Thermal activation delayed fluorescence material capable of being processed by solution, preparation method and application thereof

A technology of thermally activated delayed and fluorescent materials, applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc. Properties, preparation and purification methods are simple, and the effect of improving properties

Pending Publication Date: 2020-10-16
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polymer thermally activated delayed fluorescent materials have a long synthesis route, many side reactions, difficult purification, and the luminous brightness and efficiency are much lower than those of smaller molecules, so the current research progress is slow.

Method used

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  • Thermal activation delayed fluorescence material capable of being processed by solution, preparation method and application thereof
  • Thermal activation delayed fluorescence material capable of being processed by solution, preparation method and application thereof
  • Thermal activation delayed fluorescence material capable of being processed by solution, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound C1

[0033] Step 1, Synthesis of 3,6-bis(4-(9H-carbazol-9-yl)phenoxy)-9H-carbazole in peripheral dendrons

[0034] Add 3,6-dihydroxy-9-hydrogen-carbazole (10g, 25.12mmol), cesium carbonate (4.5g, 13.84mmol), 9-(4-iodophenyl)-9H-carbazole into a 500mL reaction flask (15g, 54.94mmol), N,N-dimethylformamide (200mL), under the protection of nitrogen, react at 100°C for 4h. After the reaction was finished, cool to room temperature, add a large amount of water to stir, and filter with suction to obtain the crude product. Then, it was purified by column chromatography to obtain 3,6-bis(4-(9H-carbazol-9-yl)phenoxy)-9H-carbazole as a white solid with a yield of 70%.

[0035] Step 2, Synthesis of C1

[0036] In dry tetrahydrofuran (THF, 20 mL) was added 3,6-bis(4-(9H-carbazol-9-yl)phenoxy)-9H-carbazole (3.26 g, 3.15 mmol), sodium hydride (0.5 g, 20.3mmol), stirred at room temperature for 0.5h, then added 2,3,4,5,6-pentafluorobenzonitril...

Embodiment 2

[0041] Embodiment 2: Synthesis of C2

[0042] The 3,6-dihydroxy-9-hydrogen-carbazole that reacts with 9-(4-iodophenyl)-9H-carbazole in Example 1 is replaced with 3-hydroxyl carbazole, and through the same process as in Example 1 Synthetic method, the product C2 was obtained. Yield 70%.

[0043] Mass Spectrum: 2214.76.

[0044] Elemental analysis results: C: 85.11, H: 4.32, N: 6.95, O: 3.61.

Embodiment 3

[0045] Embodiment 3: Synthesis of C3

[0046]In the above example 1, the 9-(4-iodophenyl)-9H-carbazole reacted with 3,6-dihydroxy-9-hydrogen-carbazole was replaced by 4-iodo-N, N-diphenylaniline , through the same synthesis method as in Example 1, the product C3 was obtained. Yield 71%.

[0047] Mass spectrum: 3520.33.

[0048] Elemental analysis results: C: 84.23, H: 4.87, N: 6.36, O: 4.56.

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PUM

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Abstract

The invention discloses a thermal activation delayed fluorescence material capable of being processed by a solution, a preparation method and application thereof. The thermal activation delayed fluorescence material capable of being processed by a solution comprises a molecular structure, the molecular structure is composed of two parts, one part is a core with a thermal activation delayed fluorescence property, the other part is a structure with a high triplet state energy level, at most one of R1 and R2 is hydrogen, the other parts are all connected with oxygen through benzene rings, and oxygen connection has a structure with a high triplet state energy level. The novel material has great advantages, the concentration quenching of triplet excitons can be effectively reduced through the steric hindrance effect of peripheral branched chains, and the performance of a light-emitting device is improved; the introduction of benzene rings can effectively enhance the solubility and film-forming property of the material. The thermal activation delayed fluorescence material capable of being processed by the solution has a relatively large molecular weight and good film-forming property, and is suitable for preparing an organic light-emitting device by a wet method. And along with the increase of the peripheral branched chains, the performance of the device is greatly improved.

Description

technical field [0001] The invention relates to an organic luminescent material and its preparation method and application, in particular to a solution-processable heat-activated delayed fluorescent material. Background technique [0002] Organic light-emitting diodes (OLEDs) are known as the most promising next-generation displays due to their low driving voltage, fast response, high luminous efficiency, simple manufacturing process, and easy realization of full-color display. The thermally activated delayed fluorescence material (TADF) achieves 100% internal quantum efficiency because it can make full use of single triplet excitons. Therefore, TADF materials are widely used in organic light emitting diodes. So far, researchers of TADF materials have mainly focused on how to improve the performance of OLED devices and their color purity. [0003] In small molecule TADF materials, researchers have made great achievements in these two aspects. However, there are still some...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D209/88C09K11/06H01L51/54H01L51/50
CPCC07D209/86C07D209/88C09K11/06C09K2211/1011C09K2211/1029C09K2211/1014H10K85/624H10K85/626H10K85/631H10K85/6572H10K50/11
Inventor 蒋伟夏明辉
Owner SOUTHEAST UNIV
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