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Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof

A technology of fluoropyridine carboxylic acid and iridium complexes, which is applied in the field of iridium complex phosphorescent materials and its preparation, which can solve the problems of increasing the difficulty of synthesis conditions, reducing the luminescence of the complexes, and reducing the photon quantum efficiency, and achieving high internal and external quantum yields , Improve luminous performance, easy separation and purification effect

Inactive Publication Date: 2013-12-18
ANHUI UNIVERSITY OF TECHNOLOGY
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Problems solved by technology

The luminescence of the complex was studied by introducing groups such as methyl, benzene ring, and pyrazine into the picolinic acid structure. The results showed that compared with the auxiliary ligand of picolinic acid, the introduction of these selected groups would reduce the photon quantum efficiency. , to reduce the luminescence of the complex; in addition, the document "Journal of the American Chemical Society" (2003, No. 24, No. 125, No. 125, No. 7377-7387) also discloses a series of 2-arylpyridine derivatives as the main ligand. The iridium complex, whose structure is obtained by replacing the hydrogen atom on the benzene ring with a fluorine atom, does have a slight increase in photon quantum efficiency, but because the fluorine atom is relatively active, it is easily affected by the synthesis conditions and then oxidized, making it difficult to prepare and increasing the synthesis conditions difficulty

Method used

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  • Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof
  • Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof
  • Iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as auxiliary ligand and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Weigh 1.995g (7.10mmol) 2,4-diphenylquinoline and 1.0g (2.84mmol) IrCl XH 2 O In a two-necked round bottom flask, inject 3mL (165mmol) deionized water and 15mL (465mmoL) ethylene glycol ether, N 2 Under protection, heat up to 110°C for 24 hours, cool to room temperature, filter, wash the solid with deionized water and ethanol, and dry the dichloro bridge compound of iridium (DPQ) 2 Ir.

[0039] Weigh 0.1g (0.127mmol) iridium dichloro bridge compound and dissolve in 20mL dichloromethane, add 0.09g (0.635mmol) 5-fluoro-2-pyridinecarboxylic acid, 12mL ethanol and 2mL triethylamine, under nitrogen protection, Stir at room temperature for 12 h, evaporate the solvent under reduced pressure, and purify by column chromatography on silica gel with dichloromethane / ethyl acetate (6 / 1, volume ratio) to obtain the iridium complex (DPQ) 2 Ir(5FPic). 1 H NMR (CDCl 3 ,400MHz)δ:8.75(d,J=8.0Hz,1H),7.96(s,1H),7.92(s,1H),7.86(d,J=8.0Hz,1H),7.78(t,J=5.2 Hz,2H),7.68(t,J=6.4Hz,3H),7.42-7...

Embodiment 2

[0042] Weigh 1.995g (7.10mmol) 2,4-diphenylquinoline and 1.0g (2.84mmol) IrCl XH 2 O In a two-necked round bottom flask, inject 3mL (165mmol) deionized water and 15mL (465mmoL) ethylene glycol ether, N 2 Under protection, heat up to 110°C for 24 hours, cool to room temperature, filter, wash the solid with deionized water and ethanol, and dry the dichloro bridge compound of iridium (DPQ) 2 Ir.

[0043] Weigh 0.1g (0.127mmol) iridium dichloro bridge compound and dissolve it in 20mL dichloromethane, add 0.09g (0.635mmol) 2-fluoro-6-pyridinecarboxylic acid, 12mL ethanol and 2mL triethylamine, under nitrogen protection, Stir at room temperature for 12 h, evaporate the solvent under reduced pressure, and purify by column chromatography on silica gel with dichloromethane / ethyl acetate (6 / 1, volume ratio) to obtain the iridium complex (DPQ) 2 Ir(2FPic). 1 H NMR (CDCl 3 ,400MHz)δ:8.92(d,J=8.8Hz,1H),8.05(s,1H),7.99(s,1H),7.89(d,J=7.6Hz,1H),7.79(d,J=7.6 Hz,4H),7.69-7.76(m,1H),7.55-7...

Embodiment 3

[0046] Weigh 1.995g (7.10mmol) 2,4-diphenylquinoline and 1.0g (2.84mmol) IrCl XH 2 O In a two-necked round bottom flask, inject 3mL (165mmol) deionized water and 15mL (465mmoL) ethylene glycol ether, N 2 Under protection, heat up to 110°C for 24 hours, cool to room temperature, filter, wash the solid with deionized water and ethanol, and dry the dichloro bridge compound of iridium (DPQ) 2 Ir.

[0047] Weigh 0.1g (0.127mmol) iridium dichloro bridge compound and dissolve it in 20mL dichloromethane, add 0.09g (0.635mmol) 3-fluoro-2-pyridinecarboxylic acid, 12mL ethanol and 2mL triethylamine, under nitrogen protection, Stir at room temperature for 12 h, evaporate the solvent under reduced pressure, and purify by column chromatography on silica gel with dichloromethane / ethyl acetate (6 / 1, volume ratio) to obtain the iridium complex (DPQ) 2 Ir(3FPic). 1 H NMR (CDCl3 ,400MHz)δ:8.89(d,J=8.8Hz,1H),8.04(s,1H),8.01(s,1H),7.93(d,J=7.6Hz,1H),7.90(d,J=4.8 Hz,1H),7.78(t,J=7.2Hz,4H),7.54-...

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Abstract

The invention discloses an iridium complex phosphorescent material taking fluorinated fluoropyridine carboxylic acid as an auxiliary ligand and a preparation method of the iridium complex phosphorescent material, and belongs to the technical field of photoelectric and phosphorescent materials. According to iridium complexes, 2-aryl quinoline is taken as a main ligand and fluoropyridine carboxylic acid fluorinated derivatives are taken as an auxiliary ligand to synthesize a series of (C^N)2IrLX type iridium complexes, the type and the quantity of the iridium complex phosphorescent material are expanded through different permutations and combinations, and the fluorescence intensity of the iridium complexes is enhanced by modifying the main ligand and adding the auxiliary ligand containing fluorine. Light-emission devices manufactured through the phosphorescent iridium complexes have a very high internal and external quantum yield, very high luminance and very high stability.

Description

technical field [0001] The invention belongs to the technical field of photoelectric phosphorescent materials, and specifically relates to a kind of iridium complex phosphorescent materials with fluoropyridine carboxylic acid as an auxiliary ligand and a preparation method thereof. Background technique [0002] Organic light-emission devices (organic light-emission devices, OLED) have the advantages of wide material selection range, low driving voltage, high luminous brightness and luminous efficiency, fully cured active luminescence, simple preparation process, low cost, and light weight. It is a research hotspot in the fields of materials, information, physics and flat panel display. Among them, the research on electrophosphorescent materials mainly based on heavy metal complexes is the most active. In the group VIII heavy metal complexes of Os, Ru, Pd, Pt and Ir, after they form complexes with organic ligands, the spin-orbit coupling can be significantly improved, which ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F15/00H01L51/54
Inventor 童碧海张曼马鹏刘远远梅群英
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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