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Triphenylethylene compound containing cyanogen and preparation method thereof

A technology of triphenylene and compound, applied in the field of cyano group-containing triphenylene compound and preparation thereof, can solve the problems of weak photoluminescence, decreased luminous efficiency, increased luminous intensity and the like, achieves wide sources and easy control of synthesis conditions Effect

Inactive Publication Date: 2010-07-21
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing organic light-emitting materials face a bottleneck problem. In high-concentration solutions or in the solid state, the molecules of organic light-emitting materials present a close-packed H-aggregation (face-to-face), and the strong interaction between molecules tends to lead to strong non- Radiative attenuation, resulting in an order of magnitude decrease in the luminous efficiency of its solid or aggregated state compared to its low-concentration dilute solution
In 2001, Tang Benzhong (Chem. Commmun., 2001, 1740) accidentally discovered that the photoluminescence of siloles was extremely weak in dilute solution, but the luminescence intensity increased in solid powder or thin film (aggregation- induced emission enhancement, AIEE)

Method used

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  • Triphenylethylene compound containing cyanogen and preparation method thereof
  • Triphenylethylene compound containing cyanogen and preparation method thereof
  • Triphenylethylene compound containing cyanogen and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 The preparation of cyanotriphenylethylene compound I-1

[0029]

[0030] Step one 4, the synthesis of 4'-two (diphenylamino) benzophenone intermediates: in a four-necked reaction flask equipped with a stirrer, add 30 milliliters of hexamethylphosphoramide, 8.5 grams (0.05 moles) of diphenhydramine Aniline and 0.052 moles of sodium tert-butoxide, stirred to disperse evenly, N 2 Under protection, heat up at 60-80°C and keep it warm for 2 hours to remove tert-butanol. Thereafter, 4.4 g (0.02 mol) of 4,4'-difluorobenzophenone was added in batches, and the reaction was completed at 100-130° C. for 6 hours. Cool the reaction product system to room temperature, add ethanol, stand for crystallization, filter, use ethanol / acetone (volume ratio V / V=3 / 7) mixed solvent to recrystallize the filter cake, and vacuum dry to obtain 11.75 grams of yellow 4,4 '-Bis(diphenylamino)benzophenone intermediate, the yield is 91.7%, and the melting point is 173-175°C. Elemental...

Embodiment 2

[0032] The preparation of embodiment 2 cyano-triphenylethylene compounds I-2

[0033]

[0034] According to the preparation method and operating procedure of Example 1, the raw material 2,5-dimethoxy-1,4-benzenediacetonitrile in Step 2 in Example 1 was replaced with 2-methoxy-5-n-butoxy- 1,4-benzenediacetonitrile, the bright green cyano-triphenylethylene compound I-2 of the present invention can be obtained. Tg121°C was measured by TGA method, and Td450°C was measured by DSC method. Its concentration is 4.5×10 -5 The mol / L xylene solution has an ultraviolet-visible spectrum characteristic peak λmax=402nm, and a fluorescence spectrum characteristic peak λmax=494nm with an excitation wavelength of 400nm.

Embodiment 3

[0035] The preparation of embodiment 3 cyano-triphenylethylene compounds I-3

[0036]

[0037] According to the preparation method and operation procedure of Example 1, the raw material 2,5-dimethoxy-1,4-benzenediacetonitrile in Step 2 of Example 1 was replaced with 2,5-di-neopentyloxy-1,4- Phenyldiacetonitrile, the bright green cyanotriphenylethylene compound I-3 of the present invention can be obtained. Tg102°C was measured by TGA method, and Td435°C was measured by DSC method. Its concentration is 4.5×10 -5 The mol / L xylene solution has an ultraviolet-visible spectrum characteristic peak λmax=401nm, and a fluorescence spectrum characteristic peak λmax=496nm with an excitation wavelength of 400nm.

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Abstract

The invention provides a triphenylethylene compound containing cyanogen. An electron repulsive group comprising bis-phenylamino and alkoxy and an electron withdrawing group comprising the cyanogen are led to a triphenyl ethane conjugated system to form to two electron transfer channels opposite to each other. The triphenylethylene compound provided by the invention has obvious intramolecular charge transfer property. Due to the influence of the three phenyl, four bis-phenylamino and two alkoxyl steric clashes in the triphenylethylene compound, the molecular space structure of the triphenylethylene compound containing the cyanogen provided by the invention is of a curved petal shape of orchid, and having gathered auxoflorence property.

Description

technical field [0001] The invention belongs to the field of organic photoelectric functional materials. The invention particularly relates to a cyanotriphenylethylene compound and a preparation method thereof. technical background [0002] The scientific and technological circles and industrial circles in some developed countries have attached great importance to organic photoelectric light-emitting devices (OLED / PLED) made of conjugated organic small molecules or polymer macromolecules, because OLED / PLED has low manufacturing cost, rich color and high brightness. , flexible display and many other features. However, the existing organic light-emitting materials face a bottleneck problem. In high-concentration solutions or in solid state, the molecules of organic light-emitting materials present H-aggregation (face-to-face) close packing, and the strong interaction between molecules tends to lead to strong non- Radiation attenuation causes the luminous efficiency of its so...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/43C07C253/30C09K11/06
Inventor 刘霖张田林童志伟金川刘琦刘桂英黄芽刘攀攀邱龑
Owner HUAIHAI INST OF TECH
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