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Compound, thermal activation delayed fluorescence material, organic electroluminescent device and application thereof

A compound and electromechanical technology, applied in the direction of luminescent materials, electrical solid devices, silicon organic compounds, etc., can solve the problems of improvement, instability of phosphorus-oxygen groups, inability to have both device efficiency and lifespan, etc.

Pending Publication Date: 2020-10-27
BEIJING ETERNAL MATERIAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are the following defects in the application of these two types of hosts: their electron transport ability is weak, which leads to uneven distribution of excitons and serious device efficiency roll-off; and phosphorus-oxygen material compounds have high efficiency, but due to the Group instability, resulting in unsatisfactory device life
[0005] It can be seen that a variety of TADF materials have been reported, but these compounds still cannot improve device efficiency and lifetime, so the development of blue OLED materials is still very important

Method used

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  • Compound, thermal activation delayed fluorescence material, organic electroluminescent device and application thereof
  • Compound, thermal activation delayed fluorescence material, organic electroluminescent device and application thereof
  • Compound, thermal activation delayed fluorescence material, organic electroluminescent device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0065] Synthesis Example 1: Synthesis of Product P1

[0066]

[0067] Synthesis of Intermediate M1

[0068] Under nitrogen atmosphere, 3-bromo-4-fluorobenzonitrile 4.0g (19.8mmol, 1.1eq), 3,9-bicarbazole 6.0g (18mmol, 1.0eq), cesium carbonate 12.0g (36mmol, 2.0 eq), after adding 60 mL of DMF, the temperature was raised to 150° C., and the reaction was carried out overnight. Using silica gel column chromatography. Obtained M1, mass spectrum: 512.

[0069] Synthesis of Product P1

[0070] Under nitrogen atmosphere, M15.2g (10.0mmol, 1.0eq), 2,4-diphenyl-6-pinacol ester-1,3,5-triazine 4.4g (12.0mmol, 1.2eq), Pd(PPh 3 ) 4 0.23g (0.2mmol, 2%eq), potassium carbonate 4.2g (30.0mmol, 3eq) was added to the 100mL single-necked bottle, dioxane / water (50mL / 5mL) was added to the 100mL single-necked bottle, and the temperature was raised to reflux temperature, and the reaction overnight. Cool down to room temperature and filter the solid. After the solid is rinsed with a mixt...

Synthetic example 2

[0071] Synthesis Example 2: Synthesis of Product P9

[0072]

[0073] Synthesis of intermediate M2

[0074] The reactant 3-bromo-4-fluorobenzonitrile is replaced by 6-formonitrile-3',6'-dimethyl-9H-3,9-bicarbazole, and the process is the same as that of intermediate M1 in Synthesis Example 1 Synthetic method to get M2, mass spectrum: 565.

[0075] Synthesis of Product P9

[0076] The reactant M1 was replaced by the intermediate M2, and P9 was obtained through the same synthesis method as that of P1 in Synthesis Example 1, mass spectrum: 717. 1 H NMR (300MHz, CDCl 3 ): 8.72(1H), 8.30(4H), 8.15(1H), 7.99(1H), 7.86(1H), 7.81(2H), 7.62(2H), 7.51(5H), 7.40(3H), 7.32(2H ), 6.88(1H), 2.34(6H).

Synthetic example 3

[0077] Synthesis Example 3: Synthesis of Product P13

[0078]

[0079] Synthesis of Intermediate M3

[0080] Replacing reactant M1 with 2,4-diphenyl-6-pinacol ester-1,3,5-triazine 4-cyanophenylboronic acid with 6-bromo-3',6'-dimethyl -9H-3,9-bicarbazole, through the same synthesis method as product P1 in Synthesis Example 1, M3 was obtained, mass spectrum: 461.

[0081] Synthesis of Intermediate M4

[0082] The reactant 3,9-bicarbazole was replaced by intermediate M4, and M4 was obtained through the same synthesis method as intermediate M1 in Synthesis Example 1, mass spectrum: 641.

[0083] Synthesis of Product P13

[0084] The reactant M1 was replaced by the intermediate M4 for reaction, and P13 was obtained through the same synthesis method as the product P1 in Synthesis Example 1, mass spectrum: 793. 1 H NMR (300MHz, CDCl 3 ): 8.72(1H), 8.30(4H), 8.18(1H), 7.99(3H), 7.92(1H), 7.86(1H), 7.84(2H), 7.82(3H), 7.78(1H), 7.63(1H ), 7.61(1H), 7.51(5H), 7.40(3H), 7....

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Abstract

The invention discloses a compound, a thermal activation delayed fluorescence material, an organic light-emitting device and application thereof, wherein the compound has a general formula structure represented by a formula (I) defined in the specification. According to a molecular skeleton of the compound, electron donating and electron withdrawing groups are introduced, the energy level of the compound can be effectively regulated and controlled through bridging bonds, and energy level data matched with adjacent materials is realized, so that good device performance is obtained; and the current efficiency and the external quantum efficiency of the prepared organic light-emitting device are greatly improved, and the service life of the device is obviously prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent display, and in particular relates to an organic electroluminescent material compound, especially a compound, a thermally activated delayed fluorescent material and its application in organic electroluminescent devices, and an organic electroluminescent material using the same. Electromechanical Luminescent Devices. Background technique [0002] The earliest dyes used in OLEDs are pure organic small molecule light-emitting materials. Devices based on such materials have long life and low efficiency roll-off. However, the material can only use 25% of S1 to emit light, and 75% of T1 can only be lost through non-radiative transitions due to spin prohibition. In 1998, Forrest et al. from Princeton University reported for the first time PHOLEDs based on T1 emission. Utilizing the spin-orbit coupling effect caused by the heavy metal Pt atoms, T1 can emit light effectively at room t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D487/16C07D495/04C07D209/86C07F7/08C09K11/06H01L51/50H01L51/54H01L27/32
CPCC07D403/14C07D401/14C07D487/16C07D495/04C07D209/86C07F7/0814C09K11/06C09K2211/1007C09K2211/1011C09K2211/1022C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1092H10K59/00H10K85/636H10K85/654H10K85/6572H10K85/657H10K85/40H10K50/11
Inventor 高文正张春雨魏金贝李国孟徐超
Owner BEIJING ETERNAL MATERIAL TECH
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