Nitrogen-containing heterocyclic derivative and organic electroluminescence element using the same
A technology of derivatives and nitrogen heterocycles, applied in the field of nitrogen-containing heterocycle derivatives and organic electroluminescent elements using the same, can solve the problem of high driving voltage, low voltage, high luminous brightness, luminous efficiency, low luminous brightness or low luminous efficiency and other problems, to achieve the effect of high luminous efficiency
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Synthetic example 1
[0219] Synthesis of Synthesis Example 1 Compound (1)
[0220] (1-1) Synthesis of intermediate 1
[0221] Dissolve 5.0 g (0.015 mol) of 2-nitro-4-bromo-1-phenylaminonaphthalene in 50 mL of tetrahydrofuran, stir at room temperature under an argon atmosphere, and then drip 13 g (0.075 mol) of sodium dithionite into water 40 mL of solution. Further, 5 mL of methanol was added, followed by stirring for 1 hour. Next, 40 mL of ethyl acetate was added, and a solution of 2.5 g (0.030 mol) of sodium bicarbonate / 20 mL of water was added. Furthermore, a solution of 2.0 g (0.015 mol) of 4-bromobenzoyl chloride / 10 mL of ethyl acetate was added dropwise, and stirred at room temperature for 3 hours. Extract with ethyl acetate, wash with water and saturated brine successively, and then dry over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. After purification by silica gel column chromatography (developing solvent: chloroform), recrystallization was car...
Synthetic example 2
[0229] Synthesis of Synthesis Example 2 Compound (2)
[0230] In place of 10-naphthalene-2-yl-anthracene-9-boronic acid, except that 10-naphthalene-1-yl-anthracene-9-boronic acid was used, the same operation as the synthesis of compound (1) was carried out to obtain a light yellow powder Compound (2) was obtained. Yield 3.0 g (64% yield). The product was identified as compound (2) by FD-MS (field desorption mass spectrometry) measurement.
[0231] [chem 23]
[0232]
[0233] Compound (1) Compound (2)
Embodiment 1
[0234] Example 1 (manufacture of organic EL element)
[0235] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropanol for 5 minutes, and then to UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode lines after washing is installed on the substrate holder of the vacuum evaporation device. First, on the side where the transparent electrode lines are formed, a 60nm film of N is formed to cover the above-mentioned transparent electrodes. N'-bis(N,N'-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4'-diamino-1,1'-biphenyl film (hereinafter referred to as "TPD232 film"). This TPD232 film can function as a hole injection layer. After the TPD232 film is formed into a film, on the TPD232 film, a 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl film (hereinafter abbreviated as "NPD") with a film thickness of 20 nm is formed. membrane"). This NPD film c...
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