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Organic luminescent material and preparation method and application thereof

A luminescent material and organic technology, applied in the field of materials science, can solve the problems of high cost, complex synthesis route, low luminous efficiency, etc., and achieve the effects of fewer synthesis steps, simple synthesis method, high luminous efficiency and luminous intensity

Active Publication Date: 2016-06-22
SHANGHAI UNIVERSITY OF ELECTRIC POWER
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the above-mentioned technical problems in the prior art, the present invention provides an organic light-emitting material and its preparation method and application. The organic light-emitting material and its preparation method and application should solve the organic pressure-induced problems in the prior art. The technical problems of low luminous efficiency, complex synthetic route and high cost of color-changing materials

Method used

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  • Organic luminescent material and preparation method and application thereof
  • Organic luminescent material and preparation method and application thereof
  • Organic luminescent material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 (synthesis of organic luminescent material):

[0041] (1) Synthesis of compound I-1

[0042]

[0043] The specific preparation steps are as described in literature (M. Banerjee, et al., J. Org. Chem., 2007, 72, 8054-8061).

[0044] Diphenylmethane (3.53g, 21.0mmol) was dissolved in 20mL of anhydrous tetrahydrofuran, cooled to 0°C, 1.6M n-butyllithium / n-hexane solution (12.5mL, 20.0mmol) was added dropwise, and after stirring for 30min, the system was Orange red, then cooled to -78°C, a solution composed of 4-bromo-benzophenone (5.22g, 20.0mmol) and 15mL of anhydrous tetrahydrofuran was added dropwise to the system, stirred at -78°C for 3h, and then warmed to room temperature , stirred for 16h. Add 20 mL of saturated ammonium chloride aqueous solution to quench the reaction, let stand to separate layers, extract the aqueous phase with dichloromethane (30 mL×3), wash the combined organic phase with saturated brine (20 mL×2), and add anhydrous magnesium s...

Embodiment 2

[0065] Example 2 (organic luminescent material TPE-NTZ-B piezochromic properties):

[0066] The compound TPE-NTZ-B obtained above was fully ground in an agate mortar, and compared with the unground compound, it was found that its red color became lighter; with 500nm as the excitation wavelength, the solid fluorescence emission spectrum before and after grinding was tested, and the results were as follows figure 1 shown. The maximum emission wavelength of the solid before grinding is located at 623nm, and the maximum emission wavelength of the solid after grinding is blue-shifted to 610nm. It shows that the organic luminescent material has piezochromic performance.

Embodiment 3

[0067] Example 3 (organic luminescent material TPE-NTZ-TPE-1 piezochromic properties):

[0068] The compound TPE-NTZ-TPE-1 obtained above was fully ground in an agate mortar. Compared with the unground compound, it was found that its color changed from orange to red, and the change was very obvious; with 506nm as the excitation wavelength, the test before and after grinding The solid-state fluorescence emission spectrum, the results are as follows figure 2 shown. The maximum emission wavelength of the solid before grinding is located at 598nm, and the maximum emission wavelength of the solid after grinding is red-shifted to 612nm. It shows that the organic luminescent material has piezochromic performance.

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Abstract

The invention provides an organic luminescent material. The structural formula of the organic luminescent material is shown as a general formula (I) (please see the general formula in the description), wherein Ar is selected from aryl or an aromatic heterocyclic group, and R1, R2 and R3 are selected from H and C1-C12 alkyl respectively. The invention further provides a preparation method of the luminescent material. A tetraphenylethylene derivative unit and the aryl (or the heterocyclic group) are introduced into a molecule by taking naphthothiadiazole as a core unit. According to the organic luminescent material and the preparation method thereof, the organic luminescent material can generate changes of solid colors and fluorescence under the pressure action, and the piezochromic property has the very important effect in the optoelectronic field.

Description

technical field [0001] The invention belongs to the field of materials science, and relates to an organic luminescent material, specifically a luminescent material containing naphtho[2,3-c][1,2,5]thiadiazole and tetraphenylethylene structures and its Preparation methods and applications. Background technique [0002] Piezochromism refers to a phenomenon in which the color of a material, especially the fluorescence (such as luminous intensity, emission wavelength) changes significantly when external stimuli are applied, such as grinding, shearing, stretching, pressure, etc., after solvent fumigation or heat treatment , which can be reversibly changed back to the initial state. As a new class of stimuli-responsive smart materials, piezochromic materials have attracted great attention, and they have important application prospects in the fields of information storage, commodity anti-counterfeiting, micro-stress sensing, security inks, and light-emitting devices. Compared with...

Claims

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Application Information

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IPC IPC(8): C09K11/06C09K9/02C07D277/84H01L51/46H01L51/54
CPCC09K9/02C09K11/06C07D277/84C09K2211/1037C09K2211/1007H10K85/657Y02E10/549
Inventor 邹祺朱亮亮陈文博赵婉冬吴佳成
Owner SHANGHAI UNIVERSITY OF ELECTRIC POWER