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Thiophthene high birefringence liquid crystal compound and composition thereof

A technology of liquid crystal compounds and liquid crystal compositions, which is applied in the direction of liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve problems such as difficult to meet application requirements and low birefringence, and achieve increased optical anisotropy and high birefringence The effect of high rate and wide liquid crystal phase range

Active Publication Date: 2017-03-22
XIAN MODERN CHEM RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biphenyl compound (4) and the tolan compound (5) have low birefringence, and it is difficult to meet their application requirements in liquid crystal optical devices

Method used

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  • Thiophthene high birefringence liquid crystal compound and composition thereof
  • Thiophthene high birefringence liquid crystal compound and composition thereof
  • Thiophthene high birefringence liquid crystal compound and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Synthesis of 2-(3,5-difluoro-4-isothiocyanatophenyl)-5-pentylthieno[3,2-b]thiophene:

[0057] The specific structural formula is as follows:

[0058]

[0059] The preparation process is as follows:

[0060] (1) Step 1: Synthesis of 1-(thieno[3,2-b]thiophen-2-yl)pentyl-1-one

[0061]

[0062] Add thieno[3,2-b]thiophene (100.0 g, 0.713 mol) and 1 L of dichloromethane into a 2 L three-necked flask equipped with mechanical stirring and a constant pressure dropping funnel, stir and dissolve thoroughly, and then start to drop at room temperature Add n-pentanoyl chloride (130.6g, 1.084mol), add anhydrous aluminum trichloride (142.6g, 1.70mol) in batches after dripping, after continuing to react for 2h, TLC monitors the reaction, after the reaction finishes, quench with ice-water mixture The reaction was quenched, extracted with dichloromethane, washed with saturated sodium bicarbonate solution, washed with water until neutral, dried over anhydrous magnesium ...

Embodiment 2

[0078] Example 2: Synthesis of 2-(3-fluoro-4-isothiocyanatophenyl)-5-pentylthieno[3,2-b]thiophene:

[0079]

[0080] Using 2-fluoro-4-iodoaniline to replace 2,6-difluoro-4-iodoaniline in step (4) of Example 1, the same method is used to synthesize 2-(3-fluoro-4-isothiocyanatobenzene base)-5-pentylthieno[3,2-b]thiophene.

[0081] Structure Identification: 1 H NMR (δ, CDCl 3 ): 7.411(s, 1H), 7.355~7.381(dd, 1H, J 1 = 2Hz,J 2 = 11Hz), 7.317 ~ 7.338 (dd, 1H, J 1 = 2Hz,J 2=8.5Hz), 7.163~7.195(t, 1H, J=8Hz), 6.945(s, 1H), 2.870~2.900(t, 2H, J=7.5Hz), 1.678~1.760(m, 2H), 1.342~ 1.410 (m, 4H), 0.896~0.925 (t, 3H, J=7Hz). MS (50eV) m / z (%): 360.9(43), 303.9(100), 271.9(7).

[0082] The above structural identification data show that the synthesized compound is indeed 2-(3-fluoro-4-isothiocyanatophenyl)-5-pentylthieno[3,2-b]thiophene.

[0083] The liquid crystal phase transition characteristic temperature was measured by DSC at a heating rate of 5°C / min, and the result was: C...

Embodiment 3

[0084] Example 3: Synthesis of 2-(3,5-difluoro-4-isothiocyanatophenyl)-5-butylthieno[3,2-b]thiophene:

[0085]

[0086] Butyryl chloride was used to replace valeryl chloride in step (1) of Example 1, and 2,6-difluoro-4-iodoaniline was used as a raw material to synthesize 2-(3,5-difluoro-4 -isothiocyanatophenyl)-5-butylthieno[3,2-b]thiophene.

[0087] Structure Identification: 1 H NMR (δ, CDCl 3 ): 7.411(s, 1H), 7.153~7.191(m, 2H), 6.947(s, 1H), 2.881~2.911(t, 2H, J=7.5Hz), 1.683~1.743(m, 2H), 1.389~ 1.464 (m, 2H), 0.940~0.969 (t, 3H, J=7.5Hz). MS (50 eV) m / z (%): 365.0 (49), 322.0 (100), 289.9 (8).

[0088] The above structural identification data show that the synthesized compound is indeed 2-(3,5-difluoro-4-isothiocyanatophenyl)-5-butylthieno[3,2-b]thiophene.

[0089] Using DSC to test the characteristic temperature of liquid crystal phase transition at a heating rate of 5°C / min, the result is: Cr73.53S A 124.68N129.02I. The monomer was dissolved in the basic formu...

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PUM

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Abstract

The invention discloses a liquid crystal compound comprising a thieno[3,2-b] thiophene ring and a composition thereof. The structural general formula of the liquid crystal compound is as shown in a formula (1) in the description, wherein R represents alkyl, alkoxyl or alkenyl, the carbon number of which is 1-9; Z represents any one of a single bond, an olefinic bond, an acetylenic bond, an ester bond and a difluoromethyl ether bond; and (F)x represents fluorine atom substitution in any position on a benzene ring, x represents the substituting number of f fluorine atoms and the value of x is 0-4. The compound disclosed by the invention has relatively high birefringence and can be applied to the field of liquid crystal light modulators.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and in particular relates to a thieno[3,2-b]thiophene liquid crystal compound and a composition thereof, which are mainly used in liquid crystal light modulation devices. Background technique [0002] While liquid crystal materials are widely used in the display field, they can also be used in other fields, such as liquid crystal optical devices such as optical modulators, variable focus lenses, and infrared scene generators. In these optical applications, the response speed of liquid crystal devices is required to be high, and faster response speed means better system performance and optical effects. Studies have shown that the use of liquid crystal materials with high birefringence is beneficial to reduce the cell thickness of liquid crystal devices, thereby effectively improving the response speed. Therefore, the development of high birefringence liquid crystal materials has ...

Claims

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Application Information

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IPC IPC(8): C07D495/04C09K19/34C09K19/44
CPCC07D495/04C09K19/3491C09K19/44C09K2019/0414
Inventor 安忠维杨晓哲莫玲超李建李娟利胡明刚杨志车昭毅
Owner XIAN MODERN CHEM RES INST
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