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Ketone-containing organic compound and application thereof

An organic compound and organic technology, applied in the field of organic electroluminescence devices, can solve the problems of high fluorescence quantum yield, short delayed luminescence life, poor device effect, etc., and achieve good spectral stability, improved life, The effect of improving efficiency

Pending Publication Date: 2022-05-17
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Theoretically, TADF materials can achieve 100% exciton utilization through the anti-intersystem jumping from triplet state to singlet state, but in the process of acting as a host or doping in practical applications, the device effect is not good, and its main The following problems: (1) Due to the small S1-T1 bandgap required by the design of TADF materials, it is difficult to achieve both fast anti-system crossing rate (shorter delayed luminescence lifetime) and high fluorescence quantum yield; (2) due to Strong CT effect, TADF material has spectral instability caused by different ratios

Method used

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  • Ketone-containing organic compound and application thereof
  • Ketone-containing organic compound and application thereof
  • Ketone-containing organic compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0054] Preparation of raw material C

[0055] The preparation process of raw material C1:

[0056]

[0057] Under a nitrogen atmosphere, add 0.05mol of raw material M1 and 0.06mol of Mg powder into the three-necked flask, then add 60ml of dry tetrahydrofuran to dissolve them, and then add 0.0004mol of elemental I 2 . The reaction mixture was heated to 40 °C and stirred until the solution changed from yellow to colorless. Then the mixed solution was heated to 80° C., stirred and reacted for 4 hours, no magnesium powder was left, and the reaction was complete to obtain the raw material C1.

[0058]The preparation method of other raw material C is similar to the preparation method of raw material C1, only the raw material M1 is changed.

[0059] Preparation of Intermediate B

[0060] The preparation process of intermediate B1:

[0061]

[0062] In a three-neck flask, dissolve 8 mmol of raw material D1 in 50 ml of anhydrous tetrahydrofuran, cool in an ice bath and stir ...

Embodiment 1

[0069] The synthesis of embodiment 1 compound 6

[0070]

[0071] 4.4 mmol of intermediate B1 and 4.4 mmol of starting material E1 were added to 50 ml of toluene solution, degassed for 10 min, and then 0.1 mmol of Pd(AcO) was added 2 , 0.3mmol 1,1'-bis(diphenylphosphino)ferrocene (dppf) and 6mmol tBuONa, under the protection of nitrogen, the mixture was stirred and heated at reflux for 24 hours, then the reaction solution was poured into water, and firstly washed with dichloromethane Extraction, organic compounds were dried with magnesium sulfate, and then dichloromethane / petroleum ether (v / v=2:3) was used as eluent for silica gel column chromatography separation, rotary evaporation and drying, and the final product was re-treated at 280 °C and 4 ×10 -4 Further sublimation at Pa afforded compound 6.

[0072] The preparation methods of Example 2-Example 18 are similar to Example 1, except that the raw materials and intermediates used are different. The following table list...

Embodiment 19

[0078] Embodiment 19: the synthesis of compound 27

[0079]

[0080] (1) Add 4.4mmol of intermediate B16 and 4.4mmol of raw material E2 to 50ml of toluene solution, degas for 10 minutes, and then add 0.1mmol of Pd(AcO) 2 , 0.3mmol 1,1'-bis(diphenylphosphino)ferrocene (dppf) and 6mmol tBuONa, under the protection of nitrogen, the mixture was stirred and heated at reflux for 24 hours, then the reaction solution was poured into water, and firstly washed with dichloromethane Extraction, organic compounds were dried with magnesium sulfate, and then dichloromethane / petroleum ether (v / v=2:3) was used as eluent for silica gel column chromatography separation, rotary evaporation and drying, and the final product was re-treated at 280 °C and 4 ×10 -4 Further sublimation under Pa affords intermediate Ⅰ-1.

[0081] (2) Add 4.4mmol of intermediate I-1 and 4.4mmol of raw material E6 to 50ml of toluene solution, degas for 10 minutes, and then add 0.1mmol of Pd(AcO) 2 , 0.3mmol 1,1'-bis...

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Abstract

The invention discloses a ketone-containing organic compound and application thereof, and belongs to the technical field of semiconductors. The structure of the organic compound provided by the invention is shown as a general formula (I). The invention also discloses application of the compound. The organic compound disclosed by the invention has relatively high thermal stability; meanwhile, when the material is used as a luminescent layer material of an OLED luminescent device, a TADF effect can be generated, the voltage of the device can be effectively reduced, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

technical field [0001] The invention relates to a ketone-containing organic compound and an organic electroluminescent device comprising a light-emitting layer of the ketone-containing compound, belonging to the technical field of semiconductors. Background technique [0002] Organic electroluminescent device (OLED: Organic Light Emission Diodes) technology can be used to manufacture new display products and also can be used to make new lighting products. It is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic light-emitting functional layers sandwiched between different electrode film layers. Various materials with different functions are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D487/04C07D491/048C07D495/04C07D471/04C07D409/14C09K11/06H01L51/50H01L51/54
CPCC07D405/14C07D487/04C07D491/048C07D495/04C07D471/04C07D409/14C09K11/06C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1088C09K2211/1092C09K2211/1059H10K85/626H10K85/657H10K85/6572H10K85/6574H10K85/6576H10K50/11
Inventor 侯美慧曹旭东张兆超李崇
Owner JIANGSU SUNERA TECH CO LTD
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