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Benzophenanthrene compound containing benzoglioxaline group and application thereof

A compound and organic technology, applied in the field of new organic materials, can solve problems such as inhibition of endothermic energy transfer process, short life of blue phosphorescent devices, and reduced device efficiency, so as to achieve high electron transport performance, improve electron transport performance, and film formation good sex effect

Active Publication Date: 2015-03-11
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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  • Benzophenanthrene compound containing benzoglioxaline group and application thereof
  • Benzophenanthrene compound containing benzoglioxaline group and application thereof
  • Benzophenanthrene compound containing benzoglioxaline group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation of embodiment 1 compound 1-1

[0040]

[0041] 11.8g (0.10mmol) of benzimidazole was dissolved in 10.1mL of triethylamine, 28.1g (0.10mmol) of isobromoiodobenzene was added dropwise at zero temperature, stirred at room temperature for 30 minutes, then heated to 70-80°C and stirred for 2 hours. The reaction was quenched with water, extracted with dichloromethane, dried over magnesium sulfate, and recrystallized from methanol to obtain 23.8 g of compound A, which was dissolved in dry THF, and n-butyl was added dropwise at -80°C, stirred for 15 minutes, and then three Isopropyl borate. Hydrolyze, adjust the pH to neutrality and precipitate compound B.20.2g. The coupling reaction between B and 5,8-dibromobenzo[c]phenanthrene 1:1 was carried out to obtain intermediate C, which was reacted with compound E to obtain compound 1-1. It was purified by column chromatography, and the eluent was petroleum ether:dichloromethane=2:1. MS (m / e): 573, elemental anal...

Embodiment 2-30

[0046] Examples 2-30 are all similar to Example 1, and the target product can be obtained by reacting intermediate C with different aryl-substituted pyridine boronic acids. The details are as follows:

Embodiment 2

[0047] The synthesis of embodiment 2 compound 1-2

[0048] Using intermediate C and 6-phenyl-2-pyridineboronic acid as raw materials, compound 1-2 is obtained. MS (m / e): 573, elemental analysis (C 42 h 27 N 3 ): theoretical value C: 87.93%, H: 4.74%, N: 7.32%; measured value C: 87.90%, H: 4.81%, N: 7.29%. Yield 61.3%.

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PUM

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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 benzene[c]phenanthrene; Ar is selected from a phenyl group, a biphenylyl group or a naphthyl group; R is alkyl with 1-12 carbon atoms or aryl with 6-30 carbon atoms; m is an integer of 1-2; and n is an integer of 0-1.

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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/20C07D235/18C07D235/08H01L51/50H01L51/54
Inventor 邱勇孙绪霞李银奎段炼
Owner TSINGHUA UNIV
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