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Thermo-activating delayed fluorescent material allowing solution processing and preparation method 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. performance, the effect of reducing concentration quenching, and improving performance

Active Publication Date: 2018-09-28
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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  • Thermo-activating delayed fluorescent material allowing solution processing and preparation method thereof
  • Thermo-activating delayed fluorescent material allowing solution processing and preparation method thereof
  • Thermo-activating delayed fluorescent material allowing solution processing and preparation method thereof

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 thermo-activating delayed fluorescent material allowing solution processing and a preparation method thereof, wherein the molecular structure of the material is composed of two parts: one is a core having property of thermo-activating delayed fluorescence, the other is a group connected via an alkyl chain and having high triplet state energy level. The molecular structureis represented as the formula (I), wherein at most one of R1 and R2 is hydrogen, others being the group connected via an alkyl chain and having high triplet state energy level. The novel material hasthe following advantages: due to the steric-hinerance effect of surrounding branch chains, concentration quenching of a triplet-state exciton is effectively reduced, thus improving performance of a light-emitting device. By introducing the alkyl chain, dissolubility and film-forming performance of the material are effectively enhanced. A result proves that the thermo-activating delayed fluorescent material has large molecular weight and excellent film-forming performance, so that the material is suitable for preparing an organic light-emitting device in a wet process. With increase of the surrounding branch chains, the performance of the device can be improved greatly.

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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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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