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Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof

A technology of phenylpyridine iridium and phenylpyridine, which is applied in the field of multi-substituted phenylpyridine iridium complexes and their preparation, can solve the problems of reducing luminous quantum efficiency and the like, and achieve the effect of high quantum efficiency

Inactive Publication Date: 2017-01-11
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for most pure organic molecules and light metal complexes, due to the long lifetime and spin prohibition of the triplet state, they exhibit non-radiative transitions, so only the singlet state can be used, which greatly reduces the Luminous Quantum Efficiency

Method used

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  • Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof
  • Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof
  • Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof

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preparation example Construction

[0033] The preparation method of the multi-substituted phenylpyridine iridium (III) complex comprises the following steps:

[0034] Step 1, under inert gas conditions, in an alkoxyethanol solvent system, react polysubstituted phenylpyridine with iridium trichloride trihydrate in a molar ratio of 2 to 2.5:1 at 110°C to obtain iridium (III) chlorine bridge dimer;

[0035] Step 2, in the dichloromethane solvent system, in the presence of anhydrous potassium carbonate, the iridium (III) chlorine bridge dimer and 2-pyridinecarboxylic acid or 3-trifluoromethyl-5-pyridine triazole by 1: 1.1~1.5 molar ratio reacted at 25°C to obtain multi-substituted phenylpyridine iridium (III) complexes,

[0036] Wherein, the multi-substituted phenylpyridine structural formula is shown in formula III:

[0037] R 1 , R 2 , R 3 , R 4 , R 5 each independently hydrogen, fluorine, methyl or trifluoromethyl.

[0038] The multi-substituted phenylpyridine iridium (III) complex of the present inven...

Embodiment 1

[0046] Complex [3-CF 3 -4-Fppy] 2 Synthesis of Ir(pic)

[0047] (1) Synthesis of 2-(3-trifluoromethyl-4-fluorophenyl)pyridine

[0048] Take 1.58g of 2-bromopyridine, 2.08g of 3-trifluoromethyl-4-fluorophenylboronic acid, tetrakis(triphenylphosphine)palladium(Pd(PPh 3 ) 4 ) 380mg, 8mL saturated aqueous potassium carbonate solution, 8mL anhydrous methanol, and 25mL toluene were sequentially added into a three-necked flask with a stirring bar, nitrogen gas was passed, and the reaction was refluxed at 85°C for 15h. After the reaction was completed, it was cooled to room temperature, diluted with a large amount of dichloromethane, washed three times with water, dried the organic phase with anhydrous sodium carbonate, spin-dried under reduced pressure, petroleum ether: ethyl acetate (70:1) column chromatography to obtain a colorless oily liquid, Yield 91%. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.70 (ddd, J = 4.8, 1.6, 0.9Hz, 1H), 8.28 (dd, J = 6.9, 2.2Hz, 1H), 8.17 (ddd, J = 8.1, ...

Embodiment 2

[0056] Complex [3-CF 3 -4-Fppy] 2 Synthesis of Ir(fptz)

[0057] (1) Synthesis of 3-trifluoromethyl-5-pyridine triazole (fptz)

[0058] (i) Add 2-cyanopyridine and sodium methylate in a molar ratio of 10:1 (5g:259mg) and 50mL of methanol into a two-necked flask filled with nitrogen, stir at room temperature for 12 hours under nitrogen protection, and then add 2-cyanopyridine Pyridine equivalent ammonium chloride (2.57g), stirred at room temperature for 16h, then, under reflux conditions (65°C), reacted for 4h, returned to room temperature and filtered to remove unreacted ammonium chloride, and removed the solvent in vacuum at room temperature , washed with ether several times in order to further remove unreacted ammonium chloride, and filtered to obtain 2-aminopyridine hydrochloride in the form of white needles.

[0059] (ii) Add ethyl trifluoroacetate and hydrazine hydrate in a molar ratio of 1:1.2 (7g:2.96g) and 30mL of dewatered THF solution into a two-necked flask fille...

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Abstract

The invention provides a multi-substituted phenylpyridine iridium (III) complex and a preparation method and application thereof. The structural formula of the complex is as shown in the formula I or II. Please see the formula in the description. R1, R2, R3, R4 and R5 are independently hydrogen, fluorine, methyl or trifluoromethyl. The preparation method includes the steps that multi-substituted phenylpyridine reacts with iridium chloride trihydrate to obtain iridium (III) chloro-bridged dimer; then the iridium (III) chloro-bridged dimmer reacts with 2-pyridinecarboxylic acid or 3-trifluoromethyl-5-pyridyl triazole, and the multi-substituted phenylpyridine iridium (III) complex can be obtained. The multi-substituted phenylpyridine iridium (III) complex has the advantages of blue light dual emission, extremely high quantum efficiency and the like, can serve as an electroluminescent phosphorescent material and a phosphorescent doping material to be used in an organic electroluminescent device, can achieve blue light emission, and can be doped with yellow-orange light to achieve white light emission.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, in particular to a multi-substituted phenylpyridine iridium (III) complex and its preparation method and application. Background technique [0002] Since C.W.Tang first discovered octahydroxyquinoline aluminum (Alq 3 ), the photoluminescence and electroluminescence of organic compounds have received widespread attention. These organic light-emitting compounds are widely used in the fields of organic light-emitting diodes (OLEDs), organic sensing, and bioimaging. According to quantum theory, common organic luminescence is divided into fluorescence luminescence and phosphorescence luminescence. However, for most pure organic molecules and light metal complexes, due to the long lifetime and spin prohibition of the triplet state, they exhibit non-radiative transitions, so only the singlet state can be used, which greatly reduces the Luminous Quantum Efficiency. Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342
Inventor 赵强张元兵刘淑娟陶鹏许文娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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