Red thermal activation delayed fluorescence material, organic electroluminescent device and preparation method of red thermal activation delayed fluorescence material
A technology of thermal activation delay and fluorescent material, applied in the field of fluorescent materials, can solve the problem of low external quantum efficiency of devices, and achieve the effect of low start-up voltage and high external quantum efficiency
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Embodiment 1
[0052] 10-(6-(9,9'-spirobis[fluorene]-3-yl)-11,12-diphenyldibenzo[a,c]phenazin-3-yl)-10hydro-phenoxa The preparation method of oxazine, comprises the steps:
[0053] S1. Compound (0.72g, 2mmol) shown in formula (3), compound (2.1mmol, 0.77g) shown in formula (2), tetrakistriphenylphosphine palladium (0.1mmol, 0.11g), potassium carbonate (4mmol , 0.55g) was added to a 100 ml three-necked flask, followed by 60 ml of toluene / ethanol / water (3:1:2), heated to 95°C and reacted under nitrogen for 24 hours. After cooling to room temperature, the crude product was washed with silica gel Concentrated and purified by column chromatography, 660 mg of yellow product was obtained with a yield of 55%. The reaction scheme is as follows:
[0054]
[0055] Structural characterization of the product obtained in step S1, the results are as follows:
[0056] 1H NMR (400MHz, CDCl3) δ8.31(d, J=8.0Hz, 1H), 8.28(s, 1H), 8.18(s, 1H), 8.12(s, 1H), 8.08(t, J=8.8Hz ,1H),7.99(d,J=7.6Hz,1H),7.88(d,J=7...
Embodiment 2
[0066] This example provides a 10-(6-(9,9'-spirobi[fluorene]-3-yl)-11,12-diphenyldibenzo[a,c]phene prepared in Example 1 Oxazin-3-yl)-10hydro-phenoxazine as an organic electroluminescent device as a luminescent dye, such as figure 1 As shown, it consists of a glass substrate 1 , a hole transport layer 2 , electron blocking layers 3 and 4 , a light emitting layer 5 , an electron transport layer 6 and a cathode layer 7 arranged in sequence.
[0067] The fabrication of the device uses a 15Ω indium tin oxide (ITO) transparent electrode glass substrate. Before the vacuum evaporation of the organic light-emitting device, the ITO substrate is washed and pretreated with isopropanol, water and acetone, and then placed at 100 ° C. Dry it in a blast drying oven, and then use an ultraviolet ozone cleaning machine for surface treatment. Finally, the glass substrate 1 is put into a vacuum evaporation apparatus to conduct evaporation of each layer by a vacuum evaporation method, and a cross...
Embodiment 3
[0070] This example provides another 10-(6-(9,9'-spirobi[fluorene]-3-yl)-11,12-diphenyldibenzo[a,c] prepared in Example 1 Phenazin-3-yl)-10 hydrogen-phenoxazine is used as an organic electroluminescent device of a luminescent dye, and the specific manufacturing process is as follows:
[0071] On the glass substrate 1 , the hole transport layer 2 , the electron blocking layers 3 and 4 , the light emitting layer 5 and the electron transport layer 6 , and the cathode layer 7 were sequentially evaporated. 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC) with a film thickness of 35 nm was used as the hole transport layer 2, and 4, with a film thickness of 10 nm, 4',4"-tris(carbazol-9-yl)triphenylamine (TCTA) and 10 nm of 1,3-bis(9hydro-carbazol-9-yl)-benzene (mCP) as double electron blocking layer3 and 4, with pure 10-(6-(9,9'-spirobis[fluoren]-3-yl)-11,12-diphenyldibenzo[a,c]phenazin-3-yl)- 10 Hydrogen-phenoxazine is used as the light-emitting layer 5, and 3,3'-[5'-[3-(...
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