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Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material

A technology of room temperature phosphorescence and thiochroman, which is applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc. It can solve the problems of lack of types of phosphorescent groups, restrictions on the development and application of pure organic room temperature phosphorescent materials, and low phosphorescence quantum yield. , to achieve high absolute phosphorescence quantum yield, stable luminescent properties, and low price

Active Publication Date: 2021-04-20
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the phosphorescent quantum yield of such materials is still not high, and the types of phosphorescent groups are relatively lacking, which restricts the development and application of pure organic room temperature phosphorescent materials.

Method used

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  • Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material
  • Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material
  • Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The guest material of the pure organic room-temperature phosphorescent material provided in this example is thiochromanone, and the host material is polyvinyl alcohol, both of which are directly purchased from a reagent company. The specific steps for preparing pure organic room temperature phosphorescent materials are:

[0029] Weigh 3 mg of thiochromanone and 1000 mg of polyvinyl alcohol and dissolve them in 5 mL of tetrahydrofuran and 30 mL of deionized water, respectively. After complete dissolution, the tetrahydrofuran solution was slowly added dropwise to the aqueous solution under vigorous stirring. After mixing evenly, the solvent was removed by a rotary evaporator, and a colorless transparent film was obtained after drying in a vacuum oven. The film produces bright cyan phosphorescence when excited by 365nm light. The phosphorescence emission intensity of the material does not increase with the irradiation of ultraviolet light. The maximum emission wavelengt...

Embodiment 2

[0031] The room-temperature phosphorescent material provided in this embodiment is compound 3 (having the structure shown in formula I, wherein R is ) as the guest material, with polymethyl methacrylate as the host material, the specific steps for preparing a pure organic room temperature phosphorescent material are:

[0032] The synthetic method of compound 3 is:

[0033]

[0034] (1) Compound 1 (2.9 g, 10 mmol) was added to a mixture of 2M aqueous sodium hydroxide solution (20 mL) and tetrahydrofuran (40 mL). Reflux for 12 hours. After cooling to room temperature, adjusting the pH value to 6, the aqueous layer was extracted with ethyl acetate. The organic layer was concentrated and purified by column to obtain compound 2 (2.4 g). The H NMR spectrum parameters of compound 2 are as follows: 1 H NMR 400MHz, CDCl 3 δ10.15(s,1H),7.491–7.47(m,1H),7.33–7.31(m,2H),3.18–3.15(m,2H),2.70–2.60(m,2H),2.28(s,3H )1.28(s,6H).

[0035] The C NMR spectrum of compound 2: 13 C NMR 1...

Embodiment 3

[0041] Embodiment 3 provides a light-stimulus-responsive room-temperature phosphorescent material and its application in the field of anti-counterfeiting.

[0042] The room temperature phosphorescent material provided in this embodiment includes compound 7 (with the structure shown in formula I, wherein R is F), and polymethyl methacrylate is used as the main material. The specific steps for preparing the room temperature phosphorescent material are:

[0043] The synthetic method of compound 7:

[0044]

[0045] (1) A mixture of compound 4 (1.0 g, 7.8 mmol), compound 5 (1.2 g, 7.8 mmol), potassium carbonate (3.2 g, 23.4 mmol) and acetonitrile was heated to reflux. After reacting for 12 hours, it was cooled to room temperature, and the insoluble matter was filtered off, and the filtrate was concentrated. The obtained crude product was recrystallized from petroleum ether to obtain compound 6 (1.4 g) as a white solid. The proton nuclear magnetic resonance spectrum parameter...

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Abstract

The embodiment of the invention discloses a pure organic room-temperature phosphorescent material based on a thiochromanone derivative as well as a preparation method and application of the pure organic room-temperature phosphorescent material. The organic room-temperature phosphorescent material comprises a host material and a guest material, the guest material is the thiochromanone derivative, and the host material is a polymer such as polyethylene glycol and polymethyl methacrylate. The pure organic room-temperature phosphorescent material is prepared by doping the guest material into the host material by a solvent method. The room-temperature phosphorescent material prepared by the invention is cheap and easily available in raw materials and simple and convenient in preparation method, and the maximum absolute phosphorescent quantum yield can reach 44.0%. The room-temperature material prepared by the invention has the characteristic of photostimulation response, and can be applied to the aspects of photoelectric devices, display materials, information storage materials or anti-counterfeiting materials and the like.

Description

technical field [0001] The present application relates to the technical field of luminescent materials, in particular to a pure organic room temperature phosphorescent material based on thiochromanone derivatives and its preparation method and application. Background technique [0002] Due to its long triplet lifetime, phosphorescent materials allow long-distance migration of excitons, and effectively avoid the interference of short-lived background fluorescence in organisms, they have broad applications in optoelectronic devices, information encryption, anti-counterfeiting, biological imaging and smart materials. application potential. However, since the triplet state of phosphorescent materials is extremely sensitive to temperature and oxygen, the phosphorescent properties of the material can only be observed under low temperature and oxygen-free conditions, which greatly limits its application in various technical fields, so the development of room temperature Phosphores...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D335/06C09K11/06B42D25/387
Inventor 马骧马良伟高昊田禾
Owner EAST CHINA UNIV OF SCI & TECH
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