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A thermally activated delayed fluorescence crystalline frame material and its preparation method and application

A technology for thermally activated delayed and frame materials, which is applied in the field of thermally activated delayed fluorescent crystalline frame materials and its preparation, and can solve problems such as sensitive, difficult to achieve TADF emission, and quenching of luminescence

Active Publication Date: 2022-03-15
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a thermally activated delayed fluorescence crystalline frame material and its preparation method and application, aiming at solving the problem that the existing frame material is sensitive to oxygen environment and easily causes luminescence quenching, Problems Difficult to Realize TADF Launch

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  • A thermally activated delayed fluorescence crystalline frame material and its preparation method and application
  • A thermally activated delayed fluorescence crystalline frame material and its preparation method and application
  • A thermally activated delayed fluorescence crystalline frame material and its preparation method and application

Examples

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Embodiment 1

[0093] Preparation of Thermally Activated Delayed Fluorescence Crystalline Framework Materials

[0094] (1) Synthesis of organic ligands

[0095] In a 250ml two-necked flask, add spirobiacridine (1.04g, 3mmol), methyl 4-bromobenzoate (1.29g, 6mmol), palladium acetate (34mg, 0.15mmol), tri-tert-butylphosphine tetrafluoroboric acid (131mg, 0.45mmol) and cesium carbonate (9.8g, 30mmol), then add 30ml redistilled toluene in an Ar atmosphere, heat to 120°C for 24h under anhydrous and oxygen-free conditions, then dichloromethane and petroleum ether The intermediate 1 (methyl 4,4'-(spirobiacridine)dibenzoate) was obtained after developing solvent column chromatography and drying by rotary evaporation. The yield was 82%. HRMS: theoretical value m / z[M+H + ]=615.2278, actual value m / z[M+H + ] = 615.2254.

[0096] In a 250ml one-necked flask, Intermediate 1 (1.5g, 2.44mmol) was dissolved in a mixed solution of 100mL tetrahydrofuran and water, wherein the volume ratio of tetrahydrofur...

Embodiment 2

[0105] (1) Preparation of Nanoscale Thermally Activated Delayed Fluorescence Crystalline Framework Materials

[0106] The organic ligand and synthesis method in this example are the same as those in Example 1.

[0107] In a 5ml glass bottle, add organic ligand (15mg, 0.025mmol), zirconium oxychloride (8mg, 0.025mmol) and N,N-dimethylformamide (1mL), after ultrasonication for 30min, add formic acid (10μL) , placed in an oven at 120°C for 24h. Then perform solvent exchange, wash with N,N-dimethylformamide and dichloromethane, and vacuum-dry at room temperature, and then vacuum-dry at 120°C to obtain a nanoscale heat-activated delayed fluorescence crystalline framework material, record For: Nano-Spiro-MOF-1.

[0108] The powder crystal diffraction pattern of Nano-Spiro-MOF-1 is as follows Figure 6 shown by Figure 6 It can be seen that the structure of Nano-Spiro-MOF-1 conforms to the crystal structure of Spiro-MOF-1.

[0109] The scanning electron microscope image of Nano-...

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Abstract

The invention discloses a thermally activated delayed fluorescence crystalline frame material and its preparation method and application. The preparation method of the thermally activated delayed fluorescent crystalline frame material comprises the steps of: providing zirconium salt and an organic solvent; synthesizing an organic ligand, and The structural formula of the organic ligand is: the zirconium salt and the organic ligand are dissolved in the organic solvent to react to obtain the thermally activated delayed fluorescence crystalline frame material; the reaction structural formula of the reaction is as follows It shows that the preparation method provided by the invention is simple in process, low in cost and easy to adjust. The thermally activated delayed fluorescence crystalline frame material prepared by the present invention has a large degree of non-conjugation, strong rigidity, high crystallinity, resistance to oxygen and water environment interference, fast radiation transition rate, and thermally activated delayed fluorescence emission resistant to oxygen quenching . The nanoscale heat-activated delayed fluorescence crystalline framework material provided by the invention can enter cells to realize cell imaging.

Description

technical field [0001] The invention relates to the technical field of organic fluorescent materials, in particular to a heat-activated delayed fluorescent crystal frame material and its preparation method and application. Background technique [0002] Thermally activated delayed fluorescence (TADF) materials belong to the third generation of luminescent materials. Compared with phosphorescent materials, TADF materials not only do not require the use of noble metal materials, but also the singlet state of the lowest excited state energy level (S 1 ) and triplet (T 1 ) can be effectively transmitted and transformed. Among them, the excitons in the triplet state can be utilized through reverse intersystem crossing, thereby greatly improving the luminous efficiency. Among them, the TADF polymer material is considered to be an ideal raw material for wet processing, and is suitable for spin coating and inkjet printing. design scope. [0003] In the past two decades, framewor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/10C08G83/00C09K11/06G01N21/64
CPCC07D471/10C09K11/06C08G83/008G01N21/6428G01N21/6456C09K2211/183
Inventor 杨楚罗别秉霖
Owner SHENZHEN UNIV