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Soluble triphenylamine type organic micromolecular hole transport material and preparation method and application thereof

A technology of hole transport material and triphenylamine, which is applied in the field of organic electroluminescent display, can solve the problems of low efficiency, poor solubility, and shortened lifespan, and achieve the effects of simple synthesis route, convenient purification, and good film-forming properties

Active Publication Date: 2014-03-12
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently used small molecule hole transport materials mainly have the following problems: (1) poor solubility in common solvents, which is not conducive to the preparation of large-area films by the convenient and cheap spin coating method, which limits their commercial application; (2) small molecules The glass transition temperature (Glass Transition Temperature, Tg) of the compound is low, and crystallization often occurs during film formation or device use, resulting in reduced performance and shortened life of the device; (3) Small molecule materials are usually prepared by vacuum evaporation Functional thin film, less efficient
However, the disadvantage of polymeric hole transport materials is that they are difficult to synthesize and purify.

Method used

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  • Soluble triphenylamine type organic micromolecular hole transport material and preparation method and application thereof
  • Soluble triphenylamine type organic micromolecular hole transport material and preparation method and application thereof
  • Soluble triphenylamine type organic micromolecular hole transport material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of 4-(N,N-di-p-methylphenyl)aminobenzyl alcohol (compound 1)

[0033] Add 15.12g (50mmol) 4-(N,N-bis(4-methylphenyl)amino)benzaldehyde, 150mL dichloromethane (CH 2 Cl 2 ) and 50mL absolute ethanol (Et 2 OH) mixed solvent, after stirring and dissolving, add 1.91g (0.02mol) sodium borohydride (NaBH 4 ), stirred and reacted at room temperature (25°C) for 2 hours, and monitored the completion of the reaction with TLC (silica gel GF254 plate, developer: petroleum ether: ethyl acetate = 5:1), evaporated the solvent under reduced pressure, and distilled the product with 50mL CH 2 Cl 2 After dissolving, wash three times with deionized water, combine the organic layers and add anhydrous MgSO 4 After drying, the solvent was evaporated under reduced pressure to obtain a green viscous liquid. Compound 1 (white solid, 13.62 g, yield 90%) was obtained after solidification with n-pentane.

Embodiment 2

[0034] Embodiment 2: the synthesis of triphenylphosphine hydrobromide (compound 2)

[0035] Add 100mL tetrahydronaphthalene to a 250mL four-neck flask, slowly drop in 40mL bromine (Br 2 ), catalyzed by a small amount of Fe powder, bubbles are generated, after washing the bottle of HBr gas generated by tetrahydronaphthalene, it is passed into 500mL ether solution containing 21.03g (0.08mol) triphenylphosphine, and stirred at room temperature to generate The white triphenylphosphine hydrobromide solid was suction filtered after the reaction, the product was washed with diethyl ether, and then recrystallized with dichloromethane and diethyl ether to obtain the product (white solid, 17.48g, yield 64%). Mp.200~202℃.

Embodiment 3

[0036] Example 3: Synthesis of 4-(N,N-di-p-methylphenyl)aminobenzyltriphenylphosphine hydrobromide (compound 3)

[0037] N 2 Under protection, add 2.39g (8mmol) 4-(N,N-di-p-methylphenylamino) benzyl alcohol and 5.40g (16mmol) triphenylphosphine hydrobromide to a 100mL four-neck flask, add 60mL Chloroform (CHCl 3 ) as a solvent, stirred and dissolved, heated to reflux temperature (61°C) and stirred for 4 hours. TLC (silica gel GF254 plate, developer is petroleum ether: ethyl acetate = 5:1) to monitor the completion of the reaction, the solvent was evaporated under reduced pressure to obtain a light green oil, which was washed with ether and solidified to obtain a white powder product compound 3 ( White solid, 4.77g, yield 96%).

[0038] Synthesis of 4-(N,N-Di-p-methylphenyl)aminophenylallyltriphenylphosphine Hydrobromide

[0039]

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Abstract

The invention discloses a soluble triphenylamine type organic micromolecular hole transport material and a preparation method and application thereof. According to the triphenylamine type organic micromolecular hole transport material, dendrons containing triphenylamine groups are introduced onto different cores, so that the prepared hole transport material has certain solubility and can be purified by a solution method. The triphenylamine type organic micromolecular hole transport material disclosed by the invention can be prepared through firstly synthesizing different modules, namely cores and dendrons, and then correspondingly synthesizing respectively by adopting Wittig reaction, so that routes of synthesis are relatively simple, and the purification is convenient. The triphenylamine type organic micromolecular hole transport material has an important application prospect in organic electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescence display. It specifically relates to a soluble triphenylamine organic small molecule hole transport material and a preparation method thereof, and the invention also relates to the application of the molecular material in organic electroluminescent devices. Background technique [0002] Hole-Transport Materials (HTMs) are an important class of organic photoelectric functional materials, which can effectively improve the injection efficiency and transport efficiency of holes in devices. Due to the advantages and disadvantages of small molecule hole transport materials and polymer hole transport materials, seeking new hole transport materials with excellent performance has always been a research hotspot in this field. The organic hole transport materials that have been researched and developed mainly include small molecule hole transport materials (molecular weight 500-2000) and polymer ho...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C209/68C07D209/86H01L51/54
Inventor 李祥高高文正王世荣肖殷刘西成
Owner TIANJIN UNIV
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