Triphenylamine substituted-vinyl modified phenanthroimidazole compound, preparation method thereof and application of compound as electroluminescent device

A technology of phenanthroimidazole and triphenylethylene, which is applied in the field of organic light-emitting materials and optoelectronic devices, can solve the problem of taking into account the good carrier transport ability of light-emitting materials, high fluorescence quantum yield, and weak electron transport and hole transport capabilities. , unbalanced device carrier transport and other issues, to achieve the effect of strengthening the aggregation-induced luminescence effect, carrier injection and transport balance, and avoiding efficiency decline

Active Publication Date: 2019-05-03
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, although there have been many reports on phenanthroimidazole-based light-emitting materials used in small-molecule organic electroluminescent devices, most of them are in the aggregation state due to the formation of π-π stacking due to the planar structure of the molecules, resulting in their fluorescence being suppressed. quenching, thereby reducing its device efficiency
In addition, vinyl-modified light-emitting materials with aggregation-induced light-emitting properties have weak electron transport and hole transport capabilities of the molecule itself, resulting in unbalanced carrier transport and poor device performance in devices using it as the light-emitting layer.
It is difficult to balance the good carrier transport ability of luminescent materials and the dilemma of high fluorescence quantum yield in aggregated state

Method used

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  • Triphenylamine substituted-vinyl modified phenanthroimidazole compound, preparation method thereof and application of compound as electroluminescent device
  • Triphenylamine substituted-vinyl modified phenanthroimidazole compound, preparation method thereof and application of compound as electroluminescent device
  • Triphenylamine substituted-vinyl modified phenanthroimidazole compound, preparation method thereof and application of compound as electroluminescent device

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Experimental program
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Effect test

Embodiment 1 3

[0048] The preparation of the phenanthroimidazole that embodiment 1 triphenylamine replaces-tristyryl modification

[0049]Step 1: Preparation of 4-bromophenanthroimidazole (i.e. compound 1):

[0050] Add 4-bromobenzaldehyde (1.86g, 10mmol), aniline (1.49g, 10mmol), 9,10-phenanthrenequinone (2.08g, 10mmol), ammonium acetate (4.62g, 60mmol) into a 100ml two-necked flask in sequence, And 60ml of glacial acetic acid was added to obtain a dark brown suspension. After the mixture was stirred at 120° C. for 2 hours, the color of the solution changed from dark brown to black, and the reaction mixture was stirred overnight (12 hours) at room temperature. The crude product was isolated by washing with methanol and filtration, then dried in vacuo. Using silica gel powder as stationary phase, petroleum ether and dichloromethane as eluent (petroleum ether: CH 2 Cl 2 ,1:2) to obtain a white powder with a yield of 82.1%.

[0051] The reaction equation is as follows:

[0052]

[005...

Embodiment 2 3

[0069] The preparation of the phenanthroimidazole of embodiment 2 triphenylamine substitution-tetrastyryl modification

[0070] The preparation process of the phenanthrene imidazole substituted by triphenylamine-tetrastyryl modification, steps 1 to 3 are the same as in Example 1, and steps 4 and 5 are as follows:

[0071] Step 4: Preparation of 4-bromotriphenylamine tetraphenylethylene

[0072] 4-triphenylamine benzophenone (1.53g, 3.60mmol) and 4-bromobenzophenone (0.80g, 7.20mmol) zinc powder (2.0g) were added in a 100ml two-necked flask, and the flask was placed under vacuum Evacuate and replace in dry nitrogen three times, then add 50ml of THF to remove water and oxygen, and then stir in a low-temperature reactor at -10°C (30 minutes). Then add 6ml of TiCl dropwise with a needle 4 , and stirred at -10°C for 30 minutes. After the reaction was warmed to room temperature, the reaction was quenched with 1M hydrochloric acid, and extracted with saturated brine and dichloromet...

Embodiment 3

[0081] Embodiment 3 performance test

[0082] Taking the compounds M1 and M2 prepared in Example 1 and Example 2 as test objects, their photophysical properties and other luminescent properties were tested, and the test results were as follows: Figure 3 to Figure 8 shown.

[0083] image 3 The oxidation-reduction potentials of molecules M1 and M2 were measured by cyclic voltammetry on a Metrohm PGSTAT 302N high-precision electrochemical workstation. Such as image 3 As shown, wherein M1 is triphenylamine-substituted-triphenylethylene-modified phenanthroimidazole, and M2 is triphenylamine-substituted-tetraphenylethylene-modified phenanthroimidazole. The oxidation potentials of both are relatively high, indicating that the highest occupied orbital is relatively high, which is conducive to the injection and transmission of holes and electrons, and can be used for vacuum evaporation to make organic electroluminescent devices.

[0084] Figure 4 The fluorescence emission spec...

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Abstract

The invention discloses a triphenylamine substituted-vinyl modified phenanthroimidazole compound, a preparation method thereof and an application of the compound as an electroluminescent device. The structural general formula of the compound is shown in a formula (I), wherein R is hydrogen or phenyl. According to the invention, excellent characteristics of phenanthroimidazole materials and triphenylamine substituted-vinyl are adopted, meanwhile, a donor and a receptor are connected through the vinyl, and the pi electron ionization region can be effectively improved, so that carrier injection and transmission are more balanced, then fluorescence quantum efficiency is improved, and high-fluorescence quantum efficiency of a solid-state thin film under an aggregation state is achieved; and meanwhile, blue-green light can be efficiently emitted in an organic solvent, and organic luminescent small molecules with good carrier transmission capability and high fluorescence quantum yield under aaggregation state are synthesized. The compound provided by the invention can be used as a luminescent material to be widely applied to organic luminescent devices, in particular to the stable and efficient organic electroluminescent devices.

Description

technical field [0001] The invention relates to the technical field of organic light-emitting materials and their application in optoelectronic devices, more specifically, a triphenylamine-substituted-vinyl modified phenanthroimidazole compound, a preparation method thereof and an application as an electroluminescent device. Background technique [0002] With the rise of high-tech products such as large-screen smartphones, tablet computers, and wearable devices, traditional liquid crystal display materials are becoming more and more difficult to meet the increasingly thinner and lower power consumption requirements of mobile terminals. Humans have begun to pay attention to organic electroluminescent devices with advantages such as higher flexibility, thinner thickness, lower power consumption, wider viewing angle, and higher color saturation. Among them, OLED devices are of decisive significance to display technologies such as full-color display and solid-state lighting. So...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/18C09K11/06H01L51/54
Inventor 邱志鹏霍延平籍少敏李琦王凯谭继华
Owner GUANGDONG UNIV OF TECH
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