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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, which can solve the problems of backwardness and rarely achieve the color purity of dark red and dark green light, and achieve high luminous efficiency and good energy transmission efficiency , good stability

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-phenylcinnoline-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-phenylcinnoline

[0070]

[0071] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline (compound A), 0.59g (4.8mmol) phenylboronic acid (compound B1), 0.28g (0.24mmol) tetrakis (triphenylphosphine) palladium was dissolved in In 30mL of THF, 10mL of potassium carbonate aqueous solution with a mass fraction of 10% was added dropwise to the reaction system, heated to reflux temperature and stirred for 18h. After the reaction ...

Embodiment 2

[0092] Example 2: A red-light organic electrophosphorescent material iridium metal complex bis[3-(6'-methoxyphenyl)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'-methoxyphenyl)cinnoline

[0098]

[0099] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline, 0.61g (4.0mmol) 2-methoxyphenylboronic acid, 0.23g (0.20mmol) tetrakis (triphenylphosphine) palladium were dissolved in 25mL of toluene , 10 mL of 10% potassium carbonate aqueous solution was added dropwise to the reaction system, heated to reflux temperature and stirred for 10 h. After the reaction was completed...

Embodiment 3

[0119] Example 3: A red-light organic electrophosphorescent material iridium metal complex bis[3-(5'-ethoxyphenyl)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-(3'-ethoxyphenyl)cinnoline

[0125]

[0126] Under nitrogen protection, 0.83g (4.0mmol) 3-bromocinnoline, 0.80g (4.8mmol) 2-ethoxyphenylboronic acid, 0.28g (0.24mmol) dichlorobis (triphenylphosphine) palladium were dissolved in 40mL In THF, 20 mL of an aqueous solution of sodium carbonate with a mass fraction of 5% was added dropwise to the reaction system, and the reaction system was heated to reflux temperature and st...

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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), R is a hydrogen atom or a C1-C4 straight chain or alkoxy 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
CPCY02B20/00
Inventor 周明杰王平张娟娟冯小明
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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