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Compound, preparation method thereof and light-emitting diode

A technology of light-emitting diodes and compounds, which is applied in the fields of silicon-organic compounds, chemical instruments and methods, luminescent materials, etc., can solve the problems of aggravating the dissociation of organic functional materials, low dissociation energy, and screen burn-in.

Active Publication Date: 2020-06-05
GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, OLEDs still have disadvantages, including problems such as burn-in and color shift, which are mainly caused by the poor stability of the compounds used in OLEDs, especially in the presence of holes, electrons, polarization, etc. in the electric field. This will further intensify the dissociation of organic functional materials in the case of positive and negative charges such as
At present, carbazole groups and carrier groups are mostly obtained by forming carbon-nitrogen single bonds to meet the requirements of carrier transport performance in the functional layer. However, the dissociation energy of carbon-nitrogen single bonds in the negative ion state Very low, so that the carbon-nitrogen single bond is easy to break, causing the degradation of the prepared functional material, thus affecting the service life

Method used

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  • Compound, preparation method thereof and light-emitting diode
  • Compound, preparation method thereof and light-emitting diode
  • Compound, preparation method thereof and light-emitting diode

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preparation example Construction

[0061] The present invention also proposes a preparation method of the compound. The compound is prepared by reacting a carbazole raw material and a carrier raw material. The carrier raw material is a halide having a carrier group. The molecular formula of the carbazole raw material is:

[0062]

[0063] The invention realizes the preparation of the compound through the SUZUKI coupling reaction of carbazole raw materials and carrier raw materials. The catalytic cycle process of the SUZUKI coupling reaction is generally regarded as the oxidation-addition of Pd(0) to halogenated aromatic hydrocarbons to form Pd(II) complex 1, followed by the reaction with activated boronic acid to generate Pd(II) through transmetalation reaction. The complex 2, through the reduction-elimination reaction, generates the compound and Pd(0), thus realizing the preparation of the compound.

[0064] In one embodiment of the present invention, the preparation method of the compound comprises the fol...

Embodiment 1

[0076] Such as Figure 4 The schematic diagram of the preparation of compound M1 is shown, and the preparation method of compound M1: adopt SUZUKI coupling reaction, add 6mmol carbazole raw material 1, 2mmol 1,3,5-triiodobenzene, 0.2mmol Tetrakistriphenylphosphopalladium Pd(PPh 3 ) 4 , 6mmol potassium carbonate K 2 CO 3 , add mixed solvent toluene / ethanol / water (V / V / V=8:1:1) 80ml under nitrogen atmosphere, reflux reaction at 120°C for 12h; after the reaction is completed, cool to room temperature, pour the reaction solution into water, Extracted with dichloromethane for 3 times, the extracted organic layer liquid was washed with concentrated brine and distilled water successively, passed through anhydrous MgSO 4 Drying, filtering, and removing the solvent by rotary evaporation, using n-hexane / dichloromethane as the eluent, using silica gel chromatography column for separation and purification, rotary evaporation to remove the solvent to collect the resulting product, which...

Embodiment 2

[0079] Such as Figure 6 The schematic diagram of the preparation of compound M19 is shown, and the preparation method of compound M19: adopt SUZUKI coupling reaction, add 4mmol carbazole raw material 1 and 2mmol 9,9-dimethyl-2,7- Diiodofluorene, 0.1mmol tetrakistriphenylphosphopalladium Pd(PPh 3 ) 4 , 4mmol potassium carbonate K 2 CO 3 , add mixed solvent toluene / ethanol / water (V / V / V=8:1:1) 80ml under nitrogen atmosphere, reflux reaction at 120°C for 12h; after the reaction is completed, cool to room temperature, pour the reaction solution into water, Extracted with dichloromethane for 3 times, the extracted organic layer liquid was washed with concentrated brine and distilled water successively, passed through anhydrous MgSO 4 Dry, filter, and remove the solvent by rotary evaporation, use n-hexane / dichloromethane as the eluent, separate and purify by using a silica gel chromatography column, and collect the product obtained by rotary evaporation to remove the solvent, wh...

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Abstract

The invention discloses a compound, a preparation method thereof and a light emitting diode. The molecular structure of the compound comprises a carrier group and a carbazole group, the carrier groupis an organic group, the carbazole group comprises a benzene ring, and the carbazole group is bonded to the carrier group through the benzene ring. When the compound is applied to preparation of a functional layer, it can be understood that the stability of the prepared functional layer can be improved through the technical scheme, and therefore the service lifetime of a device is guaranteed.

Description

technical field [0001] The invention relates to the technical field of photoelectric functional materials, in particular to a compound, a preparation method thereof and a light emitting diode. Background technique [0002] Organic light-emitting diode (OLED) displays are gradually becoming the mainstream of high-end displays, such as mobile phones, TVs, lighting and wearable display devices. Nevertheless, OLEDs still have disadvantages, including problems such as burn-in and color shift, which are mainly caused by the poor stability of the compounds used in OLEDs, especially in the presence of holes, electrons, polarization, etc. in the electric field. This will further intensify the dissociation of organic functional materials in the case of positive and negative charges such as electrons. At present, carbazole groups and carrier groups are mostly obtained by forming carbon-nitrogen single bonds to meet the requirements of carrier transport performance in the functional la...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07F7/08C07D487/06C07F9/6561C09K11/06H01L51/50H01L51/54
CPCC07D519/00C07F7/0812C07D487/06C07F9/65616C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1048C09K2211/1059C09K2211/1092H10K85/624H10K85/615H10K85/654H10K85/6576H10K85/6572H10K85/657H10K85/40H10K50/15H10K50/16H10K50/11
Inventor 周兴邦
Owner GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD