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Organic electroluminescent material containing element germanium and organic luminescent device

An electroluminescence, elemental technology, applied in luminescent materials, electro-solid devices, germanium organic compounds, etc., can solve the problems of high driving voltage, low lifespan, low luminous efficiency, etc., improve the glass transition temperature, and avoid aggregation and quenching. , the effect of high luminous efficiency and service life

Inactive Publication Date: 2018-06-29
CHANGCHUN HYPERIONS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the commonly used anthracene-based fluorescent blue light materials, the luminous efficiency is low and the driving voltage is high; while for phosphorescent blue light materials such as Firpic, the lifespan is low

Method used

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  • Organic electroluminescent material containing element germanium and organic luminescent device
  • Organic electroluminescent material containing element germanium and organic luminescent device
  • Organic electroluminescent material containing element germanium and organic luminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Embodiment 1: the synthesis of compound 35

[0070]

[0071] Step1. Add carbazole 100mmol, 2,7-dibromo-9,9-dimethylfluorene 100mmol, potassium tert-butoxide 300mmol, Pd 2 (dba) 3 1mmol, ultrasonically deoxygenated xylene, stirred and dissolved, replaced the air three times, added 4% (4mmol, 50% m / V) of the ligand tri-tert-butylphosphine, replaced the air three times again, and refluxed for 6h. Cool to room temperature, add enough dichloromethane to completely dissolve the product, pass through a small amount of silica gel funnel, and remove catalyst and salt. The filtrate was concentrated to a viscous state and subjected to column chromatography to obtain 35-1 75 mmol.

[0072] Step2. Dissolve 75mmol 35-1 100mmol in anhydrous THF, cool down to -78 degrees Celsius, and add 1.5 equivalents of n-butyllithium under the protection of argon, and react for 1h. The temperature was slowly raised to room temperature, and triphenylchlorogermane was added, and the reaction w...

Embodiment 2

[0073] Embodiment 2: the synthesis of compound 37

[0074]

[0075] Step1. Dissolve 100 mmol of 3-bromo-9,9-dimethylfluorene in anhydrous THF, cool down to -78 degrees Celsius, and add 1.5 equivalents of n-butyllithium under the protection of argon, and react for 1 h. The temperature was slowly raised to room temperature, triphenylchlorogermane was added, and the reaction was completed for 1 h. The reaction solution was quenched with saturated ammonium chloride aqueous solution, extracted with EtOAc, washed, dried, and passed through a silica gel column to obtain 3750 mmol of the product.

Embodiment 3

[0076] Embodiment 3: the synthesis of compound 39

[0077]

[0078] Step1. Dissolve 100mmol 2,8-dibromo-dibenzofuran in THF and cool down to -78°C. Under the protection of nitrogen, 2 equivalents of LDA and 1 equivalent of diisopropylamine were added, and the obtained brown solution was stirred at this temperature for 2 hours, and 1 equivalent of iodine in THF solution was slowly added, and the reaction solution was gradually warmed to room temperature, and reaction 2 Hour. The pH was adjusted to 7 with 2N HCl, and the resulting solution was extracted three times with EA, washed, dried, and subjected to silica gel column chromatography to obtain 45 mmol of the product 39-1.

[0079] Step2.. Add 39-1 45mmol to a mixed solvent of toluene, ethanol, and water, add 1 equivalent of phenylboronic acid, 3 equivalents of sodium carbonate, and 0.01 equivalent of tetrakistriphenylphosphine palladium under nitrogen protection, and react at reflux temperature After 5h, the reaction wa...

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Abstract

The invention provides an organic electroluminescent material containing element germanium and an organic luminescent device, and belongs to the technical field of organic photoelectric materials. Theorganic electroluminescent material comprises a germanium structure, and effectively breaks off conjugation, so that triple-state energy level is higher, an energy barrier between HOMO and LOMO is greater, and use as a blue light-emitting material is facilitated better; benzothiophene and benzofuran in the structure are electron-withdrawing groups, so that balance of transmission of electrons andtransmission of the carrier is facilitated. A carbazole structure in the structure is an electron donating group, so that balance of transmission of a cavity and transmission of the carrier is facilitated. Fluorene in the structure has certain rigidity, so that a glass transition temperature is increased in a facilitated mode. Besides, triphenyl germanium is a large non-planar group, so that a pi-pi accumulating effect of molecules is avoided; the compound is not liable to crystallize, so that excitons are prevented from being gathered and quenched in a crystallization region. Compared with the prior art, the compound has the advantages of relatively high light-emitting efficiency and longer service life while applied to the organic luminescent device, especially used in a light-emittinglayer.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to an organic electroluminescent material containing germanium and an organic light emitting device. Background technique [0002] Organic electroluminescence refers to the phenomenon that organic materials are excited by electric current and electric field to emit light under the action of electric field. Organic light-emitting diodes (OLEDs) are a next-generation display technology that utilizes this phenomenon to realize displays. Since Tang C.W. and Vanslyke S.A. of American Kodak Company produced the first organic electroluminescent device with excellent performance in 1987, organic electroluminescent displays have attracted great interest due to their advantages. [0003] At present, due to their excellent performance, red and green light-emitting materials have been used commercially, while the wide energy gap and high thermal stability of blue-light ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/30C09K11/06H01L51/54
CPCC09K11/06C07F7/30C09K2211/1088C09K2211/1092C09K2211/1044C09K2211/1033C09K2211/1007C09K2211/1011C09K2211/1014H10K85/615H10K85/655H10K85/636H10K85/626H10K85/654H10K85/633H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 孙可一蔡辉
Owner CHANGCHUN HYPERIONS TECH CO LTD