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Thermal activation delayed fluorescence material and application thereof

A technology of thermal activation delay and fluorescent material, applied in the direction of luminescent materials, materials of organic semiconductor devices, organic chemistry, etc., can solve the problems of limited application space of phosphorescent materials and high prices of phosphorescent materials, and achieve excellent device efficiency and high performance. Effect

Active Publication Date: 2018-05-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The efficiency of phosphorescent devices is higher than that of fluorescent devices. However, phosphorescent devices also have their disadvantages. For example, phosphorescent materials are mainly complexes containing noble metals, especially metal iridium and platinum complexes. Since metal iridium and platinum are expensive, so , the price of phosphorescent materials is extremely expensive, which also limits the application space of phosphorescent materials

Method used

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  • Thermal activation delayed fluorescence material and application thereof
  • Thermal activation delayed fluorescence material and application thereof
  • Thermal activation delayed fluorescence material and application thereof

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Experimental program
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Embodiment approach

[0041]This embodiment is mainly aimed at the preparation method of the thermally activated delayed fluorescent material, and in combination with this method, some examples are listed, wherein, the steps of the method are as follows: (1) Add the raw materials and compound 1 to the organic solvent, in an inert gas Under the protection of 70-140 ℃ heat preservation reaction for 16-20 hours, cooling down, the reaction solution quickly passed through the basic alumina column, rinsed with o-xylene, after the solvent was removed, it was purified by silica gel column layer, and further used without Hydro-ethanol recrystallization to obtain compound 2;

[0042] (2) Add the compound 2, basic substance and raw materials obtained in step (1) into the solvent, and under the protection of an inert gas, add a catalyst to the system, keep the reaction at 0-200°C for 2-24h, and cool down , rinsed with deionized water, purified the obtained solid crude product through silica gel column chromato...

Embodiment 1

[0048] The preparation of embodiment 1 compound C01

[0049]

[0050] Preparation of compound 2:

[0051] In a 1L three-necked flask, add compound 1 (31.4g, 0.10mol), o-xylene (450g), 2,3-dichloro-5,6-dicyano-p-benzoquinone (50g, 0.22mol), nitrogen protection , heat up to 140°C, keep the temperature for 16 hours, cool down to 25°C, the reaction solution quickly passes through a 280g basic alumina column, rinses with o-xylene, and removes the solvent. The obtained crude product is purified by silica gel column chromatography, and the eluent is Cyclohexane, further recrystallized using absolute ethanol, obtained 21.2g of compound 2 fine product, yield 68.4%, high resolution mass spectrometry, positive ion mode, molecular formula C 10 h 2 Br 2 N 2 , the theoretical value is 309.8564, and the test value is 309.8567.

[0052] Preparation of compound C01: In a 250mL three-necked flask, add compound 2 (1.86g, 6mmol), diphenylamine (2.54g, 15mmol), potassium carbonate (3.3g, 2...

Embodiment 2

[0053] The preparation of embodiment 2 compound C02

[0054]

[0055] Using 4-tert-butyl-N-phenylaniline as raw material, according to the method described in Example 1, compound C02 was prepared to obtain 1.7 g of the target object, high-resolution mass spectrometry, positive ion mode, molecular formula C 42 h 38 N 4 , theoretical value 598.3096, test value 598.3091, elemental analysis (C 42 h 38 N 4 ), theoretical value C: 84.25, H: 6.40, N: 9.36, measured value C: 84.22, H: 6.42, N: 9.36.

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Abstract

The invention relates to a thermal activation delayed fluorescence material and an application thereof. The material has a molecular structure shown in formula (I), the structure has very small triplet state-singlet state energy level difference, proper molecular energy level and good film stability, can realize thermal activation delayed fluorescence luminescence, can be used as a luminous layerof an OLED (organic light-emitting device) and is applied in the OLED field.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and relates to a small molecule organic electroluminescence material capable of realizing heat-activated delayed fluorescent light emission, and relates to the application of the material in the field of organic electroluminescence. Background technique [0002] Organic electroluminescent diode (OLED) was produced in the 1980s. It has many advantages such as self-illumination, wide viewing angle, fast response speed, wide color gamut, and flexible display. After 30 years of continuous development, the OLED The technology has gradually matured. At present, organic electroluminescent technology has been widely used in many products such as smart phones, flat-panel TVs, and virtual reality. [0003] Organic electroluminescent devices are current-driven light-emitting devices. According to different light-emitting mechanisms, they can be divided into two types: fluorescent devices and phosp...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C255/47C07D209/86C07D219/02C07D265/38C07D241/46H01L51/50H01L51/54
CPCC09K11/06C07C255/47C07D209/86C07D219/02C07D241/46C07D265/38C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1044H10K85/649H10K85/633H10K85/657H10K85/6572H10K50/11H10K2102/00H10K2102/301
Inventor 马行康盛磊郭威高树坤胡葆华李韶涛
Owner VALIANT CO LTD
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