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Synthesis method and application of diphenyl sulfone-based double-chromophore thermally activated delayed fluorescent materials

A delayed fluorescence, dual chromophore technology, applied in the field of organic electroluminescent materials, can solve the problem of width at half maximum

Active Publication Date: 2019-11-19
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such TADF molecules usually only show a single emission peak in solution and solid film, and its half-width is relatively broad.

Method used

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  • Synthesis method and application of diphenyl sulfone-based double-chromophore thermally activated delayed fluorescent materials
  • Synthesis method and application of diphenyl sulfone-based double-chromophore thermally activated delayed fluorescent materials
  • Synthesis method and application of diphenyl sulfone-based double-chromophore thermally activated delayed fluorescent materials

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesis of compound 3a

[0027] Compound 1 (5.0 g, 0.03 mol ), NaH (1.44 g, 0.06 mol ) and 100 mL of dry N,N-dimethylformamide (DMF) were sequentially added into a 250 mL three-necked flask, and the mixture was placed in a nitrogen atmosphere at Stir at room temperature for 30 min; add compound 2 (7.62 g, 0.03 mol), then raise the temperature to 100°C and stir for 4 h. After the reaction solution was cooled to room temperature, it was poured into a large amount of water, and a white solid was precipitated. Suction filtration, the solid was washed successively with ethanol and diethyl ether, and dried, and the resulting white solid was further purified by column chromatography, and purified with petroleum ether / dichloromethane ( V / V ; 2:1) as the eluent to obtain white solid compound 3a (3.85 g, yield: 32%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.15 (dd, J= 11.0, 8.2 Hz, 2H), 8.07(dd, J= 8.8,5.0 Hz, 1H), 7.77 (d, J= 8.6 Hz, 1H), 7.43 (q, J= 8.3 Hz, 2H), 7.37-7.29 (m...

Embodiment 2

[0069] Compound M 1 -M 5 The thermogravimetric curves are shown in Figure 1, and their thermal decomposition temperatures are 480, 447, 402, 393, and 549°C, respectively. According to the corresponding molecular structure and the change trend of thermal decomposition temperature, the following conclusions can be drawn: the introduction of halogen atom bromine and the insertion of oxygen atom or alkoxy group all reduce the thermal decomposition temperature of the compound to a certain extent T d . Structurally, it can be explained that the carbon-bromine bond has a lower dissociation energy, so M 1 ~ M 4 The trend of thermal decomposition temperature change is M 2 1 ,M 4 3 ; Further with the insertion of oxygen atoms and alkoxy groups, the rigid structure of the molecule is reduced, so M 3 and M 4 of T d Average ratio M 1 and M 2 Low. m 5 It has the largest conjugated structure, so its thermal decomposition temperature is the highest at 549°C.

Embodiment 3

[0071] To study compound M 1 ~ M 5 The electrochemical performance of the compound was tested by cyclic voltammetry in chloroform solution. As shown in Figure 2 (inset is Fc / Fc ＋ CV curve), compound M 1 ~ M 5 All exhibit irreversible oxidation-reduction potentials in the voltage range of -1.5 to 2.0V. According to the oxidation potential ( E ox ) and reduction potential ( E red ) value, by the formula E (HOMO) (eV)=-( E ox.vsFc / Fc+ +4.8) eV; E (LUMO) (eV)=-( E red.vsFc / Fc+ +4.8) eV; E ox.vsFc / Fc+ =( E ox -0.50) V and E red.vsFc / Fc+ =( E red -0.50) V (wherein the actual test process Fc / Fc ＋ The potential relative to Ag / AgCl is 0.50V) to calculate M 1 ~ M 5 The HOMO energy levels are -5.4, -5.12, -5.15, -5.75, -5.4 eV; and the LUMO energy levels are -3.59, -3.62, -3.63, -3.62, -3.61 eV. The results showed that the introduction of bromine atoms and oxygen atoms or alkoxy groups mainly had a greater impact on the HOMO energy levels of the compounds; w...

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Abstract

The invention discloses thermally activated delayed fluorescent materials containing double chromophores, and an application thereof in solution-processible organic electroluminescent devices. A carbazole-diphenyl sulfone blue light-emitting chromophore used as a terminal group and a triphenylamine-anthraquinone orange red light-emitting chromophore used as a central core are connected in non-conjugated and conjugated manners to construct the double-chromophore thermally activated delayed fluorescent materials. The materials are beneficial for separating the spatial distribution of the highestoccupied orbits and the lowest empty orbits of molecules to obtain a small energy gap between a single state and a triple state; and the intramolecular energy transfer of the materials changes with the connection mode, and dual emission of the single molecules is achieved. The double-chromophore thermally activated delayed fluorescent materials can be used as the luminescent layer material of a solution-processible organic electroluminescent diode to make the devices have a maximum external quantum efficiency of 3.96%.

Description

technical field [0001] The invention relates to a class of thermally active delayed fluorescent materials with dual chromophores based on diphenyl sulfone units, in particular to a single-molecule dual-emission material with TADF (thermally activated delayed fluorescent) red light material as the core and TADF blue light material as the end The thermally active delay material and its application as a light-emitting layer material of a solution-processed organic electroluminescent diode belong to the technical field of organic electroluminescent materials. Background technique [0002] Thermally activated delayed fluorescence (TADF) materials do not contain metal atoms, and can make full use of singlet and triplet excitons to emit light, with an internal quantum efficiency of 100%, known as the third generation of organic electroluminescent materials. In recent years, TADF materials have been greatly developed, and its structure is generally composed of electron donor (D) uni...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D209/86C09K11/06G01N21/64
CPCC07D209/88C07D209/86C09K11/06G01N21/6408G01N21/33G01N27/48C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1014G01N2021/6413
Inventor 王亚飞汪向兵谭帅朱卫国
Owner CHANGZHOU UNIV
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