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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 of organic electroluminescent devices, limitation of carrier transport efficiency, low purity of red light emission, etc., to achieve Reduce self-quenching phenomenon, facilitate synthesis and extraction, and improve luminous 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, and their defects are: 1) Most of the emission spectrum is located in the orange and yellow regions, and the purity of red emission is low ; 2) Difficult to synthesize and low extraction rate; 3) Limited carrier transfer efficiency
The resulting organic electroluminescent device has 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

[0057] A red-light organic electrophosphorescent material metal iridium complex tris[1-methoxy-4-(4',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0058]

[0059] Wherein, the structural formula of the ring metal ligand is:

[0060]

[0061] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0062] (1) Provide compound A and compound B1 represented by the following structural formula respectively:

[0063] A: B1:

[0064] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine

[0065]

[0066] Under nitrogen protection, 15mL of dimethylformamide (DMF) solution was added to the reactor, and then 0.78g (4.0mmol) of compound A (1-methoxy-4-chlorophthalazine), 0.72g (4.8 mmol) Compound B1 (2,4-dimethylphenylboronic aci...

Embodiment 2

[0088] A red-light organic electrophosphorescent material metal iridium complex tris[1-methoxy-4-(5',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methoxy-4-(2',3'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0089]

[0090] Wherein, the structural formula of the ring metal ligand is:

[0091]

[0092] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0093] (1) Provide compound A and compound B2 represented by the following structural formula respectively:

[0094] A: B2:

[0095] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',3'-dimethylphenyl)phthalazine

[0096]

[0097] Under nitrogen protection, 15mL of dimethylformamide (DMF) solution was added to the reactor, and then 0.78g (4.0mmol) of compound A (1-methoxy-4-chlorophthalazine), 0.6g (4mmol ) Compound B2 (2,3-dimethylphenylboronic acid) ...

Embodiment 3

[0118] A red-light organic electrophosphorescent material metal iridium complex tris[1-methoxy-4-(3',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methoxy-4-(2',5'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0119]

[0120] Wherein, the structural formula of the ring metal ligand is:

[0121]

[0122] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0123] (1) Provide compound A and compound B3 represented by the following structural formula respectively:

[0124] A: B3:

[0125] (2) Synthesis of cyclometal ligand 1-methoxy-4-(2',5'-diylphenyl)phthalazine

[0126]

[0127] Under nitrogen protection, 15mL of dimethylformamide (DMF) solution was added to the reactor, and then 0.78g (4.0mmol) of compound A (1-methoxy-4-chlorophthalazine), 1.20g (8mmol ) Compound B3 (2,5-dimethylphenylboronic acid) and...

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Abstract

The present invention discloses a red light organic electrophosphorescence material metal iridium coordination compound, which has a structure formula represented by a formula (P), wherein R is methyl. The preparation method comprises that: a Suzuki coupling reaction is performed to obtain a ring metal ligand, the ring metal ligand and iridium trichloride trihydrate 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 coordination reaction to obtain the red light organic electrophosphorescence material metal iridium coordination compound. 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 having large plane rigidity is adopted as the ring metal main ligand to balance carrier transmission and increase coordination compound solubility so as to easily process, and the two methyl groups are introduced on the benzene ring of the ring metal main ligand to make the luminescent material luminescent spectrum produce red shift so as to increase red light luminescence purity.

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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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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