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Red light organic electrophosphorescence material metal iridium coordination compound and preparation method thereof, and organic electroluminescent device

A technology of phosphorescent materials and metal iridium, which is applied in the fields of luminescent materials, electric solid devices, organic chemistry, etc., can solve problems such as the color purity of dark red light and dark green light that are rarely achieved, and achieve low processing cost and easy preparation process Controlled, high luminous efficiency effect

Inactive Publication Date: 2014-08-06
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

[0005] In order to realize full-color display based on OLED devices, it is generally necessary to obtain red, green and blue materials with excellent performance at the same time. Generally speaking, the development of blue phosphorescent materials always lags behind red and green phosphorescent materials. In terms of this indicator, the luminescence of blue phosphorescent materials has so far rarely achieved the color purity of deep red and deep green light.

Method used

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  • Red light organic electrophosphorescence material metal iridium coordination compound and preparation method thereof, and organic electroluminescent device
  • Red light organic electrophosphorescence material metal iridium coordination compound and preparation method thereof, and organic electroluminescent device
  • Red light organic electrophosphorescence material metal iridium coordination compound and preparation method thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] A red-light organic electrophosphorescent material metal iridium complex bis[1-methyl-4-phenylphthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0061]

[0062] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0063] (1) Synthesis of cyclometallic main ligand 1-methyl-4-phenylphthalazine, the reaction formula is:

[0064]

[0065] The specific operation is:

[0066] Compound A represented by the following structural formula, i.e. 1-methyl-4-chlorophthalazine, and compound B1, i.e. phenylboronic acid are provided respectively:

[0067]

[0068] Under the protection of nitrogen, 0.72g (4.0mmol) of compound A, 0.59g (4.8mmol) of compound B1 and 0.23g (0.20mmol) of tetrakis (triphenylphosphine) palladium were mixed and dissolved in 15mL of DMF, and the concentration of 1mol was added dropwise ...

Embodiment 2

[0099] A red-light organic electrophosphorescent material metal iridium complex bis[1-methyl-4-(6'-methylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0100]

[0101] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0102] (1) Synthesis of cyclometallic main ligand 1-methyl-4-(2'-methylphenyl)phthalazine, the reaction formula is:

[0103]

[0104] The specific operation is:

[0105] Compound A represented by the following structural formula, i.e. 1-methyl-4-chlorophthalazine, and compound B2, i.e. 2-methylphenylboronic acid are provided respectively:

[0106]

[0107] Under nitrogen protection, 0.72g (4.0mmol) of compound A, 0.68g (5mmol) of compound B2 and 0.11g (0.16mmol) of dichlorobis(triphenylphosphine)palladium were mixed and dissolved in 15mL of toluene, and the concentration o...

Embodiment 3

[0128] A red-light organic electrophosphorescent material metal iridium complex bis[1-methyl-4-(5'-methylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0129]

[0130] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0131] (1) Synthesis of cyclometallic main ligand 1-methyl-4-(3'-methylphenyl)phthalazine, the reaction formula is:

[0132]

[0133] The specific operation is:

[0134] Compound A represented by the following structural formula, i.e. 1-methyl-4-chlorophthalazine, and compound B3, i.e. 3-methylphenylboronic acid are provided respectively:

[0135]

[0136]Under the protection of nitrogen, mix 0.72g (4.0mmol) compound A, 0.65g (4.8mmol) compound B3 and 0.08g (0.12mmol) dichlorobis(triphenylphosphine)palladium in 20mL DMF, and add dropwise 8mL concentration 1 mol / L potassiu...

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Abstract

The present invention provides a red light organic electrophosphorescence material metal iridium coordination compound, which adopts 1-methyl-4-phenyl phthalazine or a derivative thereof as a ring metal main ligand, adopts 2,2,6,6-tetramethyl-3,5-heptanedione as an auxiliary ligand, and has a structure formula represented by a formula (1), wherein R is hydrogen or methyl. The preparation method comprises that: a Suzuki coupling reaction is performed to prepare a ring metal main ligand, the ring metal main ligand and IrCl3.3H2O are subjected to polymerization in a 2-ethoxyethanol and water mixed solvent to obtain a chloro-bridge dimer, and the chloro-bridge dimer and acetylacetone are subjected to a ligand exchange reaction to obtain the red light organic electrophosphorescence material metal iridium coordination compound. According to the present invention, 1-methyl-4-phenyl phthalazine is adopted as the ring metal main ligand, 2,2,6,6-tetramethyl-3,5-heptanedione is adopted as the auxiliary ligand, and the emission wavelength can be adjusted so as to obtain the red light near the standard red color; and the organic electroluminescent device prepared from the material can emit high purity red light, the luminescence efficiency is high, and the preparation method is simple and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and specifically relates to a metal iridium complex of a red light organic electroluminescence material, a preparation method thereof, and an organic electroluminescence device. Background technique [0002] Organic electroluminescence refers to a light-emitting phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. Organic electroluminescent devices (OLEDs) use this type of organic material as a light-emitting material to convert electrical energy into light energy. energy conversion device. Early organic electroluminescent devices had defects such as high driving voltage and low luminous efficiency, which made the research stagnant. To 1987, people such as Tang of American Kodak Company invented 8-hydroxyquinoline aluminum (Alq 3 ) is a luminescent material, and a uniform and dense high-quality thin film is m...

Claims

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Application Information

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