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Multi-chromophoric pyrazolone azo dye, ink and electrowetting display

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, poor light stability, and fast fading speed of dye molecules. problem, achieve the effect of reducing apparent molecular polarity, improving photostability, and low cost

Active Publication Date: 2020-08-14
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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  • Multi-chromophoric pyrazolone azo dye, ink and electrowetting display
  • Multi-chromophoric pyrazolone azo dye, ink and electrowetting display
  • Multi-chromophoric pyrazolone azo dye, ink and electrowetting display

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] This embodiment provides a kind of polychromophore pyrazolone azo dye A, and its synthetic route is

[0027]

[0028] Specifically include the following steps:

[0029] (1) Take 1.37g (137g / mol, 0.01mol) of 4-aminophenylethanol in a round-bottomed flask, add 10mL of water, stir ultrasonically, until it is completely dissolved, dropwise hydrochloric acid (4.17mL, 12mol / L), and cool down To 0-5 ℃, add sodium nitrite (1.5 times, 69g / mol, 1.035g), after forming a homogeneous phase, add a certain amount of urea to remove excess sodium nitrite.

[0030] (2) Take by weighing 3.08g coupler H (structural formula is: ) was dissolved in 20 mL of ethanol to obtain a coupler solution, and the temperature was lowered to 1-5°C. Keep the temperature of the reaction system in step (1) at 0-5°C, add the coupler solution and sodium carbonate lye drop by drop, after the reaction is complete, freeze and crystallize first, add water, and use a mixture of ethyl acetate and petroleum eth...

Embodiment 2

[0036] This embodiment provides a polychromophore pyrazolone azo dye B (i.e. compound B), the structural formula is The synthetic route is the same as in Example 1, except that the number of carbon atoms in the alkyl group of the coupler in this experiment is one more than that in Example 1, and the structural formula of the coupler is:

[0037] Using nuclear magnetic spectrum analysis, the spectral data of compound B are: 1H NMR (CDCl3): 1H NMR (CDCl3): 13.634 (s, 3H) 8.44 (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 spectrogram data proves the structure is correct.

Embodiment 3

[0039] This embodiment provides a polychromophore pyrazolone azo dye C (i.e. compound C), the structural formula is The synthetic route is the same as in Example 1, except that the number of carbon atoms in the substituent group alkyl carbon chain of the coupler in this experiment is 6 less than that in Example 1, and the structural formula of the coupler is:

[0040] Using nuclear magnetic spectrum analysis, the spectrum data of compound C is: 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 spectral data proves that the structure is correct.

[0041] The dye prepared in this example has good light stability and high solubility, and can be dissolved in an organic solvent to prepare an ink. Especially in non-polar organic solvents, such as n-decane, n-dodecane, n-tetradecane, n-hexadecane, fluorine-containing alka...

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PUM

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Abstract

The invention discloses a multi-chromophoric-body pyrazolone azo dye, printing ink and an electrowetting display. The structural general formula of the compound is shown in a formula (I), wherein R1,R2, R3, R4, R5 and R6 are independently selected from substituted or unsubstituted alkyl and substituted or unsubstituted phenyl respectively, the multi-chromophoric-body pyrazolone azo dye can be used for reducing the ink reflux effect and has better light stability, and the formed ink is very suitable for electrowetting display.

Description

technical field [0001] The invention relates to the field of electrowetting displays, in particular to a multi-chromophore pyrazolone azo dye, ink and an electrowetting display. Background technique [0002] Electrowetting display technology (EFD, Electrofluide display), also known as electrowetting display technology, is a display based on the principle of electrowetting display, which was first developed by Philips of the Netherlands in 2003. The display principle of the display is to control the surface properties of the hydrophobic layer by changing the voltage, thereby changing 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 electric field changes the surface properties of the hydrophobic layer, the interfacial tension between the three phases of ink-polar liquid-hydrophobic layer changes, and the ink is compressed to form transparent or substrate-colored ...

Claims

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Application Information

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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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