Nopinyl β-diketone boron difluoride complex and its preparation method and application

A technology of diketone boron difluoride and nopinyl group, which is applied in the field of nopinyl β-diketone boron difluoride complex and its preparation, and achieves high yield, low price and simple synthesis operation Effect

Inactive Publication Date: 2019-12-06
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In recent years, compounds such as tetraphenylethylenes, siloles, tetraphenyl-1,4-butadiene, 6,13-pentabenzoquinone, and boron fluoride dipyrrole have been widely used in electroluminescent materials. However, there is no report on the synthesis of electroluminescent materials using natural products as raw materials

Method used

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  • Nopinyl β-diketone boron difluoride complex and its preparation method and application
  • Nopinyl β-diketone boron difluoride complex and its preparation method and application
  • Nopinyl β-diketone boron difluoride complex and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0042] 1) Preparation of norpinyl β-diketone

[0043] Add 0.06mol sodium hydride into the reaction vessel, slowly inject 8mL of ethylene glycol dimethyl ether under the protection of nitrogen, dissolve 0.02mol of nopinone in 9mL of ethylene glycol dimethyl ether, slowly inject into the reaction vessel under the protection of nitrogen, and control the reaction by raising the temperature The temperature was 82°C, heated to reflux for 0.5h, 0.024mol of aromatic esters 1a and 1b were dissolved in 9mL of ethylene glycol dimethyl ether, and then slowly injected into the reaction vessel under the protection of nitrogen. The reaction progress was tracked by thin-layer chromatography, and the reaction was carried out for 7-8h. The reactant was extracted three times with 100 mL of ethyl acetate, and the organic phase was concentrated to recover the solvent to obtain the crude product of nopinone β-diketone compound. Recrystallize with methanol, get nopinyl β-diketone 2a and 2b, the stru...

Embodiment 2

[0054] The norpinyl β-diketone boron difluoride complex is used as a light-emitting material in electroluminescent devices.

[0055] 1) Use a 0.001g electronic scale to weigh the conductive adhesive A glue and the curing agent B glue, and the weight ratio is 1:4.

[0056] 2) Conductive adhesive A needs to be stirred for more than 2 minutes before use. Then mix the conductive adhesive A glue with the fluorescent powder and stir well before adding the curing agent B glue. After adding the curing agent B glue, the stirring time generally takes 5 minutes. Make the fluorescent powder and the glue fully mix evenly, then defoam and set aside.

[0057] 3) The debubbled fluorescent glue must be properly stirred before dispensing. It is best to dispensing glue when the bracket is full and the cup is slightly convex, but not overflowing. After drying, the glue can be a flat cup.

[0058] 4) Baking conditions: 60°C / 40min+135°C / 90min. After dispensing, enter the oven for baking immedi...

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Abstract

The invention discloses a nopinyl β-diketone boron difluoride complex, a synthesis method and an application thereof. The present invention uses nopinone, an oxidation product of natural renewable resource β-pinene, as a raw material to prepare novel nopinyl β-diketone boron difluoride complexes 3a and 3b. Nopinone and methyl p-methoxybenzoate 1a and methyl p-bromobenzoate 1b carry out Claisen condensation reaction to prepare nopinyl β-diketone compounds 2a and 2b respectively; compounds 2a and 2b are combined with Boron trifluoride diethyl ether was complexed to prepare nopinyl β-diketone boron difluoride complexes 3a and 3b respectively. The norpinyl β-diketone boron difluoride complexes 3a and 3b have good fluorescence properties and high fluorescence quantum yields, and are used as luminescent materials in electroluminescent devices, which emit blue-green light. It shows that the norpinyl β-diketone boron difluoride complex will have good application value as a light-emitting material in the preparation of electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis and the technical field of novel electroluminescent material synthesis, and relates to a nopinyl β-diketone boron difluoride complex and its preparation method and application. Background technique [0002] As an important class of fluorescent dyes, β-diketone fluoroboron compounds have many optical and structural advantages, such as high fluorescence quantum yield, high electron mobility, and large molar absorptivity, so they are widely used in molecular probes. , optical imaging, solar cells, laser dyes, gels and other fields, and the synthesis of this type of compound has the advantages of simple process, high yield, easy purification, etc., so it has attracted the attention of the majority of scientific researchers. Numerous studies have shown that complete BF 2 It is the basic unit of this type of β-diketone fluoroboron compound, and changing the structure of the aldehyde este...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC09K11/06C07F5/022C09K2211/1096C09K2211/1007H10K85/657
Inventor 杨益琴姜倩王石发徐海军王忠龙谷文徐徐李明新匡洪波杨丽娟张燕
Owner NANJING FORESTRY UNIV
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