Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Radiation-sensitive composition or product
Reexamination Certificate
1999-06-15
2001-05-08
Dote, Janis L. (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Radiation-sensitive composition or product
C430S058750, C430S058850, C430S059400, C430S073000, C430S075000, C430S083000, C549S435000
Reexamination Certificate
active
06228547
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel bis(3,4-methylenedioxyphenylamino) derivatives represented by the following general formula (1) and an electrophotographic photoreceptor containing one or more of the derivatives:
wherein Ar
1
and Ar
2
may be the same or different and each represents an optionally substituted aryl group; and Ar
3
represents a divalent aromatic group represented by
wherein R
1
and R
2
each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, provided that when Ar
3
is a phenylene group, one of the amino substituents is meta or para to the other.
BACKGROUND OF THE INVENTION
Recently, printers as terminal recording apparatuses in the field of information communications are being strongly required more and more to be of smaller size and capable of higher-rate printing and color printing. Because of this, electrophotographic photoreceptors for use in electrophotographic laser beam printers or LED printers have come to be required to be of even smaller size and capable of coping with a higher printing rate.
In order to obtain such an excellent electrophotographic photoreceptor, it is, of course, necessary to employ a charge-generating substance and a charge-transporting substance each having satisfactory properties. Besides this, it is also important that the injection of charge carriers from the charge-generating substance into the charge-transporting substance, i.e., the injection of charges from a charge-generating layer into a charge-transporting layer, should be efficiently conducted. Since this charge injection depends on the properties of the interface between the charge-generating substance (or charge-generating layer) and the charge-transporting substance (or charge-transporting layer) and varies with combinations of various substances, charge-transporting substances having a variety of properties are being developed.
N,N′-Diphenyl-N,N′-bis(3-methylphenyl)-4,4-biphenylenediamine (4) is already known to effectively function as a charge-transporting material (see JP-B-58-32372 (the term “JP-B” as used herein means an “examined Japanese patent publication”) and U.S. Pat. No. 3,265,496).
Several diaminobiphenyl compounds also are known as charge-transporting materials (see JP-B-63-6864, JP-B-5-40904, Japanese Patent 2,539,641, EP 0648737 A1, JP-A-6-199745 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”), JP-A-6-293716, JP-A-7-188130, JP-A-7-181693, and U.S. Pat. No. 5,399,453).
Electrophotographic photoreceptors are known which employ a mixture of a diaminobiphenyl compound having two or more alkoxy groups on the same aromatic ring and other charge-transporting material(s) (see JP-A-7-225486, JP-A-6-342215, JP-A-6-342220, JP-A-6-342218, JP-A-6-342217, JP-A-6-342216, JP-A-5-341545, and JP-A-5-341544).
Combinations of a diaminobiphenyl compound and a binder polymer are known (see JP-A-7-120941, JP-A-6-214412, and JP-A-6-130685).
Also known are combinations of a diaminobiphenyl compound and a charge-generating material (see JP-A-6-75408, JP-A-6-161132, JP-A-6-75403, JP-A-5-257310, JP-A-5-188615, JP-A-5-281769, and JP-A-5-257309).
Applications of m-diaminobenzene derivatives to materials for electrophotographic photoreceptors are described, e.g., in JP-A-1-142642 and JP-A-5-88389. An m-diaminobenzene derivative having a fluoroalkyl group bonded to the central benzene ring is described in JP-A-7-126224, and an electrophotographic photoreceptor employing this derivative is described in JP-A-1-128880. JP-A-3-105347 discloses an m-diaminobenzene derivative having a thiocarbonyl group. An m-diaminobenzene derivative having a methoxy group and a phenyl group bonded as substituents to the central phenyl group is described in JP-A-2-93653, and an electrophotographic photoreceptor employing this derivative is described in JP-A-2-93654. In JP-A-5-58966 and JP-A-5-301848 are disclosed m-diaminobenzene derivatives in which one of the amino groups is substituted with a pyrene ring. JP-A-4-300853 discloses a diaminobenzene derivative having an olefin substituent and an electrophotographic photoreceptor employing this derivative. Furthermore, an electrophotographic photoreceptor employing a diaminobenzene compound having three or four amino substituents in the molecule is disclosed in JP-A-3-94258 and JP-A-3-94259.
As described above, electrophotographic photoreceptors employing a compound selected from many diaminobiphenyl or diaminobenzene compounds have been proposed. However, these compounds have drawbacks that they are apt to separate out as crystals because of their insufficient solubility, have poor miscibility with binder polymers, and are insufficiently compatible with phthalocyanines suitable for use as charge-generating materials. Consequently, there have been cases where the prior art electrophotographic photoreceptors have insufficient photosensitivity or have a high residual potential to cause scumming.
SUMMARY OF THE INVENTION
An object of the present invention is to provide novel charge-transporting materials having a high carrier mobility and high sensitivity which have satisfactory miscibility with binder polymers, are capable of forming a thin stable organic film having a high concentration, and give an electrophotographic photoreceptor having various excellent properties.
Under the circumstances described above, the present inventors synthesized various compounds and made intensive investigations thereon in order to find out both a charge-transporting material having a high mobility and capable of giving a thin stable organic film even when used at a high concentration and a compound suitable for use in producing a high-performance electrophotographic photoreceptor. As a result, they have found that the problems described above can be eliminated with novel bis(3,4-methylenedioxyphenylamino) derivatives represented by the following general formula (1):
wherein Ar
1
and Ar
2
may be the same or different and each represents an optionally substituted aryl group; and Ar
3
represents a divalent aromatic group represented by
wherein R
1
and R
2
each represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, or a phenyl group, provided that when Ar
3
is a phenylene group, one of the amino substituents is meta or para to the other. The present invention has been completed based on this finding.
The compounds represented by general formula (1), even when used in a high concentration, neither separate out as crystals nor develop pinholes. Photoreceptors employing any of these compounds have high sensitivity and a low residual potential.
The present invention include the following (1) to (5).
(1) Novel bis(3,4-methylenedioxyphenylamino) derivatives represented by general formula (1) described above.
(2) An electrophotographic photoreceptor containing as a charge-transporting material at least one member selected from the novel bis(3,4-methylenedioxyphenylamino)biphenyl derivatives and bis(3,4-methylenedioxyphenylamino)benzene derivatives represented by general formula (1).
(3) An electrophotographic photoreceptor comprising a charge-generating material and a charge-transporting material, wherein the charge-generating material comprises a phthalocyanine and the charge-transporting material comprises a combination of at least one member selected from the bis(3,4-methylenedioxyphenylamino)biphenyl derivatives and bis(3,4-methylenedioxyphenylamino)benzene derivatives represented by general formula (1) and at least one of diaminobiphenyl compounds represented by the following general formula (2):
wherein R
3
and R
4
may be the same or different and each represents a hydrogen atom, a halogen atom, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having 1 to 4 carbon atoms, or a phenyl group; and Ar
4
, Ar
5
, Ar
6
, and Ar
7
may be the same or different and each represents a phenyl group which may have one or more substituents selected from the group consisting of halogen atoms, lower alkyl groups havi
Aoki Yoko
Hagiwara Toshimitsu
Kobayashi Tohru
Matsushima Yoshimasa
Sugiyama Hiroshi
Dote Janis L.
Sughrue Mion Zinn Macpeak & Seas, PLLC
Takasago International Corporation
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