Arylamine derivative and organic electroluminescent device thereof

Abstract

The invention provides an arylamine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic photoelectric materials. According to the invention, a fluorene-derived group and a large steric hindrance group are bonded with a main structure of triarylamine to obtain the arylamine derivative. The arylamine derivative has good hole transporting abilityand thermal stability, is liable to form a film, simple to synthesize and easy to operate, can be applied to the organic electroluminescent device as a hole transporting layer, and can effectively solve problems that the hole transporting material in the organic electroluminescent device is poor in thermal stability, low in possibility of forming a film, low in light-emitting efficiency of deviceand serious in roll-off; and the organic electroluminescent device has the advantages of low driving voltage, high light-emitting efficiency and long service life.

Description

technical field

[0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine derivative and an organic electroluminescence device thereof. Background technique

[0002] Since 1987, Deng Qingyun and others from Kodak Corporation of the United States have adopted the method of vacuum deposition coating, using Alq 3 As a light-emitting layer, successfully achieved a low voltage of 10V and a high brightness of 1000cd / m 2 Green light emission, the device efficiency is 1.5lm / W, and the service life is over 100h. This move makes organic electroluminescent materials and devices have the possibility of practicality, thus driving the research upsurge of organic materials in this field of electroluminescence. After more than 30 years of development, the efficiency of organic electroluminescent devices has been greatly improved, and because of its self-illumination, wide viewing angle, full curing, full color, fast response,...

Examples

Embodiment 1

[0078][Example 1] Synthesis of Compound 1

[0079]

[0080] Step1: Add 3-amino-11,11-dimethyl-11H-benzofluorene (2.59g, 10mmol), 3-bromo-11,11-dimethyl-11H-benzofluorene (3.23g , 10mmol), Pd 2 (dba) 3 (0.21g, 0.25mmol), P(t-Bu) 3 (0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), 100mL of toluene solution, reacted at 100°C for 24h, extracted the organic phase with diethyl ether and water after the reaction, and washed the organic layer with MgSO 4 Drying, concentration of organic matter, column chromatography and recrystallization gave intermediate 1-1 (3.96 g, 79%).

[0081] Step2: Add intermediate 1-1 (5.02g, 10mmol), 3-bromo-10-phenyl-10H-phenoxazine (3.38g, 10mmol), Pd to the reactor 2 (dba) 3 (0.21g, 0.25mmol), P(t-Bu) 3 (0.18g, 0.84mmol), NaOt-Bu ((2.8g, 25mmol), 100mL of toluene solution, reacted at 100°C for 24h, extracted the organic phase with ether and water after the reaction, and washed the organic layer with MgSO 4 Dry, concentrate the organic matter, go throug...

Embodiment 2

[0082] [Example 2] Synthesis of Compound 6

[0083] Compound 6 (5.14 g, 77%) was obtained according to the synthesis method of compound 1 in Example 1.

[0084]

Embodiment 3

[0085] [Example 3] Synthesis of compound 24

[0086] Compound 24 (5.23 g, 80%) was obtained according to the synthesis method of compound 1 in Example 1.

[0087]

technical field

[0001] The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine derivative and an organic electroluminescence device thereof. Background technique

[0002] Since 1987, Deng Qingyun and others from Kodak Corporation of the United States have adopted the method of vacuum deposition coating, using Alq 3 As a light-emitting layer, successfully achieved a low voltage of 10V and a high brightness of 1000cd / m 2 Green light emission, the device efficiency is 1.5lm / W, and the service life is over 100h. This move makes organic electroluminescent materials and devices have the possibility of practicality, thus driving the research upsurge of organic materials in this field of electroluminescence. After more than 30 years of development, the efficiency of organic electroluminescent devices has been greatly improved, and because of its self-illumination, wide viewing angle, full curing, full color, fast response,...

Examples

Embodiment 1

[0078][Example 1] Synthesis of Compound 1

[0079]

[0080] Step1: Add 3-amino-11,11-dimethyl-11H-benzofluorene (2.59g, 10mmol), 3-bromo-11,11-dimethyl-11H-benzofluorene (3.23g , 10mmol), Pd 2 (dba) 3 (0.21g, 0.25mmol), P(t-Bu) 3 (0.18g, 0.84mmol), NaOt-Bu (2.8g, 25mmol), 100mL of toluene solution, reacted at 100°C for 24h, extracted the organic phase with diethyl ether and water after the reaction, and washed the organic layer with MgSO 4 Drying, concentration of organic matter, column chromatography and recrystallization gave intermediate 1-1 (3.96 g, 79%).

[0081] Step2: Add intermediate 1-1 (5.02g, 10mmol), 3-bromo-10-phenyl-10H-phenoxazine (3.38g, 10mmol), Pd to the reactor 2 (dba) 3 (0.21g, 0.25mmol), P(t-Bu) 3 (0.18g, 0.84mmol), NaOt-Bu ((2.8g, 25mmol), 100mL of toluene solution, reacted at 100°C for 24h, extracted the organic phase with ether and water after the reaction, and washed the organic layer with MgSO 4 Dry, concentrate the organic matter, go throug...

Embodiment 2

[0082] [Example 2] Synthesis of Compound 6

[0083] Compound 6 (5.14 g, 77%) was obtained according to the synthesis method of compound 1 in Example 1.

[0084]

Embodiment 3

[0085] [Example 3] Synthesis of compound 24

[0086] Compound 24 (5.23 g, 80%) was obtained according to the synthesis method of compound 1 in Example 1.

[0087]

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