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Triphenylene compound containing pyridine group and application thereof

A technology of organic compounds and compounds, applied in organic chemistry, electrical components, circuits, etc., can solve problems such as suppression of endothermic energy transfer process, short life of blue phosphorescent devices, and reduced device efficiency, so as to achieve high electron transport performance and improve Good electron transport performance and film-forming properties

Inactive Publication Date: 2012-07-04
TSINGHUA UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The study found that for the phosphorescent host-guest system of endothermic energy transfer, if a small amount of water and oxygen pollution is introduced during the device preparation process, the efficiency of the device will be greatly reduced; moreover, when the temperature decreases, the endothermic energy transfer process will be inhibited
At the same time, due to the large number of triplet excitons in the host, the energy cannot be transferred to the phosphorescent dye in time, which is also one of the reasons for the short lifetime of blue phosphorescent devices.

Method used

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  • Triphenylene compound containing pyridine group and application thereof
  • Triphenylene compound containing pyridine group and application thereof
  • Triphenylene compound containing pyridine group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation of embodiment 1 compound 1-1

[0039] (1) Preparation of aryl-substituted pyridine boronic acid:

[0040]

[0041] 23.5g (0.10mmol) 2,6-dibromopyridine, 12.0g phenylboronic acid and 0.50g Pd (PPh 3 ) 4 Dissolve in 300.0mL toluene, dissolve 22.0g potassium carbonate in 100.0mL water and add to the above reaction solution, the reaction solution immediately turns yellow at 50°C. As the reaction progressed, the color of the reaction solution gradually became lighter. After 1.5 h, 2.50 g of phenylboronic acid was added, and the reaction progress was monitored by TLC. After about 0.5h, the reaction was completed, and the organic layer was washed three times with anhydrous Na 2 SO 4 Carry out column chromatography after drying, eluent is sherwood oil: dichloro=20: 1 (V 1 / V 2 ) to obtain 15.1 g of off-white solid. MS (m / e): 234, melting point 47-49°, yield 64.3%. Dissolve the obtained product in 200.0 mL of dry tetrahydrofuran, then add 16.0 g of tri...

Embodiment 2

[0046] The synthesis of embodiment 2 compound 1-2

[0047] Using 2-chloro-4-iodopyridine and phenylboronic acid as raw materials, compound 1-2 was obtained through the same reaction as in Example 1. MS (m / e): 687, elemental analysis (C 51 h 33 N 3 ): theoretical value C: 89.06%, H: 4.84%, N: 6.11%; measured value C: 89.10%, H: 4.71%, N: 6.19%. Yield 62.4%.

Embodiment 3

[0048] The synthesis of embodiment 3 compound 1-3

[0049] Using 3,5-dibromopyridine and phenylboronic acid as raw materials, compound 1-3 was obtained through the same reaction as in Example 1. MS (m / e): 687, elemental analysis (C 51 h 33 N 3): theoretical value C: 89.06%, H: 4.84%, N: 6.11%; measured value C: 89.15%, H: 4.81%, N: 6.04%. Yield 58.8%.

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Abstract

The invention provides a novel compound, which has stable compound property, a simple preparation process, high luminous efficiency and high carrier mobility and can be applied to a phosphorescent main body material and an electron transfer layer of an electroluminescent element. According to an applied device, the driving voltage can be reduced remarkably, and the current efficiency is increased. The structural general formula of the compound is shown as a formula I, wherein a mother nucleus is selected from triphenylene; terminal groups Ar1, Ar2 and Ar3 are selected from a pyridine group, a phenyl group, a biphenylyl group or a naphthyl group; A, B and C are chemical bonds or aromatic rings with 6-30 carbon atoms; and m, n and p are integers of 0-2.

Description

technical field [0001] The invention relates to a novel organic material and its application in the technical field of organic electroluminescence display. Background technique [0002] Phosphorescent dyes usually cannot be used alone as the light-emitting layer of OLEDs, and need to be doped in a suitable host material to form a host-guest light-emitting layer. In order to achieve efficient energy transfer, the triplet energy level E of the host material is usually required T higher than the triplet energy level E of the dye molecule T . For red or green phosphorescent dyes, the currently commonly used host material CBP (structure shown in the figure below) performs well. However, for blue phosphorescent dyes, their own triplet energy is relatively high, and it is difficult to find host materials with higher triplet energy that match it. Taking the commonly used blue phosphorescent dye FIrpic as an example, its triplet energy level is 2.65eV, and the triplet energy leve...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D401/10H01L51/50H01L51/54
Inventor 邱勇孙绪霞李银奎段炼
Owner TSINGHUA UNIV
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