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Dyes, inks and electrowetting display devices based on diketopyrrolopyrrole precursors

A diketopyrrolopyrrole, electrowetting technology, applied in diketopyrrolopyrrole dyes, inks, organic dyes, etc., can solve the problems of poor photostability, reduced utilization efficiency, poor solubility, etc. Stability and solubility properties, reduced association, improved solubility

Active Publication Date: 2021-12-07
SHENZHEN GUOHUA OPTOELECTRONICS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The single-layer electrowetting color display is realized by using black ink and color filter, but due to the use of the filter, the light utilization efficiency is reduced and the contrast is reduced; while the multi-layer electrowetting color display can use three primary colors ( Cyan, magenta, yellow) are superimposed, with high light utilization efficiency and high contrast
[0004] Existing electrowetting shows that the matrix structure of organic dyes is mainly anthraquinone type (US20130241815A1) and azo type (US8747537B2, WO2012161098A1) organic dyes, which have poor photostability and are difficult to meet the needs of outdoor applications.
The organic pigment matrix has the advantage of good light stability, but most organic pigments lack modifying groups in the molecular structure and have extremely poor solubility, making it difficult to prepare electrowetting display ink materials

Method used

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  • Dyes, inks and electrowetting display devices based on diketopyrrolopyrrole precursors
  • Dyes, inks and electrowetting display devices based on diketopyrrolopyrrole precursors
  • Dyes, inks and electrowetting display devices based on diketopyrrolopyrrole precursors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] This example provides a dye (No. Dye-1) based on a diketopyrrolopyrrole precursor, which is prepared according to the following steps:

[0030] Weigh 3.56g (10mmol, 356g / mol) Pigment Red 254 (structural formula is ), 3.36g (30mmol, 112g / mol) potassium tert-butyl alkoxide, 0.322g (1mmol, 322g / mol) tert-butylammonium bromide were dissolved in 100mL dehydrated acetonitrile, stirred at room temperature for 10min, N 2 Protect. Slowly add 19.2 g of n-octane bromide (100 mmol, 192 g / mol) dropwise, and raise the temperature to 80° C. for 6 h. After the reaction was completed, filter with suction, wash the filter cake with ethyl acetate, collect the filtrate, and dry it by rotary evaporation. Purified by column chromatography and recrystallized from ethanol. 2g product Namely Dye-1, the yield is 34.4%. The structural characterization data are as follows: 7.785-7.771 (d, 4H, J = 5.6); 7.532-7.518 (d, 4H, J = 5.6); 3.758-3.732 (t, 4H, J = 10.4); 1.216 (m, 24H) ; 0.898-0.86...

Embodiment 2

[0032] This example provides a dye (No. Dye-2) based on a diketopyrrolopyrrole precursor, which is prepared according to the following steps:

[0033] Weigh 2.88g (10mmol, 288g / mol) Pigment Red 255 (structural formula is ), 3.36g (30mmol, 112g / mol) potassium tert-butyl alkoxide, 0.322g (1mmol, 322g / mol) tert-butylammonium bromide were dissolved in 100mL dehydrated acetonitrile, stirred at room temperature for 10min, N 2 Protect. 19.2 g of bromoisoctane (100 mmol, 192 g / mol) was added, and the temperature was raised to 80° C. for 6 h. After the reaction was completed, filter with suction, wash the filter cake with ethyl acetate, collect the filtrate, and dry it by rotary evaporation. Purified by column chromatography and recrystallized from ethanol. 1.5 g of product was obtained Namely Dye-2, the yield is 29.4%. The structural characterization data are as follows: 7.632-7.618 (d, 4H, J = 5.6); 7.452-7.438 (d, 4H, J = 5.6); 3.568-3.542 (t, 4H, J = 10.4); 2.132 (m, 2H) ; ...

Embodiment 3

[0035] This example provides a dye (No. Dye-3) based on a diketopyrrolopyrrole precursor, which is prepared according to the following steps:

[0036] Weigh 3.56g (10mmol, 356g / mol) Pigment Red 254, 3.36g (30mmol, 112g / mol) potassium tert-butyl alkoxide, 0.322g (1mmol, 322g / mol) tert-butylammonium bromide dissolved in 100mL dehydration in acetonitrile, stirred at room temperature for 10 min, N 2 Protect. Add 30.5 g of bromomethylpentadecane (100 mmol, 305 g / mol), and raise the temperature to 80° C. for 6 h. After the reaction was completed, filter with suction, wash the filter cake with ethyl acetate, collect the filtrate, and dry it by rotary evaporation. Purified by column chromatography and recrystallized from ethanol. 2 g of product were obtained. Namely Dye-3, the yield is 34.4%.

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Abstract

The invention discloses a dye, an ink and an electrowetting display device based on a diketopyrrolopyrrole precursor. The chemical structural formula of the dye is shown in formula (I): wherein, R 1 Selected from hydrogen, chlorine, phenyl, C1-C8 alkyl, cyano; R 2 is an alkyl group. The dye provided by the invention has good photostability and solubility, and has a very high application prospect in the field of electrowetting display.

Description

technical field [0001] The invention relates to the field of electrowetting displays, in particular to dyes, inks and electrowetting display devices based on diketopyrrolopyrrole precursors. Background technique [0002] Electrowetting display technology (EFD, Electrofluide display), also known as electrowetting display technology, is a display prototype based on the principle of electrowetting display first developed by Philips of the Netherlands in 2003. The display principle is to control the surface properties of the hydrophobic layer by changing the voltage, and change the contact angle of the ink layer on the hydrophobic layer: when no voltage is applied, the ink wets the insulating layer evenly to form a colored pixel; when the voltage is applied, The effect of the electric field changes the surface properties of the hydrophobic layer to change the interfacial tension between the three phases of ink-polar liquid-hydrophobic layer, and the ink is compressed to form tra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07D487/04C09B67/20C09D11/03C09D11/328G02B26/00
CPCC07D487/04C09B57/004C09B67/006C09D11/03C09D11/328G02B26/005
Inventor 邓勇叶徳超周国富
Owner SHENZHEN GUOHUA OPTOELECTRONICS