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Compound, luminescent material, organic light-emitting display panel, and organic light-emitting display device

A technology for luminescent display and luminescent materials, which is applied in the fields of compounds, luminescent materials, organic light-emitting display panels and organic light-emitting display devices. Effect of improving luminous efficiency

Active Publication Date: 2021-10-15
TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few TADF materials that have been discovered so far, and the performance needs to be improved. New TADF materials that can be used in OLED devices need to be developed urgently.

Method used

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  • Compound, luminescent material, organic light-emitting display panel, and organic light-emitting display device
  • Compound, luminescent material, organic light-emitting display panel, and organic light-emitting display device
  • Compound, luminescent material, organic light-emitting display panel, and organic light-emitting display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0125] Compound P1 was prepared by the following method:

[0126] Specific steps:

[0127]

[0128] Weigh S1 (8.0mmol), S2 (9.7mmol), K2CO3 (33.9mmol), CuI (2.0mmol), 18-crown-6 (0.82mmol), and dissolve in anhydrous dichlorobenzene under nitrogen atmosphere. Stir at 100°C for 12h. After the reaction, cool to room temperature. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and the final purification gave solid S3 (4.8 mmol, 60%).

[0129] Characterization results: MALDI-TOF MS: m / z calcd for C 24 h 14 BrNS: 427.0; found: 427.3.

[0130]

[0131] At -78°C, S3 (2.0 mmol) was dissolved in ether (40 mL), and nBuLi (3.0 mmol) in n-hexane was added dropwise to the solution. The reaction solution was continuously stirred for 2 h, slow...

preparation example 2

[0134] Compound P3 was prepared by the following method:

[0135]

[0136] Specific steps:

[0137] Weigh S1 (6mmol), S5 (7.2mmol), K 2 CO 3 (25.2mmol), CuI (1.5mmol), 18-crown-6 (0.64mmol), dissolved in anhydrous dichlorobenzene under nitrogen atmosphere. Stir at 100°C for 12h. After the reaction, cool to room temperature. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography, and the final purification afforded solid S6 (3.72 mmol, 62%).

[0138] Characterization results: MALDI-TOF MS: m / z calcd for C 27 h 20 BrNS: 469.0; found: 469.4.

[0139]

[0140] At -78°C, S6 (1.5 mmol) was dissolved in ether (40 mL), and nBuLi (2.2 mmol) in n-hexane was added dropwise to the solution. The reaction solution was continuously stirred for 2 h,...

preparation example 3

[0143] Compound P16 was prepared by the following method:

[0144]

[0145] In a 100mL three-necked flask, first S6 (10.0mmol), pinacol diborate (10.5mmol), (1,1,-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.2 mmol) and potassium acetate (25.0 mmol) were added respectively, while stirring, degassing and nitrogen replacement were repeated 3 times rapidly, and 50 mL of tetrahydrofuran was added through a syringe. Stir at a certain speed, and heat the reactants of the obtained mixed solution to reflux at a reaction temperature of 80°C for 5 hours; after the reaction is completed, cool to room temperature and add 60 mL of water, extract with ether, and dry the obtained organic phase with anhydrous sodium sulfate , the solvent was distilled off, and purified by column chromatography to obtain intermediate S7 (7.7 mmol, 77%).

[0146] Characterization results: MALDI-TOF MS: m / z calcd for C 33 h 32 BNO 2 S: 517.2; found: 517.3;

[0147]

[0148] Under nitrogen ...

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Abstract

The present invention relates to a compound, a luminescent material, an organic light-emitting display panel and an organic light-emitting display device. The compound has a structure shown in Chemical Formula I; the luminescent material includes any one or at least two combinations of the compounds, The organic light-emitting display panel includes an anode, a cathode, and an organic layer located between the anode and the cathode; the material of the organic layer includes any one or a combination of at least two of the compounds; the The organic light emitting display device includes the organic light emitting display panel. ΔE of the compounds provided by the invention st ≤0.30eV, when used in an organic light-emitting display panel, it can further improve the luminous efficiency of the device.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescent materials, in particular to a compound, a luminescent material, an organic light emitting display panel and an organic light emitting display device. Background technique [0002] Organic electroluminescent devices are self-luminous devices, so they are brighter than liquid crystal devices, have excellent visibility, and can display clearly, so active research has been carried out. So far, in order to realize the practical use of organic electroluminescent devices A variety of improvements have been made to further subdivide the various functions of the laminated structure. By sequentially providing an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode on the substrate, In addition to achieving high efficiency and durability in organic light-emitting devices, extensive res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C07D409/14C07F9/6553C09K11/06H01L51/50H01L51/54H10K99/00
CPCC07F5/02C07D409/14C07F9/655345C09K11/06C09K2211/1096C09K2211/1092C09K2211/1029C09K2211/1044C09K2211/1037H10K85/649H10K85/657H10K85/6576H10K85/6572H10K50/12H10K50/11H10K2101/10H10K85/658C07F5/027C07F7/0816H10K85/40H10K85/322H10K85/636H10K85/654H10K50/15H10K50/16H10K50/81H10K50/82H10K50/171
Inventor 高威张磊代文朋牛晶华邓东阳
Owner TIANMA MICRO ELECTRONICS CO LTD
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