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Compound, display panel and display device

A technology of compounds and derivatives, applied in the field of organic electroluminescence materials, to achieve the effects of reducing positive solvation color change effect, improving color purity, and low half-peak width

Pending Publication Date: 2019-07-12
WUHAN 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, 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
  • Compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Synthesis of compound H001

[0083]

[0084] S1 (10.0mmol), 9,9-dimethyl-9,10-dihydroacridine S2 (10.5mmol), (dibenzylideneacetone) dipalladium (0) (0.5mmol), sodium tert-butoxide (14mmol), tri-tert-butylphosphine tetrafluoroborate (1.0mmol) were put into a 500mL three-necked flask, while stirring, degassing and nitrogen replacement were repeated 3 times rapidly, and 200mL toluene was added 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 S3) (6.5 mmol, 65%).

[0085] MALDI-TOF MS: m / z, Calculated: C 27 h 22 BrN: 439.1; Test value: 439.4.

[0086]

[0087] At -78°C, S3 (1.5 mmol) was dissolved in ether (40 mL), and n...

Embodiment 2

[0090] Synthesis of compound H004

[0091]

[0092]At -78°C, S5 (2.5 mmol) was dissolved in ether (120 mL), and n-BuLi (3.5 mmol) in n-hexane was added dropwise to the solution. The reaction solution was continuously stirred for 2 h, slowly warmed to room temperature, and stirred at room temperature for 1 h. The reaction solution was cooled to -78°C again, and 45 mL of S4 (3.0 mmol) in toluene was added dropwise with stirring. Slowly warm to room temperature and stir overnight. All the solvent was distilled off under reduced pressure, and the crude product was collected. The crude product was washed with methanol (3 x 60 mL) and pentane (3 x 60 mL), respectively, and the crude product was collected again. The crude product was purified by silica gel column chromatography with n-hexane:chloroform (5:1) as eluent, and finally purified to give solid S6 (1.73 mmol, 69%).

[0093] Characterization results: MALDI-TOF MS: m / z, calculated value: C 32 h 19 B 2 FN 2 : 472.2; ...

Embodiment 3

[0099] Synthesis of compound H005

[0100]

[0101] At -78°C, S5 (2.0 mmol) was dissolved in ether (120 mL), and n-BuLi (2.5 mmol) in n-hexane was added dropwise to the solution. The reaction solution was continuously stirred for 2 h, slowly warmed to room temperature, and stirred at room temperature for 1 h. The reaction solution was cooled to -78°C again, and 45 mL of a toluene solution of S6 (2.4 mmol) was added dropwise with stirring. Slowly warm to room temperature and stir overnight. All the solvent was distilled off under reduced pressure, and the crude product was collected. The crude product was washed with methanol (3 x 50 mL) and pentane (3 x 50 mL), respectively, and the crude product was collected again. The crude product was purified by silica gel column chromatography with n-hexane:chloroform (5:1) as eluent, and finally purified to give solid S7 (3.25 mmol, 65%).

[0102] Characterization results: MALDI-TOF MS: m / z, calculated value: C 32 h 19 B 2 FN ...

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Abstract

The invention belongs to the technical field of OLED, and provides a compound with a structure shown in a formula (1), wherein D represents an electron donating group containing a nitrogen atom and isconnected to a benzene ring through the nitrogen atom, and A represents an electron accepting group containing a boron atom and is connected to the benzene ring through the boron atom; m and n are respectively selected from 1, 2 and 3; and R11, R12, R13 and R14 are respectively and independently selected from a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a trifluoromethyl group, the electron accepting group A' or the electron donating group D' containing the nitrogen atom. The compound adopts biphenyl as a connecting unit between the electron donating group D and the electron receiving group A, the D and the A achieve effective separation of HOMO and LUMO at different positions of molecules, and two physical processes of intramolecular charge transfer and space charge transfer can be simultaneously formed in the same molecule through connection of the biphenyl between the D and the A units, so that absorption of the molecules to light is improved, and the oscillatorstrength of the molecules is improved.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a compound having TADF properties and containing an aromatic heterocycle, a display panel and a display device comprising 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 material; (2) phosphorescent material; (3) triplet-triplet annihilation (TTA) material 0; (4) thermally activated delayed fluorescence (TADF) material. [0005] For fluorescent materials, according to spin statistics, the ratio of singlet and triplet excitons in excitons is 1:3, so the maximum inter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08C09K11/06H01L51/50H01L51/54H10K99/00
CPCC07F5/027C07F7/0816C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1096C09K2211/1059C09K2211/104H10K85/657H10K85/6572H10K85/40H10K50/12H10K50/11H10K85/658H10K85/636H10K85/633H10K85/654H10K85/6574H10K2101/40H10K2101/20H10K50/81H10K85/322H10K85/656H10K50/82H10K2101/10
Inventor 高威张磊代文朋牛晶华朱红岩
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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