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A kind of organic thermally induced delayed fluorescent material containing quinoxaline unit and its application

A thermally induced delayed fluorescence, quinoxaline technology, applied in the direction of 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., and achieve low attenuation, high efficiency electroplating Luminous performance, high stability effect

Active Publication Date: 2018-11-23
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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  • A kind of organic thermally induced delayed fluorescent material containing quinoxaline unit and its application
  • A kind of organic thermally induced delayed fluorescent material containing quinoxaline unit and its application
  • A kind of organic thermally induced delayed fluorescent material containing quinoxaline unit and its application

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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

In the present invention, quinoxaline with high electrophilic performance is used as the core for multi-directional modification, especially in the molecular design, the D-A structure with strong electron-withdrawing ability and different fluorine atom structure is introduced for the first time, and a quinoxaline-containing Units, organic thermally induced delayed fluorescent materials with good luminous properties, thus obtaining high-efficiency light-emitting components, breaking the usual thinking that fluorescent materials do not contain halogens. The invention has the advantages of simple synthesis, high yield and the advantages of actual large-scale production and application. The ΔE(S1-T1) of the organic thermally delayed fluorescent material is less than or equal to 0.65 eV, and can be used for evaporation devices and spin-coating devices. By using the new thermally induced delayed fluorescent material, an electroluminescence element and a light-emitting device with high efficiency, high brightness, low efficiency decay and low start-up voltage are provided, which can be widely used in 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 Patents(China)
IPC IPC(8): C07D417/14C07D413/14C07D401/04C07D401/14C07D403/14C09K11/06H01L51/50H01L51/54
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