Compound, display panel and display device

A display panel and compound technology, applied in silicon organic compounds, compounds of group 5/15 elements of the periodic table, compounds of group 4/14 elements of the periodic table, etc.

Active Publication Date: 2021-08-27
WUHAN TIANMA MICRO ELECTRONICS CO LTD +1
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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

[0102] Synthesis of Compound P7

[0103]

[0104]S1 (5.0mmol), 9,9-dimethyl-9,10-dihydroacridine S2 (10.4mmol), (dibenzylideneacetone) dipalladium (0) (0.2mmol), sodium tert-butoxide (14.0mmol), 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (0.2mmol) were put into a 250mL three-necked flask, and while stirring, the degassing and nitrogen replacement were repeated three times rapidly, and passed Add 50 mL of toluene to the 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 P7 (3.4 mmol, 68%).

[0105] MALDI-TOFMS: m / z calculated value: C 42 h 28 N 6 S 2 : 680.2; measured value: 680.5.

[0106] Elemental Analysis Calculated: C, 74.09; H, 4.15; N, 12....

Embodiment 2

[0108] Synthesis of compound P23

[0109]

[0110] Under nitrogen protection, weigh compound S3 (7.5mmol), S4 (15.5mmol), [Pd 2 (dba) 3 ]·CHCl 3 (0.3mmol) and HP(tBu) 3 ·BF 4 (0.6mmol), was added to a 250mL two-necked flask. Inject 100mL of toluene into the two-necked flask (pass N in advance 2 15min to remove oxygen), and then add 12mL of K with a concentration of 1M dropwise 2 CO 3 Aqueous solution (pass N in advance 2 15min to remove oxygen), and stirred overnight at room temperature. After the reaction was completed, 100 mL of deionized water was added, and then 2 mL of 2M HCl was added dropwise. 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 S5 (5.6 mmol, 75%).

[0111] MALDI-TOFMS: ...

Embodiment 3

[0117] Synthesis of Compound P29

[0118]

[0119] S7 (2.7mmol), 9,9-dimethyl-9,10-dihydroacridine S2 (5.7mmol), (dibenzylideneacetone) dipalladium (0) (0.35mmol), sodium tert-butoxide (10.0mmol) and tri-tert-butylphosphine tetrafluoroborate (0.7mmol) were put into a 500mL three-necked flask, and while stirring, degassing and nitrogen replacement were repeated three 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 P23 (1.60 mmol, 59%).

[0120] MALDI-TOFMS: m / z calculated: C38H30Br2N2S2: 736.0; measured: 736.2

[0121]

[0122] In a 250ml three-necked flask, first mix S9 (7.5mmol), pinacol dibora...

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PUM

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Abstract

The present invention provides a kind of compound with D-π-A type chemical structure, and described compound has the structure shown in chemical formula I; D 1 and D 2 Represents an electron-donating group; m, n, p and q are independently selected from 0, 1 or 2; X and Y are independently selected from one of S atom, N atom, O atom, Si atom, and C atom; D 1 and D 2 Each independently selected from substituted or unsubstituted C12-C40 carbazolyl and derivatives thereof, substituted or unsubstituted C12-C40 diphenylamino and derivatives thereof, substituted or unsubstituted C18-C18- At least one of the triphenylamine group of C60 and its derivative group, the acridinyl group of C12-C40 and its derivative group; A 1 and A 2 represents an electron-accepting group, and A 1 and A 2 Selected from nitrogen-containing heterocyclic substituents, cyano-containing substituents, aryl boron-containing substituents, carbonyl-containing substituents, fluorine-containing substituents, sulfone-containing substituents and phosphorus-containing oxygen-based substituents at least one. In the invention, an electron-donating group and an electron-accepting group are connected on the parent nucleus of the aromatic heterocyclic ring to form a D-π-A structure.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C07D491/048C07F5/02C07F7/08C07F9/6571C07D413/14C07D405/14C07F9/6558C07D519/00C09K11/06H01L51/50H01L51/54
CPCC07D409/14C07D491/048C07F5/027C07F7/0816C07F9/657163C07D413/14C07D405/14C07F9/65586C07D519/00C09K11/06C09K2211/1007C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1044C09K2211/1059C09K2211/104C09K2211/1088C09K2211/1092C09K2211/1096H10K85/655H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/40H10K85/6572H10K50/11H10K2101/40H10K50/12
Inventor 高威张磊代文朋牛晶华
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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