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Blue ray organic electroluminescent material and preparation method and application thereof

An electroluminescence, electromechanical technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of poor blue light color purity, and achieve the effect of improving blue light emitting performance, good film-forming performance, and improving luminous efficiency.

Inactive Publication Date: 2015-02-04
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • 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) (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 purity of the blue light color is not good, so it is made with FIrpic The CIE of OLED devices 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

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] combine figure 1 The schematic diagram of the preparation process of the blue-light organic electroluminescent material shown in this example provides a bis(2-(3',5'-difluoro-4'-cyanophenyl)pyrimidine-N,C 2' )(5-(2'-pyridyl)-1,2,3,4-tetrazole) iridium complex, the chemical structure of which is shown in P1:

[0056]

[0057] The preparation steps of the above P1 are as follows:

[0058] S10. Synthesis of compound C1 (2-(3',5'-difluoro-4'-cyanophenyl)pyrimidine)

[0059] Compound A1 (2-bromopyrimidine) and compound B (3,5-difluoro-4-cyanophenylboronic acid) represented by the following structural formulas are provided:

[0060]

[0061] Under nitrogen protection, compound A1 (1.59g, 10mmol), compound B (2.20g, 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; Extraction, liquid separation, ...

Embodiment 2

[0086] This example provides a bis(2-(3',5'-difluoro-4'-cyanophenyl)-5-methylpyrimidine-N,C 2 ')(5-(2'-pyridyl)-1,2,3,4-tetrazole) iridium complex, the chemical structure of which is shown in P2:

[0087]

[0088] The preparation steps of above-mentioned P2 are as follows:

[0089] S10. Synthesis of compound C2 (2-(3',5'-difluoro-4'-cyanophenyl)-5-methylpyrimidine)

[0090] Compound A2 (2-bromo-5-methylpyrimidine) and compound B (3,5-difluoro-4-cyanophenylboronic acid) represented by the following structural formulas are provided:

[0091]

[0092] Under nitrogen protection, compound A2 (1.73g, 10mmol), compound B (1.83g, 10mmol) and Pd(PPh 3 ) 2 Cl 2 (0.28mg, 0.4mmol) was dissolved in 50mL of DMF, then 25mL of an aqueous solution containing sodium carbonate (3.18g, 30mmol) was added, and stirred at 90°C for 8 hours; after the reaction solution was cooled to room temperature, it was extracted with dichloromethane , liquid separation, then washed with water until neu...

Embodiment 3

[0115] This example provides a bis(2-(3',5'-difluoro-4'-cyanophenyl)-5-tert-butylpyrimidine-N,C 2' )(5-(2'-pyridyl)-1,2,3,4-tetrazole) iridium complex, the chemical structure of which is shown in P3:

[0116]

[0117] The preparation steps of above-mentioned P3 are as follows:

[0118] S10. Synthesis of compound C3 (2-(3',5'-difluoro-4'-cyanophenyl)-5-tert-butylpyrimidine)

[0119] Compound A3 (2-bromo-5-tert-butylpyrimidine) and compound B (3,5-difluoro-4-cyanophenylboronic acid) represented by the following structural formulas are provided:

[0120]

[0121] Under nitrogen protection, compound A3 (2.15g, 10mmol), compound B (2.56g, 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; after the reaction solution was cooled to room temperature, it was extracted with dichloromethane , liquid separation, then washed wit...

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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 or C1-C20 alkoxy. 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-light 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 lumin...

Claims

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Application Information

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