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Red organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device

A technology of iridium metal complexes and phosphorescent materials, applied in the field of organic electroluminescence, can solve the problems of color purity and backwardness that are rarely achieved in dark red and dark green light, and achieve good energy transmission efficiency and high luminous efficiency , the effect of broad commercial development prospects

Inactive Publication Date: 2014-11-12
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally speaking, the development of blue phosphorescent materials always lags behind red light and green light. In terms of color purity alone, blue phosphorescent materials have rarely been able to achieve the same level as deep red light and deep green light. color purity

Method used

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  • Red organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device
  • Red organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device
  • Red organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1: A red-light organic electrophosphorescent material iridium metal complex bis[3-(4',6'-dimethylphenyl)cinnoline-N,C 2' ](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0065]

[0066] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0067] (1) Provide compound A and compound B1 represented by the following structural formula respectively:

[0068]

[0069] (2) Synthesis of cyclometal ligand 3-(2',4'-dimethylphenyl)cinnoline

[0070]

[0071] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline (compound A), 0.72g (4.8mmol) 2,4-dimethylphenylboronic acid (compound B1), 0.28g (0.24mmol) tetrakis (three Phenylphosphine)palladium was dissolved in 30mL of THF, and then 10mL of potassium carbonate aqueous solution with a mass fraction of 10% was added dropwise into the reaction system, and the mixture ...

Embodiment 2

[0092] Example 2: A red-light organic electrophosphorescent material iridium metal complex bis[3-(5',6'-dimethylphenyl)cinnoline-N,C 2' ](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0093]

[0094] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0095] (1) Provide compound A and compound B2 represented by the following structural formula respectively:

[0096]

[0097] (2) Synthesis of cyclometal ligand 3-(2',3'-dimethylphenyl)cinnoline

[0098]

[0099] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline, 0.6g (4.0mmol) 2,3-dimethylphenylboronic acid (compound B2), 0.23g (0.20mmol) tetrakis (triphenylphosphine) Palladium was dissolved in 25 mL of toluene, and 10 mL of potassium carbonate aqueous solution with a mass fraction of 10% was added dropwise to the reaction system, and the reaction system was heate...

Embodiment 3

[0119] Example 3: A red-light organic electrophosphorescent material iridium metal complex bis[3-(3',6'-dimethylphenyl)cinnoline-N,C 2' ](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0120]

[0121] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0122] (1) Provide compound A and compound B3 represented by the following structural formula respectively:

[0123]

[0124] (2) Synthesis of cyclometal ligand 3-(2',5'-dimethylphenyl)cinnoline

[0125]

[0126] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline, 0.9g (6.0mmol) 2,5-dimethylphenylboronic acid (compound B3), 0.11g (0.16mmol) dichlorobis (triphenyl Phosphine)palladium was dissolved in 40mL of toluene, and then 20mL of potassium carbonate aqueous solution with a mass fraction of 5% was added dropwise into the reaction system, and the reaction system wa...

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Abstract

The invention provides a red organic electrophosphorescent material iridium metal complex with the structure represented by formula (1). In the formula (1), each of R1 and R2 is a methyl group. The red organic electrophosphorescent material iridium metal complex is prepared through the following steps: carrying out a Suzuki coupling reaction on an iridium metal complex to prepare a cyclomedtalating ligand, carrying out a polymerization reaction on the cyclomedtalating ligand and chromium trichloride hexahydrate in a 2-ethoxyethanol and water mixed solvent to obtain a chlorendic dimer, and carrying out a complex reaction on the chlorendic dimer and an auxiliary ligand 2,2,6,6-tetramethyl-3,5-heptanedione to obtain the red organic electrophosphorescent material iridium metal complex represented by formula (1). The above material has good energy transmission efficiency and appropriate red light emitting wavelength, and can be widely used to make red or white phosphorescent electroluminescent devices in order to reduce the power consumption of the devices, improve the performances of the devices and prolong the life of the devices.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and in particular relates to a red-light organic electroluminescence material iridium metal complex, a preparation method thereof, and an organic electroluminescence device. Background technique [0002] An organic electroluminescent device (OLED) is an energy conversion device that uses organic materials as light-emitting materials and can convert applied electrical energy into light energy. It has outstanding performances such as ultra-thin, self-luminous, fast response, low power consumption, etc., and has extremely broad application prospects in display, lighting and other fields. [0003] Organic electroluminescent materials can be divided into two types: fluorescent materials and phosphorescent materials. In fluorescent electroluminescent devices, due to the limitation of spin prohibition, the excited singlet state that produces fluorescence only accounts for 25% of the total exc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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