Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element
A liquid crystal compound and liquid crystal composition technology, applied in optics, liquid crystal materials, nonlinear optics, etc., can solve the problems of lower operating voltage, unrecognizable compound characteristics, unreminiscent compounds, etc.
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[0322] The resulting compound is obtained by 1 The identification is performed by nuclear magnetic resonance spectrum obtained by H-NMR analysis, gas chromatogram obtained by gas chromatography (gas chromatography, GC) analysis, etc., so the analysis method will be described first.
[0323] 1 H-NMR analysis: DRX-500 (manufactured by Bruker BioSpin Co., Ltd.) was used as a measurement device. Dissolve the samples prepared in Examples etc. in CDCl 3 In the deuterated solvent in which the sample is soluble, the measurement is carried out at room temperature, 500 MHz, and the cumulative number of times is 24. In addition, in the description of the obtained nuclear magnetic resonance spectrum, s represents a singlet, d represents a doublet, t represents a triplet, q represents a quartet, and m represents a multiplet. Furthermore, tetramethylsilane (TMS) was used as a zero-point standard substance for the chemical shift 6 value.
[0324] GC analysis: A GC-14B gas chromatograph m...
example 1
[0352] Synthesis of compound (S1-11)
[0353] Compound (S1-11) is in formula (1-4-3), R 1 for C 4 h 9 , L 1 is hydrogen, L 2 , L 4 and L 5 Both are fluorine, X 1 for-CF 3 compound of. (same as compound (1-4-3-a))
[0354]
[0355] The synthesis process is shown in the figure below.
[0356]
[0357] where r.t. is room temperature.
[0358] Synthesis of compound (S1-2)
[0359] Under a nitrogen atmosphere, prepare a Grignard reagent from 11.3 g of dry magnesium and 75.0 g of 1-bromo-3-chloro-5-fluorobenzene (S1-1) using 220 ml of tetrahydrofuran (hereinafter referred to as THF), and cool it to -70°C. 200 ml of THF solution of 52.0 g of trimethyl borate was dripped there, and after stirring at this temperature for 3 hours, it heated to room temperature over 1 hour, and stirred for 12 hours. 2N-hydrochloric acid was added dropwise to the reaction solution and stirred for 1 hour, the product was extracted with ethyl acetate, was...
example 2
[0383] Synthesis of compound (S2-1)
[0384] Compound (S2-1) is in formula (1-4-3), R 1 for C 5 h 11 , L 1 is hydrogen, L 2 , L 4 and L 5 Both are fluorine, X 1 for-CF 3 compound of.
[0385]
[0386] Synthesis of compound (S2-1)
[0387] The synthesis of (S2-1) was carried out according to the synthesis method of (S1-11) in Example 1. The phase transition temperature of the obtained compound (S2-1) is shown below.
[0388] Phase transition temperature (°C): K91.4 (N34.4)I.
[0389] 1 The chemical shift δ (ppm) of the H-NMR analysis is shown below, and the obtained compound was identified as (S2-1). In addition, the determination solvent is CDCl 3 . Chemical shift δ(ppm): 7.53(m, 1H), 7.37~7.33(m, 2H), 7.12~7.07(m, 3H), 7.04~7.01(m, 3H), 2.66(t, 2H), 1.69~ 1.63(m, 2H), 1.41~1.31(m, 4H), 0.92(t, 3H).
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