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Carbazole group-containing bipyridino [3, 2-a:2', 3'-c] phenazine tricarbonyl rhenium (I) complexes, preparation method and application thereof

A technology of carbazole dipyridine and carbazole groups, applied in the field of organic electroluminescent devices, can solve the problems of unreached carrier transport performance, long excited state lifetime, annihilation, etc., achieve high yield, improve performance, stable effect

Inactive Publication Date: 2014-11-26
NANJING UNIV OF INFORMATION SCI & TECH
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Problems solved by technology

However, the rhenium complexes reported in the literature have longer excited state lifetimes, and are prone to triplet-triplet and triplet-polaron annihilation, and the carrier transport performance of the material has not reached that of organic electroluminescent devices OLEDs. Require

Method used

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  • Carbazole group-containing bipyridino [3, 2-a:2', 3'-c] phenazine tricarbonyl rhenium (I) complexes, preparation method and application thereof
  • Carbazole group-containing bipyridino [3, 2-a:2', 3'-c] phenazine tricarbonyl rhenium (I) complexes, preparation method and application thereof
  • Carbazole group-containing bipyridino [3, 2-a:2', 3'-c] phenazine tricarbonyl rhenium (I) complexes, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Preparation of precursor 4-bromo-7-carbazol[2,1,3]-benzothiadiazole or 4,7-dicarbazol[2,1,3]-benzothiadiazole

[0035] Precursors were synthesized according to literature methods [see: (a) Neto, B.A.D., Lopes, A. S., Wüst, M., Costa, V. E. U., Ebeling, G., Dupont, J., Tetrahedron Lett ., 2005,46, 6843; (b) Mancilha, F. S., Neto, B. A. D., Lopes, A. S., Quina, F. H., Goncalves, R. S., Dupont ,J., Eur. J. Org. Chem. , 2006, 4924; (c) Tao, Y. M., Li, H. Y., Xu, Q. L., Zhu, Y. C., Kang, L. C., Zheng, Y. X., Zuo, J. L., You, X. Z., Synth. Met. , 2011, 161, 718.].

[0036] The details are as follows: In a reaction kettle, carbazole (5.02 g, 30 mmol), 4,7-benzothiadiazole (2.94 g, 10 mmol), cuprous iodide (0.19 g, 1 mmol), 18- Crown-6 (0.088 g, 0.33 mmol), potassium carbonate (5.53 g, 40 mol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinedione (DMPU ) (0.5 mL) mixed, filled with nitrogen, at 180 o C for 24 hours. After cooling to room temperature, soak ...

Embodiment 2

[0037] Example 2: Ligand 10-bromo-13-carbazoledipyridin[3,2-a:2',3'-c]phenazine (L1) or 10,13-dicarbazoledipyridin[3,2 -a:Synthesis of 2',3'-c]phenazine (L2)

[0038] (1) Synthesis method (see Figure 4 with Figure 5 )details as follows:

[0039] In a 100 mL round bottom flask, add 4-bromo-7-carbazol[2,1,3]-benzothiadiazole or 4,7-dicarbazol[2,1,3]-benzothiadiazole azole (0.56 mmol), then add NaBH 4 (11.2 mmol) and catalyst CoCl 2 ·6H 2 O (5×10 -3 mmol), under the condition of avoiding light, evacuate and pass nitrogen three times respectively, add 30 mL of absolute ethanol with a syringe, and raise the temperature to 70 o C reflux reaction for 48 hours. Cool to 20-25 o C, add 5 mL ammonia water, add 10 mL 1,10-phenanthroline-5,6-dione ethanol solution with a syringe (the total content of 1,10-phenanthroline-5,6-dione is 2.8 mmol), heated up again to 70 o C reflux reaction for 8 hours. After the reaction, the reaction mixture was cooled to 20-25 o C, the solve...

Embodiment 3

[0057] Example three: complex tricarbonyl chloride . [10-bromo-13-carbazoledipyridyl[3,2-a:2',3'-c]phenazine] rhenium (I) ( L1 ) and tricarbonyl chloride . Synthesis of [10,13-dicarbazoledipyridyl[3,2-a:2',3'-c]phenazine]rhenium(I) (L2Re)

[0058] (1) Synthesis method (see Image 6 with Figure 7 )details as follows:

[0059] Ligands containing carbazole dipyridin[3,2-a:2',3'-c]phenazine L1 or L2 and pentacarbonyl rhenium chloride Re(CO) 5 Cl was added to the container in an equimolar proportion (0.10 mmol), and the temperature was rapidly raised to 110 in anhydrous toluene (30 mL). o C was refluxed and refluxed for 6 hours, the solvent was distilled off, and the obtained solid was purified by column chromatography to obtain the corresponding complex bipyrido[3,2-a:2',3'-c]phenone containing a carbazole group. Azinetricarbonyl rhenium(I) complexes, i.e. tricarbonyl chloride . [10-Bromo-13-carbazoledipyridyl[3,2-a:2',3'-c]phenazine]rhenium(I) (L1Re) or tricarbonyl chlor...

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Abstract

The invention provides carbazole group-containing bipyridino [3, 2-a:2', 3'-c] phenazine tricarbonyl rhenium (I) complexes, a preparation method and an application thereof. Annihilation among triplet states of the two rhenium complexes is less. The rhenium complexes have higher transmission performances and better luminescent properties, and can be used as good materials for manufacturing electroluminescent devices.

Description

technical field [0001] The present invention relates to complexes of rhenium, and also relates to organic electroluminescent devices. Background technique [0002] Organic Electroluminescence (EL or OEL for short) is a phenomenon that converts electrical energy into light energy in a device. Organic Light-emitting Diodes (OLEDs for short), also known as light-emitting diodes, are A device for realizing organic electroluminescence. Compared with other flat-panel display technologies such as inorganic electroluminescent display, liquid crystal display, and plasma display, organic electroluminescent display has the characteristics of low energy consumption, low cost, wide viewing angle, high brightness, large area, and wide luminous range. more and more noticeable. [0003] In 1987, C. W. Tang et al. of Kodak Corporation of the United States [see: Tang, C. W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913] used ultra-thin-film technology to prepare an electroluminescent (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00C07D471/14C09K11/06H01L51/54
Inventor 周永慧陈敏东王正梅徐晶晶高桂枝
Owner NANJING UNIV OF INFORMATION SCI & TECH
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