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Organic electroluminescent chromophores containing electron donors and methods for their synthesis

A technology of electron donor and synthesis method, which is applied in the field of organic electro-optic chromophore and its synthesis, can solve the problem that the electro-optic coefficient is not very high, and achieve the goal of improving the macroscopic electro-optic coefficient, increasing the hyperpolarizability, and reducing the electrostatic interaction Effect

Inactive Publication Date: 2015-11-04
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

However, the electro-optic coefficient of most of the organic electro-optic materials is not very high

Method used

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  • Organic electroluminescent chromophores containing electron donors and methods for their synthesis
  • Organic electroluminescent chromophores containing electron donors and methods for their synthesis
  • Organic electroluminescent chromophores containing electron donors and methods for their synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The organic electroluminescent chromophore 1 with the following structure was synthesized:

[0038]

[0039] The synthetic route is as follows:

[0040]

[0041] The synthesis method is:

[0042] 1). Synthesis of compound 2 shown in structural formula 2

[0043] Compound 1, 1.9g n-bromobutane, 0.76g 18-crown-6 and 3g anhydrous K shown in 3.9g structural formula 1 2 CO 3 React in 80ml of DMF solution at 60°C under nitrogen atmosphere for 2 hours; after the reaction is complete, add water to the resulting product, extract with dichloromethane and evaporate dichloromethane, anhydrous MgSO 4 dry. After separation by column chromatography (adsorbent is silica gel), 4.5 g of compound 2 shown in structural formula 2 was obtained;

[0044] 2). Synthesis of compound 3 shown in structural formula 3

[0045] 4.5g of compound 2, 1.1g of sodium hydroxide and 1.9g of isophorone shown in structural formula 2 obtained in step 1) were stirred at room temperature for about 6 ...

Embodiment 2

[0051] The organic electroluminescent chromophore 2 with the following structure was synthesized:

[0052]

[0053] The synthetic route is as follows:

[0054]

[0055] The synthesis method is:

[0056] Basically the same as Example 1, except that the compound 4 shown in structural formula 4 obtained by 0.1 g of Example 1 step 3) and 0.08 g of SF-TCF were refluxed in 1 ml of dehydrated ethanol for 0.5 hours; dehydrated ethanol was evaporated, and column chromatography (The adsorbent is silica gel) and separated to obtain 0.1 g of the organic electroluminescent chromophore 2 product shown in the above structural formula. lambda max (CHCl 3 ):995nm; M + :854; 1 HNMR (CDCl 3 ):δ8.25(br,1H),7.59(d,2H),7.41(d,2H),7.39(s,1H),7.36(m,3H),6.91(d,1H),6.83(d, 1H),6.73(s,1H),6.44(d,1H),6.34(d,1H),3.81(t,2H),3.26(m,4H),2.45(s,2H),2.40(m,2H ),1.86(m,2H),1.73(t,4H),1.56(m,2H),1.42(s,6H),1.30(s,6H),1.03(t,3H),0.99(s,6H) .

Embodiment 3

[0058] The organic electroluminescent chromophore 3 with the following structure was synthesized:

[0059]

[0060] The synthetic route is as follows:

[0061]

[0062]

[0063] The synthesis method is:

[0064] Basically the same as Example 1, except that compound 4 and 0.066g PF-TCF shown in structural formula 4 obtained by 0.1g Example 1 step 3) were refluxed in 1ml dehydrated ethanol for 0.5 hours; steamed dehydrated ethanol, column chromatography (The adsorbent is silica gel) separation to obtain 0.11 g of the organic electroluminescent chromophore 3 product shown in the above structural formula. lambda max (CHCl 3 ):973nm; M + :772; 1 HNMR (CDCl 3 ):δ8.02(br,1H),7.49(m,5H),7.41(s,1H),7.26(d,1H),7.22(d,1H),6.38(d,1H),6.31(s, 1H), 6.26(d, 1H), 3.81(t, 2H), 3.26(m, 4H), 2.45(s, 2H), 2.30(q, 2H), 1.86(m, 2H), 1.72(t, 4H ), 1.56(m,2H), 1.42(s,6H), 1.30(s,6H), 1.02(t,3H), 0.97(s,6H).

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Abstract

The invention relates to the field of organic electro-optical materials and particularly relates to high-performance organic electro-optical chromophores containing electron donors and a synthetic method thereof. The organic electro-optical chromophores containing electron donors can be doped or hooked to a proper polymer material to form electro-optical materials, and are used as core layers for manufacturing electro-optical apparatuses. The high-performance organic electro-optical chromophores containing electron donors disclosed by the invention have the following structural formula which is shown in the specification.

Description

technical field [0001] The invention relates to the field of organic electro-optic materials, in particular to a class of high-performance organic electro-optic chromophores containing electron donors and a synthesis method thereof. Background technique [0002] In the fields of optical communication and optical signal processing, electro-optical conversion is an indispensable technical means. As a key component of electro-optic devices, electro-optic materials play a decisive role in electro-optic conversion. At present, the practical electro-optical materials are mainly inorganic lithium niobate materials. Compared with inorganic materials, organic materials have the advantages of large nonlinear optical coefficient, fast response speed, high optical damage threshold, molecular design according to requirements, easy processing and low cost. Devices made of organic electro-optic materials have low half-wave voltage (less than 1V) and ultra-high bandwidth (expected bandwid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D455/04C09K11/06H01L51/54C08J5/18C08L69/00C08K5/3437
CPCC09K11/06C07D455/04C07F7/1804C08J5/18C08K5/3437C08J2369/00C08L2203/16C08L2203/20C09K2211/1029C09K2211/1092C09K2211/1088H10K85/653H10K85/655H10K85/40H10K85/6572C08L69/00
Inventor 邱玲张茂林甄珍刘新厚许雪蓉
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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