Synthetic method of a class of 9,9'-spirobifluorene derivatives

A technology of spirobifluorene and its derivatives, which is applied in the field of organic chemical synthesis, can solve the problems of 2-bromobiphenyl being expensive, high price, difficult industrial production, etc., and meet the needs of industrial production with low cost and reduced cost Effect

Active Publication Date: 2016-01-20
PUYANG HUICHENG ELECTRONICS MATERIAL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the price of 2-bromobiphenyl in the market is expensive and the supply is insufficient, resulting in the high price of bromo-9,9'-spirobifluorene, which eventually makes 9,9'-spirobifluorene diphenylphosphine derivatives It is difficult to produce industrially, which affects its potential application in luminescent materials

Method used

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  • Synthetic method of a class of 9,9'-spirobifluorene derivatives
  • Synthetic method of a class of 9,9'-spirobifluorene derivatives
  • Synthetic method of a class of 9,9'-spirobifluorene derivatives

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example 1

[0017]

[0018] Under the protection of argon, the reaction temperature was controlled at 100°C, 10 mL of o-bromochlorobenzene (0.1 mmol) in methyl tetrahydrofuran was dropped into 5 mL of phenylmagnesium bromide (0.15 mmol) in methyl tetrahydrofuran, and the reaction was stirred for 20 h. Then the above reaction solution was dropped into 10mL of 2-bromofluorenone (0.1mmol) ether solution, refluxed for 2h, hydrolyzed, filtered, and the solid was reacted in 5mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75°C for 4h, filtered, and the crude solid Using dichloromethane-n-hexane mixed solvent as eluent for column chromatography (200-300 mesh silica gel), 30.0 mg of 2-bromo-9,9'-spirobifluorene was obtained with a yield of 76.0%. The obtained 2-bromo-9,9'-spirobifluorene was reacted with lithium diphenylphosphine (0.075 mmol) in 10 mL of tetrahydrofuran solvent, and after reflux for 5 hours, 10 mL of methanol was added to the reaction solution, and the solid was...

example 2

[0024]

[0025] Under the protection of argon, the reaction temperature was controlled at 80°C, 10 mL of o-dibromobenzene (0.1 mmol) in methyl tetrahydrofuran was dropped into 5 mL of phenylmagnesium bromide (0.11 mmol) in methyl tetrahydrofuran, and the reaction was stirred for 12 h. Then drop the above reaction solution into 10mL of 2,7-dibromofluorenone (0.1mmol) ether solution, heat to reflux for 2h, hydrolyze, filter, react the solid in 5mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75°C for 4h, and filter , the obtained solid was separated by column chromatography (200-300 mesh silica gel) using dichloromethane-n-hexane mixed solvent as eluent to obtain the product 2,7-dibromo-9,9'-spirobifluorene 36.2mg, yield 76.2% . The 2,7-dibromo-9,9'-spirobifluorene obtained above was reacted with lithium diphenylphosphine (0.15 mmol) in tetrahydrofuran solvent, and after reflux for 12 hours, methanol was added to the reaction solution, and a solid was obtained...

example 3

[0031]

[0032] Under the protection of argon, the reaction temperature was controlled at 50°C, 10 mL of o-bromoiodobenzene (0.1 mmol) in methyl tetrahydrofuran was dropped into 5 mL of phenylmagnesium bromide (0.09 mmol) in methyl tetrahydrofuran, and the reaction was stirred for 8 h. Then the above reaction solution was dropped into 5mL of 2-bromofluorenone (0.1mol) ether solution, refluxed for 2h, hydrolyzed, filtered to obtain a solid, reacted in 10mL of mixed acid (glacial acetic acid and hydrochloric acid) at 75°C for 4h, filtered to obtain a solid for use Dichloromethane-n-hexane mixed solvent was used as eluent for column chromatography (200-300 mesh silica gel), and dried to obtain 30.9 mg of 2-bromo-9,9'-spirobifluorene, with a yield of 78.2%. The 2-bromo-9,9'-spirobifluorene obtained above was reacted with lithium diphenylphosphine (0.075 mmol) in 5 mL of tetrahydrofuran, and after reflux for 5 hours, methanol was added to obtain a solid, which was washed with wat...

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Abstract

The invention discloses a synthesis method of a class of 9,9'-spirobifluorene derivatives, which belongs to the field of organic chemical synthesis. Realized by the following method: under the protection of inert gas, use o-bromohalobenzene as raw material in methyl tetrahydrofuran solvent, react with phenylmagnesium bromide at 50-100°C, react with bromofluorenone, and then undergo hydrolysis, Filtration, the solid is closed under acid catalysis to synthesize bromo-9,9'-spirobifluorene; then bromo-9,9'-spirobifluorene reacts with diphenylphosphine lithium to synthesize 9,9'-spirobifluorene Phenylphosphine derivatives. The synthesis method of the invention has simple process, low price and easy availability of raw materials, significantly reduces the production cost of series products in the synthesis process, and expands the application of fluorene derivatives as intermediates in the design and synthesis of organic photoelectric materials.

Description

technical field [0001] The invention relates to a synthesis method of a class of organic phosphine derivatives, in particular to a synthesis method of a class of 9,9'-spirobifluorene derivatives, belonging to the field of organic chemical synthesis. Background technique [0002] Organic electroluminescent materials have the advantages of wide material selection, low energy consumption, high efficiency and luminous brightness, ultra-thin, full curing, fast response, active light emission, and large-area flexible display, etc., and are expected to become the new generation of flat panel display technology. The core component has become one of the research hotspots in the fields of organic electronics and optoelectronic information. Fluorene-based organophosphine derivatives are a class of luminescent materials with broad application prospects. Fluorene has high photothermal stability, the solid-state fluorene fluorescence quantum efficiency is as high as 60%-80%, and the band...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50
Inventor 杨振强杨瑞娜蒋卫鹏周铎冯培培屈凤波
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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