Liquid crystal media and electronic components

Abstract

We provide liquid crystal media and electronic components. [Solution] The present invention relates to a) a liquid crystal medium and liquid crystal material comprising one or more compounds of formula I and one or more compounds of formula T, and an electronic component comprising the LC medium and capable of operating in the visible (VIS), infrared (IR), or microwave region of the electromagnetic spectrum. The present invention further relates to the use of the LC medium in the IR, VIS, or microwave region, and a device comprising the electronic component. TIFF2026097742000181.tif67166

Description

[Technical Field]

[0001] The present invention relates to liquid crystal (LC) media and electronic components including the LC media that are operable in the visible (VIS), infrared (IR), or microwave regions of the electromagnetic spectrum. The present invention further relates to the use of the LC media in the IR, VIS, or microwave regions and to devices including the electronic components. [Background technology]

[0002] Liquid crystal media have been used for many years in electro-optical displays (liquid crystal displays: LCDs) to display information by amplitude modulation of polarization in the visible region, and are widely used in televisions, monitors, and displays for portable devices such as tablet PCs and mobile phones.

[0003] Nematic liquid crystals have also been proposed for the phase modulation of light. The paper, *Optical phased array technology*, Proc IEEE, 1996; Vol. 84: pp. 268-298; doi: 10.1109 / 5.482231 (Non-patent Literature 1) by McManamon PF, Dorschner TA, Corkum DL, Friedman LJ, Hobbs DS, Holz M, Liberman S, Nguyen HQ, Resler DP, Sharp RC, and Watson EA, describes liquid crystal optical phased arrays for various types of sensor applications. The paper, "Liquid crystal waveguides: new devices enabled by >1000 waves of optical phase control," by Scott R. Davis, George Farca, Scott D. Rommel, Seth Johnson, and Michael H. Anderson, Proc. SPIE7618, Emerging Liquid Crystal Technologies V, No. 76180E (February 12, 2010); doi:10.1117 / 12.851788 (Non-patent document 2), describes refractive beam manipulation using waveguide structures.

[0004] Liquid crystal on silicon (LCoS) is a small, reflective, active-matrix liquid crystal display or "microdisplay" that uses a top layer of liquid crystal on a silicon backing plate. It is also known as a spatial light modulator (SLM).

[0005] The silicon backplate is an array of pixels, each having a mirror surface and simultaneously functioning as a conductor. Each pixel contains a stationary mirror covered with an active liquid crystal layer having a twisted nematic orientation that can be switched to a homeotropic orientation by the application of voltage. LCoS microdisplays are typically small, with a diagonal of less than 1.0 inch, but can achieve high resolutions from 1 / 4 VGA (78,000 pixels) to UXGA+ (over 2 million pixels).

[0006] Due to the small pixel size, LCoS displays also have very small cell thicknesses, typically around 1 micron. When the device operates in reflective mode, light passes through the LC layer twice, which may also require a low cell thickness. Therefore, the liquid crystal phase used in these displays must have a particularly high optical anisotropy Δn, in contrast to conventional reflective LC displays, which typically require a low Δn LC phase. Since response time decreases quadratically with cell thickness, small cell thicknesses are preferred, especially in applications requiring very short response times.

[0007] Liquid crystal compounds with high birefringence often possess an intrinsic smectic phase, or when mixed with other liquid crystal compounds, they induce the formation of a smectic phase, which adversely affects the low-temperature stability of displays.

[0008] Initially developed for projection televisions, LCoS is now also used in wavelength-selective switches, structural illumination, near-eye displays, and optical pulse shaping. Computer-generated holograms may be encoded on a spatial light modulator positioned to modulate the amplitude and / or phase of incident light that forms part of a hologram projector, as described in International Publication No. 2020 / 015933 (Patent Document 1). Such projectors have found applications in head-up displays (HUDs) and head-mounted displays (HMDs), including near-eye devices.

[0009] Another application of liquid crystal devices is LiDAR (light detection and ranging), a method of measuring distance by shining laser light onto a target and measuring the reflection with a sensor. Therefore, differences in laser reflection time and wavelength can be used to create a digital three-dimensional representation of the target. International Publication No. 2019 / 24052 (Patent Document 2) proposes, for example, a holographic LiDAR system using LCoS SLM.

[0010] One of the most important features of phase-dedicated LCoS devices is the use of optically nonlinear liquid crystal materials that are sensitive to operating temperature. While conventional LCoS devices primarily rely on light intensity modulation, which is less affected by temperature changes, in phase-dedicated LCoS devices, the optical phase modulation of the incident light is an essential performance parameter and can be easily affected by even slight changes in operating temperature, resulting in significant changes in the output of the corresponding optical diffraction.

[0011] Another significant challenge in the development of next-generation LCoS devices is the creation of high-speed multilevel phase modulation. While nematic LCoS devices offer the advantages of multilevel phase modulation, they are constrained by the slow response speed of nematic LCs. This is especially true for communications applications requiring thicker devices using infrared wavelengths, thus further slowing the response speed. Therefore, the main materials challenge in these applications is finding suitable high-speed LC materials that can achieve the full 2π phase depth required in these applications.

[0012] Therefore, there is a need for liquid crystal optical components, particularly LCOS devices, that have high birefringence and high switching speed, improved overall application-related characteristics, and can operate in the visible or infrared region of the electromagnetic spectrum. [Prior art documents] [Patent Documents]

[0013] [Patent Document 1] International Publication No. 2020 / 015933 [Patent Document 2] International Publication No. 2019 / 24052 [Non-patent literature]

[0014] [Non-Patent Document 1] Mcmanamon PF, Dorschner TA, Corkum DL, Friedman LJ, Hobbs DS, Holz M, Liberman S, Nguyen HQ, Resler DP, Sharp RC, Watson EA, Optical phased array technology.Proc IEEE.1996;84:268-298;doi:10.1109 / 5.482231 [Non-Patent Document 2] Scott R. Davis, George Farca, Scott D. Rommel, Seth Johnson, and Michael H. Anderson, "Liquid crystal waveguides: new devices enabled by >1000 waves of optical phase control," Proc.SPIE7618, Emerging Liquid Crystal Technologies V, No. 76180E (February 12, 2010);doi:10.1117 / 12.851788 [Disclosure of the Invention] [Problems that the invention aims to solve]

[0015] This invention was conceived in light of the problems of the prior art described herein. Therefore, a general object of this invention is to provide novel and useful materials, devices, and techniques that can solve the problems described herein. [Means for solving the problem]

[0016] The object of the present invention is a) one or more compounds of formula I; and b) a liquid crystal medium comprising one or more compounds of formula T.

[0017] [ka]

[0018] During the ceremony, R 11 and R 12 This refers to alkyl or alkoxy groups having the same or different H atoms, 1 to 12 C atoms, or alkenyl, alkenyloxy, or alkoxyalkyl groups having 2 to 12 C atoms (however, one or more CH2 groups are... [ka] This represents a state where (it may be replaced by fluorine, however, one or more H atoms may be replaced by fluorine), L 11 , L 12 , L 13 These represent H, CH3, Cl, or F, whether identical or different. A 11 This represents phenylene-1,4-diyl (where one or two CH groups may be replaced with N, and one or more H atoms may be replaced with halogens, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2, or OCF3), cyclohexane-1,4-diyl, or cyclohexene-1,4-diyl (where one or two non-adjacent CH2 groups in each may be independently replaced with O and / or S, and one or more H atoms may be replaced with F), bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl (where one or more H atoms may be replaced with F), A 12is phenylene-1,4-diyl (where one or two CH groups may be replaced by N, and one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3), or cyclohexane-1,4-diyl or cyclohexene-1,4-diyl (where one or two non-adjacent CH2 groups may each independently be replaced by O and / or S, and one or more H atoms may be replaced by F), preferably phenylene-1,4-diyl (where one or more H atoms may be replaced by halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3) or cyclohexane-1,4-diyl, Z 1 is a single bond, -CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF- or -CH=CHCH2O-, preferably a single bond, n is 0 or 1, preferably 1.

[0019] [Chemical formula]

[0020] In the formula, R T1 and R T2 are the same or different and are H, halogen, -CN, -SCN, linear alkyl or alkoxy having 1 to 15 C atoms, linear alkenyl or alkenyloxy having 2 to 15 C atoms or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 C atoms (in which one or more CH2 groups are replaced so that O atoms are not directly linked to each other, [Chemical formula] -C≡C-, -CF2O-, -OCF2-, -CH=CH-, -O-, -CO-O- or -O-CO- may be replaced, provided that one or more H atoms may be replaced by halogen). R T3 This includes F, -CN, linear alkyl or alkoxy having 1 to 5 carbon atoms, linear alkenyl or alkenyloxy having 2 to 5 carbon atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 5 carbon atoms (in this group, the CH2 group is [ka] This represents a compound (which may be replaced by a halogen, however one or more H atoms may be replaced by halogens), A 0 , A 1 and A 2 Each of these independently represents phenylene-1,4-diyl (where one or two CH groups may be replaced by N, and one or more H atoms may be replaced by halogens, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2, or OCF3), cyclohexane-1,4-diyl (where one or two non-adjacent CH2 groups may be independently replaced by O and / or S, and one or more H atoms may be replaced by F), cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl. Z 1 and Z 2 These each independently represent -CF2O-, -OCF2-, -CH2O-, -OCH2-, -CO-O-, -O-CO-, -C2H4-, -C2F4-, -CF2CH2-, -CH2CF2-, -CFHCFH-, -CFHCH2-, -CH2CFH-, -CF2CFH-, -CFHCF2-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C-, or a single bond. n is 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 0 or 1, and especially preferably 0. m is 0, 1, 2, or 3, preferably 0, 1, or 2, very preferably 1 or 2, and especially 1.

[0021] According to another aspect of the present invention, an electronic component comprising a liquid crystal medium according to the present invention is provided.

[0022] The present invention further relates to a device including the aforementioned electronic component.

[0023] The present invention further relates to the use of media defined above and below for electro-optical purposes for phase modulation of visible or infrared light in the visible or infrared region of the electromagnetic spectrum, preferably in the region of 420 nm to 750 nm or in the A band and / or B band and / or C band. [Brief explanation of the drawing]

[0024] [Figure 1] This figure shows an embodiment of the present invention. [Modes for carrying out the invention]

[0025] The medium according to the present invention is characterized by very high birefringence, and despite the high birefringence, excellent photostability is observed under blue light irradiation. The medium is further distinguished by particularly high dielectric anisotropy and low rotational viscosity. As a result, the threshold voltage, i.e., the minimum voltage at which the device can be switched, is very low. Low operating voltage and low threshold voltage are desirable to enable devices with improved switching characteristics and high energy efficiency. Low rotational viscosity enables rapid switching of components and devices according to the present invention.

[0026] The optical components according to the present invention stand out for their excellent operational stability when exposed to the environment, due to their high transparency temperature, wide nematic phase range, and the excellent low-temperature stability (LTS) of the liquid crystal medium used. As a result, the components and devices containing them can operate even under extreme temperature conditions. Remarkably, the temperature dependence of the birefringence of the liquid crystal medium is very small, i.e., Δn hardly changes with temperature, resulting in highly reliable and easily controllable devices.

[0027] In particular, it is recognized that the medium according to the present invention is characterized by a desirablely high elastic constant.

[0028] The medium according to the present invention is also suitable for use in components and devices for applications in high-frequency technology and the microwave region, particularly in devices for shifting microwave phases, adjustable filters, adjustable metamaterial structures, and electron beam steering antennas (e.g., phased array antennas).

[0029] Accordingly, according to another aspect of the present invention, components and devices containing such components are provided, both of which are capable of operating in the microwave region of the electromagnetic spectrum. Preferred components include phase shifters, varactors, wireless and radio antenna arrays, matching circuits, and adaptive filters.

[0030] Unless otherwise specified, the following definitions apply:

[0031] As used herein, the halogen is F, Cl, Br, or I, preferably F or Cl, and particularly preferably F.

[0032] In this specification, alkyls are linear or branched and have 1 to 15 carbon atoms, preferably linear and having 1, 2, 3, 4, 5, 6 or 7 carbon atoms unless otherwise indicated, and therefore preferably methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or n-heptyl.

[0033] In this specification, branched alkyl is an alkyl having secondary and / or tertiary, preferably secondary, carbon atoms, and is preferably isopropyl, s-butyl, isobutyl, isopentyl, 2-methylhexyl or 2-ethylhexyl, 2-methylpropyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl.

[0034] In this specification, a cyclic alkyl group means an alkyl group in which an alicyclic group or a methylene group is replaced by an alicyclic group (i.e., a cycloalkylalkyl or alkylcycloalkylalkyl), and the group may be saturated or partially unsaturated, preferably representing cyclopropyl, methylcyclopropyl, cyclobutyl, methylcyclobutyl, cyclopentyl, methylcyclopentyl, cyclopenta-1-enyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, or cyclopenta-1-enylmethyl.

[0035] In this specification, the alkoxy group is linear or branched and contains 1 to 15 carbon atoms. It is preferably linear and has 1, 2, 3, 4, 5, 6 or 7 carbon atoms unless otherwise indicated, and is therefore preferably methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy or n-heptoxy.

[0036] In this specification, the alkenyl group is preferably an alkenyl group having 2 to 15 carbon atoms, and the group is linear or branched and contains at least one carbon-C double bond. It is preferably linear and has 2 to 7 carbon atoms. Thus, it is preferably vinyl, propa-1- or -2-enyl, buta-1-, -2- or -3-enyl, penta-1-, -2-, -3- or -4-enyl, hexa-1-, -2-, -3-, -4- or -5-enyl, hepta-1-, -2-, -3-, -4-, -5- or -6-enyl. If two carbon atoms of the carbon-C double bond are substituted, the alkenyl group may be in the form of E and / or Z isomers (trans / cis). Generally, each E isomer is preferred. Among the alkenyl groups, propa-2-enyl, buta-2- and -3-enyl, and penta-3- and -4-enyl are particularly preferred.

[0037] In this specification, alkynyl is understood to mean an alkynyl group having 2 to 15 carbon atoms, the group being linear or branched and containing at least one carbon-carbon triple bond. 1- and 2-propynyl and 1-, 2- and 3-butynyl are preferred.

[0038] As used herein, the infrared region of the electromagnetic spectrum refers to the spectral region of electromagnetic radiation having wavelengths in the range of 0.75 μm to 1000 μm.

[0039] As used herein, visible light means light having wavelengths in the range of 420 nm to 750 nm.

[0040] As used herein, blue light is light having a peak wavelength in the range of 420 nm to 490 nm, preferably 450 nm to 460 nm.

[0041] As used herein, infrared A (IR-A) refers to the spectral region of electromagnetic radiation having wavelengths in the range of 0.75 μm to 1.4 μm.

[0042] As used herein, infrared B (IR-B) refers to the spectral region of electromagnetic radiation having wavelengths in the range of 1.4 μm to 3 μm.

[0043] As used herein, infrared C (IR-C) refers to the spectral region of electromagnetic radiation having wavelengths in the range of 3 μm to 1000 μm.

[0044] Preferably, the optical component according to the present invention operates at wavelengths in the range of 750 nm to 2500 nm, particularly 1530 nm to 1565 nm.

[0045] A very preferred light source for the applications according to the present invention is an IR laser that emits light having a wavelength of 1.55 μm or an IR laser that emits light having a wavelength of 905 nm.

[0046] In this specification, “high-frequency technology” means an application of electromagnetic radiation having a frequency in the range of 1 MHz to 1 THz, preferably 1 GHz to 500 GHz, more preferably 2 GHz to 300 GHz, and particularly preferably 5 GHz to 150 GHz.

[0047] In addition to the compound of formula T, the medium may optionally contain one or more compounds of formula T. * It contains the compound.

[0048] [ka]

[0049] During the ceremony, R T1 , R T2 , A 0 , A 1 , A 2 , Z 1 , Z 2 n and m have the meanings shown for formula T.

[0050] The compound of formula I is preferably present in the medium according to the present invention at a total concentration ranging from 10% to 70%.

[0051] In the medium according to the present invention, formula T and optionally T * The total concentration of one or more compounds represented by is preferably in the range of 1% to 25%.

[0052] The compound of formula I is preferably selected from the group of compounds of formula I-1 to I-3, and particularly preferably from formula I-3.

[0053] [ka]

[0054] In the formula, the appearing groups have the meanings given above in formula I, and preferably in formulas I-1 and I-2. R 11This is an n-alkyl or alkenyl having up to 7 carbon atoms, most preferably an n-alkyl having 1 to 5 carbon atoms. R 12 This is an n-alkoxy or alkenyloxy having 1 to 6 carbon atoms, most preferably an n-alkoxy having 1 to 4 carbon atoms. In I-3, preferably R 11 This is an n-alkyl or alkenyl having up to 7 carbon atoms, most preferably an n-alkyl having 1 to 5 carbon atoms. R 12 This is an n-alkyl or alkenyl having up to 7 carbon atoms, most preferably an n-alkyl having up to 5 carbon atoms.

[0055] The liquid crystal medium according to the present invention preferably comprises one or more compounds of formula I-1 selected from the group of compounds of formula I-1a to I-1d, preferably formula I-1a and / or I-1d, and most preferably formula I-1a.

[0056] [ka]

[0057] In the formula, R 11 and R 12 It has the meaning given above.

[0058] The liquid crystal medium according to the present invention preferably comprises one or more compounds of formula I-2 selected from the group of compounds of formula I-2a to I-2f, preferably formula I-2a and / or I-2d, and most preferably formula I-2a.

[0059] [ka]

[0060] In the formula, R 11 and R 12 It has the meaning given above.

[0061] The liquid crystal medium according to the present invention preferably comprises one or more compounds of formula I-3 selected from the group of compounds of formula I-3a to I-3d, preferably I-3a and / or I-3c and / or I-3d, and most preferably I-3d.

[0062] [ka]

[0063] In the formula, R 11 and R 12 It has the meaning given above.

[0064] A 0 A preferred LC medium contains a compound of formula I where phenylene-1,4-diyl (where one or two CH groups may be replaced with N, and one or more H atoms may be replaced with halogens, CN, CH3, CHF2, CH2F, OCH3, OCHF2, CF3, or OCF3).

[0065] A is particularly preferable. 0 These are the following compounds.

[0066] [ka]

[0067] Very preferably, A 0 teeth,

[0068] [ka]

[0069] A in equation I 1 and A 2is preferably phenylene-1,4-diyl (which may be monosubstituted or polysubstituted with F), more preferably cyclohexane-1,4-diyl, cyclohexenylene-1,4-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl, very preferably phenylene-1,4-diyl (which may be monosubstituted or polysubstituted with F), or cyclohexane-1,4-diyl.

[0070] Z in equation I 1 and Z 2 The bond is preferably -CF2O-, OCF2, or a single bond, and very preferably a single bond.

[0071] A in equation I 1 and A 2 Particularly preferred is, [ka] In the formula, L represents a halogen, CF3, or CN, preferably F.

[0072] Furthermore, in the compound of formula I, R 1 and R 2 Each of these independently represents an alkyl, alkoxy, alkenyl, or alkynyl having H, F, or 1 to 8, preferably 1 to 5, carbon atoms, and each of these may be substituted with a halogen, particularly F.

[0073] R 1 and R 2 Preferably, H represents an alkyl or alkoxy which may be fluorinated having 1 to 7 carbon atoms, an alkenyl or alkynyl which may be fluorinated having 2 to 7 carbon atoms, or an cycloalkyl which may be fluorinated having 3 to 12 carbon atoms.

[0074] Preferably, R 1 and R 2 At least one of them is not H, and is particularly preferably R 1 and R 2 Neither of them is H.1 R is particularly preferably alkyl. 2 More preferably, is H, alkyl, or fluorine. Particularly preferably, R 1 is alkyl, R 2 R is either H or alkyl. 1 , R 2 Each of these independently represents an unbranched alkyl group having 1 to 5 carbon atoms, particularly preferably. 1 and R 2 If R represents a substituted alkyl, alkoxy, alkenyl, or alkynyl, 1 and R 2 The total number of C atoms in the two groups is preferably less than 10.

[0075] A preferred compound of formula T is selected from the following sub-formulas, and more preferably from the compounds of formula T-3.

[0076] [ka]

[0077] In the formula, R T1 , R T2 and R T3 The above has the meaning for equation T, L represents halogen, CN, CH3, CHF2, CH2F, CF3, OCH3, OCHF2 or OCF3, preferably F, and r, s, and t are independently 0, 1, 2, 3, or 4, where r is preferably 1 or 2, very preferably 2, and s and t are independently preferably 0 or 1, very preferably 0.

[0078] R T1 and R T2 In particular, R represents an n-alkyl group having 1 to 7 carbon atoms independently or an alkenyl group having 2 to 7 carbon atoms. T2 is alternatively represented by F, CHF2, CF3, OCHF2, or OCF3, and R T3is more preferably F or an n-alkyl having 1 to 3 C atoms, very preferably F or CH3, and especially CH3.

[0079] In a first very preferred embodiment, the compounds of formula T-1 to T-6 are selected from the compounds of formula T-1a to T-6a, particularly the compound of formula T-3a.

[0080] [ka]

[0081] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0082] In a second, very preferred embodiment, the compounds of formula T-1 to T-6 are selected from the compounds of formula T-1b to T-6b, particularly T-3b.

[0083] [ka]

[0084] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0085] In a third, very preferred embodiment, the compounds of formulas T-1 to T-6 are selected from the compounds of formulas T-1c to T-6c, particularly T-3b.

[0086] [ka]

[0087] In the formula, R T1 , R T2 , R T3L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0088] In a fourth, very preferred embodiment, the compounds of formula T-1 to T-6 are selected from the compounds of formula T-1d to T-6d, particularly T-3d.

[0089] [ka]

[0090] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0091] In a particularly preferred embodiment, the medium according to the present invention comprises one or more compounds selected from the group of formulas T-1a to T-6a and one or more compounds selected from the group of formulas T-1b to T-6b.

[0092] Preferably, the medium comprises one or more compounds selected from the group of compounds of formula T-3a, T-3c, and T-3d.

[0093] [ka]

[0094] In the formula, R T1 , R T2 , R T3 L, r, and s have the meanings defined above for formula T and its sub-formulas.

[0095] Alternatively, an LC medium containing the compound of the following formula T is particularly preferred.

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the formula, n is 1, 2, 3, 4, 5, 6, or 7.

[0100] Alternatively, or in addition, compounds of the following formula T can be used.

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] In another preferred embodiment, the compound of formula T is selected from the following sub-formulas.

[0105] [ka]

[0106] [ka]

[0107] In the formula, R T1 The terms have the meaning defined above for equation T and its sub-equations.

[0108] The medium preferably comprises one or more compounds selected from the group of compounds of formulas S1, S2, and S3. [Chemistry]

[0109] In the formula, R S1 and R S2 are each, in each occurrence, the same or different and are H or a linear alkyl having 1 to 25 carbon atoms or a branched alkyl having 3 to 25 carbon atoms (the group is unsubstituted or monosubstituted with CN or CF3 or at least monosubstituted with a halogen, provided that one or more CH2 groups are each independently such that O and / or S atoms are not directly linked to each other [Chemistry] -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C- may be replaced. ) or a halogen, an aryl, heteroaryl, alkylaryl or arylalkyl having 6, 5, 7 or 7 to 25 carbon atoms respectively (each group is unsubstituted or monosubstituted or polysubstituted with an alkyl having 1 to 6 C atoms or a halogen. ), s is 0, 1 or 2, and t is 0, 1, 2 or 3, G represents a hydrocarbon group which may be linear or branched or cyclic and has 1 to 60 carbon atoms, the group being unsubstituted or monosubstituted with CN or CF3 or at least monosubstituted with a halogen, provided that one or more CH2 groups are each independently such that O or S atoms are not directly linked to each other and -O-, -S-, -NR 0 -,-CO-,-CO-O-,-O-CO-,-O-CO-O-,-CH=CH- or -C≡C- may be replaced, R 0 represents H or an alkyl having 1 to 6 C atoms, R 2 is H, -O ·, -OH, a linear, branched or cyclic alkyl, alkoxy or arylalkoxy having 1 to 12 carbon atoms, preferably H or -O · represents R 21 and R 22 represent linear or branched alkyls having 1 to 12 carbon atoms, which may be the same or different, or R 21 and R 22 together with the carbon atom to which they are attached form a cycloalkyl group having 5 to 12 carbon atoms, R 23 and R 24 represent linear or branched alkyls having 1 to 12 carbon atoms, which may be the same or different, or R 23 and R 24 together with the carbon atom to which they are attached form a cycloalkyl group having 5 to 12 carbon atoms, Z 2 represents, in each occurrence, the same or different -O-, -C(O)O-, -OC(O)- or a single bond, q is 1, 2, 3 or 4, preferably 2, 3 or 4, very preferably 2 or 4, R ST represents H, an alkyl or alkoxy having 1 to 12 carbon atoms or an alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 carbon atoms, provided that one or more CH2 groups may be

Chemical formula

[0110] A very preferred compound of formula S1 is the group R S2 At least one of the groups is a linear or branched alkyl group having 1 to 15 carbon atoms (wherein one or more CH2 groups may be replaced with -COO- or -O-CO-), an aryl or alkylaryl group having 5 to 15 carbon atoms, where X is preferably H or Cl. A particularly preferred group R S2 These are methyl, tert-butyl, 2-butyl, 1,1-dimethylpropyl, 1,1,2,2-tetramethylpropyl, and 1-methyl-1-phenylethyl.

[0111] The compound of formula S1 is preferably selected from the compounds of formula S1-1.

[0112] [ka]

[0113] During the ceremony, R S1 represents H, F, or Cl, preferably H or Cl, and R 21 and R 22 This refers to linear or branched alkyl groups having the same or different H atoms or 1 to 12 carbon atoms (however, one or more CH2 groups are arranged such that the O atoms are not directly bonded to each other independently). [ka] It may be replaced by -O-, -CO-O-, -O-CO-, -CH=CH-, or -C≡C-.) or it represents an aryl or arylalkyl having 6 to 25 carbon atoms.

[0114] Compounds of formula S1-1 selected from the following formulas, or mixtures thereof, are particularly preferred. Compounds of formula S1-1a are particularly preferred.

[0115] [ka]

[0116] [ka]

[0117] Furthermore, the most suitable UV stabilizer is selected from the following formula.

[0118] [ka]

[0119] In formula S2, when q is 2, G may be a divalent linear or branched aliphatic residue (either saturated or unsaturated) having 2 to 20 carbon atoms, a divalent alicyclic residue having 5 to 20 carbon atoms, a divalent aralkyl residue having 8 to 20 carbon atoms, or a divalent aryl residue having 6 to 20 carbon atoms.

[0120] Examples of group G where q is 2 include 1,2-ethylene, 1,2-propylene, 1,4-n-butylene, 1,3-butylene, 1,6-n-hexylene, 1,7-n-heptylene, 1,10-n-decylene, 1,12-n-dodecylene, 2,2-dimethyl-1,3-propylene, 1,2,3-trimethyl-1,4-butylene, 3-thia-1,5-pentylene, 3-oxa-1,5-pentylene, 1,4-buto- These are 2-enylene, 1,4-buto-2-inylene, 2,5-hexa-3-enylene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, hexahydro-p-xylylene, p-xylylene, m-xylylene, 1,2-phenylene, 1,4-phenylene, 2,2'-biphenylene, 4,4'-biphenylene, 2,6-naphthylene, and 2,7-fluoroenylene.

[0121] In formula S2, when q is 3, G may be a trivalent linear or branched aliphatic residue (either saturated or unsaturated) having 3 to 15 carbon atoms, a trivalent alicyclic residue having 5 to 15 carbon atoms, a trivalent aralkyl residue having 9 to 15 carbon atoms, or a trivalent aryl residue having 6 to 16 carbon atoms.

[0122] Examples of group G with q = 3 include 1,2,3-trisubstituted propane, 1,2,4-trisubstituted butane, 2,5-dimethyl-1,2,6-trisubstituted hexane, 1,1,1-trimethylenepropane, 1,2,3-trisubstituted cyclohexane, 1,3,5-trisubstituted cyclohexane, 1,3,5-trimethylenebenzene, and 1,2,7-trisubstituted anthracene.

[0123] In formula S2, when q is 4, G may be a linear or branched tetravalent aliphatic residue (either saturated or unsaturated) having 4 to 60 carbon atoms, or a tetravalent alicyclic residue having 5 to 60 carbon atoms, such as tetramethylenemethane, 1,1,4,4-tetramethylenecyclohexane, arylene-tetraalkylene, or aralkylaryl-tetraalkylene.

[0124] When n is 2, 3, or 4 and G is an aliphatic or alicyclic residue, these residues may be unsubstituted, substituted with a halogen, or interrupted by one or more oxygen atoms, sulfur atoms, or aryl or aralkyl residues. Examples of aryl groups include fused rings such as naphthalene, single bonds, or one, two, or three or more aryl groups linked via alkylene groups.

[0125] base R 21 and R 22 Furthermore, R 23 and R 24 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, n-hexyl, n-dodecyl, or R along with the carbon to which they are bonded. 21 and R 22 Furthermore, R 23 and R 24 teeth [ka] It can form groups such as these.

[0126] Particularly preferred substituent R 21 and R 22 Furthermore, R 23 and R 24 This is a linear or branched alkyl group having 1 to 4 carbon atoms, most preferably methyl.

[0127] A very preferred compound of formula S2 is selected from sub-formulas S2-1 and S2-2.

[0128] [ka]

[0129] In the formula, G represents a divalent aliphatic or alicyclic group having 1 to 20 carbon atoms.

[0130] Examples of group G in formula S2-1 or S2-2 are methylene, ethylene, or polymethylene having up to 20 carbon atoms which may be alkylated; or the alkylene group is interrupted by one or two heteroatoms, such as the divalent group -CH2OCH2-, -CH2CH2OCH2CH2-, -CH2CH2OCH2CH2OCH2CH2-, -CH2C(O)OCH2CH2O(O)CCH2-, -CH2CH2C(O)OCH2CH2O(O)CCH2CH2-, -CH2CH2-C(O)O(CH2)4O(O)C-CH2CH2-, -CH2CH2O(O)C(CH2)4C(O)OCH2CH2- and -CH2CH2O(O)C(CH2)8C(O)OCH2CH2-. G could also be an arylene-bis-alkylene, such as p-xylylene, benzene-1,3-bis(ethylene), biphenyl-4,4'-bis(methylene), or naphthalene-1,4-bis(methylene).

[0131] A more very preferred compound of formula S2 is selected from the compounds of formula S2-3.

[0132] [ka]

[0133] During the ceremony, Sp represents a linear or branched alkylene (wherein one or more CH2 groups may be replaced by oxygen atoms so that the oxygen atoms are not directly linked to each other) or a single bond, each having the same or different carbon atoms in each occurrence.

[0134] Particularly preferably, the medium contains one or more compounds of formula S2-1a or S2-2a, preferably S2-1a.

[0135] [ka]

[0136] During the ceremony, R S3represents H or an alkyl having 1 to 6 C atoms, preferably H or ethyl; t is 0 or 1, and q is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, r is 2, 3, 4, 5, 6, 7 or 8, and s is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0137] Particularly preferred compounds of formula S2 are selected from the compounds of formulae S2-1a-1, S2-1a-2, S2-2a-1 and S2-3a-1. These compounds are characterized by very good solubility in the liquid crystal medium.

[0138]

Chemical formula

[0139] Further preferred examples of the compounds of formula S2 are as follows.

[0140]

Chemical formula

[0141]

Chemical formula

[0142]

Chemical formula

[0146] In the formula, R 2 has the meaning given above and is preferably H or -O · and represents.

[0147] Among the compounds of formula S3, the compounds of formulas S3-1 to S3-4 are particularly preferred.

[0148] [Chemical formula]

[0149] In a preferred embodiment, the medium according to the invention comprises one or more compounds selected from the group consisting of formulas II and III.

[0150] [Chemical formula]

[0151] In the formula, R 2 and R 3 represent an unsubstituted or halogenated linear or branched alkyl or alkoxy group having 1 to 15 C atoms, provided that one or more CH2 groups in these groups are such that O atoms are not directly linked to each other, [Chemical formula] -C≡C-, -CF2O-, -CH=CH-, -O-, -CO-O- or -O-CO- and may each be independently replaced by each other, [Chemical formula] are the same or different [Chemical formula] Preferably [ka] This represents, L 21 , L 22 , L 31 and L 32 These represent H or F, preferably F, and are the same or different. Y 2 and Y 3 These represent H or CH3, whether identical or different. X 2 and X 3 This represents the same or different halogens, alkyl or alkoxy halides having 1 to 3 carbon atoms, or alkenyl or alkenyloxy halides having 2 or 3 carbon atoms, preferably F, Cl, OCF3 or CF3, most preferably F, CF3 or OCF3. Z 3 This represents -CH2CH2-, -CF2CF2-, -COO-, trans--CH=CH-, trans-CF=CF-, -CH2O- or a single bond, preferably -CH2CH2-, -COO-, trans--CH=CH- or a single bond, most preferably -COO-, trans--CH=CH- or a single bond, and l, m, n, and o are each independently 0 or 1, preferably l+m is 2.

[0152] The total concentration of one or more compounds of formula II and / or III in the medium according to the present invention is preferably in the range of 5% to 45%.

[0153] Preferably, the medium contains one or more compounds of formula II, preferably selected from the group of compounds of formula II-1 to II-3, and very preferably selected from the group of compounds of formula II-1 and II-3.

[0154] [ka]

[0155] In the formula, each appearing group has the meaning given in formula II above, and in formula II-1, the group L 23 and L 24 Each represents H or F independently of each other and other parameters, and preferably in formula II-2, [ka] It represents.

[0156] In equations II-1, II-2, and II-3, L 21 and L 22 or L 23 and L 24 Preferably, both represent F.

[0157] In another preferred embodiment of formulas II-1 and II-2, L 21 , L 22 , L 23 and L 24 All of these represent F.

[0158] The compound of formula II-1 is preferably selected from the group of compounds of formula II-1a to II-1h, preferably from II-1a, II-1b, II-1g, and II-1h.

[0159] [ka]

[0160] [ka]

[0161] In the formula, each base that appears has the meaning given above.

[0162] In a preferred embodiment of the present invention, the medium is L 21 and L 22 Furthermore / or L 23 and L 24It contains one or more compounds selected from the group of compounds of formulas II-1a to II-1h, where both of the elements are F.

[0163] In another preferred embodiment, the medium is L 21 , L 22 , L 23 and L 24 This includes compounds selected from the group of compounds represented by formulas II-1a to II-1h, where all of the elements are F.

[0164] This is a particularly preferred compound of formula II-1.

[0165] [ka]

[0166] In the formula, R 2 It has the meaning given above.

[0167] Preferably, the compound of formula II-2 is selected from the group of compounds of formula II-2a to II-2c.

[0168] [ka]

[0169] In the formula, each appearing base has the meaning given above, preferably L 21 and L 22 Both are F.

[0170] Preferably, the compound of formula II-3 is selected from the group of compounds of formula II-3a to II-3e, preferably from II-3d and II-3e.

[0171] [ka]

[0172] In the formula, the bases that appear have the respective meanings given above, preferably L21 and L 22 Both are F, and L 23 and L 24 Both are H, or L 21 , L 22 , L 23 and L 24 All of them are F.

[0173] This is a particularly preferred compound of formula II-3.

[0174] [ka]

[0175] In the formula, R 2 It has the meaning given above.

[0176] Compound II-3d-1 is highly preferred.

[0177] In addition to the preferred compounds of formula II above, the medium may contain one or more compounds of formula II selected from the compounds of formulas IIA1 to IIA7.

[0178] [ka]

[0179] In the formula, R 2 and X 2 It has the meaning given by formula II or one of the preferred meanings given above and below.

[0180] Preferred compounds are those of formulas IIA1, IIA2, and IIA3, and very preferred are those of formulas IIA1 and IIA2.

[0181] In the compounds of formulas IIA1 to IIA7, R 2 X preferably represents an alkyl group having 1 to 6 C atoms, very preferably ethyl or n-propyl, and 2represents preferably F or OCF3, and very preferably F.

[0182] In another preferred embodiment of the present invention, the medium preferably comprises one or more compounds of formula III selected from the group of formulas III-1 and III-2, preferably formula III-2.

[0183] [ka]

[0184] In the formula, the bases and parameters that appear have the respective meanings given in Equation III above.

[0185] Preferably, the compound of formula III-1 is selected from the group of compounds of formula III-1a and III-1b.

[0186] [ka]

[0187] In the formula, each base that appears has the meaning given above, L 33 and L 34 Each of these independently represents either H or F.

[0188] The compound of formula III-1a is preferably selected from the group of compounds of formula III-1a-1 to III-1a-6.

[0189] [ka]

[0190] In the formula, R 3 It has the meaning given above.

[0191] Preferably, the compound of formula III-2 is selected from the group of compounds of formula III-2a to III-2m.

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] In the formula, each base that appears has the meaning given above, L 35 and L 36 These represent either H or F independently.

[0196] Preferably, the compound of formula II-2a is selected from the group of compounds of formula III-2a-1 to III-2a-4.

[0197] [ka]

[0198] In the formula, R 3 It has the meaning given above.

[0199] The compound of formula III-2b is preferably selected from the group of compounds of formula III-2b-1 and III-2b-2, preferably III-2b-2.

[0200] [ka]

[0201] In the formula, R 3 It has the meaning given above.

[0202] The compound of formula II-2c is preferably selected from the group of compounds of formula III-2c-1 to III-2c-5.

[0203] [ka]

[0204] In the formula, R 3 It has the meaning given above.

[0205] Compounds of formula III-2d and III-2e are preferably selected from the group of compounds of formula III-2d-1, III-2d-2, and III-2e-1.

[0206] [ka]

[0207] In the formula, R 3 It has the meaning given above.

[0208] The compound of formula III-2f is preferably selected from the group of compounds of formula III-2f-1 to III-2f-7.

[0209] [ka]

[0210] The compound of formula III-2g is preferably selected from the group of compounds of formula III-2g-1 to III-2g-7.

[0211] [ka]

[0212] In the formula, R 3 It has the meaning given above.

[0213] The compound of formula III-2h is preferably selected from the group of compounds of formula III-2h-1 to III-2h-5.

[0214] [ka]

[0215] In the formula, R 3 It has the meaning given above.

[0216] The compound of formula III-2i is preferably selected from the group of compounds of formula III-2i-1 to III-2i-3.

[0217] [ka]

[0218] In the formula, R 3 It has the meaning given above.

[0219] The compound of formula III-2j is preferably selected from the group of compounds of formula III-2j-1 to III-2j-3.

[0220] [ka]

[0221] In the formula, R 3 It has the meaning given above.

[0222] The compound of formula III-2k is preferably selected from the group of compounds of formula III-2k-1 to III-2k-6.

[0223] [ka]

[0224] In the formula, R 3 It has the meaning given above.

[0225] The compound of formula III-2l is preferably selected from the group of compounds of formula III-2l-1 to III-2l-6.

[0226] [ka]

[0227] In the formula, R 3 It has the meaning given above.

[0228] The compound of formula III-2m is preferably selected from the compounds of formula III-2m-1.

[0229] [ka]

[0230] Alternatively, in addition to the compounds of formula III-1 and / or III-2, the medium according to the present invention may contain one or more compounds of formula III-3, preferably III-3a.

[0231] [ka]

[0232] In the formula, the base and parameter have the respective meanings given in Equation III above.

[0233] [ka]

[0234] In the formula, R 3 It has the meaning given above.

[0235] In addition to the preferred compound of formula III above, the medium may contain one or more compounds selected from the group consisting of formulas IIIA-1 to IIIA-21.

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] In the formula, R 3 and X 3 The term has the meaning given by formula III or one of the preferred meanings given above and below. Preferred compounds are those of formulas IIIA1, IIIA4, IIIA6, IIIA16, IIIA19 and IIIA20.

[0241] Preferably, the medium according to the present invention comprises one or more compounds of formula IV.

[0242] [ka]

[0243] During the ceremony, R 41 This represents a linear alkyl group having 1 to 12 carbon atoms, or a branched or cyclic alkyl group having 3 to 12 carbon atoms, or a linear alkenyl group having 2 to 12 carbon atoms, or a branched alkenyl group having 3 to 12 carbon atoms, or a cyclic alkenyl group having 5 to 12 carbon atoms (wherein one or more hydrogen atoms may be replaced with fluorine), preferably a linear alkenyl group having 2 to 12 carbon atoms. R 42This represents a linear alkyl or alkoxy group having 1 to 12 carbon atoms, or a branched or cyclic alkyl or alkoxy group having 3 to 12 carbon atoms, or a linear alkenyl group having 2 to 12 carbon atoms, or a branched alkenyl group having 3 to 12 carbon atoms, or a cyclic alkenyl group having 5 to 12 carbon atoms (wherein one or more hydrogen atoms may be replaced with fluorine), preferably a linear alkyl group having 1 to 12 carbon atoms, and very preferably 1 to 7 carbon atoms.

[0244] The total concentration of one or more compounds of formula IV in the medium according to the present invention is preferably in the range of 4% to 35%.

[0245] The compound of formula IV is preferably selected from the group of compounds of formula IV-1 to IV-4, and very preferably from the group of compounds of formula IV-3.

[0246] [ka]

[0247] During the ceremony, Alkyl and alkyl' independently represent alkyl groups having 1 to 7 carbon atoms, preferably 2 to 5 carbon atoms. alkoxy represents an alkoxy having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms. Alkenyl represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 carbon atoms. 'alkenyl' represents an alkenyl group having 2 to 5 carbon atoms, preferably 2 to 4 carbon atoms, and particularly preferably 2 to 3 carbon atoms.

[0248] Preferably, the medium contains one or more compounds of formula IV-1, preferably selected from compounds of formula IV-1-1 to IV-1-6.

[0249] [ka]

[0250] Preferably, the medium according to the present invention comprises one or more compounds of formula IV-2-1 and / or IV-2-2.

[0251] [ka]

[0252] Preferably, the medium according to the present invention comprises, very preferably, compounds of formula IV-3-1 to IV-3-7, and in particular, compounds of formula IV-3 selected from compounds of formula IV-3-2 and / or IV-3-7.

[0253] [ka]

[0254] Preferably, the medium according to the present invention comprises formula IV-4, which is selected from compounds of formula IV-4-1 and IV-4-2.

[0255] [ka]

[0256] Preferably, the medium according to the present invention comprises one or more compounds of formula IVa and / or IVb.

[0257] [ka]

[0258] During the ceremony R 41 and R 42 These terms have meanings defined above in equation IV, independently of each other. [ka] This represents, Z 4-CH2CH2-, -CH=CH-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -C4H8-, or -CF=CF-.

[0259] The total concentration of one or more compounds represented by formula IVa in the medium according to the present invention is preferably in the range of 5% to 15%.

[0260] The total concentration of one or more compounds represented by formula IVb in the medium according to the present invention is preferably in the range of 1% to 10%.

[0261] The preferred compound of formula IVa is selected from the compounds of formulas IVa-1 to IVa-4.

[0262] [ka]

[0263] During the ceremony Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other.

[0264] The medium according to the present invention preferably comprises at least one compound of formula IVa-2.

[0265] The preferred compound of formula IVb is selected from the compounds of formulas IVb-1 to IVb-3.

[0266] [ka]

[0267] During the ceremony Alkyl and alkyl * Each of these represents a linear alkyl group having 1 to 6 carbon atoms independently of each other. alkenyl and alkenyl *Each of these represents a linear alkenyl group having 2 to 6 carbon atoms independently of each other.

[0268] Of the compounds of formulas IVb-1 to IVb-3, the compound of formula IVb-2 is particularly preferred.

[0269] Particularly preferred compounds of formula IVb are selected from the following compounds.

[0270] [ka]

[0271] The medium according to the present invention particularly preferably contains compound IVb-2-4.

[0272] In a preferred embodiment, the medium according to the present invention comprises one or more compounds of formula V.

[0273] [ka]

[0274] During the ceremony, R 51 , R 52 This represents an alkyl group having 1 to 7 carbon atoms, an alkoxy group having 1 to 7 carbon atoms, or an alkoxyalkyl group having 2 to 7 carbon atoms, an alkenyl group, or an alkenyloxy group. [ka] This represents, Z 51 , Z 52 These each independently represent -CH2-CH2-, -CH2-O-, -CH=CH-, -C≡C-, -COO-, or a single bond. n is either 1 or 2.

[0275] The compound of formula V is preferably selected from the compounds of formulas V-1, V-2, V-3, and V-4.

[0276] [ka]

[0277] In the formula, each group has the meaning described above for formula V.

[0278] The total concentration of one or more compounds of formula V in the medium according to the present invention is preferably in the range of 1% to 10%.

[0279] The compound of formula V-1 is preferably selected from the compounds of formulas V1-1 to V1-8.

[0280] The compound of formula V-2 is preferably selected from the compounds of formulas V2-1 to V2-4.

[0281] The compound of formula V-3 is preferably selected from the compounds of formulas V3-1 to V3-5.

[0282] [ka]

[0283] [ka]

[0284] In the formula, R 51 and R 52 This has the meaning shown for equation V above. R 51 and R 52 Preferably, each independently represents a linear alkyl group having 1 to 7 carbon atoms, or an alkenyl group having 2 to 7 carbon atoms.

[0285] A highly preferred compound of formula V-2-1 is selected from the compounds of formulas V-2-1a to V-2-1g.

[0286] [ka]

[0287] A very preferred compound of formula V-2-2 is selected from the compounds of formulas V-2-2a to V-2-2i.

[0288] [ka]

[0289] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VI-1 to VI-9.

[0290] [ka]

[0291] During the ceremony, R 7 Each of these independently of the other is R in claim 5 2A It has one of the meanings shown, w and x each represent 1 through 6.

[0292] The total concentration of one or more compounds of formulas VI-1 to VI-9 in the medium according to the present invention is preferably in the range of 1% to 10%.

[0293] In a preferred embodiment of the present invention, the medium further comprises one or more compounds of formulas VII-1 to VII-21.

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] During the ceremony, R represents a linear alkyl or alkoxy group having 1 to 6 C atoms, (O) represents -O- or a single bond, m is 0, 1, 2, 3, 4, 5 or 6, n is 0, 1, 2, 3 or 4, and R preferably represents methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, or pentoxy.

[0298] Compounds of formulas VII-1, VII-2, VII-4, VII-20, and VII-21 are particularly preferred. In these compounds, R preferably represents an alkyl group having 1 to 5 carbon atoms, and more preferably an alkoxy group. In the compound of formula VII-20, R preferably represents an alkyl or alkenyl group, particularly an alkyl group. In the compound of formula VII-21, R preferably represents an alkyl group.

[0299] The total concentration of one or more compounds of formulas VII-1 to VI-21 in the medium according to the present invention is preferably in the range of 1% to 10%.

[0300] In one embodiment, the medium includes the following.

[0301] • One or more compounds of formula I in a total concentration within the range of 20% to 70%, preferably 25% to 65%, and more preferably 30% to 55%.

[0302] and • One or more compounds of formula T in a total concentration within the range of 1% to 25%, preferably 2% to 20%, and more preferably 3% to 17%.

[0303] and Preferably, one or more compounds of formula II and / or III, more preferably one or more compounds of formula II, provided that the total concentration of the compounds of formula II and / or III is in the range of 7% to 45%, preferably 10% to 40%, more preferably 12% to 35%; the compounds of formula II are preferably selected from formula II-1a, II-1g, and II-3d; the medium very preferably contains one or more compounds of formula II-1a and / or II-1g at a total concentration of 4% to 20%, particularly 5% to 17%, and one or more compounds of formula II-3d at a total concentration of 4% to 20%, particularly 5% to 18%;

[0304] and / or Preferably, one or more compounds of formula IV, more preferably formula IV-3, and optionally one or more compounds of formula IV-2, wherein the total concentration of the formula IV compounds is in the range of 4-35%, preferably 6-30%, and very preferably 7-27%; or the total concentration of compounds of one or more compounds of formula IV and IVa, preferably formula IV-3 and IVa-2, is in the range of 10-45%, more preferably 13-40%, and very preferably 16-35%.

[0305] In a preferred embodiment, 589 nm (Na D The birefringence (Δn) of the liquid crystal medium according to the present invention at 20°C is in the range of 0.180 to 0.400, preferably 0.190 to 0.310, more preferably 0.200 to 0.300, and very preferably 0.210 to 0.270.

[0306] In a preferred embodiment, the liquid crystal medium according to the present invention has a positive dielectric anisotropy Δε in the range of 2.0 to 15.0, preferably 3.0 to 13.0, and particularly 5.0 to 12.0.

[0307] In a preferred embodiment of the present invention, the liquid crystal medium has a transparent point at 80°C or higher, preferably 90°C or higher, particularly preferably 92°C or higher, and very particularly preferably 93°C or higher.

[0308] The nematic phase of the medium according to the present invention preferably ranges from at least 0°C to 70°C or higher. It is advantageous for the medium according to the present invention to exhibit an even wider nematic phase range, preferably at least -10°C to 80°C or higher, very preferably at least -20°C to 85°C or higher, particularly at least -30°C to 90°C or higher, and very particularly preferably at least -40°C to 93°C or higher.

[0309] The adjustability τ of the medium according to the present invention, measured at 20°C and 19GHz, is 0.200 or higher, preferably 0.210 or higher.

[0310] The preferred material quality (η) of the liquid crystal material is 6 or higher, preferably 8 or higher, very preferably 10 or higher, and especially 15 or higher.

[0311] In the corresponding component, preferred liquid crystal material has a phase shift performance of 15° / dB or more, preferably 20° / dB or more, preferably 30° / dB or more, preferably 40° / dB or more, preferably 50° / dB or more, particularly preferably 80° / dB or more, and very particularly preferably 100° / dB or more.

[0312] An electronic component is provided, comprising a first substrate and a second substrate facing each other, wherein the liquid crystal medium according to the present invention is sandwiched between the first and second substrates. To supply a potential across the liquid crystal material and drive the liquid crystal in a predetermined arrangement, one electrode is provided on each substrate, or two electrodes are provided on only one of the substrates.

[0313] In one embodiment, the electronic component is capable of operating in the microwave region of the electromagnetic spectrum. In this specification, the liquid crystal medium within the component functions as a tunable dielectric and can be used in high-frequency technologies.

[0314] Preferred components include liquid crystal antenna elements, phase shifters, adjustable filters, adjustable metamaterial structures, matched networks, or varactors.

[0315] A microwave antenna array is provided that includes one or more of the aforementioned components.

[0316] In another embodiment, the electronic component is an optical component, preferably a transmissive SLM, capable of operating in the visible or infrared range of the electromagnetic spectrum.

[0317] In another preferred embodiment, the optical component is a reflective SLM.

[0318] In the optical device component according to the present invention, the optical modulation element (i.e., pixel) of the spatial light modulator is a cell containing liquid crystal as described in claim 1. That is, the spatial light modulator is a liquid crystal device, and the optically active component is liquid crystal. Each liquid crystal cell is configured to selectively provide a plurality of optical modulation levels. That is, each liquid crystal cell is always configured to operate at one optical modulation level selected from a plurality of possible optical modulation levels. Each liquid crystal cell is dynamically reconfigurable to a plurality of optical modulation levels and different optical modulation levels.

[0319] LCOS devices provide a high-density array of optical modulators or pixels within a small aperture (e.g., a few centimeters wide). Typically, pixels are about 10 microns or less, resulting in diffraction angles of a few degrees, meaning the optical system can be made compact. LCOS devices are typically reflective, meaning the circuitry driving the pixels in an LCOS SLM can be embedded beneath the reflective surface. This results in a higher aperture ratio. In other words, the pixels are densely packed, meaning there is little dead space between them. This is advantageous because it reduces optical noise in the regenerated field. LCOS SLMs use a silicon backplane, which has the advantage of optically flat pixels. This is particularly important for phase modulation devices.

[0320] Therefore, referring to Figure 1 in a preferred embodiment, a reflective spatial light modulator, in particular an LCoS device 100 is provided, comprising a transparent glass layer 110 having transparent electrodes 120, a mirror 150 mounted on a silicon CMOS back substrate 160, and a liquid crystal material 140 as defined above, sandwiched between PCB mountings (not shown). The mirror is divided into a two-dimensional array of individually addressable pixels. Each pixel is individually driveable by a voltage signal to give a local phase change to at least one polarization component of an optical signal, thereby providing a two-dimensional array of phase manipulation regions. Pre-alignment of the liquid crystal 140 is provided by alignment layers 131 and 132.

[0321] The LCOS devices described herein are useful for integration into optical devices. The LCOS SLMs described reflect and output spatially modulated light. Reflective LCOS SLMs have the advantage of high fill factor (typically greater than 90%) and high resolution as a result of the signal lines, gate lines, and transistors being located beneath the mirror surface. Another advantage of using reflective LCOS spatial light modulators is that the thickness of the liquid crystal layer can be halved compared to the thickness required when using transmissive devices. This significantly improves the switching speed of the liquid crystal (a significant advantage in motion projection). However, the teachings of this disclosure can be equally carried out using transmissive LCOS SLMs.

[0322] Examples of devices including optical components according to the present invention include a holographic projector, a head-up display including at least one holographic projection channel, a driver monitoring system for a head-up display, more preferably an infrared holographic projector for a driver monitoring system for a head-up display, an augmented reality head-up display, an "AR-HUD" (including eye-tracking or head-tracking), an image generation unit, and an integrated infrared holographic illumination device for head-tracking or eye-tracking.

[0323] A spatial light modulator may be used to display diffraction patterns, including computer-generated holograms. If the hologram is a phase-limited hologram, a spatial light modulator that modulates the phase is required. If the hologram is a fully complex hologram, a spatial light modulator that modulates both the phase and amplitude may be used, or a first spatial light modulator that modulates the phase and a second spatial light modulator that modulates the amplitude may be used.

[0324] Other preferred devices include infrared imagers, wavelength-selective switches, LCoS-SLMs, LIDAR systems, wavelength-division multiplex (WDM) systems, reconfigurable optical add-drop multiplexers (ROADMs), and non-mechanical beam steering, such as the steerable electro evanescent optical refraction (SEEOR) prism, as published in the paper "Agile Nonmechanical Beam Steering" by P. McManamon, 2006, Opt. Photon. News, Vol. 17 (No. 3): pp. 24-29.

[0325] The technology incorporates an SLM device and a red-green-blue (RGB) light source. The red-green-blue (RGB) light source is configured to emit red, green, and blue light simultaneously or at different times (e.g., a time-multiplexed RGB LED or laser diode). As an example, the light source is an RGB light source that uses a red, green, and blue micro-LED array as proposed, for example, in European Patent Application Publication No. 3539157.

[0326] RGB refers to the three primary colors of light: red, green, and blue, which may form other colors and white. A conventional single LED may only transmit monochromatic (monochromatic) light, which is one of these three primary colors. To create more colors, three LEDs can be used together to create an RGB mix. An RGB LED often consists of three monochromatic LEDs, typically red, green, and blue, placed close to each other within the same package. When all LEDs in an RGB-LED emit light at proportionally equal luminous intensity and the appropriate type of optics is used, the light emitted from an RGB-LED appears white to the human eye.

[0327] Using an RGB light source avoids the unavoidable exposure of liquid crystals to UV light that occurs when using conventional light sources such as cold cathode fluorescent lamps.

[0328] Therefore, according to another aspect of the present invention, an optical device is provided that includes an RGB light source and the optical component, wherein the phase of the incident light signal from the RGB light source is modulated by the component during operation of the optical device.

[0329] According to another aspect of the present invention, a method for spatially modulating visible or infrared light, i) Providing an optical component comprising first and second substrates facing each other and each having a surface, wherein the first substrate comprises at least one first electrode and the second substrate comprises at least one second electrode, and the component further comprises a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises one or more compounds selected from the compounds of formulas I, T, and S1 shown above, ii) A step of receiving incident visible or infrared light on the surface of the optical component, iii) A step of applying a predetermined voltage to each of the individual electrodes formed on the first substrate in order to modulate the refractive index of the liquid crystal layer. A method including this is provided.

[0330] According to another aspect of the present invention, a method for manufacturing an optical phase modulator, a) A step of providing a first substrate having a first electrode, which may have a two-dimensional array of individually electrically driveable cells, b) A step of depositing a liquid crystal medium as defined in claim 1 onto a first substrate, c) A step of mounting a second substrate having a second electrode onto a liquid crystal material. A method is provided that includes at least the following.

[0331] The liquid crystal medium according to the present invention consists of a plurality of compounds, preferably 3 to 30 types, more preferably 4 to 20 types, and very preferably 4 to 16 types. These compounds are mixed by conventional methods. Generally, a desired amount of compound to be used in smaller quantities is dissolved in a larger quantity of the compound to be used. When the temperature is higher than the transparency point of the compound to be used at higher concentrations, it is particularly easy to observe the completion of the dissolution process. However, it is also possible to prepare the medium using other conventional methods, such as so-called premixes which may be homogeneous or eutectic mixtures of components, or using a so-called "multi-bottle" system, for example.

[0332] In the present invention and especially in the following examples, the structure of the mesogenic compound is indicated by an abbreviation or acronym. In these acronyms, the chemical formula is abbreviated as follows using Tables A to C below. All groups C n H 2n+1 , C m H 2m+1 and C l H 2l+1 and C n H2 n-1 , C m H 2m-1 and C l H 2-1 The terms represent a linear alkyl or alkylene, respectively, having n, m, and l carbon atoms, where n and m are independently 1, 2, 3, 4, 5, 6, or 7, and l is 1, 2, or 3. Table A lists the codes used for the ring elements of the core structure of the compounds, while Table B shows the linking and terminal groups. Table C shows exemplary structures of the compounds, along with their respective abbreviations.

[0333] <Table A: Environmental Elements>

[0334] Table 1

[0335] Table 2

[0336] Table 3

[0337] Table 4

[0338] Table 5

[0339] Table 6

[0340] <Table B: Link Base>

[0341] Table 7

[0342] <Table B: Terminal Groups>

[0343] Table 8

[0344] Table 9

[0345] In the table, n and m represent integers, respectively, and the three dots "..." are spaces for other abbreviations from this table.

[0346] The branching lateral chain bases are numbered starting from the position next to ring (1) where the longest chain is selected, with smaller numbers indicating the length of the branch and superscript numbers in parentheses indicating the position of the branch, e.g., below.

[0347] [ka]

[0348] The following table shows exemplary structures along with their respective abbreviations. These are provided to illustrate the meaning of the abbreviation rules. They represent compounds that are more preferably used.

[0349] <Table C: Exemplary Structure> The following exemplary structures are examples and compounds that are preferably used additionally in the medium.

[0350] [Table 10]

[0351] [Table 11]

[0352] [Table 12]

[0353] [Table 13]

[0354] [Table 14]

[0355] Table 15

[0356] Table 16

[0357] Table 17

[0358] Table 18

[0359] Table 19

[0360] Table 20

[0361] Table 21

[0362] Table 22

[0363] Table 23

[0364] Table 24

[0365] Table 25

[0366] [Table 26]

[0367] In the formula, m and n are the same or different, and are 1, 2, 3, 4, 5, 6, or 7.

[0368] Preferably, the medium according to the present invention comprises one or more compounds selected from the compounds in Table C.

[0369] The following table, Table D, shows exemplary compounds that can be used as additional stabilizers in the mesogenic medium according to the present invention. The total concentration of these and similar compounds in the medium is preferably 5% or less.

[0370]

[0371] [Table 27]

[0372] [Table 28]

[0373] [Table 29]

[0374] In a preferred embodiment of the present invention, the mesogenic medium comprises one or more compounds selected from the group of compounds in Table D.

[0375] The mesogenic medium according to this application preferably comprises two or more compounds, preferably four or more compounds, selected from the group consisting of the compounds in the table above.

[0376] Preferably, the medium contains one or more chiral dopants in a concentration of more than 0% to 5%, preferably 0.01% to 4%, more preferably 0.1% to 3%, very preferably 0.2% to 2%, and especially 0.3% to 1%.

[0377] All mixtures according to the present invention are nematic. The liquid crystal media according to the present invention preferably have a nematic phase within the preferred range given above. In this specification, the expression "having a nematic phase" means, on the one hand, that no smectic phase and crystallization are observed at low temperatures at the corresponding temperature, and on the other hand, that no transition from the nematic phase to the isotropic phase occurs upon heating. At high temperatures, the point of transparency in the capillary is measured by conventional methods. Low-temperature studies are performed at the corresponding temperature using a fluid viscometer and confirmed by the storage of bulk samples: the bulk storage stability (LTS) of the media according to the present invention at a given temperature T is determined by visual inspection. 2 g of the media under consideration is filled into a suitably sized sealed glass container (bottle) placed in a refrigerator at the given temperature. The bottle is checked at predetermined time intervals for the occurrence of the smectic phase and crystallization. Two bottles are stored for each material and each temperature. The test is terminated if crystallization or the appearance of a smectic phase is observed in at least one of the two corresponding bottles, and the last test time before the appearance of a higher phase is recorded as the respective storage stability. The test is ultimately terminated after 1000 hours, i.e., an LTS value of 1000 hours, meaning that the mixture is stable at a given temperature for at least 1000 hours.

[0378] The response time is the time (t) for the change in relative tuning from 0% to 90% for each electro-optic response. 90 -t0), i.e., delay time (t 10 (τ) including the rising time (t0) on ) as the time (t) for the change in relative tuning for the electro-optic response, from 100% back to 10%. 100 -t 10 ) with respect to decay time (τ off ) as, and total response time (τ total =τ on +τoff They are given as follows:

[0379] mp represents the melting point, T (N,I) The transparent point of the liquid crystal material is expressed in Celsius. Furthermore, K represents the crystalline solid state, S represents the smectic phase (the exponent indicates the type of phase), N represents the nematic state, Ch represents the cholesteric phase, I represents the isotropic phase, and T represents the transparent point of the liquid crystal material in Celsius. g The symbol represents the glass transition temperature. The number between the two symbols indicates the conversion temperature in Celsius.

[0380] For example, all temperatures, such as the melting point T(C,N) or T(C,S), the transition from the smectic (S) phase to the nematic (N) phase T(S,N), and the transparency point T(N,I) of liquid crystals, are cited in degrees Celsius. All temperature differences are cited in degrees of difference.

[0381] The host mixture used to determine the optical anisotropy Δn of a single compound is the commercially available mixture ZLI-4792 (Merck). The dielectric anisotropy Δε is determined using the commercially available mixture ZLI-2857. The physical data for each compound under consideration is obtained from the change in the dielectric constant of the host mixture after the addition of the compound under consideration, and the compound used is extrapolated to 100%. Generally, 10% of the compound under consideration is dissolved in the host mixture, depending on its solubility.

[0382] Unless otherwise indicated, part or percentage data represents parts by weight or percentage by weight.

[0383] Above and below: V0 represents the capacitance threshold voltage [V] at 20°C. n e This represents the anomalous refractive index at 20°C and 589nm. n0 represents the typical refractive index at 20°C and 589nm. Δn represents the optical anisotropy at 20°C and 589 nm. ε ⊥ This represents the dielectric constant perpendicular to the director at 20°C and 1kHz. ε ∥This represents the dielectric constant parallel to the director at 20°C and 1kHz. Δε represents the dielectric anisotropy at 20°C and 1kHz. cl.p. and T(N,I) represent the point of transparency [°C]. γ1 represents the rotational viscosity [mPa·s] measured at 20℃, K1 represents the elastic constant [pN] for "splay" deformation at 20°C. K2 represents the elastic constant [pN] for "twist" deformation at 20°C. K3 represents the elastic constant [pN] for "bend" deformation at 20°C, and LTS (low-temperature stability) refers to the low-temperature stability (nematic phase) determined in the test cell or bulk, as specified.

[0384] In this invention, the term "threshold voltage" refers to the capacitance threshold (V0), also known as the Frederick's threshold, unless otherwise specified. Furthermore, in the example, although generally typical, 10% relative contrast (V0) is used. 10 The optical threshold for ) may also be indicated.

[0385] The display used for measuring capacitance threshold voltage consists of two flat, parallel glass outer plates separated by a 20 μm gap. Each outer plate has an electrode layer on the inside and an unrubbed polyimide orientation layer on top, which causes homeotropic edge orientation of liquid crystal molecules.

[0386] The display or test cell used for measuring the tilt angle consists of two flat, parallel glass outer plates separated by a 4 μm gap, each having an electrode layer on the inside and a polyimide orientation layer on top, however, the two polyimide layers are rubbed in opposite parallel directions to each other, resulting in homeotropic edge orientation of liquid crystal molecules.

[0387] The tilt angle is typically determined using an Axometrics Mueller matrix polarimeter, "AxoScan." In this specification, a low value (i.e., a large deviation from 90°) corresponds to a large tilt.

[0388] Unless otherwise specified, the term “tilt angle” refers to the angle between the LC director and the substrate, and “LC director” refers to the preferred orientation direction of the optical principal axis of LC molecules in a uniformly oriented layer of LC molecules. In the case of calamitic, uniaxial, positively birefringent LC molecules, it corresponds to their molecular long axis.

[0389] Unless otherwise clearly stated, VHR is 20℃ (VHR 20 ) and after 5 minutes in a 100°C oven (VHR 100 This is determined in the equipment model LCM-1(O0004) commercially available from Toyo Technica Co., Ltd. in Japan. Unless otherwise specified, the voltage used has a frequency in the range of 1Hz to 60Hz.

[0390] The stability against UV irradiation will be examined using the Heraeus "Suntest CPS+" system from Germany, which utilizes a xenon lamp NXE1500B. Sealed test cells will be irradiated for 2.0 hours without additional heating unless otherwise specified. The irradiation power in the wavelength range of 300nm to 800nm ​​will be 765W / m². 2 V is used. A UV "cutoff" filter with an edge wavelength of 310 nm is used to simulate the so-called window glass mode. In each series of experiments, at least four test cells are examined for each condition, and the results are shown as the average of the corresponding individual measurements.

[0391] For example, the decrease in voltage holding ratio (ΔVHR) typically caused by UV irradiation or exposure to LCD backlights is determined according to the following equation (1).

[0392]

number

[0393] The ion density for calculating resistivity is measured using a VHR test cell with a 3.2 μm cell gap and AL16301 polyimide (JSR Corporation, Japan), using a commercially available LC material characterization system Model 6254 from Toyo Technica Co., Ltd., Japan. The measurement is performed after storage in an oven at 60°C or 100°C for 5 minutes.

[0394] The so-called "HTP (helical twisting power)" represents the helical twisting force of an optically active or chiral substance in an LC medium (unit: μm). Unless otherwise specified, HTP is measured at 20°C in the commercially available nematic LC host mixture MLC-6260 (Merck).

[0395] The transparency point is measured using a Mettler Thermosystem FP900. Optical anisotropy (n) is measured using an Abbe refractometer H005 (sodium spectral lamp Na10, 589 nm, at 20°C). Dielectric anisotropy (Δε) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Start-up voltage (V0) is measured at 20°C using an LCR meter E4980A / Agilent (G005) (ε-parallel cell equipped with JALS2096-R1). Rotational viscosity (γ1) is measured at 20°C using a Toyo Technica LCM-2 (0002) (gamma 1 negative cell equipped with JALS-2096-R1). The elastic constant (K1, spray) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1). K3: The elastic constant (K3, bend) is measured at 20°C using an LCR meter E4980A / Agilent Corporation (G005) (ε-parallel cell equipped with JALS2096-R1).

[0396] Unless otherwise explicitly stated, all concentrations in this application are expressed as weight percentages with respect to the entire corresponding mixture containing all solid or liquid crystal components, excluding the solvent. All physical properties are determined in accordance with "Merck Liquid Crystals, Physical Properties of Liquid Crystals," published November 1997, Merck AG, Germany, and a temperature of 20°C is applied unless otherwise explicitly stated.

[0397] The characteristics of liquid crystal media in the microwave frequency range are examined as described in "Cavity Perturbation Method for Characterization of Liquid Crystals up to 35GHz" by A. Penirschke et al., 34th European Microwave Conference - Amsterdam, pp. 545-548. Furthermore, this is compared with "Direct Simulation of Material Permittivites" by A. Gaebler et al., 12MTC2009 - International Instrumentation and Measurement Technology Conference, Singapore, 2009 (IEEE), pp. 463-467, and German Patent Application Publication No. 10 2004 029 429, both of which describe measurement methods in similar detail.

[0398] Liquid crystal is introduced into a polytetrafluoroethylene (PTFE) or quartz capillary. The capillary has an inner diameter of 0.5 mm and an outer diameter of 0.78 mm. The effective length is 2.0 cm. The filled capillary is introduced into the center of a cylindrical cavity with a resonant frequency of 19 GHz. This cavity has a length of 11.5 mm and a radius of 6 mm. An input signal (signal source) is then applied, and the output signal result is recorded using a commercially available vector network analyzer (N5227A PNA Microwave Network Analyzer, Keysight Technologies, USA). For other frequencies, the dimensions of the cavity are adapted accordingly.

[0399] Using the change in resonant frequency and the Q factor between measurements with and without a liquid crystal-filled capillary, the dielectric constant and loss angle at the corresponding target frequency are determined using equations 10 and 11 as described on pages 545-548 of the aforementioned publication, A. Penirschke et al., 34th European Microwave Conference - Amsterdam.

[0400] The values ​​of the characteristic components perpendicular and parallel to the liquid crystal director are obtained by the orientation of the liquid crystal in a magnetic field. For this purpose, a magnetic field from a permanent magnet is used. The strength of the magnetic field is 0.35 Tesla.

[0401] Dielectric anisotropy in the microwave region is defined as follows:

[0402]

number

[0403] Adjustability (τ) is defined as follows:

[0404]

number

[0405] Material quality (η) is defined as follows:

[0406]

number

[0407] In the equation, the maximum dielectric loss is shown below.

[0408]

number

[0409] The present invention will be described in detail by the following non-limiting embodiments.

[0410] <Mixture example M1>

[0411] [Table 30]

[0412] <Mixture example M2>

[0413] [Table 31]

[0414] <Mixture example M3>

[0415] [Table 32]

[0416] <Mixture example M4>

[0417] [Table 33]

[0418] <Mixture example M5>

[0419] [Table 34]

[0420] <Mixture example M6>

[0421] [Table 35]

[0422] <Mixture example M7>

[0423] [Table 36]

[0424] <Mixture example M8> Mixture example M8 consists of 99.975% of mixture example 1 and 0.025% of compounds S3-5.

[0425] [ka]

[0426] <Mixture example M9> Mixture example M9 consists of 99.97% of mixture example 2 and 0.03% of compound S3-6.

[0427] [ka]

[0428] <Mixture example M10> Mixture example M10 consists of 99.97% of mixture example 1 and 0.03% of compound S3-2-1.

[0429] [ka]

[0430] <Mixture example M11> Mixture example M11 consists of 99.98% of mixture example M1 and 0.02% of the compound of formula S2-1a-2.

[0431] [ka]

[0432] <Mixture example M12> Mixture example M12 consists of 99.985% of mixture example M1 and 0.015% of the compound of formula S2-3a-1.

[0433] [ka]

[0434] <Mixture example M13> Mixture example M13 consists of 99.98% of mixture example M1 and 0.02% of the compound of formula S2-1a-2.

[0435] [ka]

[0436] <Mixture example M14> Mixture example M14 consists of 99.985% of mixture example M1 and 0.015% of the compound of formula S2-3a-1.

[0437] [ka]

[0438] <Mixture example M15> Mixture example M15 consists of 99.97% of mixture example M2 and 0.03% of the compound of formula S3-4-1.

[0439] [ka]

Claims

1. a) A liquid crystal medium comprising one or more compounds of formula I and b) one or more compounds of formula T. 【Chemistry 1】 (In the formula, R １１ and R １２ This refers to alkyl or alkoxy molecules having the same or different H atoms, 1 to 12 C atoms, or alkenyl, alkenyloxy, or alkoxyalkyl molecules having 2 to 12 C atoms (provided that one or more CH atoms are present). ２ The basis is, 【Chemistry 2】 This represents (which may be replaced by , and in the group, one or more H atoms may be replaced by fluorine), L １１ , L １２ , L １３ H, CH are the same or different. ３ , represents Cl or F, A １１ is phenylene-1,4-diyl (where one or two CH groups may be replaced by N, and one or more H atoms may be replaced by halogen, CN, CH ３ , CHF ２ , CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ ), cyclohexane-1,4-diyl or cyclohexene-1,4-diyl (where one or two non-adjacent CH ２ groups may be independently replaced by O and / or S, and one or more H atoms may be replaced by F) or bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl or 1,3-dioxane-2,5-diyl (where one or more H atoms may be replaced by F), A １２ This is phenylene-1,4-diyl (where one or two CH groups may be replaced with N, and one or more H atoms may be halogens, CN, or CH). ３ CHF ２ ,CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ (may be replaced by) or cyclohexane-1,4-diyl or cyclohexene-1,4-diyl (wherein one or two non-adjacent CH4s are each) ２ The groups may be independently replaced by O and / or S, and one or more H atoms may be replaced by F. Z １ This is a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -CF=CF- or -CH=CHCH ２ Represents O-, n is either 0 or 1. 【Transformation 3】 (In the formula, R Ｔ１ and R Ｔ２ These are identical or different halogens, -CN, -NCS, linear alkyl or alkoxy having 1 to 15 carbon atoms, linear alkenyl or alkenyloxy having 2 to 15 carbon atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15 carbon atoms (one or more CH in the group) ２ The group is designed so that the oxygen atoms are not directly bonded to each other. 【Chemistry 4】 -C≡C-, -CF ２ O-, -OCF ２ -, -CH=CH-, -O-, -CO-O- or -O-CO- may be substituted, and one or more H atoms may be replaced by halogens. R Ｔ３ This includes F, -CN, linear alkyl or alkoxy having 1 to 5 carbon atoms, linear alkenyl or alkenyloxy having 2 to 5 carbon atoms, or branched alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 5 carbon atoms (with CH in the group) ２ The base is 【Transformation 5】 This represents a compound (which may be replaced by a halogen, however one or more H atoms may be replaced by halogens), A ０ A １ and A ２ Each of these is independently phenylene-1,4-diyl (where one or two CH groups may be replaced by N, and one or more H atoms may be halogens, CN, or CH). ３ CHF ２ ,CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ (may be replaced by) cyclohexane-1,4-diyl (wherein one or two non-adjacent CH4s) ２ The groups may be independently replaced by O and / or S, and one or more H atoms may be replaced by F), representing cyclohexene-1,4-diyl, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, Z １ and Z ２ Each of them independently of the other is -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -CO-O-, -O-CO-, -C ２ H ４ -, -C ２ F ４ -, -CF ２ CH ２ -ien-CH ２ CF ２ -, -CFHCFH-, -CFHCH ２ -ien-CH ２ CFH-, -CF ２ CFH-, -CFHCF ２ -, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF-, -C≡C- or single bond, n is 0, 1, 2, or 3. m is 0, 1, 2, or 3.

2. The liquid crystal medium according to claim 1, comprising one or more compounds selected from the group of compounds of formulas S1, S2, and S3. 【Transformation 6】 (In the formula, R Ｓ１ and R Ｓ２ In each instance, the group is identical or different in its appearance, consisting of H or a linear alkyl group having 1 to 25 carbon atoms or a branched alkyl group having 3 to 25 carbon atoms (the group is unsubstituted or CN or CF ３ It is monosubstituted or at least monosubstituted with a halogen, provided that it contains one or more CH ２ Each group is formed such that the O and / or S atoms are not directly bonded to one another. 【Transformation 7】 -O-, -S-, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C- may be substituted.) or halogen, each having 6, 5, 7 or 7 to 25 carbon atoms, representing an aryl, heteroaryl, alkylaryl or arylalkyl (each group is unsubstituted or monosubstituted or polysubstituted with an alkyl or halogen having 1 to 6 C atoms). s is 0, 1 or 2, and t is 0, 1, 2, or 3. q is 1, 2, 3 or 4, G represents a hydrocarbon group having 1 to 60 carbon atoms, which may be linear, branched, or cyclic, and the group may be unsubstituted or composed of CN or CF ３ It is monosubstituted or at least monosubstituted with a halogen, provided that it contains one or more CH ２ The groups are arranged such that the O or S atoms are not directly bonded to each other, and are -O-, -S-, and -NR respectively. ０ -, -CO-, -CO-O-, -O-CO-, -O-CO-O-, -CH=CH- or -C≡C- can be substituted, R ０ This represents an alkyl group having H or 1 to 6 C atoms. R ２ H, -O ・ -OH represents a linear alkyl or alkoxy having 1 to 12 carbon atoms, or a branched or cyclic alkyl having 3 to 25 carbon atoms, or an arylalkoxy having 7 to 25 carbon atoms. R ２１ and R ２２ R represents a linear alkyl group having 1 to 12 identical or different carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms, or R ２１ and R ２２ These, together with the carbon atoms to which they are linked, form a cycloalkyl group having 5 to 12 carbon atoms. R ２３ and R ２４ R represents a linear alkyl group having 1 to 12 identical or different carbon atoms, or a branched alkyl group having 3 to 12 carbon atoms, or R ２３ and R ２４ These, together with the carbon atoms to which they are linked, form a cycloalkyl group having 5 to 12 carbon atoms. Z ２ represents, independently at each occurrence, -O-, -C(O)O-, -OC(O)- or a single bond, R ＳＴ This includes H, alkyl or alkoxy having 1 to 12 carbon atoms, or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12 carbon atoms (provided that one or more CH ２ The base is 【Transformation 8】 This represents a compound (which may be replaced by fluorine, however one or more H atoms may be replaced by fluorine), Z ＳＴ is, independently of each other, -CO-O-, -O-CO-, -CF ２ O-, -OCF ２ -, -CH ２ O-, -OCH ２ -, -CH ２ -, -CH ２ CH ２ -, -(CH ２ ) ４ -, -CH=CH-CH ２ O-, -C ２ F ４ -, -CH ２ CF ２ -, -CF ２ CH ２ -, -CF=CF-, -CH=CF-, -CF=CH-, -CH=CH-, -C≡C- or a single bond, 【Chemistry 9】 Each occurrence represents the same or different cyclohexane-1,4-diyl, cyclohexene-1,4-diyl, pyran-2,5-diyl, or 1,3-dioxane-2,5-diyl (where one or more H atoms may be replaced by F), p is 0, 1, or 2.

3. A liquid crystal medium according to claim 1 or 2, comprising one or more compounds selected from the group of compounds of formula S2-1 and S2-2. 【Chemistry 10】 (In the formula, G represents a divalent aliphatic group having 1 to 20 carbon atoms or an alicyclic group having 3 to 20 carbon atoms.)

4. A liquid crystal medium according to any one of claims 1 to 3, comprising one or more compounds selected from the group of compounds of formula I-1 to I-3. 【Chemistry 11】 (In the formula, R １１ , R １２ Z １ , L １１ , L １２ and L １３ (This has the meaning given in claim 1.)

5. A liquid crystal medium according to any one of claims 1 to 4, comprising one or more compounds of formula T-1 to T-6. 【Chemistry 12】 (In the formula, R Ｔ１ , R Ｔ２ and R Ｔ３ This has the meaning shown in claim 1, L stands for halogen, CN, CH ３ CHF ２ ,CH ２ F, CF ３ , OCH ３ , OCHF ２ or OCF ３ This represents, r, s, and t are independently 0, 1, 2, 3, or 4.

6. A liquid crystal medium according to any one of claims 1 to 5, comprising one or more compounds of formula S1-1. 【Chemistry 13】 (In the formula, R Ｓ１ represents H, F, or Cl, and R ２１ and R ２２ This refers to linear or branched alkyl groups having the same or different H or 1 to 12 carbon atoms (provided that one or more CH ２ The groups are arranged such that the oxygen atoms do not directly bond to each other, independently of each other. 【Chemistry 14】 (This can be replaced with -O-, -CO-O-, -O-CO-, -CH=CH-, or -C≡C-.) Or it represents an aryl or arylalkyl group having 6 to 25 carbon atoms.

7. A liquid crystal medium according to any one of claims 1 to 6, comprising one or more compounds selected from the group consisting of formulas II and III. 【Chemistry 15】 (In the formula, R ２ and R ３ This refers to a linear or branched alkyl or alkoxy group that is unsubstituted or halogenated and has 1 to 15 carbon atoms (provided that the group contains one or more CH ２ The group is formed so that the oxygen atoms are not directly bonded to each other. 【Chemistry 16】 -C≡C-, -CF ２ O-, -CH=CH-, -O-, -CO-O- or -O-CO- represent (they can be substituted for each other independently), 【Chemistry 17】 are the same or different [Chemistry 18] This represents, L ２１ , L ２２ , L ３１ and L ３２ These represent H or F, whether identical or different. Y ２ and Y ３ H or CH are the same or different. ３ This represents, X ２ and X ３ This represents a halogen, an alkyl or alkoxy halide having 1 to 3 carbon atoms, or an alkenyl or alkenyloxy halide having 2 or 3 carbon atoms, either identical or different. Z ３ is, -CH ２ CH ２ -, -CF ２ CF ２ -, -COO-, Trans--CH=CH-, Trans-CF=CF-, -CH ２ O- or single bond is represented, l, m, n, and o are each independently 0 or 1.

8. A medium according to any one of claims 1 to 7, comprising one or more compounds of formula IV. 【Chemistry 19】 (In the formula, R ４１ This represents a linear alkyl group having 1 to 12 carbon atoms, a branched or cyclic alkyl group having 3 to 12 carbon atoms, a linear alkenyl group having 2 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, or a cyclic alkenyl group having 5 to 12 carbon atoms, where one or more hydrogen atoms may be replaced by fluorine. R ４２ This represents a linear alkyl or alkoxy group having 1 to 12 carbon atoms, a branched or cyclic alkyl or alkoxy group having 3 to 12 carbon atoms, a linear alkenyl group having 2 to 12 carbon atoms, a branched alkenyl group having 3 to 12 carbon atoms, or a cyclic alkenyl group having 5 to 12 carbon atoms, where one or more hydrogen atoms may be replaced by fluorine.

9. The medium according to any one of claims 1 to 8, comprising one or more compounds selected from the group of compounds of formula IVa and IVb. 【Chemistry 20】 (In the formula, R ４１ and R ４２ These have meanings defined in claim 8, independently of each other, and 【Chemistry 21】 This represents, Z ４ This is a single bond, -CH ２ CH ２ -, -CH=CH-, -CF ２ O-, -OCF ２ -ien-CH ２ O-, -OCH ２ -, -COO-, -OCO-, -C ２ F ４ -, -C ４ H ８ (This represents - or -CF = CF-.)

10. An electronic component comprising a first substrate and a second substrate facing each other, a liquid crystal medium sandwiched between the first and second substrates, and electrodes provided on each substrate or two electrodes provided on only one of the substrates to supply a potential across the liquid crystal medium in order to drive the liquid crystal in a predetermined configuration, The aforementioned liquid crystal medium is characterized in that it includes the liquid crystal medium described in any one of claims 1 to 9.

11. The electronic component according to claim 10, wherein the liquid crystal medium within the component is arranged as an adjustable dielectric configured for use in high-frequency technology.

12. The electronic component according to claim 10 or 11, which is a liquid crystal antenna element, a phase shifter, an adjustable filter, an adjustable metamaterial structure, a matched network, or a varactor.

13. A microwave antenna array characterized by comprising one or more components as described in any one of claims 10 to 12.

14. The component according to claim 10, which is an optical component capable of operating in the visible or infrared region of the electromagnetic spectrum.

15. The component according to claim 14, which is a transmissive spatial light modulator.

16. The component is a reflective spatial light modulator (100) configured to modulate the phase of an incident light signal propagating in at least partially in a first dimension, the first substrate being a transparent glass layer (110) having a first transparent electrode (120), the second substrate being a CMOS silicon back substrate (160), and the component further comprising a mirror (150) positioned between the second substrate and a liquid crystal medium (140), the mirror being positioned and configured as a second electrode (150) and divided into a two-dimensional array of individually addressable pixels, each pixel being individually driven by a voltage signal to provide a local phase change for at least one polarization component of the light signal, according to claim 14.

17. RGB light source, and - A component according to any one of claims 14 to 16, which is arranged and configured to modulate the phase of the incident optical signal from the RGB light source when the optical device is operating. Including optical devices.

18. A method for spatially modulating light, i) Providing an optical component comprising first and second substrates facing each other and each having a surface, wherein the first substrate comprises at least one first electrode and the second substrate comprises at least one second electrode, and the component further comprises a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises a liquid crystal medium as described in any one of claims 1 to 9; ii) A process for providing an RGB light source; ii) A step of receiving incident light from the RGB light source on the surface of the optical component, iii) A step of applying a predetermined voltage to each of the individual electrodes formed on the first substrate in order to modulate the refractive index of the liquid crystal layer. A method that includes this.

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