LIQUID CRYSTAL COMPOSITION AND ELEMENT

Abstract

A liquid crystal composition contains at least one compound selected from compounds represented by Formula (1), at least one compound selected from compounds represented by Formula (2), and at least one compound selected from compounds represented by Formula (3).

##STR00001##

For example, R.sup.1, R.sup.2, and R.sup.3 are C1-12 alkyl, L.sup.11, L.sup.14, L.sup.15, L.sup.22, L.sup.23, L.sup.32, L.sup.33, Y.sup.11, Y.sup.21, Y.sup.31, and Y.sup.32 are hydrogen, L.sup.12 is fluorine, and L.sup.13, L.sup.21, and L.sup.31 are methyl.

Claims

1. A liquid crystal composition, comprising at least one compound selected from compounds represented by Formula (1), at least one compound selected from compounds represented by Formula (2), and at least one compound selected from compounds represented by Formula (3), ##STR00051## in Formula (1) to Formula (3), R.sup.1, R.sup.2, and R.sup.3 are hydrogen, a halogen, or C1-12 alkyl in which at least one CH.sub.2 may be substituted with O or S, at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC, and at least one hydrogen in these groups may be substituted with a halogen; L.sup.11, L.sup.12, L.sup.13, L.sup.14, L.sup.15, L.sup.21, L.sup.22, L.sup.23, L.sup.31, L.sup.32, and L.sup.33 are hydrogen, a halogen, C1-3 alkyl, or C3-5 cycloalkyl; and Y.sup.11, Y.sup.21, Y.sup.31, and Y.sup.32 are hydrogen or a halogen.

2. The liquid crystal composition according to claim 1, wherein, in at least one compound selected from the compounds represented by Formula (1), at least two of L.sup.11, L.sup.12, L.sup.13, L.sup.14, L.sup.15, and Y.sup.11 are not hydrogen and at least one is methyl.

3. The liquid crystal composition according to claim 1, comprising, as the compound represented by Formula (1), at least one compound selected from a group of compounds represented by Formula (1-1) to Formula (1-7), ##STR00052## in Formula (1-1) to Formula (1-7), R.sup.1 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; L.sup.14 and L.sup.15 are hydrogen, fluorine, chlorine, methyl, or ethyl; and Y.sup.11 is hydrogen, fluorine, or chlorine.

4. The liquid crystal composition according to claim 1, comprising, as the compound represented by Formula (2), at least one compound selected from a group of compounds represented by Formula (2-1) to Formula (2-9), ##STR00053## in Formula (2-1) to Formula (2-9), R.sup.2 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; in Formula (2-7), L.sup.21 is fluorine, chlorine, methyl, or ethyl; in Formula (2-8), L.sup.22 is fluorine, chlorine, methyl, or ethyl; and in Formula (2-7) and Formula (2-8), L.sup.23 is fluorine, chlorine, methyl, or ethyl.

5. The liquid crystal composition according to claim 1, comprising, as the compound represented by Formula (3), at least one compound selected from a group of compounds represented by Formula (3-1) to Formula (3-9), ##STR00054## in Formula (3-1) to Formula (3-9), R.sup.3 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; Y.sup.31 is hydrogen, fluorine, or chlorine; in Formula (3-7), L.sup.31 is fluorine, chlorine, methyl, or ethyl; in Formula (3-8), L.sup.32 is fluorine, chlorine, methyl, or ethyl; and in Formula (3-7) and Formula (3-8), L.sup.33 is fluorine, chlorine, methyl, or ethyl.

6. The liquid crystal composition according to claim 1, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (1) is in a range from 5 weight % to 20 weight %, a proportion of the compound represented by Formula (2) is in a range from 15 weight % to 65 weight %, and a proportion of the compound represented by Formula (3) is in a range from 5 weight % to 25 weight %.

7. The liquid crystal composition according to claim 1, comprising at least one compound selected from a group of compounds represented by Formula (4), compounds represented by Formula (5), compounds represented by Formula (6), compounds represented by Formula (7), compounds represented by Formula (8), compounds represented by Formula (9), and compounds represented by Formula (10), ##STR00055## in Formula (4) to Formula (10), R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, and R.sup.11 are hydrogen, a halogen, or C1-12 alkyl in which at least one CH.sub.2 may be substituted with O or S, at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC, and at least one hydrogen in these groups may be substituted with a halogen; L.sup.41, L.sup.42, L.sup.43, L.sup.51, L.sup.52, L.sup.53, L.sup.61, L.sup.62, L.sup.63, L.sup.71, L.sup.72, L.sup.73, L.sup.74, L.sup.81, L.sup.82, L.sup.83, L.sup.84, L.sup.91, L.sup.92, L.sup.93, L.sup.94, L.sup.95, L.sup.101, L.sup.102, L.sup.103, L.sup.104, L.sup.105, L.sup.106 and L.sup.107 are hydrogen, a halogen, C1-3 alkyl, or C3-5 cycloalkyl; Y.sup.41, Y.sup.42, Y.sup.43, Y.sup.51, Y.sup.52, Y.sup.53, Y.sup.54, Y.sup.55, Y.sup.56, Y.sup.61, Y.sup.62, Y.sup.71, Y.sup.72, Y.sup.73, Y.sup.74, Y.sup.75, Y.sup.76, Y.sup.81, and Y.sup.91 are hydrogen or a halogen; a ring A and a ring B are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, 2,6,7-trioxabicyclo[2.2.2]octane-1,4-diyl, naphthalene-2,6-diyl, or pyridine-2,5-diyl, and at least one hydrogen on these rings may be substituted with a halogen or C1-3 alkyl; Z.sup.81 and Z.sup.82 are a single bond, CC, or CCCC; and a is 0, 1, or 2, b is 1, 2, or 3, a+b is 3, c and d are 0 or 1, when c is 0, d is 0, e and f are 0 or 1, and g is 0, 1, or 2.

8. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (4), at least one compound selected from a group of compounds represented by Formula (4-1) to Formula (4-10), ##STR00056## ##STR00057## in Formula (4-1) to Formula (4-10), R.sup.4 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; Y.sup.42 is hydrogen, fluorine, or chlorine; and in Formula (4-10), Y.sup.41 is hydrogen, fluorine, or chlorine.

9. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (4) is in a range from 5 weight % to 40 weight %.

10. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (5), at least one compound selected from a group of compounds represented by Formula (5-1) to Formula (5-9), ##STR00058## in Formula (5-1) to Formula (5-9), R.sup.5 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; Y.sup.55 is hydrogen, fluorine, or chlorine; in Formula (5-7), L.sup.51 is fluorine, chlorine, methyl, or ethyl; in Formula (5-8), L.sup.52 is fluorine, chlorine, methyl, or ethyl; and in Formula (5-7) and Formula (5-8), L.sup.53 is fluorine, chlorine, methyl, or ethyl.

11. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (5) is in a range from 5 weight % to 60 weight %.

12. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (6), at least one compound selected from a group of compounds represented by Formula (6-1) to Formula (6-10), ##STR00059## ##STR00060## in Formula (6-1) to Formula (6-10), R.sup.6 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; and Y.sup.61 is hydrogen, fluorine, or chlorine.

13. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (6) is in a range from 5 weight % to 20 weight %.

14. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (7), at least one compound selected from a group of compounds represented by Formula (7-1) to Formula (7-9), ##STR00061## in Formula (7-1) to Formula (7-9), R.sup.7 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; L.sup.73 and L.sup.74 are hydrogen, fluorine, chlorine, methyl, or ethyl; and Y.sup.75 and Y.sup.76 are hydrogen, fluorine, or chlorine.

15. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (7) is in a range from 5 weight % to 20 weight %.

16. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (8), at least one compound selected from a group of compounds represented by Formula (8-1) to Formula (8-8), ##STR00062## in Formula (8-1) to Formula (8-8), R.sup.8 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; L.sup.81, L.sup.82, L.sup.83, and L.sup.84 are hydrogen, fluorine, chlorine, methyl, or ethyl; and Y.sup.81 is hydrogen, fluorine, or chlorine.

17. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (8) is in a range from 5 weight % to 20 weight %.

18. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (9), at least one compound selected from a group of compounds represented by Formula (9-1) to Formula (9-9), ##STR00063## in Formula (9-1) to Formula (9-9), R.sup.9 is C1-12 alkyl in which at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; L.sup.93, L.sup.94, and L.sup.95 are hydrogen, fluorine, chlorine, methyl, or ethyl; and Y.sup.91 is hydrogen, fluorine, or chlorine.

19. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (9) is in a range from 5 weight % to 20 weight %.

20. The liquid crystal composition according to claim 7, comprising, as the compound represented by Formula (10), at least one compound selected from a group of compounds represented by Formula (10-1) to Formula (10-6), ##STR00064## in Formula (10-1) to Formula (10-6), R.sup.10 and R.sup.11 are C1-12 alkyl in which at least one CH.sub.2 may be substituted with O, and at least one (CH.sub.2).sub.2 may be substituted with CHCH or CC; in Formula (10-1) and Formula (10-2), L.sup.105, L.sup.106, and L.sup.107 are hydrogen, fluorine, chlorine, methyl, or ethyl; in Formula (10-3), L.sup.102, L.sup.104, L.sup.105, L.sup.106, and L.sup.107 are hydrogen, fluorine, chlorine, methyl, or ethyl; in Formula (10-4), L.sup.101, L.sup.103, L.sup.105, L.sup.106, and L.sup.107 are hydrogen, fluorine, chlorine, methyl, or ethyl; and in Formula (10-5) and Formula (10-6), L.sup.101, L.sup.102, L.sup.103, L.sup.104, L.sup.105, L.sup.106, and L.sup.107 are hydrogen, fluorine, chlorine, methyl, or ethyl.

21. The liquid crystal composition according to claim 7, wherein, based on a weight of the liquid crystal composition, a proportion of the compound represented by Formula (10) is in a range from 5 weight % to 50 weight %.

22. The liquid crystal composition according to claim 1, wherein a refractive index anisotropy at 25 C. at a wavelength of 589 nm is 0.40 or more.

23. The liquid crystal composition according to claim 1, wherein a dielectric anisotropy at 25 C. in a frequency range of 1 kHz is 10 or more.

24. The liquid crystal composition according to claim 1, wherein a dielectric anisotropy at 25 C. in at least one frequency range from 1 GHz to 10 THz is in a range from 1.0 to 3.0.

25. The liquid crystal composition according to claim 1, comprising an optically active compound.

26. The liquid crystal composition according to claim 1, comprising a polymerizable compound.

27. The liquid crystal composition according to claim 1, comprising at least one of an antioxidant, an ultraviolet absorber, an antistatic agent, and a dichroic dye.

28. An element, comprising the liquid crystal composition according to claim 1, wherein the element is used for switching and is capable of reversibly controlling a dielectric constant by reversibly changing an orientation direction of liquid crystal molecules.

29. An element, comprising the liquid crystal composition according to claim 1, wherein the element is used for controlling electromagnetic waves in a frequency range from 1 GHz to 10 THz.

30. A liquid crystal lens, comprising the liquid crystal composition according to claim 1.

31. A birefringent lens for stereoscopic image display, comprising the liquid crystal composition according to claim 1.

32. Alight modulator, comprising the liquid crystal composition according to claim 1.

Description

EXAMPLES

[0277] The disclosure will be described in more detail with reference to Examples. The disclosure is not limited by these Examples. The disclosure also includes mixtures obtained by mixing at least two compositions of Examples. The synthesized compounds were identified by NMR analysis. The characteristics of the compositions were measured according to methods described below.

[0278] NMR analysis: The measurement instrument used was DRX-500 (manufactured by Bruker BioSpin Corporation). For .sup.1H-NMR measurements, the sample was dissolved in a deuterated solvent such as CDCl.sub.3, and the measurement was performed at room temperature, at 500 MHz, with a cumulative count of 16 scans. Tetramethylsilane was used as an internal standard. For .sup.19F-NMR measurements, CFCl.sub.3 was used as an internal standard, and the measurement was performed with a cumulative count of 24 scans. In the description of nuclear magnetic resonance spectra, s means singlet, d means doublet, t means triplet, q means quartet, quin means quintet, sex means sextet, m means multiplet, and br means broad.

[0279] Measurement samples: When measuring phase structure and a transition temperature, the liquid crystalline compound itself was used as the sample. When measuring physical properties such as an upper limit temperature of a nematic phase, a viscosity, an optical anisotropy, a dielectric anisotropy, a composition prepared by mixing the compound with a base liquid crystal was used as the sample.

[0280] In the case of using a sample prepared by mixing the compound with abase liquid crystal, the measurement was performed according to the following method. A sample was prepared by mixing 20 weight % of the compound and 80 weight % of the base liquid crystal. Based on the measured value of this sample, an extrapolated value was calculated according to the extrapolation method expressed by the following equation, and the extrapolated value was recorded.

[00001]$<\mathrm{Extrapolated}\mathrm{value}>=(100<\mathrm{Measured}\mathrm{value}\mathrm{of}\mathrm{sample}>-<\mathrm{Weight}\%\mathrm{of}\mathrm{base}\mathrm{liquid}\mathrm{crystal}><\mathrm{Measured}\mathrm{value}\mathrm{of}\mathrm{base}\mathrm{liquid}\mathrm{crystal}>/<\mathrm{Weight}\%\mathrm{of}\mathrm{compound}>$

[0281] Even with this proportion of the compound to the base liquid crystal, in the case where crystals (or smectic phase) precipitated at 25 C., the proportion of the compound to the base liquid crystal was changed in the order of 10 weight %:90 weight %, 5 weight %:95 weight %, and 1 weight %:99 weight %, and the physical properties of the sample were measured at the proportion at which crystals (or smectic phase) no longer precipitated at 25 C. Unless otherwise specified, the proportion of the compound to the base liquid crystal is 20 weight %:80 weight %.

[0282] A base liquid crystal (i) below was used as the base liquid crystal. Proportions of components of the base liquid crystal (i) are shown in weight %.

##STR00035##

[0283] Measurement methods: The characteristics were measured according to the following methods. Most of these were methods described in Japan Electronics and Information Technology Industries Association (hereinafter referred to as JEITA) standards (JEITAED-2521B) deliberated and established by the JEITA, or modified methods thereof. A thin film transistor (TFT) was not attached to a TN element used for the measurement.

Upper limit temperature (NI; C.) of nematic phase:

[0284] A sample was placed on a hot plate of a melting-point measurement apparatus including a polarizing microscope, and heated at a rate of 1 C./min. The temperature was measured when a part of the sample changed from the nematic phase to an isotropic liquid.

Lower limit temperature (Tc; C.) of nematic phase:

[0285] Samples having a nematic phase were placed in glass bottles and stored in freezers at 0 C., 10 C., 20 C., 30 C. and 40 C. for 10 days, and then the liquid crystal phases were observed. For example, when the sample remained in the nematic phase at 20 C. and changed to a crystalline or a smectic phase at 30 C., Tc was recorded as <20 C.

Viscosity (bulk viscosity; f; measured at 20 C.; mPa.Math.s):

[0286] An E-type rotational viscometer manufactured by Tokyo Keiki Inc. was used for measurement.

Viscosity (rotational viscosity; 1; measured at 25 C.; mPa.Math.s):

[0287] The measurement was performed according to the method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, 37 (1995). The sample was placed in a TN cell with a twist angle of 0 and a gap (cell gap) of 5 m between two glass substrates. Voltage was applied to this element in steps of 0.5 V in a range from 16 V to 19.5 V. After 0.2 seconds of non-application, an application was repeated under conditions of a single rectangular wave (rectangular pulse; 0.2 seconds) and non-application (2 seconds). A peak current and a peak time of a transient current generated by this application were measured. A value of a rotational viscosity was obtained based on these measured values and Calculation Formula (8) described on page 40 of the paper of M. Imai et al. A value of a dielectric anisotropy required for this calculation was obtained according to a method described below using the cell used for measuring this rotational viscosity.

Refractive index anisotropy (in the case of n<0.30; measured at 25 C.):

[0288] The measurement was performed with an Abbe refractometer having a polarizing plate attached to an eyepiece, using light at a wavelength of 589 nm. After rubbing the surface of a main prism in one direction, a sample was added dropwise onto the main prism. A refractive index n.sup.// was measured when the direction of polarization was parallel to the rubbing direction. A refractive index n.sub. was measured when the direction of polarization was perpendicular to the rubbing direction. A value of a refractive index anisotropy was calculated according to an equation: n=n.sub.//n.sub..

Refractive index anisotropy (in the case of n0.30; measured at 25 C.):

[0289] A sample was placed in an element composed of two glass substrates and oriented antiparallel. A thickness direction retardation (Rth) of this element was measured using a phase difference film/optical material inspection device (manufactured by Otsuka Electronics Co., Ltd., product name: RETS-100), and a refractive index anisotropy (n) was calculated based on the retardation value (Rth) and a gap (d: cell gap) between the glass substrates according to the following equation. The wavelength of light used was 589 nm.

[00002]$\mathrm{Rth}=n.Math.d$

Dielectric anisotropy (; measured at 25 C.):

[0290] A sample was placed in a TN element in which the gap (cell gap) between two glass substrates was 9 m and the twist angle was 80 degrees. A sine wave (10 V, 1 kHz) was applied to this element, and after 2 seconds, a dielectric constant (.sub.//) in a major axis direction of liquid crystal molecules was measured. A sine wave (0.5 V, 1 kHz) was applied to this element, and after 2 seconds, a dielectric constant (.sub.) in a minor axis direction of liquid crystal molecules was measured. The value of the dielectric anisotropy was calculated according to an equation: =.sub.//.

Dielectric anisotropy at 28 GHz (measured at 25 C.):

[0291] For a dielectric anisotropy at 28 GHz (@28 GHz), a variable short-circuit waveguide to which a window material was attached was filled with liquid crystals according to a method disclosed in Applied Optics, Vol. 44, No. 7, p. 1150 (2005) and held in a static magnetic field of 0.3 T for 3 minutes. A microwave of 28 GHz was inputted to the waveguide, and an amplitude ratio of a reflected wave to an incident wave was measured. The measurement was performed by changing an orientation of the static magnetic field and a tube length of the short-circuit unit to determine refractive indices (n: ne, no) and loss parameters (: e, o).

[0292] For calculation of a complex dielectric constant (, ), the calculated refractive indices, the loss parameters, and the following relational expressions were used.

[00003]${}^{}=n^2-{}^2{}^{}=2n=2/c$

[0293] Herein, c is a light velocity in vacuum, is an angular velocity, and is an extinction coefficient. .sub.// was calculated based on ne, .sub. was calculated based on no, and the dielectric anisotropy (@28 GHz) was calculated according to: .sub.//.sub..

Dielectric loss tangent at 28 GHz (tan ; measured at room temperature):

[0294] A dielectric loss tangent at 28 GHz (tan @28 GHz) was calculated based on / using the complex dielectric constant (, ). Since anisotropy also appeared in tan , a larger value was recorded.

[0295] Compounds in Examples are represented by symbols based on the definitions in Table 2. Numbers in parentheses after the symbols correspond to numbers of the compounds. The symbol () means other liquid crystalline compounds. The proportion (percentage) of the liquid crystalline compounds is weight percentage (weight %) based on the weight of the liquid crystal composition. Finally, characteristic values of the composition are summarized.

TABLE-US-00002 TABLE 2 Notation of compounds using symbols R-(A.sub.1)-Z.sub.1- . . . -Z.sub.n-(A.sub.n)-R 1) Left terminal group R- Symbol C.sub.nH.sub.2n+1 n- C.sub.nH.sub.2n+1O nO CH.sub.2CH V C.sub.nH.sub.2n+1CC nT- 2) Right terminal group -R Symbol C.sub.nH.sub.2n+1 -n OC.sub.nH.sub.2n+1 On CHCH.sub.2 V CCC.sub.nH.sub.2n1 -Tn CN C CCCN -TC NCS NCS CCCF.sub.3 -TCF.sub.3 3) Bonding group -Z.sub.n- Symbol C.sub.2H.sub.4 2 COO E CHCH V CC T CCCC TT 4) Ring structure -A.sub.n- Symbol [00036] B [00037] B(2F) [00038] B(F) [00039] B(F, F) [00040] B(2Me) [00041] B(Me) [00042] B(2Me, 5Me) [00043] B(2Me, 5F) [00044] B(2F, 5Me) 5) Notation example Example No. 1 3-BTB(2Me,5F)TBNCS [00045] Example No. 2 3-BTB(2Me)-NCS [00046] Example No. 3 3-BB(F)B(F,F)NCS [00047] Example No. 4 3-HBTB(2Me)-NCS [00048] Example No. 5 3-BB(F)TB(Me)-NCS [00049] Example No. 6 3-BB(F)TB-TC [00050]

[Comparative Example 1] Liquid Crystal Composition C1

TABLE-US-00003 3-BTB(2Me, 5F)TB-NCS (1-2) 12% 5-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F, F)-NCS (4-2) 10% 4-BB(F)B(F, F)-NCS (4-2) 20% 3-BB(F)TB(Me)-NCS (5-6) 13% 5-BB(F)TB(Me)-NCS (5-6) 7% 3-BB(F)TB(2Me, 5F)-NCS (5-8) 13% 5-BB(F)TB(2Me, 5Me)-NCS (5-8) 10% NI = 193.3 C.; Tc < 30 C.; n = 0.485; = 15.4; 1 = 1037 mPa .Math. s.

[0296] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition C1 at 28 GHz were as follows. [0297] @28 GHz=1.25 [0298] tan @28 GHz=0.006

[Comparative Example 2] Liquid Crystal Composition C2

TABLE-US-00004 3-BTB(2Me, 5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 17% 4-BTB(2Me)-NCS (2-5) 8% 5-BTB(2Me)-NCS (2-5) 15% 3-BB(F)B(F, F)-NCS (4-2) 15% 3-BB(F)TB(Me)-NCS (5-6) 5% 5-BB(F)TB(Me)-NCS (5-6) 15% 3-BB(F)TB(2Me, 5F)-NCS (5-8) 10% 5-BB(F)TB(2Me, 5Me)-NCS (5-8) 5% NI = 106.6 C.; Tc < 40 C.; n = 0.460; = 15.5; 1 = 478 mPa .Math. s.

[0299] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition C2 at 28 GHz were as follows. [0300] @28 GHz=1.25 [0301] tan @28 GHz=0.006

[Comparative Example 3] Liquid Crystal Composition C3

TABLE-US-00005 3-BTB(2Me)-NCS (2-5) 17% 4-BTB(2Me)-NCS (2-5) 8% 5-BTB(2Me)-NCS (2-5) 15% 4-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F, F)-NCS (4-2) 15% 3-BB(F)TB(Me)-NCS (5-6) 10% 5-BB(F)TB(Me)-NCS (5-6) 15% 5-BB(F)TB(2Me, 5Me)-NCS (5-8) 10% NI = 104.6 C.; Tc < 30 C.; n = 0.434; = 14.1; 1 = 410 mPa .Math. s.

[0302] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition C3 at 28 GHz were as follows. [0303] @28 GHz=1.18 [0304] tan @28 GHz=0.007

[Example 1] Liquid Crystal Composition M1

TABLE-US-00006 3-BTB(2Me, 5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 17% 4-BTB(2Me)-NCS (2-5) 8% 5-BTB(2Me)-NCS (2-5) 15% 4-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F, F)-NCS (4-2) 15% 3-BB(F)TB(Me)-NCS (5-6) 5% 5-BB(F)TB(Me)-NCS (5-6) 15% 5-BB(F)TB(2Me, 5Me)-NCS (5-8) 5% NI = 109.2 C.; Tc < 40 C.; n = 0.445; = 14.5; 1 = 421 mPa .Math. s.

[0305] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M1 at 28 GHz were as follows. [0306] @28 GHz=1.22 [0307] tan @28 GHz=0.006

[0308] Comparative Example 1 is an example in which, among the compound (1) to the compound (3), the compound (2) was not used. Here, the @28 GHz of the composition of Comparative Example 1 was 1.25, and the @28 GHz of the composition of Example 1 was 1.22, both of which can be said to be large. On the other hand, 1 was 1037 mPa.Math.s and 421 mPa.Math.s, respectively, and the composition of Example 1 was significantly small. Further, the NI of Comparative Example 1 was very high, which contributed to increasing n, but was too high considering the heating temperature during the production of the liquid crystal composition and the annealing temperature during the production of the element. Furthermore, with regard to Tc, Comparative Example 1 did not maintain a nematic phase at 40 C., whereas Example 1 was able to maintain a nematic phase down to 40 C. or lower. From this, it was confirmed that the compound (2) had the effects of significantly reducing 1 and providing an appropriate liquid crystal temperature range.

[0309] Comparative Example 2 is an example in which, among the compound (1) to the compound (3), the compound (3) was not used. Here, the @28 GHz of the composition of Comparative Example 2 was 1.25, and the @28 GHz of the composition of Example 1 was 1.22, both of which can be said to be large. On the other hand, 1 was 478 mPa.Math.s and 421 mPa.Math.s, respectively, and the composition of Example 1 was significantly small. From this, it was confirmed that the compound (3) had the effects of reducing 1 without deteriorating the high frequency characteristics.

[0310] Comparative Example 3 is an example in which, among the compound (1) to the compound (3), the compound (1) was not used. Here, the @28 GHz of the composition of Comparative Example 3 was 1.18 and the @28 GHz of the composition of Example 1 was 1.22, and the composition of Example 1 can be said to be significantly large. Further, in comparison with Example 1, Comparative Example 3 had a lower NI, did not maintain a nematic phase at 40 C., and had a narrow temperature range for the nematic phase. From this, it was confirmed that the compound (1) had the effects of improving high frequency characteristics while widening the temperature range of the nematic phase.

[Example 2] Liquid Crystal Composition M2

TABLE-US-00007 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 13% 5-BTB(2Me)-NCS (2-5) 15% 4-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F,F)-NCS (4-2) 7% 3-BB(F)TB(Me)-NCS (5-6) 13% 5-BB(F)TB(Me)-NCS (5-6) 7% NI = 99.9 C.; Tc < 30 C.; n = 0.443; = 12.9; 1 = 407 mPa .Math. s.

[0311] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M2 at 28 GHz were as follows. [0312] @28 GHz=1.23 [0313] tan @28 GHz=0.005

[Example 3] Liquid Crystal Composition M3

TABLE-US-00008 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 19% 5-BTB(2Me)-NCS (2-5) 18% 3-BTB(Me)-NCS (2-6) 10% 4-HBTB(2Me)-NCS (3-5) 15% 3-BBB(2Me)-NCS (4-5) 15% 3-BB(F)TB(Me)-NCS (5-6) 3% 3-BB(F)TB(2Me,5F)-NCS (5-8) 10% NI = 101.3 C.; Tc < 40 C.; n = 0.436; = 14.0; 1 = 401 mPa .Math. s.

[0314] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M3 at 28 GHz were as follows. [0315] @28 GHz=1.22 [0316] tan @28 GHz=0.007

[Example 4] Liquid Crystal Composition M4

TABLE-US-00009 5-BTB(F)TB(2Me,5F)-NCS (1-1) 10% 3-BTB(F,F)-NCS (2-2) 10% 3-BTB(2Me)-NCS (2-5) 18% 5-BTB(2Me)-NCS (2-5) 18% 4-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(Me)-NCS (4-6) 20% 5-BB(F)TB(F)-NCS (5-1) 7% 5-BB(F)TB(F,F)-NCS (5-2) 7% NI = 99.1 C.; Tc < 40 C.; n = 0.436; = 14.5; 1 = 401 mPa .Math. s.

[0317] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M4 at 28 GHz were as follows. [0318] @28 GHz=1.22 [0319] tan @28 GHz=0.006

[Example 5] Liquid Crystal Composition M5

TABLE-US-00010 5-BTB(2Me,5Me)TB-NCS (1-4) 10% 3-BTB(2Me)-NCS (2-5) 20% 5-BTB(2Me)-NCS (2-5) 16% 3-BTB(2Me,5F)-NCS (2-8) 10% 3-HBTB(F,F)-NCS (3-2) 13% 3-BB(F)B(F,F)-NCS (4-2) 16% 3-BB(F)TB(2Me,5F)-NCS (5-8) 15% NI = 103.5 C.; Tc < 40 C.; n = 0.438; = 14.3; 1 = 417 mPa .Math. s.

[0320] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M5 at 28 GHz were as follows. [0321] @28 GHz=1.22 [0322] tan @28 GHz=0.006

[Example 6] Liquid Crystal Composition M6

TABLE-US-00011 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 17% 4-BTB(2Me)-NCS (2-5) 11% 5-BTB(2Me)-NCS (2-5) 17% 3-HBTB(Me)-NCS (3-6) 10% 3-BB(F)B(F,F)-NCS (4-2) 7% 3-BB(F)TB(2Me)-NCS (5-5) 5% 3-BB(F)TB(2Me,5F)-NCS (5-8) 13% 3-HBB(F,F)-NCS (6-2) 10% NI = 107.1 C.; Tc < 40 C.; n = 0.436; = 14.4; 1 = 415 mPa .Math. s.

[0323] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M6 at 28 GHz were as follows. [0324] @28 GHz=1.22 [0325] tan @28 GHz=0.006

[Example 7] Liquid Crystal Composition M7

TABLE-US-00012 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 18% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 17% 5-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F,F)-NCS (4-2) 15% 3-BB(F)TB(Me)-NCS (5-6) 8% 3-HBB(2Me)-NCS (6-6) 12% NI = 103.8 C.; Tc < 30 C.; n = 0.423; = 14.5; 1 = 379 mPa .Math. s.

[0326] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M7 at 28 GHz were as follows. [0327] @28 GHz=1.19 [0328] tan @28 GHz=0.006

[Example 8] Liquid Crystal Composition M8

TABLE-US-00013 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 18% 4-BTB(2Me)-NCS (2-5) 8% 5-BTB(2Me)-NCS (2-5) 17% 5-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F,F)-NCS (4-2) 15% 3-BB(F)TB(Me)-NCS (5-6) 12% 3-BTB(2Me,5F)B(F)-NCS (7-6) 10% NI = 104.5 C.; Tc < 30 C.; n = 0.441; = 14.6; 1 = 470 mPa .Math. s.

[0329] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M8 at 28 GHz were as follows. [0330] @28 GHz=1.23 [0331] tan @28 GHz=0.006

[Example 9] Liquid Crystal Composition M9

TABLE-US-00014 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 14% 5-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F,F)-NCS (4-2) 16% 3-BB(F)TB(Me)-NCS (5-6) 13% 5-BB(F)TB(Me)-NCS (5-6) 2% 5-BB(F)TB(2Me)B(F,F)-NCS (8-6) 5% NI = 110.6 C.; Tc < 10 C.; n = 0.449; = 14.5; 1 = 473 mPa .Math. s.

[0332] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M9 at 28 GHz were as follows. [0333] @28 GHz=1.24 [0334] tan @28 GHz=0.006

[Example 10] Liquid Crystal Composition M10

TABLE-US-00015 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 14% 5-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F,F)-NCS (4-2) 16% 3-BB(F)TB(Me)-NCS (5-6) 13% 5-BB(F)TB(Me)-NCS (5-6) 2% 5-BB(F)TB(2F,5Me)TB-NCS (8-8) 5% NI = 113.3 C.; Tc < 20 C.; n = 0.459; = 14.0; 1 = 485 mPa .Math. s.

[0335] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M10 at 28 GHz were as follows. [0336] @28 GHz=1.27 [0337] tan @28 GHz=0.006

[Example 11] Liquid Crystal Composition M11

TABLE-US-00016 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 20% 5-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F,F)-NCS (4-2) 5% 3-BB(F)TB(2Me,5F)-NCS (5-8) 10% 3-BB(F)TB-TC (9-5) 10% NI = 115.9 C.; Tc < 30 C.; n = 0.460; = 14.2; 1 = 447 mPa .Math. s.

[0338] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M11 at 28 GHz were as follows. [0339] @28 GHz=1.25 [0340] tan @28 GHz=0.007

[Example 12] Liquid Crystal Composition M12

TABLE-US-00017 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 5% 5-BTB(2Me)-NCS (2-5) 15% 5-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F,F)-NCS (4-2) 5% 3-BB(F)TB(2Me,5F)-NCS (5-8) 10% 5-BTB(F)-TC (9-1) 10% 3-BB(F)TB-TC (9-5) 10% NI = 130.0 C.; Tc < 30 C.; n = 0.481; = 16.2; 1 = 496 mPa .Math. s.

[0341] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M12 at 28 GHz were as follows. [0342] @28 GHz=1.25 [0343] tan @28 GHz=0.007

[Example 13] Liquid Crystal Composition M13

TABLE-US-00018 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 20% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 20% 5-HBTB(2Me)-NCS (3-5) 10% 3-BB(F)B(F,F)-NCS (4-2) 10% 3-BB(F)TB(Me)-NCS (5-6) 10% 3-BTTB-O1 (10-2) 10% NI = 92.0 C.; Tc < 30 C.; n = 0.429; = 11.9; 1 = 349 mPa .Math. s.

[0344] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M13 at 28 GHz were as follows. [0345] @28 GHz=1.18 [0346] tan @28 GHz=0.007

[Example 14] Liquid Crystal Composition M14

TABLE-US-00019 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 17% 4-BTB(2Me)-NCS (2-5) 5% 5-BTB(2Me)-NCS (2-5) 15% 5-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F,F)-NCS (4-2) 5% 3-BB(F)TB(Me)-NCS (5-6) 3% 3-BB(F)TB(2Me,5F)-NCS (5-8) 10% 3-BTTB-O1 (10-2) 10% 5-BTTB-O1 (10-2) 10% NI = 112.9 C.; Tc < 20 C.; n = 0.450; = 10.7; 1 = 423 mPa .Math. s.

[0347] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M14 at 28 GHz were as follows. [0348] @28 GHz=1.18 [0349] tan @28 GHz=0.007

[Example 15] Liquid Crystal Composition M15

TABLE-US-00020 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 10% 5-HBTB(2Me)-NCS (3-5) 15% 3-BB(F)B(F,F)-NCS (4-2) 5% 3-BB(F)TB(Me)-NCS (5-6) 10% 3-BB(F)TB(2Me,5F)-NCS (5-8) 10% 3-BTTB-O1 (10-2) 10% 5-BTTB-O1 (10-2) 10% 5-BTB(F)TB-2 (10-6) 10% NI = 144.8 C.; Tc < 30 C.; n = 0.474; = 10.0; 1 = 572 mPa .Math. s.

[0350] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M15 at 28 GHz were as follows. [0351] @28 GHz=1.24 [0352] tan @28 GHz=0.007

[Example 16] Liquid Crystal Composition M16

TABLE-US-00021 3-BTB(2Me,5F)TB-NCS (1-2) 10% 3-BTB(2Me)-NCS (2-5) 18% 4-BTB(2Me)-NCS (2-5) 10% 5-BTB(2Me)-NCS (2-5) 18% 5-HBTB(F,F)-NCS (3-2) 15% 3-BB(F)B(F,F)-NCS (4-2) 20% 3-BB(F)TB(Me)-NCS (5-6) 9% NI = 100.6 C.; Tc < 40 C.; n = 0.427; = 14.9; 1 = 367 mPa .Math. s.

[0353] The dielectric anisotropy (@28 GHz) and the dielectric loss tangent (tan @28 GHz) of the liquid crystal composition M16 at 28 GHz were as follows. [0354] @28 GHz=1.20 [0355] tan @28 GHz=0.007

[0356] The compositions of Example 1 to Example 16 each include the compound (1) to the compound (3). As the constituent components of the composition, those including more of such compounds exhibit a larger dielectric anisotropy at high frequencies. In particular, the value of tan @28 GHz becomes smaller.

[0357] The liquid crystal compositions using the compound (1) to the compound (3) can keep @28 GHz large and reduce the value of tan @28 GHz while maintaining the basic performance as liquid crystal compositions.

[0358] The characteristics required for a liquid crystal composition include: a large dielectric anisotropy () that enables large phase control in a frequency domain used for phase control; and a small dielectric loss tangent (tan ) proportional to absorption energy of electromagnetic wave signals of the liquid crystal composition. The results of Examples and Comparative Examples have illustrated that the composition of the disclosure has a large dielectric anisotropy (@28 GHz) and a small dielectric loss tangent (tan @28 GHz). In general, the smaller the tan , the lower the absorption energy of electromagnetic waves. Accordingly, the liquid crystal composition using the compounds represented by Formula (1) is capable of reducing the absorption energy of electromagnetic wave signals and can set the loss of electromagnetic wave signals to be smaller. Based on the above, it can be concluded that the liquid crystal composition of the disclosure can perform transmission of electromagnetic wave signals more efficiently.

Industrial Applicability

[0359] The liquid crystal composition of the disclosure can satisfy the high-frequency characteristics of the composition, such as a large refractive index anisotropy in the frequency domain for performing control on electromagnetic wave signals and a small dielectric loss tangent (tan ), while having a high upper limit temperature of the nematic phase and a low lower limit temperature of the nematic phase. Furthermore, it becomes possible to provide more preferable liquid crystal compositions by further satisfying at least one of characteristics of the composition, such as a large dielectric anisotropy at low frequencies for reducing a driving voltage, a small viscosity, a large specific resistance in the driving frequency domain, and stability against heat. Elements containing this composition may be used for control on electromagnetic wave signals in the frequency range from 1 GHz to 10 THz.