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Method for synthesizing N,N'-diphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine

A kind of synthetic method, technology of dimethyl, applied in N field

Inactive Publication Date: 2011-02-16
天津市佰斯康科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in fact, regarding N,N'-bisphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo- The synthesis of 2'-fluorenyl)-benzidine can design multiple routes using any of the above-mentioned methods, but so far there is no N,N'-bisphenyl- The specific synthetic route of N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine

Method used

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  • Method for synthesizing N,N'-diphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine
  • Method for synthesizing N,N'-diphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine
  • Method for synthesizing N,N'-diphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Add 500 grams of 9,9-dimethyl-2-aminofluorene to a 5-liter four-necked bottle, and then add 487.56 grams of iodobenzene, 1500 grams of toluene, 4.56 grams of cuprous iodide, and 4.32 grams of phenanthrene phylloline and 500 grams of potassium carbonate. The above reaction solution was stirred under reflux for 6 hours, cooled to room temperature, filtered, and the filtrate was washed with water until the pH value of the aqueous phase was 7-8. The filtrate organic phase after washing is separated from the aqueous phase, the aqueous phase is discarded, and the organic phase is retained, and then the above-mentioned organic phase is concentrated to dryness using a rotary evaporator to obtain a crude product, and finally the crude product is subjected to silica gel column chromatography (the weight ratio of the crude product to silica gel After recrystallization and purification of 10) and ethyl acetate petroleum ether, 388 g of intermediate 1 (9,9-dimethyl-2-(N-phenyl)-f...

Embodiment 2

[0035] 1) Add 83 grams of 9,9-dimethyl-2-aminofluorene to a four-necked flask, then add 50 grams of iodobenzene, 300 grams of toluene, 0.92 grams of cuprous iodide, 0.87 grams of phenanthroline and carbonic acid Potassium 120 grams. The reaction solution was stirred under reflux for 6 hours, cooled to room temperature, filtered, and the filtrate was washed with water until the pH value of the aqueous phase was 7-8. The filtrate organic phase after washing is separated from the aqueous phase, the aqueous phase is discarded, and the organic phase is retained, and then the above-mentioned organic phase is concentrated to dryness using a rotary evaporator to obtain a crude product, and finally the crude product is subjected to silica gel column chromatography (the weight ratio of the crude product to silica gel 8) was purified by recrystallization from ethyl acetate petroleum ether to obtain 46 g of intermediate 1 (9,9-dimethyl-2-(N-phenyl)-fluorene), with a yield of 65%.

[0036...

Embodiment 3

[0042] 1) Add 70 grams of 9,9-dimethyl-2-aminofluorene to a four-necked flask, then add 35 grams of iodobenzene, 350 grams of toluene, 0.77 grams of cuprous iodide, 0.73 grams of phenanthroline and 130 grams of potassium carbonate. The reaction solution was stirred under reflux for 6 hours. Cool to room temperature, filter, and wash the filtrate with water until the pH of the aqueous phase is 7-8. The filtrate organic phase after washing is separated from the aqueous phase, the aqueous phase is discarded, and the organic phase is retained, and then the above-mentioned organic phase is concentrated to dryness using a rotary evaporator to obtain a crude product, and finally the crude product is subjected to silica gel column chromatography (the weight ratio of the crude product to silica gel 36 g of intermediate 1 (9,9-dimethyl-2-(N-phenyl)-fluorene) was obtained after recrystallization and purification of 6) and ethyl acetate petroleum ether, with a yield of 73%.

[0043] 2) ...

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Abstract

The invention relates to a method for synthesizing N,N'-diphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromine-2'-fluorenyl)-benzidine. In the method, a novel convergent synthesis route is adopted, and 9,9-dimethyl-2-aminofluorene and 9,9-dimethyl-2-bromofluorene are respectively used as starting raw materials for respectively preparing two fragments for synthesizing a final product;and finally, the two fragments are condensed and purified to obtain the final product N,N'-di-phenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9',9'-dimethyl-7'-bromine-2'-fluorenyl)-benzidine. Because the price of the raw materials used by the synthesis method is low, the consumption of a solvent is small and the solvent is easy to recover, the production cost can be greatly reduced on the premise of guaranteeing the product purity and the productivity, thus the method is suitable for industrial production. In addition, the synthesis method has the advantages of simple operation, convenience, safety,and the like.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a kind of N, N'-bisphenyl-N-(9,9-dimethyl-2-fluorenyl)-N'-(9' , The synthetic method of 9'-dimethyl-7'-bromo-2'-fluorenyl)-benzidine. Background technique [0002] Organic Light Emitting Diode (OLED, Organic Light Emitting Diode) material is an organic material that can emit light under the action of an electric field. Compared with the existing light-emitting technology, OLED light-emitting technology has the advantages of low energy consumption, active light emission and the use of planar light sources, etc., so it can be applied to the field of flat-panel displays, so that in addition to the above advantages, flat-panel displays Lighter, thinner, ultra-short response time, ultra-wide viewing angle, high contrast and no interference from external light and many other advantages. OLED light-emitting and display devices are usually multi-layer composite materials, wh...

Claims

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Application Information

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IPC IPC(8): C07C209/10C07C211/61
Inventor 陈晓符新亮袁家龙邱永宽祁功峰
Owner 天津市佰斯康科技有限公司
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