Multichromophoric pyrazolone azo-based dyes, inks and electrowetting displays

A technology of pyrazolone azo and chromophore, which is applied to the preparation of azo dyes, azo dyes, inks, etc., and can solve the problems of unfavorable electrowetting color development, fast fading speed, and poor light stability of dye molecules. problem, achieve the effect of reducing apparent molecular polarity, reducing ink reflow effect, and improving light stability

Active Publication Date: 2021-05-28
SHENZHEN GUOHUA OPTOELECTRONICS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the current dye molecules are used as electrowetting display inks, due to the existence of certain molecular polarity and dipole moment, it is easy to cause ink reflow effect
In addition, when most dyes exist in the form of single molecules, the photofading reaction is a first-order reaction, and when the dyes exist in the form of aggregation, the photofading reaction is a 0-order reaction, that is, the dyes in the form of single molecules fade quickly. , poor photostability, and dye aggregates fade slowly, but the direct aggregation of dye molecules is not conducive to electrowetting color development

Method used

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  • Multichromophoric pyrazolone azo-based dyes, inks and electrowetting displays
  • Multichromophoric pyrazolone azo-based dyes, inks and electrowetting displays
  • Multichromophoric pyrazolone azo-based dyes, inks and electrowetting displays

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]This embodiment provides a multi-color pyrazolinocardium azo dye A, which synthesis route is

[0027]

[0028]Specifically, the following steps:

[0029](1) Take 1.37 g (137 g / mol, 0.01 mol) 4-amino phenylethyl alcohol in a round bottom flask, add 10 ml of water, ultrasonic stirring, complete hydrochloric acid (4.17 ml, 12 mol / L), cool down To 0-5 ° C, sodium nitrite (1.5 times, 69 g / mol, 1.035 g) was added, and a certain amount of urea was added, and a quantitative urea was added, and the extra sodium nitrite was removed.

[0030](2) Weigh 3.08 g coupling sub-H (structural formula:The coupling agent solution is obtained in 20 ml of ethanol to cool down to 1-5 ° C. Keeping step (1) The reaction system temperature is added to 0-5 ° C, and the coupling sub-solution is added dropwise to the sodium carbonate. After the reaction is complete, the post-treatment is completely frozen crystal, add water, and use acetate with petroleum ether mixed with petroleum ether. Extraction of chromopho...

Embodiment 2

[0036]This embodiment provides a multi-chromorine pyrazolinone coupling dye B (i.e., compound b), structural formulaThe synthesis route is the same as in Example 1, and the difference is that the number of carbon atoms in the alkyl group of the coupling subsequence in this experiment is more than one carbon atom in Example 1, and the structural formula of the coupling sub:

[0037]The spectrum data of Compound B was: 1H NMR (CDCl3): 13.634 (S, 3H): 13.634 (S, 3H): 13.634 (S, 3H): 13.634 (S, 3H), 7.26 (S, 6H), 4.583-4.570 ( M, 6H) 3.705-3.70 (m, 3H), 3.143-3.140 (m, 6H), 2.44 (S, 6H), 1.630-1.625 (m, 12H), 1.540-1.520 (m, 12h), 1.370-1.250 (M, 75H), 0.890-0.880 (M, 18H), the spectrum data certification structure is correct.

Embodiment 3

[0039]This embodiment provides a multi-chromorine pyrazolinoid coupling C (i.e., Compound C), the structural formula isThe synthesis route is the same as in Example 1, and the difference is that the number of carbon atoms in the alkyl carbon chain of the renovial alkyl carbon chain in this experiment is less than 6 in Example 1, and the structural formula of the coupling subscript is:

[0040]Analysis of the nuclear magnetic spectrum, the spectrum data of Compound C was: 1H NMR (CDCl3): 13.794 (S, 3H) 8.739 (S, 3H), 7.398-7.236 (M, 12H), 4.663-4.570 (m, 6H) 3.835-3.785 (m, 3H), 3.343-3.340 (m, 6H), 1.655 (M, 6H), 1.499-1.480 (m, 12H), 1.444 (M, 6H), 1.380-1.244 (m, 9h), 0.890-0.880 (M, 18H), the spectrum data proves the structure correctly.

[0041]The obtained dye light stability is good, and has a very high solubility, and the ink can be prepared in the organic solvent. In particular, in a non-polar organic solvent, such as n-decane, n-dodexecane, n-4alkane, n-hexadecane, fluorine-conta...

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PUM

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Abstract

The invention discloses a multi-chromophoric pyrazolone azo dye, ink and electrowetting display, the general structural formula of which is shown in formula (I): wherein, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 Each independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted phenyl, using the multi-chromophore pyrazolone azo dyes can reduce the ink reflow effect, and has better light stability, forming The ink is very suitable for electrowetting display.

Description

Technical field[0001]The present invention relates to the field of electrowetting displays, in particular, to multi-mass pyrazolinone coupling dyes, inks, and electrowetting displays.Background technique[0002]Electro-wetting display technology (EFD, Electrofluide Display), also known as electrowal removal display technology, the Netherlands Philips, in 2003, in 2003, the above-in-one display. The display principle of the display is to use the change voltage to control the surface properties of the hydrophobic layer, thereby changing the contact angle of the ink layer on the hydrophobic layer: When the voltage is not applied, the ink is uniformly wetted to the insulating layer, forming a colored pixel point; applied voltage At the time, the action of the electric field changes the surface properties of the hydrophobic layer to change the interface tension between the ink-polar liquid-hydrophobic layer three-phase, the ink is compressed, form a transparent or pixel point of the substr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B43/26C09D11/03G02B26/00
CPCC09B43/263C09D11/03G02B26/005
Inventor 邓勇叶德超周莹周国富
Owner SHENZHEN GUOHUA OPTOELECTRONICS
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