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Organic second-order nonlinear optical chromophore modified by flexible isolating group and preparation method and application thereof

A second-order nonlinear and chromophore technology, which is applied in the field of organic second-order nonlinear optical chromophores and its preparation, can solve the problems of high nonlinear optical coefficients of chromophores, inability to meet device requirements, and small electro-optical coefficients. , to achieve the effects of increasing intermolecular steric hindrance, easy deviceization, and good film-forming properties

Inactive Publication Date: 2019-02-01
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although there are related works on second-order nonlinear optical chromophores, there are not many chromophores with high nonlinear optical coefficients in these works
These chromophores that have been reported so far have large intermolecular interactions in polymers, leading to easy aggregation of molecules, resulting in the conversion of the microscopic first-order molecular hyperpolarizability (β) to the macroscopic material's electro-optic coefficient ( r 33 ) has low efficiency and small electro-optic coefficient, which cannot meet the requirements of deviceization

Method used

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  • Organic second-order nonlinear optical chromophore modified by flexible isolating group and preparation method and application thereof
  • Organic second-order nonlinear optical chromophore modified by flexible isolating group and preparation method and application thereof
  • Organic second-order nonlinear optical chromophore modified by flexible isolating group and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Preparation of an organic second-order nonlinear optical chromophore CL modified by a flexible isolation group. The structure of CL is as follows:

[0072]

[0073] The preparation route is as follows:

[0074]

[0075] Specific steps are as follows:

[0076] 1) Compound 1 was synthesized using the method of Enhanced electro-optic activity from thetriarylaminophenyl-based chromosomes by introducing heteroatoms to the donor.

[0077] Add 1.0mL (11mmol) of phosphorus oxychloride dropwise to 5mL N,N-dimethylformamide (DMF) at 0°C. After stirring for 2 hours, slowly add 3.0g (10.91mmol) of 3- Methoxytriphenylamine in 10 mL of DMF. The reaction temperature was raised to 90 °C and the reaction was stirred for 2 h. After cooling, pour the mixed solution into cold water, and add 1mol / l NaHCO 3 The pH of the solution was adjusted until the solution was neutral, and extracted with ethyl acetate, the combined organic phases were washed with anhydrous MgSO 4 Dry overnigh...

Embodiment 2

[0118] A kind of preparation of polymer film, the method is as follows:

[0119] Add 0.075 grams of amorphous polycarbonate, that is, APC, into 1.00 mL of dibromomethane, stir for 3 to 5 hours until APC is completely dissolved, then add 0.025 grams of the organic second-order nonlinear optical chromophore compound CL synthesized in Example 1 to obtain A mixed solution of organic second-order nonlinear optical chromophore compound and APC, the obtained mixed solution is coated on an ITO glass substrate by spin coating, the control speed is 800-1200 rpm, and then dried in a vacuum at 60°C Dry in the box for 24h to obtain the polymer film I. The thickness of the polarized polymer film is between 2-4 μm.

[0120] Determination of polarization and electro-optic coefficient of the synthesized polymer film

[0121] The obtained polymer film I was subjected to corona polarization, the polarization temperature was 165°C, the polarization time was 10-20min, and the polarization voltag...

Embodiment 3

[0123] A preparation of an organic second-order nonlinear optical chromophore modified by a flexible isolation group, the steps are the same as in Example 1, except that:

[0124] Without step 6, the resulting chromophore molecule would look like this:

[0125]

[0126] Compared with Example 1, the flexible spacer group in the organic second-order nonlinear optical chromophore modified by the flexible spacer group in this example is a hexyl hydroxyl group, and the terminal of this group is a hydroxyl group, although its steric effect is not as good as Large silane endcapping appears to be strong, but opens up the possibility for chromophores to be attached in the polymer backbone or side chains using condensation reactions.

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Abstract

The invention discloses an organic second-order nonlinear optical chromophore modified by a flexible isolating group, It has the following structure described in the description, wherein R1 is an alkyl group of C1 to C20, a hydroxyalkyl group of C1 to C10, a hydroxyalkyl group of C1 to C10 protected by a halogen atom or a hydroxyalkyl group of C1 to C10 protected by a silane; R2 is methyl or trifluoromethyl; R3 is alkyl or phenyl of C1 to C20. The electron donor, the conjugated pi electron bridge and the electron acceptor of the invention are combined to not only well increase the intermolecular steric hindrance, but also inhibit the accumulation between chromophore molecules caused by dipole interaction, improve the intramolecular electron transport ability and effectively improve the conversion of the first-order hyperpolarizability of chromophore molecules to the macroscopic electro-optic coefficients of materials.

Description

technical field [0001] The invention relates to the technical field of organic second-order nonlinear optical materials. More specifically, it relates to an organic second-order nonlinear optical chromophore modified by a flexible isolation group, its preparation method and application. Background technique [0002] With the rapid development of the information age, the requirements for communication and information materials are getting higher and higher at this stage. Since optoelectronics technology can utilize electro-optic and photoelectric conversion and all-optical networks can greatly improve communication efficiency to meet the construction of the information world and fiber-to-the-home plans, nonlinear optical materials have attracted research interest in recent decades, and will It is used in practical fields such as optical communication, optoelectronics and optical information processing. [0003] The integrated optical system has the advantages of small size,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/06C07F7/18C08K5/45C08L69/00G02F1/361
CPCC07D409/06C07F7/1892C08J5/18C08J2369/00C08K5/45G02F1/361C08L69/00
Inventor 甄珍陈璐和延岭薄淑晖
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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