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Red light-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device

A technology of phosphorescent materials and metal iridium, which is applied in the direction 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, so as to reduce the probability of self-quenching and stabilize Good performance and low processing cost

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-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device
  • Red light-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device
  • Red light-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] A red-light organic electrophosphorescent material metal iridium complex bis[1-phenoxy-4-phenylphthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0059]

[0060] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0061] (1) Synthesis of cyclometallic main ligand 1-phenoxy-4-phenylphthalazine, the reaction formula is:

[0062]

[0063] The specific operation is:

[0064] Compound A represented by the following structural formula, i.e. 1-phenoxy-4-chlorophthalazine, and compound B1, i.e. phenylboronic acid are provided respectively:

[0065]

[0066] Under the protection of nitrogen, 1.03g (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 dropwi...

Embodiment 2

[0097] A red-light organic electrophosphorescent material metal iridium complex bis[1-phenoxy-4-(6'-methylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0098]

[0099] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0100] (1) Synthesis of cyclometallic main ligand 1-phenoxy-4-(2'-methylphenyl)phthalazine, the reaction formula is:

[0101]

[0102] The specific operation is:

[0103] Compound A represented by the following structural formula, i.e. 1-phenoxy-4-chlorophthalazine, and compound B2, i.e. 2-methylphenylboronic acid are provided respectively:

[0104]

[0105] Under the protection of nitrogen, 1.03g (4.0mmol) of compound A, 0.81g (6mmol) of compound B2 and 0.18g (0.16mmol) of tetrakis (triphenylphosphine) palladium were mixed and dissolved in 12mL of toluene, and the concen...

Embodiment 3

[0126] A red-light organic electrophosphorescent material metal iridium complex bis[1-phenoxy-4-(5'-methylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, as shown in the following structural formula:

[0127]

[0128] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0129] (1) Synthesis of cyclometallic main ligand 1-phenoxy-4-(3'-methylphenyl)phthalazine, the reaction formula is:

[0130]

[0131] The specific operation is:

[0132] Compound A represented by the following structural formula, i.e. 1-phenoxy-4-chlorophthalazine, and compound B3, i.e. 3-methylphenylboronic acid are provided respectively:

[0133]

[0134] Under nitrogen protection, 1.03g (4.0mmol) of compound A, 0.81g (6mmol) of compound B3 and 0.09g (0.12mmol) of dichlorobis(triphenylphosphine)palladium were mixed and dissolved in 20mL of DMF, and 12mL of 1mol / L pota...

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Abstract

The invention discloses a red light-emitting organic electrophosphorescent material iridium complex having a structure shown in the formula (1), and in the formula, R represents hydrogen or methyl. A preparation method of the red light-emitting organic electrophosphorescent material iridium complex comprises the following steps that a ring metal main ligand is prepared by a Suzuki coupling reaction, the ring metal main ligand and IrCl3.3H2O undergo a polymerization reaction in a 2-ethoxyethanol-water mixed solvent to produce a chlorine-bridged bipolymer, and the chlorine-bridged bipolymer and 2,2,6,6-tetramethyl-3,5-heptadione undergo a ligand exchange reaction to produce the red light-emitting organic electrophosphorescent material iridium complex. The red light-emitting organic electrophosphorescent material iridium complex is prepared by synthesis of 1-phenoxy-4-phenylphthalazine or its derivative as the ring metal main ligand and 2,2,6,6-tetramethyl-3,5-heptadione as an assistant ligand, and can adjust luminescence wavelength and produce approximately-standard red light. An organic electroluminescent device prepared from the red light-emitting organic electrophosphorescent material iridium complex can emit high-purity red light and has high luminescence efficiency. The preparation method has simple processes 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 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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