Novel and polymerizable fluorescent dichromatic dye as well as preparation method and purpose thereof

A technology of dichroic dyes and synthesis methods, applied in the field of new fluorescent dichroic dyes and their preparation, can solve the problems of low light transmission efficiency and achieve high quantum efficiency, high dichroic ratio, and high polarized fluorescence effects

Active Publication Date: 2017-11-28
黄山市开发投资集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In the field of displays, the technology used to manufacture operational displays requires the creation of two polarizers, resulting in less than 10% light transmission efficiency

Method used

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  • Novel and polymerizable fluorescent dichromatic dye as well as preparation method and purpose thereof
  • Novel and polymerizable fluorescent dichromatic dye as well as preparation method and purpose thereof
  • Novel and polymerizable fluorescent dichromatic dye as well as preparation method and purpose thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The preparation of novel dichroic dyes, the synthetic route is:

[0037]

[0038] Concrete synthetic steps are as follows:

[0039] 1.1 Preparation of intermediate 1

[0040] Weigh 11.7g of 4,7-dibromo-2,1,3-benzothiadiazole and 15.2g of p-methoxyphenylboronic acid, dissolve in 210mL of 1,4-dioxane, protect under nitrogen environment, and weigh again Take 16.5g K 2 CO 3 Make a 2M aqueous solution and add it to the flask for stirring, then add 3.5g Pd(PPh 3 ) 4 , control the reaction temperature at 103-105°C, reflux reaction for 24h, cool to room temperature after the reaction, and obtain intermediate 1 (9.5g) after suction filtration and vacuum drying, with a yield of 68%;

[0041] 1.2 Preparation of Intermediate 2

[0042] Weigh 4.6g of the intermediate 1 obtained in step (1), add 100mL of hydrobromic acetic acid solution, then add 4.6g of tetra-n-butylammonium bromide, control the reaction temperature at 70°C, reflux for 24h, and cool to At room temperature,...

Embodiment 2

[0048] Quantum Efficiency Test of New Dichroic Dyes

[0049] Use a high-precision balance to accurately weigh 0.00314g of the new dichroic dye, add 5mL of DMF to make a concentration of 10 - 3 mol / L mother solution, use a pipette gun to accurately draw 5 μL of the mother solution and place it in a cuvette, then add 5 mL of DMF to make a concentration of 10 - 6 mol / L dilution. The cuvette was put into the integrating sphere, and the quantum efficiency of the new dichroic dye solution was measured to be 0.82 by a fluorescence spectrometer. The novel dichroic dye powder was placed on the integrating sphere stage, and the quantum efficiency of the novel dichroic dye powder was measured by a fluorescence spectrometer to be 0.85.

Embodiment 3

[0051] Calculation of Molecular Long Axis and Dipole Moment Direction of Novel Dichroic Dye

[0052] Use the Avogadro constant software to draw the three-dimensional configuration diagram of the new dichroic dye molecule and optimize it. The optimized mol file is imported into the GaussView 09 software, and the B3YP / 6-31G unit is used for simulation calculation. The calculated The results show that the molecular long axis of the novel dichroic dye molecules is parallel to the direction of the dipole moment.

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Abstract

The invention discloses novel dichromatic dye as well as a preparation method and a purpose thereof. A material is synthesized by adopting a Suzuki reaction, a hydrolysis reaction and a substitution reaction, is excellent dichromatic dye, has high quantum yield and dichromatic ratio, further, a molecular long axis is parallel to a dipole moment, and has a polymerizable terminal. The novel dichromatic dye can be used for obtaining high-polarization fluorescent light or preparing high-polarization absorption and fluorescent emission films. Thus, the material as well as the preparation method and the purpose thereof have wide application prospects in the fields of display techniques and polarization optics.

Description

technical field [0001] The invention belongs to the field of fluorescent dichroic dyes, and in particular relates to a novel fluorescent dichroic dye and its preparation method and application. Background technique [0002] In the field of displays, the technology used to make operational displays requires the creation of two polarizers, resulting in less than 10% light transmission efficiency. In order to improve the performance of display devices and meet the needs of various environments, it is a natural choice to develop thin-film polarizers with simple structures and high temperature and high humidity resistance. Dichroic dyes with anisotropic absorption of visible light in the long axis and short axis of the molecule have excellent moisture resistance and light resistance, and can be used as polarizing materials. The direction of fluorescence emission of dichroic dye molecules is related to its dipole moment. Therefore, designing and inventing a fluorescent liquid cr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D285/14C09B57/00C09K11/06C08F22/26
CPCC07D285/14C08F22/1006C09B57/00C09K11/06C09K2211/1051C09K2211/1483
Inventor 陆红波沙峻青韦成荆帅诚
Owner 黄山市开发投资集团有限公司
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