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Benzonitrile derivative and application thereof to production of electroluminescent device

A derivative, benzonitrile technology, applied in the field of benzonitrile derivatives and its application in the preparation of electroluminescent devices, can solve the problem that the luminescent color cannot be adjusted, and achieve excellent electroluminescence performance and good current carrying Sub-transmission characteristics, the effect of wide adjustment range of luminous peak position

Inactive Publication Date: 2019-05-03
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Some benzonitrile Compound 3Ph with carbazole and diphenylcarbazole as electron donor as electron acceptor 2 CzCzBN and 3Cz2DphCz, these two compounds can be used as light-emitting materials to prepare sky-blue photoluminescent devices with good performance. Since only carbazole or carbazole derivatives are used as electron donor groups when designing and synthesizing compounds, this technology can only obtain Sky blue photoluminescent device with luminous peak near 480nm, the luminous color cannot be adjusted

Method used

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  • Benzonitrile derivative and application thereof to production of electroluminescent device
  • Benzonitrile derivative and application thereof to production of electroluminescent device
  • Benzonitrile derivative and application thereof to production of electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0166] Embodiment 1: the synthesis of compound 1

[0167] Add 10 mmol of compound 1a, 15 mmol of diphenylamine, and 30 mmol of potassium tert-butoxide into a two-necked flask under nitrogen atmosphere, and add 50 mL of ultra-dry DMF under nitrogen atmosphere. Reflux reaction at about 160°C for 12h. After the reaction was completed, after the temperature of the system dropped to room temperature, it was poured into 1 L of ice water, stirred thoroughly, and filtered with suction. The filter cake was washed with deionized water and methanol three times in turn, and then dried. Using 200-300 mesh silica gel as the stationary phase, dichloromethane:petroleum ether=1:3 (volume ratio) as the eluent for column chromatography separation, the white powder that is product 1 can be obtained. The molecular ion mass determined by mass spectrometry is: 600.2 (calculated value: 600.2); theoretical element content (%) C 43 h 28 N 4 : C, 85.97; H, 4.70; N, 9.33; Measured element content (%...

Embodiment 2

[0169] Embodiment 2: the synthesis of compound 2

[0170] According to the reaction conditions and process of Example 1, using 1a and 4,4'-dimethyldiphenylamine as raw materials, white solid compound 2 was obtained. The molecular ion mass determined by mass spectrometry is: 628.2 (calculated value: 628.3); theoretical element content (%) C 45 h 32 N 4 : C, 85.96; H, 5.13; N, 8.91; Measured element content (%): C, 85.96; H, 5.13; N, 8.91.

Embodiment 3

[0171] Embodiment 3: the synthesis of compound 3

[0172] According to the reaction conditions and process of Example 1, using 1a and 4,4'-diisopropyldiphenylamine as raw materials, white solid compound 3 was obtained. The molecular ion mass determined by mass spectrometry is: 684.3 (calculated value: 684.3); theoretical element content (%) C 49 h 40 N 4 : C, 85.93; H, 5.89; N, 8.18; Measured element content (%): C, 85.93; H, 5.89; N, 8.18.

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Abstract

The invention discloses a benzonitrile derivative substituted by bicarbazole-aromatic amine or an aromatic amine derivative and an application of the benzonitrile derivative to production of an electroluminescent device and belongs to technical field of organic electroluminescence. The compound disclosed by the invention has a structural formula as shown in the following specification, two carbazoles with relatively weak electron donating ability or carbazole derivatives are introduced to an ortho-position of a CN group, and the CN group is encircled by using two conjugated groups with relatively large volumes, which are beneficial to the improvement of light emitting efficiency and stability of a material; and two carbazole groups with conjugated structures are introduced to the ortho-position of the CN group, so that the benzonitrile derivative is good in carrier transportation characteristic and capable of improving the carrier transportation performance of the material and makes the material have good electroluminescent property under the condition that the material is not doped.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and in particular relates to a benzonitrile derivative and its application in preparing electroluminescent devices. Background technique [0002] In the early 1960s, Pope et al. first reported the phenomenon of organic electroluminescence. When they applied a high voltage of 400 volts on both sides of anthracene single crystal, they observed the blue light emitted by anthracene (see M.Pope, H.Kallmann and P. Magnante, J. Chem. Phys., 1963, 38, 2042). However, due to the difficulty of growing single crystals and the high driving voltage of the device, the process they used has little practical use. Until 1987, C.W.Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as the hole transport layer, aluminum complexes of 8-hydroxyquinoline as the light-emitting layer, and indium tin oxide (I...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07D417/14C07D401/14C07D413/14C07F7/08C09K11/06H01L51/50H01L51/54
Inventor 王悦
Owner JILIN UNIV
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