Organic electroluminescent material and preparation method and application thereof

Abstract

The invention relates to the technical field of organic electroluminescent display, in particular to an organic electroluminescent material. The organic electroluminescent material has a structure asshown in a general formula I. The compound of the structure has high hole mobility, good film stability, suitable molecular energy levels and high glass transition temperature, the transport efficiency of carriers and the luminous efficiency of a device can be improved, and the organic electroluminescent material can be applied to the field of organic electroluminescence as a hole transport material.

Description

technical field

[0001] The invention relates to a novel organic electroluminescent material and its application in organic electroluminescent devices, belonging to the technical field of organic electroluminescent display. Background technique

[0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescence display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backli...

Examples

Embodiment 1

[0058] Synthesis of (Compound 1)

[0059] The synthetic route is as follows:

[0060]

[0061] 1) Synthesis of compound 1-2

[0062] 1000 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1 g (0.48 mol) of sodium tert-butoxide, 32.15 g (purity 99%, 0.3 mol) of o-toluidine, and 64.44 g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and toluene 400ml. After replacing with argon again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, stir and heat to raise the temperature to 100°C, and control the temperature at 100-110°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evapora...

Embodiment 2

[0067] Synthesis of (Compound 2)

[0068] The synthetic route is as follows:

[0069]

[0070]

[0071] 1) Synthesis of Compound 2-1

[0072] 1000ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 32.15g of o-toluidine (purity 99%, 0.3mol), 64.44g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and xylene 400ml. After argon replacement again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, start stirring and heat up to 110°C, and control the temperature at 110-120°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated From the ...

Embodiment 3

[0077] Synthesis of (Compound 3)

[0078] The synthetic route is as follows:

[0079]

[0080] 1) Synthesis of compound 3-1

[0081] 1000ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 32.15g of o-toluidine (purity 99%, 0.3mol), 64.44g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and toluene 400ml. After replacing with argon again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, stir and heat to raise the temperature to 100°C, and control the temperature at 100-110°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated The f...

technical field

[0001] The invention relates to a novel organic electroluminescent material and its application in organic electroluminescent devices, belonging to the technical field of organic electroluminescent display. Background technique

[0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescence display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backli...

Examples

Embodiment 1

[0058] Synthesis of (Compound 1)

[0059] The synthetic route is as follows:

[0060]

[0061] 1) Synthesis of compound 1-2

[0062] 1000 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1 g (0.48 mol) of sodium tert-butoxide, 32.15 g (purity 99%, 0.3 mol) of o-toluidine, and 64.44 g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and toluene 400ml. After replacing with argon again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, stir and heat to raise the temperature to 100°C, and control the temperature at 100-110°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evapora...

Embodiment 2

[0067] Synthesis of (Compound 2)

[0068] The synthetic route is as follows:

[0069]

[0070]

[0071] 1) Synthesis of Compound 2-1

[0072] 1000ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 32.15g of o-toluidine (purity 99%, 0.3mol), 64.44g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and xylene 400ml. After argon replacement again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, start stirring and heat up to 110°C, and control the temperature at 110-120°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated From the ...

Embodiment 3

[0077] Synthesis of (Compound 3)

[0078] The synthetic route is as follows:

[0079]

[0080] 1) Synthesis of compound 3-1

[0081] 1000ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 32.15g of o-toluidine (purity 99%, 0.3mol), 64.44g of 3-bromo-9-benzene Base-9H-carbazole (purity 99%, 0.2 mol) and toluene 400ml. After replacing with argon again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were successively added. After the addition, stir and heat to raise the temperature to 100°C, and control the temperature at 100-110°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated The f...

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