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Poly-fluorine poly-cyanogen liquid crystal compound as well as preparation method and application thereof

A compound, dicyano technology, applied in the field of polyfluorine and polycyanide liquid crystal compounds and their preparation, can solve the problems of high viscosity, poor optical stability, low resistivity, etc.

Active Publication Date: 2015-04-01
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Among the known liquid crystal compounds, liquid crystal compounds containing cyano substitutions in the lateral direction have large negative dielectric anisotropy and high-definition bright spots, but have disadvantages such as high viscosity, low resistivity, and poor optical stability.

Method used

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  • Poly-fluorine poly-cyanogen liquid crystal compound as well as preparation method and application thereof
  • Poly-fluorine poly-cyanogen liquid crystal compound as well as preparation method and application thereof
  • Poly-fluorine poly-cyanogen liquid crystal compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Example 1, compound 2,3-dicyano-4-(2,3-difluoro-4-n-pentylphenyl)-2',3'-difluoro-4'-n-pentylbiphenyl preparation

[0074] step 1: Synthesis

[0075]

[0076] Put 0.10mol of 2,2,6,6-tetramethylpiperidinyllithium hexane solution into a 250mL reaction bottle, and put 0.05mol of ZnCl into the system at 0°C 2 • TMEDA (catalyst), then kept stirring at 0°C for 20 minutes. Add dropwise 0.05 mol of tetrahydrofuran solution of phthalonitrile represented by formula II to the system, and keep 0° C. for negative ionization reaction for 2 hours after the dropwise addition is completed. Then, 0.15 mol of iodine in tetrahydrofuran solution was added dropwise to the system. After the dropwise addition, iodination reaction was carried out for 1 hour and then reacted at room temperature for 2 hours. After the reaction was completed, 100 mL of saturated sodium thiosulfate solution was added to the system, and after stirring for 20 minutes, 40 mL of ethyl acetate was added, stirred ...

Embodiment 2

[0088] Example 2, compound 2,3-difluoro-4-(2,3-dicyano-4-n-pentyl)phenyl-2',3'-difluoro-4'-n-pentylbiphenyl synthesis

[0089] step 1: Synthesis

[0090] Prepared according to the same steps as in Example 1 step 1) Yield: 65%.

[0091] Step 2: Synthesis

[0092]

[0093] With reference to step 2 of Example 1, the 2,3-difluoro-4-n-pentylphenylboronic acid in step 2 of Example 1 was replaced with n-pentylphenylboronic acid to prepare the compound 1,2-dicyano- 3-n-Pentylbenzene, yield: 76%.

[0094] Step 3: Synthesis

[0095]

[0096] With reference to step 1 of Example 1, the phthalonitrile in step 1 of Example 1 is replaced by the 1,2-dicyano-3-n-pentylbenzene obtained in step 2) of this example, and other operations are carried out with In step 1 of Example 1, the compound 1,2-dicyano-3-iodo-6-n-pentylbenzene was prepared, and the yield was 68%.

[0097] Step 4: Synthesis

[0098] Referring to step 2 of Example 1, replace 1,2-dicyano-3-iodobenzene and 2,...

Embodiment 3

[0103] Embodiment 3, the synthesis of compound 2,3-dicyano-2',3'-difluoro-4,4'-di-n-pentylbiphenyl

[0104]

[0105] In this example, referring to Step 2 of Example 1, 1,2-dicyano-3-iodobenzene and 2,3-difluoro-4-n-pentyl-phenylboronic acid in Step 2 of Example 1 are replaced respectively 2', 3'-difluoro-4'-n-pentyl-2,3-dicyano-4-iodo-biphenyl, n-pentylphenylboronic acid prepared in step 3 of Example 1, other operations The target compound 2,3-dicyano-2',3'-difluoro-4,4'-di-n-pentylbiphenyl was prepared in the same way as in step 2 of Example 1, with a yield of 89%.

[0106] 1 H NMR (CDCl 3 , 300MHz): δ=7.64(s, 2H), 7.07-7.09(d, 2H), 2.91-2.96(t, 2H), 2.68-2.73(t, 2H), 1.36-1.40(m, 9H), 0.88 -0.92 (m, 9H).

[0107] Δn=0.0688, Δε=-2.8.

[0108] As can be seen from the above, the structure of the white solid product is correct, and it is the compound 2,3-dicyano-2',3'-difluoro-4,4'-di-n-pentylbiphenyl shown in formula I

[0109]

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Abstract

The invention discloses a poly- fluorine poly-cyanogen liquid crystal compound as well as a preparation method thereof and application thereof. The structural formula of the poly- fluorine poly-cyanogen liquid crystal compound is shown as formula I. The nuclear magnetic detection for the liquid crystal compounds is correct, and the liquid crystal compounds can be used as liquid crystal monomer which is a liquid crystal display material. The poly- fluorine poly-cyanogen liquid crystal compound is of an important application value, and provided with the FORMULA I.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a polyfluorine and polycyanide liquid crystal compound, a preparation method and application thereof. Background technique [0002] With the continuous development of liquid crystal display technology, people put forward new requirements for the performance of liquid crystal materials. Since it is impossible for any single-component liquid crystal to meet all the requirements of the display, it is necessary to develop monomer liquid crystals with different properties, and then mix various liquid crystal compounds in appropriate proportions in order to obtain the best match of various special parameters to meet the requirements of display. Various display requirements. [0003] Dielectric anisotropy is an important property of liquid crystals. Negative dielectric anisotropy liquid crystals mainly have the following two uses: [0004] (1) In the dynamic scattering (DS) mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/51C07C253/30C09K19/12G02F1/1333H01L51/54
Inventor 郭剑曹建华隋岩华瑞茂
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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