Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Radiation-sensitive composition or product
Reexamination Certificate
2000-07-27
2002-05-21
Rodee, Christopher (Department: 1753)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Radiation-sensitive composition or product
C430S078000, C430S083000, C430S135000, C540S122000, C540S123000, C540S128000, C540S130000, C540S139000, C540S140000, C540S141000
Reexamination Certificate
active
06391505
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a phthalocyanine crystal associating with an organic acceptor compound, its production method, and a high-sensitivity electrophotosensitive material containing the same.
With the development of a non-impact printer technique, an electrographic photoprinter using laser beam or LED as a light source,which is capable of attaining high image quality and high speed, has widely been used and a photosensitive material which responds to the demands has intensively been developed, recently. Among these photosensitive materials, an organic photosensitive material has widely been used because of its easy production, wide range of choice of photosensitive materials and high functional design freedom as compared with a conventional inorganic photosensitive material.
The organic photosensitive material includes, for example, single-layer type photosensitive material wherein an electric charge transferring material is dispersed in the same photosensitive layer, together with an electric charge transferring material, and function-separation type 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.
When using a laser as a light source, a semiconductor laser is exclusively used because of its small size, cheap price, and simplicity. The oscillation wavelength of the semiconductor laser is not less than 750 nm at present and is limited to an infrared range. Accordingly, an organic photosensitive material having the sensitivity at a wavelength within a range from 750 to 850 nm is required.
As the electric charge generating material used in the organic photosensitive material, which satisfies the above demands, for example, polycyclic quinone pigment, pyrylium dye, squarium pigment, phthalocyanine pigment, and azo pigment have been suggested or put into practice.
Among the above electric charge generating materials, most popular phthalocyanine pigments include, for example, metal-free phthalocyanine having no center metal and metallic phthalocyanine having a center metal, and they have various crystal forms such as &agr;, &bgr;, and &ggr; forms. The presence or absence and kind of the center metal as well as crystal form exert a large influence on the charging properties and sensitivity of the photosensitive material.
As the method of attaining a high-sensitivity photosensitive material using phthalocyanine, for example, a method of adding an organic acceptor compound in a photosensitive material has been studied. Japanese Unexamined Patent Publication (Kokai) No. 7-104495 describes a method of adding an organic acceptor compound in an electric charge generating layer of a multi-layer photosensitive material, while Japanese Unexamined Patent Publication (Kokai) No. 6-123984 describes a method of adding an organic acceptor compound in a binder of a single-layer photosensitive material.
However, any of the above methods is a method of adding an organic acceptor compound in the production process of a photosensitive material, that is, a method of adding an organic acceptor compound in the production process of a coating solution for photosensitive layer. A high-speed image forming apparatus has such a problem that the photosensitivity of its photosensitive material is poor, and a further improvement in photosensitivity is required.
SUMMARY OF THE INVENTION
Thus, an object of the present invention is to provide a novel phthalocyanine crystal useful as an electric charge generating material, and a production method thereof.
Another object of the present invention is to provide an extra-high-sensitivity electrophotosensitive material containing the above phthalocyanine crystal.
The present inventors have intensively studied to attain the above object and found that a photosensitive material containing, as an electric charge generating material, a phthalocyanine crystal produced by adding an organic acceptor compound in a photosensitive layer during the step of converting into a pigment, not produced by merely adding the organic acceptor in the photosensitive layer.
Thus, the present inventions relate to:
1. A phthalocyanine crystal in which an organic acceptor compound whose reduction potential to a reference electrode (Ag
+
/Ag) is not less than −1.5 V and not more than −0.5 V is associated with a phthalocyanine molecule.
2. The phthalocyanine crystal according to the above item 1, wherein said phthalocyanine is a metal-free phthalocyanine.
3. The phthalocyanine crystal according to the above item 1, wherein said phthalocyanine is a metal phthalocyanine represented by the general formula (1):
wherein M is a metal of the groups IIa, IIIa, IVa, Va, VII, Ib, IIb, IIIb, IVb or VIb on the periodic table, or a group containing the metal.
4. The phthalocyanine crystal according to the above item 3, wherein the group containing the metal is in the form of oxide, hydroxide, halide or cyanide.
5. The phthalocyanine crystal according to the above item 3, wherein M is TiO.
6. The phthalocyanine crystal according to the above item 1, wherein a solubility of said organic acceptor compound in a solvent in a coating solution for photosensitive layer is less than 10% by weight.
7. The phthalocyanine crystal according to the above item 6, wherein said solvent in a coating solution for photosensitive layer is alcohols, ketones or ethers.
8. The phthalocyanine crystal according to the above item 1, wherein said organic acceptor compound contains a compound represented by the general formula (2):
wherein R
1
, R
2
, R
3
and R
4
are the same or different and each represents a hydrogen atom, a halogen atom, or an alkyl, alkyl halide, alkoxy, aryl, aralkyl, cycloalkyl, cyano, nitro or amino group which may have a substituent, with a proviso that R
1
and R
2
, or R
3
and R
4
may be combined with each other to form a ring.
9. The phthalocyanine crystal according to the above item 1, wherein said organic acceptor compound contains a compound represented by the general formula (3):
wherein R
5
, R
6
, R
7
, R
8
, R
9
, R
10
, R
11
and R
12
are the same or different and each represents a hydrogen atom, a halogen atom, or an alkyl, alkyl halide, alkoxy, aryl, aralkyl, cycloalkyl, cyano, nitro or amino group which may have a substituent, with a proviso that R
5
and R
6
, R
7
and R
8
, R
9
and R
10
, or R
11
and R
12
may be combined with each other to form a ring; and A
1
represents a saturated or unsaturated alkyl group which may have a substituent, an aryl group, or a heterocycle which may have a substituent.
10. The phthalocyanine crystal according to the above item 1, wherein said organic acceptor compound contains a compound represented by the general formula (4):
wherein X
1
, X
2
, X
3
and X
4
are the same or different and each represents an oxygen atom or C(CN)
2
; R
13
, R
14
and R
15
are the same or different and each represents a hydrogen atom, a halogen atom, or an alkyl, alkyl halide, alkoxy, aryl, aralkyl, cycloalkyl, cyano, nitro or amino group which may have a substituent; and Y
1
and Y
2
are the same or different and each represents a carbon atom, an oxygen atom, or a nitrogen atom.
11. The phthalocyanine crystal according to the above item 1, wherein said organic acceptor compound contains a compound represented by the general formula (5):
wherein X
5
and X
6
are the same or different and each represents an oxygen atom or C(CN)
2
; and R
16
, R
17
and R
18
are the same or different and each represents a hydrogen atom, a halogen atom, or an alkyl, alkyl halide, alkoxy, aryl, aralkyl, cycloalkyl, cyano, nitro or amino group which may have a substituent, with a proviso that R
16
and R
17
may be combined with each other to form a ring.
12. A phthalocyanine crystal in which an organic acceptor compound is associated with a phthalocyanine molecule, which is produced by adding the
Hamasaki Kazunari
Watanabe Yukimasa
Kyocera Mita Corporation
Rodee Christopher
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