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Liquid crystal compound, liquid crystal composition, polymer and application

A technology for liquid crystal compositions and compounds, applied in the fields of liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of long synthesis path, incompatibility, and thickening of optically anisotropic layer thickness.

Active Publication Date: 2016-03-09
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such a laminate has the following problems: two retardation layers are required, and the angle of anisotropy of the two retardation layers needs to be adjusted, etc., the complexity of manufacturing for forming the laminate, and the optical parameters The film thickness of the anisotropic layer becomes thicker, etc.
[0011] However, since the compound described in Patent Document 6 has low refractive index anisotropy, it is necessary to increase the film thickness in order to obtain a desired retardation, and there are also concerns about the following problems: it is difficult to control the orientation uniformity due to the small aspect ratio, and further, Difficult to manufacture due to long synthesis path, etc.
The compounds described in Patent Document 7 and Patent Document 8 have absorption in the visible region, so they tend to cause a decrease in transmittance or color spots, and are not suitable for use in optical applications.
The compounds described in Patent Document 9 and Patent Document 10 are relatively good in terms of optical properties and production processes, but further improvement in properties is required in terms of mechanical strength of the polymer, adhesion to the substrate, heat resistance, etc.

Method used

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  • Liquid crystal compound, liquid crystal composition, polymer and application
  • Liquid crystal compound, liquid crystal composition, polymer and application
  • Liquid crystal compound, liquid crystal composition, polymer and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0302] [Example 1] The compound (1-1-2-1) shown below was synthesized in the following manner.

[0303] [chem 38]

[0304]

[0305] Compound (ex-1) was synthesized according to "Heterocyclic communications" 8, 2, 135 (2002).

[0306] 16.0 g of compound (ex-1) was added to 160 mL of ethanol, and stirred at 10° C. or lower under a nitrogen atmosphere. 5.3 g of sodium borohydride was added thereto. Then, the mixture was stirred at below 10°C for 3 hours. 160 mL of 1N hydrochloric acid water was added to the reaction liquid, and then 160 mL of water was added. The precipitate was separated by filtration and washed with a large amount of water to obtain 15.5 g of compound (ex-2).

[0307] 5.0 g of compound (ex-2), 9.3 g of 4-pentylcyclohexanecarboxylic acid, and 1.1 g of 4-dimethylaminopyridine (4-dimethylaminopyridine, DMAP) were added to 90 ml of dichloromethane , stirring while cooling under a nitrogen atmosphere. 20 mL of a dichloromethane solution of 9.7 g of 1,3-dicy...

Embodiment 2

[0312] Compound (1-1-19-1) shown below was synthesized in the following manner.

[0313] [chem 39]

[0314]

[0315] Compound (ex-3) was synthesized according to "Heterocyclic communications." 8, 2, 135 (2002).

[0316] 5.0 g of compound (ex-3), 2.0 g of phenol, and 0.5 g of DMAP were added to 50 mL of dichloromethane, and stirred while cooling under a nitrogen atmosphere. 10 mL of a dichloromethane solution of 4.5 g of DCC was added dropwise thereto. After the dropwise addition, it was stirred at room temperature for 16 hours. The deposited precipitate was separated by filtration, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. Dichloromethane was distilled off under reduced pressure, the residue was purified by column chromatography (silica gel, eluent: toluene), and recrystallized in methanol to obtain 4.8 g of the compound (ex- 4).

[0317] 4.8 g of compound (ex-4) was added to 150 mL of acetonitrile (MeCN), and stirred at ro...

Embodiment 3

[0324] Compound (1-1-7-1) shown below was synthesized in the following manner.

[0325] [chemical 40]

[0326]

[0327]Compound (ex-7) was synthesized according to "Heterocyclic communications." 8, 2, 135 (2002).

[0328] Add 5.0 g of compound (ex-7), 3.2 g of benzyl mercaptan, and 2.9 g of potassium hydroxide to 50 ml of N, N-dimethylformamide (dimethylformamide, DMF), under nitrogen atmosphere , 100 degreeC, heating and stirring for 4 hours. Water was poured into the reaction solution, and the precipitate was separated by filtration and washed with water and methanol. The obtained crystals were recrystallized from a mixed solution of toluene and methanol to obtain 3.5 g of compound (ex-8).

[0329] 3.0 g of compound (ex-8) was added to 90 mL of acetonitrile (MeCN), and stirred at room temperature under a nitrogen atmosphere. 18 mL of an aqueous solution of 12.8 g of CAN was added dropwise thereto. After the dropwise addition, the mixture was stirred at room temperatu...

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Abstract

The invention a liquid crystal compound, a liquid crystal composition and a polymer and application which can suppress refractive index anisotropism due to wave lengths, display low wavelength dispersion characteristics and further display inverse wavelength dispersion. The invention discloses the compound expressed by the formula (1) and the liquid crystal composition containing the compound.

Description

technical field [0001] The invention relates to a liquid crystal compound having a benzothiophene, benzofuran or indole structure, a liquid crystal composition, a polymer and applications thereof. Background technique [0002] In recent years, liquid crystal compounds having a polymerizable group have been utilized in optically anisotropic films showing birefringence (optical anisotropy), such as reflective polarizers and retardation plates. This compound exhibits birefringence in a liquid crystal state, and by polymerization, its orientation is fixed. The fixed orientation state of the polymer includes homogeneous (horizontal orientation), tilt (tilt orientation), homeotropic (vertical orientation), and twist (twisted orientation). [0003] Optically anisotropic films with parallel orientation can be used as composite retardation plates, circular polarizing plates, for example, by combining with 1 / 2 wavelength plates, 1 / 4 wavelength plates, or films with other optical func...

Claims

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Application Information

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IPC IPC(8): C07D333/70C07D333/54C07D417/04C07D333/60C07D413/04C09K19/34C09K19/46C08F222/20C08F220/30G02B5/30
CPCC07D333/54C07D333/60C07D333/70C07D413/04C07D417/04C08F220/30C08F220/305C08F222/20C08F222/205C09K19/3491C09K19/3497C09K19/46G02B5/30
Inventor 大槻大辅奈良和美
Owner JNC CORP
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