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

A phosphorescent material and metal iridium technology, applied in luminescent materials, electrical solid devices, organic chemistry, etc., can solve the problems of low luminous efficiency, low luminous color purity, and poor stability of light-emitting devices, and achieve broad commercial development prospects , high luminous efficiency, and the effect of improving synthesis efficiency

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 existing iridium complexes are mainly benzothiophene and quinoline. Although such iridium complexes can emit red light to a certain extent...

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-(4',6'-dimethylphenyl)phthalazine-N,C 2 '](acetylacetonate)iridium, with 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0060]

[0061] Wherein, 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] Among them, compound A is 1-methoxy-4-chlorophthalazine, and B1 is 2,4-dimethylphenylboronic acid.

[0067] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine

[0068]

[0069] Under nitrogen protection, 0.78g (4.0mmol) 1-methoxy-4-chlorophthalazine, 0.72g (4.8mmol) 2,4-dimethylphenylbo...

Embodiment 2

[0091] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(5',6'-dimethylphenyl)phthalazine-N,C 2 '](acetylacetonate)iridium, with 1-methoxy-4-(2',3'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0092]

[0093] Wherein, the structural formula of the ring metal ligand is:

[0094]

[0095] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0096] (1) Provide compound A and compound B2 represented by the following structural formula respectively:

[0097]

[0098] Among them, compound A is 1-methoxy-4-chlorophthalazine, and B2 is 2,3-dimethylphenylboronic acid.

[0099] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',3'-dimethylphenyl)phthalazine

[0100]

[0101] Under nitrogen protection, 0.78g (4.0mmol) 1-methoxy-4-chlorophthalazine, 0.60g (4mmol) 2,3-methylphenylboroni...

Embodiment 3

[0122] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(3',6'-dimethylphenyl)phthalazine-N,C 2 '](acetylacetonate)iridium, with 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0123]

[0124] Wherein, the structural formula of the ring metal ligand is:

[0125]

[0126] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0127] (1) Provide compound A and compound B3 represented by the following structural formula respectively:

[0128]

[0129] Among them, compound A is 1-methoxy-4-chlorophthalazine, and B3 is 2,5-dimethylphenylboronic acid.

[0130] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',5'-diylphenyl)phthalazine

[0131]

[0132] Under nitrogen protection, 0.78g (4.0mmol) of 1-methoxy-4-chlorophthalazine, 1.20g (8mmol) of 2,5-dimethylphenylbo...

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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 methyl. The present invention further provides an organic electroluminescent device containing the metal iridium coordination compound. According to the present invention, 1-methoxy-4-phenyl phthalazine is adopted as the ring metal ligand main structure, and acetylacetone is adopted as the heterotypic auxiliary ligand to synthesize the heterotypic coordination type metal iridium coordination compound having high red luminescence color purity so as to reduce the synthesis difficulty and the purification difficulty of the metal iridium coordination compound; and the chemical modification method that the two methyl groups are introduced on different C sites of the benzene ring in the ring metal ligand is adopted to achieve adjustment on the material luminescence color so as to make the metal iridium coordination compound phosphorescence emission spectrum produce red shift.

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 the spin statistics theory, the theoretical internal quantum efficiency limit of fluorescent materials is o...

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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