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Organic electroluminescent material, and preparation method and application thereof

An electroluminescent material and luminescent technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of poor blue light color purity, achieve good blue light luminescence performance and stability, mild reaction conditions, The effect of easy operation

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Bis[2-(4',6'-difluorophenyl)pyridine-N,C2'](2-pyridinecarbonyl)iridium (FIrpic, whose structural formula is shown below) disclosed by Holmes R J, Forrest S R et al. (App.Phys.Lett.,2003,82(15):2422-2424) is currently the most reported blue light organic electrophosphorescent material with the best comprehensive performance, but the blue light emitted by FIrpic is sky blue, and the color purity of blue light Poor, the CIE of OLED devices made with FIrpic varies between (0.13~0.17,0.29~0.39), which is far from the CIE of standard blue light (0.137,0.084)

Method used

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  • Organic electroluminescent material, and preparation method and application thereof
  • Organic electroluminescent material, and preparation method and application thereof
  • Organic electroluminescent material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] This example provides a bis(2-(2',6'-difluoropyridin-3'-yl)-5-methoxypyrimidine-N,C 4 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P1:

[0068]

[0069] The preparation steps of the above P1 are as follows:

[0070] S10. Provide compound A1 (2-bromo-5-methoxypyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formula:

[0071]

[0072] S20. Synthesis of compound C1 (2-(2',6'-difluoropyridin-3'-yl)-5-methoxypyrimidine)

[0073] Under nitrogen protection, compound A1 (1.89g, 10mmol), compound B (1.91g, 12mmol) and Pd(PPh 3 ) 4 (0.58mg, 0.5mmol) was dissolved in 35mL of toluene, and then 15mL of an aqueous solution containing potassium carbonate (2.76g, 20mmol) was added, and the reaction was stirred at 90°C for 10 hours; Extract with methane, separate liquid, then wash with water until neutral, then dry with anhydrous magnesium sulf...

Embodiment 2

[0099] This example provides a bis(2-(2',6'-difluoropyridin-3'-yl)-4-hexyloxypyrimidine-N,C 4 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P2:

[0100]

[0101] The preparation steps of above-mentioned P2 are as follows:

[0102] S10, providing compound A2 (2-bromo-4-hexyloxypyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formula:

[0103]

[0104] S20. Synthesis of compound C2 (2-(2',6'-difluoropyridin-3'-yl)-4-hexyloxypyrimidine)

[0105] Under nitrogen protection, compound A2 (1.30g, 5mmol), compound B (0.79g, 5mmol) and Pd(PPh 3 ) 2 Cl 2 (0.14mg, 0.2mmol) was dissolved in 35mL of DMF, and then 15mL of an aqueous solution containing potassium carbonate (2.07g, 15mmol) was added, and stirred at 80°C for 12 hours; Extraction, liquid separation, and then washed with water until neutral, then dried with anhydrous magnesium sulfate an...

Embodiment 3

[0128] This example provides a bis(2-(2',6'-difluoropyridin-3'-yl)-5-eicosyloxypyrimidine-N,C 4 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P3:

[0129]

[0130] The preparation steps of above-mentioned P3 are as follows:

[0131] S10, providing compound A3 (2-bromo-5-eicosyloxypyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formula:

[0132]

[0133] S20. Synthesis of compound C3 (2-(2',6'-difluoropyridin-3'-yl)-5-eicosyloxypyrimidine)

[0134] Under nitrogen protection, compound A3 (0.91g, 2mmol), compound B (0.48g, 3mmol) and tetrakis(triphenylphosphine)palladium (0.07mg, 0.06mmol) were dissolved in 20mL of toluene, and then 10mL containing An aqueous solution of sodium carbonate (0.21g, 2mmol) was stirred at 90°C for 15 hours; after the reaction solution was cooled to room temperature, it was extracted with dichloromethane, separa...

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Abstract

The invention belongs to the field of photoelectric materials, and specifically relates to an organic electroluminescent material. A structural formula is shown in the description. In the formula, R represents alkyl of C1-C20. The organic electroluminescent material has a relatively high LUMO energy level and relatively low HOMO energy level, and is beneficial to blue shift of luminescent wavelengths of the material. The organic electroluminescent material also has relatively high phosphorescence quantum efficiency, relatively good solubility and processability. The invention also provides a preparation method of the organic electroluminescent material, and an application of the organic electroluminescent material in an organic electroluminescent device.

Description

technical field [0001] The invention relates to the field of optoelectronic materials, in particular to an organic electroluminescent material and its preparation method and application. Background technique [0002] Organic electroluminescence refers to a luminescence phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. Due to the limitation of spin statistics theory, the theoretical internal quantum efficiency limit of fluorescent materials is only 25%. How to make full use of the remaining 75% of phosphorescence to achieve higher luminous efficiency has become a hot research direction in this field since then. The complexes of iridium, ruthenium, platinum, etc. can obtain high emission energy from their own triplet state, and the metal iridium (III) compound, due to its good stability, has mild reaction conditions during the synthesis process and has a high electron emission. The luminescence pe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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