2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and preparation method thereof

A technology of dimethyl p-benzoquinone, which is applied in the preparation of carboxylic acid nitriles, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of high toxicity, serious environmental pollution, and high risk of raw materials, and achieve easy operation , The effect of simple process

Active Publication Date: 2016-11-23
BEIJING SINEVA TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a preparation method of 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone and the compound, which are used to solve the problems in the existing preparation method. The raw materials used are dangerous, highly toxic, low yield, serious environmental pollution and unsuitable for industrial production.

Method used

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  • 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and preparation method thereof
  • 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and preparation method thereof
  • 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and preparation method thereof

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preparation example Construction

[0032] According to the preparation method of the present invention, the compound that undergoes diazotization reaction with compound A is preferably compound B (dimethylaminoaniline), and other anilines with similar structures, naphthylamine or other condensed ring aromatic amines can also be selected for use. After diazotization Compound D is obtained through a subsequent oxidation step. According to the preparation method of the invention, the process is simple and easy to operate, the yield is as high as over 80%, and the purity can reach over 99%.

[0033] According to one embodiment of the present invention, wherein in the diazotization step S1100, the diazotization reaction of compound A and compound B is: in the presence of nitrite and acid, -20°C to 50°C, more preferably 0 °C to -5 °C, more preferably 0 °C, compound A and compound B undergo a diazotization reaction. The acid is selected from at least one of the following: sulfuric acid, hydrochloric acid and phosphor...

Embodiment 1

[0053] according to figure 1 The schematic flow chart of the preparation method shown, firstly carry out the diazotization step S1100: compound A undergoes a diazotization reaction with compound B to convert compound C; then enters the reduction step S1200: compound C is reduced and converted to compound D; then enters oxidation Step S1300: Compound D is oxidized and transformed into Compound E; finally enters the condensation step S1400: Compound E undergoes a condensation reaction with propanedicyanide and is transformed into Compound F (2,3,5,6-tetrafluoro-7,7',8 , 8'-tetracyanodimethyl-p-benzoquinone), so far the condensation step S1400 ends, and the preparation method is completed.

[0054] The specific operation of the diazotization step S1100 is as follows: 1eq compound A is dissolved in sulfuric acid aqueous solution containing 5eq sulfuric acid, the mass percentage of sulfuric acid aqueous solution is 70%; Sodium nitrate, stirred vigorously at this temperature for 1....

Embodiment 2

[0059] according to figure 1 In the flow chart of the preparation method shown, the diazotization step S1100 is first performed: compound A undergoes a diazotization reaction with compound B to convert compound C; then enters the reduction step S1200: compound C is reduced and converted to compound D; then enters the oxidation step S1300: Compound D is oxidized and transformed into Compound E; finally enters the condensation step S1400: Compound E undergoes a condensation reaction with propanedicyanide and is transformed into Compound F (2,3,5,6-tetrafluoro-7,7',8, 8'-tetracyanodimethyl-p-benzoquinone), so far the condensation step S1400 ends, and the preparation method is completed.

[0060] The specific operation of the diazotization step is as follows: 1eq compound A is dissolved in sulfuric acid aqueous solution containing 10eq sulfuric acid, the mass percentage of sulfuric acid aqueous solution is 70%; then cool down to -5°C, add 2eq sodium nitrite in batches while stirri...

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Abstract

The invention discloses 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and a preparation method thereof. The preparation method comprises diazotization: carrying out diazotization of a compound A and a compound B to obtain a compound C, reduction: reducing the compound C into a compound D, oxidation: oxidizing the compound D into a compound E, and condensation: condensing the compound E and malononitrile to obtain a compound F, wherein the compound F is 2, 3, 5, 6-tetrafluoro-7, 7', 8, 8'-tetracyanoquinodimethane and the compounds A, B, C, D, E and F are shown in the description. The preparation method has good environmental friendliness and a high yield of 80% or more, is simple and easy and is suitable for industrial production.

Description

technical field [0001] The invention relates to the preparation of organic semiconductor 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 (F4-TCNQ) has been widely used in hole injection layer and transport layer. F4-TCNQ is a typical p-type doping system in organic semiconductors. It has the lowest unoccupied orbital (LUMO), which can capture electrons from the highest occupied orbital (HOMO) of the host material and leave an empty state (ie, holes). It can increase the conductivity of organic semiconductors to about 10-5S / cm, which can be used to improve the injection and transport of holes in organic semiconductors. [0003] At present, the preparation method of F4-TCNQ is only reported to use hexafluorobenzene as raw material, tert-butylpropanedicyanide synthesized from acetone and propanedicyanide as nucleophile...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/10C07C253/30
Inventor 姜坤洪豪志李江涛刘杰
Owner BEIJING SINEVA TECH
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