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A kind of compound containing nitrogen heterozolium structure and its application
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A compound and azapine technology, which is applied in the field of organic electroluminescence, can solve problems that affect device life and efficiency, and organic materials are prone to crystallization, so as to improve device efficiency, reduce synthesis cost, and increase reaction yield.
Active Publication Date: 2022-07-15
烟台九目化学股份有限公司
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However, due to the Joule heat generated when the OLED device is operated with an applied voltage, the organic material is prone to crystallization, which affects the life and efficiency of the device.
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[0029] 1. Preparation of intermediate M-1:
[0030]
[0031] Under nitrogen protection, 10.0 g of 2-bromo-3-fluorodibenzofuran, 6.0 g of carbazole, 18.4 g of cesium carbonate, and 60 mL of N,N-dimethylformamide were added to the reaction flask, and the temperature was heated and refluxed for insulation. 12h. After the reaction is complete, add toluene to extract the organic phase, and extract the reaction water phase with toluene, combine the organic phases, and wash with purified water until the organic phase becomes neutral. After washing with water, drying, passing through column, removing solvent, and recrystallization from toluene / ethanol, 10 g of light yellow solid was obtained, and the yield was 65%. The pale yellow solid was identified as intermediate M-1 according to LC-MS analysis. LC-MS: M / Z 412.28.
[0032] 2. Preparation of intermediate M-2:
[0033]
[0034] Under nitrogen protection, 10g of M-1, 7.4g of pinacol diboronic acid ester, 7g of potassium ace...
Embodiment
[0042] 1. Preparation of compound 3-1
[0043]
[0044] Under nitrogen protection, 10 g of M-4, 2.7 g of phenylboronic acid, 0.3 g of dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphinepalladium (II), 2.1 g of potassiumhydroxide, and purified water were mixed together. 6.3g, 80mL of dioxane was added to the reaction flask, the temperature was raised to 70-80°C and kept for 6h. After the reaction was completed, it was left to stand for stratification, and the organic phase was washed with water until neutral. Recrystallization from ethanol gave 6.4 g of off-white solid, yield: 60%. According to LC-MS analysis, the white solid was identified as compound 3-1, LC-MS: M / Z 483.56, and the NMR test result of compound 3-1 was: 1HNMR(CDCl3): δ7.53-7.80(8H,7.59(tdd,J=6.5,2.2,1.5Hz),7.65(ddd,J=8.0,5.1,1.8Hz),7.66(dddd,J=7.6,6.5 ,1.8,0.5Hz),7.71(ddd,J=8.0,5.8,2.0Hz),7.72(t,J=5.1Hz),7.74(ddd,J=5.7,5.0,1.7Hz),7.73(d,J =0.5Hz)),7.84-8.57(10H,7.91(dddd,J=7.6,1.8,1.5,0.5Hz),7.95(ddd...
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Abstract
The present invention relates to a nitrogen-containing heterocyclic structure compound, which belongs to the field of organic electroluminescence. one of substituted or unsubstituted C10-C14 fused-ring aryl or furyl, thienyl, anthracenyl, phenanthryl, naphthyl, phenylcarbazole, pyrene, methylfluorene, and phenylfluorene. The compound containing the nitrogen heterostructure is applied to an organic electroluminescence device. The compound is a derivative of a nitrogen-containing heterocyclic structure connected with fluorene. Because the nitrogen-containing seven-membered ring structure blocks the conjugation of the benzene ring, the triplet state of the molecule is maintained and has a higher triplet stateenergy level. The energy transfer is more sufficient, the transfer of electrons and holes is more balanced, and the efficiency and lifetime of the device are higher.
Description
technical field [0001] The invention relates to a nitrogen-containing heterocyclic structure compound and application thereof, and belongs to the technical field of organic electroluminescence. Background technique [0002] Organic light-emitting device (OLED) has become a research hotspot in the field of flat panel information display. OLED has the advantages of flat panel, self-luminous, rich color, fast response, wide field of view, and easy to achieve ultra-thin and lightweight. It is considered as a new technology that is most likely to replace liquid crystal displays and plasma displays in the future. Backlight. However, the problems of high production cost and low yield remain to be solved. Unlike traditional LCD displays, OLED display technology does not require a backlight and uses a very thin coating of organic materials and glass substrates that emit light when an electric current flows through them. Moreover, OLED display screens can be made lighter and thinne...
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