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Naphthalimide organic dyes, electrowetting display inks and electrowetting displays

An electro-wetting display and electro-wetting display technology are applied in the fields of naphthalimide organic dyes, electro-wetting display inks and electro-wetting displays, and can solve the problem of improving energy consumption of display devices, low display contrast, and visual experience. Poor and other problems

Active Publication Date: 2022-06-24
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 dyes, electrowetting display inks and electrowetting displays
  • Naphthalimide organic dyes, electrowetting display inks and electrowetting displays
  • Naphthalimide organic dyes, electrowetting display inks and electrowetting displays

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Weigh 2.0g (7.22mmol, 277g / mol) 4-bromo-1,8-naphthalene acid anhydride Put it into a 50ml round-bottomed flask, measure 40ml of absolute ethanol as a reaction solvent, and heat it up to 50 degrees Celsius. Weigh 3.7g (187g / mol, 0.02mol) 3-(2-ethylhexyloxy)propylamine The reaction was continued for 8h, the solvent was removed by rotary evaporation, and 3.08g of colorless oily intermediate 1 was obtained by passing through the column. Yield 95.6%.

[0031] Weigh 1.5g (446g / mol, 0.00336mol) of Intermediate 1 Dissolve in 30ml ethylene glycol methyl ether, pipette 2ml piperidine The temperature was raised to 125°C and the reaction was continued for 12h. Pass the column to get 1.2g of yellow-green dye 1, (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...

Embodiment 2

[0034] Weigh 2.0g (7.22mmol, 277g / mol) 4-bromo-1,8-naphthalene acid anhydride Put it into a 50ml round-bottomed flask, measure 40ml of diethylene glycol butyl ether as a reaction solvent, and heat it 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 obtained by passing through the column. (Dye-2), yield 75.6%.

[0035] NMR Spectrogram 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....

Embodiment 3

[0037] Weigh 2.77g (0.01mmol, 277g / mol) 4-bromo-1,8-naphthalene acid anhydride Put it into a 50ml round-bottomed flask, measure 40ml of glacial acetic acid as the reaction solvent, and heat it up to 50 degrees Celsius. Weigh 4.47g (149g / mol, 0.03mol) p-n-butylaniline The temperature was raised to reflux for 12h, the solvent was removed by rotary evaporation, and 2.5g 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 it in 30ml ethylene glycol methyl ether, pipette 2ml piperidine was added to the above reaction solution, heated to reflux for 24h, passed through the column to obtain 1.2g of yellow dye 2, (Dye-3), 83% yield.

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Abstract

The invention discloses a naphthalimide organic dye, an electrowetting display ink and an electrowetting display. The general chemical structure formula of the naphthalimide organic dye is shown in (I): wherein, R 1 from C 4 ~C 20 Substituted or unsubstituted alkyl, oxaalkyl, alkylphenyl; X is selected from N, NH; R 2 from C 4 ~C 20 Substituted or unsubstituted alkyl, alicyclic, phenyl, alkylphenyl, oxaalkyl. The naphthalimide organic dyes used in the present invention have good fluorescence emission properties and high solubility in non-polar solvents, and can be effectively applied to electrowetting display devices to prepare electrowetting display devices with high brightness. Wet the display device.

Description

technical field [0001] The present 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 an electric field, 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 a voltage is applied, the ink evenly wets the insulating layer to form a colored pixel; when a voltage is applied, the effect of the electric field changes the s...

Claims

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Application Information

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Patent Type & Authority Patents(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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