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Liquid crystal compound with high birefringence and wide nematic phase temperature interval and composition comprising liquid crystal compound

A technology for liquid crystal compounds and liquid crystal compositions, applied in the fields of organic chemistry, liquid crystal materials, chemical instruments and methods, etc., can solve the problems of inducing smectic phase, poor compatibility, easy to appear crystallization phenomenon, etc., and achieve wide nematic phase. Temperature range, effect of high birefringence

Active Publication Date: 2015-01-07
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The reported phase transition temperature is: C 102S A 208N 259.8I, Δε=17.8, Δn=0.497, its melting point is greater than 100°C, and the temperature range of smectic phase is as wide as 106°C. It has poor compatibility in mixed liquid crystals, and is prone to crystallization and induced smectic phase.

Method used

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  • Liquid crystal compound with high birefringence and wide nematic phase temperature interval and composition comprising liquid crystal compound
  • Liquid crystal compound with high birefringence and wide nematic phase temperature interval and composition comprising liquid crystal compound
  • Liquid crystal compound with high birefringence and wide nematic phase temperature interval and composition comprising liquid crystal compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of 4'-((4-ethylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate-1,1'-biphenyl:

[0027] The specific structural formula is as follows:

[0028]

[0029] The preparation process is as follows:

[0030] (1) Under nitrogen protection, add 13.1g (98mmol) of p-bromoiodobenzene, 100mL of tetrahydrofuran, 31.5mL of triethylamine (0.2mol), PdCl 2 (PPh 3 ) 2 0.7g (0.001mol), CuI 0.6g (0.003mol). Then, 27.6 g (98 mmol) of p-ethylphenylacetylene and 50 mL of tetrahydrofuran were added to the constant pressure dropping funnel. Nitrogen was replaced three times, the temperature of the system was lowered to -5°C to 0°C, and a tetrahydrofuran solution of ethylphenylacetylene was added dropwise. After the dropwise addition was completed, it was raised to room temperature and stirred overnight. The reaction solution was filtered to remove a large amount of salt. The filtrate was spin-dried and passed through a silica gel column with n-heptane. Rotate the liquid throu...

Embodiment 2

[0038] Using propylphenylacetylene instead of ethylphenylacetylene in Example 1, the same method was used to synthesize 4'-((4-propylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate Ester-1,1′-biphenyl. Structure Identification:

[0039] 1 H NMR (δ, CDCl 3): 0.914~0.963(t, 3H), 1.579~1.703(m, 2H), 2.567~2.617(t, 2H), 7.135~7.163(d, J=14Hz, 4H), 7.416~7.459(m, 4H) , 7.536~7.564 (d, J=14Hz, 2H). IR (KBr, cm -1 ): 3028 (w, Ar-H), 2960, 2870 (m, -CH 3 ), 2929 (w, -CH 2 ), 2218 (w, c≡c), 2035 (s, NCS), 1623, 1547, 1508 (m, Ar), 1438, 1206, 1113, 1042, 945, 831.

[0040] The above structural identification data show that the synthesized compound is indeed 4′-((4-propylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate-1,1′-biphenyl .

[0041] 4'-((4-Propylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanato-1,1'-biphenyl was tested by DSC at a temperature increase of 5°C / min The liquid crystal phase transition temperature, the result is: C 90.30N 233.76I, melting enthalpy value 21.47KJ·m...

Embodiment 3

[0043] Using butylphenylacetylene instead of ethylphenylacetylene in Example 1, the same method was used to synthesize 4'-((4-butylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate Ester-1,1′-biphenyl. Structure Identification:

[0044] 1 H NMR (δ, CDCl 3 ): 0.895~0.943(t, 3H), 1.255~1.377(m, 2H), 1.485~1.628(t, 2H), 2.568~2.619(t, 2H), 7.065~7.187(m, 4H), 7.368~7.394 (m, 4H), 7.483-7.510 (m, 2H). IR (KBr, cm -1 ): 3026 (w, Ar-H), 2960, 2858 (m, -CH 3 ), 2925 (w, -CH 2 ), 2211 (w, c≡c), 2051 (s, NCS), 1623, 1550, 1507 (m, Ar), 1441, 1204, 1113, 1042, 943, 830.

[0045] The above structural identification data show that the synthesized compound is indeed 4′-((4-butylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate-1,1′-biphenyl .

[0046] 4'-((4-butylphenyl)ethynyl)-3,5-difluoro-4-isothiocyanate-1,1'-biphenyl was tested by DSC at a temperature increase of 5°C / min The liquid crystal phase transition temperature, the result is: C 68.08N 232.92I, and the nematic phase temperatu...

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Abstract

The invention discloses a liquid crystal compound with a high birefringence and a wide nematic phase temperature interval and a liquid crystal composition comprising the liquid crystal compound. The structure of the liquid crystal compound is shown in a general formula I in the Specification. The liquid crystal composition comprises a compound shown as the general formula I, 5-75 percent of a compound shown as a general formula II, 5-25 percent of a compound shown as a general formula III and 5-60 percent of a compound shown as a general formula IV, wherein the content of the compound shown as the general formula I is less than or equal to 55 percent and is not zero. The liquid crystal compound has the advantages of low melting point, high clearing point, high birefringence and high low-temperature intermiscibility. The liquid crystal composition comprising the liquid crystal compound has the wide nematic phase temperature interval and the high birefringence, and is applicable to the fields of 3D (three-dimensional) displays, optical phase modulators, infrared detectors and the like. In the general formulae I, II, III and IV, R1 to R4 are straight-chain paraffin of which the carbon number is 1-9, X1 to X9 are -F or -H, and at least one of the X1 to the X9 is -F.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and in particular relates to a liquid crystal compound with toluene phenyl isothiocyanate and a composition thereof, which are mainly used in the fields of 3D display, optical phase modulator, infrared laser detector and the like. Background technique [0002] Liquid crystal materials with high birefringence play a very important role in applications such as laser detectors, zoom lenses, reflective displays, cholesteric liquid crystal lasers, dynamic infrared scene projectors, and tunable optical attenuators. The physical properties of liquid crystal materials are closely related and mutually restricted. According to the liquid crystal response time formula τ off = γ 1 d 2 / K 11 π 2 , to increase the response speed, it is necessary to reduce the rotational viscosity γ 1 1. Reduce the thickness d of the liquid crystal cell, and from the calculation formula of the optical phas...

Claims

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Application Information

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IPC IPC(8): C09K19/18C09K19/44C07C331/28
Inventor 安忠维李娟利李建莫玲超杨晓哲车昭毅胡明刚杨志张璐武斌
Owner XIAN MODERN CHEM RES INST
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