Iridium-containing organic electroluminescent material, preparation method thereof and organic electroluminescent device
A luminescent and electromechanical technology, applied in the fields of luminescent materials, electric solid devices, organic chemistry, etc.
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[0048] Such as figure 1 As shown, the preparation method of the above-mentioned iridium-containing organic electroluminescent material may comprise the following steps:
[0049] The following steps are all under anaerobic conditions, such as, in N 2 Or under an inert gas atmosphere, etc., the solvent used can also use other solvents that have better compatibility with the reactant than the solvents given in each step.
[0050] Step S1: In N,N-dimethylformamide (DMF) solvent, compound C (2,4-difluoroiodobenzene) and compound D (benzimidazole) in copper iodide (CuI), 1, 10-phenanthroline and cesium carbonate (CeCO 3 ) under the action of a mixed catalyst composed of 100 ~ 180 ° C environment for Ullmann coupling reaction, prepared compound E (1-(2,4-difluorophenyl) benzimidazole), the reaction formula is as follows:
[0051]
[0052] Preferably, step S1 further includes a step of separation and purification of compound E: first, the mixed solution after the Ullmann couplin...
Embodiment 1
[0067] Example 1: Bis(1-(4,6-difluorophenyl)-3-methyl-benzimidazole-C, C 2 ) (2-(2'-pyridyl) imidazole) synthesis of iridium:
[0068] (1) The 3-position substituent on the benzimidazolyl is the synthesis of the two-bridge compound of methyl:
[0069] 0.16g (0.836mmol) CuI, 1.20g (10.15mmol) benzimidazole and 5.70g (17.50mmol) cesium carbonate were sequentially added to a 50mL round-bottomed reaction flask wrapped in aluminum foil, and nitrogen was blown for 15min. 1 mL (8.36 mmol) of 2,4-difluoroiodobenzene, 0.30 g (1.67 mmol) of 1,10-phenanthroline and 25 mL of anhydrous N,N-dimethylformamide were sequentially added in a nitrogen stream. After passing nitrogen gas through the reaction mixture for 30 min, the oil bath was heated to 110° C. and stirred for 24 h. After the mixture was cooled to room temperature, it was concentrated in vacuo. Add 10 mL of ethyl acetate to the concentrated solution, filter, and wash with 30 mL of ethyl acetate. The filtrate was concentrated, ...
Embodiment 2
[0086] Example 2: Bis(1-(4,6-difluorophenyl)-3-ethyl-benzimidazole-C, C 2 ) (2-(2'-pyridyl) imidazole) synthesis of iridium:
[0087] (1). For the synthesis of a two-bridge compound whose 3-position substituent is ethyl on the benzimidazolyl, refer to Example 1;
[0088] (2). The synthesis of 2-(2'-pyridyl) imidazole is the same as that of Example 1;
[0089] (3). Final product (46dfpmb) 2 Synthesis of Ir(pym):
[0090] Under nitrogen protection, 1.83g (1.23mmol) of a two-bridge compound whose 3-position substituent on the benzimidazole base is ethyl, 0.549g (3.78mmol) of 2-( 2'-pyridyl)imidazole, 80 mL 1,2-dichloroethane, 0.997 g (18.45 mmol) sodium methoxide, 0.543 g (2.46 mmol) silver trifluoromethyl acetate. The reaction was stirred at reflux for 24h. After cooling, it was filtered and the mother liquor was concentrated to obtain a brown-yellow solid. After the solid was washed in an appropriate amount of n-hexane and diethyl ether under the action of ultrasound, the...
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