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Benzophenanthrene compound containing benzoglioxaline group and application thereof

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

Active 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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  • 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] Example 1 Preparation of 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 degree, stirred at room temperature for 30 minutes and then heated to 70-80°C and stirred for 2 hours. The reaction was quenched with water, extracted with dichloromethane, dried with magnesium sulfate, and recrystallized from methanol to obtain 23.8g of compound A. Dissolve A in dry THF, add n-butyl oligomer at -80°C, stir for 15min, and add three Isopropyl borate. After hydrolysis, adjust the pH to neutral and precipitate compound B. 20.2g. A 1:1 coupling reaction between B and 5,8-dibromobenzene[c]phenanthrene was carried out to obtain intermediate C, and C and compound E were reacted to obtain compound 1-1. Purified by column chromatography, the eluent is petroleum ether: dichloromethane = 2:1. MS(m / e): 573, elemental analysis (C 42 H 27 N 3 ): Theoretical value C: 87.93...

Embodiment 2-30

[0046] Examples 2-30 are all similar to Example 1. Intermediate C reacts with pyridine boronic acid substituted with different aryl groups to obtain the target product. The details are as follows:

Embodiment 2

[0047] Example 2 Synthesis of 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%. The yield was 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 new type of organic material and its application in the field of organic electroluminescence display technology. Background technique [0002] Phosphorescent dyes generally cannot be used as the light-emitting layer of OLED alone, and need to be doped into a suitable host material to form a host-guest light-emitting layer. In order to achieve effective 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 as shown in the figure below) performs well. However, for blue phosphorescent dyes, their triplet energy is relatively high, and it is more difficult to find a host material with higher triplet energy that matches it. Taking the currently commonly used blue phosphorescent dye FIrpic as an example, its triplet energy level is 2.65 eV, and th...

Claims

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Application Information

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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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