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Compound, display panel and display device

A technology of compounds and derivatives, applied in the field of organic electroluminescent materials, to achieve the effects of high-efficiency energy transfer, high triplet energy level, and reduced conjugation

Inactive Publication Date: 2019-08-16
SHANGHAI TIANMA AM OLED
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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, so it is urgent to develop new TADF materials that can be used in OLEDs.

Method used

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  • Compound, display panel and display device
  • Compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0114]

[0115] In a 250ml three-necked flask, first mix S1 (30mmol), pinacol diborate (36mmol), (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (0.3mmol) And potassium acetate (75mmol) was added separately, while stirring, degassing and nitrogen replacement were repeated 3 times quickly, and 100mL tetrahydrofuran was added through a syringe. Stir at a certain speed, heat the resulting mixed solution reactant to reflux at a reaction temperature of 80°C for 5 hours; after the reaction is completed, cool to room temperature and add 100ml 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 S2 (24.6 mmol, 82%).

[0116] MALDI-TOF MS: Calculated m / z: C 17 h 17 BFNO 2 S: 329.1; Measured: 329.5.

[0117]

[0118] Under nitrogen protection, weigh compound S2 (25mmol), S3 (25mmol), [Pd 2 (dba) 3 ]·CHCl 3 (0.5mmol) and HP(tBu) ...

Embodiment 2

[0125]

[0126] S6 (10.0mmol), S5 (10.5mmol), (dibenzylideneacetone) dipalladium (0) (0.5mmol), sodium tert-butoxide (14mmol), tri-tert-butylphosphine tetrafluoroborate (1.0mmol) Put it into a 500mL three-neck flask, and while stirring, quickly repeat degassing and nitrogen replacement 3 times, and add 200mL of toluene through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate S7 (8.6 mmol, 86%).

[0127] MALDI-TOF MS: m / z, Calculated: C 28 h 17 BrN 4 S: 520.0; test value: 520.4.

[0128]

[0129] In a 250ml three-necked flask, first, S7 (15.0mmol), pinacol diborate (18mmol), (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II...

Embodiment 3

[0136]

[0137] S6 (5.0mmol), S5 (5.2mmol), (dibenzylideneacetone) dipalladium (0) (0.25mmol), sodium tert-butoxide (8mmol), tri-tert-butylphosphine tetrafluoroborate (0.5mmol) Put it into a 250mL three-neck flask, and while stirring, quickly repeat degassing and nitrogen replacement 3 times, and add 80mL of toluene through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate S12 (3.85 mmol, 77%).

[0138] MALDI-TOF MS: m / z, Calculated: C 31 h 16 BrN 5 S: 569.0; test value: 569.4.

[0139]

[0140] In a 100ml three-necked flask, firstly mix S7 (7.5mmol), pinacol diborate (8.0mmol), (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladiu...

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Abstract

The invention provides a compound with a D-Pi-A type chemical structure. The compound has a structure shown as a chemical formula I, wherein D represents an electron donating group and is selected from at least one of substituted or unsubstituted C12-C40 carbazolyl group, C12-C40 diphenylamino group and C13-C40 acridyl group, the electron donating group D being connected to a benzene ring througha nitrogen atom; the A represents an electron acceptor group and is selected from at least one of a nitrogen heterocyclo-containing substituent, a cyano-containing substituent, a carbonyl-containing substituent, an aryl boron-containing substituent, a phosphine oxide-containing substituent and a sulfuryl-containing substituent; the R1 and R2 are independently selected from a hydrogen atom, an alkyl group, an alkoxy group, A or D; and m is selected from 1, 2, 3, 4 or 5, n is selected from 1, 2 or 3, p is selected from 0, 1, 2, 3 or 4, q is selected from 0, 1 or 2, (m + p < = 5 and n + q <= 3).A novel thermally activated delayed fluorescent material is formed by connecting electron donating groups and electron accepting groups to benzene rings and thiophene rings.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a compound, a display panel and a display device including the compound. Background technique [0002] With the development of electronic display technology, organic light-emitting devices (OLEDs) are widely used in various display devices, and the research and application of OLED light-emitting materials are also increasing. [0003] According to the light-emitting mechanism, the materials used for the OLED light-emitting layer mainly include the following four types: [0004] (1) fluorescent materials; (2) phosphorescent materials; (3) triplet-triplet annihilation (TTA) materials; (4) thermally activated delayed fluorescence (TADF) materials. [0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons is 1:3, so the maximum internal quantum yield of fluorescent materials does not exceed 25...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D413/14C07D417/14C07D491/048C07D495/04C07D519/00C07F5/02C07F9/6558C09K11/06H01L51/54H01L51/50
CPCC07F5/02C07F9/65586C07D409/14C07D491/048C07D495/04C07D519/00C07D413/14C07D417/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1096C09K2211/1033C09K2211/1037H10K85/655H10K85/636H10K85/654H10K85/657H10K85/6576H10K85/6572H10K50/12
Inventor 高威张磊代文朋牛晶华卢艳
Owner SHANGHAI TIANMA AM OLED
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