Compound with cyano structure and organic light-emitting device thereof
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A technology of organic light-emitting devices and compounds, applied in the field of compounds containing cyano groups and their organic light-emitting devices, to achieve the effects of saving materials, good application effects, and good industrialization prospects
Active Publication Date: 2018-12-21
CHANGCHUN HYPERIONS TECH CO LTD
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[0003] Organic electroluminescent materials have continuously achieved breakthroughs in recent years, and have made remarkable progress, posing a strong challenge to traditional display materials.
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Embodiment 1
[0076] [Example 1] Synthesis of Compound 1
[0077]
[0078] Synthesis of compound a1
[0079] Into a 250 mL two-necked flask was added 200 mL of DMF (dimethylformamide), followed by pentafluoropyridine (17.5 g, 103.5 mmol), potassium carbonate (17.2 g, 124.3 mmol) and ethyl cyanoacetate (11.7 g, 103.5 mmol) , stirred at room temperature for 48 hours. Distilled water and acetic acid were added dropwise to the mixture to terminate the reaction, and then extracted with dichloromethane, the organic phases were combined and dried, concentrated, and recrystallized to obtain compound a1 (24.4 g, yield 90%).
[0080] Mass Spectrum m / z: 262.12 (calculated: 262.16). Theoretical element content (%) C 10 h 6 f 4 N 2 o 2 : C, 45.81; H, 2.31; F, 28.99; N, 10.69; O, 12.21 The measured element content (%): C, 45.81; The above results confirmed that the obtained product was the target product.
[0092] The pentafluoropyridine in Example 1 was replaced by equimolar cyanuric fluoride, and the other steps were the same as in Example 1 to obtain the target compound 13. Mass Spectrum m / z: 510.50 (calculated: 510.54). Theoretical element content (%)C 33 h 20 f 2 N 4 : C, 77.63; H, 3.95; F, 7.44; N, 10.97 The measured element content (%): C, 77.64; H, 3.96; F, 7.44; N, 10.96. The above results confirmed that the obtained product was the target product.
Embodiment 3
[0093] [Example 3] Synthesis of compound 18
[0094]
[0095] The compound b1 in Example 1 was replaced with equimolar 2-(perfluorophenyl)acetonitrile, and the other steps were the same as in Example 1 to obtain the target compound 18. Mass Spectrum m / z: 561.56 (calculated: 561.54). Theoretical element content (%)C 36 h 20 f 5 N: C, 77.00; H, 3.59; F, 16.92; N, 2.49 Measured element content (%): C, 77.03; H, 3.56; F, 16.93; N, 2.48. The above results confirmed that the obtained product was the target product.
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Abstract
The invention discloses a compound with a cyano structure and an organic light-emitting device thereof. On one hand, a fluorine ene group adopts a three-dimensional space structure and is not liable to crystallize; fluorine end double bond is connected with a cyano group, and one side is connected with a series of electron-withdrawing groups such as fluorine, cyano and trifluoromethyl, so that theelectronic transmission performance of the structure is improved. On the other hand, the compound with a cyano structure, which is formed by combining the fluorine group and the fluorine ene group, has an extensible three-dimensional structure, so that the compound is distorted certainly in the spatial three-dimensional structure and the film-forming property is improved; furthermore, the compound has proper HOMO and LUMO value and can effectively block transmission of a hole to an electronic transmission layer, and the hole encounters the electron in a light-emitting layer, so that effectiveluminescence is improved. The compound is applied to a light-emitting layer or a hole blocking layer of the organic light-emitting device, and the device shows up the advantages of low driving voltage and high light-emitting efficiency.
Description
technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a compound containing a cyano group structure and an organic light-emitting device thereof. Background technique [0002] Organic light emitting diode (Organic Light Emitting Diode, OLED) is a light-emitting device prepared by using electrons and holes to recombine light in organic thin films. High, with high contrast, pure color, almost no problem of viewing angle; (3) ultra-thin, composed of very thin organic material coating and matrix material, small in size and suitable for portable products; (4) power consumption Very small, environmentally friendly and energy-saving; (5) fast response speed, one thousandth of that of LCD; (6) wide operating temperature range, and can still display normally at -40°C. [0003] Organic electroluminescent materials have continuously achieved breakthroughs in recent years, and have made remarkable progress, posing a str...
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