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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 , The effect that the preparation process is easy to control

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

[0071] Example 1: A red-light organic electrophosphorescent material iridium metal complex bis[3-(4',6'-dimethylphenyl)-4-phenylcinnoline-N,C 2 '] (acetylacetonate) iridium, as shown in the following structural formula:

[0072]

[0073] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0074] (1) Provide compound A and Grignard reagent B1 represented by the following structural formula respectively:

[0075]

[0076] (2) Synthesis of 1-phenyl-1-(2′-aminophenyl)-2-(2′,4′-dimethylphenyl)ethanol

[0077]

[0078] Under the protection of nitrogen, 1.97g (10mmol) 2-aminobenzophenone (compound A) was dissolved in 60mL of anhydrous ether, and 1.06g (43.5mmol) magnesium particles, 6.73g (43.5mmol) 2 , Grignard reagent B1 solution prepared by 4-dimethylbenzyl chloride (compound D1) and 30 mL of anhydrous ether; after the dropwise addition, reflux for 45 min, add excess methan...

Embodiment 2

[0108] Example 2: A red-light organic electrophosphorescent material iridium metal complex bis[3-(5′,6′-dimethylphenyl)-4-phenylcinnoline-N,C 2 '] (acetylacetonate) iridium, as shown in the following structural formula:

[0109]

[0110] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0111] (1) Provide compound A and Grignard reagent B2 represented by the following structural formula respectively:

[0112]

[0113] (2) Synthesis of 1-phenyl-1-(2′-aminophenyl)-2-(2′,3′-dimethylphenyl)ethanol

[0114]

[0115] Under nitrogen protection, 1.97g (10mmol) of 2-aminobenzophenone was dissolved in 50mL of anhydrous ether, and 1.16g (47.85mmol) of magnesium particles, 6.73g (43.5mmol) of 2,3-bis Grignard reagent B2 solution prepared by methylbenzyl chloride and 30mL anhydrous ether; reflux for 40min after the dropwise addition, add excess methanol and ammonium nitrate to que...

Embodiment 3

[0144] Example 3: A red-light organic electrophosphorescent material iridium metal complex bis[3-(3′,6′-dimethylphenyl)-4-phenylcinnoline-N,C 2 '] (acetylacetonate) iridium, as shown in the following structural formula:

[0145]

[0146] The preparation method of the above-mentioned red light organic electrophosphorescent material iridium metal complex comprises the following steps:

[0147] (1) Provide compound A and Grignard reagent B3 represented by the following structural formula respectively:

[0148]

[0149] (2) Synthesis of 1-phenyl-1-(2′-aminophenyl)-2-(2′,5′-dimethylphenyl)ethanol

[0150]

[0151] Under nitrogen protection, 1.97g (10mmol) of 2-aminobenzophenone was dissolved in 40mL of anhydrous ether, and 1.10g (45.8mmol) of magnesium particles, 6.73g (43.5mmol) of 2,5-bis Grignard reagent B3 solution prepared by methyl benzyl chloride and 30 mL of anhydrous ether; reflux for 45 minutes after the dropwise addition, add excess methanol and ammonium nitra...

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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 Grignard reaction on an iridium metal complex to prepare a compound C, carrying out dehydration cyclization on the compound C to obtain 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 acetylacetone 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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IPC IPC(8): C07F15/00C09K11/06H01L51/54
Inventor 周明杰王平张娟娟张振华
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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