Quinoxaline unit containing organic thermally activated delayed fluorescent material and application thereof

A thermally induced delayed fluorescence, quinoxaline technology, applied in luminescent materials, organic chemistry, electrical components, etc., can solve the problems of expensive heavy metal materials, need to improve the stability, affecting practical use, etc., to achieve low attenuation, high-efficiency electroplating Luminous performance, high stability effect

Active Publication Date: 2016-10-26
深圳智材有机光电有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first-generation organic electroluminescent materials are ordinary fluorescent materials, because they can only use 25% of the energy from singlet excitons, so the external quantum efficiency of the device can never break through the bottleneck of 5%, which affects its practical use.
The second generation is organic phosphorescent materials, because of the use of phosphorescent complexes, its electroluminescence can use 100% of the energy of excitons, which has greater advantages, but because rare heavy metal materials are expensive and limited, and blue phosphorescent materials are stable performance needs to be improved, so another path needs to be found to improve the above problems
[0004] But in general, such materials and OLED devices based on TADF effect, especially red-orange light materials and devices, still have many deficiencies and need to be further improved.

Method used

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  • Quinoxaline unit containing organic thermally activated delayed fluorescent material and application thereof
  • Quinoxaline unit containing organic thermally activated delayed fluorescent material and application thereof
  • Quinoxaline unit containing organic thermally activated delayed fluorescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: the synthesis of important intermediate

[0060] The structures of intermediates ①~⑩ are as follows:

[0061]

[0062] (1) Synthesis of intermediate ①:

[0063]

[0064] 4-Fluoro-1,2-phenylenediamine (0.68g, 5.40mmol) and 4,4′-dibromobenzil (2.00g, 5.43mmol) were dissolved in toluene-acetic acid consisting of 20mL toluene and 30mL acetic acid solution, stirred evenly and refluxed for 8 hours, after the reaction was completed, cooled to room temperature, then poured the reaction solution into water, first extracted with dichloromethane, then dichloromethane / petroleum ether (v / v=2:3) Silica gel column chromatography separation was carried out as eluent, and drying was performed after rotary evaporation to obtain intermediate ① (2.10 g, yield rate 84%), which was a white powder.

[0065] (2) Synthesis of intermediate ②:

[0066] Select 4,5-difluoro-1,2-phenylenediamine and 4,4'-dibromobenzil as raw materials, refer to the synthesis steps and solvents...

Embodiment 2

[0084] Embodiment 2: Preparation of compound Ⅰ-1-1

[0085]

[0086] Intermediate ① (1.2g, 2.62mmol), phenothiazine (1.25g, 6.28mmol), sodium tert-butoxide (0.63g, 6.56mmol), palladium acetate (0.025g, 0.11mmol), tri-tert-butylphosphine Add tetrafluoroborate (0.095g, 0.33mmol) and 45mL of toluene into a 100mL round bottom flask together, reflux at 110°C for 48 hours, then quench the reaction with 10mL saturated aqueous sodium chloride solution, extract with dichloromethane first, then Dry over anhydrous sodium sulfate, and finally use dichloromethane / petroleum ether (v / v=2:3) as the eluent for silica gel column chromatography. The product is a yellow powder with a yield of 98%. Elemental Analysis Theoretical Value C 44 h 27 FN 4 S 2 (%): C 76.06, H 3.92, N 8.06; found values: C 76.15, H 4.01, N 8.11.

Embodiment 3

[0087] Embodiment 3: the preparation of compound Ⅰ-2-2

[0088]

[0089] Intermediate ② (1.2g, 2.52mmol), phenoxazine (1.06g, 5.79mmol), sodium tert-butoxide (0.58g, 6.04mmol), palladium acetate (0.023g, 0.10mmol), tri-tert-butylphosphine Add tetrafluoroborate (0.088g, 0.30mmol) and 40mL toluene into a 100mL round-bottomed flask, reflux at 110°C for 48 hours, then quench the reaction with 10mL saturated aqueous sodium chloride solution, extract with dichloromethane, then Dry over anhydrous sodium sulfate, and finally use dichloromethane / petroleum ether (v / v=2:3) as the eluent for silica gel column chromatography. The product is a yellow powder with a yield of 95%. Elemental Analysis Theoretical Value C 44 h 26 f 2 N 4 S 2 (%): C 76.64, H 3.85, N 8.23; found values: C 76.59, H 3.84, N 8.24.

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Abstract

The invention relates to a quinoxaline unit containing organic thermally activated delayed fluorescent material and an application thereof. The organic thermally activated delayed fluorescent material, which contains a quinoxaline unit and has good light emitting performance, is obtained through carrying out multiaspect modification by taking quinoxaline with high electrophilicity as a core and constructing different D-A structures by particularly introducing fluorine atoms with high electro-withdrawing power to molecular design for the first time, so that efficient light-emitting elements are obtained, and the thinking of people that conventional fluorescent materials are free of halogens is broken through. The organic thermally activated delayed fluorescent material is simple in synthesis and high in yield and has the advantages of practical large-scale production and application. The [delta]E(S1-T1) of the organic thermally activated delayed fluorescent material is not greater than 0.65eV, so that the organic thermally activated delayed fluorescent material can be applied to the evaporation-coating of devices and can also be applied to the spin-coating of the devices. Electroluminescent elements and luminescent devices with high efficiency, high brightness, low-efficiency attenuation and low trigger voltage are provided through using the novel thermally activated delayed fluorescent material, so that the organic thermally activated delayed fluorescent material can be extensively applied to the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the field of organic luminescent materials, and relates to an organic heat-induced delayed fluorescent material containing quinoxaline units and its application in organic electroluminescent devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of self-illumination, wide viewing angle, fast response, and flexible display, etc., and have great application prospects in the field of display and lighting, and have attracted more and more attention. . [0003] Organic electroluminescence can be divided into fluorescence and phosphorescence electroluminescence. The first-generation organic electroluminescent materials are ordinary fluorescent materials, because they can only use 25% of the energy from singlet excitons, so the external quantum efficiency of their devices cannot break through the bottleneck of 5%, which affects their practical use. The second generation is organic phosphores...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D417/14C07D413/14C07D401/04C07D401/14C07D403/14H01L51/50H01L51/54
CPCC09K11/06C07D401/04C07D401/14C07D403/14C07D413/14C07D417/14C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1029H10K85/657H10K85/6572H10K50/00H10K50/11
Inventor 杨楚罗余玲
Owner 深圳智材有机光电有限公司
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