9, 9-bis(triphenyl amino) fluorine derivatives and preparation and use thereof

A triphenylamine-based and triphenylamine-based technology, which is applied in semiconductor/solid-state device manufacturing, electrical components, circuits, etc., can solve the problems that the hole transport layer has not been reported, the price of PEDOT is expensive, etc., and achieve good hole transport performance, Excellent electrochemical performance and high yield

Inactive Publication Date: 2005-07-06
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two materials can achieve the effect of reducing the light-up voltage, PEDOT is expensive, while CuPc will absorb red light, and new hole injection and transport materials need to be developed
[0004] Fluorene derivatives have been widely used as light-emitting layers of electroluminescent materials, but hole transport layers containing fluorene have not been reported

Method used

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  • 9, 9-bis(triphenyl amino) fluorine derivatives and preparation and use thereof
  • 9, 9-bis(triphenyl amino) fluorine derivatives and preparation and use thereof
  • 9, 9-bis(triphenyl amino) fluorine derivatives and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of 2,7,9,9-tetrakis(triphenylamino)fluorene (No. XB10)

[0027] Under the protection of argon gas, 338mg (1mmol) 2,7-dibromo-9-fluorenone, 3.43g (14mmol) triphenylamine and 91mg (1mmol) methanesulfonic acid were added to a 100mL reaction flask in sequence, and the gas in the reaction flask After replacing with an inert gas, the mixture was heated to 140°C and stirred at this temperature for about 8 hours to obtain a reddish brown solution, cooled to room temperature, dissolved in dichloromethane, washed with saturated aqueous sodium carbonate solution and dried with anhydrous sodium sulfate. After concentration, column chromatography (silica gel, petroleum ether / dichloromethane / ethyl acetate elution) separated 0.633 g of 2,7-dibromo-9,9-bis(triphenylamino)fluorene with a yield of 78.1%.

[0028] Add 3.24g (10mmol) of triphenylamine bromide to n-BuLi at -78°C. After reacting for 1 hour, add 2.82g (15mmol) of triisopropanol borate, stir for 2 hours, raise ...

Embodiment 22

[0031] Example 22 Synthesis of 7-bis(2-naphthyl)-9,9-bis(triphenylamino)fluorene

[0032] The preparation method of 2,7-dibromo-9,9-bis(triphenylamino)fluorene is the same as in Example 1.

[0033] Under the protection of argon gas, 10.35g (50mmol) 2-bromonaphthalene, 1.32g (55mmol) magnesium chips and 100mL tetrahydrofuran were sequentially added to the reaction flask. After the reaction was refluxed for 4 hours, it was cooled to -78℃, and 14.1g (75mmol) ) Triisopropanol borate, stir for 2 hours, raise the temperature to room temperature, and continue stirring for 10 hours to obtain a green solution. Add 500 mL of 2N hydrochloric acid solution, stir at room temperature for 2 hours, and then add water. After extraction with ether, washing with saturated brine, drying with anhydrous sodium sulfate and concentration, toluene was recrystallized to obtain 3.18 g of 2-naphthyl monoborate with a yield of 37%.

[0034] Under the protection of argon, in a 100mL reaction flask, sequentiall...

Embodiment 3 3

[0036] Example 3 Fabrication and performance of light-emitting devices when triphenylamine-fluorene compound is used as the hole-transporting layer of TPD

[0037] Use TPD as the hole transport layer, the triphenylamine-fluorene compound (No. XB10) obtained in the foregoing Example 1 as the hole transport layer, Alq 3 It is the light-emitting layer and the electron transport layer, using ITO glass as the anode, aluminum fluoride as the electron injection layer, and aluminum as the cathode. The light-emitting device is prepared by vacuum evaporation. See the voltage and brightness curve of the device figure 1 .

[0038] The symbols in the figure are:

[0039]

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Abstract

The invention relates to a method for preparing 9,9-bis(trianilino) fluorene derivatives and their use. The derivatives can be prepared by Suzuki coupling of dihalogenated 9,9-bis(trianilino) fluorene and aromatic ring or heterocyclo-boric acid or its ester. And the derivatives can be used as auxiliary hole transportation materials of organic light emitting diode and can reduce the starting voltage of device.

Description

Technical field [0001] The present invention relates to a new type of 9,9-bis(triphenylamino) fluorene derivative, which is prepared from commercially available triphenylamine and fluorenone as starting materials. The compound provided by the present invention is a kind of hole-transporting materials with excellent performance. Combining it with traditional hole-transporting materials such as TPD and NPB can greatly reduce the lighting voltage of light-emitting diodes, and improve the brightness and current efficiency. No significant effect. Background technique [0002] Organic electroluminescent diodes (OLEDs) have received close attention from the scientific and technological circles and the industry because of their huge application prospects in various displays. In the past two decades, many famous research institutions in the world, such as Max Planck Institute, Princeton University and Cambridge University, have carried out a number of in-depth studies in materials synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C211/61C07D207/335C07D209/14C07D209/86C07D333/20H01L51/30
Inventor 房强姜标徐兵付海涛
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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