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Blue ray organic electroluminescent material and preparation method and application thereof

An electroluminescence, electromechanical technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as poor blue color purity, and achieve the effect of simple and easy preparation method and convenient operation.

Inactive Publication Date: 2014-12-03
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • 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, etc. (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 Not good, the CIE of each OLED device produced 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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  • Blue ray organic electroluminescent material and preparation method and application thereof
  • Blue ray organic electroluminescent material and preparation method and application thereof
  • Blue ray organic electroluminescent material and preparation method and application thereof

Examples

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Embodiment 1

[0072] This embodiment provides a kind of bis(2-(2',6'-difluoropyridine-3'-yl)pyrimidine-N, C 4' )(2,4-bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole) iridium complex, its chemical structure is shown in P1:

[0073]

[0074] The preparation steps of the above P1 are as follows:

[0075] S10. Synthesis of compound C1 (2-(2',6'-difluoropyridine-3'-yl)pyrimidine)

[0076] Provide compound A1 (2-bromopyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formulas:

[0077]

[0078] Under the protection of nitrogen, 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, then added 20mL of potassium carbonate (2.76g, 20mmol) aqueous solution, stirred at 100 ℃ for 8 hours; after the reaction solution cooled to room temperature, use dichloromethane Extraction, separation, and then wash with water to neutral, then dry with anhydrous magnesium sulfate and filter, the filtrate ...

Embodiment 2

[0103] This embodiment provides a bis(2-(2',6'-difluoropyridin-3'-yl)-5-methylpyrimidine-N,C4')(2,4-bis(trifluoromethyl) )-5-(pyridine-2'-yl)pyrrole) iridium complex, its chemical structure is shown in P2:

[0104]

[0105] The preparation steps of the above P2 are as follows:

[0106] S10. Synthesis of compound C2 (2-(2',6'-difluoropyridin-3'-yl)-5-methylpyrimidine)

[0107] Provide compound A2 (2-bromo-5-methylpyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formula:

[0108]

[0109] Under the protection of nitrogen, compound A2 (1.73g, 10mmol), compound B (1.59g, 10mmol) and Pd(PPh 3 ) 2 Cl 2 (0.28mg, 0.4mmol) was dissolved in 50mL of DMF, then added 25mL of sodium carbonate (3.18g, 30mmol) aqueous solution, stirred at 90 ℃ for 10 hours; after the reaction solution cooled to room temperature, extracted with dichloromethane , Separate the liquids, then wash with water to neutral, then dry with anhydrous magnesium sulfate and ...

Embodiment 3

[0132] This embodiment provides a kind of bis(2-(2',6'-difluoropyridine-3'-yl)-5-tert-butylpyrimidine-N, C 4' )(2,4-Bis(trifluoromethyl)-5-(pyridine-2'-yl)pyrrole) iridium complex, its chemical structure is shown in P3:

[0133]

[0134] The preparation steps of the above P3 are as follows:

[0135] S10. Synthesis of compound C3 (2-(2',6'-difluoropyridine-3'-yl)-5-tert-butylpyrimidine)

[0136] Provide compound A3 (2-bromo-5-tert-butylpyrimidine) and compound B (2,6-difluoropyridine-3-boronic acid) represented by the following structural formula:

[0137]

[0138] Under the protection of nitrogen, 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, then 15mL of sodium carbonate (1.06g, 10mmol)-containing aqueous solution was added and stirred at 85°C for 12 hours; after the reaction solution was cooled to room temperature, it was extracted with dichloromethane Separate the liquids, wash with water to neutral, th...

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Abstract

The invention belongs to the field of photoelectric materials, and in particular relates to a blue ray organic electroluminescent material with the structural formula shown as P, wherein R is hydrogen atom or C1-C20 alkyl. The blue ray organic electroluminescent material has higher LUMO (lowest unoccupied molecular orbital) energy level and lower HOMO (highest occupied molecular orbital) energy level, is conducive to blue shift of material luminescent wavelength, and also has higher phosphorescence quantum efficiency and better dissolution properties and processing properties. The invention also provides a preparation method of the blue ray organic electroluminescent material and application of the blue ray organic electroluminescent material in organic electroluminescent devices.

Description

Technical field [0001] The invention relates to the field of optoelectronic materials, in particular to a blue organic electroluminescent material and a preparation method and application thereof. 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% phosphorescence to achieve higher luminous efficiency has become a hot research direction in this field. The complexes of iridium, ruthenium, platinum, etc. can obtain high emission energy from their own triplet state. Among them, the metal iridium (III) compound, due to its good stability, has mild reaction conditions during the synthesis process, and has high electricity The luminescence performance...

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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