Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Radiation-sensitive composition or product
Reexamination Certificate
2000-08-25
2002-01-15
Goodrow, John (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Radiation-sensitive composition or product
C430S083000, C564S434000
Reexamination Certificate
active
06338927
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a stilbene derivative having high compatibility with a binder resin, high sensitivity and excellent stability, a method of producing the same, and an electrophotosensitive material containing the stilbene derivative used in image forming apparatuses such as electrostatic copying machine, facsimile and laser beam printer.
In the image forming apparatuses, various organic photosensitive materials having the sensitivity within a wavelength range of a light source used in the apparatus are used. Recently, the organic photosensitive material has widely been used because it is easily produced as compared with a conventional inorganic photosensitive material and that it has advantages such as wide range of choice of photosensitive materials such as electric charge transferring material, electric charge generating material and binder resin, and high functional design freedom.
The organic photosensitive material includes a single-layer type photosensitive material wherein an electric charge transferring material and an electric charge generating material are dispersed in the same photosensitive layer, and a multi-layer type photosensitive material comprising an electric charge generating layer containing an electric charge generating material and an electric charge transferring layer containing an electric charge transferring material, which are mutually laminated.
Japanese Published Unexamined Patent Application (Kokai Tokkyo Koho Sho) No. 50-31773 and Japanese Published Unexamined Patent Application (Kokai Tokkyo Koho Hei) No. 7-244389 disclose a stilbene derivative as the electric charge transferring material used in the organic photosensitive material.
However, the stilbene derivative disclosed in the above patent applications is not uniformly dispersed in the photosensitive layer and charge transfer hardly occurs because of its poor compatibility with a binder resin. Therefore, the stilbene derivative itself has high charge mobility. However, when using the stilbene derivative as the electric charge transferring material in the photosensitive material, its characteristics can not be sufficiently exhibited so that the residual potential of the photosensitive material increases and the sensitivity to light becomes insufficient.
SUMMARY OF THE INVENTION
An object of the present invention is to solve the technical problems described above and to provide a novel stilbene derivative suited for use as an electric charge transferring material of an electrophotosensitive material, and a method of producing the same.
Another object of the present invention is to provide an electrophotosensitive material having improved sensitivity and repeatability as compared with a conventional electrophotosensitive material.
To attain the objects described above, the present inventors has studied intensively and found the following fact. Among the stilbene derivative, a compound, wherein molecular structures of triphenylamino groups located at both sides of a benzene ring in a molecular center are unsymmetric with respect to the benzene ring, is superior in compatibility with a binder resin to a conventional stilbene derivative and has a large charge mobility. Thus, the present invention has been completed.
That is, the present invention is directed to a stilbene derivative, a method of preparing the same, and an electrophotosensitive material using the same.
1. A stilbene derivative wherein molecular structures of triphenylamino groups located at both sides of a benzene ring in a molecular center are unsymmetric with respect to the benzene ring.
2. The stilbene derivative according to the term 1, which is represented by the general formula (1):
wherein R
1
to R
24
are the same or different and each represents an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydrogen atom, or a nitro group; R
25
and R
26
each represents a vinylene group; at least one of the pairs of a combination of R
n
and R
n+5
and a combination of R
m
+R
m+2
represent different substituents; at least two substituents of the group consisting of R
1
to R
5
, R
6
to R
10
R
11
to R
15
, and R
16
to R
20
represent a hydrogen atom; n represents an integer of 1 to 10; and m represents 21 or 22.
3. The stilbene derivative according to the term 2, wherein at least one of the pairs of R
21
and R
23
, R
22
and R
24
, and R
25
and R
26
represent different substitution positions from that of a nitrogen atom attached through a benzene ring.
4. The stilbene derivative according to the term 2, wherein at least one of R
1
, R
6
, R
11
and R
16
represent an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, and an optionally substituted aralkyl group.
5. The stilbene derivative according to the term 1, which is represented by the general formula (2):
wherein R
1
to R
24
are the same or different and each represents an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, an optionally substituted aralkyl group, a hydrogen atom, or a nitro group; R
25
and R
26
each represents a vinylene group; R
n
and R
n+5
each represents the same group; R
m
and R
m+2
each represents the same group; at least one of the pairs of R
21
and R
23
, R
22
and R
24
, and R
25
and R
26
represent different substitution positions from that of a nitrogen atom attached through a benzene ring; n represents an integer of 1 to 10; and m represents 21 or 22.
6. The stilbene derivative according to the term 5, wherein at least one of R
1
, R
6
, R
11
and R
16
is an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aryl group, or an optionally substituted aralkyl group.
7. A method of producing the stilbene derivative of the term 2, which comprises reacting an aldehyde derivative represented by the general formula (3):
wherein R
1
to R
5
, R
11
to R
15
, R
21
, R
22
and R
25
are as defined in the general formula (1), with a triphenylamine phosphate derivative represented by the general formula (4):
wherein R
6
to R
10
, R
16
to R
20
, R
23
and R
24
are as defined in the general formula (1).
8. A method of producing the stilbene derivative of the term 2, which comprises reacting a formylated triphenylamine derivative represented by the general formula (5):
wherein R
1
to R
5
, R
11
to R
15
, R
21
and R
22
are as defined in the general formula (1), with a monostilbene derivative represented by the general formula (6):
wherein R
6
to R
10
, R
16
to R
20
, R
23
, R
24
and R
26
are as defined in the general formula (1).
9. A method of producing the stilbene derivative of the term 5, which comprises reacting an aldehyde derivative represented by the general formula (3):
wherein R
1
to R
5
, R
11
to R
15
, R
21
, R
22
and R
25
are as defined in the general formula (1), with a triphenylamine phosphate derivative represented by the general formula (4):
wherein R
6
to R
10
, R
16
to R
20
, R
23
and R
24
are as defined in the general formula (1).
10. A method of producing the stilbene derivative of the term 5, which comprises reacting a formylated triphenlamine derivative represented by the general formula (5):
wherein R
1
to R
5
, R
11
to R
15
, R
21
and R
22
are as defined in the general formula (1), with a monostilbene derivative represented by the general formula (6):
wherein R
6
to R
10
, R
16
to R
20
, R
23
, R
24
and R
26
are as defined in the general formula (1).
11. An electrophotosensitive material comprising a conductive substrate and a photosensitive layer formed on the substrate, the photosensitive layer containing at least one of the stilbene derivatives of the term 1.
12. An electrophotosensitive material comprising a conductive substrate and a photosensitive layer formed on the substrate, the photosensitive layer containing at least one of the
Inagaki Yoshio
Watanabe Yukimasa
Goodrow John
Kyocera Mita Corporation
Smith , Gambrell & Russell, LLP
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