A kind of compound with d-π-a structure and its preparation method and application

A technology of compound and synthesis method, which is applied in the field of preparation of organic second-order nonlinear chromophores, can solve the problems that electronic bridges have not been reported to be used, and achieve the effects of convenient device process, high product yield, and widespread production

Active Publication Date: 2019-03-15
江苏佰欧翌科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indacene derivatives are widely used as important building groups in the field of organic photovoltaic materials, but their use as electronic bridges in the field of organic nonlinear optics has not been reported yet.

Method used

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  • A kind of compound with d-π-a structure and its preparation method and application
  • A kind of compound with d-π-a structure and its preparation method and application
  • A kind of compound with d-π-a structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] An organic second-order nonlinear chromophore with D-π-A structure based on indacene derivatives was synthesized as shown below:

[0084]

[0085] The synthetic route is as follows:

[0086]

[0087] 1) Synthesis of compound 2

[0088] 44 mg of phosphine salt (0.092 mmol) and 100 mg of indacene derivative (compound 1, 0.093 mmol) were dissolved in 1,2-dichloroethane solvent, and 10 mg of sodium hydride (0.42 mmol) was slowly added at 0°C. Stir at room temperature for 24 hours, pour the reaction product into water, separate the layers, extract the aqueous phase with dichloromethane, combine the organic phases, dry the organic phase with anhydrous magnesium sulfate, filter, and remove the dichloromethane by rotary evaporation to obtain a crude product. Column chromatography (stationary phase is 200-300 mesh silica gel, mobile phase is a mixture of petroleum ether and ethyl acetate, petroleum ether: ethyl acetate = 3:1) to obtain 70 mg of yellow powder with a yield ...

Embodiment 2

[0096] An organic second-order nonlinear chromophore with D-π-A structure based on indacene derivatives was synthesized as shown below:

[0097]

[0098] The synthetic route is as follows:

[0099] 1) Synthesis of compound 2-2

[0100] 63 mg of phosphine salt (0.103 mmol) and 100 mg of indacene derivative (compound 1-2, 0.104 mmol) were dissolved in 1,2-dichloroethane solvent, and 11 mg of sodium hydride (0.46 mmol) was slowly added at 0°C. Stir at room temperature for 24 hours, pour the reaction product into water, separate the layers, extract the aqueous phase with dichloromethane, combine the organic phases, dry the organic phase with anhydrous magnesium sulfate, filter, and remove the dichloromethane by rotary evaporation to obtain a crude product. Column chromatography (stationary phase is 200~300 mesh silica gel, mobile phase is a mixture of petroleum ether and ethyl acetate, petroleum ether: ethyl acetate = 3:1), and 85 mg of powdery compound 3 is obtained with a ...

Embodiment 3

[0106] An organic second-order nonlinear chromophore with D-π-A structure based on indacene derivatives was synthesized as shown below:

[0107]

[0108] The synthetic route is as follows:

[0109]

[0110] 1) Synthesis of compound 2-3

[0111] 55 mg of phosphine salt (0.083 mmol) and 100 mg of indacene derivative (compound 1-3, 0.084 mmol) were dissolved in 1,2-dichloroethane solvent, and 9 mg of sodium hydride (0.375 mmol) was slowly added at 0°C. Stir at room temperature for 24 hours, pour the reaction product into water, separate the layers, extract the aqueous phase with dichloromethane, combine the organic phases, dry the organic phase with anhydrous magnesium sulfate, filter, and remove the dichloromethane by rotary evaporation to obtain a crude product. Column chromatography (stationary phase is 200-300 mesh silica gel, mobile phase is a mixture of petroleum ether and ethyl acetate, petroleum ether: ethyl acetate = 3:1) to obtain 76 mg of yellow powder with a yiel...

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Abstract

The invention relates to a compound having a D-pi-A structure as well as a preparation method and application of the compound. The method uses an indacene derivative as a pi-conjugated electron bridge, and introduces an electron-donating group and an electron-withdrawing group at two ends of the derivative to prepare the nonlinear optical chromophore having the D-pi-A structure. The longer conjugation length of the chromophore makes the chromophore have larger first-order hyperpolarizability (beta), so that high-performance organic electrooptical materials can be prepared. The chromophore provided by the invention has a larger molecular weight, in addition to be doped with a polymer to prepare a film, the chromophore can be directly dissolved by using an organic solvent and used to preparea film through spin coating, and the chromophore provides great convenience for a componentization process; and the chromophore provided by the invention also has a higher thermal decomposition temperature and glass transition temperature, so that nonlinear optical chromophore molecules have extremely good orientation stability in materials, and meet requirements for componentization to a large extent.

Description

technical field [0001] The invention relates to the field of organic second-order nonlinear optical materials, in particular to an organic second-order nonlinear chromophore with D-π-A structure based on indacene derivatives with higher thermal decomposition temperature and orientation stability preparation methods and applications. Background technique [0002] As the important material basis of laser technology and communication technology, nonlinear optical materials have become a hot spot in current technology research. Nonlinear optical materials have important applications in the fields of optical information processing, high-speed optical communication, optoelectronics and integrated circuits. As we all know, the switching speed of photons is several orders of magnitude faster than that of electronic processes, so working at optical frequencies can greatly increase the bandwidth of information processing, and the use of harmonic generation, parametric oscillation and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C07D495/04C07D519/00C09K11/06G02F1/361
CPCC07D495/04C07D495/22C07D519/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088C09K2211/1092G02F1/3614
Inventor 邓国伟赵紫羽周召琼李秉轲杨敏张小玲孙康李仲辉
Owner 江苏佰欧翌科技有限公司
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