Organic electroluminescent material, 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, reduce the probability of non-radiative transition, good blue light luminescence performance and Stability, the effect of reducing the self-quenching phenomenon

Inactive Publication Date: 2015-01-21
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
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  • Application Information

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] This example provides a bis(2-(2',6'-difluoropyridin-4'-yl)pyrimidine-N,C 3 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P1:

[0071]

[0072] The preparation steps of the above P1 are as follows:

[0073] S10, providing compound A1 (2-bromopyrimidine) and compound B (2,6-difluoropyridine-4-boronic acid) represented by the following structural formula:

[0074]

[0075] S20. Synthesis of compound C1 (2-(2',6'-difluoropyridin-4'-yl)pyrimidine)

[0076] Under nitrogen protection, compound A1 (1.59g, 10mmol), compound B (1.91g, 12mmol) and Pd(PPh 3 ) 4 (0.58mg, 0.5mmol) was dissolved in 40mL of toluene, and then 20mL of an aqueous solution containing potassium carbonate (2.76g, 20mmol) was added, and the reaction was stirred at 100°C for 6 hours; Extract with methane, separate liquid, then wash with water until neutral, then dry with anhydrous magnesium sulfate and filter, evaporate th...

Embodiment 2

[0102] This example provides a bis(2-(2',6'-difluoropyridin-4'-yl)-5-methylpyrimidine-N,C 3 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P2:

[0103]

[0104] The preparation steps of above-mentioned P2 are as follows:

[0105] S10, providing compound A2 (2-bromo-5-methylpyrimidine) and compound B (2,6-difluoropyridine-4-boronic acid) represented by the following structural formula:

[0106]

[0107] S20. Synthesis of compound C2 (2-(2',6'-difluoropyridin-4'-yl)-5-methylpyrimidine)

[0108] Under nitrogen protection, compound A2 (1.73g, 10mmol), compound B (1.76g, 10mmol) and Pd(PPh 3 ) 2 Cl 2 (0.28mg, 0.4mmol) was dissolved in 50mL of DMF, and then 25mL of an aqueous solution containing sodium carbonate (3.18g, 30mmol) was added, and stirred at 90°C for 8 hours; Extract, separate liquid, then wash with water until neutral, then dry with anhydrous magnesium sulfate and filter, the filtrat...

Embodiment 3

[0131] This example provides a bis(2-(2',6'-difluoropyridin-4'-yl)-5-tert-butylpyrimidine-N,C 3 ')(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole)iridium complex, the chemical structural formula of which is shown in P3:

[0132]

[0133] The preparation steps of above-mentioned P3 are as follows:

[0134] S10. Provide compound A3 (2-bromo-5-tert-butylpyrimidine) and compound B (2,6-difluoropyridine-4-boronic acid) represented by the following structural formula:

[0135]

[0136] S20. Synthesis of compound C3 (2-(2',6'-difluoropyridin-4'-yl)-5-tert-butylpyrimidine)

[0137] Under nitrogen protection, compound A3 (2.15g, 10mmol), compound B (2.22g, 14mmol) and Pd(PPh 3 ) 2 Cl 2 (0.21mg, 0.3mmol) was dissolved in 35mL of DMF, and then 15mL of an aqueous solution containing sodium carbonate (1.06g, 10mmol) was added, and stirred at 85°C for 10 hours; extraction, liquid separation, and then washed to neutrality, then dried with anhydrous magnesium sulfate and filter...

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Abstract

The invention belongs to the field of photoelectric materials and particularly relates to an organic electroluminescent material having a following structure formula, wherein R is a hydrogen atom, an alkyl group with a carbon atom number being 1-20 or an alkoxy group with a carbon atom number being 1-20. The organic electroluminescent material includes a cyclometal ligand and an auxiliary ligand 2,4-di(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole. A main body structure of the cyclometal ligand is 2-(2',6'-difluoropyridine-4'-yl)pyrimidine. The organic electroluminescent material can adjust a luminescent wavelength of a blue light, has a high luminescent efficiency, and is good in dissolving performance 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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IPC IPC(8): C09K11/06C07F15/00H01L51/54
Inventor 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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