Synthesis and application of dual chromophore thermally active delayed fluorescent materials based on diphenylsulfone
A technology of delayed fluorescence and dual chromophores, applied in the field of organic electroluminescent materials, which can solve problems such as half-peak width
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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 to a 250 mL three-necked flask, and the mixture was placed in a nitrogen atmosphere at room temperature Stir for 30 min; after adding compound 2 (7.62 g, 0.03 mol), the temperature is raised to 100 °C and stirred 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 with ethanol and diethyl ether in turn, and dried, the obtained white solid was further purified by column chromatography, and the white solid compound 3a (3.85 m) was obtained with petroleum ether / dichloromethane (V / V; 2:1) as the eluent. g, Yield: 32%). 1 H NMR (400MHz, CDCl 3 )δ8.15(dd,J=11.0,8.2Hz,2H),8.07(dd,J=8.8,5.0Hz,1H),7.77(d,J=8.6Hz,1H),7.43(q,J=8.3 Hz, 2H), 7.37-7.29(m, 1H), 7.26(t, J=8.5Hz, 1H).
[0028...
Embodiment 2
[0069] Compound M 1 -M 5 The thermogravimetric curve of figure 1 As shown, the thermal decomposition temperatures are 480, 447, 402, 393, 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 insertion of oxygen atom or alkoxy group reduces the thermal decomposition temperature T of the compound to a certain extent d . It can be explained from the structure that the carbon-bromine bond has a lower dissociation energy, so M 1 ~M 4 The thermal decomposition temperature variation trend 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 T d Average ratio M 1 and M 2 Low. M 5 Has the largest conjugated structure, so its thermal decomposition temperature is the highest 549 ℃.
Embodiment 3
[0071] To study compound M 1 ~M 5 The electrochemical properties of the compounds were tested by cyclic voltammetry in chloroform solutions. like figure 2 shown (inset is Fc / Fc + CV curve), compound M 1 ~M 5 All showed irreversible redox potentials in the range of -1.5 to 2.0 V. According to the oxidation potential (E ox ) and reduction potential (E red ) value, given 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 (in which Fc / Fc in the actual test process + 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, respectively. The results show that the introduction of bromine atom and oxygen atom or alkoxy group mainly affects the HOMO energy level of the compound; while their LUMO energy level has little ...
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