A solution-processable thermally activated delayed fluorescent material and its preparation method

A technology of thermally activated delay and fluorescent materials, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc. It can solve the problems of low luminous brightness and efficiency, slow research progress, long synthesis route, etc., and achieve excellent devices performance, reduced concentration quenching, and improved performance

Active Publication Date: 2020-09-18
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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  • A solution-processable thermally activated delayed fluorescent material and its preparation method
  • A solution-processable thermally activated delayed fluorescent material and its preparation method
  • A solution-processable thermally activated delayed fluorescent material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound C1

[0036] Step 1, S1CH 3 Synthesis of O

[0037] Add 3-bromo-9,9-spirobifluorene (10g, 25.12mmol), sodium methoxide (50mL, 25.12mmol), CuI (15g, 78.94mmol), N,N-dimethylformamide into a 500mL reaction flask (200mL), under nitrogen protection, react at 120°C for 24h. After the reaction, cool to room temperature, add a large amount of water to stir, and filter with suction to obtain a crude product. Then, purified by column chromatography to obtain S1CH 3 O is a white solid, and the yield of S1CH3O is 70%.

[0038] Step 2, Synthesis of S1OH

[0039] Add S1CH to the reaction vial 3 O (6g, 17.19mmol) was dissolved by adding 30mL of dichloromethane solution. Under ice-bath conditions, a solution of 3-boron bromide (15mL) in dichloromethane solution (30mL) was added dropwise with a separatory funnel. The reaction was stirred at 0° C. for 4 h, quenched with methanol (20 mL), and washed with sodium bicarbonate to adjust the pH of...

Embodiment 2

[0050] Embodiment 2: Synthesis of C2

[0051]In the above example, the 3,6-dihydroxy-9-hydrogen-carbazole reacted with S1O-Br was replaced with 3-hydroxycarbazole, and the product C2 was obtained through the same synthesis method as in Example 1. Yield 70%.

[0052] Mass spectrum: 2484.05.

[0053] Elemental analysis, the results are as follows: C: 86.47, H: 5.56, N: 2.82, O: 5.15.

Embodiment 3

[0054] Embodiment 3: Synthesis of C3

[0055] Step 1, Synthesis of Branched CZ-Br

[0056] Add di-tert-butylcarbazole (6.7g, 23.92mmol), 1,6-dibromohexane (33mL, 143.5mmol), KOH (15g, 267.85mmol / dissolve in 10mL water first) in toluene solution (80mL) , tetrabutylammonium bromide (1 g, 1.8 mmol). Under the protection of nitrogen, the reaction was stirred at 80° C. for 3 h, and directly spin-dried after the reaction. Purified by column chromatography to obtain the CZ-Br product with a yield of 71%.

[0057] Step 2, Synthesis of CZ-CZO

[0058] Under nitrogen protection, add CZ-Br (7.23g, 16.26mmol), 3,6-dihydroxy-9-hydro-carbazole (1.61g, 8.13mmol), cesium carbonate (6.7g, 21.12 mmol), DMF (30 mL). The reaction conditions and post-reaction treatment are the same as the synthesis of CZ-2S1O in Example 1. The product CZ-CZO was obtained with a yield of 60%.

[0059] Step 3, Synthesis of C3

[0060] Add CZ-CZO (3.90g, 4.08mmol) and sodium hydride (0.6g, 24.3mmol) to dry te...

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Abstract

The invention discloses a heat-activated delayed fluorescent material capable of solution processing and a preparation method thereof. This type of molecular structure is composed of two parts, one part is a core with thermally activated delayed fluorescence properties, and the other part is a group with a high triplet energy level connected by an alkyl chain, and has a structure as shown in formula I, formula I, wherein , R 1 , R 2 At most one of them is hydrogen, and the rest are groups with high triplet energy levels linked by alkyl chains. The advantages of this new material: the steric hindrance effect of the peripheral branch chain can effectively reduce the concentration quenching of the triplet excitons and improve the performance of the light-emitting device; the introduction of the alkyl chain can effectively enhance the solubility and film-forming properties of the material. The results show that this kind of solution-processable heat-activated delayed fluorescent material has relatively large molecular weight and good film-forming performance, and is suitable for wet preparation of organic electroluminescent devices. And with the increase of peripheral branch chains, the performance of the device is greatly improved.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, and in particular relates to a novel organic luminescent material, that is, 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. However, 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/88C07D401/14C09K11/06H01L51/54
CPCC09K11/06C07D209/88C07D401/14C09K2211/1029C09K2211/1007H10K85/624H10K85/626H10K85/6572
Inventor 蒋伟黄素丽孙岳明
Owner SOUTHEAST UNIV
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