A kind of phenanthroimidazole derivative and application thereof

A technology of phenanthroimidazole and derivatives, which is applied to phenanthroimidazole derivatives and their application fields, can solve the problems of low mobility, difficult to prepare high-efficiency OLED devices, and needs to be improved, and achieves improved electron transport ability, Good electron/hole transport ability, the effect of improving external quantum efficiency

Active Publication Date: 2017-09-26
HUAZHONG UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] To obtain an OLED device with excellent performance, it is necessary to select a transport material with sufficient mobility to ensure the balance of electrons and holes in the light-emitting layer. However, electron transport materials are currently in short supply. Alq 3 It is widely used for its good stability, but due to its low mobility, it is difficult to prepare high-efficiency OLED devices
[0004] The electron mobility of existing electron transport materials still needs to be improved, and the development of high mobility electron transport materials for the preparation of efficient OLED devices has always been a hot spot in our research

Method used

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  • A kind of phenanthroimidazole derivative and application thereof
  • A kind of phenanthroimidazole derivative and application thereof
  • A kind of phenanthroimidazole derivative and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0038] A kind of phenanthroimidazole derivative, it has the structure of formula (I), wherein R 1 for pyridine ie R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 It is a hydrogen atom; its chemical name is 2-(4-(3-pyridine)phenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole, referred to as CPI-p3Py, and its structural formula is as follows:

[0039]

[0040] Its preparation method is as follows: under the protection of nitrogen, compound 2-(4-bromophenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole (1) (1.76g, 4.0mmol) , 3-pyridine boronic acid (0.50g, 4.0mmol), toluene (100ml), absolute ethanol (50ml), 2M K 2 CO 3 (50ml) aqueous solution was successively added to a dry 500ml two-necked round-bottomed flask, ultrasonicated for 30 minutes, under nitrogen conditions, the reaction was heated to 80°C, stirred and refluxed for 24 hours, and the reaction was cooled to room temperature, and dichloromethane (60ml) was added. Extracted three times, collected the organic phase and...

Embodiment 2

[0042] A kind of phenanthroimidazole derivative, it has the structure of formula (I), wherein R 1 for pyridine ie R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 It is a hydrogen atom; its chemical name is 2-(3-(3-pyridine)phenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole, referred to as CPI-m3Py, and its structural formula is as follows:

[0043]

[0044] The synthesis process is the same as that of the compound CPI-p3Py to obtain 1.50 g of white solid 2-(3-(3-pyridine)phenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole (CPI-m3Py) . Yield: 84%. 1 H-NMR (CDCl 3 ,400MHz): δ(ppm)8.933~8.913(d,1H),8.799~8.778(d,1H),8.738~8.717(d,1H),8.628~8.611(d,2H),7.777~7.660(m, 8H), 7.599~8.534 (m, 4H), 7.463~7.434 (t, 1H), 7.296~7.235 (m, 3H). 13 C-NMR (CDCl 3 ,400MHz):δ(ppm)150.19,148.61,148.18,138.82,137.64,137.44,134.37,131.29,130.36,129.98,129.37,129.20,129.13,128.33,128.27,128.04,127.43,127.36,127.16,126.35,125.74, 125.05, 124.16, 123.57, 123.16, 122.97, 122.76, 120.91. MS(...

Embodiment 3

[0046] A kind of phenanthroimidazole derivative, it has the structure of formula (I), wherein R 1 is a hydrogen atom, R 2 for pyridine ie R 3 is a hydrogen atom, R 4 It is a hydrogen atom; its chemical name is 2-(4-(3-pyridine)phenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole, referred to as NPI-p3Py, and its structural formula is as follows:

[0047]

[0048] The synthesis process was the same as that of the compound CPI-p3Py, and 1.46g of white solid 2-(4-(3-pyridine)phenyl)-1-phenyl-1H-[9,10-d]phenanthroimidazole (NPI-p3Py) was obtained . Yield: 82%. 1 H-NMR (CDCl 3 ,400MHz): δ(ppm)9.031~9.025(d,1H),8.939~8.920(d,1H),8.813~8.792(d,1H),8.746~8.704(t,2H),8.045~8.025(d, 1H), 7.838~7.761(m,3H), 7.689~7.619(m,5H), 7.557~7.531(m,1H), 7.489~7.458(m,1H), 7.360~7.284(m,5H). 13 C-NMR (CDCl 3 ,400MHz):δ(ppm)151.03,149.28,148.31,139.10,138.56,137.42,135.04,134.51,130.31,129.83,129.54,129.34,129.01,128.58,128.34,128.31,128.02,127.38,127.11,126.37,126.37, 125.76, 125.02, 124....

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Abstract

The invention discloses a phenanthroimidazole derivative, which has higher triplet energy, high glass transition temperature, and good electron / hole transport ability. When it is used as an electron-transporting material, compared with the traditional host material in which the electron-transporting material BCP is an electron-transporting group commonly used in the prior art, the electron-transporting ability is significantly improved. In organic electroluminescent devices, the compound Compared with traditional electron transport materials, it has significantly improved glass transition temperature, current efficiency, power efficiency, external quantum efficiency and roll-off, and is an ideal electron transport material.

Description

technical field [0001] The invention belongs to the field of photoelectric materials, and more specifically relates to a phenanthroimidazole derivative and its application. Background technique [0002] The phenomenon of organic electroluminescence was first discovered in 1963. At that time, organic anthracene crystals were used as light-emitting materials. Because the driving voltage of this device was as high as 400V, and the device efficiency and lifespan were far inferior to inorganic electroluminescent devices, it did not attract people's attention at that time. In 1987, Deng Qingyun's (Tang, C.W.et al.Appl.Phys.Lett.1987,52,913) research group first proposed the OLED structure of organic multilayer amorphous thin films; in 1990, Burroughes et al. (Burroughes, J.H.etal.Nature. 1990,347,539) reported polymer light-emitting diodes for the first time, and since then, the research on organic electroluminescence has entered a new stage. In the past ten years, organic light-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D401/10C07D403/10C07D417/10C09K11/06H01L51/54
CPCC09K11/06C07D401/10C07D401/14C07D403/10C07D417/10C09K2211/1044C09K2211/1051H10K85/657H10K85/6572
Inventor 王磊穆广园汪博谭江洪
Owner HUAZHONG UNIV OF SCI & TECH
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