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Electrochromic compound and application thereof, electrochromic device manufactured by using electrochromic compound and application of electrochromic device

An electrochromic device and electrochromic technology are applied in the field of electrochromic devices and electrochromic compounds, which can solve the problems of short color changing response time and low preparation cost, and achieve wide color changing range and high light transmittance difference. , Improve the effect of radiation resistance and temperature resistance

Active Publication Date: 2018-12-14
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] According to different compositions, electrochromic materials can be divided into inorganic electrochromic materials and organic electrochromic materials. Viologen, also known as viologen, is a typical organic small molecule electrochromic material. Under voltage drive, viologen Viologen-like compounds have good reversible redox reaction performance, and the reaction is accompanied by a significant color change. Viologen-like compounds have the advantages of high color-changing contrast, short color-changing response time, low preparation cost, and long service life. They have been widely studied. Electrochromic compounds, the basic chemical structure of viologen compounds is 1,1'-disubstituent-4,4'-bipyridyl salt, although viologen compounds have a long history of research as electrochromic materials, but , the efforts of the academic community to improve its color-changing properties have not stopped, and new research discoveries are still being published.

Method used

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  • Electrochromic compound and application thereof, electrochromic device manufactured by using electrochromic compound and application of electrochromic device
  • Electrochromic compound and application thereof, electrochromic device manufactured by using electrochromic compound and application of electrochromic device
  • Electrochromic compound and application thereof, electrochromic device manufactured by using electrochromic compound and application of electrochromic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Compound I was prepared by the following steps:

[0056] Step (1), 4-pyridineboronic acid pinacol ester (2.01g, 9.8mmol), tetrakis (triphenylphosphine) palladium (407mg, 0.352mmol), potassium phosphate (5.95g, 28mmol) was added in the 250ml flask, Add 70mL of 1,4-dioxane solution containing 2,5-dibromothiophene (394μL, ρ=2.15mg / mL, 847mg, 3.61mmol) in a nitrogen atmosphere, heat to 90°C, react for 72h, and the reaction is complete After the reaction solution was cooled to room temperature, the filter residue was washed with chloroform, the filtrate was spin-dried in a rotary evaporator, and finally purified by silica gel column chromatography (the eluent was a mixed solution with a mass ratio of chloroform:methanol=200:1) to obtain a yellow solid Namely compound 1 (575mg), yield 69%;

[0057] Step (2), the compound 1 (476mg, 2mmol) obtained in step (1) and diethyl bromoethylphosphate (490mg, 2mmol) were dissolved in 10mL DMF, heated to 90°C, after 24h of reaction, the ...

Embodiment 2

[0066] Compound II was prepared by the following steps:

[0067] Step (1), 3,4-ethylenedioxythiophene (1.42g, 10mmol) was dissolved in 30mL DMF, and cooled to 0°C with an ice bath, N-bromosuccinimide (3.78g, 21mmol) was dissolved In 30mL of DMF, slowly drop into the above solution with a constant pressure dropping funnel. After the dropwise addition, the reaction solution was stirred at room temperature for 2h. After the reaction, 100mL of ice water was slowly added to the reaction solution to produce a large amount of light yellow solid , the product was filtered under reduced pressure, and the filter residue was washed three times with 15 mL of deionized water to obtain 2.85 g of the product, namely compound 4, with a yield of 95%;

[0068] Step (2), 4-pyridineboronic acid pinacol ester (2.01g, 9.8mmol), tetrakis (triphenylphosphine) palladium (407mg, 0.352mmol), potassium phosphate (5.95g, 28mmol) was added in a 250mL flask, Add 70mL of 1,4-dioxane solution containing comp...

Embodiment 3

[0078] The only difference from Example 1 is that compound 8 is used instead of 2,5-dibromothiophene in step (1), and the molar amount of compound 8 added is the same as that of 2,5-dibromothiophene.

[0079] Compound 8 has the following structure:

[0080]

[0081] Embodiment 3 obtains compound III, and compound III has the following structure:

[0082]

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Abstract

The invention provides an electrochromic compound and application thereof, an electrochromic device manufactured by using the electrochromic compound and application of the electrochromic device. According to the electrochromic compound, the conjugated structure of the molecule can be increased by introducing aromatic groups into bipyridine in a conventional viologen compound, so that the stability of the molecule is increased, and the radiation resistance and temperature resistance of the molecular chain are improved; moreover, as growth of the molecular chain and introduction of the aromaticgroups, the redox state of the viologen compound is changed, wherein more abundant color change can be provided for the viologen compound through a redox state rich in chromophore; and the obtained viologen electrochromic compound has a wider discoloration range, higher light transmittance difference values, higher discoloration sensitivity, faster discoloration, low discoloration voltage, and longer service life, and therefore the electrochromic device manufactured by using the electrochromic compound has obvious discoloration performance and cost advantages.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an electrochromic compound, its use, and an electrochromic device prepared by it and its use. Background technique [0002] Electrochromism refers to the phenomenon that the optical properties of materials undergo a stable and reversible color change under the action of an external electric field. It is manifested as a reversible change in color and transparency in appearance. Materials with electrochromic ability are called electrochromic. Materials, devices made of electrochromic materials are called electrochromic devices. The performance of electrochromic devices is closely related to the performance of the electrochromic materials in them. The selection of suitable electrochromic materials can give electrochromic devices color With the advantages of controllable change, large color change range, bistable state and low driving voltage, electrochromic devices have ...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C07F9/6561C09K9/02G02F1/153
CPCC07F9/65586C07F9/6561C09K9/02C09K2211/1029C09K2211/1088C09K2211/1092G02F1/1508G02F1/153
Inventor 苏峰育吴晓文田颜清刘言军罗丹孙小卫
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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