Compound, display panel and display apparatus

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

Active Publication Date: 2019-07-16
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, few TADF materials have been found so far, so it is u

Method used

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  • Compound, display panel and display apparatus
  • Compound, display panel and display apparatus
  • Compound, display panel and display apparatus

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 3 times rapidly, and passed Add 50 mL of toluene to the syringe. The mixture was heated to reflux for 3 hours under a stream of nitrogen. 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 the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain P7 (3.4 mmol, 68%).

[0105] MALDI-TOF MS: Calculated m / z: 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-neck flask. Inject 100mL of toluene into the two-necked flask (pass N in advance 2 15min to remove oxygen), and then added dropwise 12mL concentration of 1M K 2 CO 3 Aqueous solution (pass N in advance 2 15min except oxygen), 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 afforded solid S5 (5.6 mmol, 75%).

[0111] MALDI-TOF MS: m / z calcd:...

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-neck flask, 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 a stream of nitrogen. 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-TOF MS: m / z calculated: C38H30Br2N2S2: 736.0; measured: 736.2

[0121]

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

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PUM

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Abstract

The invention provides a compound with a D-pi-A type chemical structure. The compound has the structure shown in the formula I, wherein D1 and D2 represent electron-donating groups, m, n, p and q areindependently selected from 0, 1 or 2, X and Y are independently selected from one of an S atom, an N atom, an O atom, a Si atom, and a C atom, and D1 and D2 are each independently selected from at least one of a substituted or unsubstituted C12-C40 carbazolyl and a derivative group thereof, a substituted or unsubstituted C12-C40 diphenylamino group and a derivative group thereof, a substituted orunsubstituted C18-C60 triphenylamino group and a derivative group thereof, and a C12-C40 acridinyl and a derivative group thereof, A1 and A2 represent electron-accepting groups, and A1 and A2 are selected from at least one of a nitrogen-containing heterocyclic substituent, a cyano group-containing substituent, an aryl boron substituent, a carbonyl group-containing substituent, a fluorine-containing substituent, a sulfone substituent, and a phosphoxy group-containing substituent. The D-pi-A type structure is formed by linking the electron-donating group and the electron-accepting group to an aromatic heterocyclic mother nucleus.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescence materials, in particular to a compound, 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 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...

Claims

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Application Information

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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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