Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus

A quinone compound, electrophotographic technology, applied in electrical recording process applying charge pattern, equipment, optics, etc., to achieve the effects of improving electrical properties, reducing notch wave, and excellent repeat stability

Inactive Publication Date: 2009-02-18
FUJI ELECTRIC DEVICE TECH CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] As an electron-transporting charge-transporting substance, for example, 2,4,7-trinitro-9-fluorenone is known, but this substance has carcinogenicity, which poses a safety problem

Method used

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  • Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus
  • Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus
  • Quinone compound, electrophotographic photosensitive body and electrophotographic apparatus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131] Synthesis Example 1: Synthesis of the compound of the above-mentioned specific example (I-8)

[0132] (1) Synthesis of dihydrazone

[0133] 100.0 mL of concentrated hydrochloric acid was added to 28.0 g (124.2 mmol) of tin(II) chloride dihydrate and 737.3 mg (6.2 mmol) of tin, and heated and stirred until the tin was dissolved. 100.0 mL of concentrated hydrochloric acid was added to 10.0 g (31.1 mmol) of 2,2',5,5'-tetrachlorobenzidine, and stirred at room temperature for 1 hour until the amine crystals became a slurry. After cooling to -20°C, 18 ml of an aqueous solution of 4.5 g (65.2 mmol) of sodium nitrite was added dropwise over 30 minutes, followed by stirring for 1 hour. The above-mentioned tin chloride solution was cooled to 5° C., and added dropwise to the diazotization solution over 30 minutes. After the completion of the addition, the mixture was stirred for 1 hour, and the generated solid was separated by filtration with a glass filter, and washed with 10...

Embodiment 2

[0143] Synthesis Example 2: Synthesis of the compound of the above-mentioned specific example (I-21)

[0144] (1) Synthesis of dihydrazone

[0145] Using 10.0 g (31.2 mmol) of 2,2'-bistrifluoromethylbenzidine, it was synthesized in the same manner as in Synthesis Example 1-(1) to obtain 24.0 g (30.7 mmol) of the title compound.

[0146] Yield 98.2%, mp223℃~226℃

[0147] 1 H-NMR (500MHz, CDCl 3 )

[0148] δ1.48(s, 36H), δ5.38(s, 2H), δ7.18(d, J=8.5Hz, 2H), δ7.23(dd, J=8.5Hz, 2.4Hz, 2H), δ7 .42(d, J=2.4Hz, 2H), δ7.51(s, 4H), δ7.61(brs, 2H), δ7.72(s, 2H)

[0149] MS (m / z): 783, 551, 319, 190

[0150] (2) Synthesis of the compound of specific example (I-21)

[0151] Using 5.00 g (6.39 mmol) of the hydrazone compound obtained in Synthesis Example 2-(1), it was synthesized in the same manner as in Synthesis Example 1-(2) to obtain 3.18 g (4.08 mmol) of the title compound.

[0152] Yield 63.9%, mp149℃~154℃

[0153] 1 H-NMR (500MHz, CDCl 3 )

[0154] δ1.37(s, 18H), δ1.39...

Embodiment 3

[0156] Synthesis Example 3: Synthesis of the compound of the above specific example (I-28)

[0157] (1) Synthesis of 2,2'-bistrifluoromethyl-5,5'-dibromobenzidine

[0158] Under a nitrogen atmosphere, 20.0 g (62.5 mmol) of 2,2'-bistrifluoromethylbenzidine was dissolved in 100 mL of ethanol, and 21.0 g (131.2 mmol) of bromine was added dropwise over 1 hour under ice-cooling. After stirring at room temperature for 1 hour, toluene was added, and the organic phase was washed three times with water, and then washed twice each with saturated sodium bicarbonate water and water. After concentration, it was recrystallized from hexane / toluene to obtain 11.5 g (24.1 mmol) of the title compound.

[0159] Yield 38.5%, mp154℃~157℃

[0160] 1 H-NMR (500MHz, CDCl 3 )

[0161] δ4.33(s, 4H), δ7.05(s, 2H), δ7.32(s, 2H)

[0162] MS (m / z): 478, 298

[0163] (2) Synthesis of dihydrazone

[0164] Using 5.0g (10.5mmol) of 2,2'-bistrifluoromethyl-5,5'-dibromobenzidine, synthesized in the sam...

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Abstract

Disclosed is a compound having excellent electron transporting ability, which is useful for electrophotographic photosensitive bodies or organic EL devices. Also disclosed is a highly sensitive, positive charge type electrophotographic photosensitive body for copying machines and printers, wherein the novel organic material is used as a charge-transporting material in a photosensitive layer. Further disclosed is an electrophotographic apparatus using such a positive charge type electrophotographic photosensitive body. Specifically disclosed is a novel quinone compound having a structure represented by the general formula (I) below. Also specifically disclosed is an electrophotographic photosensitive body having a photosensitive layer formed on a conductive base and containing a charge-generating material and a charge-transporting material, wherein the photosensitive layer contains at least one of the above-described compounds.

Description

technical field [0001] The present invention relates to a novel quinone compound, and more specifically, to a novel quinone compound useful as a charge-transporting material such as an electrophotographic photoreceptor (hereinafter simply referred to as a "photoreceptor"). Furthermore, the present invention relates to a photoreceptor for electrophotography and an electrophotographic device, in particular, to a photoreceptor for electrophotography used in an electrophotographic printer, copier, etc., in which a photosensitive layer containing an organic material is provided on a conductive substrate. body and an electrophotographic device using the photoreceptor. Background technique [0002] Conventionally, as a photosensitive layer of a photoreceptor for electrophotography, an inorganic photoconductive substance such as selenium or a selenium alloy, and an inorganic photoconductive substance such as zinc oxide or cadmium sulfide dispersed in a resin binder have been used. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03G5/06
CPCG03G2215/00957G03G5/0605G03G5/0679G03G5/0696G03G5/0618C07C225/20C07C245/06
Inventor 大仓健一中村洋一竹嶋基浩长谷川良树剑持宏行小林透
Owner FUJI ELECTRIC DEVICE TECH CO
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