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Functionalized picolinic acid double dentate anion ligand and its annular metal iridium complex and uses

An anionic ligand and picolinic acid technology, applied in the fields of compounds containing elements of group 8/9/10/18 of the periodic table, chemical instruments and methods, organic chemistry, etc., can solve low luminous efficiency and restrict polymer Improve the luminous performance, excellent electroluminescent performance, and improve the effect of carrier transport in the development of electrophosphorescent display, reducing the luminous efficiency and life of the device, etc.

Inactive Publication Date: 2007-05-23
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems of electrophosphorescence are: (1) organic small molecule electrophosphorescent materials (guests) are doped in the host material, and under the action of electricity and heat, molecules are prone to aggregation and phase separation, resulting in phosphorescence quenching , reducing the luminous efficiency and lifetime of the device; (2) The maximum luminous efficiency of organic small molecule / polymer electrophosphorescent devices is mostly obtained at lower current densities
When the current density increases, the luminous efficiency of electrophosphorescent devices decreases rapidly; (3) the luminous efficiency of polymer electrophosphorescent devices is generally lower than that of organic small molecule electrophosphorescent devices, which restricts the efficiency of polymer electrophosphorescent devices. Development of Phosphorescent Displays

Method used

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  • Functionalized picolinic acid double dentate anion ligand and its annular metal iridium complex and uses
  • Functionalized picolinic acid double dentate anion ligand and its annular metal iridium complex and uses
  • Functionalized picolinic acid double dentate anion ligand and its annular metal iridium complex and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Synthesis of N'-(4-bromobenzoyl)-4-tert-butylbenzohydrazide

[0040] Add 9.6g (50mmol) of ethyl 4-tert-butylbenzoate, 11.0g (50mmol) of 4-bromobenzoyl chloride and 50mL of anhydrous pyridine into a 250mL three-necked flask, under nitrogen protection, heat and reflux for 15 hours, cool, reduce Pyridine was distilled off under pressure to obtain a yellowish viscous substance. Add water, let it stand overnight, and precipitate out. Suction filtration, the precipitate was washed with water and a small amount of ethanol successively, and dried to obtain 18.0 g of off-white solid, yield 96.0%, m.p.212.0-215.0°C.

Embodiment 2

[0042] Synthesis of 2-(4'-tert-butylphenyl)-5-(4'-bromophenyl)-1,3,4-oxadiazole

[0043] Add 18.0g (46mmol) of the compound of Example 1 and 10mL of freshly distilled phosphorus oxychloride into a 250mL three-neck flask, under the protection of nitrogen, heat and reflux for 4.5 hours to obtain a light brown solution, cool, and evaporate the remaining oxychloride under reduced pressure Phosphorus, to obtain a yellowish viscous substance, which was poured into ice water and left standing overnight, a white precipitate was precipitated, filtered by suction, washed with water and a small amount of ethanol in turn, dried, and recrystallized with DMF to obtain 13.5g of white needles Crystal, yield 82.7%, m.p.132.0~133.0℃. 1 H NMR (400MHz, CDCl 3 , TMS) δppm: 8.03(dd, J=8.3Hz, J=8.2Hz, 4H); 7.68(d, J=8.3Hz, 2H), 7.55(d, J=8.1Hz, 2H), 1.38(s, 9H).

Embodiment 3

[0045] Synthesis of 5-bromo-2-pyridinecarboxylic acid

[0046] Add 5.0g (29mmol) of 5-bromo-2-picoline, 1.8g (29mmol) of potassium hydroxide and 100mL of water into a 250mL three-neck flask, heat to reflux, add 10.0g (64mmol) of potassium permanganate in batches, and react After 10 hours, filter while hot, adjust the pH of the filtrate to about 3 with concentrated hydrochloric acid, precipitate a white precipitate, filter with suction, wash the precipitate with water, and recrystallize with water to obtain 3.0 g of the product. Yield 51.0%. 1 H NMR (400MHz, DMSO) δppm: 8.80 (s, 1H), 8.00 (d, J=8.9Hz, 2H). 13 C NMR (400 MHz, DMSO) δppm: 170, 155, 152, 145, 131, 129.

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Abstract

The invention discloses a kind of functionalized pyridine carboxylic acid bidentate anion auxiliary ligand based on oxadiazole or triarylated amine and its metal iridium complex, as well as its application in electroluminescent devices. Compared with the disclosed 2- pyridine carboxylic acid and beta-diketone auxiliary ligands, the functionalized pyridine carboxylic acid can improve carrier transmission, capture ability and dispersibility in the main material of the dual-ring metal iridium complex through introduction of oxadiazole and triarylated amine. Therefore, luminescent properties of the ring metal iridium complexes based on the functionalized pyridine carboxylic acid auxiliary ligand are higher than that based on traditional 2-pyridine carboxylic acid auxiliary ligand. It is shown that the functionalized pyridine carboxylic acid may replace the traditional 2- pyridine carboxylic acid and beta-diketone as the auxiliary ligand, and is widely used to synthesize the red, green and blue three-color dual-ring metal iridium complexes electrophosphorescent materials with improved luminescent properties.

Description

technical field [0001] The present invention relates to the field of organic electroluminescent materials, in particular to a class of 2-pyridinecarboxylic acid bidentate anion ligands containing oxadiazole and triarylamine functional groups and their bicyclic iridium metal complex electrophosphorescent materials and their electroluminescent materials. applications in the field of luminescence. Background technique [0002] Since 1998, the Forrest research group of Princeton University in the United States first reported platinum-porphyrin complexes (PtOEt) efficient organic electrophosphorescent devices (M.A.Baldo, D.F.O'Brien, Y.You, A.Shoustikov, S.Sibley, M.E.Thompson , S.R.Forrest, Nature, 1998, 395, 151.), organic / polymer electrophosphorescence has attracted the attention of researchers all over the world, and has achieved rapid development. Different from electroluminescence, electrophosphorescence is considered to be the most effective way to realize high luminous e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D213/79C07F15/00H01L51/54
Inventor 朱卫国朱美香甘泉杨玉萍胡峥勇
Owner XIANGTAN UNIV
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