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Organic hole transport material, preparation method and applications thereof

A hole-transporting material and organic technology, used in organic chemistry, semiconductor/solid-state device manufacturing, electrical components, etc., and can solve problems such as poor film-forming performance, poor hole-transporting ability, and low glass transition temperature.

Inactive Publication Date: 2020-05-08
紫石能源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The main purpose of the present invention is to provide an organic hole transport material, its preparation method and its application, so as to solve the problems of poor hole transport ability, low glass transition temperature and poor film-forming performance of hole transport materials in the prior art

Method used

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  • Organic hole transport material, preparation method and applications thereof
  • Organic hole transport material, preparation method and applications thereof
  • Organic hole transport material, preparation method and applications thereof

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preparation example Construction

[0039] In another typical embodiment, the present invention provides a method for preparing an organic hole transport material. The preparation method includes: S1. First, under the protection of a rare gas (such as nitrogen, argon), weigh a certain The polished magnesium strips of high quality and the distilled first organic solvent are put into the reaction device, then the halogenated thiophene is added dropwise to carry out the first reaction, and finally the Grignard reagent of the halogenated thiophene is obtained; S2, in the rare gas ( Under the protection of such as nitrogen, argon), weigh a certain quality of halogenated triarylamine A and PDCl 2 (PPh 3 )2 Place in the reaction device, add the distilled second organic solvent and add the Grignard reagent of the halogenated thiophene prepared above while stirring to carry out the second reaction to obtain trithiophene aniline B; wherein, the halogenated thiophene is selected from 2- One of chlorothiophene, 2-bromothio...

Embodiment 1

[0061]

[0062] Weigh 2.528g of polished magnesium strips and place them in a three-necked flask, add 15mL of distilled tetrahydrofuran THF, pass through nitrogen for protection, add 5mL of 2-bromothiophene dropwise with a constant pressure funnel to carry out the first reflux reaction, and stop the reaction after 1h of reflux Grignard reagent for 2-bromothiophene. Then weigh 4.227g tribromotriphenylamine and 0.135g PdCl 2 (PPh 3 ) 2 In a three-necked flask, add 30mL THF and add the Grignard reagent of 2-bromothiophene while stirring, under the protection of nitrogen, heat for the second reflux reaction for 16h, add saturated ammonium chloride to quench the reaction, and then use chloroform The product obtained after quenching is extracted, and the product obtained by extraction is dried with anhydrous sodium acetate, and the eluent composed of n-hexane:dichloromethane with a volume ratio of 3:1 is used for column chromatography on the dried product. Analysis and purific...

Embodiment 2

[0064]

[0065] Weigh 0.613g trithiophene aniline B into a three-necked flask, add 10mL 1,-dichloroethane and 2mL DMF, and stir in an ice bath for 0.5h under the protection of nitrogen, then add 2mL oxychloride dropwise with a constant pressure funnel Phosphorus, heated for the third reflux reaction for 15h, then cooled and poured into ice water, and added 100mL saturated sodium acetate solution to quench the reaction, then extracted the quenched product with 50mL dichloromethane, and simultaneously carried out the organic layer After washing with water for several times, the extracted product was dried with anhydrous sodium sulfate, and finally purified by column chromatography with dichloromethane and ethyl acetate eluent with a volume ratio of 20:1. 0.53 g of product C, tris[4-(5-formyl-2-thienyl)phenyl]amine, was isolated as an orange-yellow solid in a yield of 73.3%. Among them, the infrared spectrum and NMR of tris[4-(5-formyl-2-thienyl)phenyl]amine C 1 H-NMR spectru...

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Abstract

The invention provides an organic hole transport material, a preparation method and applications thereof. The organic hole transport material is one or a plurality of materials selected from triarylamine-thiophene system compounds, wherein the structure is represented by a formula I, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8> and R<9> are respectively and independently selected from a hydrogenatom, a halogen atom, a formyl group, a carboxyl group, a C1-C6 substituted or unsubstituted alkyl group, a C2-C5 substituted or unsubstituted alkenyl group, a C3-C10 substituted or unsubstituted cycloalkyl group and a C6-C10 aryl group. By adopting the organic hole transport material, the problems of poor hole transport capacity, low glass-transition temperature and poor film-forming property ofthe hole transport material in the prior art are solved.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular, to an organic hole transport material, its preparation method and its application. Background technique [0002] The basic structure of an electroluminescent device (such as an organic light-emitting diode) is a simple "sandwich" device, that is, spin-coating, dip-coating or vacuum thermal evaporation of a luminescent material (light-emitting layer) on a conductive glass substrate (anode), The cathode material is then plated and connected to a power source. Electron transport layer (ETL) or / and hole transport layer (HTL) are introduced into organic electroluminescent devices to form a multi-layer structure device, which helps electron and hole injection to achieve a balance, and improves the stability and stability of organic light-emitting devices. efficiency and improve device performance. [0003] The basic function of the hole transport layer is to inc...

Claims

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Application Information

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IPC IPC(8): C07D333/22C07D333/40H01L51/50H01L51/54
CPCC07D333/22C07D333/40H10K85/655H10K50/15
Inventor 王权刘琦
Owner 紫石能源有限公司
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