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N, N'-diphenyl-N-(9, 9-dimethyl-2-fluorenyl)-N'-(9, 9-dimethyl-7'-(2''-naphthyl)-2'-fluorenyl)-benzidine and synthesis method thereof

A synthesis method and dimethyl technology, applied in the field of chemical synthesis of hole transport materials, can solve problems such as no effective methods have been found yet

Inactive Publication Date: 2011-03-23
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

However, no effective method has been found to solve these problems

Method used

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  • N, N'-diphenyl-N-(9, 9-dimethyl-2-fluorenyl)-N'-(9, 9-dimethyl-7'-(2''-naphthyl)-2'-fluorenyl)-benzidine and synthesis method thereof
  • N, N'-diphenyl-N-(9, 9-dimethyl-2-fluorenyl)-N'-(9, 9-dimethyl-7'-(2''-naphthyl)-2'-fluorenyl)-benzidine and synthesis method thereof
  • N, N'-diphenyl-N-(9, 9-dimethyl-2-fluorenyl)-N'-(9, 9-dimethyl-7'-(2''-naphthyl)-2'-fluorenyl)-benzidine and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] 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 is 1:10) and ethyl acetate / petroleum ether (the weight ratio of the two is 1:80) to obtain 388 grams of intermediate 1 (9,9-dimethyl-2-...

Embodiment 2

[0050] 1) 83 grams of 9,9-dimethyl-2-aminofluorene are added to a four-necked flask, and then 50 grams of iodobenzene, 300 grams of toluene, 0.92 grams of cuprous iodide, 0.87 grams of phenanthroline and 120 grams of potassium carbonate. 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 is 1:8) and ethyl acetate / petroleum ether (the weight ratio of the two is 1:50) to obtain 46 grams of intermediate 1 (9,9-dimethyl-2-(N-phenyl)- Fluorene), the yield ...

Embodiment 3

[0059] 1) 70 grams of 9,9-dimethyl-2-aminofluorene are added to a four-necked flask, and then 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 is 1:6) and ethyl acetate / petroleum ether (the weight ratio of the two is 1:70) to obtain 36 grams of intermediate 1 (9,9-dimethyl-2-(N-phenyl)- Fluorene), the yield is 73%.

[0060...

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Abstract

The invention discloses an N, N'-diphenyl-N-(9, 9-dimethyl-2-fluorenyl)-N'-(9, 9-dimethyl-7'-(2''-naphthyl)-2'-fluorenyl)-benzidine and a synthesis method thereof. The method uses 9, 9-dimethyl-2-acetyl aminofluorene, 9, 9-dimethyl-2-bromine fluorine and 2-bromonaphthalene as starting materials for respectively preparing three segments. Finally, the three segments are respectively processed with a Ullmann condensation reaction and a Suzuki coupling reaction, and then, a final product is obtained through purification. The product prepared by a mode provided by the invention has higher heat stability and lower crystallinity, so that, when the product is used as a hole transmission material, too much holes in a luminescent layer are reduced, and service life of an OLED material can be prolonged. Additionally, a test result shows that purity of the product can be more than 99%, yield is high, and cost is low, so that the product is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis of hole transport materials in organic electroluminescent materials, in particular to a kind of N,N'-bisphenyl-N-(9,9-dimethyl-2-fluorenyl)-N '-(9',9'-dimethyl-7'-(2"-naphthyl)-2'-fluorenyl)-benzidine and its synthesis method. 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, planar light source and wider temperature range, so it can be applied to the field of flat-panel displays, so that flat-panel displays can not only have In addition to the above advantages, it also has many advantages such as lighter, thinner, ultra-short response time, ultra-wide viewing angle, high contrast, and no interferenc...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07C209/68C09K11/06
Inventor 陈晓袁家龙符新亮祁功峰邱永宽
Owner 天津市佰斯康科技有限公司
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