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Method of producing gallium phthalocyanine crystal and method of producing electrophotographic photosensitive member using the method of producing gallium phthalocyanine crystal

a gallium phthalocyanine and crystal technology, applied in the field of producing gallium phthalocyanine crystals and producing electrophotographic photosensitive members, can solve the problems of difficult to achieve compatibility between the additional improvement in sensitivity and the improvement of image quality, and the difficulty of transforming the additive into a desired crystal form, etc., to achieve the effect of improving sensitivity, less image defects, and excellent characteristics as a charge-generating substan

Inactive Publication Date: 2015-05-19
CANON KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0014]Further, the present invention is directed to providing a method of producing an electrophotographic photosensitive member having additionally improved sensitivity and capable of outputting an image having less image defects due to the ghost phenomenon not only under a normal-temperature, normal-humidity environment but also under a low-temperature, low-humidity environment as a particularly severe condition.
[0018]According to the present invention, there is provided the gallium phthalocyanine crystal having excellent characteristics as a charge-generating substance.
[0019]Further, according to the present invention, provided is the method of producing the electrophotographic photosensitive member having additionally improved sensitivity and capable of outputting an image having less image defects due to the ghost phenomenon not only under a normal-temperature, normal-humidity environment but also under a low-temperature, low-humidity environment as a particularly severe condition.

Problems solved by technology

However, the electrophotographic photosensitive member involves the following problem.
However, the approach involves the following concern and problem.
The additive may chemically change, thereby being difficult to transform the additive into a desired crystal form.
However, it has been difficult to achieve compatibility between the additional improvement in sensitivity and the improvement in image quality owing to existence of the following dilemma.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

synthesis example

Synthesis of Exemplified Compound (24)

[0045]5.0 Parts of 4,4′-diaminobenzophenone, 25.7 parts of iodotoluene, 9.0 parts of copper powder, and 9.8 parts of potassium carbonate were added to a three-necked flask containing 50 parts of N,N-dimethylacetamide, and then the mixture was refluxed for 20 hours. After that, a solid component was removed by hot filtration. The solvent was removed by distillation under reduced pressure and then the residue was purified with a silica gel column (using toluene as a solvent). Thus, 8.1 parts of Exemplified Compound (24) were obtained.

[0046]Characteristic peaks of an IR absorption spectrum and a 1H-NMR spectrum obtained by measurement are described below.

[0047]IR (cm−1, KBr): 1646, 1594, 1508, 1318, 1277, and 1174

[0048]1H-NMR (ppm, CDCl3, 40°): δ=7.63 (d, 4H), 7.11 (d, 8H), 7.04 (d, 8H), 6.93 (d, 4H), and 2.33 (s, 12H)

[0049]The gallium phthalocyanine to be subjected to the milling treatment together with the formula (1) in the solvent of the presen...

example 1-1

[0113]0.5 Part of hydroxygallium phthalocyanine obtained by the same treatment as that of Example 1-1 subsequent to Synthesis Example 1 described in Japanese Patent Application Laid-Open No. 2011-94101, 1.0 part of Exemplified Compound (1) (product code: 159400050, manufactured by Acros Organics), and 10 parts of N,N-dimethylformamide were subjected to a milling treatment in a ball mill together with 20 parts of glass beads each having a diameter of 0.8 mm at room temperature (23° C.) for 40 hours. A gallium phthalocyanine crystal was taken out of the dispersion with N,N-dimethylformamide and filtered, and then the residue on the filter was sufficiently washed with tetrahydrofuran. The filter residue was vacuum-dried to yield 0.5 part of a hydroxygallium phthalocyanine crystal. FIG. 2 shows the powder X-ray diffraction pattern of the resultant crystal.

[0114]In addition, NMR measurement confirmed that Exemplified Compound (1) was incorporated at 0.31% into the crystal.

example 1-2

[0115]0.45 Part of a hydroxygallium phthalocyanine crystal was obtained by the same treatment as that of Example 1-1 except that in Example 1-1, 1.0 part of Exemplified Compound (1) was changed to 2.0 parts of Exemplified Compound (1). The powder X-ray diffraction pattern of the resultant hydroxygallium phthalocyanine crystal was the same as FIG. 2.

[0116]In addition, NMR measurement confirmed that Exemplified Compound (1) was incorporated at 0.82% into the crystal.

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PUM

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Abstract

Provided is a method of producing an electrophotographic photosensitive member having improved sensitivity and capable of outputting an image having less image defects due to a ghost phenomenon not only under a normal-temperature, normal-humidity environment but also under a low-temperature, low-humidity environment as a particularly severe condition. The method of producing a gallium phthalocyanine crystal includes subjecting a gallium phthalocyanine and a specific amine compound, which are added to a solvent, to a milling treatment to perform crystal transformation of the gallium phthalocyanine. In addition, the gallium phthalocyanine crystal is used in the photosensitive layer of the electrophotographic photosensitive member.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The present invention relates to a method of producing a gallium phthalocyanine crystal and a method of producing an electrophotographic photosensitive member using the method of producing a gallium phthalocyanine crystal.[0003]2. Description of the Related Art[0004]Conventionally, a phthalocyanine-based pigment has been attracting attention, and has been investigated, as an electronic material to be used in an electrophotographic photosensitive member, a solar cell, a sensor, or the like in addition to its application for coloring.[0005]An oscillation wavelength of semiconductor laser, which has been frequently used as an image exposing unit for an electrophotographic photosensitive member, is, at present, a long wavelength such as 650 to 820 nm. Accordingly, development of an electrophotographic photosensitive member having high sensitivity to light having such a long wavelength has been advanced.[0006]The phthalocyan...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): G03G5/06C09B67/50C09B67/04G03G5/05G03G5/147C09B67/12
CPCC09B67/0026C09B67/0002G03G5/0542G03G5/0564G03G5/0614G03G5/0696G03G5/14756C09B67/0016
Inventor TANAKA, MASATOKAWAHARA, MASATAKAWATARIGUCHI, KANAMEMURAKAMI, TAKESHIYOSHIDA, AKIRA
Owner CANON KK
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