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Blue-ray metal complex and organic electroluminescent device thereof

A technology of metal complexes and blue light, applied in the direction of electric solid devices, electrical components, luminescent materials, etc., can solve the problems of low power efficiency, high driving voltage, etc., achieve power efficiency improvement, lower injection barrier, and increase HOMO energy level Effect

Inactive Publication Date: 2013-04-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, organic electroluminescent devices based on blue-emitting metal complexes often exhibit the disadvantages of high driving voltage and low power efficiency.

Method used

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  • Blue-ray metal complex and organic electroluminescent device thereof
  • Blue-ray metal complex and organic electroluminescent device thereof
  • Blue-ray metal complex and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Synthesis of Compound I1

[0082] The reaction formula is as follows:

[0083]

[0084] Synthesis of 4-methoxy-2′,6′-difluoro-2,3′-bipyridine:

[0085] Under an inert atmosphere, 10 mL of 2M potassium carbonate aqueous solution and 30 mL of tetrahydrofuran were added to 2-bromo-4-methoxypyridine (1.88 g, 10 mmol), (2,6-difluoropyridin-3-yl)boronic acid (1.59 g , 10mmol) and Pd(PPh 3 ) 4 (0.12g, 0.1mmol) in the mixture. Stir, warm up to reflux, and react for 24h. The solution was distilled off under reduced pressure, and the crude product was separated by a column to obtain 1.23 g (54%) of the product. 1 H NMR (300MHz, CDCl 3,δ,ppm):(td,1H,J=8.1Hz,J=9.5Hz),8.54(d,1H,J=5.7Hz),7.40(m,1H),6.98(dd,1H,J=2.8 Hz, J=8.2Hz), 6.86(dd,1H, J=2.4Hz, J=5.7Hz), 3.94(s,3H).

[0086] Synthesis of I1:

[0087] IrCl 3 ·3H 2 O (1.58mmol, 0.55g) and 4-methoxy-2′,6′-difluoro-2,3′-bipyridine (3.24mmol, 0.72g) were dissolved in 15mL ethylene glycol monoethyl ether and 5mL water I...

Embodiment 2

[0090] Synthesis of compound I14

[0091] The reaction formula is as follows:

[0092]

[0093] Synthesis of 2-bromo-4-butoxypyridine:

[0094] Under an inert atmosphere, 20 mL of DMF and 1-bromobutane (5.00 g, 46.2 mmol) were added to a mixture of 2-bromo-4-hydroxypyridine (2.00 g, 11.6 mmol) and potassium carbonate (3.90 g, 23.1 mmol) middle. Stir, heat up to 60°C, and react for 24h. The solution was distilled off under reduced pressure, and the crude product was separated by a column to obtain 2.66 g (84%) of the product. 1 H NMR (300MHz, CDCl 3 )[ppm]:δ8.14(d,J=5.7Hz,1H),6.98(d,J=2.2Hz,1H),6.76(dd,J=2.3,5.7Hz,1H),3.99(t,J =6.5Hz,2H),1.72-1.82(m,2H),1.41-1.54(m,2H),0.98(t,J=7.4Hz,3H).

[0095] Synthesis of 4-butoxy-2′,6′-difluoro-2,3′-bipyridine:

[0096] Under an inert atmosphere, 10 mL of 2M aqueous potassium carbonate and 30 mL of tetrahydrofuran were added to 2-bromo-4-butoxypyridine (1.15 g, 5 mmol), (2,6-difluoropyridin-3-yl)boronic acid (0.79 g , 5mmol) an...

Embodiment 3

[0101] Synthesis of compound I13

[0102] The reaction formula is as follows:

[0103]

[0104] IrCl 3 ·3H 2 O (0.65g, 1.84mmol) and 4-butoxy-2′,6′-difluoro-2,3′-bipyridine (0.97g, 3.69mmol) were dissolved in 15mL ethylene glycol monoethyl ether and 5mL water In the mixed solvent, the gas was replaced three times, refluxed under the protection of argon for 24 hours, filtered, and the obtained solid was washed with water, washed with absolute ethanol, and dried to obtain a chlorine-bridged dimer.

[0105] The chlorine-bridged dimer obtained in the previous step, picolinic acid (0.23g, 1.84mmol), and anhydrous potassium carbonate (0.51g, 3.68mmol) were added to 20mL of chloroform solvent, the gas was replaced three times, and the reaction was refluxed under argon protection for 4h. , cooled to room temperature, filtered, and the resulting solid was washed repeatedly with dichloromethane to remove the black silver chloride solid. The obtained filtrate anhydrous Na 2 SO 4...

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Abstract

The invention provides a blue-ray metal complex shown as the formula I and an organic electroluminescent device containing the blue-ray metal complex. By means of introduction of an alkoxy group to a complexing N atom para-position, HOMO (highest occupied molecular orbital) energy level of the complex is effectively increased, and hole injection barrier is lowered. Compared with the prior art, the organic electroluminescent device based on the blue-ray metal complex has the advantages of low driving voltage and high power efficiency.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a blue-light metal complex and an organic electroluminescence device thereof. Background technique [0002] Organic Light-Emitting Diodes (OLEDs) have the characteristics of self-luminescence, high brightness, high efficiency, light and thin, wide viewing angle and easy processing, and have broad application prospects in the fields of information display and solid-state lighting. [0003] Organic electroluminescent materials can be divided into two categories: fluorescent and phosphorescent materials. Among them, phosphorescent metal complex materials have become a research hotspot in the field of electroluminescence because they can use singlet and triplet excitons at the same time, and the internal quantum efficiency can reach 100% in theory. Compared with red and green phosphorescent metal complexes, there are fewer types of blue light metal complexes. At...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 王利祥丁军桥夏德斌赵磊
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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