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Synthesis method of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane

A dimethyl pair, synthesis method technology, applied in the field of organic electroluminescent materials, can solve the problems of easy occurrence of danger, increase of risk factor, easy volatilization of bromine, etc., and achieve improved safety, low use environment requirements, and stability Good results

Active Publication Date: 2016-11-09
FUYANG XINYIHUA MATERIAL TECH
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Problems solved by technology

[0005] At present, the synthesis method of F4-TCNQ is generally to first synthesize tert-butylmalononitrile with acetone and malononitrile as raw materials, then use hexafluorobenzene as a reaction raw material, and use tert-butylmalononitrile as a nucleophile to hydrogenate Sodium is used as a base to cause a coupling reaction between tert-butylmalononitrile and hexafluorobenzene to obtain an intermediate to remove the tert-butyl group, and finally use bromine to remove the α-H on the methylene connected to the cyano group to obtain Final product F4-TCNQ (referring to J.Org.Chem., Vol.40, No.21,1975 3101); But, this synthetic method needs just can obtain F4-TCNQ through four-step reaction, makes synthetic method complicated, and the used Sodium hydride has relatively high requirements on the use environment. If the use environment has high humidity, it is very prone to danger, which greatly increases the risk factor of F4-TCNQ in the amplification reaction, and bromine is volatile and highly toxic, which not only increases The risk factor of synthetic operation has been reduced, and, because in post-treatment process, need use a large amount of water to remove the excess bromine that contains in the F4-TCNQ crude product, therefore, more waste water in post-treatment process

Method used

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  • Synthesis method of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane

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preparation example Construction

[0040] The synthesis method of 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone provided in the examples of the present invention includes:

[0041] The first step is to use 2,3,5,6-tetrafluoroterephthaloyl chloride and trialkylsilyl cyanide as raw materials, and use an organic base as a catalyst to carry out condensation reaction under anhydrous and oxygen-free conditions to obtain an intermediate; The chemical structure general formula of described intermediate is:

[0042]

[0043] Among them, R 1 , R 2 , R 3 , R 4 is an alkyl group;

[0044] In the second step, the trialkylsiloxy group in the intermediate is removed to obtain 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone.

[0045] In the synthetic method of 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone provided in the examples of the present invention, 2,3,5,6-tetrafluoro Fluoroterephthaloyl dichloride and trialkylsilyl cyanide are used as raw materials, and the 1...

Embodiment 1

[0081] In the first step, mix 1.42mol of 2,3,5,6-tetrafluoroterephthaloyl chloride, 22.5mol of trimethylsilyl cyanide, and 500mL of pyridine, and heat to 80°C under the protection of nitrogen for condensation Reaction, during the condensation reaction, use thin-layer chromatography to monitor the progress of the reaction. The developer used is dichloromethane. The test results on the silica gel plate are displayed by ultraviolet light. A new product point has been found, which proves that the condensation reaction has reached the end point, and the reaction is ended, and then the pyridine and excess trimethylsilyl cyanide are recovered by distillation under reduced pressure, and the obtained intermediate is put into a desiccator and dried at room temperature for 16 hours, and 1.40mol is collected for drying. later intermediates.

[0082] In the second step, after mixing 1.40 mol of intermediates, 14 mol of phosphorus trichloride and 1500 mL of pyridine, the obtained reaction sys...

Embodiment 2

[0084] In the first step, 1.2mol of 2,3,5,6-tetrafluoroterephthaloyl chloride, 24mol of triethylsilyl cyanide, 150mL of toluene, and 300mL of triethylamine were mixed and heated to Condensation reaction was carried out at 110°C. During the condensation reaction, thin-layer chromatography was used to monitor the progress of the reaction. The developer used was dichloromethane. The test results on the silica gel plate were displayed by ultraviolet light. When stirred at 110°C for 8 hours, the ultraviolet light showed A new product point is generated on the silica gel plate, which proves that the condensation reaction has reached the end point, and the reaction is ended, and then the toluene, triethylamine and excess triethyl cyanosilane are recovered by distillation under reduced pressure, and the obtained intermediate is placed in a desiccator at room temperature After drying for 16 h, 1.15 mol of the dried intermediate was collected.

[0085] In the second step, after mixing 1...

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Abstract

The invention discloses a synthesis method of 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane and relates to the technical field of organic electroluminescent materials. On the basis of simplifying the synthesis method, wastewater generated by post-treatment is reduced, and the safety of a synthesis process is improved, so that the synthesis method is applicable to industrial production. The synthesis method comprises the following steps: firstly, carrying out a condensation reaction by taking 2,3,5,6-tetrafluoroterephthaloyl chloride andtrialkylsilyl cyanide as raw materials under an oxygen-free and dry environment to obtain an intermediate; and then, removing trialkylsiloxy in the intermediate to obtain F4-TCNQ. The synthesis method of the 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane, disclosed by the invention, is used for synthesizing organic electroluminescent materials.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence materials, in particular to a synthesis method of 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone. Background technique [0002] 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone is an organic semiconductor material with p-type doping system, and its hole injection in OLED screen It has a wide range of applications in layer and transport layer. The English name of the organic semiconductor material is 2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethylthane, referred to as F4-TCNQ. The chemical molecular structure is as follows: [0003] [0004] Due to the high electron affinity of F4-TCNQ molecule, when it is applied to the hole injection layer and / or transport layer of the OLED screen, it can increase the conductivity of the organic semiconductor to 10S / cm-5S / cm, In order to achieve the purpose of improving the injection and transport of hol...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/35
CPCC07C253/30C07C255/35
Inventor 姜坤
Owner FUYANG XINYIHUA MATERIAL TECH
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