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CN-121991703-A - Liquid crystal medium and electronic component

CN121991703ACN 121991703 ACN121991703 ACN 121991703ACN-121991703-A

Abstract

The present invention relates to liquid-crystalline media and liquid-crystalline materials comprising a) one or more compounds of the formula I and one or more compounds of the formula T: The radicals and parameters present therein have the meanings defined in claim 1 and relate to electronic components comprising the LC medium, which are operable in the Visible (VIS), infrared (IR) or microwave region of the electromagnetic spectrum. The invention further relates to the use of the LC medium in the IR, VIS or microwave region and to a device comprising the electronic component.

Inventors

  • Qi Tengquan
  • E. Meijer

Assignees

  • 默克专利股份有限公司

Dates

Publication Date
20260508
Application Date
20251107
Priority Date
20241108

Claims (18)

  1. 1. A liquid crystalline medium comprising A) One or more compounds of formula I Wherein the method comprises the steps of R 11 and R 12 are identical or different and represent H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 groups can be replaced by 、 、 、 Or (b) Instead, and wherein one or more H atoms may be replaced by fluorine, L 11 、L 12 、L 13 identically or differently represents H, CH 3 , cl or F, A 11 represents phenylene-1, 4-diyl, in which 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 , or cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, in each of which one or two non-adjacent CH 2 groups may be 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, in which one or more H atoms may be replaced by F, A 12 represents phenylene-1, 4-diyl, in which 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 , or cyclohexane-1, 4-diyl or cyclohexene-1, 4-diyl, in each of which one or two non-adjacent CH 2 groups may be replaced by O and/or S and one or more H atoms may be replaced by F, Z 1 represents a single bond 、-CH 2 CH 2 -、-CH=CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -、-CF=CF- or-ch=chch 2 O-, N is 0 or 1; And B) One or more compounds of the formula T, Wherein the method comprises the steps of R T1 and R T2 , identical or different, represent halogen, CN, NCS, straight-chain alkyl or alkoxy having 1 to 15C atoms, straight-chain alkenyl or alkenyloxy having 2 to 15C atoms or branched-chain alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 15C atoms, where one or more CH 2 groups in these radicals may be such that O atoms are not directly bonded to one another and are each independently of one another , , , , -C.ident.C-, -CF 2 O-,-OCF 2 -, -CH=CH-, -O-, -CO-O-or-O-CO-, and wherein one or more H atoms can be replaced by halogen, R T3 represents F, CN, straight-chain alkyl or alkoxy having 1 to 5C atoms, straight-chain alkenyl or alkenyloxy having 2 to 5C atoms or branched-chain alkyl, alkoxy, alkenyl or alkenyloxy having 3 to 5C atoms, where the CH 2 groups in these groups may be replaced by , , Or (b) Instead, and wherein one or more H atoms may be replaced by halogen, A 0 ,A 1 , and A 2 , each independently of the others, represent phenylene-1, 4-diyl, in which 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, in which one or two non-adjacent CH 2 groups may be replaced independently of each other 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 each independently of the other represent -CF 2 O-,-OCF 2 -,-CH 2 O-,-OCH 2 - ,-CO-O-,-O-CO-,-C 2 H 4 -,-C 2 F 4 ,-CF 2 CH 2 -,-CH 2 CF 2 -,-CFHCFH-,-CFHCH 2 -,-CH 2 CFH-,-CF 2 CFH-,-CFHCF 2 -,-CH=CH-,-CF=CH-,-CH=CF-,-CF=CF-,-C≡C- or a single bond; n represents 0,1,2 or 3, and M represents 0,1,2 or 3.
  2. 2. The liquid-crystalline medium according to claim 1, wherein the medium comprises one or more compounds selected from the group consisting of compounds of the formulae S1, S2 and S3 Wherein the method comprises the steps of R S1 and R S2 , which are identical or different on each occurrence, represent H or a straight-chain alkyl radical having from 1 to 25 carbon atoms or a branched alkyl radical having from 3 to 25 carbon atoms, which is unsubstituted or monosubstituted by CN or CF 3 or at least monosubstituted by halogen, and wherein one or more CH 2 groups are each independently of one another in such a way that O and/or S atoms are not directly bonded to one another 、 、 、 、 -O-, -S-, -CO-O-, -O-CO-O-, -CH=CH-, or-C≡C-, or halogen, aryl, heteroaryl, alkylaryl or arylalkyl having 6, 5, 7 or 7 to 25 carbon atoms respectively, each of which is unsubstituted or monosubstituted or polysubstituted by alkyl or halogen having 1 to 6C atoms, S is 0, 1 or 2, T is 0,1, 2 or 3, Q is 1, 2, 3 or 4, G represents a hydrocarbon radical having from 1 to 60 carbon atoms, which may be linear or branched or cyclic, and which is unsubstituted or monosubstituted by CN or CF 3 or at least monosubstituted by halogen, and wherein one or more CH 2 groups are each, independently of one another, represented by-O-, such that O or S atoms are not directly bonded to one another-S-, -NR 0 -, -CO-O-, -O-CO-O-, -CH=CH-, or-C≡C-, substituted, R 0 represents H or an alkyl group having 1 to 6C atoms, R 2 represents H, -O, -OH, a linear alkyl or alkoxy group having 1 to 12C atoms or a branched or cyclic alkyl group having 3 to 25C atoms or an arylalkoxy group having 7 to 25C atoms, R 21 and R 22 are identical or different and represent a straight-chain alkyl radical having 1 to 12 carbon atoms or a branched alkyl radical having 3 to 12 carbon atoms, or R 21 and R 22 together with the carbon atoms to which they are attached form a cycloalkyl radical having 5 to 12 carbon atoms, R 23 and R 24 are identical or different and represent a straight-chain alkyl radical having 1 to 12 carbon atoms or a branched alkyl radical having 3 to 12 carbon atoms, or R 23 and R 24 together with the carbon atoms to which they are attached form a cycloalkyl radical having 5 to 12 carbon atoms, Z 2 , identically or differently at each occurrence, represents-O-; -C (O) O-, -OC (O) -or a single bond, R ST represents H, alkyl or alkoxy having 1 to 12C atoms or alkenyl, alkenyloxy or alkoxyalkyl having 2 to 12C atoms, where one or more CH 2 -groups may be reacted 、 、 、 Or (b) Instead, and wherein one or more H atoms may be replaced by fluorine, Z ST each independently of the other represents -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, Which on each occurrence, are identical or different and represent cyclohexane-1, 4-diyl, cyclohexene-1, 4-diyl, pyran-2, 5-diyl or 1, 3-dioxane-2-5-diyl, wherein one or more H atoms may be replaced by F, P is 0, 1 or 2.
  3. 3. The liquid-crystalline medium according to claim 1 or 2, wherein the medium comprises one or more compounds selected from the group consisting of compounds of the formulae S2-1 and S2-2 Wherein G represents a divalent aliphatic group having 1 to 20C atoms or a cycloaliphatic group having 3 to 20C atoms.
  4. 4. A liquid-crystalline medium according to one or more of claims 1 to 3, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae I-1 to I-3 Wherein R 11 、R 12 、Z 1 、L 11 、L 12 and L 13 have the meanings given in claim 1.
  5. 5. Liquid-crystalline medium according to one or more of claims 1 to 4, wherein the medium comprises one or more compounds of the formulae T-1 to T-6 Wherein R T1 ,R T2 and R T3 have the meanings indicated in claim 1, L represents halogen, CN, CH 3 ,CHF 2 ,CH 2 F,CF 3 ,OCH 3 ,OCHF 2 or OCF 3 , and R, s and t are independently 0,1,2,3, or 4.
  6. 6. Liquid-crystalline medium according to one or more of claims 1 to 5, wherein the medium comprises one or more compounds of formula S1-1 Wherein the method comprises the steps of R S1 represents H, F or Cl, and R 21 and R 22 are identical or different and represent H or a straight-chain or branched alkyl radical having 1 to 12 carbon atoms, where one or more CH 2 groups are each, independently of one another, such that O atoms are not directly bonded to one another 、 、 、 、 -O-, -CO-O-, -O-CO-, -ch=ch-, or-c≡c-, or aryl or aralkyl having 6 to 25 carbon atoms.
  7. 7. Liquid-crystalline medium according to one or more of claims 1 to 6, wherein the medium comprises one or more compounds selected from the group of compounds of formulae II and III: Wherein the method comprises the steps of R 2 and R 3 represent unsubstituted or halogenated, straight-chain or branched alkyl or alkoxy having 1 to 15C atoms, where one or more CH 2 groups of these groups can be such that O atoms are not directly bonded to one another and are each independently of one another 、 、 、 、 -C≡C-, -CF 2 O-, -CH=CH-, -O-, -CO-O-or-O-CO-substitution, To the point of And To the point of The same or different expressions 、 、 、 、 、 、 、 、 、 、 、 、 、 Or (b) , L 21 、L 22 、L 31 and L 32 are identical or different and represent H or F, Y 2 and Y 3 are identical or different and represent H or CH 3 , X 2 and X 3 , which are identical or different, represent halogen, halogenated alkyl or alkoxy having 1 to 3C atoms or halogenated alkenyl or alkenyloxy having 2 or 3C atoms, Z 3 represents-CH 2 CH 2 -、-CF 2 CF 2 -, -COO-, trans-CH=CH-, trans-cf=cf-, -CH 2 O-, or a single bond, L, m, n and o are each independently 0 or 1.
  8. 8. The medium according to one or more of claims 1 to 7, wherein the medium comprises one or more compounds of formula IV Wherein the method comprises the steps of R 41 represents a linear alkyl group having 1 to 12C atoms or a branched or cyclic alkyl group having 3 to 12C atoms, or a linear alkenyl group having 2 to 12C atoms or a branched alkenyl group having 3 to 12C atoms or a cyclic alkenyl group having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine, R 42 represents a linear alkyl or alkoxy group having 1 to 12C atoms or a branched or cyclic alkyl or alkoxy group having 3 to 12C atoms, or a linear alkenyl group having 2 to 12C atoms or a branched alkenyl group having 3 to 12C atoms or a cyclic alkenyl group having 5 to 12C atoms, wherein one or more H atoms are optionally replaced by fluorine.
  9. 9. The medium according to one or more of claims 1 to 8, wherein the medium comprises one or more compounds selected from the group consisting of compounds of formulae IVa and IVb Wherein the method comprises the steps of R 41 and R 42 independently of one another have the meanings defined in claim 8, and Representation of 、 、 、 Or (b) , Z 4 represents a single bond 、-CH 2 CH 2 -、-CH=CH-、-CF 2 O-、-OCF 2 -、-CH 2 O-、-OCH 2 -、-COO-、-OCO-、-C 2 F 4 -、-C 4 H 8 - or-CF=CF-.
  10. 10. Electronic assembly comprising a first and a second substrate facing each other, a liquid crystal medium sandwiched between the first and the second substrate, electrodes provided on each substrate or two electrodes provided on only one of the substrates for providing an electric potential across the liquid crystal medium for driving a liquid crystal of a predetermined configuration, characterized in that the liquid crystal medium comprises a liquid crystal medium according to one or more of claims 1 to 9.
  11. 11. The electronic component of claim 10, wherein the liquid crystal medium in the component is arranged as a tunable dielectric configured for use in high frequency technology.
  12. 12. The electronic component of claim 10 or 11, wherein the component is a liquid crystal based antenna component, a phase shifter, a tunable filter, a tunable metamaterial structure, a matching network, or a varactor.
  13. 13. Microwave antenna array, characterized in that it comprises one or more components according to one or more of claims 10 to 12.
  14. 14. The assembly of claim 10, wherein the assembly is an optical assembly operable in the visible or infrared range of the electromagnetic spectrum.
  15. 15. The component of claim 14, wherein the component is a transmissive spatial light modulator.
  16. 16. The component of claim 14, wherein the component is a reflective spatial light modulator (100) configured to modulate a phase of an incident optical signal propagating at least partially in a first dimension, wherein the first substrate is a transparent glass layer (110) having a first transparent electrode (120), and wherein the second substrate is a CMOS silicon backplane (160), the component further comprising a mirror (150) disposed between the second substrate and a liquid crystal medium (140), wherein the mirror is divided into a two-dimensional array of individually addressable pixels arranged and configured as a second electrode (150), each pixel being individually drivable by a voltage signal to provide a local phase change to at least one polarization component of the optical signal.
  17. 17. An optical device, comprising: RGB light source, and The component of one or more of claims 14 to 16 arranged and configured to modulate a phase of an incident optical signal from the RGB light sources when operating an optical device.
  18. 18. A method of spatially modulating light, the method comprising, I) Providing an optical assembly comprising a first and a second substrate facing each other and each having a surface, the first substrate comprising at least one first electrode and the second substrate comprising at least one second electrode, the assembly further comprising a liquid crystal layer sandwiched between the first and second substrates, wherein the liquid crystal comprises a liquid crystal medium according to one or more of claims 1 to 9; ii) providing an RGB light source; ii) receiving incident light from the RGB light sources at a surface of the optical assembly; iii) A predetermined voltage is applied to each of the individual electrodes formed on the first substrate so as to modulate the refractive index of the liquid crystal layer.

Description

Liquid crystal medium and electronic component Technical Field The present invention relates to Liquid Crystal (LC) media and electronic components comprising such LC media, which are operable in the Visible (VIS), infrared (IR) or microwave regions of the electromagnetic spectrum. The invention further relates to the use of the LC medium in the IR, VIS or microwave region and to a device comprising the electronic component. Background Liquid crystal media have been used for many years in electro-optic displays (liquid crystal displays: LCDs) to display information by amplitude modulation of polarized light in the visible region, and are widely used in TVs, monitors or displays of portable devices such as tablet PCs, mobile phones, and the like. Nematic liquid crystals have also been proposed for phase modulation of light-article 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 describes a liquid crystal based optical phased array for various types of sensor applications-article Scott R. Davis, George Farca, Scott D. Rommel, Seth Johnson, Michael H. Anderson, "Liquid crystal waveguides： new devices enabled by ＞1000 waves of optical phase control," Proc.. SPIE 7618, Emerging Liquid Crystal Technologies V, 76180E (2010, month 2 and 12-day-and doi-10.1117/12.851788 describes refractive beam steering using a waveguide structure. Liquid crystal on silicon (LCoS) is a miniaturized reflective active matrix liquid crystal display or "microdisplay" that uses a liquid crystal layer on a silicon backplane. Which is also referred to as a Spatial Light Modulator (SLM). The silicon back plane is an array of pixels each having a mirrored surface that can simultaneously act as an electrical conductor. Each pixel comprises a fixed mirror covered by an active liquid crystal layer having a twisted nematic alignment which can be switched to a homeotropic alignment by applying a voltage. LCoS microdisplays are small, typically less than 1.0 inch diagonal, but can achieve high resolutions ranging from 1/4 VGA (7.8 ten thousand pixels) to uxga+ (over 200 ten thousand pixels). LCoS displays also have very small cell thicknesses, typically about 1 micron, due to the small pixel size. When the device is operated in reflective mode, a low cell thickness is also required for light to travel twice through the LC layer. Thus, the liquid crystal phase used for these displays must have a high optical anisotropy Δn in particular, in contrast to the low Δn LC phase typically required for conventional reflective LC displays. The use of a small box thickness is preferred, especially for applications requiring a short response time, since the response time is proportional to the box thickness, typically decreasing twice. Liquid crystal compounds with high birefringence often have an intrinsic smectic phase or induce the formation of smectic phases when mixed with other liquid crystal compounds, which has an adverse effect on the low temperature stability of the display. LCoS was originally developed for projection televisions, but is also used today for wavelength selective switching, structured illumination, near-eye displays, and optical pulse shaping. The computer-generated hologram may be encoded on a spatial light modulator arranged to modulate the amplitude and/or phase of incident light forming part of a holographic projector as described in WO2020/015933 A1. Such projectors have been applied in heads-up displays (HUDs) and head-mounted displays (HMDs) that include near-eye devices. Another application using liquid crystal based devices is light detection and ranging (lidar) -a method for measuring distance by illuminating a target with laser light and measuring reflection with a sensor. The difference in laser return time and wavelength can then be used to form a digital 3-D representation of the target. In WO2019/24052 A1, a holographic LIDAR system using e.g. an LCoS SLM is proposed. One of the most important characteristics of a phase-only LCoS device is its use of an optically nonlinear liquid crystal material that is sensitive to operating temperature. While LCoS devices have in the past focused primarily on optical intensity modulation that is rarely affected by temperature changes, for phase-only LCoS devices the optical phase modulation of the incident light is a necessary performance parameter and it may be susceptible to small changes in operating temperature, causing significant changes in the output of the corresponding optical diffraction. Another key challenge in developing next generation LCoS devices is the formation of high-speed multi-level phase modulation. Nematic LCoS devices have demonstrated the benefits of multi-level phase modulation, but are limited by the slow response time of nematic LCs. This is especially true in telecommunications applications where