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Naphthalimide organic dye, electrowetting display ink and electrowetting display

An electrowetting display and naphthalimide technology, applied in naphthalene dicarboxamide dyes/phthalimide dyes, inks, organic chemistry, etc., can solve the problems of improving energy consumption of display devices, low display contrast, and poor visual experience and other problems, to achieve the effect of excellent contrast, high solubility, and good visual experience

Active Publication Date: 2021-02-09
SHENZHEN GUOHUA OPTOELECTRONICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This working principle determines that the brightness of existing electrowetting display devices is completely dependent on ambient light, resulting in low display contrast and poor visual experience under low-brightness external ambient light. At this time, it is necessary to use a front light source to improve its Display Brightness and Contrast
However, the application of the front light source will greatly increase the energy consumption of the display device, so its application is subject to certain limitations.

Method used

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  • Naphthalimide organic dye, electrowetting display ink and electrowetting display
  • Naphthalimide organic dye, electrowetting display ink and electrowetting display
  • Naphthalimide organic dye, electrowetting display ink and electrowetting display

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Weigh 2.0g (7.22mmol, 277g / mol) 4-bromo-1,8-naphthoic anhydride Add it into a 50ml round bottom flask, measure 40ml of absolute ethanol as the reaction solvent, and heat up to 50 degrees Celsius. Weigh 3.7g (187g / mol, 0.02mol) 3-(2-ethylhexyloxy) propylamine Continue the reaction for 8h, remove the solvent by rotary evaporation, and pass through the column to obtain 3.08g colorless oily intermediate 1 Yield 95.6%.

[0031] Weigh 1.5g (446g / mol, 0.00336mol) intermediate 1 Dissolve in 30ml ethylene glycol methyl ether, pipette 2ml piperidine The temperature was raised to 125 degrees Celsius to continue the reaction for 12 hours. 1.2g of yellow-green dye 1 was obtained through the column, (Dye-1), yield 80%.

[0032] NMR characterization data: 1 H NMR (400MHz, CDCl 3 ):δ=8.558-8.546(d, J=4.8Hz, 1H), δ=8.485-8.471(d, J=5.6Hz, 1H), δ=8.380-8.366(d, J=5.6Hz, 1H), 7.669-7.643(t, J=10.4Hz, 1H), 7.167-7.151(d, J=6.4Hz, 1H), 4.272-4.243(t, J=11.6Hz, 2H), 3.550-3.52...

Embodiment 2

[0034] Weigh 2.0g (7.22mmol, 277g / mol) 4-bromo-1,8-naphthoic anhydride Add it into a 50ml round bottom flask, measure 40ml diethylene glycol butyl ether as the reaction solvent, and heat up to 120 degrees Celsius. Weigh 7.4g (187g / mol, 0.04mol) 3-(2-ethylhexyloxy) propylamine The reaction was continued for 8h, the solvent was removed by rotary evaporation, and 4.2g of yellow-green dye 2 was passed through the column, (Dye-2), yield 75.6%.

[0035] NMR spectrum characterization data: 1 H NMR (400MHz, CDCl 3 ):δ=8.567(m,1H),8.429(m,1H),8.067(m,1H),7.525(m,1H),6.640(m,1H),6.465(m,1H),4.264-4.253( d, J=4.4Hz, 2H), 3.703(s, 2H), 3.554-3.508(d, J=18.4Hz, 4H), 3.389(s, 2H), 3.287(s, 2H), 2.098(s, 2H ),2.031(s,2H),1.439(s,2H),1.266(m,16H),0.905(m,12H). 13 C NMR (400MHz, CDCl 3 ):164.756,164.184,149.922, 134.612,130.996,129.829,126.327,124.327,123.064,120.318,103.753,74.764,73.747,71.247, 69.250,43.458,39.895,39.641,37.781,30.561,29.113,28.453,23.857,23.070, 14.127, 11.058. ...

Embodiment 3

[0037] Weigh 2.77g (0.01mmol, 277g / mol) 4-bromo-1,8-naphthoic anhydride Add it into a 50ml round bottom flask, measure 40ml of glacial acetic acid as the reaction solvent, and heat up to 50 degrees Celsius. Weigh 4.47g (149g / mol, 0.03mol) p-n-butylaniline The temperature was raised to reflux for 12 hours, the solvent was removed by rotary evaporation, and 2.5 g of colorless oily intermediate 1 was obtained by passing through the column. Yield 62.5%.

[0038] Weigh 1.5g (408g / mol, 0.00367mol) of intermediate 1, dissolve in 30ml of ethylene glycol methyl ether, pipette 2ml of piperidine Added to the above reaction solution, raised the temperature to reflux for 24h, passed through the column to obtain 1.2g of yellow dye 2, (Dye-3), yield 83%.

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Abstract

The invention discloses a naphthalimide organic dye, an electrowetting display ink and an electrowetting display. The chemical structural general formula of the naphthalimide organic dye is as shown in (I), wherein R1 is selected from C4-C20 substituted or unsubstituted alkyl, oxaalkyl and alkylphenyl, X is selected from N and NH, and R2 is selected from C4-C20 substituted or unsubstituted alkyl,alicyclic group, phenyl, alkyl phenyl and oxaalkyl. The naphthalimide organic dye used in the invention has good fluorescence emission performance, has high solubility in a non-polar solvent, and canbe effectively applied to an electrowetting display device to prepare the electrowetting display device with high brightness.

Description

technical field [0001] The invention relates to the field of electrowetting display, in particular to naphthalimide organic dyes, electrowetting display ink and electrowetting display. 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. Different from the traditional electrophoretic electronic paper display technology, which adopts the display principle of black-white particles migrating under the electric field, this 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: in the future When a voltage is applied, the ink wets the insulating layer evenly to form a colored pixel point; when a voltage is applied, the effect of the electric field...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09B57/08C09D11/03C09K11/06G02B26/00
CPCC07D221/14C09K11/06C09B57/08C09D11/03G02B26/005C09K2211/1029
Inventor 邓勇叶德超周国富
Owner SHENZHEN GUOHUA OPTOELECTRONICS
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