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Silicon-containing heterocyclic compound and organic electroluminescent element containing same

A compound and silicon heterocycle technology, applied in the field of organic electroluminescence, can solve the problems of reducing the quantum yield of the blue light system, aggravating the quenching of molecular fluorescence, and low quantum efficiency of luminescence, so as to improve the internal quantum efficiency and increase the electron cloud Effect of density, low sublimation temperature

Active Publication Date: 2022-01-11
SHANGHAI BAYI SPACE ADVANCED MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, blue light materials still have the problems of low luminous quantum efficiency and poor color purity.
The main reason for this situation is that blue light comes from the transition between energy levels with a wide energy gap, and organic compounds with wide band gaps have certain difficulties in molecular design, and secondly, there are strong blue light materials in the system. The π-π bond interaction has strong charge transfer characteristics, so that there are more non-radiative relaxation channels in the wide band gap, which intensifies the fluorescence quenching between molecules and reduces the quantum yield of the blue light system

Method used

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  • Silicon-containing heterocyclic compound and organic electroluminescent element containing same
  • Silicon-containing heterocyclic compound and organic electroluminescent element containing same
  • Silicon-containing heterocyclic compound and organic electroluminescent element containing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] The preparation method of compound A1, comprises the steps:

[0087] Step 1: Preparation of Compound Int.-1

[0088]

[0089] Under nitrogen protection, 75.0mmol of 1,4-diiodo-2,5-dimethoxybenzene (CAS: 51560-21-5) was dissolved in 60mL of THF and 30mL of triethylamine, and 150.0mmol of p-methoxyphenylacetylene, 7.5mmol of cuprous iodide, 0.75mmol of PdCl 2 (PPh 3 ) 2 Catalyst, stirred and reacted for 12 hours, after the reaction was completed, filtered, the filtrate was concentrated to dryness under reduced pressure, separated and purified by silica gel column, and Int.-1 was obtained as a yellow solid with a yield of 96%.

[0090] The second step: the preparation of compound Int.-2

[0091]

[0092] 50.0 mmol of Int.-1 prepared in the first step was dissolved in 100 mL of dry dichloromethane, and under nitrogen protection, a solution of 0.1 mol of iodine dissolved in dichloromethane was added dropwise, stirred for 3 hours, and 50 mL of 10% Sodium thiosulfat...

Embodiment 2

[0112] The preparation method of compound A2, comprises the steps:

[0113] The first step: preparation of compound Int.-7

[0114]

[0115] The Pd(PPh 3 ) 4 Mix, then add 60mL of THF and 20mL of water, stir and raise the temperature to reflux for 12 hours, cool to room temperature, add 20mL of ethanol, filter, wash the filter cake with water and ethanol, separate and purify with silica gel column to obtain the intermediate Int. -7, yield 82%.

[0116] The second step: the preparation of compound Int.-8

[0117]

[0118] Referring to the synthesis method in the sixth step of Example 1, only Int.-5 in the sixth step of Example 1 was replaced with Int.-7 to prepare Int.-8 with a yield of 84%.

[0119] The third step: the preparation of compound A2

[0120]

[0121] Referring to the preparation method in the seventh step of Example 1, only the intermediate Int.-6 in the seventh step of Example 1 was replaced with the intermediate Int.-8 prepared in the previous step...

Embodiment 3

[0125] The preparation method of compound A11, comprises the steps:

[0126] Step 1: Preparation of Compound Int.-9

[0127]

[0128] 20.0mmol of Int.-4 prepared in Example 1 was dissolved in 40.0mL of dry THF, cooled to -78°C with liquid nitrogen, then 17.6mL of 2.5M n-butyllithium n-hexane solution was added dropwise, and the reaction was stirred for 1 hour , dropwise added 48.0mmol of trimethylchlorosilane, stirred for 1 hour, raised to room temperature, added 20mL of saturated ammonium chloride aqueous solution, extracted with ethyl acetate, collected the organic phase, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. Separation and purification with a silica gel column gave the intermediate Int.-9 with a yield of 90%.

[0129] The second step: the preparation of compound Int.-10

[0130]

[0131] Referring to the synthesis method in the sixth step of Example 1, only Int.-5 in the sixth step of Example 1 was replaced with Int.-9...

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Abstract

The invention discloses a silicon-containing heterocyclic compound and an organic electroluminescent element containing the same. The structural general formula of the silicon-containing heterocyclic compound is shown as a formula I. The introduction of multi-element heterocyclic rings not only increases the electron cloud density of molecules, but also increases the conjugation area of the molecules to improve the internal quantum efficiency, and the addition of silicon-containing groups has shorter light-emitting wavelength and narrower peak width compared with those of compounds in the prior art; meanwhile, the silicon-containing heterocyclic compound hinders the generation of an excitation-excitation compound between organic molecules, and increases the internal electron density and stability, thereby improving the efficiency of an organic electroluminescent device comprising the compound and prolonging the life of the organic electroluminescent device comprising the compound.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescence, more specifically, to a silicon-containing heterocyclic compound, the application of the silicon-containing heterocyclic compound in the preparation of organic electroluminescent elements, and an organic electroluminescent element containing the compound . Background technique [0002] Most of the substances used in organic electroluminescent elements are pure organic substances, or organic metal complexes formed by organic substances and metals, which can be divided into hole injectors, hole transporters, luminescent substances, electron transporters, Electron injectors, etc. Here, organic substances with relatively low ionization energy are mainly used as hole injectors or hole transporters, and organic substances with relatively high electronegativity are mainly used as electron injectors or electron transporters. In addition, the material used as the luminescence...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07F7/0814C09K11/06C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/12Y02E10/549
Inventor 韩洪波赵雷曹建华唐伟王志杰谢佩李程辉徐先锋
Owner SHANGHAI BAYI SPACE ADVANCED MATERIAL CO LTD
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