High-birefringence liquid crystal compound, and preparation method and composition thereof

A liquid crystal compound and liquid crystal composition technology, applied in chemical instruments and methods, liquid crystal materials, etc., can solve problems such as crystallization, and achieve the effects of low raw material cost, low melting enthalpy, and short synthesis steps

Active Publication Date: 2017-07-25
XIAN MODERN CHEM RES INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Adding the above liquid crystal compounds to the formula will easily lead to crystallization at low temperature

Method used

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  • High-birefringence liquid crystal compound, and preparation method and composition thereof
  • High-birefringence liquid crystal compound, and preparation method and composition thereof
  • High-birefringence liquid crystal compound, and preparation method and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of 4-((4-propenyloxy)phenyl)ethynyl)-2-fluoro-1-isothiocyanatobenzene:

[0048] The specific structure is as follows:

[0049]

[0050] The preparation process is as follows:

[0051] Step 1: Synthesis of 1-(propenyloxy)-4-iodobenzene

[0052]

[0053] Under nitrogen protection, p-iodophenol (176.08g, 0.8mol), 3-bromo-1-propene (145.2g, 1.2mol), K 2 CO 3 (221g, 1.6mol), ethanol 800mL. Turn on heating and stirring, stop stirring after reflux reaction for 2 hours, and naturally cool down to room temperature for aftertreatment. Filter out the insoluble matter, spin evaporate ethanol, add n-heptane to dissolve the organic matter, wash with water until neutral, dry over anhydrous magnesium sulfate, filter, spin the filtrate to dryness, and go through column chromatography, elute with n-heptane, eluent After the solvent was removed by rotary evaporation, 201 g of colorless liquid was obtained, which was the intermediate 1-(propenyloxy)-4-iodobenzene. GC ...

Embodiment 2

[0073] Synthesis of 4-((4-(2,2-difluorovinyl)phenyl)ethynyl)-2-fluoro-isothiocyanatobenzene:

[0074]

[0075] Using 4-iodoaniline instead of 2-fluoro-4-iodoaniline in step (4) of Example 1, the same method as in Example 1 was used to synthesize 1-(propenyloxy)-4-((4-isosulfur cyanophenyl)ethynyl)benzene.

[0076] Structure Identification:

[0077] 1 H-NMR (δ, CDCl 3 ):4.552-4.568(m,2H),5.296-5.320(m,1H),5.434-5.443(m,1H),6.013-6.090(m,1H),6.879-6.908(m,2H),7.170-7.192 (m,2H),7.433-7.482(m,4H); MS(70eV)m / z(%):290.9(M + ,63), 221.9.0(19), 189.9(8), 162.9(17), 149.9(100).

[0078] The above structural identification data show that the synthesized compound is indeed 1-(propenyloxy)-4-((4-isothiocyanatophenyl)ethynyl)benzene.

[0079] Use DSC to test the liquid crystal phase transition temperature of 1-(propenyloxy)-4-((4-isothiocyanatophenyl)ethynyl)benzene at a temperature of 3°C / min. The result is: Cr 104.8I, melting The enthalpy value is 21.35 kJ / mol. The monomeric ...

Embodiment 3

[0084] Synthesis of 1-((4-(propenyloxy)phenyl)ethynyl)-2-fluoro-4-isothiocyanatobenzene:

[0085]

[0086] Using 3-fluoro-4-iodoaniline instead of 2-fluoro-4-iodoaniline in step (4) of Example 1, the same method as in Example 1 is used to synthesize 1-((4-(propenyloxy)benzene (yl)ethynyl)-2-fluoro-4-isothiocyanatobenzene.

[0087] Structure Identification:

[0088] 1 H-NMR (δ, CDCl 3 ): 4.555-4.571(m,2H),5.297-5.321(q,1H),5.403-5.440(q,1H),6.012-6.089(m,1H),6.884-6.912(m,2H),6.953-7.007 (m,2H),7.437-7.487(m,3H); MS(70eV)m / z(%):308.9(M + ,66),267.9(100),239.9(22),207.9(8),182(16),156(2).

[0089] The above structural identification data show that the synthesized compound is indeed 1-((4-(propenyloxy)phenyl)ethynyl)-2-fluoro-4-isothiocyanatobenzene.

[0090] Use DSC to test the liquid crystal phase transition temperature of 1-((4-(propenyloxy)phenyl)ethynyl)-2-fluoro-4-isothiocyanatobenzene at a temperature of 3°C / min. The result is: Cr 66.35 N 81.35 I, the melting poi...

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Abstract

The invention discloses a high-birefringence liquid crystal compound, a preparation method of the high-birefringence liquid crystal compound and a composition containing the high-birefringence liquid crystal compound. The liquid crystal compound has a structure general formula (I) shown in the description, wherein X1, X2 and X3 is H or F; R is one of straight-chain alkenyl with a carbon atom number being 2 to 5 or fluoro alkenyl with a carbon atom number being 2 to 5. The liquid crystal compound comprises less than or equal to 40 percent (not zero) of compounds shown as the general formula (I), 1 to 40 percent of compounds shown as a general formula (II), 1 to 30 percent of compounds shown as a general formula (III) and 2 to 50 percent of compounds shown as a general formula (IV), wherein the general formulas are shown in the description; R1, R2 and R3 are respectively one of alkyl with a carbon atom number being 1 to 7, alkoxyl with a carbon atom number being 1 to 7 or fluoroalkyl with a carbon atom number being 1 to 5; X4 to X9 are respectively -H or -F. The high-birefringence liquid crystal compound has the advantages of high birefringence and low rotary viscosity, and is applicable to the fields such as space light modulators, laser detectors and 3D (3-dimensional) displays.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and specifically relates to a liquid crystal compound with high birefringence and a composition thereof, which are mainly applicable to laser detectors, spatial light modulators, variable focus liquid crystal lenses, phase modulators in microwave and THz fields, and 3D display fields etc. Background technique [0002] In recent years, the application of liquid crystal materials with high birefringence in new liquid crystal optical devices such as laser detectors, spatial light modulators, liquid crystal gratings, and variable-focus liquid crystal lenses, as well as in 3D display and holographic technologies has attracted much attention. The application of liquid crystal optical devices requires a certain amount of phase modulation (Δnd≥1λ). If the liquid crystal material has a sufficiently large birefringence, that is, the value of Δn, optical components with a smaller thickness ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/18C09K19/44
CPCC09K19/18C09K19/44C09K2019/181
Inventor 安忠维李娟利彭增辉李建胡明刚张璐车昭毅杨志莫玲超杨晓哲
Owner XIAN MODERN CHEM RES INST
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