Preparation and application of thermally active delayed fluorescent material on basis of isoindigo unit

A delayed fluorescence, thermally active technology, applied in the manufacturing of luminescent materials, electrical components, semiconductor/solid-state devices, etc., can solve the problems of low efficiency of OLEDs, and achieve the effect of enhancing electron absorption ability, small energy level difference, and good stability

Inactive Publication Date: 2019-08-27
安徽秀朗新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to the spin statistical theory, the ratio of excited singlet state and excited triplet state is 3:1, that is, in electroluminescence, the fluorescent material only uses singlet state excitons to emit light, and its theoretical internal quantum efficiency is 25%. This is the root cause of the low efficiency of OLEDs

Method used

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  • Preparation and application of thermally active delayed fluorescent material on basis of isoindigo unit
  • Preparation and application of thermally active delayed fluorescent material on basis of isoindigo unit
  • Preparation and application of thermally active delayed fluorescent material on basis of isoindigo unit

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Experimental program
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Effect test

Embodiment 1

[0018]

[0019] Add 6,6'-dibromoisoindigo (1.0g, 2.4mmol), methyl iodide (0.7g, 5mmol), NaH (0.07mg, 3mmol) and DMF (20mL) successively in a 100mL single-necked bottle, and the mixture is Heat to 80oC and stir for 24 hours. After the reactant was cooled to room temperature, the mixture was extracted with CH2Cl2 (3×30mL); the organic layer was washed with water (60mL), dried, and evaporated under reduced pressure to remove the solvent; the residue was separated by column chromatography using petroleum ether as the eluent to obtain compound 1 0.8 g (yield: 75%).

Embodiment 2

[0021]

[0022] Add compound 1 (0.6g, 1.3mmol), malononitrile (0.3g, 4.0mmol), Al2O3 (0.1g, 1mmol) and toluene (20mL) successively in a 100mL single-necked bottle, and the mixture is heated to 85oC under nitrogen and stirred for 24 Hour. After the reactant was cooled to room temperature, the mixture was extracted with CH2Cl2 (3×30mL); the organic layer was successively washed with water (60mL), dried, and evaporated under reduced pressure to remove the solvent; the residue was washed with petroleum ether:dichloromethane (V:V=1: 1) The eluent was separated by column chromatography and then recrystallized to obtain 0.35 g of the target product (yield: 62%).

Embodiment 3

[0024]

[0025] Add compound 2 (0.4g, 0.74mmol), diphenylamine (0.4g, 2.2mmol), tetrakistriphenylphosphine palladium (187mg, 0.0162mmol), ethanol (10mL), toluene (30mL) and 2M aqueous potassium carbonate solution (10 mL), the mixture was heated to 90°C under nitrogen and stirred for 24 hours. After the reactant was cooled to room temperature, the mixture was extracted with CH2Cl2 (3×30mL); the organic layer was successively washed with water (60mL), dried, and evaporated under reduced pressure to remove the solvent; the residue was dichloromethane (V:V=1: 2) 300 mg of compound 3 was obtained by column chromatography as the eluent (yield: 60%).

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Abstract

The invention discloses preparation and application of a thermally active delayed fluorescent material on the basis of an isoindigo unit. By introducing four cyano groups into the isoindigo unit, a novel strong absorption electron structural unit is constructed, reduction of overlapping of the highest occupied molecular orbital and lowest unoccupied molecular orbital of molecules is facilitated, correspondingly the energy level difference between the singlet state and triplet state of the molecules is reduced, and thermally active delayed fluorescence is obtained. Furthermore, the material isused as a light-emitting layer dopant, an organic electroluminescent device is prepared through a solution method, and the maximum external quantum efficiency of up to 14.1% is obtained.

Description

technical field [0001] The present invention relates to a novel organic thermally active delayed fluorescence (TADF) material, in particular to a donor-acceptor-donor with isoindigo derivatives as acceptor units and diphenylamine, carbazole and acridine as donor units. A bulk (D-A-D) type organic thermally active delayed fluorescent material and its application as a light-emitting layer material of an organic electroluminescent diode belong to the technical field of organic electroluminescent materials. Background technique [0002] Organic light-emitting diodes (OLEDs) are considered to be the ultimate technology for flat-panel displays because of their high brightness, low power consumption, large-area fabrication, and flexible displays. After more than thirty years of development, the development of OLEDs has achieved great success. Organic electroluminescent materials, as the core components of OLEDs, have also achieved rapid development. At present, organic electrolum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/24C09K11/06H01L51/50H01L51/54
CPCC07D209/24C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029H10K85/636H10K85/631H10K85/6572H10K50/12
Inventor 王亚飞庞玉东
Owner 安徽秀朗新材料科技有限公司
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