Organic electrolumescence device
an electroluminescence device and organic technology, applied in the direction of organic compounds/hydrides/coordination complex catalysts, organic/chemical process catalysts, anthracene dyes, etc., can solve the problems of low light emission efficiency, inferior luminance of emitted light, and low efficiency of light emission in comparison, and the properties of organic el devices deteriorate very rapidly
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synthesis example 1
Compound (2)
Synthesis of Intermediate Compound A
In a 200 ml round bottom flask, 0.38 g (2.04 mmole) of 4-bromobenzaldehyde and 0.98 g (4.29 mmole) of ethyl benzylphosphonate were dissolved in 40 ml of dimethylsulfoxide. To this was added 0.5 g (4.49 mmole) of potassium t-butoxide in small portions at the room temperature and the resulting mixture was stirred for 18 hours. The reaction mixture was poured into 500 ml of water, solid was filtered to give yellow solid (0.5 g).
In a 100 ml round bottom flask, the crystals obtained above, 2.0 g (12.0 mmole) of potassium iodide and 1.14 g (6.0 mmole) of copper iodide were dissolved in 10 ml of hexamethylphosphoramide and the resulting mixture was stirred under heating at 150° C. for 6 hours. After the reaction was completed, 10 ml of a 1 N aqueous hydrochloric acid was added to the reaction mixture and the organic layer was extracted with toluene. After the extract was concentrated, the reaction product was purified by recrystallizing...
synthesis example 2
Compound (9)
Synthesis of Intermediate Compound C
In a 200 ml round bottom flask, 51.2 g (0.3 mole) of diphenylamine, 71.4 g (0.3 mole) of 1,4-dibromobenzene, 34.6 g (0.36 mole) of potassium t-butoxide, 4.2 g (5.9 mmole) of PdCl2(PPh3)2 and 1.2 liter of xylene were mixed together and the obtained mixture was stirred at 130° C. for one night.
After the reaction was completed, the organic layer was concentrated and about 100 g of brown crystals were obtained. The crystals were purified in accordance with the column chromatography (silica gel, hexane / toluene=10 / 1) and 28 g (the yield: 29%) of the following Intermediate Compound C was obtained:
Synthesis of Compound (9)
In a 100 ml round bottom flask, 0.48 g (1 mmole) of Intermediate Compound B was dissolved in 10 ml of diethyl ether and the mixture was cooled to −78° C. To the cooled mixture, 2 ml (1.5 M, 3 mmole) of n-butyllithium was added and the resulting mixture was stirred for 1 hour. Then, a solution prepared by dissolving...
synthesis example 3
Compound (18)
Synthesis of Intermediate Compound D
A Grignard reagent was prepared by adding magnesium- and diethyl ether to 0.48 g (2.0 mmol) of 1,4-dibromobenzene. Separately, in a 100 ml round bottom flask, 5.7 g (20.0 mmole) of 1,4-dibromonaphthalene and 10 mg of NiCl2(dppp) were dissolved in 20 ml of diethyl ether and the resulting mixture was cooled in an ice bath. To the cooled mixture, the Grignard reagent prepared above was added and the obtained mixture was stirred under refluxing for 6 hours. After the reaction was completed, 10 ml of a 1 N aqueous hydrochloric acid was added. After the organic layer was separated, the solvent was removed by distillation and 0.30 (the yield: 30%) of the following Intermediate Compound D was obtained:
Synthesis of Compound (18)
In a 100 ml round bottom flask, 0.09 g (1.0 mmole) of aniline and 0.25 g (2.5 mmole) of acetic anhydride were dissolved into 5 ml of methylene chloride. The resulting mixture was stirred at the room temperature...
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- wherein A represents a chrysene group X1 to X4 each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, X1 and X2 may be bonded to each other, X3 and X4 may be bonded to each other, Y1 to Y4 each independently represent an organic group represented by general formula [2], a to d each represent an integer of 0 to 2 and, a+b+c+d≧0; general formula [2] being:
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