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Red light organic electroluminescent phosphorescent iridium compound

A phosphorescent iridium complex and electromechanical technology, applied in organic chemistry, circuits, electrical components, etc., can solve the problems of reduced luminous efficiency and poor stability of devices, and achieve the effects of reduced luminous efficiency, poor stability and good stability

Inactive Publication Date: 2011-08-17
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problems in the prior art that the luminous efficiency of the device decreases and the stability is poor due to the quenching of the material concentration, the present invention provides a class of benzothiazole-based iridium complexes that can emit bright red phosphorescence in a pure solid film

Method used

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  • Red light organic electroluminescent phosphorescent iridium compound
  • Red light organic electroluminescent phosphorescent iridium compound
  • Red light organic electroluminescent phosphorescent iridium compound

Examples

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Embodiment 1

[0039] The electrophosphorescent iridium complex in this embodiment is a red light material (abbreviated as Ir1 in the present invention), and the emission wavelength is made Red shift, and reduce the concentration quenching problem, realize the red light emission under the pure solid film. Its structural formula is as follows:

[0040]

[0041] The preparation process is:

[0042] 1. Synthesis of 2-(4-biphenyl)benzo[d]thiazole (ligand 1 for short):

[0043] At room temperature, add 0.1 mol of 4-biphenylcarboxylic acid and 10 mL of thionyl chloride into a 50 mL three-necked flask, and after refluxing for 3 hours, distill off the thionyl chloride under reduced pressure to obtain 4-bibenzoyl chloride. Add 30 mL of N-methylpyrrolidone to the prepared 4-bibenzoyl chloride, and slowly drop it into a solution of 0.1 mol o-aminothiophenol in 40 mL of N-methylpyrrolidone under the protection of argon. After the dropwise addition, the reactant was stirred at 100°C for 1 hour, the...

Embodiment 2

[0048] The electrophosphorescent iridium complex in this embodiment is an orange-red light material (abbreviated as Ir2 in the present invention), by using 4'-tert-butyl-4-biphenyl to replace the benzene in 2-phenylbenzothiazole Substituents make the emission wavelength red shift, and the molecule has a larger space volume, which can effectively reduce the aggregation of molecules. Its structural formula is as follows:

[0049]

[0050] The preparation process is:

[0051] 1. Synthesis of 4'-tert-butyl-4-biphenylcarboxylic acid

[0052] With 4-bromobiphenyl as raw material, 4'-tert-butyl-4-bromobiphenyl was first prepared with reference to the method reported in the literature [see (11) MurphyS.; Yang, X.; Schuster, G.B.et al., J. Org. Chem. 1995, 60, 2411]. Then, under argon protection, 0.1 mol of 4'-tert-butyl-4-bromobiphenyl, 0.11 mol of magnesium, and 15 mL of anhydrous tetrahydrofuran were added to a 100 mL three-necked flask, and refluxed for two hours to obtain 4'...

Embodiment 3

[0059] The electrophosphorescent iridium complex in this embodiment is an orange-red light material (abbreviated as Ir3 in the present invention), by using 3', 5'-di-tert-butyl-4-biphenyl to replace 2-phenylbenzo The phenyl substituent in thiazole makes its luminescence wavelength red-shifted and has a larger steric volume to improve its solid phosphorescence emission intensity. Its structural formula is as follows:

[0060]

[0061] The preparation process is:

[0062] 1. Synthesis of 3', 5'-di-tert-butyl-4-biphenylcarboxylic acid

[0063] Under the protection of argon, add 0.1mol of 4-bromobiphenyl, 20mL of carbon tetrachloride and 0.2g of anhydrous AlCl 3 , stirred in an ice bath for 12 hours, poured the reaction mixture into 200 mL of ice water, washed the organic phase successively with saturated sodium bicarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the remaining yellow s...

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Abstract

The invention discloses an iridium compound organic electroluminescent phosphorescent material capable of emitting bright red phosphorescence in a pure solid film. The material contains benzothiazole derivate cyclometalated ligand, xenyl and replaced xenyl are introduced on the benzothiazole, so that the maximum phosphorescent emitting wavelength bathochromic shift of the iridium compound reachesover 600 nanometers in the pure solid film, and the iridium compound is in salmon color and pure red color; simultaneously, the problem of reduction in emitting intensity of a solid phosphorescence material, caused by concentration quenching or triplet-triplet exciton annihilation, is avoided. A red-light electroluminescent phosphorescent device with an undoped structure can be prepared by using the iridium compound as a luminescent material; when the device works under the condition of higher current density, the luminous efficiency is not remarkably reduced, device performance is stable, and the luminous color is salmon color or pure red color.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to a class of organic electroluminescent materials of benzothiazole iridium complexes. Specifically, the present invention relates to a class of iridium complex red electrophosphorescent materials with cyclic metal ligands of 2-(4-biphenyl)benzothiazole derivatives. Background technique [0002] Organic electrophosphorescent materials have become a hot spot in the field of electroluminescence research in recent years because they can utilize singlet and triplet excitons at the same time, and their theoretical luminous quantum efficiency can reach 100%. Iridium complexes have become the most concerned electrophosphorescent materials due to their advantages such as high photoluminescence efficiency, short excited state lifetime, and the ability to obtain red, green, and blue three primary colors of light. Compared with green light devices, red electrophosphorescent...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
Inventor 卢志云李明代军黄艳谢明贵
Owner SICHUAN UNIV
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