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Organic room-temperature phosphorescent material as well as preparation method and application thereof

A room temperature phosphorescent and phosphorescent material technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of difficult information erasure, difficult to meet application requirements, unable to apply solid or gel materials, etc. Anti-counterfeiting and display scene requirements, low cost, strong machinability

Pending Publication Date: 2021-02-05
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this system, the phosphorescence generation depends on the choice of solvent molecules and cannot be applied to solid or gel materials.
However, directly synthesized polymer phosphorescent materials are difficult to erase information, which is usually achieved by re-dissolving, which is obviously difficult to meet the needs of a wider range of applications.

Method used

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  • Organic room-temperature phosphorescent material as well as preparation method and application thereof
  • Organic room-temperature phosphorescent material as well as preparation method and application thereof
  • Organic room-temperature phosphorescent material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] An organic room-temperature phosphorescent material, said phosphorescent material comprising any one of the phosphorescent materials represented by formula (I), formula (II), and formula (III);

[0065]

[0066] Further, formula (I) is obtained by coupling reaction of phenothiazine and monohalogenated benzene; formula (II) is obtained by coupling reaction of phenothiazine and p-substituted halogenated benzene; formula (III) is obtained by coupling reaction of phenothiazine and 1,3,5-substituted halogenated benzene coupling reaction.

[0067] in:

[0068] The structural formula of phenothiazine is (a);

[0069] The structural formula of monohalogenated benzene is (b);

[0070] The structural formula of p-substituted halobenzene is (c);

[0071] The structural formula of 1,3,5-substituted halobenzene is (d);

[0072] In the formula, R=Br, I; R 1 =Br,I;R 2 =Br,I;R 3 =Br,I.

[0073] Further, in formula (I), the ratio of the amount of phenothiazine to mono...

Embodiment 2

[0075] A preparation method of the organic room temperature phosphorescent material described in embodiment 1, comprising the following steps:

[0076] S1, under nitrogen protection state, get 1.99g (10mmol) phenothiazine, 2.04g (10mmol) iodobenzene, 1.68g (15mmol) potassium tert-butoxide (t-BuOK), 0.11g (0.5mmol) palladium acetate ( Pd(OAc) 2 ) and 0.25mL (0.25mmol) tri-tert-butylphosphine (P(t-Bu) 3 ) was dissolved in 90mL of toluene solution, heated to reflux for 24 hours. Cool to room temperature, heat and evaporate to remove the solvent, extract three times with dichloromethane, add anhydrous magnesium sulfate to the organic phase and dry. The crude product was obtained by filtration, and then purified by column chromatography to obtain the product of formula (I), the product quality was 2.6 g, and the yield was 94.5%. Concrete preparation reaction formula is:

[0077]

[0078] S2, get 1.0 mg of the formula (I) product obtained in S1 and 100 mg of polymethyl methac...

Embodiment 3

[0087] A preparation method of the organic room temperature phosphorescent material described in embodiment 1, comprising the following steps:

[0088] S1. Under nitrogen protection, take 3.98g (20mmol) phenothiazine, 2.81g (10mmol) p-bromoiodobenzene, 2.88g (30mmol) sodium tert-butoxide (t-BuONa), 0.11g (0.5mmol) acetic acid Palladium (Pd(OAc) 2 ) and 0.25mL (0.25mmol) tri-tert-butylphosphine (P(t-Bu) 3 ) was dissolved in 120mL of toluene solution, heated to reflux for 24 hours. Cool to room temperature, heat and evaporate to remove the solvent, extract three times with dichloromethane, add anhydrous magnesium sulfate to the organic phase and dry. The crude product was obtained by filtration, and then purified by column chromatography to obtain the product of formula (II), with a product quality of 3.8 g and a yield of 80.9%. Concrete preparation reaction formula is:

[0089]

[0090]S2, take 0.5 mg of the formula (I) product obtained in S1 and 100 mg of polymethyl met...

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Abstract

The invention discloses an organic room-temperature phosphorescent material as well as a preparation method and application thereof. The structure of the phosphorescent material is shown as a formula(I), a formula (II) or a formula (III). The molecules all contain one or more phenothiazine units, and when the molecules are dispersed and immobilized in a rigid matrix PMMA, the material doped withthe molecules can be induced to generate room-temperature phosphorescence under the excitation of an ultraviolet lamp. Phenothiazine derivative molecules promote oxygen molecules in a matrix materialto be converted into singlet oxygen in the light induction process, and after the oxygen molecules are greatly consumed, the phenothiazine derivative molecules emit phosphorescence due to the fact that non-radiative energy dissipation is inhibited by a rigid environment provided by the matrix. The activated material can be inactivated again by heating or standing for a long time, and the process can be carried out repeatedly. The molecules in the invention can realize light-induced information writing and erasing in a transparent polymer matrix material, material support is provided for organic light information storage, reading and writing, and the practicability is extremely high.

Description

technical field [0001] The invention relates to the field of room temperature phosphorescent materials, in particular to an organic room temperature phosphorescent material and its preparation method and application. Background technique [0002] Phosphorescent materials are widely used in daily life. Since the generation of phosphorescence depends on the small probability transition of triplet excitons in quantum mechanics, such materials often exhibit a long luminescence lifetime compared with fluorescence. For example, emergency signal lights and a series of luminous products take advantage of the long-life characteristics of phosphorescence. It also has high application value in biological imaging, anti-counterfeiting encryption and optical storage. However, these applications are currently based on inorganic phosphorescent materials, especially represented by rare earth-activated aluminate phosphorescent materials. However, such materials have disadvantages such as hi...

Claims

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Application Information

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IPC IPC(8): C07D279/22C09K11/02C09K11/06
CPCC07D279/22C09K11/06C09K11/025C09K2211/1037
Inventor 李振王雲生杨杰方曼曼
Owner TIANJIN UNIV
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