Red light-emitting organic electrophosphorescent material iridium complex, its preparation method 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 affecting the luminous efficiency, low luminous efficiency and small steric hindrance of iridium complex phosphorescent materials, and reduce self-quenching. The effect of eliminating the phenomenon of extinction, simplifying the synthesis process, and increasing the solubility

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. The existence of conjugated ligands makes iridium complexes have good red light emission characteristics, but due to the small steric hindrance , the metal atoms in these complexes are easy to interact, resulting in self-quenching of triplet excitons, which seriously affects the luminous efficiency of iridium complex phosphorescent materials, and the luminous efficiency of organic electroluminescent devices prepared as luminescent materials Low, poor stability, short life

Method used

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  • Red light-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device
  • Red light-emitting organic electrophosphorescent material iridium complex, its preparation method and organic electroluminescent device
  • Red light-emitting organic electrophosphorescent material iridium complex, its preparation method 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 '](2,2,6,6-tetramethyl-3,5-heptanedione)iridium, with 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine It is a ring metal ligand, and its 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....

Embodiment 2

[0091] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(5',6'-dimethylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione)iridium, with 1-methoxy-4-(2',3'-dimethylphenyl)phthalazine It is a ring metal ligand, and its 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 (4m...

Embodiment 3

[0122] A red-light organic electrophosphorescent material metal iridium complex bis[1-methoxy-4-(3',6'-dimethylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione)iridium, with 1-methoxy-4-(2',4'-dimethylphenyl)phthalazine It is a ring metal ligand, and its 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 (8mm...

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Abstract

The invention discloses a red light-emitting organic electrophosphorescent material iridium complex having a structure shown in the formula (P), and in the formula, R represents methyl. The preparation method comprises the following steps that a ring metal ligand is prepared by a Suzuki coupling reaction, the ring metal ligand and an iridium trichloride trihydrate undergo a polymerization reaction in a 2-ethoxyethanol-water mixed solvent to produce a chlorine-bridged biopolymer, and the chlorine-bridged biopolymer and 2,2,6,6-tetramethyl-3,5-heptanedione undergo a coordination reaction to produce the red light-emitting organic electrophosphorescent material iridium complex. The invention also provides the organic electroluminescent device containing the iridium complex. Through use of 2,2,6,6-tetramethyl-3,5-heptanedione as an assistant ligand in the ring metal ligand, metal iridium complex steric-hinerance effect is improved so that direct effects between metal atoms are reduced, triplet exciton self-quenching phenomenon is reduced and luminescence efficiency of the organic electroluminescent device is improved.

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 周明杰王平张娟娟钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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