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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 problems of limited carrier transport, low luminous efficiency, poor stability, etc., to increase solubility and luminous efficiency. High and convenient synthesis and processing 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

At present, the main ligands used to obtain high-efficiency red light in iridium complexes are mainly benzothiophene and quinoline, but these ligands are not only difficult to synthesize, but also limit the transport of carriers. Organic electroluminescent devices have low luminous efficiency, poor stability and short life

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

[0059] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-phenylphthalazine-N,C 2 '](acetylacetonate) iridium, with 1-methoxy-4-phenylphthalazine as ring metal ligand, as shown in the following structural formula:

[0060]

[0061] Wherein, the R group is a hydrogen atom (not shown in the structural formula), and the structural formula of the ring metal ligand is

[0062]

[0063] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0064] (1) Provide compound A and compound B1 represented by the following structural formula respectively:

[0065]

[0066] (2) Synthesis of cyclometal ligand 1-methoxy-4-phenylphthalazine

[0067] Under the protection of nitrogen, 0.78g (4.0mmol) 1-methoxy-4-chlorophthalazine (ie compound A), 0.59g (4.8mmol) phenylboronic acid (ie compound B1) and 0.23g (0.20mmol) four (Triphenylphosphine) pall...

Embodiment 2

[0090] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(6'-methylphenyl)phthalazine-N,C 2 '](acetylacetonate) iridium, with 1-methoxy-4-(2'-methylphenyl)phthalazine as the ring metal ligand, as shown in the following structural formula:

[0091]

[0092] In the formula, the R group is a methyl group, and the structural formula of the ring metal ligand is

[0093]

[0094] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material 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 1-methoxy-4-(2'-methylphenyl)phthalazine

[0098] Under nitrogen protection, 0.78g (4.0mmol) 1-methoxy-4-chlorophthalazine (ie compound A), 1.09g (8mmol) 2-methylphenylboronic acid (ie compound B2) and 0.23g (0.20 mmol) tetrakis (triphenylphosph...

Embodiment 3

[0120] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(5'-methylphenyl)phthalazine-N,C 2 '](acetylacetonate) iridium, with 1-methoxy-4-(3'-methylphenyl)phthalazine as the ring metal ligand, as shown in the following structural formula:

[0121]

[0122] In the formula, the R group is a methyl group, and the structural formula of the ring metal ligand is

[0123]

[0124] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0125] (1) Provide compound A and compound B3 represented by the following structural formula respectively:

[0126]

[0127] (2) Synthesis of cyclometal ligand 1-methoxy-4-(3'-methylphenyl)phthalazine

[0128] Under nitrogen protection, 0.78g (4.0mmol) 1-methoxy-4-chlorophthalazine (ie compound A), 0.55g (4mmol) 3-methylphenylboronic acid (ie compound B3) and 0.14g (0.20 mmol) dichlorobis(triphenylphos...

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Abstract

The present invention discloses a red light organic electrophosphorescence material metal iridium coordination compound having a structural formula represented by a formula (P), wherein R is hydrogen atom or methyl. The present invention further provides a preparation method for the coordination compound, and an organic electroluminescent device containing the coordination compound. According to the present invention, 1-methoxy-4-phenyl phthalazine having large plane rigidity is adopted as the main ligand so as to balance charge transmission of the organic electroluminescent device, and acetylacetone is added to the ring metal ligand as the heterotypic auxiliary ligand so as to reduce the synthesis difficulty of the metal iridium coordination compound, and easily synthesize and purify the product.

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 electroluminescent device (OLED) is a current-mode semiconductor light-emitting device based on organic light-emitting materials. Due to its high luminous efficiency, low driving voltage, wide viewing angle, wide range of luminous color options, simple manufacturing process, and easy realization of full-color and flexible display, OLED has attracted more and more attention in the field of lighting and flat panel display. . [0003] OLED light-emitting materials can be divided into two types: fluorescent materials and phosphorescent materials. Due to the limitation of spin statistics theory, the theoretical internal quantum efficiency limit of fluorescent materials is only ...

Claims

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Application Information

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