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, electric solid devices, organic chemistry and other directions, can solve the problems of affecting the luminous efficiency, small steric hindrance and poor stability of iridium complex phosphorescent materials, and reduce self-efficacy. Quenching phenomenon, less difficulty, and the effect of improving electroluminescence performance

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 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-methyl-4-(4',6'-dimethylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione)iridium, with 1-methyl-4-(2',4'-dimethylphenyl)phthalazine as Cyclometallic ligands, 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-methyl-4-chlorophthalazine, and B1 is 2,4-dimethylphenylboronic acid.

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

[0068]

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

Embodiment 2

[0091] A red-light organic electrophosphorescent material metal iridium complex bis[1-methyl-4-(5',6'-dimethylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione) iridium, with 1-methyl-4-(2',3'-dimethylphenyl)phthalazine as Cyclometallic ligands, 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-methyl-4-chlorophthalazine, and B2 is 2,3-dimethylphenylboronic acid.

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

[0100]

[0101] Under nitrogen protection, 0.72g (4.0mmol) 1-methyl-4-chlorophthalazine, 0.6g (4mmol) 2,3-m...

Embodiment 3

[0122] A red-light organic electrophosphorescent material metal iridium complex bis[1-methyl-4-(3',6'-dimethylphenyl)phthalazine-N,C 2 '](2,2,6,6-tetramethyl-3,5-heptanedione)iridium, with 1-methyl-4-(2',4'-dimethylphenyl)phthalazine as Cyclometallic ligands, 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-methyl-4-chlorophthalazine, and B3 is 2,5-dimethylphenylboronic acid.

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

[0131]

[0132] Under nitrogen protection, 0.72g (4.0mmol) 1-methyl-4-chlorophthalazine, 0.72g (4.8mmol) 2,5-dime...

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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 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 2,2,6,6-tetramethyl-3,5-heptanedione 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, 2,2,6,6-tetramethyl-3,5-heptanedione is added to the ring metal ligand as the auxiliary ligand so as to increase the steric hindrance effect of the metal iridium coordination compound, such that the direction effect between the metal atoms is reduced, the self-quenching phenomenon of the triplet state excitons is reduced, and the luminescence efficiency of the organic electroluminescent device is increased.

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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