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

A phosphorescent material, metal iridium technology, applied in luminescent materials, electro-solid devices, organic chemistry, etc., can solve the problem of rarely reaching the color purity of deep red and dark green light, reduce the probability of self-quenching, stabilize The effect of 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 phosphor

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

Example Embodiment

[0058] Example 1

[0059] A red light organic electro-phosphorescent material metal iridium complex tris[1-phenoxy-4-phenylphthalazine-N,C 2 '] iridium, as shown in the following structural formula:

[0060]

[0061] The method for preparing the metal iridium complex of the red light organic electrophosphorescent material includes the following steps:

[0062] (1) Synthesis of cyclometal ligand 1-phenoxy-4-phenylphthalazine, the reaction formula is:

[0063]

[0064] The specific operation is:

[0065] Provide compound A represented by the following structural formula, namely 1-phenoxy-4-chlorophthalazine, and compound B1, namely phenylboronic acid:

[0066]

[0067] 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 DMF, and 15mL was added dropwise to a concentration of 1mol / L of potassium carbonate aqueous solution, heated to 100°C and stirred fo...

Example Embodiment

[0097] Example 2

[0098] A red light organic electrophosphorescent material metal iridium complex tris[1-phenoxy-4-(6'-methylphenyl)phthalazine-N,C 2 '] iridium, as shown in the following structural formula:

[0099]

[0100] The method for preparing the metal iridium complex of the red light organic electrophosphorescent material includes the following steps:

[0101] (1) Synthesis of cyclometal ligand 1-phenoxy-4-(2'-methylphenyl)phthalazine, the reaction formula is:

[0102]

[0103] The specific operation is:

[0104] Provide compound A represented by the following structural formula, namely 1-phenoxy-4-chlorophthalazine, and compound B2, namely 2-methylphenylboronic acid:

[0105]

[0106] 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 8mL was added dropwise to a concentration of 1mol / The L sodium carbonate aqueous solution ...

Example Embodiment

[0126] Example 3

[0127] A red light organic electrophosphorescent material metal iridium complex tris[1-phenoxy-4-(5'-methylphenyl)phthalazine-N,C 2 ′] Iridium, as shown in the following structural formula:

[0128]

[0129] The method for preparing the metal iridium complex of the red light organic electrophosphorescent material includes the following steps:

[0130] (1) Synthesis of cyclometal ligand 1-phenoxy-4-(3'-methylphenyl)phthalazine, the reaction formula is:

[0131]

[0132] The specific operation is:

[0133] Provide compound A represented by the following structural formula, namely 1-phenoxy-4-chlorophthalazine, and compound B3, namely 3-methylphenylboronic acid:

[0134]

[0135] Under the protection of nitrogen, 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 DMF, and 12mL was added dropwise. 1mol / L potassium carbonate aqueous solution, heated to 90℃ and stirred...

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Abstract

The present invention provides a red light organic electrophosphorescence material metal iridium coordination compound, which 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 ligand, the ring metal ligand and IrCl3.3H2O are subjected to a polymerization reaction in a 2-ethoxyethanol and water mixed solvent to obtain a chloro-bridge dimer, and the chloro-bridge dimer and the ring metal ligand 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-phenoxy-4-phenyl phthalazine or a derivative thereof is adopted as the ring metal ligand to synthesize to obtain the material, wherein 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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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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