Metal complex and application thereof in organic electroluminescent device

A technology of complexes and metal iridium, applied in the direction of electric solid devices, electrical components, luminescent materials, etc., can solve the problems of efficiency roll-off, etc., and achieve the effects of short luminous life, high luminous efficiency, and high luminous efficiency

Active Publication Date: 2014-03-26
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The purpose of the present invention is to propose a class of near-infrared light-emitting materials with pure light color and considerable luminous efficiency, which can be applied to organic light-emitting devices. By introducing large π-conjugated structures and steric hindrance groups, the collision between dye triplet excitons can be reduced. , to overcome the problem of device efficiency roll-off at high current density

Method used

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  • Metal complex and application thereof in organic electroluminescent device
  • Metal complex and application thereof in organic electroluminescent device
  • Metal complex and application thereof in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Compound C1-1

[0056] Reaction formula:

[0057]

[0058] process:

[0059] IrCl 3 ·xH 2 O (58%Ir) and 2.2 times the chemical equivalent of the ligand were dissolved in a mixed solvent of ethylene glycol methyl ether and deionized water (v / v=3 / 1). Stir under reflux at 100° C. for 24 hours under an Ar atmosphere. Cool to room temperature and filter, wash the filter cake with deionized water until neutral, then rinse the filter cake with 10mL ethanol and 200mL diethyl ether in sequence. Finally, the filter cake was dissolved with dichloromethane, the filtrate was collected, the solvent was removed by rotary evaporation, and vacuum-dried at 70°C for 5 hours to obtain an ocher solid with a yield of 89%, which was directly put into the next reaction without further purification. 1 H-NMR (CDCl 3 ,300MHz,δ[ppm]):2.81(s,3H),5.66~5.69(d,1H),6.13~6.18(t,1H),6.74~6.79(t,1H),7.51~7.61(m,2H ),7.74~7.78(t,1H),7.95~7.98(d,1H),8.06(s,1H),8.86(s,1H).ESI-MS[m / z]:1...

Embodiment 2

[0063] Example 2: Compound C1-2

[0064]

[0065] The acetylacetone in Example 1 was replaced by picolinic acid, and the complex was obtained by a similar method with a yield of 45%.

[0066] 1 H-NMR (CDCl 3 ,600MHz,δ[ppm]):2.68(s,6H),7.41(t,2H),7.51(m,4H),7.65(m,4H),7.79(d,2H),7.88(t,1H) ,7.98(t,1H),8.06(s,4H),8.16(d,4H),8.29(d,1H),9.01(d,1H).

[0067] ESI-MS[m / z]:854[M+H] + .Elemental analysis (C44H30N5IrO2): Anal. Calcd.: C, 61.96; H, 3.55; N, 8.21. Found: C, 62.02; H, 3.60; N, 8.19.

Embodiment 3

[0068] Example 3: Compound C1-3

[0069]

[0070]0.76g (0.5mmol) of dichloro-bridged intermediate, 0.30g (1.1mmol) of the main ligand and 0.28g (1.1mmol) of silver trifluoromethanesulfonate were dissolved in 50mL of ethylene glycol monomethyl ether. The reaction system was protected by argon, shielded from light, and stirred at reflux for 24 hours. After cooling to room temperature, filter and rinse with a small amount of ethylene glycol monomethyl ether. Then elute with dichloromethane, collect the filtrate, distill off the solvent, separate by column chromatography, and collect the black product band. After concentration, it was recrystallized with dichloromethane / ether to obtain a black solid with a yield of 30%.

[0071] 1 H-NMR (CDCl 3 ,300MHz,δ[ppm]):2.81(s,3H),5.66~5.69(d,1H),6.13~6.18(t,1H),6.74~6.79(t,1H),7.51~7.61(m,2H ),7.74~7.78(t,1H),7.95~7.98(d,1H),8.06(s,1H),8.86(s,1H).

[0072] ESI-MS[m / z]:1001[M+H] + .Elemental analysis (C57H39N6Ir): Anal. Calcd.: C,...

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Abstract

The invention relates to a novel metal complex and application thereof in an organic luminescent device. The structural general formula of the metal iridium complex for near infrared luminescence is LnIrX(3-n), wherein X is selected from acetylacetone, dibenzoylmethane, dipivaloylmethane or picolinic acid; n is selected from 1, 2 or 3; L is selected from the following structural formula L1, L2 or L3; R1-R9 are independently selected from H, C1-10 alkyl, C1-10 alkoxy, C1-10 alkylamino, carbazolyl, F, trifluoromethyl and C5-18 aryl respectively; and Ar represents C5-18 aryl and C5-18 heterocyclic aryl. The metal complex has the advantages of short luminescence life and high luminescence efficiency; and an organic luminescent device prepared from the luminescent material has the characteristic of high luminescence efficiency under high current density. The structural formula L1, the structural formula L2 and the structural formula L3 are shown in the specification.

Description

technical field [0001] The invention relates to a novel metal complex and its application in organic light-emitting devices. It specifically relates to a kind of near-infrared luminous transition metal complexes and an organic light-emitting device containing such materials, and belongs to the technical field of organic light-emitting displays. Background technique [0002] The part of the spectrum with wavelengths ranging from 700 to 1500 nanometers is called the near-infrared region. Nearly 50% of the solar energy falls on this area; near-infrared light sources of 1.31 and 1.55 microns can minimize the loss of optical fibers; in addition, the main components of biological tissue, hemoglobin and water, have the weakest absorption of light in the wavelength range of 650 to 900nm . Therefore, the development of near-infrared materials and technologies plays an important role in promoting many fields such as energy, communication, biological imaging, sensing and display. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 乔娟陶然邱勇
Owner TSINGHUA UNIV
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