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Novel organic photoconductor molecule and synthetic method thereof

An organic photoconductor and synthesis method technology, applied in the preparation of organic compounds, organic chemistry, semiconductor devices, etc., can solve the problems of high cost, uneconomical practicality, insufficient coverage, etc. The effect of the synthetic route

Inactive Publication Date: 2014-04-02
天津特安化学科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The disadvantage is that many organic compounds with good electron transport ability can be derived from diphenylidine as the nucleus, but this literature only designed and synthesized several molecules with N-phenylcarbazole as the modification group, and the coverage is insufficient.
Catalyst in the synthetic method that adopts: the cost of three (dibenzylidene acetone) dipalladiums is bigger, for enlarging synthetic scale, this method is uneconomical and practical

Method used

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  • Novel organic photoconductor molecule and synthetic method thereof
  • Novel organic photoconductor molecule and synthetic method thereof
  • Novel organic photoconductor molecule and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: Compound (1) N, the synthesis of N'-two (p-ethylphenyl)-N, N'-two (p-hydroxyphenyl) dibenzidine:

[0049] Synthetic roadmap:

[0050]

[0051] 333 g p-ethylaniline, 320 ml 4-methoxybromobenzene, 9 g palladium acetate, 45 g 1,1′-bis(diphenylphosphino)ferrocene (DPPF) and 336 g sodium tert-butyloxide Dissolve in 6.5 liters of dry toluene. The mixture was heated and stirred at 90° C. for 20 hours under the protection of nitrogen. The reaction was monitored by TLC until complete. After filtering and washing with petroleum ether, 530 g of brown product 4-ethyl-N-(p-methoxyphenyl)aniline was obtained. Yield: 93%.

[0052] Second step reaction:

[0053]

[0054] 300 grams of 4-ethyl-N-(p-methoxyphenyl)aniline, 202 grams of 4,,4'-dibromobiphenyl, 7 grams of palladium acetate, 35 grams of 1,1'-bis(diphenylphosphine ) ferrocene (DPPF) and 190 grams of sodium tert-butylate were dissolved in 3 liters of dry toluene. The mixture was heated and stirred at 9...

Embodiment 2

[0058] Embodiment 2: Compound (2) N, the synthesis of N'-two (p-isopropylphenyl)-N, N'-two (p-hydroxyphenyl) dibenzidine:

[0059] Synthetic roadmap:

[0060]

[0061] First step response:

[0062]

[0063] 150 g p-cymene, 128 ml 4-methoxybromobenzene, 3.6 g palladium acetate, 18 g 1,1′-bis(diphenylphosphino)ferrocene (DPPF) and 135 g tert-butyl alcohol Sodium was dissolved in 3 liters of dry toluene. The mixture was heated and stirred at 90° C. for 20 hours under the protection of nitrogen. The reaction was monitored by TLC until complete. After filtering and washing with petroleum ether, 215 grams of brown product 4-isopropyl-N-(p-methoxyphenyl)aniline were obtained. Yield: 89%.

[0064] Second step reaction:

[0065]

[0066] 215 grams of 4-isopropyl-N-(p-methoxyphenyl)aniline, 133 grams of 4,,4'-dibromobiphenyl, 4.8 grams of palladium acetate, 23.8 grams of 1,1'-bis(diphenyl Phosphino)ferrocene (DPPF) and 124 grams of sodium tert-butylate were dissolved in ...

Embodiment 3

[0070] Embodiment 3: Compound (3) N, the synthesis of N'-bis(p-ethylphenyl)-N,N'-bis(p-hydroxymethylphenyl)dianidine: synthetic route map:

[0071]

[0072] 500 g of p-bromobenzyl alcohol were dissolved in 3.5 liters of dichloromethane. After the dropwise addition of 419 g of tert-butyldimethylsilyl chloride, the solution was cooled to 0°C. Then 316 ml of pyridine was added dropwise, keeping the solution temperature at 0°C for at least 20 minutes. Afterwards, the ice bath was removed and the reaction was stirred at room temperature for 5 hours. Monitoring by TLC showed that the reaction of raw material p-bromobenzyl alcohol was complete. Then the mixture was washed with 5% hydrochloric acid (2x1L) and water (2x1L), and dried over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off to obtain 810 g of p-bromobenzyloxy-tert-butyldimethylsilane as an oily product. Yield: 100%.

[0073] Second step reaction:

[0074]

[0075] 340 grams of p-ethylanili...

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Abstract

The invention relates to a novel organic photoconductor molecule and a synthetic method thereof; the reaction adopts dibenzidine as a nucleus, adopts toluene as a solvent, adopts palladium acetate as a catalyst, adopts 1,1'-bis(diphenylphosphino)ferrocene (DPPF) as a ligand, and allows sodium tert-butoxide to react under an alkaline condition. The novel organic photoconductor molecule has a structure as follows.

Description

technical field [0001] The invention relates to the technical field of organic photoconductors, in particular to a class of novel organic photoconductor molecules independently developed and a synthesis method thereof. Background technique [0002] EP1661888A1 published in Europe mainly introduces several diphenylidine derivatives containing N-phenylcarbazole groups and their synthesis methods. These compounds have good electrical properties and electron transport capabilities, and can be used as hole transport materials in fluorescent device. [0003] The molecular structure is as follows: [0004] [0005] The general synthesis method is as follows: [0006] [0007] Give an example to illustrate the above-mentioned synthetic route and reaction route, as follows: [0008] [0009] This material mainly designs several molecules with bis-benzidine as the core and N-phenylcarbazole as the modification group. The core reaction of the synthesis uses toluene as the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C215/82C07C215/68C07C213/00C09K11/06H01L51/54
Inventor 来庚腾飞刘杨祝士忠李茜
Owner 天津特安化学科技有限公司
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