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Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof

A room-temperature phosphorescent and optical material technology, applied in luminescent materials, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of heavy metals such as expensive, not environmentally friendly, and toxic, and achieve low toxicity, low cost, and easy synthesis.

Active Publication Date: 2017-04-19
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since heavy metals are often expensive, highly toxic, and not environmentally friendly, both academia and industry are eager to develop purely organic room-temperature phosphorescent materials free of heavy metal atoms.

Method used

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  • Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof
  • Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof
  • Pure organic room-temperature phosphorescent material, preparation method thereof and application thereof

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preparation example Construction

[0054] The present application also provides a preparation method of the pure organic room temperature phosphorescent material, comprising the following steps:

[0055] With the compound of formula (Ⅲ) structure and NH 2 R is reacted in a solvent, and after separation, a pure organic room-temperature phosphorescent material having a structure of formula (I) is obtained;

[0056]

[0057] Wherein, R is a pure organic electron-donating group;

[0058] R 1 with R 2 Same, selected from pure organic electron-donating groups;

[0059] x 1 、X 2 、X 3 with X 4 Each is independently selected from H, Cl, Br or I.

[0060] The above preparation process prepares a pure organic room temperature phosphorescent material with the structure of formula (I) or formula (II), wherein when preparing the organic phosphorescent material with the structure of formula (II), the R 1 with R 2 Same, since the reactant with the structure of formula (Ⅲ) and NH 2 The molar ratio of R to the reac...

Embodiment 1

[0078] The synthesis of embodiment 1 naphthalimide derivative N1

[0079] In a 100ml round bottom flask, add 1,4,5,8-naphthalene tetracarboxylic anhydride (0.8g, 3mmol), p-methoxyaniline (0.37g, 3mmol) and 25ml absolute ethanol successively, and the mixture is under a nitrogen atmosphere Heating and reflux reaction for 2 hours, after the completion of the reaction, let it stand and cool to room temperature, filter the obtained solid and purify it by silica gel column chromatography, the eluent is ethyl acetate / n-hexane volume ratio 1 / 2, to obtain pure naphthalimide derivative N1 , light yellow powder, yield 92%. The hydrogen spectrum detection result is: 1 H NMR (DMSO-d 6 )δ (ppm): 3.85 (s, 3H), 7.10 (d, 2H, J = 8.8Hz), 7.36 (d, 2H, J = 8.8Hz), 8.62 (s, 2H), 8.74 (s, 2H) .

[0080] Mix N1 and PMMA at a mass ratio of 1 to 10,000 to form a film. In a pure nitrogen atmosphere, when irradiated by a 365nm ultraviolet lamp, there is red room temperature phosphorescence, such as ...

Embodiment 2

[0081] The synthesis of embodiment 2 naphthalimide derivatives N2

[0082] Replace the p-methoxyaniline in embodiment 1 with p-dimethylaminoaniline, and the others are the same as in embodiment 1. The result of the experiment is that a light yellow powder was obtained in this example, and the yield was 91% of the compound. The hydrogen spectrum detection result is: 1 H NMR (DMSO-d 6 )δ (ppm): 4.15 (s, 6H), 7.12 (d, 2H, J = 8.8Hz), 7.31 (d, 2H, J = 8.8Hz), 8.61 (s, 2H), 8.73 (s, 2H) .

[0083] Mix N2 and PMMA at a mass ratio of 1 to 10,000 to form a film. In a pure nitrogen atmosphere, when irradiated by a 365nm ultraviolet lamp, there is red room temperature phosphorescence, such as figure 1 as shown, figure 1 is the photoluminescence spectrum of compounds N1-N5 under pure nitrogen atmosphere, from figure 1 It can be seen that the emission peaks are at 612nm and 671nm, the phosphorescence lifetime is 131ms, and the quantum yield is 5.3%.

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Abstract

The invention provides a pure organic room-temperature phosphorescent material with a structure as shown in formula (I) or formula (II), and also provides a preparation method for the pure organic room-temperature phosphorescent material with the structure as shown in formula (I) or formula (II). The invention discloses a series of pure organic room-temperature phosphorescent materials based on a naphthalimide derivative. The pure organic room-temperature phosphorescent materials are characterized in that pure organic electron-donating groups are introduced into molecules, so that the molecules are excited by an outside light source to generate a charge transfer state (ICT) in the molecules, and ICT can promote intersystem crossing, so that generation of room-temperature phosphorescence is facilitated. The pure organic phosphorescent material provided by the invention has the advantages of being simple and convenient to synthesize, low in cost, easy to chemically modify, low in toxicity, environmentally friendly and the like.

Description

technical field [0001] The invention relates to the technical field of organic materials, in particular to a pure organic room temperature phosphorescent material, its preparation method and its application. Background technique [0002] Compared with fluorescent materials, room temperature phosphorescent materials have many unique advantages, and have broader practical application prospects in the fields of biological imaging, chemical sensing, and optoelectronic display. For example, compared with fluorescent materials, phosphorescent materials have a larger Stokes shift and a longer lifetime, which can avoid the interference of excitation light source, background, and impurity fluorescence in biological imaging applications; Quenchers and other factors are very sensitive, so they are widely used in sensing and detection fields such as oxygen; phosphorescent materials use triplet excited states, and quantum calculations show that triplet excited states are three times the ...

Claims

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Application Information

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IPC IPC(8): C07D491/06C07D471/06C08G63/08C09K11/06G01N21/64
Inventor 张国庆张学鹏杜嘉俊
Owner UNIV OF SCI & TECH OF CHINA
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