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A self-doped conjugated phenolic amine hole transport material and its preparation and application

A technology of hole transport material and conjugated phenolic amine, which is applied in the field of self-doping conjugated phenolic amine hole transport material and its preparation and application, can solve the problems of cost increase and achieve the goal of preventing interface erosion and high conductivity Effect

Active Publication Date: 2019-04-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the complex doping process also greatly increases the cost

Method used

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  • A self-doped conjugated phenolic amine hole transport material and its preparation and application
  • A self-doped conjugated phenolic amine hole transport material and its preparation and application
  • A self-doped conjugated phenolic amine hole transport material and its preparation and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] 4,7-dibromo-benzothiadiazole (0.59g, 2.00mmol), 4,4-dimethoxydiphenyl-4-boronic acid-aniline (1.75g, 5.00mmol), tetrakistriphenylphosphine Palladium (230mg, 0.2mmol) was added to a mixed solvent of anhydrous toluene (20mL) and ethanol (10mL), and 5mL of 2M sodium carbonate aqueous solution was added under the protection of nitrogen, and the reaction was refluxed for 8h. The reaction product was separated and purified to obtain intermediate Product 1.45g, yield 98%. Dissolve the above product (0.5 g) in 15 ml of dichloromethane solution, exhaust nitrogen gas for 20 min, add 6 mL of boron tribromide at -78 ° C, gradually raise to room temperature, and react for 72 h, add an appropriate amount of ice water to quench excess boron tribromide, extract the product three times with 30mL ethyl acetate, collect the organic phase, remove the solvent under reduced pressure, and separate with a silica gel column, using petroleum ether / ethyl acetate=1:1 (v / v) as eluent , and then wa...

Embodiment 2

[0049] Dissolve Spiro-OMeTAD (0.3g) in 10ml of dichloromethane solution, exhaust nitrogen for 20min, add 3mL of boron tribromide at -78°C, gradually raise to room temperature, and react for 48h, then add appropriate amount of methanol to quench excess boron tribromide, extract the product three times with 30mL ethyl acetate, collect the organic phase, remove the solvent under reduced pressure, and separate with a silica gel column, using petroleum ether / ethyl acetate=1:3 (v / v) as eluent , the crude product was obtained, and then washed 3 times with petroleum ether to obtain 0.25 g of gray-green powder, with a yield of 80%. 1 H-NMR (600MHz, DMSO-d 6 )δ9.40-9.18(s,8H),7.48-7.32(d,J=12Hz,4H),6.83-6.70(m,16H),6.68-6.61(m,16H),6.61-6.57(dd,J =1.8,6Hz,4H),6.20-6.06(s,4H).C 73 h 52 N 4 NaO 4 [M + Na + ] + 1135.3677, found 1135.3669. The structural formula of the product obtained is as follows:

[0050]

[0051] The resulting product has a solubility greater than 200mg / mL i...

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PUM

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a self-doping conjugated phenolic amine hole transport material as well as its preparation and application. The self-doped conjugated phenolic amine hole transport material has the following general structural formula shown in (1) or (2), wherein X and R are conjugated aromatic rings or conjugated heterocyclic bridging groups. The conjugated phenolic amine derivatives obtained in the present invention are dissolved in large polar solvents such as dimethyl sulfoxide and alcohol, and have good film-forming properties. In multilayer devices, the interface of low polar solvents such as toluene or chlorobenzene can be prevented. erosion. The material has a stable free radical signal, and its mechanism is self-doping induced by conjugated phenolic amines. It has good hole transport performance without additional dopants, and can be applied to fields such as organic optoelectronic devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a self-doping conjugated phenolic amine hole transport material and its preparation and application. Background technique [0002] In multilayer organic electronic device structures, in order to overcome the hole-charge transport barrier, a hole-transport material (HTM) layer is usually introduced, which functions to transport holes and block electrons, thereby improving the efficiency of the device. [0003] Doped poly(3,4-ethylenedioxythiophene / polystyrene sulfonate (PEDOT:PSS) has high electrical conductivity and convenient solution processing characteristics, and is widely used as a hole in organic electronic devices. Inject / transfer material. However, the corrosion of metal electrodes by PEDOT:PSS due to the use of dopants was confirmed to reduce the device lifetime. [0004] Dopants are an effective way to increase the conductivity of ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/14C07C213/00C07C215/82
CPCC07C213/00C07D285/14H10K85/633H10K85/656C07C215/82Y02E10/549
Inventor 李远邱学青薛雨源
Owner SOUTH CHINA UNIV OF TECH
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