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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 low luminous efficiency, high luminescent color purity, poor stability of light-emitting devices, and reduce self-quenching phenomenon. , the effect of high luminous efficiency and broad commercial development prospects

Inactive Publication Date: 2014-08-06
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current red phosphorescent materials are still difficult to achieve such a high luminous color purity, resulting in low luminous efficiency, poor stability and short lifespan of organic electroluminescent devices.

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

[0058] A red-light organic electrophosphorescent material metal iridium complex tris[1-methyl-4-(4',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methyl-4-(2',4'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0059]

[0060] Wherein, the ring metal ligand is:

[0061]

[0062] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0063] (1) Provide compound A and compound B1 represented by the following structural formula respectively:

[0064]

[0065] (2) Synthesis of cyclometal ligand 1-methyl-4-(2',4'-dimethylphenyl)phthalazine

[0066]

[0067] Under nitrogen protection, 15mL of dimethylformamide (DMF) solution was added to the reactor, and then 0.72g (4.0mmol) of compound A (1-methyl-4-chlorophthalazine), 0.72g (4.8mmol ) Compound B1 (2,4-dimethylphenylboronic acid) and 0.23g (0.20mmol) tetrakis(triphe...

Embodiment 2

[0089] A red-light organic electrophosphorescent material metal iridium complex tris[1-methyl-4-(5',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methyl-4-(2',3'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0090]

[0091] Wherein, the ring metal ligand is:

[0092]

[0093] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0094] (1) Provide compound A and compound B2 represented by the following structural formula respectively:

[0095]

[0096] (2) Synthesis of cyclometal ligand 1-methyl-4-(2',3'-dimethylphenyl)phthalazine

[0097]

[0098] Under nitrogen protection, 15mL of dimethylformamide (DMF) solution was added to the reactor, and then 0.72g (4.0mmol) of compound A (1-methyl-4-chlorophthalazine), 0.6g (4.0mmol ) Compound B2 (2,3-dimethylphenylboronic acid) and 0.28g (0.24mmol) tetrakis(triphen...

Embodiment 3

[0119] A red-light organic electrophosphorescent material metal iridium complex tris[1-methyl-4-(3',6'-dimethylphenyl)phthalazine-N,C 2 ']iridium, with 1-methyl-4-(2',5'-dimethylphenyl)phthalazine as the ring metal ligand, the structural formula is as follows:

[0120]

[0121] Wherein, the ring metal ligand is

[0122]

[0123] The preparation method of the metal iridium complex of the above-mentioned red light organic electrophosphorescent material comprises the following steps:

[0124] (1) Provide compound A and compound B3 represented by the following structural formula respectively:

[0125]

[0126] (2) Synthesis of cyclometal ligand 1-methyl-4-(2',5'-dimethylphenyl)phthalazine

[0127]

[0128] Under nitrogen protection, 15mL of toluene was added to the reactor, and then 0.72g (4.0mmol) of compound A (1-methyl-4-chlorophthalazine), 1.20g (8mmol) of compound B3 (2,5-di Toluene boronic acid) and 0.28g (0.24mmol) tetrakis (triphenylphosphine) palladium are ...

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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 a preparation method for the red light organic electrophosphorescence material metal iridium coordination compound. The method comprises that: a Suzuki coupling reaction is performed to prepare a ring metal ligand, the ring metal ligand and iridium trichloride trihydrate are subjected to a polymerization reaction 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 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-methyl-4-phenyl phthalazine is adopted as the ring metal ligand main structure, and the two methyl groups are introduced on the benzene ring of the ring metal ligand to achieve adjustment on the material luminescence color so as to obtain the satisfied red light emission wavelength, increase the luminescence color purity of the red phosphorescence material, and increase the luminescence efficiency and the stability of the organic electroluminescent device.

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): C09K11/06C07F15/00H01L51/54
Inventor 周明杰王平张娟娟梁禄生
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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