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Novel compound and organic electronic device using such compound

A compound and organic group technology, applied in the field of organic solar cells, can solve the problems of inability to transport photocarriers, unstable discharge compared to positive polarity, adverse effects of the use environment, etc., and achieve excellent film stability and excellent electron transfer properties Effect

Inactive Publication Date: 2007-03-28
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The charge transport material used in the above-mentioned photoreceptor is required to have high carrier mobility, but since charge transport materials with high carrier mobility are almost all hole transport substances, it is practical from the viewpoint of mechanical strength. OPC in OPC is limited to negatively charged laminated photoreceptors with a charge transfer layer on the outermost layer
However, since the OPC of the negative charge treatment uses a negative polarity corona discharge, it has the following problems: it is more unstable than the positive polarity discharge, generates ozone or nitrogen oxides, etc., and easily causes physical and chemical deterioration by adsorption on the surface of the photoreceptor. , but also cause adverse effects on the use environment, etc.
However, the photocarriers generated in the mixed layer cannot be efficiently transferred to the electrodes, so further improvement in efficiency is required for practical use.

Method used

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  • Novel compound and organic electronic device using such compound
  • Novel compound and organic electronic device using such compound
  • Novel compound and organic electronic device using such compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0347]

[0348] Synthesis of naphthalene monoimide (1-1) in the first step

[0349] The reaction container containing 8.0 g of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 50 ml of dehydrated DMF was charged under reflux under heating. Then, 30 ml of dehydrated DMF dissolved in 3.85 g of 2-ethylhexylamine was added dropwise while stirring. After the dropwise addition was completed, it was further heated to reflux for 6 hours. After cooling, it was concentrated under reduced pressure, the residue was diluted with toluene, and the insoluble components were filtered off. Purify by silica gel chromatography to obtain the target naphthalene monoimide (1-1). Yield: 3.89g.

[0350] The second step synthesizes naphthalene monoimide monohydrazone derivatives (1-2)

[0351] 12.0 g of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 60 ml of dehydrated DMF were placed in the reaction container heated to reflux. Then, 5.78 g of 2-aminooctane was dissolved in 30 ml of deh...

Embodiment 2

[0358]

[0359] Synthesis of naphthalene monoimide (2-1) in the first step

[0360] The reaction container containing 27.0 g of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 250 ml of dehydrated DMF was charged under reflux under heating. Then, 9.0 g of 3-aminopentane was dissolved in 100 ml of dehydrated DMF dropwise over 30 minutes while stirring. After the dropwise addition was completed, it was further heated to reflux for 6 hours. After cooling, it was concentrated under reduced pressure, the residue was diluted with toluene, and the insoluble components were filtered off. Purification was carried out by silica gel column chromatography to obtain the light yellow target monoimide (2-1). Yield: 13.3g.

[0361] The second step synthesizes naphthalene monoimide monohydrazone derivatives (2-2)

[0362] 10.0 g of the naphthalene monoimide (2-1) obtained above and 100 ml of dehydrated DMF were charged and dissolved. Then, 1.65 g of hydrazine monohydrate was added dr...

Embodiment 3

[0367]

[0368] Synthesis of naphthalene monoimide (3-1) in the first step

[0369] The reaction container containing 42.0 g of naphthalene-1,4,5,8-tetracarboxylic dianhydride and 400 ml of dehydrated DMF was charged under reflux under heating. Then, 18.9 g of 2-heptylamine was dissolved in 100 ml of dehydrated DMF dropwise over 50 minutes while stirring. After the dropwise addition was completed, it was further heated to reflux for 6 hours. After cooling, it was concentrated under reduced pressure, the residue was diluted with toluene, and the insoluble components were filtered off. Purify by silica gel column chromatography to obtain the light yellow target monoimide (3-1). Yield: 25.3g.

[0370] The second step synthesizes naphthalene monoimide monohydrazone derivatives (3-2)

[0371] The same method as the second step of Example 2 was used for preparation.

[0372] third step

[0373] A reaction vessel containing 2.66 g of naphthalene monoimide monohydrazone deriv...

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Abstract

Disclosed is a novel compound suitable as an electron-transporting material for organic electronic devices. Also disclosed is an organic electronic device using such a compound which has higher sensitivity and longer life than conventional organic electronic devices. Specifically disclosed is a compound having a structure wherein constitutional units represented by the general formula (1) below are bonded to one another without the intermediary of a linking group. (1) [In the formula, X1-X4 independently represent an oxygen atom, sulfur atom or NR0 (wherein R0 represents a hydrogen atom or a substituted or unsubstituted monovalent organic group); Z0 represents a tetravalent organic group; and * represents a bonding position.

Description

technical field [0001] The present invention relates to a novel compound and an organic electronic device using the compound, and specifically relates to an electrophotographic photoreceptor, an organic transistor, an organic electroluminescent device, and an organic solar cell. Background technique [0002] Recently, organic electronic materials have received attention. Organic electronics refers to new materials that utilize organic materials as semiconductors instead of conventional inorganic materials. In practical electronic devices using organic materials, the use of active functions caused by current flowing through the materials, so-called active devices, is extremely limited. Among them, the most representative example is an electrophotographic photoreceptor. As examples currently being developed, there are organic electroluminescent elements, organic solar cells, organic transistors, and the like. [0003] As organic electronic materials, there are hole transpor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00G03G5/06H01L29/786H01L31/04H01L51/00H05B33/14H05B33/22H01L51/05H01L51/50
CPCB82Y10/00C09K2211/1029H01L51/0061H01L51/0545G03G5/0661G03G5/0646Y10S428/917H01L51/5048H01L51/4246H01L51/0053C07D519/00G03G5/0655H05B33/14G03G5/065H01L51/0046H01L2251/308H01L51/0081Y02E10/549H10K85/211H10K85/621H10K85/636H10K85/324H10K10/466H10K50/14H10K2102/103H10K30/50H10K30/211
Inventor 藤山高广杉本贤一关口未散
Owner MITSUI CHEM INC
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