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Preparation method and application of 4,4'-substituted benzil core-based luminescence and host material

A technology of host material and benzil nucleus, which is applied in the field of preparation and application of luminescence and host materials, can solve problems such as the potential of organic light-emitting diodes to be tapped, and achieve the effects of improving external quantum efficiency, good solubility, and single structure

Active Publication Date: 2015-12-23
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] So far, there have been some reports on organic light-emitting small molecules with 4,4'-substituted benzil as the core, but a lot of work has focused on using it as an organic reaction intermediate, and its potential in organic light-emitting diodes remains to be tapped
At the same time, there is no related report on this thermally excited delayed fluorescent material as a sensitization host for solution processing.

Method used

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  • Preparation method and application of 4,4'-substituted benzil core-based luminescence and host material
  • Preparation method and application of 4,4'-substituted benzil core-based luminescence and host material
  • Preparation method and application of 4,4'-substituted benzil core-based luminescence and host material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In this example, the luminescent and host material P1 based on 4,4'-substituted benzil nucleus is prepared, and the reaction is shown in the following formula:

[0036]

[0037] Specific implementation steps: add 4,4'-dibromo-substituted benzil (0.368mg, 1mmol) and carbazole (367.4mg, 2.2mmol) and potassium carbonate (552mg, 4mmol) to dry toluene in a 250ml three-necked flask, Palladium acetate (44mg, 0.2mmol) was added under nitrogen protection, and then tri-tertbutylphosphine (0.73ml, 0.73mmol) was added dropwise thereto. Under the protection of nitrogen, the reaction was heated to reflux for 12h. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and passed through a silica gel column to obtain 500 mg of a yellow solid (90% yield). Molecular formula: C 38 h 24 N 2 o 2 ; Molecular weight: 540.62; Elemental analysis: C, 84.42; H, 4.47; N, 5.18; O, 5.92. ...

Embodiment 2

[0039] In this example, the luminescent and host material P2 based on 4,4'-substituted benzil nucleus is prepared, and the reaction is shown in the following formula:

[0040]

[0041] Specific implementation steps: in a 250ml three-necked flask, add 4,4'-dibromo-substituted benzil (0.368mg, 1mmol) and tert-butylcarbazole (614mg, 2.2mmol) and potassium carbonate (552mg, 4mmol) to dry toluene , palladium acetate (44mg, 0.2mmol) was added under nitrogen protection, and then tri-tertbutylphosphine (0.73ml, 0.73mmol) was added dropwise thereto. Under the protection of nitrogen, the reaction was heated to reflux for 12h. After the reaction was completed, it was cooled to room temperature, extracted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, and passed through a silica gel column to obtain 700 mg of a yellow solid (91.5% yield). Molecular formula: C 54 h 56 N 2 o 2 ; Molecular weight: 765.05; Elemental analysis: C, 84.78; H, 7.38; N, 3.6...

Embodiment 3

[0043] In this example, the luminescent and host material P3 based on 4,4'-substituted benzil nucleus is prepared, and the reaction is shown in the following formula:

[0044]

[0045] Specific implementation steps: under a nitrogen atmosphere, add 100ml of toluene, 30ml of absolute ethanol, 40ml of 2M potassium carbonate aqueous solution, 4,4'-dibromo-substituted benzil (0.368mg, 1mmol), p-carbazole to a 250ml flask Phenylboronate (811mg, 2.2mmol), and then 200mg of triphenylphosphopalladium catalyst was added, and the mixture was refluxed at 110°C for 12 hours. Cool to room temperature, extract with dichloromethane, and dry over anhydrous magnesium sulfate. Column chromatography separated 600 mg of yellow solid with a yield of 86.7%. Molecular formula: C 50 h 32 N 2 o 2 ; Molecular weight: 692.82; Elemental analysis: C, 86.68; H, 4.66; N, 4.04; O, 4.62.

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Abstract

The invention belongs to the technical field of organic photoelectric materials, and discloses a preparation method and an application of a 4,4'-substituted benzil core-based luminescence and host material. The luminescent material is prepared through a Buchwald-Hartwig coupling reaction from 4,4'-dibromobenzil as an initial reaction raw material under the protection of nitrogen. The luminescent material adopts 4,4'-substituted benzil as a host structure, and the connection mode of a donor is changed to adjust the molecular weight, the pi conjugacy and eletrophilicity, the charge transfer ability and the photochromism of the material and effectively solve the carrier imbalance problem of unipolar luminescent materials. The material can be used in organic light-emitting diodes to greatly improve the external quantum efficiency of traditional fluorescent organic light-emitting diode devices.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to the preparation and application of a luminescent and host material based on a 4,4'-substituted benzil nucleus. Background technique [0002] In order to improve the efficiency of organic photoelectric devices, compared with polymer materials, small molecule materials can obtain higher device efficiency due to their definite structure and convenient purification, so that they may be commercially applied. However, the efficiency of devices based on traditional organic fluorescent materials is greatly limited because only 25% of the singlet excitons can be utilized. Recently, the Japanese Adachi research group used the mechanism of thermally activated delayed fluorescence, and the exciton utilization rate of all organic materials can also reach 100%, making the device efficiency of organic fluorescence leap forward. However, due to the variety of ...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/86C07C225/22C07C221/00C07D279/22C07D241/48C07D219/14C07D265/38H01L51/54
Inventor 苏仕健蔡欣佚陈东俊彭俊彪曹镛
Owner SOUTH CHINA UNIV OF TECH
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