2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound and application thereof

A technology of benzothiadiazole and light-emitting compound, which is applied in the field of D-A-A type near-infrared light-emitting compound, and achieves the effect of improving efficiency roll-off, excellent electroluminescence effect and small efficiency roll-off

Active Publication Date: 2017-08-08
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, although people have not carried out research on infrared OLED (IR-O

Method used

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  • 2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound and application thereof
  • 2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound and application thereof
  • 2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Step 1: Dissolve 3.7 g of triphenylamine borate, 2.43 g of 7-bromo-4-formyl benzo[C][1,2,5]thiadiazole in 100 mL of water and 1, In the mixed solution of 4-dioxane, wherein the volume ratio of water and 1,4-dioxane is 1:10, and 3.45 grams of potassium carbonate and 8% equivalent tetrakistriphenylphosphine palladium are added to the reaction in the bottle. After reflux for 48 hours under the protection of argon, the reaction solution was cooled to room temperature. The solvent was removed to dryness by a rotary evaporator. The reaction solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. Add silica gel and spin-dry the resulting solid to pass through the column with dichloromethane / petroleum ether at a ratio of 4:6 (volume ratio), and spin-dry to obtain 3.45 g of 7-triphenylamine-4-formylbenzo[C][1,2,5 ] Thiadiazole, productive rate ...

Embodiment 2

[0035] Step 1: Put 4.00 g of 4,4'-dimethyltriphenylamine borate and 2.43 g of 7-bromo-4-formylbenzo[C][1,2,5]thiadiazole under the protection of argon Dissolve in a mixed solution of 100 mL of water and 1,4-dioxane, wherein the volume ratio of water and 1,4-dioxane is 1:10, and add 3.45 grams of potassium carbonate and 8% equivalent Tetraphenylphosphine palladium into the reaction flask. After reflux for 48 hours under the protection of argon, the reaction solution was cooled to room temperature. The solvent was removed to dryness by a rotary evaporator. The reaction solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. Add silica gel and spin-dry the resulting solid to pass through the column with dichloromethane / petroleum ether at a ratio of 5:5 (volume ratio), and spin-dry to obtain 3.84 g of 7-(4,4'-dimethyltriphenylamine)-4-formylbenzen...

Embodiment 3

[0038] Step 1: 4.3 g of 4,4'-dimethoxytriphenylamine borate, 2.43 g of 7-bromo-4-formyl benzo[C][1,2,5]thiadiazole under argon protection Dissolve in a mixed solution of 100 mL of water and 1,4-dioxane, wherein the volume ratio of water and 1,4-dioxane is 1:10, and add 3.45 grams of potassium carbonate and 8% equivalent Tetraphenylphosphine palladium into the reaction flask. After reflux for 48 hours under the protection of argon, the reaction solution was cooled to room temperature. The solvent was removed to dryness by a rotary evaporator. The reaction solid was dissolved in 80 mL of dichloromethane, and the organic layer was washed three times with 50 mL of water. The organic layer was dried over anhydrous sodium sulfate and spin-dried. Add silica gel and spin-dry the resulting solid to pass through the column with dichloromethane / petroleum ether at a ratio of 3:7 (volume ratio), and spin-dry to obtain 3.85 g of 7-(4,4'-dimethoxytriphenylamine)-4-aldehyde Benzo[C][1,2,5...

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Abstract

The invention provides a 2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound and application thereof. The chemical structure of the 2,1,3-Benzothiadiazole-based D-A-A type near-infrared luminous compound is described in the description, wherein 2,1,3-Benzothiadiazole is taken as a main body, A is cyano, pyridine, sulfuryl or bis(2,4,6-trimethylphenyl) borane; D is diphenylamine, triphenylamine, 4,4'-dimethyl diphenylamine, 4,4'-dimethyl triphenylamine, 4,4'-dimethoxy diphenylamine or 4,4'-dimethoxy triphenylamine. The D-A-A type near-infrared luminous compound provided by the invention not only maintains the intense interaction of D-A, but also has higher fluorescence quantum yield. The luminescent spectrum and quantum yield of the luminous compound can be adjusted by adjusting the intensity of the D-A, so that the balance of the D-A is realized, and the efficiency of a near-infrared organic light emitting diode is further increased.

Description

technical field [0001] The invention relates to the technical field of near-infrared organic optoelectronic materials, in particular to D-A-A type near-infrared luminescent compounds based on benzothiadiazole and applications thereof. Background technique [0002] As we all know, the 21st century is an era of exponentially increasing information, and information display technology, as the most important symbol of this era, has attracted much attention. There is no doubt that the rapid development of information display technology has put forward higher and higher requirements for display technology. As an important means for human beings to contact the external environment, image display plays an irreplaceable role in human life and work. In addition to the diligent pursuit of daily display and image technology, special-purpose infrared display technology is also gradually showing its importance. This is because it has an irreplaceable use of visible light not only in conv...

Claims

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Application Information

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IPC IPC(8): C07D285/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D285/14C09K2211/1037C09K2211/1014C09K2211/1007H10K85/631H10K85/657H10K50/11
Inventor 廖良生王亚坤蒋佐权
Owner SUZHOU UNIV
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