A kind of monoazo dye and its synthesis method and application

A technology for monoazo and dyes, applied in the direction of monoazo dyes, azo dyes, organic dyes, etc., can solve the problem of reducing the solubility of organic dyes, reducing the area of ​​full-color gamut, and increasing the degree of dye conjugation, etc. problems, to achieve the effect of small rigidity, large color gamut area, and improved light stability

Active Publication Date: 2018-10-09
SHENZHEN GUOHUA OPTOELECTRONICS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This structural formula contains two azo groups, and the increase in the number of azo groups leads to an increase in the molecular weight of the dye, which correspondingly reduces the solubility of the organic dye color body in the solvent, so in order to improve the dye in the non-polar solvent The solubility puts forward more stringent requirements on the number and structure of solubilizing groups, which leads to the difficulty and high cost of dye synthesis; at the same time, due to the introduction of the bis-azo structure, the degree of conjugation of the dye is increased, and the dye is Orange yellow, under the color matching system of cyan, magenta, and yellow, it will reduce the full-color gamut area that the electrowetting display can display; in addition, the azo group is a potentially unstable group in the dye structure. The process will lead to chromatic aberration changes and device performance degradation due to the breakage of azo bonds

Method used

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  • A kind of monoazo dye and its synthesis method and application
  • A kind of monoazo dye and its synthesis method and application
  • A kind of monoazo dye and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Synthesis of Dye A

[0065]

[0066] Weigh 6.6g (132g / mol, 0.05mol) of tert-butoxycarbonylhydrazine and dissolve it in 50mL of n-hexane, weigh 6.7g (114g / mol, 0.058mol) of isooctylaldehyde and slowly add it dropwise to the above solution, heat up to reflux reaction 2h. After the reaction was completed, the solvent was evaporated to dryness to obtain compound 11 with a yield of 100%. Cool compound 11 to 0-5°C, weigh 100 mL of 1 mol / L borane tetrahydrofuran solution and slowly add it dropwise into the reaction device. The developer is dichloromethane / petroleum ether=1:1, and react for 2 hours to obtain compound 12.

[0067] Measure 15mL of concentrated hydrochloric acid, slowly add it dropwise to the above solution, heat to reflux after no obvious bubbles, and react for 0.5h. After the reaction was completed, it was cooled, and the precipitated boric acid was removed by suction filtration, and the solution was rotary evaporated to dryness. Compound 13 was obtained w...

Embodiment 2

[0078] Synthesis of Dye B

[0079]

[0080] Weigh 1.29g (129g / mol, 0.01mol) of 2,6-difluoroaniline, dissolve it in 9ml of concentrated hydrochloric acid and 50ml of water, cool to 0-5°C, weigh 0.8g (1.2mol, 69g / mol) of sodium nitrite Dissolve it in 5ml of water, add diazotization for 2 hours at one time, and obtain compound 16. Weigh 2.52g (252g / mol, 0.01mol) of compound 14, dissolve it in 50ml of ethanol, cool to 0-5°C, slowly add diazonium salt 16 dropwise to the above solution, and use aqueous sodium hydroxide solution to control the pH of the solution to 9. After the coupling is completed, filter and dry to obtain dye B.

[0081] After column chromatographic separation, the NMR spectrum is characterized, and the NMR spectrum data is: 1 H NMR (CDCl 3 ): 14.23(s, 1H), 7.224(d, 1H), 6.722(d, 2H), 3.627(m, 2H), 2.553(t, 2H), 1.652(m, 2H), 1.552(m, 1H) , 1.338 (m, 10H), 0.904 (m, 9H).

[0082] The UV-Vis absorption spectrum of dye B is as follows Figure 8 As shown in...

Embodiment 3

[0085] According to the similar synthetic method of Examples 1-2, compound C was prepared using different substrates, and its synthetic route and structural formula are as follows:

[0086]

[0087] Purified by column chromatography and then characterized by proton nuclear magnetic spectrum, the data of proton nuclear magnetic spectrum are 1 H NMR (CDCl 3 ): 14.22(s, 1H), 7.444(d, 2H), 7.512(d, 2H), 3.657(m, 2H), 2.453(t, 2H), 1.662(m, 2H), 1.562(m, 1H) , 1.348(m, 10H), 0.914(m, 9H).

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Abstract

The invention belongs to the field of organic dyestuff and discloses mono-azo dyestuff. The mono-azo dyestuff has the chemical structure of he general formula I, and the chemical structure is shown in the specification, wherein R1 is selected from hydrogen, fluorine, chlorine, nitro, cyano, substituted or non-substituted phenyl and substituted or non-substituted C1-C12 alkyl, R2 and R3 are independently selected from hydrogen, fluorine, chlorine, bromine, nitro, cyano and hydroxy, R4 and R5 are independently selected from substituted or non-substituted phenyl and substituted or non-substituted C1-C12 alkyl. The invention further discloses a synthesis method and application of the mono-azo dyestuff. According to the mono-azo electrowetting display organic dyestuff, the conjugation degree of electrons is reduced, and the larger color gamut area can be shown in the three-primary-color blending process; multiple electron-withdrawing substituent groups are introduced to mono-azo group ortho-positions, the electron cloud density of azo groups is reduced, and the light stability of the azo groups is improved; the mono-azo organic dyestuff has the small molecular weight, small rigidity and higher solubility and saturability; the synthesis process is simpler and low in cost.

Description

technical field [0001] The invention belongs to the field of organic dyes, and in particular relates to a monoazo dye and its synthesis method and application. Background technique [0002] Electrowetting display technology is a display prototype based on electrowetting technology 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 a voltage is applied, the electric field The role of the surface properties of the hydrophobic layer changes the interfacial tension between the three phases of the ink-polar liquid-hydrophobic layer, and the ink is compressed to form transparent or substrate-colored pixels, thereby obtaining the display image effect. [0003] In order to achieve color electrowetting d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B29/46C09D11/03G02B26/00
CPCC09B29/366C09D11/03G02B26/005
Inventor 周国富邓勇蒋洪伟郭媛媛罗伯特·安德鲁·海耶斯
Owner SHENZHEN GUOHUA OPTOELECTRONICS
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