Nitrogen-containing fused-heterocyclic compound and preparation method thereof

A technology of compound and fused heterocycle, which is applied in the field of OLED materials, can solve the problems of different performances, and achieve the effect of large steric hindrance, difficult rotation, and simple preparation method

Inactive Publication Date: 2020-02-04
HEZE UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Nitrogen-containing fused-heterocyclic compound and preparation method thereof
  • Nitrogen-containing fused-heterocyclic compound and preparation method thereof
  • Nitrogen-containing fused-heterocyclic compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] The synthetic method of nitrogen-containing condensed heterocyclic compound (1) is as follows:

[0029]

[0030] Under nitrogen protection with a flow rate of 20sccm, compound I (10.0g, 333.02g / mol, 30mmol), compound II (1.1eq, 8.16g, 247g / mol, 33.03mmol), sodium tert-butoxide (4eq, 11.54g, 96.1g / mol, 120.11mmol), tris(dibenzylideneacetone)dipalladium (0.05eq, 1.37g, 915g / mol, 1.5mmol), tri-tert-butylphosphine (0.05eq, 0.3g, 202.32g / mol , 1.5mol), toluene (100g) into the reaction flask, after the addition was completed, the temperature was raised to reflux and stirred for 5 hours, after the reaction was completed and cooled to room temperature, 100mL of water was added and stirred for 10 minutes, and the resulting mixture was filtered through diatomaceous earth to obtain an organic phase , the organic phase was dried with anhydrous magnesium sulfate and then spin-dried to obtain a crude product. The crude product was dissolved in dichloromethane and metha...

Embodiment 2

[0032]

[0033] The synthetic method of nitrogen-containing condensed heterocyclic compound (4) is as follows:

[0034]

[0035] Under nitrogen protection with a flow rate of 10sccm, compound Ⅰ (10.0g, 333.02g / mol, 30mmol), compound Ⅱ (1.1eq, 11.86g, 359.12g / mol, 33.03mmol), sodium tert-butoxide (4eq, 11.54g , 96.1g / mol, 120.11mmol), tris(dibenzylideneacetone) dipalladium (0.05eq, 1.37g, 915g / mol, 1.5mmol), tri-tert-butylphosphine (0.05eq, 0.3g, 202.32g / mol, 1.5mol), toluene (100g) were added to the reaction flask, after the addition was completed, the temperature was raised to reflux and stirred for 5 hours, after the reaction was completed and cooled to room temperature, 100 mL of water was added and stirred for 10 minutes, and the obtained mixture was filtered through diatomaceous earth and separated to obtain organic phase, the organic phase was dried with anhydrous magnesium sulfate and spin-dried to obtain a crude product. The crude product was dissolved in dichlo...

Embodiment 3

[0037]

[0038] The synthetic method of nitrogen-containing condensed heterocyclic compound (5) is as follows:

[0039]

[0040]Under nitrogen protection with a flow rate of 50sccm, compound I (10.0g, 333.02g / mol, 30mmol), compound II (1.1eq, 11.49g, 348.03g / mol, 33.03mmol), sodium tert-butoxide (4eq, 11.54g , 96.1g / mol, 120.11mmol), tris(dibenzylideneacetone) dipalladium (0.05eq, 1.37g, 915g / mol, 1.5mmol), tri-tert-butylphosphine (0.05eq, 0.3g, 202.32g / mol, 1.5mol), toluene (150g) were added to the reaction flask, after the addition was completed, the temperature was raised to reflux and stirred for 5 hours, after the reaction was completed and cooled to room temperature, 100 mL of water was added and stirred for 10 minutes, and the resulting mixture was filtered through diatomaceous earth and separated to obtain organic phase, the organic phase was dried with anhydrous magnesium sulfate and then spin-dried to obtain a crude product. The crude product was dissolved in ...

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PUM

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Abstract

The invention provides a nitrogen-containing fused-heterocyclic compound and a preparation method thereof and relates to the field of OLED (organic light emitting diode) materials. The structural formula of the compound is shown in the description, in the formula, R1, R2 and R3 are independently selected from hydrogen, heavy hydrogen, cyanogroup, halogen atoms, substituted or unsubstituted C1-C20straight-chain or branched alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbons and substituted or unsubstituted C5-C30 heterocyclic aromatic hydrocarbons. After being applied to an OLED device, the compound provided by the invention is capable of effectively increasing the utilization rate of excitons, reducing the voltage of the device, improving the current efficiency of the deviceand prolonging the service life of the device. The compound provided by the invention has a good application effect in OLED light-emitting devices and has a good industrial prospect. In addition, thecompound is simple in preparation method and possible in large-scale industrial production.

Description

technical field [0001] The invention relates to the field of OLED materials, in particular to a nitrogen-containing condensed heterocyclic compound and a preparation method thereof. Background technique [0002] At present, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with actual product application requirements, the luminous efficiency and service life of OLED devices Further improvement is required. The current research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to continuously improve the performance of OLED devices, not only the innovation of OLED device structure and manufacturing process is required, but also the continuous research and innovation of OLED photoelectric...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C09K11/06H01L51/50H01L51/54
CPCC07D487/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1088H10K85/615H10K85/6574H10K85/6572H10K50/11
Inventor 樊红莉李风海郭倩倩郭明晰
Owner HEZE UNIV
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