Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
1999-02-19
2001-01-09
Vollano, Jean F (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S315000, C564S434000
Reexamination Certificate
active
06172264
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel triphenylamine derivative represented by the following general formula (1):
wherein R
1
, R
2
, R
3
, R
4
, R
5
, and R
6
may be the same or different and each represents a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, a halogen atom, or an aryl group which may have a substituent group, and m and n each represents 0 or 1. This invention further relates to a charge-transporting material comprising the novel triphenylamine derivative and to an electrophotographic photoreceptor containing the charge-transporting material.
The present invention also relates to a process for the preparation of a triphenylamine derivative represented by the following general formula (6):
wherein R
7
to R
13
may be the same or different and each represents a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, a halogen atom or an aryl group which may have a substituent group; l
1
and l
2
each represents 0 or 1; and Z represents a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, a halogen atom, an aryl group which may have a substituent group or a group represented by any one of the following general formulae (7a), (7b) and (7c):
wherein R
10
to R
13
, l
1
and l
2
are as defined in the foregoing general formula (6); R′ and R″ may be the same or different and each represents a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, a halogen atom or an aryl group which may have a substituent group; and l
3
represents 0 or 1, said triphenylamine derivative including the foregoing novel triphenylamine derivative represented by the general formula (1).
The present invention further relates to a process for the preparation of a poly-formyl-substituted triphenylamine derivative represented by the following general formula (4) useful as an intermediate for the preparation of the foregoing triphenylamine derivative represented by the general formula (1) and/or (6):
wherein R
7
, R
8
and R
9
may be the same or different and each represents a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, an aryl group which may have a substituent group or a halogen atom; and Y represents a formyl group, a hydrogen atom, a lower alkyl group, an alkoxy group, a phenoxy group, a halogen atom or an aryl group which may have a substituent group.
BACKGROUND ART
Inorganic photoconductive materials recently in use include amorphous silicon, amorphous selenium, cadmium sulfide, zinc oxide, and the like. However, some of these materials are expensive because of difficulties in production thereof, while others are toxic and disadvantageous from the standpoint of environmental protection.
On the other hand, as organic photoconductors, ones of the type comprising, in particular, a charge-generating material and a charge-transporting material which respectively perform their functions are proposed extensively (e.g., U.S. Pat. No. 3,791,826). In this type, there is the possibility that a high-sensitivity electrophotographic photoreceptor might be obtained by using a substance which efficiently generates carriers (The term “carriers” means “charges”; the same applies hereinafter) as the charge-generating material in combination with a substance having high charge-transporting ability as the charge-transporting material.
Of these materials, the charge-transporting material is required to efficiently receive the carriers generated in the charge-generating material upon light irradiation in an electric field and permit them to rapidly move through the photosensitive layer to extinguish the surface charges promptly. The speed at which carriers move per unit electric field is called carrier mobility. A high carrier mobility means that carriers rapidly move in the charge-transporting layer. Any charge-transporting material has its intrinsic carrier mobility and, hence, it is necessary that for attaining a high carrier mobility, a material having a high carrier mobility be employed. However, the attainable carrier mobilities have not yet reached a sufficient level.
Further, in the case of applying a charge-transporting material after dissolving it in an organic solvent along with a binder polymer, it is necessary to form a thin homogeneous organic coating film free from crystallization and pinhole formation. This is because when a high electric field is applied to the thin film obtained, the part having microcrystals or pinholes undergoes dielectric breakdown or causes noise.
In addition to the satisfactory properties of the charge-generating material and of the charge-transporting material, it is also important that carriers should be efficiently injected from the charge-generating material into the charge-transporting material, i.e., from the charge-generating layer into the charge-transporting layer. This injection of charges depends on the properties of the interface between the charge-generating material (or charge-generating layer) and the charge-transporting material (or charge-transporting layer) and varies with combinations of various materials. Since a charge-transporting material should meet various requirements as described above, charge-transporting materials having a variety of properties are being developed.
Among conventional charge-transporting materials, the styryl compound represented by formula (A):
is, for example, proposed in JP-A-60-174749. (The term “JP-A” as used herein means an “unexamined published Japanese patent application.”)
Moreover, a styryl compound represented by formula (B):
(wherein R
1
represents an optionally substituted alkyl group or an aryl group which may have a substituent group, R
2
represents a hydrogen atom, an optionally substituted alkyl group, or an aryl group which may have a substituent group, and Ar represents an aryl group which may have a substituent group)
is proposed in JP-A-60-175052.
Furthermore, compounds similar to the compound (B) described above are proposed in, for example, JP-A-62-120346, JP-A-1-217357, JP-A-4-57056, and JP-A-4-292663.
On the other hand, a styryl compound represented by formula (C):
(wherein R
1
, R
3
, and R
5
each represents a hydrogen atom, an alkyl group, an aryl group which may have a substituent group, an optionally substituted aralkyl group, or an optionally substituted heterocyclic group; R
2
, R
4
, and R
6
each represents an aryl group which may have a substituent group, an optionally substituted aralkyl group, or an optionally substituted heterocyclic group; R
1
and R
2
, R
3
and R
4
, and R
5
and R
6
may be bonded to each other to form a ring; and R
7
, R
8
, and R
9
each represents a hydrogen atom, an alkyl group, an alkoxy group, an aralkyl group, or an aryl group) is proposed in JP-B-6-93124. (The term “JP-B” as used herein means an “examined Japanese patent publication.”)
Compounds similar to the compound (C) described above are proposed in JP-A-63-163361 and JP-A-6-332206. In JP-A-4-292663 is proposed a hydrazone compound represented by formula (D):
(wherein R
1
, R
2
, R
3
, R
4
, R
5
, and R
6
may be the same or different and each represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkoxy group, an optionally substituted aralkyl group, or an aryl group which may have a substituent group; Ar
1
, Ar
2
, Ar
3
, Ar
4
, Ar
5
, and Ar
6
may be the same or different and each represents a hydrogen atom, an optionally substituted alkyl group, an aryl group which may have a substituent group, an optionally substituted aralkyl group, or an optionally substituted heterocyclic group; and l, m, and n each represents 0 or 1; provided that Ar
1
, Ar
2
, Ar
3
, Ar
4
, Ar
5
, and Ar
6
should not be a hydrogen atom at the same time).
The demand for charge-transporting materials is growing more and more, with which there is a desire for a newer material which is capable of satisfying various requirements.
In JP-A-4-57056, for example, there is a description to the effect that the compound (E) specified below partly separated out as
Hagiwara Toshimitsu
Kobayashi Tohru
Matsushima Yoshimasa
Sugiyama Hiroshi
Sughrue Mion Zinn Macpeak & Seas, PLLC
Takasago International Corporation
Vollano Jean F
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