Polyarylate resin and electrophotographic photosensitive member

Patent metadata

Field	Value
Publication number	US-10509309-B2
Application number	US-201815899400-A
Country	US
Kind code	B2
Filing date	Feb 20, 2018
Priority date	Feb 28, 2017
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

A polyarylate resin is represented by general formula (1) shown below. In general formula (1), R 1 represents a hydrogen atom or methyl group. R 2 and R 3 each represent a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4. R 2 and R 3 are not the same as one another. When R 1 represents a hydrogen atom, R 2 and R 3 are not bonded to one another. When R 1 represents a methyl group, R 2 and R 3 are optionally bonded to one another to form a ring. r and s each represent a number greater than or equal to 0 and less than or equal to 49. t and u each represent a number greater than or equal to 1 and less than or equal to 50. r+s+t+u=100. r+t=s+u.

First claim

What is claimed is:

1. A polyarylate resin represented by general formula (1) shown below

wherein in general formula (1),
R 1 represents a hydrogen atom or a methyl group,
R 2 and R 3 each represent a hydrogen atom or an alkyl group having a carbon number of at least 1 and no greater than 4,
R 2 and R 3 are not the same as one another,
when R 1 represents a hydrogen atom, R 2 and R 3 are not bonded to one another,
when R 1 represents a methyl group, R 2 and R 3 are optionally bonded to one another to form a ring,
r and s each represent a number greater than or equal to 0 and less than or equal to 49,
t and u each represent a number greater than or equal to 1 and less than or equal to 50,
r+s+t+u=100, and
r+t=s+u.

2. The polyarylate resin according to claim 1 , wherein
in general formula (1),
R 2 and R 3 each represent an alkyl group having a carbon number of at least 1 and no greater than 4.

3. The polyarylate resin according to claim 1 , wherein
in general formula (1),
one of R 2 and R 3 represents a methyl group, and
the other of R 2 and R 3 represents an ethyl group.

4. The polyarylate resin according to claim 1 , wherein
in general formula (1),
R 1 represents a methyl group, and
R 2 and R 3 are bonded to one another to represent a cycloalkylidene group having a carbon number of at least 5 and no greater than 7.

5. The polyarylate resin according to claim 1 , wherein
in general formula (1),
s/(s+u) is at least 0.30 and no greater than 0.70.

6. The polyarylate resin according to claim 1 , wherein
general formula (1) is represented by chemical formula (R-1), chemical formula (R-2), chemical formula (R-3), chemical formula (R-4), chemical formula (R-5), chemical formula (R-6), or chemical formula (R-7) shown below.

7. 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 .

8. The electrophotographic photosensitive member according to claim 7 , wherein
the hole transport material includes a compound represented by general formula (2), (3), or (4) shown below

wherein in general formula (2),
Q 1 represents a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, an alkoxy group having a carbon number of at least 1 and no greater than 8, or a phenyl group optionally substituted with an alkyl group having a carbon number of at least 1 and no greater than 8,
Q 2 represents an alkyl group having a carbon number of at least 1 and no greater than 8, an alkoxy group having a carbon number of at least 1 and no greater than 8, or a phenyl group,
Q 3 , Q 4 , Q 5 , Q 6 , and Q 7 each represent, independently of one another, a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, an alkoxy group having a carbon number of at least 1 and no greater than 8, or a phenyl group,
adjacent two members among Q 3 , Q 4 , Q 5 , Q 6 , and Q 7 are optionally bonded to one another to form a ring,
a represents an integer of at least 0 and no greater than 5, and
when a represents an integer of at least 2 and no greater than 5, chemical groups Q 2 bonded to the same phenyl group may be the same as or different from one another,
in general formula (3),
Q 8 , Q 10 , Q 11 , Q 12 , Q 13 , and Q 14 each represent, independently of one another, a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, an alkoxy group having a carbon number of at least 1 and no greater than 8, or a phenyl group,
Q 9 and Q 15 each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 8, an alkoxy group having a carbon number of at least 1 and no greater than 8, or a phenyl group,
b represents an integer of at least 0 and no greater than 5,
when b represents an integer of at least 2 and no greater than 5, chemical groups Q 9 bonded to the same phenyl group may be the same as or different from one another,
c represents an integer of at least 0 and no greater than 4,
when c represents an integer of at least 2 and no greater than 4, chemical groups Q 15 bonded to the same phenyl group may be the same as or different from one another, and
k represents 0 or 1, and
in general formula (4),
R a , R b , and R c each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 8, a phenyl group, or an alkoxy group having a carbon number of at least 1 and no greater than 8,
q represents an integer of at least 0 and no greater than 4,
when q represents an integer of at least 2 and no greater than 4, chemical groups R c bonded to the same phenyl group may be the same as or different from one another,
m and n each represent, independently of one another, an integer of at least 0 and no greater than 5,
when m represents an integer of at least 2 and no greater than 5, chemical groups R b bonded to the same phenyl group may be the same as or different from one another, and
when n represents an integer of at least 2 and no greater than 5, chemical groups R a bonded to the same phenyl group may be the same as or different from one another.

9. The electrophotographic photosensitive member according to claim 8 , wherein
in general formula (2),
Q 1 represents a hydrogen atom or a phenyl group substituted with an alkyl group having a carbon number of at least 1 and no greater than 8,
Q 2 represents an alkyl group having a carbon number of at least 1 and no greater than 8,
Q 3 , Q 4 , Q 5 , Q 6 , and Q 7 each represent, independently of one another, a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 8, or an alkoxy group having a carbon number of at least 1 and no greater than 8,
adjacent two members among Q 3 , Q 4 , Q 5 , Q 6 , and Q 7 are optionally bonded to one another to form a ring, and
a represents 0 or 1,
in general formula (3),
Q 8 , Q 10 , Q 11 , Q 12 , Q 13 , and Q 14 each represent, independently of one another, a hydrogen atom, an alkyl group having a carbon number of at least 1 and no greater than 4, or a phenyl group,
b and c each represent 0, and
k represents 0 or 1, and
in general formula (4),
R a and R b each represent, independently of one another, an alkyl group having a carbon number of at least 1 and no greater than 4,
m and n each represent, independently of one another, an integer of at least 0 and no greater than 2, and
q represents 0.

10. The electrophotographic photosensitive member according to claim 8 , wherein
the hole transport material includes a compound represented by chemical formula (HTM-1), chemical formula (HTM-2), chemical formula (HTM-3), chemical formula (HTM-4), chemical formula (HTM-5), chemical formula (HTM-6), chemical formula (HTM-7), chemical formula (HTM-8), or chemical formula (HTM-9) shown below.

Assignees

• Kyocera Document Solutions Inc

Inventors

• Azuma Jun

Classifications

• G03G5/056 Primary

  Polyesters · CPC title

• C08G63/195

  Bisphenol A · CPC title

• C07C211/54

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

• C08G63/189

  containing a naphthalene ring · CPC title

• G03G5/0672

  containing two or more methine or polymethine groups · CPC title