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Benzotriazole compound with diphenol substituted structure as well as preparation and application thereof

A benzotriazole and biphenol-based technology is applied in the application field of ultraviolet-short-wavelength blue light absorbers and organic light absorbing materials, and can solve problems such as visual impairment, killing of active cells in human eyes, and weak blue light absorption ability. , to achieve the effect of eliminating the destructive effect

Inactive Publication Date: 2019-11-01
佛山华铕光电材料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Blue light can directly reach the retina. If you are exposed to a large amount of low-wavelength blue light for a long time, a large number of active cells in the human eye will be killed, causing irreversible damage to vision.
[0003] In particular, it should be emphasized that due to the weak absorption of blue light by the macula of children's retinas, under the same light intensity, the amount of blue light radiation transmitted is about twice that of adults, so blue light radiation is more harmful to children's retinas.

Method used

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  • Benzotriazole compound with diphenol substituted structure as well as preparation and application thereof
  • Benzotriazole compound with diphenol substituted structure as well as preparation and application thereof
  • Benzotriazole compound with diphenol substituted structure as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] This embodiment aims at giving the synthetic method of bromination reaction and the product of bromination reaction.

[0039] Compound: 2-(2'-Hydroxy-3'-bromo-5'-methylphenyl)benzotriazole,

[0040] Synthetic method: In a 100mL round bottom flask, add UV-p(2-(2'-hydroxyl-5'-methylphenyl)benzotriazole 4.50g (20mmol), dichloroethyl alkane 40mL, stir to dissolve; slowly add bromine 3.84g (24mmol) dropwise, and react for 8 hours under stirring at room temperature; introduce the mixture into water, and slowly neutralize it with solid sodium bicarbonate to neutrality; separate the organic layer, The aqueous layer was repeatedly extracted twice with dichloroethane (10 mL); the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation, followed by recrystallization with dichloroethane to obtain 5.59 g of the target product with a yield of 92%. The melting point of the product is 202.4-202.9°C.

[0041] Compound NMR ...

Embodiment 2

[0043]This example uses the product of Example 1 as the reaction raw material, and aims to provide the synthesis method of the coupling reaction and the product of the coupling reaction.

[0044] Compound: 2-(2'-Hydroxy-3'-phenyl-5'-methylphenyl)benzotriazole,

[0045] Synthetic method: Add 2-(2'-hydroxy-3'-bromo-5'-methylphenyl)benzotriazole to a 100mL three-necked bottle filled with a mixture of toluene 40mL, ethanol 8mL and water 16mL 3.03g (10mmol), 1.22g (10mmol) of phenylboronic acid and 5.52g (40mmol) of potassium carbonate were dissolved by magnetic stirring; then nitrogen was vigorously bubbled in the solution for 5min, and 0.3g (0.26 mmol) continue to bubble vigorously in the solution with nitrogen for 5 min; react under nitrogen atmosphere and reflux for 24 hours, after the reaction is complete, cool the reaction mixture to room temperature, separate the organic layer, and repeat the extraction of the aqueous layer with 10 mL of dichloroethane 2 times; combine th...

Embodiment 3

[0048] In this example, the brominated product of Example 1 was used as a raw material for a coupling reaction, and the coupling reaction conditions were the same as in Example 2.

[0049] Compound: 2-(2'-hydroxy-3'-(4-diphenylamino)phenyl-5'-methylphenyl)benzotriazole,

[0050] Synthetic method: Add 3.03g (10mmol) of 2-(2'-hydroxy-3'-bromo-5'-methylphenyl)benzotriazole to a three-necked flask containing a mixture of toluene, ethanol and water , 2.89g (10mmol) of triphenylamine 4-boric acid, and 40mmol of potassium carbonate were dissolved by magnetic stirring; then nitrogen was vigorously bubbled in the solution for 5min, and 0.3g (0.26mmol) of tetrakis(triphenylphosphine) palladium was added to continue to use nitrogen Vigorously bubbling in the solution for 5 min; reflux under nitrogen atmosphere for 24 hours, after the reaction was complete, the reaction mixture was cooled to room temperature, the organic layer was separated, and the aqueous layer was repeatedly extracte...

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Abstract

The invention provides a series of benzotriazole compounds with a diphenol substituted structure, and the general formula of the chemical structure of the benzotriazole compound is [3-(2H-benzo[d][1,2,3]triazole-2-yl)-4',5-disubstituted-[1,1'-biphenyl]-2-phenol], wherein R1 is selected from alkyl, alkoxy, aryl, amino or halogen groups; when R3 is hydrogen, R2 is selected from alkyl, alkoxy, aryl,amino or halogen groups; and when R3 is a methoxy group, R2 is benzene or 4-substituted phenyl. The light absorption main peak of the compound is near 350 nm, and the red shift of the compound is about 10 nm compared with that of a common benzotriazole ultraviolet absorbent, so that the absorption wavelength of the compound is obviously increased, and the maximum coverage range of the absorption wavelength can exceed 420 nm. The compound has the characteristic of absorbing short-wavelength blue light, and can be used as a blue light absorbent.

Description

technical field [0001] The present invention relates to the fields of organic materials and light absorbers, in particular to a new type of ultraviolet-short-wavelength blue light absorber, [3-(2H-benzo[d][1,2,3]triazol-2-yl )-4',5-disubstituted-[1,1'-biphenyl]-2-phenol] and its application as an organic light-absorbing material. Background technique [0002] The wavelength of light visible to human naked eyes is about 400-700nm. 400-500nm is blue light, which has the shortest wavelength and the highest energy among visible light. The most pigmented part of the human eye is the macula, which determines the quality of a person's vision. The research results show that blue light and ultraviolet light are the most unacceptable to the human eye. The ability of blue light to kill the active cells of the human eye is 10 times that of green light. Blue light can reach the retina directly. If you are exposed to a large amount of low-wavelength blue light for a long time, a large...

Claims

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Application Information

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IPC IPC(8): C07D249/20C09K3/00
CPCC07D249/20C09K3/00
Inventor 刘嘉荣宋森川朱国勋梁东史华红
Owner 佛山华铕光电材料股份有限公司
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