Ruthenium complex with aggregation-induced phosphorescence enhancement properties, its preparation method and application

A ruthenium complex and aggregate state technology is applied in the application field of preparing electroluminescent devices, which can solve the problems of increasing the complexity and difficulty of devices, prone to phase separation, low luminous efficiency and the like, and achieves improving the electroluminescent efficiency of devices. , the effect of reducing production costs and simplifying the preparation process

Active Publication Date: 2018-10-12
南通北外滩建设工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the strong interaction between molecules of phosphorescent materials or the triplet-triplet annihilation mechanism between molecules, the concentration quenching problem occurs in the solid state of the material, so that the luminous efficiency is not high.
In order to solve this problem, the researchers doped the phosphorescent material as a guest into the host material, which increased the complexity and difficulty of device preparation, and the subsequent use of the device was prone to phase separation and reduced device life.

Method used

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  • Ruthenium complex with aggregation-induced phosphorescence enhancement properties, its preparation method and application
  • Ruthenium complex with aggregation-induced phosphorescence enhancement properties, its preparation method and application
  • Ruthenium complex with aggregation-induced phosphorescence enhancement properties, its preparation method and application

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preparation example Construction

[0049] The embodiment of the present invention also provides a method for preparing a ruthenium complex with aggregation-induced phosphorescence enhancement characteristics, which includes:

[0050] In a protective atmosphere, dissolve the soluble ruthenium salt with a molar ratio of 1:1-3 and the compound as the first ligand in the first solvent, and reflux the reaction for more than 6 hours, and obtain the intermediate product after cooling to room temperature;

[0051] Dissolve the intermediate product with a molar ratio of 1:3-8 and the 2,2-distyrylbenzene derivative as the second ligand in the second solvent, and react at 100-150°C for more than 6 hours, and the obtained reaction The mixture is post-treated to obtain the ruthenium complex.

[0052] Further, the molar ratio of the soluble ruthenium salt, the compound as the first ligand, and the 2,2-distyrylbenzene derivative is 1:1-3:3-8.

[0053] More preferably, the first solvent includes DMF, but not limited thereto. ...

Embodiment 1

[0067] (1) Synthesis of the second ligand 3-(4-(2,2-distyryl)phenyl)-1,10phenanthroline (DP)

[0068] Under nitrogen protection, 3-bromophenanthroline (0.10g, 0.40mmol), 4-(2,2-distyryl) phenylboronic acid (0.14g, 0.48mmol), tetrakis(triphenylphosphine) Add palladium and 20mL tetrahydrofuran into a 100mL three-necked round-bottomed flask and stir at room temperature for 10min, then add 4mL sodium carbonate aqueous solution (2M) to the reaction system and react at 70°C for 24h. , washed with water, dried over anhydrous sodium sulfate, concentrated, column chromatography (SiO 2 , eluent: dichloromethane / methanol volume ratio = 19:1) to obtain DP product 0.12g, yield 69.0%. Mass spectrometry is carried out to described DP: Ms (m / z): 434.1 (M + ). The reaction equation is as follows formula 1.

[0069]

[0070] (2) Ruthenium complex [Ru(bpy) 2 DP] (ClO 4 ) 2 preparation of

[0071] Under nitrogen protection, the RuCl 3 ·3H 2 O (1.56g, 6mmol), 2,2-bipyridine (1.87g, 12...

Embodiment 2

[0075] (1) The synthesis of the second ligand 3-(4-(2,2-distyryl)phenyl)-1,10phenanthroline (DP) is the same as in Example 1.

[0076] (2) Ruthenium complex [Ru(phen) 2 DP] (ClO 4 ) 2 preparation of

[0077] Under nitrogen protection, the RuCl 3 ·3H 2 O (1.56g, 6mmol), 1,10-phenanthroline (2.16g, 12mmol) and lithium chloride (1.68g, 28mmol) were dissolved in 10mL DMF and heated to reflux for 8h. After cooling to room temperature, add 50 mL of acetone and freeze overnight. Suction filtration, after the precipitate is rinsed with ice water and cold acetone, vacuum-dried to obtain [Ru(phen) 2 Cl 2 ] Purple-black microcrystals, yield 66.46%.

[0078] Under nitrogen protection, the [Ru(phen) 2 Cl 2 ] (0.053g, 0.1mmol), DP (0.217g, 0.5mmol) was dissolved in 5mL of ethylene glycol and reacted at 150°C for 8h, cooled to room temperature after the reaction was completed, diluted with 20mL of water, and then added sodium perchlorate Saturated solution until a large amount of ...

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Abstract

The invention discloses a ruthenium complex with aggregation state induced phosphorescence enhancement characteristics, its preparation method and application. The ruthenium complex has a structure shown in formula I: wherein, N^N bidentate ligand is the first ligand, X^X bidentate ligand is the second ligand, and the first ligand includes 2, 2-bipyridine or 1,10-phenanthroline, the second ligand includes 2,2-distyrylbenzene derivatives. The ruthenium complex can emit strong phosphorescence in an aggregated state, and when used to prepare electroluminescent devices, it is not necessary to dope it as a guest into the host material, thereby simplifying the device preparation process and reducing device manufacturing costs. The electroluminescence efficiency of the device is improved, which is beneficial to industrialization. At the same time, the method for preparing the ruthenium complex provided by the invention is simple, the conditions are easy to control, and it is convenient for large-scale implementation.

Description

technical field [0001] The invention specifically relates to a ruthenium complex with aggregation-induced phosphorescence enhancement characteristics, its preparation method and application, such as application in the preparation of electroluminescent devices, and belongs to the technical field of photoelectric materials. Background technique [0002] Traditional luminescent materials have strong emission intensity and high quantum yield in dilute solution. However, in high-concentration solutions, especially in aggregated states such as thin films and crystals, the energy of molecules in the excited state is attenuated through non-radiative pathways due to the strong intermolecular interactions, resulting in a decrease in the luminous efficiency of the luminescent material. A research group has reported that a series of silacyclic polyene compounds have the characteristics of aggregation-induced fluorescence emission. The aggregation-induced fluorescent materials solve the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0053C09K2211/185H10K85/344H10K50/00
Inventor 梁作芹王筱梅叶常青邹志扬
Owner 南通北外滩建设工程有限公司
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