Liquid crystal compounds and compositions for adjustable lenses - Patents.com

Abstract

To provide compounds and compositions that can be used as liquid crystal materials in adjustable ophthalmic lenses.SOLUTION: The present invention provides a compound having a structure of formula (I). (R1 is H, C1-C10 alkyl, halogen or the like; R2 and R3 independently represent H, halogen or the like; R4 is formula (II) or formula (III); m and n each denote an integer of 1-5; R5 and R6 are saturated C1-C10 alkyl or saturated C1-C10 alkoxy).SELECTED DRAWING: Figure 1

Description

[Technical field]

[0001] The present disclosure relates generally to liquid crystal materials having compounds and compositions that can be used in tunable lenses.

[0002] (CROSS REFERENCE TO RELATED APPLICATIONS) This patent application claims the benefit of U.S. Provisional Patent Application No. 63 / 293,528, entitled "LIQUID CRYSTAL COMPOUNDS AND COMPOSITIONS FOR TUNABLE LENSES," filed on December 23, 2021, and is incorporated by reference herein in its entirety. [Background technology]

[0003] Ophthalmic lenses are ophthalmic devices that modify or change the vision of the human eye. An accommodative ophthalmic lens can be adjusted to change the visual characteristics of light passing through the lens. An adjustable lens can include one or more liquid crystal cells. Each liquid crystal cell can include a layer of liquid crystal material sandwiched between transparent substrates. A control circuit can apply control signals to an array of electrodes in the liquid crystal cells to adjust the phase profile of the liquid crystal material. In various configurations, the adjustable lens can include multiple liquid crystal cells (e.g., three or six liquid crystal cells). The electrodes in the liquid crystal cells can be oriented along three different directions. Summary of the Invention

[0004] Additional embodiments and features are set forth in part in the description that follows, and in part will become apparent to those skilled in the art upon examination of the specification or may be learned by practice of the embodiments described herein. A further understanding of the nature and advantages of certain embodiments may be realized by reference to the remaining portions of the specification and the drawings that form a part of this disclosure.

[0005] In a first aspect, the disclosure relates to a compound having the structure of formula (I): [ka] During the ceremony, R1 is hydrogen, saturated C 1~10 selected from alkyl, halogen, and pseudohalogen; R2 and R3 are each independently selected from hydrogen, halogen, and pseudohalogen; R4 is represented by formula (II) and formula (III): [ka] is selected from In the formula, m is an integer of 1 to 5, R5 is saturated C1~C 10 Alkyl or saturated C1-C 10 is an alkoxy; n is an integer from 1 to 5, R6 is saturated C1~C 10 Alkyl or saturated C1-C 10 It is an alkoxy.

[0006] In a second aspect, the disclosure relates to a composition comprising a plurality of compounds.

[0007] In a third aspect, the disclosure provides a first compound having a structure of formula (IV): [ka] A second compound having the structure of formula (V): [ka] and A third compound having the structure of formula (VI): [ka] In the formula: R1 is the saturated C 1~10 selected from alkyl, halogen, and pseudohalogen; R2 and R3 are each independently selected from hydrogen, halogen, and pseudohalogen; R7 is saturated C1~C 10Alkyl or saturated C1-C 10 is an alkoxy; R8 is saturated C1~C 10 Alkyl or saturated C1-C 10 is an alkoxy; R9 is saturated C1~C 10 It is an alkyl.

[0008] In a fourth aspect, the present disclosure relates to a liquid crystal cell comprising a first substrate transparent in the visible spectrum and a second substrate transparent in the visible spectrum, the first substrate and the second substrate sandwiching a liquid crystal layer, the liquid crystal layer comprising a compound or composition as described herein. [Brief description of the drawings]

[0009] [Figure 1] 1 is a side view of an exemplary liquid crystal cell that can be used to form an adjustable lens, according to an exemplary embodiment. [Diagram 2] 2 is a side view of an exemplary liquid crystal module having first and second liquid crystal layers with anti-parallel liquid crystal alignment orientations according to an exemplary embodiment. FIG. [Diagram 3] 2 is a side view of light entering a liquid crystal module according to an exemplary embodiment. [Figure 4] FIG. 1 is an exploded perspective view of an exemplary adjustable lens having first, second, and third liquid crystal cells, each with an associated orientation of electrodes, according to an exemplary embodiment. [Diagram 5] 1 is an exploded perspective view of an exemplary adjustable lens having first, second, and third liquid crystal modules, each with an associated orientation of electrodes, according to an exemplary embodiment. [Figure 6] 1 illustrates the band gap of polarizability change for several exemplary compounds, according to an exemplary embodiment. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present disclosure can be understood by reference to the following detailed description in conjunction with the drawings described below: For clarity of illustration, certain elements in the different drawings may not be drawn to scale and may be represented diagrammatically or conceptually, or may not precisely correspond to certain physical configurations of the embodiments.

[0011] The present disclosure relates to compounds and compositions that can be used as liquid crystal materials in ophthalmic lenses. In some variations, the compounds can be used as liquid crystal materials or can be combined into compositions that are used as liquid crystal materials. The compounds have a rigid core that includes one or more phenyl groups linked by single bonds or π-electron-containing bridging groups, a polar group linked to the terminal phenyl substituent of the rigid core, a non-polar terminal group opposite the rigid phenyl core, and optionally one or more lateral substituents. The compositions are combinations of different individual compounds.

[0012] (definition) "Alkyl" by itself or as part of another substituent refers to a saturated or unsaturated branched, straight chain, or cycloalkyl group derived by removing one hydrogen atom from a single carbon atom of a parent alkane. Typical alkyl groups include, but are not limited to, methyl, ethyl, propyl (e.g., propan-1-yl, propan-2-yl (isopropyl), cyclopropan-1-yl, etc.), butyl (e.g., butan-1-yl, butan-2-yl (sec-butyl), 2-methyl-propan-1-yl (isobutyl), 2-methyl-propan-2-yl (tert-butyl), cyclobutan-1-yl, etc.), and the like. Typical cycloalkyl groups include cyclopentyl, cyclohexyl, cycloheptyl, cyclononyl, cyclodecyl, and the like.

[0013] "Alkoxy" refers to the radical -OR where R represents an alkyl group as defined herein. Representative examples include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, cyclohexyloxy, and the like.

[0014] The "compounds" disclosed herein include any specific compounds within the scope of the formula. Compounds can be identified by either their chemical structure and / or chemical name. Compounds described herein can contain one or more chiral centers and / or double bonds and can therefore exist as stereoisomers, such as double bond isomers (i.e., geometric isomers), enantiomers, or diastereomers. Thus, any chemical structure within the scope of the present specification depicted in its relative configuration, in whole or in part, encompasses all possible enantiomers and stereoisomers of the exemplified compound, including stereoisomerically pure forms (e.g., geometrically pure, enantiomerically pure, or diastereomerically pure) as well as enantiomeric and stereoisomeric mixtures. Enantiomeric and stereoisomeric mixtures can be resolved into their component enantiomers or stereoisomers using separation techniques or chiral synthesis techniques well known to those skilled in the art. Compounds include, for example, optical isomers of the compound, its racemates, and other mixtures. In such embodiments, the single enantiomers or diastereomers, i.e., optically active forms, can be obtained by asymmetric synthesis or by resolution of the racemates, which can be accomplished, for example, by methods such as crystallization in the presence of a resolving agent, or chromatography using, for example, a chiral stationary phase.

[0015] Compounds also include isotopically labeled compounds where one or more atoms have an atomic mass different from the atomic mass conventionally found in nature. Examples of isotopes that can be incorporated into the compounds disclosed herein include, for example, 2 H, 3 H, 11 C. 13 C. 14 C. 15 N, 18 O. 17 O. 33 S, 34S and the like. Compounds can exist in unsolvated forms as well as solvated forms, including hydrated forms, and as N-oxides. In general, compounds disclosed herein can be free acids, hydrates, solvates, or N-oxides. Compounds include their salts, solvates of any of the above free acid forms. A solvate refers to a molecular complex of a compound with one or more solvent molecules in stoichiometric or non-stoichiometric amounts. When a substructure of a compound is shown, an asterisk (*) indicates the attachment point of the substructure to the rest of the molecule.

[0016] "Halogen" refers to a fluoro, chloro, bromo, or iodo group.

[0017] "Pseudohalogen" refers to a polyatomic anion that can replace a halogen. Non-limiting examples of pseudohalogens include, but are not limited to, cyanide, cyanate, thiocyanate, and azide.

[0018] Further non-limiting aspects of the present disclosure will now be described with reference to the drawings and description, in which: Figures 1 to 6 are merely illustrative and provide non-limiting examples of variations of the present disclosure.

[0019] (Ophthalmic lenses) The present disclosure relates to ophthalmic lenses having liquid crystal compounds or compositions contained herein.

[0020] A side cross-sectional view of an exemplary ophthalmic lens is shown in FIG. 1. Component 22 can include a liquid crystal cell 40. Liquid crystal cell 40 can have a liquid crystal layer 34 that includes a compound or composition of the present disclosure. Liquid crystal layer 34 can be interposed between substrates that are transparent in the visible spectrum (400 nm to 750 nm), such as upper substrate 32 and lower substrate 30. Substrates 32 and 30 can be formed of transparent materials, such as transparent glass, sapphire, or other transparent crystalline materials, cellulose triacetate, transparent plastic, cyclic olefin polymer (COP), cyclic olefin copolymer (COC), or other transparent layers. Component 22 can have a pattern of electrodes that can be supplied with a signal from control circuit 26 to generate a desired voltage on component 22. In the example of FIG. 1, these electrodes include elongated electrodes (e.g., strip-shaped electrodes), such as electrode 38 on substrate 30 that extend along the X dimension, and a common electrode (e.g., a blanket layer of conductive material on substrate 32), such as common electrode 36 on substrate 32. Electrodes 36 and 38 may be formed from a transparent conductive material such as indium tin oxide, a conductive polymer such as poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT:PPS), or other transparent electrode structures and may be disposed on the exterior and / or interior surfaces of substrates 32 and 30.

[0021] At each location of the electrode strips 38 in the component 22, a voltage can be applied across the liquid crystal layer 34 by supplying a first voltage to the electrode 38 and a second voltage (e.g., ground) to the common electrode 36. The liquid crystal between the two electrodes experiences an applied electric field whose magnitude is proportional to the difference between the first and second voltages on the electrodes. By controlling the voltages on the electrodes 38 and the common electrode 36, the refractive index of the liquid crystal layer 34 of the component 22 can be dynamically adjusted to produce a customized lens.

[0022] 1, strip electrodes 38 (sometimes called finger electrodes) extend parallel to the X-axis, allowing the refractive index profile (sometimes called phase profile) of liquid crystal cell 40 to be modulated in the Y-dimension by applying a desired voltage to each finger electrode 38.

[0023] When an electric field is applied to the liquid crystals in layer 34, the liquid crystals change orientation. The speed at which a given liquid crystal material can be reoriented is limited by factors such as the thickness of layer 34 (e.g., thickness T1 in FIG. 1, sometimes referred to as the cell gap), or the viscosity and / or elasticity of the liquid crystal compound or composition.

[0024] The lens element 22 may include two or more liquid crystal cells 40 stacked on top of one another. This type of arrangement is shown in FIG.

[0025] As shown in FIG. 2, the ophthalmic lens component 22 can include a liquid crystal module 44. The liquid crystal module 44 can include two or more liquid crystal cells 40. Each liquid crystal cell can include a liquid crystal layer 34 including a compound or composition of the present disclosure sandwiched between an upper substrate 32 and a lower substrate 30. In some variations, at least one of the liquid crystal layers includes a compound or composition described herein. The different liquid crystal layers can have the same or different compounds or compositions. Finger electrodes 38 can be formed on each lower substrate 30 and can extend parallel to the X-axis. A common electrode 36 can be formed on each upper substrate 32. If desired, the common voltage electrode 36 can be formed on the lower substrate 30 and the finger electrodes 38 can be formed on the upper substrate 32.

[0026] The cell gap of each liquid crystal cell 40 in the module 44 can be smaller than the cell gap of the liquid crystal cell 40 of Figure 1. For example, the liquid crystal layers 34 of the modules 44 of Figure 2 can each have a thickness T2 that is smaller than the thickness T1 of the liquid crystal layer 34 of the cells 40 of Figure 1. The reduced cell gap can improve the tuning speed of the liquid crystal layers 34 while still maintaining a satisfactory tuning range.

[0027] At each location of the finger electrodes 38 in the component 22, a voltage can be applied across each liquid crystal layer 34 by supplying a first voltage to the finger electrodes 38 and a second voltage (e.g., ground voltage) to the common electrode 36. The liquid crystal between the two electrodes experiences an applied electric field whose magnitude is proportional to the difference between the first and second voltages on the electrodes. By controlling the voltages on the electrodes 38 and the common electrode 36, the refractive index of each liquid crystal layer 34 of the component 22 can be dynamically adjusted to produce a customized lens. Because the finger electrodes 38 extend along the X dimension, the phase profile of each liquid crystal cell 40 can be modulated in the Y dimension by applying a desired voltage to each finger electrode 38.

[0028] The overlapping portions of the two liquid crystal layers 34 in the module 44 can be controlled using the same or different voltages to achieve a desired refractive index in that portion of the module 44. For example, the finger electrode 38A of the upper liquid crystal cell 40 in the module 44 can overlap the finger electrode 38B of the lower liquid crystal cell 40 in the module 44. A first voltage V1 can be applied across the portion of the upper liquid crystal layer 34 that overlaps the finger electrode 38A, and a second voltage V2 can be applied across the portion of the lower liquid crystal layer 34 that overlaps the finger electrode 38B. The voltages V1 and V2 can be different or the same. The control circuit 26 can determine the ratio of V1 to V2 based on the desired refractive index in that portion of the liquid crystal module 44.

[0029] 3 shows an example cross-sectional side view of light 302 entering a liquid crystal module 304. Liquid crystal molecules 306 within the liquid crystal module 304 can be adjusted such that the light can be focused with an adjustable focal length 308 after passing through a lens.

[0030] 4 and 5 show exploded perspective views of an exemplary lens component 22 having three orientations of the electrodes. In the example of FIG. 4, the adjustable lens component 22 includes three liquid crystal cells 40. Each liquid crystal cell 40 can have a structure of the type described in connection with FIG. 1, with finger electrodes 38-1, 38-2, and 38-3 oriented along three different directions. For example, finger electrode 38-1 can be oriented at 0 degrees relative to the X-axis, finger electrode 38-2 can be oriented at 120 degrees relative to the X-axis, and finger electrode 38-3 can be oriented at 60 degrees relative to the X-axis. However, this is merely exemplary. In general, electrodes 38-1, 38-2, and 38-3 can have any suitable orientation.

[0031] In FIG. 5, the adjustable lens component 22 includes three liquid crystal modules 14. Each liquid crystal module 14 can have a structure of the type described in connection with FIG. 2. In particular, each liquid crystal module 14 can include an upper liquid crystal cell 40 and a lower liquid crystal cell 40. The liquid crystal layers of the upper and lower liquid crystal cells 40 can have anti-parallel liquid crystal alignment orientations, if desired. As shown in FIG. 5, the finger electrodes 38-1, 38-2, and 38-3 of the liquid crystal module 14 are oriented along three different directions. For example, the finger electrode 38-1 can be oriented at 0 degrees relative to the X-axis, the finger electrode 38-2 can be oriented at 120 degrees relative to the X-axis, and the finger electrode 38-3 can be oriented at 60 degrees relative to the X-axis. However, this is merely exemplary. In general, the electrodes 38-1, 38-2, and 38-3 can have any suitable orientation.

[0032] In various aspects, the compounds and compositions of the present disclosure can be used in liquid crystal lenses as described in U.S. Pat. No. 11,086,143, which is incorporated herein by reference in its entirety.

[0033] The present disclosure relates to devices that include tunable liquid crystal lenses. In various aspects, the liquid crystals can be designed to have properties including, but not limited to, lower viscosity, higher elastic constant (K33), and more polarizable compounds. Liquid crystal lenses that use the compounds and compositions as liquid crystal materials thereby provide improved tunable lenses in the visible spectrum (400 nm to 750 nm). The lenses can be used, for example, in auto reading glasses and AR / VR glasses.

[0034] (compound) The liquid crystal cells described herein include a liquid crystal layer that includes a compound or composition of the present disclosure.

[0035] In one variation, the compound has the structure of formula (I): [ka] During the ceremony, R1 is hydrogen, saturated C 1~10 selected from alkyl, halogen, and pseudohalogen; R2 and R3 are each independently selected from hydrogen, halogen, and pseudohalogen; R4 is selected from the structures of formula (II) or formula (III), [ka] m is an integer from 1 to 5; R5 is saturated C1~C 10 Alkyl or saturated C1-C 10 is an alkoxy; n is an integer from 1 to 5, R6 is saturated C1~C 10 Alkyl or saturated C1-C 10 It is an alkoxy.

[0036] Substituents can be selected from a range of possible options.

[0037] In some variations, R1 is hydrogen. In some variations, R1 is a saturated C 1~10In some variations, R is a saturated C 1~5 In some variations, R is a saturated C 1~2 In some variations, R1 is an alkyl. In some variations, R1 is ethyl. In some variations, R1 is methyl. In some variations, R1 is a halogen. In some variations, R1 is a pseudohalogen. In some further variations, R1 is a cyano substituent. In some further variations, R1 is a thioisocyanate substituent.

[0038] In some variations, R2 and R3 are each independently selected from hydrogen or halogen. In some variations, R2 and R3 are both hydrogen. In some variations, R2 and R3 are both halogen. In some variations, the halogen is fluorine. In some variations, R2 and R3 are both fluorine. In some variations, R2 is hydrogen and R3 is halogen.

[0039] When R4 is formula (II), in some variations, m is 1. In some variations, m is 2. In some variations, m is 3. In some variations, m is 4. In some variations, m is 5. Further, when R4 is formula (II), R5 is a saturated alkyl. In some variations, R5 is a saturated linear C1-C 10 In some variations, R5 is an alkyl. In some variations, R5 is a saturated linear C1-C5 alkyl. In some variations, R5 is n-butyl. In some variations, R5 is n-propyl. In some variations, R5 is ethyl. In some variations, R5 is methyl. In some variations, R5 is a C5-C 10 In some variations, R5 is a saturated C5-C 10 In some variations, R5 is cycloalkyl. In some variations, R5 is cyclohexyl. In some variations, R5 is a saturated C1-C 10 In some variations, R5 is a saturated C1-C5 alkoxy.

[0040] When R4 is formula (III), in some variations, n is 1. In some variations, n is 2. In some variations, n is 3. In some variations, n is 4. In some variations, n is 5. Further, when R4 is formula (III), R6 is a saturated alkyl. In some variations, R6 is a saturated linear C1-C 10 In some variations, R6 is an alkyl. In some variations, R6 is a saturated linear C1-C5 alkyl. In some variations, R6 is n-butyl. In some variations, R6 is n-propyl. In some variations, R6 is ethyl. In some variations, R5 is methyl. In some variations, R6 is a C5-C 10 In some variations, R6 is a saturated C5-C 10 In some variations, R6 is a cycloalkyl. In some variations, R6 is a cyclohexyl. In some variations, R6 is a saturated C1-C 10 In some variations, R6 is a saturated C1-C5 alkoxy. In various embodiments, R4 can be combined in any combination with any structure or variable herein.

[0041] In some variations, the compound has the structure of formula (IV): [ka] where R1, R2, and R3 can be as described herein in any combination, and R7 is saturated alkyl. In some variations, R7 is saturated linear C1-C 10 In some variations, R7 is an alkyl. In some variations, R7 is a saturated linear C1-C5 alkyl. In some variations, R7 is n-butyl. In some variations, R7 is n-propyl. In some variations, R7 is ethyl. In some variations, R7 is methyl. In some variations, R7 is a saturated C5-C alkyl. 10 In some variations, R7 is cycloalkyl. In some variations, R7 is cyclohexyl. In some variations, R7 is a saturated linear C1-C 10 In some variations, R7 is -OC2H5-OC4H9 or -OC5H 11 It is.

[0042] In some variations, the compound has the structure of formula (V): [ka] where R1, R2, and R3 can be as described herein in any combination, and R8 is saturated alkyl. In some variations, R8 is saturated linear C1-C 10 In some variations, R8 is an alkyl. In some variations, R8 is a saturated linear C1-C5 alkyl. In some variations, R8 is n-butyl. In some variations, R8 is n-propyl. In some variations, R8 is ethyl. In some variations, R8 is methyl. In some variations, R8 is a saturated C5-C alkyl. 10 In some variations, R8 is cycloalkyl. In some variations, R8 is cyclohexyl. In some variations, R8 is a saturated linear C1-C 10 In some variations, R8 is -OC2H5-OC4H9 or -OC5H 11 It is.

[0043] In some variations, the compound has the structure of formula (IV): [ka] where R1, R2, and R3 can be as described herein in any combination, and R9 is saturated alkyl. In some variations, R9 is saturated linear C1-C 10 In some variations, R9 is an alkyl. In some variations, R9 is a saturated linear C1-C5 alkyl. In some variations, R9 is n-butyl. In some variations, R9 is n-propyl. In some variations, R9 is ethyl. In some variations, R9 is methyl. In some variations, R9 is a saturated C5-C alkyl. 10 In some variations, R9 is cyclohexyl.

[0044] (Intramolecular properties) The compounds of the present disclosure have properties that improve their use in liquid crystals.

[0045] (Rigid Core and Cross-Linking Groups) A rigid core containing phenyl substituents and optional pi-bond bridges can provide higher polarizability. Multiple pi-bonds can be connected in series to provide delocalized electrons over longer intramolecular distances. More phenyl substituents and pi-containing bridges can increase the polarizability of the compound. The delocalized electrons can thereby provide a superlinear increase in the polarizability of the compound.

[0046] The difference in refractive index along the long and transverse axes of the compound corresponds to a difference in polarizability. Increasing the polarizability increases the tunability of the liquid crystal.

[0047] FIG. 6 shows the band gap of the polarizability of some exemplary compounds. Absorption in the visible spectrum occurs at band gaps below 3.1 eV. Increasing the number of phenyl rings in the described compounds results in smaller band gaps. For example, in compounds of formula (I), increasing the variables "m" and "n" increases the polarizability but remains above the 3.1 eV threshold so that a liquid crystal layer containing the compound or composition remains transparent. If the π-bond bridge becomes too long, the compound may absorb radiation in the visible spectrum, and the liquid crystal may then lose transparency in the visible spectrum. As the length of the compound increases, it may become less transparent. By limiting the net size while increasing the polarizability, the compounds and compositions are transparent over the entire visible range.

[0048] Macroscopic changes in the refractive index can be achieved by rotation of the molecules. Thus, the relative major axis to the transverse axis corresponds to the polarization of light incident on the liquid crystal. This property can be measured as Δn for wavelengths in the visible spectrum, determined by the difference in polarizability along the major versus transverse axes.

[0049] (polar group) A polar group may be at the terminus of a compound of the present disclosure (e.g., a halogen or pseudohalogen as R1 in a compound of formula (I)) and create a permanent dipole moment for the compound. In some variations, the polar group may be a halogen. In some variations, the polar group may be a pseudohalogen. The polar group may be a cyano moiety, or the polar group may be a thioisocyanate moiety.

[0050] In some variations, the polar group is an NCS moiety. The NCS moiety remains polarizable, but has a reduced permanent dipole moment, making it less likely to form dipole-dipole interactions. Dimerization leads to increased viscosity and consequently worse responsiveness, for example, when used as a liquid crystal-based fast tunable lens. In some variations, the compounds of the present disclosure include optional lateral moieties (e.g., R2 and R3 in the compound of formula (I)). These lateral moieties are outside the central axis of the compound. The lateral moieties provide repulsive forces that increase the space between the compounds, thereby further reducing viscosity.

[0051] (terminal group) As described herein, a saturated terminal substituent opposite the polar group (e.g., substituents R5 in formula (II), R6 in formula (III), R7 in formula (IV), R8 in formula (V), or R9 in formula (VI)) can increase the intermolecular distance between the compounds, thereby further reducing intermolecular interactions in the composition. In some variations, the non-polar terminal group is a saturated alkyl group. In further variations, the saturated alkyl group is a C 1~10 Saturated alkyl group, or C 1~5 It may be a saturated alkyl group. In a further variation, the alkyl group is 1~10It may be a saturated cycloalkyl group, for example a cyclohexyl group. The length or size of the saturated alkyl group can reduce the viscosity of the compound or composition. When used as a liquid crystal, reducing the viscosity of the compound improves the response speed of the liquid crystal adjustable lens in the visible spectrum. The reduced viscosity can also provide a larger adjustment range and aperture of the lens, assuming the same figure of merit in the visible spectrum, as discussed herein.

[0052] (composition) In some variations, the present disclosure relates to compositions that include a plurality of compounds described herein. By combining a plurality of compounds into a composition, the melting point of the liquid crystal can be lowered so that the liquid crystal composition has a lower melting point. Furthermore, the clearing temperature can be increased so that the composition is not isotropic.

[0053] Any number of compounds can be used in the composition. In some non-limiting variations, the composition can include any number of compounds between 1 and 20 as disclosed herein. In some variations, the composition can include any number of compounds between 1 and 15 as disclosed herein. In some variations, the composition can include any number of compounds between 1 and 10 as disclosed herein. In some variations, the composition can include any number of compounds between 1 and 5 as disclosed herein. The relative amounts of different compounds in the composition can be any amount and do not have to be equal.

[0054] The melting temperature of the liquid crystal can be further reduced by combining different compounds of the present disclosure to form the disclosed compositions. The resulting eutectic composition has a lower effective melting point temperature compared to the melting point of a single compound. The composition can include multiple compounds with different chemical compositions.

[0055] By reducing the intermolecular interactions between the compounds, the viscosity and melting point of the composition can be reduced while maintaining or increasing the clearing point. Reducing the viscosity while increasing the rotational elastic constant (K33) shortens the response time of the liquid crystal material. Intermolecular interactions that increase viscosity include dipole-dipole interactions. Smaller compounds (e.g., two rings) can reduce the melting point and reduce the viscosity. Larger compounds with delocalized electrons over longer intramolecular distances can increase the polarization of the composition.

[0056] In some variations, the polar group can be selected to reduce dimerization of the compound. For compounds of formula (I), R1 can be a substituent such as thioisocyanate that is polarizable but has a small permanent dipole moment and is therefore unlikely to form dipole-dipole interactions.

[0057] In the composition, different compounds having different levels of electron delocalization are provided. Different types of compositions defined by formulas (IV), (V) and (VI) exist in the composition. Different combinations of lateral substituents R2 and R3 reduce intermolecular interactions by providing repulsive forces to other molecules.

[0058] Tables 1A-1C show non-limiting exemplary composition combinations. [Table 1] [Table 2] [Table 3]

[0059] In some variations, the composition comprises a compound having the structure of formula (IV), a compound having the structure of formula (V), and a compound having the structure of formula (VI), as described herein. In further variations, the composition comprises two or more compounds having the structure of formula (IV), a compound having the structure of formula (V), and / or a compound having the structure of formula (VI).

[0060] In some variations, in the compound having the structure of formula (IV), R1 is NCS, R2 is H or F, R3 is H or F, and R7 is selected from C2H5, C4H9, and C2H5O. In some variations, R2 is F. In a further variation, in the compound having the structure of formula (IV), R1 is NCS, R2 is F, R3 is H or F, and R7 is selected from -OC2H5, -OC4H9, and -OC5H. 11 In a further variation, the composition comprises 1 to 6 compounds of Table 1A. In a further variation, the composition comprises each compound of Table 1A.

[0061] In some variations, in the compound having the structure of formula (V), R1 is NCS, R2 is H or F, R3 is H or F, and R8 is selected from the group consisting of C3H7 and C5H 11 In some variations, R2 and R3 are F. In a further variation, in the compound having the structure of formula (V), R1 is NCS, R2 is F, R3 is H or F, and R8 is selected from C3H7 and C5H 11 In a further variation, the composition includes two compounds having the structure of formula (V), where in the first compound, R1 is NCS, R2 and R3 are F, and R8 is C3H7, and in the second compound, R1 is NCS, R2 and R3 are F, and R8 is C5H 11 (as shown in Table 1B).

[0062] In some variations, in a compound having the structure of formula (VI), R1 is NCS, R2 is H or F, R3 is H or F, and R9 is selected from C2H5 and C4H9. In some variations, R2 is F and R3 is H or F. In some variations, R2 is F and R3 is H. In a further variation, the composition comprises two compounds having the structure of formula (VI), where in the first compound, R1 is NCS, R2 is F, R3 is H, and R9 is C2H5, and in the second compound, R1 is NCS, R2 is F, R3 is H, and R9 is C4H9 (as in Table 1C).

[0063] (Liquid crystal materials) As described herein, the individual compounds in the composition have reduced intermolecular interactions, reduced permanent dipole moment, and increased intermolecular distance compared to those with CN polar substituents. The combination of these properties reduces rotational viscosity γ1 while increasing K33 and Δn (refractive index proportional to polarizability) in the visible spectrum, improving the response speed and tunability of liquid crystal tunable lenses. The reduced rotational viscosity can also provide a larger tuning range and aperture of the lens.

[0064] Table 2 provides a comparison of the properties of the compositions of Tables 1A-1C with two conventional reference compositions 1 and 2. [Table 4]

[0065] Δn corresponds to the net change in refractive index between the long and transverse axes of the molecule. The Δn of 0.39 for wavelengths in the visible spectrum is a substantial increase over reference compositions 1 and 2.

[0066] In some variations, the compounds and compositions have a higher K33. Higher K33 improves the adjustability of the lens. Higher K33 also has a larger energy barrier against thermal fluctuations, thereby reducing the scattering of light incident on the liquid crystal material containing the compound or composition in the visible spectrum. The K33 of 29.8 is substantially increased over reference compositions 1 and 2.

[0067] The compounds and compositions have a lower rotational viscosity than the compositions of Tables 1A-1C. Lower rotational viscosity allows for faster adjustment of the liquid crystal.

[0068] Δn 2 *The figure of merit (FoM) in the visible spectrum of the liquid crystal ophthalmic lenses, which is equal to K33 / y1, is substantially greater for the compositions described in Tables 1A-1C than for the conventional reference compositions 1 and 2, with respect to wavelengths in the visible spectrum.

[0069] Although some embodiments have been described, those skilled in the art will appreciate that various modifications, alternative configurations, and equivalents may be used without departing from the spirit of the present disclosure. Moreover, some well-known processes and elements have not been described to avoid unnecessarily obscuring the embodiments disclosed herein. Thus, the above description should not be taken as limiting the scope of this document.

[0070] Those skilled in the art will appreciate that the embodiments disclosed herein are taught by way of example and not by way of limitation. Thus, the elements contained in the above description or shown in the accompanying drawings should be interpreted as illustrative and not in a limiting sense. The following claims are intended to cover all the general and specific features described herein, as well as the description of the scope of the methods and systems that may be taken as a matter of language but falling therebetween.

Claims

1. 1. A composition comprising a first compound having the structure of Formula (IV), a second compound having the structure of Formula (IV), a third compound having the structure of Formula (IV), a fourth compound having the structure of Formula (IV), a fifth compound having the structure of Formula (IV), a sixth compound having the structure of Formula (IV), a seventh compound having the structure of Formula (V), an eighth compound having the structure of Formula (V), a ninth compound having the structure of Formula (VI), and a tenth compound having the structure of Formula (VI): and In the first compound, R 1 is NCS, R 2 is F, R 3 is H, and R 7 is C 2 H 5 ; In the second compound, R 1 is NCS, R 2 is F, R 3 is H, and R 7 is C 4 H 9 ; In the third compound, R 1 is NCS, R 2 is F, R 3 is H, and R 7 is C 5 H 11 ; In the fourth compound, R 1 is NCS, R 2 is F, R 3 is F, and R 7 is C 2 H 5 O; In the fifth compound, R 1 is NCS, R 2 is F, R 3 is F, and R 7 is C 4 H 9 O; In the sixth compound, R 1 is NCS, R 2 is F, R 3 is F, and R 7 is C 5 H 11 O; In the seventh compound, R 1 is NCS, R 2 is F, R 3 is F, and R 8 is C 3 H 7 ; In the eighth compound, R 1 is NCS, R 2 is F, R 3 is F, and R 8 is C 5 H 11 ; In the ninth compound, R 1 is NCS, R 2 is F, R 3 is H, and R 9 is C 2 H 5 ; The composition according to the tenth embodiment, wherein R 1 is NCS, R 2 is F, R 3 is H, and R 9 is C 4 H 9 .

2. The composition of claim 1, wherein the first compound is 21% molar percent of the composition.

3. The composition of claim 1, wherein the second compound is 23% molar percent of the composition.

4. The composition of claim 2, wherein the third compound is 7% molar percent of the composition.

5. The composition of claim 2, wherein the fourth compound is 5% molar percent of the composition.

6. The composition of claim 2, wherein the fifth compound is 6% molar percent of the composition.

7. The composition of claim 2, wherein the sixth compound is 4% molar percent of the composition.

8. The composition of claim 2, wherein the seventh compound is 6% molar percent of the composition.

9. The composition of claim 2, wherein the eighth compound is 5% molar percent of the composition.

10. The composition of claim 2, wherein the ninth compound is 8% molar percent of the composition.

11. The composition of claim 2, wherein the tenth compound is 14% molar percent of the composition.

12. A liquid crystal cell comprising a first transparent substrate and a second transparent substrate opposed to each other with a liquid crystal layer therebetween, A liquid crystal cell, wherein the liquid crystal layer comprises a compound according to any one of claims 1 to 11.

13. A liquid crystal lens comprising a first liquid crystal cell, a second liquid crystal cell and a third liquid crystal cell, each of the first liquid crystal cell, the second liquid crystal cell and the third liquid crystal cell being as defined in claim 12.

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