, a phenyl group, an alkyl group with a carbon number of at least 1 and no greater than 8, or an alkoxy group with a carbon number of at least 1 and no greater than 8; R 23 to R 29 each represent, independently of one another, a hydrogen atom, an alkyl group with a carbon number of at least 1 and no greater than 8, a phenyl group optionally substituted with an alkyl group with a carbon number of at least 1 and no greater than 8, or an alkoxy group with a carbon number of at least 1 and no greater than 8; any adjacent two of the chemical groups R 25 to R 29 may be bonded to form a ring; and a1 and a2 each represent, independently of one another, an integer of at least 0 and no greater than 5,
in the formula (21): R 31 to R 36 each represent, independently of one another, a phenyl group or an alkyl group with a carbon number of at least 1 and no greater than 8; R 37 and R 38 each represent, independently of one another, a hydrogen atom, a phenyl group, or an alkyl group with a carbon number of at least 1 and no greater than 8; b1, b2, b3, and b4 each represent, independently of one another, an integer of at least 0 and no greater than 5; b5 and b6 each represent, independently of one another, an integer of at least 0 and no greater than 4; and d and e each represent, independently of one another, 0 or 1, and
in the formula (22), R 41 to R 46 each represent, independently of one another, a phenyl group, an alkyl group with a carbon number of at least 1 and no greater than 8, or an alkoxy group with a carbon number of at least 1 and no greater than 8; f1, f2, f4, and f5 each represent, independently of one another, an integer of at least 0 and no greater than 5; and f3 and f6 each represent, independently of one another, an integer of at least 0 and no greater than 4.

11. The electrophotographic photosensitive member according to claim 9 , wherein
the hole transport material includes a compound represented by formula (HTM-1), (HTM-2), (HTM-3), (HTM-4), (HTM-5), (HTM-6), or (HTM-7)

12. The electrophotographic photosensitive member according to claim 9 , 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 the binder resin, and
the charge transport layer provided as an outermost layer.

Assignees

• Kyocera Document Solutions Inc

Inventors

• Azuma Jun
• Maruo Keiji
• Kitaguchi Kenji

Classifications

• C08G63/672

  Dicarboxylic acids and dihydroxy compounds · CPC title

• G03G5/06145

  triamine or greater · CPC title

• C08G63/183

  Terephthalic acids · CPC title

• C08G63/193

  containing two or more aromatic rings · CPC title

• C08G63/185

  containing two or more aromatic rings · CPC title