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Preparation method of phenanthrene compounds

A technology for compounds and phenanthrenes, applied in the field of preparation of phenanthrene compounds, can solve the problems of high cost, complicated preparation methods, long purification and preparation time, etc.

Inactive Publication Date: 2013-10-30
TORAY ADVANCED MATERIALS RES LAB CHINA
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AI Technical Summary

Problems solved by technology

However, the synthesis of 3-(9-phenanthrenyl)phenylboronic acid is to first synthesize borane and then use hydrochloric acid hydrolysis to synthesize boric acid. It also uses silica gel chromatography to purify and prepare, which has the problems of complicated operation, long purification and preparation time, and high cost.

Method used

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  • Preparation method of phenanthrene compounds
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  • Preparation method of phenanthrene compounds

Examples

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Embodiment 1

[0030] (1) Synthesis of 2-(6-(2-naphthyl)) naphthyl borane:

[0031]

[0032] Under nitrogen atmosphere, 2-bromo-6-(2-naphthyl)naphthalene (3.00g, 9.00mmol), bis(pinacolate) diboron (4.80g, 18.9mmol), 1,1′-bis (Diphenylphosphino)ferrocene (163mg), potassium acetate (2.72g), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane Compound (273mg), dimethylsulfoxide (100ml) and tetrahydrofuran (40ml) were heated at 80°C for 2 hours. The reaction mixture was left to cool to room temperature, added water, stirred at room temperature for 0.5 hours, extracted with dichloromethane, the organic layer was dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, and the obtained reaction product was used for the next coupling reaction .

[0033] (2) Synthesis of 9-(3-(6-(2,2'-binaphthyl))phenyl)phenanthrene:

[0034]

[0035] Under nitrogen atmosphere, 9-(3-bromophenyl)phenanthrene (3.05g, 9mmol), 2-(6-(2-naphthyl))napht...

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Abstract

The invention discloses a preparation method of phenanthrenes, which comprises the following step: carrying out coupling reaction on a compound A and a compound B under the action of a palladium catalyst to obtain 9-(3-(6-(2,2'-binaphthyl))phenyl)phenanthrene. According to the method, the binaphthyl borane is prepared by directly carrying out coupling reaction on bromine compound without the purification preparation process. The synthesis method reduces the purification preparation process, shortens the preparation time, has the characteristics of simple preparation method, simple operation and the like, is suitable for preparing 9-(3-(6-(2,2'-binaphthyl))phenyl)phenanthrene, and has important meaning in industrialized popularization.

Description

technical field [0001] The invention relates to a fluorescent material or a phosphorescent host material, in particular to a preparation method of a phenanthrene compound. Background technique [0002] In 1987, C.W.Tang et al. from Kodak Company of the United States used Alq 3 A double-layer organic electroluminescent device was successfully prepared using aromatic diamine as the light-emitting layer and the hole transport layer (Tang C.W., et al. Applied Physics Letters, 1987, 51, 913). In 1990, Burroughes J.H., et al. of the University of Cambridge, UK developed organic polymer light-emitting diodes (Burroughes J.H., et al. Nature, 1990, 347, 5395), and the discovery in the field of small molecules and polymers greatly promoted the development of organic electroluminescence. The development of the field of luminescent technology is on the verge of industrialization. Phosphorescent host materials play an important role as the core components of fluorescent materials that ...

Claims

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Application Information

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IPC IPC(8): C07C15/30C07C1/32C09K11/06
Inventor 金光男石垣刚
Owner TORAY ADVANCED MATERIALS RES LAB CHINA
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