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Cathodic electrochromic compound used in electrochromic device, and preparation method thereof

An electrochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, instruments, etc., can solve the problems of increasing the extinction coefficient and achieve the effects of increasing the extinction coefficient, excellent resistance to ultraviolet radiation, and reducing light transmittance

Inactive Publication Date: 2017-07-04
NINGBO MI RUO ELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In order to solve the problem that it is difficult to further increase the extinction coefficient in the existing electrochromic technology, the present invention synthesizes a cathodic electrochromic compound, which is a viologen compound containing a pyridine chromophoric group

Method used

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  • Cathodic electrochromic compound used in electrochromic device, and preparation method thereof
  • Cathodic electrochromic compound used in electrochromic device, and preparation method thereof
  • Cathodic electrochromic compound used in electrochromic device, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] (1) synthesize the cathodic electrochromic compound of following structural formula:

[0046]

[0047] The synthetic route and operation steps are as follows:

[0048]

[0049] Step 1: Disperse sodium hydroxide (20mmol) in polyethylene glycol (200mL) with an average molecular weight of 300g / mol, then add 4-acetylpyridine (20mmol) and benzaldehyde (10mmol) sequentially at 0°C , and react at 0°C for 2h;

[0050] The second step: add ammonium acetate (0.5mol) to the reaction system obtained in the first step, and then incubate at 100° C. for 2 hours, during which precipitation gradually occurs;

[0051] The third step: add deionized water (500 mL) to the reaction system in the second step, and filter to obtain a precipitate. The obtained precipitate was washed with water and a small amount of ethanol in sequence, and dried under vacuum at 50°C for 12 hours to obtain intermediate 4;

[0052] Step 4: Take the intermediate product 4 (4 mmol) and dissolve it in ethano...

Embodiment 2

[0068] (1) synthesize the cathodic electrochromic compound of following structural formula:

[0069]

[0070] The synthetic route and operation steps are as follows:

[0071]

[0072] The first step: under the protection of nitrogen, a n-hexane solution of triethylborane (concentration is 1mol / L, volume is 21mL) is added dropwise to the solution containing 3-lithium pyridine (by butyllithium (21mmol) and 3-bromo Pyridine (21mmol) was prepared by reaction in n-hexane at -5-0°C) in ether solution at -78°C, after the dropwise addition was completed, the reaction was continued at -78°C for 1 h and at room temperature for one night. After the reaction was completed, a solution of iodine (21 mmol) in tetrahydrofuran (20 mL) was added and stirred for 1 h. Afterwards, the above solution was diluted with ethyl acetate and treated with 10% Na 2 S 2 o 3 It was washed with aqueous solution, and the organic phase was collected by static layering and dried with magnesium sulfate. ...

Embodiment 3

[0090] (1) synthesize the cathodic electrochromic compound of following structural formula:

[0091]

[0092] The synthetic route and operation steps are as follows:

[0093]

[0094] The first step: under the protection of nitrogen, a n-hexane solution of triethylborane (concentration is 1mol / L, volume is 21mL) is added dropwise to the solution containing 4-lithium pyridine (by butyllithium (21mmol) and 4-bromo Pyridine (21mmol) was prepared by reaction in n-hexane at -5-0°C) in ether solution at -78°C. After the dropwise addition was completed, the reaction was continued at -78°C for 1 h and at room temperature for one night. After the reaction was completed, a solution of iodine (21 mmol) in tetrahydrofuran (20 mL) was added and stirred for 1 h. Afterwards, the above solution was diluted with ethyl acetate and treated with 10% Na 2 S 2 o 3 It was washed with aqueous solution, and the organic phase was collected by static layering and dried with magnesium sulfate. ...

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Abstract

The structural formula of a cathodic electrochromic compound is shown in the description, a pyridine ring in the middle of the cathodic electrochromic compound is connected to any carbon atom in pyridine rings at two sides through a C-C bond; and in the formula, R1 is selected from C2-20 alkyl groups, R2 to R12 are substituent groups on carbon atoms and are respectively independently selected from H, C1-50 alkyl groups, cycloalkyl groups, polycycloalkyl groups, aryl groups, heterocycloalkyl groups, aralkyl groups and alkaryl groups which are free from or contain halogen, N, O, S, Si, P or an unsaturated bond, and X is selected from a methylbenzenesulfonate anion, a tetrafluoroborate anion, a hexafluoroborate anion, a perchlorate anion, a bisoxalatoborate anion, an oxalyldifluroborate anion, a bis(trifluoromethanesulphonyl)imide anion and a tris(trifluoromethanesulfonyl)methyl anion. An electrochromic device using the compound has a long service life and a deep color, and can greatly reduce the visible light transmittance in the power-up state.

Description

technical field [0001] The present invention relates to a compound used in an electrochromic device and a preparation method thereof, more particularly to a cathodic electrochromic compound used in an electrochromic device and a preparation method thereof. Background technique [0002] Electrochromism is an electric-driven color-changing technology, which is a process in which a material changes its color by gaining and losing electrons under the action of an applied voltage. Usually, this change is between a colorless transparent state and a colored state or between two different colors. This technology has been applied and shows broad application prospects. For example, the electrochromic window on the Boeing aircraft can change the brightness and darkness of the window by pressing the button, thereby adjusting the visual environment in the cabin; the smart window made according to the spectral characteristics of the electrochromic material can selectively transmit solar ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/30C07D213/127C07D213/22C09K9/02G02F1/15
CPCC07D213/127C07D213/22C07D213/30C09K9/02C09K2211/1029G02F1/15G02F2001/15145
Inventor 曹贞虎胡珊珊
Owner NINGBO MI RUO ELECTRONICS TECH CO LTD
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