A kind of dienyl phosphorescent iridium complex and its preparation method and electroluminescent device

A technology of phosphorescent iridium complexes and alkenyl phosphorescence, applied in the direction of electric solid devices, luminescent materials, electrical components, etc., can solve problems such as impossible applications, and achieve the effects of low production cost, easy implementation, and high efficiency

Active Publication Date: 2019-08-16
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantage is that the complex cannot be applied to OLED devices, and triptycene only plays the role of a skeleton in the complex

Method used

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  • A kind of dienyl phosphorescent iridium complex and its preparation method and electroluminescent device
  • A kind of dienyl phosphorescent iridium complex and its preparation method and electroluminescent device
  • A kind of dienyl phosphorescent iridium complex and its preparation method and electroluminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] A kind of preparation method of the discenyl-containing iridium complex of the present embodiment, add 2.00g (7.09 mmol) 1-formyl triptycene, 0.87g (7.09mmol) o-aminothiophenol and 15mL (194mmol) of anhydrous N,N-dimethylformamide. Heated to 120°C and reacted for 24h under nitrogen atmosphere. After the reaction is complete, add 20 mL of water, extract with ethyl acetate, wash the organic phase with water, dry with anhydrous sodium sulfate and spin dry, use petroleum ether: dichloromethane = 1: 1 to pass through the column, and spin dry to obtain 2-(1- Tridecenyl) benzothiazole ring metallation ligand white solid 2.30g, yield 80%. 1 H NMR (400Hz, CDCl 3 )δ5.64(s, 1H), 7.06(s, 1H), 7.10-7.16(m, 5H), 7.51-7.63(m, 7H), 7.68(t, J=8Hz, 1H), 8.05(d, J=8 Hz, 1H), 8.39 (d, J=8 Hz, 1H).

[0066] Take 0.77g (2mmol) 2-(1-triadenyl) benzothiazole, 0.35g (1mmol) iridium trichloride trihydrate into the sealed tube, then add 30mL (310mmol) ethylene glycol ether to the sealed tube ...

Embodiment 2

[0072] A kind of preparation method of the discenyl-containing iridium complex of the present embodiment, 0.20g (0.1mmol) dichloro bridge intermediate, 0.05g (0.4mmol) 2-picolinic acid and 0.14g (1mmol) potassium carbonate are added To the sealed tube, add 20 mL of dichloromethane into the sealed tube, and heat to 60° C. for 5 h. After the reaction is completed, the product is separated by column chromatography to obtain (TPS) 2 Ir(Pic) orange-red solid 0.023g, yield 16% (yield is related to the reaction raw material, different raw material yield is different). (TPS) 2 The NMR spectrum of Ir(Pic) is: 1 H NMR (400Hz, CDCl 3 )δ5.17(s, 1H), 5.27(s, 1H), 5.73(d, J=9.7Hz, 1H), 6.08-6.16(m, 2H), 6.41(d, J=7.8Hz, 2H), 6.66(d, J=7.9Hz, 1H), 6.72(d, J=8.0Hz, 1H), 6.86-7.10(m, 9H), 7.17-7.25(m, 2H), 7.30-7.55(m, 10H) , 7.66-7.80 (m, 2H), 7.90-8.00 (m, 2H), 8.10 (d, J=7.4Hz, 1H), 8.40-8.46 (m, 1H).

[0073]

Embodiment 3

[0075] A kind of preparation method of the discenyl-containing iridium complex of the present embodiment, 0.20g (0.1mmol) dichloro bridge intermediate, 0.054g (0.2mmol) 3-trifluoromethyl-5-(2-( 4-tert-butyl)pyridyl)pyrazole and 0.14g (1mmol) potassium carbonate were added into the locked tube, then 20mL of dichloromethane was added into the locked tube, and reacted at 60°C for 5h. After the reaction is complete, the product is separated by column chromatography. Get (TPS) 2 Ir(Bpz) orange-red solid 0.019g, yield 15%.(TPS) 2 The NMR spectrum of Ir(Bpz) is: 1 HNMR (400Hz, CDCl3) δ1.25(s, 9H), 5.22(s, 1H), 5.26(s, 1H), 5.92(d, J=7.6Hz, 1H), 5.98(d, J=7.5Hz, 1H), 6.07(d, J=8.5Hz, 1H), 6.45(d, J=4.8Hz, 2H), 6.70-6.84(m, 6H), 6.87-7.06(m, 9H), 7.16 (t, J=7.3Hz, 1H), 7.20(s, 1H), 7.28-7.39(m, 5H), 7.42-7.50(m, 4H), 7.51(s, 1H), 7.88(t, J=8.2Hz, 2H ). 19 F NMR (CDCl 3 , 367MHz) δ-59.81 (s, 3F).

[0076]

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Abstract

The invention discloses a discenyl-containing phosphorescent iridium complex, a preparation method thereof and an electroluminescent device, belonging to the field of organic photoelectric materials. The 1-formyl tripcene is dissolved in a dry organic solvent, and under the protection of an inert gas and the presence of a catalyst, it undergoes condensation reaction with an ortho-amino compound to obtain a cyclometallation ligand containing a diene structure. IrCl 3 Dissolve in water, add a cyclometalation ligand containing a diene structure and an organic solvent, and stir under the protection of an inert gas to obtain a dichloro bridge intermediate of iridium. The dichloro bridge intermediate of iridium is dissolved in an organic solvent, and the corresponding auxiliary ligand (L^X) is stirred under nitrogen protection under the action of a base to obtain a discenyl iridium complex. Aiming at the problem that the discene-based iridium complexes in the prior art are not suitable for application in organic electroluminescent devices, the present invention uses the discene-wrapped phosphorescent material and uses it as the light-emitting layer doped in OLED devices to achieve High doping concentration, good spectral stability and high efficiency.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, in particular to a discenyl-containing phosphorescent iridium complex, a preparation method thereof and an electroluminescent device. Background technique [0002] Compared with liquid crystal displays, organic electroluminescent devices (Organic Light-emitting Diodes, OLEDs) have many advantages such as low driving voltage, high luminous brightness and efficiency, wide luminous viewing angle, fast response speed, small device thickness, and flexible display. It has great application prospects in the fields of information display and solid-state lighting, and is known as the next-generation "star" flat panel display technology. [0003] According to the law of spin statistics, the upper limit of the highest internal quantum efficiency of electroluminescent devices in organic electroluminescent materials is 25%, which causes the luminous efficiency of organic electroluminescent devic...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 童碧海胡伟康马秀芳周世雄梅群波徐靖宇时鹏胡旭成姜毅
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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