Compound containing fused ring and organic electroluminescent element employing the same
A compound and fused ring technology, which is applied in the field of fused ring compounds and organic EL elements, can solve the problems of undisclosed and unillustrated element performance, etc., and achieve the effects of long life, luminous efficiency and good heat resistance
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Embodiment 1
[0160] Example 1 (Synthesis of Compound (H-1) and Production of Organic EL Device)
[0161] (1) Synthesis of compound (H-1)
[0162] Compound (H-1) was synthesized as follows.
[0163]
[0164] In a 100ml three-necked flask, 1.68g (7mmol) of 2-phenyl-4-chloroquinazoline (catalogue No.16,243-4 manufactured by Aldrich Company), 4'-(N-carbazole)biphenylboron Salt 2.80g (7.7mmol), tetrakis (triphenylphosphine) palladium (O) 0.243g (0.21mmol, 3mol% Pd), the container was replaced with argon. Further, 26 ml of 1,2-dimethoxyethane and 12.5 ml (3 eq) of 2M aqueous sodium carbonate solution were added, and the mixture was heated to reflux in an oil bath at 90° C. for 9 hours. After completion of the reaction, the generated powder was collected by filtration to obtain 3.27 g of compound (H-1). Field desorption mass spectrometry (FD-MS, Field desorption mass spectrum) was performed on the obtained compound (H-1), and the results are as follows.
[0165] FD-MS: calcd for C 38 h 2...
Embodiment 2
[0171] Example 2 (Synthesis of Compound (H-2) and Production of Organic EL Device)
[0172] (1) Synthesis of compound (H-2)
[0173] Compound (H-2) was synthesized as follows.
[0174]
[0175]Intermediate b was synthesized using the method described in literature (J. Bergman, A. Brynolf, B. Elman and E. Vuorinen, Tetrahedron, 42, 3697-3706 (1986)). That is, in a 500 ml three-necked flask, 100 ml (100 mmol) of a 1 M tetrahydrofuran solution of phenylmagnesium bromide was added, and 100 ml of dry ether was added, followed by heating to reflux in an oil bath at 45°C. A solution of 5.91 g (50 mmol) of 2-cyanoaniline in 50 ml of dry ether was added dropwise thereto over 30 minutes. After further reflux for 1.5 hours, it was cooled to 0°C in an ice-water bath. Next, a solution of 13.2 g (60 mmol) of 4-bromobenzoic acid chloride in 100 ml of dry ether was added dropwise over 10 minutes, and heated to reflux in a 45° C. oil bath for 2 hours. After the reaction was completed, t...
Embodiment 3
[0182] Example 3 (Synthesis of Compound (H-3) and Production of Organic EL Device)
[0183] (1) Synthesis of compound (H-3)
[0184] Compound (H-3) was synthesized as follows.
[0185]
[0186] In a 500ml three-necked flask, 2.4g (100mmol) of magnesium and 100ml of dry tetrahydrofuran were added, and 100ml of a tetrahydrofuran solution of 35.4g (110mmol) of 4-(N-carbazole)phenyl bromide was added to prepare a Grignard reagent. A solution of 5.91 g (50 mmol) of 2-cyanoaniline in 50 ml of dry tetrahydrofuran was added dropwise thereto for 30 minutes under heating in an oil bath at 45°C. After further heating reaction for 1.5 hours, the mixture was cooled to 0°C in an ice-water bath. Next, a solution of 13.2 g (60 mmol) of 4-bromobenzoic acid chloride in 100 ml of dry ether was added dropwise over 10 minutes, followed by heating in an oil bath at 45° C. for 2 hours. After the reaction was completed, the mixture was cooled to 0° C. in an ice-water bath, and saturated aqueous...
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