Iptycene-containing phosphorescent iridium complex and preparation method thereof and electroluminescent device

A technology of phosphorescent iridium complexes and complexes, which can be used in electric solid devices, electrical components, luminescent materials, etc., can solve problems such as impossible applications, and achieve the effects of low production cost, high efficiency, and reduced concentration quenching.

Active Publication Date: 2017-08-11
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
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  • 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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  • Iptycene-containing phosphorescent iridium complex and preparation method thereof and electroluminescent device
  • Iptycene-containing phosphorescent iridium complex and preparation method thereof and electroluminescent device
  • Iptycene-containing phosphorescent iridium complex and preparation method thereof and electroluminescent device

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Experimental program
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Effect test

Embodiment 1

[0065] A kind of preparation method of the discenyl-containing iridium complex of this embodiment, add 2.00g (7.09mmol) 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=8Hz, 1H), 8.39(d, J=8Hz, 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 and 10 mL (556 mmol) o...

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 H NMR (400Hz, CDCl 3 )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 an iptycene-containing phosphorescent iridium complex and a preparation method thereof and an electroluminescent device and belongs to the field of organic photoelectric materials. The preparation method includes: dissolving 1-formyl triptycene into a dried organic solvent, and subjecting to condensation with an o-amino compound under protection of inert gas and in the presence of a catalyst to obtain cyclometalated ligand containing iptycene structure; dissolving IrCl3 in water, adding the cyclometalated ligand and the organic solvent, and stirring under protection of inert gas to obtain a dichloro-bridged intermediate of iridium; dissolving the dichloro-bridged intermediate in the organic solvent, and stirring with corresponding assistant ligand (L^X) under action of alkali and protection of nitrogen to obtain the iptycene-containing phosphorescent iridium complex. Aiming at the problem that iptycene iridium complexes in the prior art are not suitable for being applied to organic electroluminescent devices, a phosphorescent material wrapped by iptycene is taken as a luminous layer doped in an OLED (organic light-emitting diode) device, and high doping concentration, high spectrum stability and high efficiency can be realized.

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 electroluminescence 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 devi...

Claims

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Application Information

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Patent Type & Authority Applications(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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