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Benzimidazole compounds, synthesis and application of benzimidazole compounds in OLEDs (organic light-emitting diodes)

A technology of benzimidazole and phenylbenzimidazole is applied in the field of organic electroluminescent materials, which can solve the problems of complicated synthesis, increase production cost and cycle, etc., and achieve the effect of improving device performance.

Inactive Publication Date: 2015-05-13
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the synthesis of TPBI is cumbersome and requires multi-step reactions to complete [S.Takizawa, V.A.Montes, and P.Anzenbacher, Jr, Chem.Mater., 2009,21,2452–2458], which increases production costs and cycles

Method used

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  • Benzimidazole compounds, synthesis and application of benzimidazole compounds in OLEDs (organic light-emitting diodes)
  • Benzimidazole compounds, synthesis and application of benzimidazole compounds in OLEDs (organic light-emitting diodes)
  • Benzimidazole compounds, synthesis and application of benzimidazole compounds in OLEDs (organic light-emitting diodes)

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Embodiment (1

[0016] Embodiment (1): the synthesis of iTPBI-CN

[0017] 2,4,6-Trifluorobenzonitrile (0.25g, 1.6mmol), potassium carbonate (0.99g, 7.2mmol), 2-phenylbenzimidazole (1.02g, 5.2mmol), DMSO 8ml, heated to reflux at 150°C 12h. Cooled to room temperature and poured into 200ml of water to precipitate a large amount of solid, stirred for 0.5h, filtered with suction to obtain a white solid, and purified by column chromatography to obtain 0.95g of a white solid, with a yield of 88%. Its hydrogen spectrum is shown in figure 1 . 1 H NMR (300MHz, (CD 3 ) 2 SO): δppm 8.34(s,2H),7.91-7.88(m,3H),7.72-7.61(m,12H),7.48-7.38(m,9H),7.29-7.27(d,3H,J=6Hz) ; 13 C NMR (75MHz, (CD 3 ) 2 SO,): δppm 155.2, 155.1, 145.8, 145.7, 145.6, 144.3, 138.8, 133.3, 133.1, 132.9, 132.6, 132.3, 132.2, 132.0, 126.9, 126.6, 122.8, 122.7, 115.2, 113.114. , 113.3; mass spectrum (m / z): 679.637[M+]; elemental analysis C46H29N7: calculated C 81.28, H 4.30, N 14.42; experimentally measured C 81.35, H 4.09, N 14.58...

Embodiment (2

[0020] Embodiment (2): solution method prepares organic electroluminescent device

[0021] The organic electroluminescent device includes glass, a conductive glass substrate layer attached to the glass, a hole injection layer bonded to the conductive glass substrate layer, a light-emitting layer bonded to the hole injection layer, and an electron transport layer bonded to the light-emitting layer. layer, and a cathode bonded to the electron transport layer, wherein the electron transport layer is prepared by using the iTPBI-CN described in the present invention and the TPBI described in the prior art respectively.

[0022] The ITO glass substrate was ultrasonically treated with detergent, organic solvent mixed with ethanol and acetone, and deionized water, and then dried in a drying oven at 120 ° C for more than 1 h. Take out the ITO substrate, after UV treatment for 4min, spin 40nm thick PEDOT:PSS, and anneal at 120°C for 15min. Spin a light-emitting layer with a thickness o...

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Abstract

The invention discloses benzimidazole compounds, synthesis and an application of the benzimidazole compounds in OLEDs (organic light-emitting diodes). The compounds are prepared through the following steps: 2-phenylbenzimidazole, 2,4,6-trifluorobenzonitrile and alkali are added to an organic solvent, have a reflux reaction for 5-12 h in the nitrogen environment, then are subjected to ethanol recrystallization or column chromatography separation and purification to prepare the compounds. According to the compound iTPBI-CN containing benzimidazole units, the benzimidazole units and cyanophenyl units are connected in a C-N manner, while an expensive noble metal catalyst is required to be added for forming a C-N bond in the traditional method. Besides, the iTPBI-CN serving as an electron transfer layer material is applied to the OLEDs, and the device performance still has larger promotion space.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a benzimidazole compound, its synthesis and its application in OLEDs. technical background [0002] Organic electroluminescent devices (OLEDs) are self-luminous devices with advantages such as low voltage, wide viewing angle, fast response speed, and good temperature adaptability. They are a new generation of display technology. The principle of organic electroluminescent devices, under the action of an electric field, holes and electrons are injected from the anode and cathode respectively, pass through the hole injection layer, the hole transport layer and the electron injection layer, and the electron transport layer respectively, and recombine in the light-emitting layer to form an excitation layer. The exciton radiation decays and emits light. [0003] One of the keys to improving the efficiency and lifetime of organic electroluminescent devices is the ba...

Claims

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Application Information

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IPC IPC(8): C07D235/18H01L51/54
CPCC07D235/18H10K85/6572
Inventor 陶友田王芳芳汤超黄维
Owner NANJING UNIV OF TECH
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