Organic semiconductor material containing triphenylamine, its preparation method and application

Abstract

The present invention relates to the technical field of organic materials, and provides a triphenylamine-containing organic semiconductor material, a preparation method and applications thereof. The triphenylamine-containing organic semiconductor material has the following structural formula I, wherein the structural formula of the triphenylamine-containing organic semiconductor material comprises a triphenylamine unit, a diphenylphosphinoxy unit and a fluorenyl unit. According to the present invention, a carrier delivery rate is substantially increased through the triphenylamine and the diphenylphosphinoxy so as to improve luminescent property; and the triphenylamine unit, the diphenylphosphinoxy unit and the fluorenyl unit form a 9,9-bis(triphenylamine)spirofluorene structure, such that the triphenylamine-containing organic semiconductor material has excellent thermal stability. The preparation method for the triphenylamine-containing organic semiconductor material has characteristics of simple operation and low cost, and is suitable for industrial production.

Description

technical field

[0001] The invention belongs to the technical field of organic materials, and in particular relates to a triphenylamine-containing organic semiconductor material, its preparation method and application. Background technique

[0002] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted the attention of scientists around the world, and related companies and laboratories are conducting research and development of this technology. As a new type of LED technology, organic electroluminescent devices with the characteristics of active light emission, lightness, thinness, good contrast, low energy consumption, and flexible devices can put forward higher requirements for materials.

[0003] At present, during the production and actual work of OLED, it will be a...

Examples

preparation example Construction

[0028] The embodiment of the present invention further provides the method for preparing the above-mentioned organic semiconductor material, including the following steps:

[0029] Step S01, providing 9,9-bis(triphenylamino)-2,7-dibromofluorene represented by structural formula II

[0030]

[0031] Step S02, preparing an organic semiconductor material containing triphenylamine

[0032] Add the alkyl derivative of lithium to the dissolved 9,9-bis(triphenylamino)-2,7-dibromofluorene represented by the structural formula II under the conditions of anhydrous and oxygen-free and a temperature of -78°C to -70°C In an organic solvent, stir and react for 1 hour to 5 hours, add diphenyl phosphorus chloride, adjust the system temperature to 10°C-30°C, react for 3 hours to 12 hours, collect the reaction product and purify it, and react the purified Dissolving the product in an organic solvent, adding an oxidizing agent, and reacting for 1 to 12 hours to obtain an organic semiconducto...

Embodiment 2

[0046] Embodiments of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene ( DMTTPOF) has the following structural formula:

[0047]

[0048] Embodiments of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene ( DMTTPOF) preparation method, comprises the steps:

[0049] Step 1. Preparation of 9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene 2,7-dibromofluorene:

[0050] Under the protection of argon, 7mmol of 2,7-dibromofluorenone, 98mmol of N,N-bis(4-cyanophenyl)anilino and 7mmol of methanesulfonic acid were added to the reactor, at 140°C The reaction was stirred for 6 hours, the reaction was stopped and cooled to 15°C, extracted with dichloromethane, washed with saturated sodium bicarbonate solution and distilled water respectively, and the organic layer was concentrated to obtain a blue solid. After the crude product was separ...

Embodiment 2

[0058] Example of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene (DBTTPOF) has the following structural formula:

[0059]

[0060] Example of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene (DBTTPOF) preparation method, comprises the steps:

[0061] Step 1. Preparation of 9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene 2,7-dibromofluorene:

[0062] Under the protection of argon, 7mmol of 2,7-dibromofluorenone, 98mmol of N,N-bis(4-cyanophenyl)anilino and 7mmol of tert-butylsulfonic acid were added to the reactor, at 140 Stir the reaction at ℃ for 8 hours, stop the reaction and cool to 25 ℃, extract with dichloromethane, wash with saturated sodium bicarbonate solution and distilled water respectively, and concentrate the organic layer to obtain a blue solid. After the crude product was separated and purified...

technical field

[0001] The invention belongs to the technical field of organic materials, and in particular relates to a triphenylamine-containing organic semiconductor material, its preparation method and application. Background technique

[0002] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted the attention of scientists around the world, and related companies and laboratories are conducting research and development of this technology. As a new type of LED technology, organic electroluminescent devices with the characteristics of active light emission, lightness, thinness, good contrast, low energy consumption, and flexible devices can put forward higher requirements for materials.

[0003] At present, during the production and actual work of OLED, it will be a...

Examples

preparation example Construction

[0028] The embodiment of the present invention further provides the method for preparing the above-mentioned organic semiconductor material, including the following steps:

[0029] Step S01, providing 9,9-bis(triphenylamino)-2,7-dibromofluorene represented by structural formula II

[0030]

[0031] Step S02, preparing an organic semiconductor material containing triphenylamine

[0032] Add the alkyl derivative of lithium to the dissolved 9,9-bis(triphenylamino)-2,7-dibromofluorene represented by the structural formula II under the conditions of anhydrous and oxygen-free and a temperature of -78°C to -70°C In an organic solvent, stir and react for 1 hour to 5 hours, add diphenyl phosphorus chloride, adjust the system temperature to 10°C-30°C, react for 3 hours to 12 hours, collect the reaction product and purify it, and react the purified Dissolving the product in an organic solvent, adding an oxidizing agent, and reacting for 1 to 12 hours to obtain an organic semiconducto...

Embodiment 2

[0046] Embodiments of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene ( DMTTPOF) has the following structural formula:

[0047]

[0048] Embodiments of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene ( DMTTPOF) preparation method, comprises the steps:

[0049] Step 1. Preparation of 9,9-bis(N,N-bis(4-(5-methylthiophen-2-yl)phenyl)anilino)fluorene 2,7-dibromofluorene:

[0050] Under the protection of argon, 7mmol of 2,7-dibromofluorenone, 98mmol of N,N-bis(4-cyanophenyl)anilino and 7mmol of methanesulfonic acid were added to the reactor, at 140°C The reaction was stirred for 6 hours, the reaction was stopped and cooled to 15°C, extracted with dichloromethane, washed with saturated sodium bicarbonate solution and distilled water respectively, and the organic layer was concentrated to obtain a blue solid. After the crude product was separ...

Embodiment 2

[0058] Example of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene (DBTTPOF) has the following structural formula:

[0059]

[0060] Example of the present invention 2,7-bis(diphenylphosphineoxy)-9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene (DBTTPOF) preparation method, comprises the steps:

[0061] Step 1. Preparation of 9,9-bis(N,N-bis(4-(5-tert-butylthiophen-2-yl)phenyl)anilino)fluorene 2,7-dibromofluorene:

[0062] Under the protection of argon, 7mmol of 2,7-dibromofluorenone, 98mmol of N,N-bis(4-cyanophenyl)anilino and 7mmol of tert-butylsulfonic acid were added to the reactor, at 140 Stir the reaction at ℃ for 8 hours, stop the reaction and cool to 25 ℃, extract with dichloromethane, wash with saturated sodium bicarbonate solution and distilled water respectively, and concentrate the organic layer to obtain a blue solid. After the crude product was separated and purified...

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