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Thermally-activated delayed fluorescence materials and application thereof

A technology of thermally activated delayed and fluorescent materials, applied in the fields of luminescent materials, materials of organic semiconductor devices, organic chemistry, etc. problems such as bulk structural units, to achieve the effects of excellent thermal stability, excellent film stability, and excellent device efficiency

Inactive 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

[0010] In 2002, the phenomenon of thermally activated delayed fluorescence has not yet been discovered. The materials involved in the patent JP2002265938 are designed according to the structure of conventional fluorescent materials. Although DB1 has shown good hole transport ability and excellent film stability, due to the structure of DB1 Among them, there is a lack of electron acceptor structural units. Therefore, DB1 does not have the performance of thermally activated delayed fluorescence materials, and cannot effectively use triplet excitons to emit light. Therefore, the organic electroluminescent device prepared using DB1 as a functional layer has a lower device efficiency. Low

Method used

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  • Thermally-activated delayed fluorescence materials and application thereof
  • Thermally-activated delayed fluorescence materials and application thereof
  • Thermally-activated delayed fluorescence materials and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1, preparation of compound C01.

[0032]

[0033] Compound 1 was prepared by referring to the method described in Tetrahedron Letters, 2002, 43(32), 5521-5524.

[0034] Preparation of compound C01: In a 100mL three-necked flask, add compound 1 (2.08g, 6.0mmol), p-iodobenzonitrile (3.2g, 14mmol), potassium carbonate (2.07g, 15mmol), copper powder (0.65g), ortho 50g xylene, heat up to 140°C, keep the temperature for 15h, cool down to 25°C, pour the reaction solution into 150mL deionized water, add 150g tetrahydrofuran, filter with suction, collect the filtrate, separate the liquid, wash the organic phase with 150g deionized water, organic The solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography. The eluent was n-hexane:dichloromethane=1:2 (V / V). The obtained crude product of target C01 was further sublimated and purified using a chemical vapor deposition system. The sublimation temperature ...

Embodiment 2

[0035] Example 2, the preparation of compound C02.

[0036]

[0037] Using m-iodobenzonitrile as raw material, according to the method described in Example 1, compound C02 was prepared to obtain 1.3 g of the target object, high-resolution mass spectrometry, positive ion mode, molecular formula C 39 h 24 N 4 , theoretical value 548.2001, test value 548.2006, elemental analysis (C 39 h 24 N 4), theoretical value C: 85.38, H: 4.41, N: 10.21, measured value C: 85.40, H: 4.39, N: 10.21.

Embodiment 3

[0038] Example 3, preparation of compound C03.

[0039]

[0040] Using m-iodobenzonitrile as raw material, according to the method described in Example 1, compound C03 was prepared to obtain 1.5 g of the target object, high-resolution mass spectrometry, positive ion mode, molecular formula C 39 h 24 N 4 , theoretical value 548.2001, test value 548.2005, elemental analysis (C 39 h 24 N 4 ), theoretical value C: 85.38, H: 4.41, N: 10.21, measured value C: 85.40, H: 4.38, N: 10.22.

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Abstract

The invention relates to thermally-activated delayed fluorescence materials and application thereof. The materials have a molecular structure as shown in a formula (I). The thermally-activated delayedfluorescence materials have very small triplet-singlet energy level difference, proper molecular energy levels and good film stability, can realize thermally-activated delayed fluorescence radiationand are applicable as light-emitting layers of organic electroluminescent devices to the field of organic electroluminescence.

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): C09K11/06C07D471/10H01L51/50H01L51/54
CPCC09K11/06C07D471/10C09K2211/1007C09K2211/1029H10K85/6572H10K50/11H10K2102/00H10K2102/301
Inventor 盛磊高树坤王正刘晓玲胡葆华王元贵
Owner VALIANT CO LTD
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