A tetrahydroquinoline dye, ink and electrowetting display
An electrowetting display, electrowetting display technology, applied in the direction of ink, azo dyes, organic dyes, etc., to achieve the effect of bright colors, high FoM value, and good light resistance
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Embodiment 1
[0040] 1. First, synthesize intermediate A according to the following synthetic reaction formula:
[0041]
[0042] 1) Synthesis of compound 1
[0043] Weigh 3.0g of m-acetamidoaniline (150g / mol, 0.02mol) and dissolve it in 20mL of 2-octanone, add 0.344g of p-toluenesulfonic acid (172g / mol, 0.002mol), heat up to 110°C for 8 hours, after the reaction is completed The solvent was distilled off under reduced pressure to obtain the product. The product is purified by column chromatography, and the eluent is isopropanol / petroleum ether to obtain compound 1, whose structural formula is Yield 86%.
[0044] 2) Synthesis of Compound 2
[0045] Weigh 5.0 g of the compound 1 (370 g / mol, 0.0135 mol) and dissolve it in 20 mL of toluene, put the solution in an autoclave, add 0.25 g of Pd-C catalyst, pass in 3.5 MPa of hydrogen, and heat up to 130 ° C, Reaction 2h. After the reaction is completed, the catalyst is recovered by filtration, and the solvent is removed by rotary evaporat...
Embodiment 2
[0059] Synthesize the intermediate A according to the same steps as in Example 1, then use the intermediate A to synthesize the dye 2 according to the following synthesis reaction formula:
[0060]
[0061] 1) Diazotization of 2,4-dinitroaniline
[0062] Weigh 2.7g (183g / mol, 0.015mol) of 2,4-dinitroaniline and dissolve it in 50mL of concentrated phosphoric acid, cool to -10~-5°C, add 5.5g of nitrosylsulfuric acid (40%wt), weigh Nitriding 2h.
[0063] 2) Synthetic Dye 2
[0064] Weigh 5.12g of Intermediate A (512g / mol, 0.01mol) and dissolve it in 30mL of acetone, cool to 0-5°C, slowly add the above-mentioned 2,4-dinitroaniline diazonium salt into the above-mentioned coupling components , reacted for 3h, the product was poured into 300mL water to precipitate, extracted with ethyl acetate, and the solvent was removed by rotary evaporation to obtain 5.6g of the dye 2 product, the structural formula of the dye 2 was Structural characterization after column separation, its m...
Embodiment 3
[0066] Synthesize the intermediate A according to the same steps as in Example 1, and then use the intermediate A to synthesize the dye 3 according to the following synthesis reaction formula:
[0067]
[0068] 1) Diazotization of 2-aminobenzothiazole
[0069] Dissolve 2-aminobenzothiazole in concentrated phosphoric acid, cool to -10~-5°C, add nitrosyl sulfuric acid (40%wt), and diazotize for 2h.
[0070] 2) Synthetic Dye 3
[0071] Take intermediate A (512g / mol, 0.01mol) and dissolve it in acetone, cool to 0-5°C, slowly add the above-mentioned 2-aminobenzothiazole diazonium salt to the above-mentioned coupling component, react for 3h, and the product Pour into water to precipitate, extract with ethyl acetate, and remove the solvent by rotary evaporation to obtain the dye 3 product, the structural formula of the dye 3 is 1 g of the obtained dye 3 was dissolved in 5 g of n-tetradecane to obtain an electrowetting ink material M-3.
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