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A star-shaped blue fluorescent molecule and its synthesis method and application

A technology of blue fluorescence and synthesis method, applied in the field of organic optoelectronics, can solve the problems of poor repeatability, non-uniform molecular weight, uncertain structure, etc., and achieve the effects of good film formation, uniform molecular weight and definite structure

Active Publication Date: 2020-12-01
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] S, S-dioxy-dibenzothiophene has good electron transport properties, and blue-light polymers based on S, S-dioxy-dibenzothiophene units have achieved high device efficiency, but such polymer materials It has the defects of uncertain structure, poor repeatability and non-uniform molecular weight

Method used

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  • A star-shaped blue fluorescent molecule and its synthesis method and application
  • A star-shaped blue fluorescent molecule and its synthesis method and application
  • A star-shaped blue fluorescent molecule and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Preparation of Compound 1

[0041] Under nitrogen protection, add 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9- Dihexylfluorene (5.86g, 10mmol), 2-bromo-9,9-dihexylfluorene (4.13g, 10mmol), potassium carbonate (3.45g, 25mmol), tetrakis(triphenylphosphine) palladium (0.58g, 0.5 mmol), 12ml deionized water and 120ml toluene, heated to 80°C for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and after removing the organic phase solvent, the crude product was purified by column chromatography using petroleum ether as eluent to obtain 6.50 g of a near-white solid, with a yield of 82%. . 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0042]

Embodiment 2

[0044] Under nitrogen protection, add 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dihexylfluorene into a 300ml two-necked bottle (4.60g, 10mmol), 2-bromo-7-iodo-9,9-dihexylfluorene (5.39g, 10mmol), potassium carbonate (3.45g, 25mmol), tetrakis(triphenylphosphine) palladium (0.58g, 0.5mmol), 12ml deionized water and 120ml toluene, heated to 80°C for 12 hours. After the reaction was completed, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and after removing the organic phase solvent, the crude product was purified by column chromatography using petroleum ether as eluent to obtain 5.22 g of a near-white solid, with a yield of 70%. . 1 H NMR, 13 CNMR, MS and elemental analysis results show that the obtained compound is the target product, and its chemical reaction equation is as follows:

[0045]

Embodiment 3

[0047] Preparation of Compound 4

[0048] (1) Preparation of Compound 3

[0049] Under nitrogen protection, 2,7-dibromo-9,9-dihexylfluorene (4.92 g, 10 mmol) and 120 ml of anhydrous tetrahydrofuran were added to a 300 ml two-necked flask, and the temperature was lowered to -78°C. Slowly add n-butyllithium n-hexane solution (5.5ml, 11mmol) dropwise, continue to stir at -78°C for half an hour, then add trimethylsilyl chloride (1.63g, 15mmol), and slowly rise to room temperature for 8 hours . Quench the reaction with a small amount of water, extract the product with dichloromethane, wash with saturated sodium chloride solution three times, remove the solvent of the organic phase under reduced pressure, and purify the crude product with a silica gel column (eluent is petroleum ether) to obtain a yellow oily liquid 4.27g, 88% yield. 1 HNMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0050] (2) Preparation of Comp...

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Abstract

The invention discloses a star-shaped blue fluorescent molecule, its synthesis method and application. In the present invention, a star-shaped molecule is obtained through Suzuki coupling of multi-site halogenated symmetric cores and arms containing S,S-dioxo-dibenzothiophene units. By adjusting the structure of the core and arms, the optical bandgap and emission spectrum of star-shaped molecules can be tuned to achieve emission in the deep blue to blue range. Such star-shaped blue fluorescent molecules containing S,S-dioxo-dibenzothiophene units can be used as organic light-emitting materials, and organic light-emitting diodes can be prepared through a solution processing method.

Description

technical field [0001] The invention belongs to the field of organic optoelectronics, and in particular relates to a star-shaped blue fluorescent molecule and its synthesis method and application. Background technique [0002] The most relevant prior art background art, and illustrating the prior art defect organic light-emitting diodes (OLEDs) have received extensive attention due to their active light emission, high efficiency, low-voltage drive, and easy fabrication of large-area devices. The OLED device structure includes a cathode, an anode, and an organic layer in the middle. The organic layer generally includes an electron / hole transport layer and a light-emitting layer. Under the action of an electric field, electrons and holes are injected from the cathode and anode respectively, and migrate in the functional layer respectively, and then form excitons in the light-emitting layer, and the excitons migrate within a certain range, and finally the excitons emit light. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/76C07D409/14C07D487/14C07D471/16C07F7/08C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D333/76C07D409/14C07D471/16C07D487/14C07F7/0812C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1092C09K2211/1096C09K2211/1059H10K85/615H10K85/622H10K85/624H10K85/626H10K85/6576H10K85/40H10K85/6572H10K50/11
Inventor 应磊彭沣黄飞曹镛
Owner 东莞伏安光电科技有限公司
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