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Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same

A naphthalene tetracarboxylic acid diimide, electrophotographic technology, applied in the field of new naphthalene tetracarboxylic acid diimide derivatives, can solve the problems of influence, low electron transfer ability, complex structure and the like

Inactive Publication Date: 2009-03-18
RICOH KK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Charge-generating materials are very susceptible to oxidizing species such as ozone and nitrogen oxide ions, so this type of photoconductor has a problem: they are highly susceptible to gases contained in the working environment (such as exhaust from fan heaters or vehicles)
Also, as a result of repeated use, this derivative causes problematic image blurring
Diphenoquinone derivatives described in JP-B No. 2732697, naphthalene tetracarboxylic acid diimide derivatives (2) or (3) described in International Publication No. 00 / 040657 and JP-A No. 01- The diphenoquinone derivatives described in 206349 have poor compatibility with resins for binders forming photoconductors and cannot sufficiently express their characteristics
Naphthalene tetracarboxylic acid diimide derivatives described in JP-A No. 2005-154409 and U.S. Patent No. 6794102 have complex structures, which cause problems in their production
Naphthalene tetracarboxylic acid diimide derivatives (1) described in the document "Chemistryletters (2003), 32(6), 508-509" have low electron transfer ability and cannot be used for practical applications

Method used

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  • Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same
  • Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same
  • Naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same

Examples

Experimental program
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Effect test

Embodiment 1

[0153] Naphthalene-1,4,5,8-tetracarboxylic dianhydride (product of TOKYO CHEMICAL INDUSTRY CO., LTD.) (5.36 g, 20.0 mmol), N, N-dimethylformamide (30 mL) and acetic acid (3 mL) was added to the bottle, then refluxed. A solution of 2-heptylamine (2.42 g, 21.0 mmol) in N,N-dimethylformamide (6 mL) was added dropwise to the resulting mixture with stirring over about 2 hours. Further, the mixture was reacted for 5 hours under reflux. After cooling, the solvent was evaporated under reduced pressure. Toluene was added to the residue, and insoluble materials were removed by filtration. The filtrate was purified by silica gel chromatography, and then recrystallized from cyclohexane / toluene, thereby yielding 3.02 g of a monoimide compound represented by the following structural formula (i) (yield: 41.3%). The compound was found to have a melting point of 149.0°C to 150.0°C.

[0154] The above compounds were subjected to elemental analysis. The results are shown in Table 6.

[015...

Embodiment 2

[0158] A part (1.83 g, 5.00 mmol) of the monoimide compound obtained in Example 1 was added to N,N-dimethylformamide (15 mL). 1,1-Dibenzylhydrazine (product of TOKYO CHEMICALINDUSTRY CO., LTD.) (1.06 g, 5.00 mmol) was added to the mixture, followed by stirring at 60° C. under an argon stream for 3.5 hours. The solvent (N,N'-dimethylformamide) was evaporated under reduced pressure to form red crystals. The crystals were purified using a silica gel column (eluent: toluene / ethyl acetate (30 / 1 volume ratio)). Orange-red crystals obtained by recrystallization from ethyl acetate / ethanol. The obtained crystals were dried by a drier, and heated under reduced pressure in the drier, thereby yielding 2.21 g of Compound No. 30 represented by the following structural formula (iii) in the form of yellow needles (yield: 78.9%). The compound was found to have a melting point of 147.0°C to 148.0°C.

[0159] The obtained compound was subjected to elemental analysis. The results are shown in...

Embodiment 3 to 21

[0160] Similar to Examples 1 and 2, compounds corresponding to Examples 3 to 21 were produced and analyzed. The results are shown in Tables 9-1 and 9-2.

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Abstract

The invention relates to naphthalenetetracarboxylic acid diimide derivative and electrophotographic photoconductor having the same. The present invention provides a naphthalenetetracarboxylic acid diimide derivative represented by the following general formula (1): wherein R1 and R2, which are identical or different, each represent a substituted or non-substituted alkyl group or a substituted or non-substituted aromatic hydrocarbon group; R 3 represents an alkyl group having 1 to 8 carbon atoms or an aromatic hydrocarbon group; R4, R5, R6 and R7, which are identical or different, each represent a hydrogen atom, a substituted or non-substituted alkyl group, or a substituted or non-substituted aromatic hydrocarbon group; and R 1 and R 2 may be linked to form a substituted or non-substituted heterocyclic group including a nitrogen atom; with compounds where all of R1, R2 and R3 are a methyl group, and compounds where both of R1 and R2 are a methyl group and R3 is a 1-octyl group being excluded.

Description

technical field [0001] The present invention relates to novel naphthalene tetracarboxylic acid diimide derivatives, which can be used in organic electronic materials, especially in organic photoconductor materials. [0002] The present invention also relates to electrophotographic photoconductors comprising a photoconductive layer comprising at least one naphthalene tetracarboxylic diimide derivative. Background technique [0003] Organic electrophotographic photoconductors that have been widely used include organic photoconductor materials. Organic photoconductor materials have been required to meet more stringent needs, such as higher sensitivity and practicality for environmentally sensitive production methods or processes. [0004] An organic electrophotographic photoconductor is formed of a charge generating material and a charge transporting material. Charge transport materials are required to have higher sensitivity, that is, to exhibit high charge transfer ability ...

Claims

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Application Information

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IPC IPC(8): C07D471/06G03G5/047G03G5/06G03G5/04
Inventor 太田正文岛田知幸田中裕二栗本锐司下山启介
Owner RICOH KK
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