Mesogen compounds

Abstract

To provide mesogen compounds.SOLUTION: The present invention relates to optionally polymerizable mesogen compounds that include a polyvalent non-mesogenic core X to which is bonded three or four separate extensions, where each extension independently includes, in sequence, a linking group -L- and a mesogen group -[Mesogen]. The mesogen compounds are represented by the following Formula (I). With reference to Formula (I), v is 3 or 4; t is 0 or 1; at least one Mesogen includes at least four cyclic groups; each -L- independently has an average chain length of at least 15 bonds; and at least one -L- has an average chain length of at least 25 bonds. Also described are liquid crystal compositions that include such mesogen compounds, and optical elements that include such mesogen compounds.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to optionally polymerizable mesogenic compounds comprising a multivalent non-mesogenic core to which are attached three or four distinct extensions, each extension independently comprising in turn a linking group and a mesogenic group, liquid crystal compositions comprising such mesogenic compounds and optical elements comprising such mesogenic compounds. [Background technology]

[0002] The molecules of liquid crystals can typically align with one another in substantially one direction, resulting in a fluid material with anisotropic properties, such as with respect to optical, electromagnetic and / or mechanical properties. Mesogens are typically described as the primary or fundamental units (or segments or groups) of liquid crystal material that induce and / or are induced into structural order in liquid crystals (such as other liquid crystal materials present).

[0003] Liquid crystal polymers are polymers that can form domains of highly ordered structure while in the liquid phase. Liquid crystal polymers have a wide range of applications, including engineering plastics and gels for liquid crystal displays (LCDs). The structure of liquid crystal polymers can be described as consisting of closely packed, elongated polymer chains that are self-reinforced up to approximately the melting point of the polymer.

[0004] Dichroism may occur in liquid crystals containing mesogenic compounds due to optical anisotropy of the molecular structure, or due to the presence of impurities, or due to the presence of dichroic dyes and / or photochromic-dichroic materials. As used herein, the term "dichroic" and similar terms such as "dichroic" refer to the ability to absorb one of two orthogonal plane-polarized components of radiation (including transmitted and / or reflected radiation) more strongly than the other orthogonal plane-polarized component. Photochromic-dichroic materials have both photochromic and dichroic properties. Photochromic-dichroic materials may, in some instances, be described as comprising a photochromic molecule (or core or moiety), to which at least one extension group is covalently attached, at least a portion of which can be aligned with (or by) the mesogenic material.

[0005] When used in combination with a liquid crystal material, such as a mesogenic compound, the dichroic properties of the photochromic-dichroic compound, such as polarization efficiency and absorption ratio, can be enhanced. Without intending to be bound by any theory, based on the evidence at hand, it is believed that aligning a photochromic-dichroic compound with an aligned mesogenic compound enhances the dichroic properties of the photochromic-dichroic compound, such as improving the absorption ratio (AR) value.

[0006] The photochromic properties of a photochromic-dichroic compound can be enhanced by a chemical environment in which the photochromic moiety can efficiently undergo a reversible conformational change between an absorbing (or colored) and a non-absorbing (or non-colored) state. Examples of quantifiable photochromic properties include, but are not limited to, the degree of bleaching (bleaching half-life, T 1 / 2These include the change in optical density (sometimes referred to as ΔOD); the change in optical density at saturation (ΔOD); sensitivity (sometimes referred to as ΔOD / min); and the efficiency with which the photochromic compound absorbs the radiation required to activate the photochromic compound (sometimes referred to as chromaticity). The chemical environment provided by aligned mesogenic compounds can enhance the dichroic properties of the dichroic portion of the photochromic-dichroic compound, while in some cases providing a chemical environment that conversely limits or inhibits efficient reversible conformational change of the photochromic portion of the photochromic-dichroic compound.

[0007] It would be desirable to develop new mesogenic compounds that can further enhance the dichroic properties of dichroic materials, such as photochromic-dichroic compounds. Moreover, it would be desirable for such newly developed mesogenic compounds to maintain or enhance the photochromic properties of the photochromic-dichroic materials with which they are used. Summary of the Invention [Means for solving the problem]

[0008] According to the present invention, a compound represented by the following formula (I) [ka] (In the formula, v is 3 or 4; t is 0 or 1; (A) each mesogen is independently represented by the following formula (II) for each v: [ka] With respect to formula (II), P is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, acrylamide, methacrylamide, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic ester, siloxane, carbosilane, cyano, or nitro; S1, S2, S3 and S4 are independently for each occurrence selected from a spacer unit selected from -CH2-; -O-; -C(O)-; -N=N-; -CH=CH-; -C≡C-; -CH=N-; -CF2-; or -NH-, with the proviso that when two spacer units containing heteroatoms are linked together, the spacer units are linked such that the heteroatoms are not directly linked to each other; d is between 0 and 20; e, f and g are, independently for each occurrence, 0 to 3; Q1, Q2 and Q3, for each occurrence, are independently a divalent radical selected from the group consisting of an unsubstituted or substituted cycloaliphatic group; an unsubstituted or substituted heterocycloaliphatic group; an unsubstituted or substituted aryl group; and an unsubstituted or substituted heteroaryl group; and each of the substituents of the cycloaliphatic group, each of the substituents of the heterocycloaliphatic group, each of the substituents of the aryl group and each of the substituents of the heteroaryl group are independently in each occurrence -(S1) d -P, where S1, d and P are each as defined for formula (II); and e' and f', independently for each occurrence, are 0 to 6, provided that the sum of e' and f' is at least 2; (B) each -L-, independently for each v, is represented by the following formula (III): [ka] wherein: (i) y is 0 to 30; (ii) each A, independently for each y, is selected from the group consisting of a single bond, an aliphatic group, and a haloaliphatic group. is a divalent group selected from (iii) each B, for each y, is independently: -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R a is independently selected from methyl, ethyl, or phenyl, and each R3, for each n, is independently selected from methyl, ethyl, or phenyl; [ka] wherein t' is 1 to 4, u' is, independently for each t', 1 to 5, and each R 16 is independently selected for each t′ from methyl, ethyl, or phenyl, and each R 17 is independently selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each R5 is independently selected from methyl, ethyl, or phenyl; and (iv) E is a divalent radical selected from the group consisting of an aliphatic group and a haloaliphatic group; (C) X is a polyvalent group selected from the group consisting of Si; N; Ge; P (i.e., phosphorus); a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms; an unsubstituted or substituted cyclic aliphatic group; an unsubstituted or substituted heterocyclic aliphatic group; an unsubstituted or substituted aryl group; and an unsubstituted or substituted heteroaryl group; and each of the substituents of the aliphatic group, the substituent of the cyclic aliphatic group, the substituent of the heterocyclic aliphatic group, the substituent of the aryl, and the substituent of the heteroaryl is, independently in each occurrence, -(S1). d -P, where S1, d and P are each as defined for formula (II); (D) R4 is -(S1) d -P (wherein S1, d and P are each as defined for formula (II)); =O; and unsubstituted or substituted phenyl groups (wherein each phenyl substituent is independently -(S1) d -P, where S1, d and P are each as defined for formula (II). is selected from the group consisting of provided that at least one mesogen contains at least four cyclic groups; and each -L- independently contains an average chain length of at least 15 bonds, and further provided that at least one -L- contains an average chain length of at least 25 bonds. There is provided a mesogen-containing compound represented by:

[0009] Further, according to the present invention, there is provided a liquid crystal composition comprising a mesogen-containing compound of the present invention as described with respect to formula (I).

[0010] Further according to the present invention there is provided an optical element comprising a substrate and a layer on at least a part of a surface of the substrate, the layer comprising a mesogen-containing compound of the present invention as described with respect to formula (I).

[0011] The features which characterize the invention are pointed out with particularity in the claims, which are annexed to and form a part of this disclosure. These and other features of the invention, its advantages of operation, and certain objects attained by its uses will be more fully understood from the following detailed description, in which non-limiting embodiments of the invention are shown and described. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The mesogenic compounds of the present invention, such as those represented by formula (I), are referred to herein as "mesogen compounds", "mesogenic compounds", "mesogen-containing compounds", "star mesogenic compounds" and "star mesogen-containing compounds".

[0013] As used herein, the articles "a," "an," and "the" include plural referents unless expressly and unambiguously limited to one referent.

[0014] Unless otherwise indicated, all ranges or ratios disclosed herein should be understood to encompass any and all subranges or subratios subsumed therein. For example, a specified range or ratio of "1 to 10" should be considered to include any and all subranges from a minimum value of 1 to a maximum value of 10 (inclusive), i.e., all subranges or subratios beginning with a minimum value of 1 or greater and ending with a maximum value of 10 or less, such as, but not limited to, 1 to 6.1, 3.5 to 7.8, and 5.5 to 10.

[0015] As used herein, unless otherwise indicated, a left-to-right representation of a linking group, such as a divalent linking group, includes other suitable orientations, such as, but not limited to, a right-to-left orientation. For non-limiting illustrative purposes, a left-to-right representation of a divalent linking group [ka] or the equivalent -C(O)O-, its right-to-left representation [ka] or the equivalents -O(O)C- or -OC(O)-.

[0016] Except in the examples or where otherwise indicated, all numbers expressing quantities of ingredients, reaction conditions, and so forth used in the specification and claims are to be understood as being modified in all instances by the term "about."

[0017] As used herein, polymer molecular weight values, such as weight average molecular weight (Mw) and number average molecular weight (Mn), are measured by gel permeation chromatography using appropriate standards, such as polystyrene standards.

[0018] As used herein, the polydispersity index (PDI) value represents the ratio of the polymer weight average molecular weight (Mw) to the number average molecular weight (Mn) (ie, Mw / Mn).

[0019] As used herein, the term "polymer" refers to homopolymers (eg, prepared from a single monomer type), copolymers (eg, prepared from at least two monomer types), and graft polymers.

[0020] As used herein, "at least one of" is synonymous with "one or more of," regardless of whether the elements are listed conjunctively or disjunctively. For example, the phrases "at least one of A, B, and C" and "at least one of A, B, or C" mean any one of A, B, or C, respectively, or any combination of any two or more of A, B, or C. For example, A only, or B only, or C only, or A and B, or A and C, or B and C, or all of A, B, and C.

[0021] As used herein, "selected from" is synonymous with "selected from," regardless of whether the elements are listed conjunctively or disjunctively. Additionally, the phrases "selected from A, B, and C" and "selected from A, B, or C" mean any one of A, B, or C, respectively, or any combination of any two or more of A, B, or C. For example, A only, or B only, or C only, or A and B, or A and C, or B and C, or all of A, B, and C.

[0022] The description of the invention herein may describe certain features as "particularly" or "preferably" within certain limitations (e.g., "preferably," "more preferably," or "even more preferably" within certain limitations). It is to be understood that the invention is not limited to or by these particular or preferred limitations, but rather encompasses the entire scope of the disclosure.

[0023] As used herein, the term "photochromic" and similar terms such as "photochromic compound" refer to having an absorption spectrum for at least visible radiation that changes in response to the absorption of at least actinic radiation. Additionally, as used herein, the term "photochromic material" refers to any substance that is adapted to exhibit photochromic properties (such as adapted to have an absorption spectrum for at least visible radiation that changes in response to the absorption of at least actinic radiation) and that includes at least one photochromic compound.

[0024] The term "actinic radiation" as used herein means electromagnetic radiation capable of producing a response in a material, such as, but not limited to, transforming a photochromic material from one form or state to another, as described in more detail herein.

[0025] As used herein, the term "photochromic material" includes thermally reversible photochromic materials and compounds as well as non-thermally reversible photochromic materials and compounds. As used herein, the term "thermally reversible photochromic compound / material" refers to a compound / material that can be converted from a first state (such as a "transparent state") to a second state (such as a "colored state") in response to actinic radiation and can return to the first state in response to thermal energy. As used herein, the term "non-thermally reversible photochromic compound / material" refers to a compound / material that can be converted from a first state (such as a "transparent state") to a second state (such as a "colored state") in response to actinic radiation and can return to the first state in response to actinic radiation of substantially the same wavelength as the absorption of the colored state.

[0026] The terms "first" and "second" as used herein to modify the term "state" are not intended to refer to any particular order or chronological sequence, but rather to two The term "photochromic compound" is intended to refer to different states or properties. For non-limiting illustrative purposes, the first and second states of a photochromic compound may differ with respect to at least one optical property, such as, but not limited to, the absorption of visible light and / or UV radiation. Thus, according to various non-limiting embodiments disclosed herein, a photochromic compound used in connection with the present invention may have different absorption spectra in each of the first and second states. For example, but not limited to, herein, a photochromic compound used in connection with the present invention may be transparent in the first state and colored in the second state. Alternatively, a photochromic compound used in connection with the present invention may have a first color in the first state and a second color in the second state. Furthermore, a photochromic-dichroic compound used in connection with the present invention may have a first orientation in the first state and a second orientation in the second state, where one of the first orientation and the second orientation is substantially non-oriented.

[0027] The term "optical" as used herein means relating to or associated with light and / or vision. For example, according to various non-limiting embodiments disclosed herein, optical articles or elements or devices can be selected from ophthalmic articles, elements and devices, display articles, elements and devices, windows, mirrors, and active and passive liquid crystal cell articles, elements and devices.

[0028] The term "ophthalmic" as used herein means relating to or associated with the eye and vision. Non-limiting examples of ophthalmic articles or elements include corrective and non-corrective lenses, including multivision lenses (such as, but not limited to, bifocal, trifocal and progressive lenses), which may be single vision or segmented or non-segmented multivision lenses, as well as other elements used to correct, protect or enhance vision (cosmetic or otherwise), such as, but not limited to, contact lenses, intraocular lenses, magnifying lenses and protective lenses or visors.

[0029] The term "display" as used herein means a visible or machine-readable representation of information in words, numbers, symbols, designs or drawings. Non-limiting examples of display elements include screens, monitors and security elements such as security marks.

[0030] As used herein, the term "window" means an opening adapted to allow the transmission of radiation. Non-limiting examples of windows include automobile and aircraft transparencies, windshields, filters, shutters, and optical switches.

[0031] As used herein, the term "mirror" means a surface that specularly reflects a large portion of incident light.

[0032] As used herein, the term "liquid crystal cell" refers to a structure that contains liquid crystal material that can be aligned. A non-limiting example of a liquid crystal cell element is a liquid crystal display.

[0033] As used herein, spatial or directional terms such as "left," "right," "inner," "outer," "upper," "lower," and the like may be used to describe various embodiments of the present invention. However, it should be understood that the present invention may assume a variety of alternative orientations, and thus such terms should not be considered limiting.

[0034] As used herein, "formed on," "deposited on," and "provided on" The terms "coated on," "existing on," or "disposed on" mean formed, deposited, provided, applied, present, or positioned on, but not necessarily in direct (or adjacent) contact with, an underlying element or a surface of an underlying element. For example, a layer "disposed on" a substrate does not exclude the presence of one or more other layers, coatings, or films of the same or different composition located between the disposed or formed layer and the substrate.

[0035] All documents, including but not limited to issued patents and patent applications, mentioned herein are to be deemed "incorporated by reference" in their entirety, unless otherwise indicated.

[0036] As used herein, the term "(meth)acrylate" and similar terms such as "(meth)acrylic acid ester" refer to methacrylate and / or acrylate. As used herein and according to some embodiments, the term "(meth)acrylate" and related terms such as "(meth)acrylate group" and "(meth)acrylate substituent", such as those relating to the groups and substituents of various groups of the mesogenic compounds of the present invention, include substances represented by -OC(O)-C(R')=CH2, where R' is hydrogen or methyl. As used herein, the term "(meth)acrylic acid" refers to methacrylic acid and / or acrylic acid. As used herein, the term "(meth)acrylamide" refers to acrylamide (-N(H)-C(O)-C(H)=CH2) and methacrylamide (-N(H)-C(O)-C(CH3)=CH2).

[0037] As used herein and according to some embodiments, the term "carboxylic acid", such as in relation to groups and substituents of various groups of the mesogen-containing compounds of the present invention, and related terms such as "carboxylic acid group" and "carboxylic acid substituent", includes substances represented by -C(O)OH.

[0038] As used herein and according to some embodiments, the term "carboxylate", such as in relation to groups and substituents of various groups of the mesogen-containing compounds of the present invention, and related terms such as "carboxylate group" and "carboxylate substituent", refers to an entity represented by -C(O)OR, where R is, for example, selected from an aliphatic group, a cycloaliphatic group, a heterocycloaliphatic group, an aryl group and a heteroaryl group.

[0039] As used herein, the term "aliphatic" and related terms such as "aliphatic group" refer to C1 to C 20 Aliphatic group or C1-C 10 Aliphatic group, or C1-C6 aliphatic group, refers to a non-cyclic and non-aromatic hydrocarbon group containing at least one carbon atom, for example 1-20 carbon atoms, which may be linear or branched; optionally containing one or more internal and / or terminal alkene (or alkenyl) groups; and optionally containing one or more internal and / or terminal alkyne (or alkynyl) groups. When containing two or more alkene groups, the alkene groups of the aliphatic group may be conjugated and / or non-conjugated. When containing two or more alkyne groups, the alkyne groups of the aliphatic group may be conjugated and / or non-conjugated. When containing at least one alkene group and at least one alkyne group, the alkene and alkyne groups of the aliphatic group may be conjugated and / or non-conjugated with respect to each other.

[0040] Examples of aliphatic groups include, but are not limited to, alkyl groups. As used herein, the terms "alkyl" and related terms such as "alkyl group" refer to C1 to C6 alkyl groups. 20 Alkyl group or C1-C 10 It means a group containing at least one carbon atom, e.g., 1-20 carbon atoms, such as an alkyl group or a C1-C6 alkyl group, which is linear or branched; and saturated (thus not including alkene and alkyne groups). Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, Examples include n-butyl, isobutyl, sec-butyl, t-butyl, linear or branched pentyl, linear or branched hexyl, linear or branched heptyl, linear or branched octyl, linear or branched nonyl, linear or branched decyl, linear or branched undensyl, linear or branched dodecyl, linear or branched tridecyl, linear or branched tetradecyl, linear or branched pentadecyl, linear or branched hexadecyl, linear or branched heptadecyl, linear or branched octadecyl, linear or branched nonadecyl, and linear or branched eicosanyl.

[0041] As used herein, references to "straight chain or branched" groups such as, but not limited to, straight chain or branched alkyl are intended to include, by way of non-limiting example only, methylene or methyl groups; straight chain C2-C 20 Straight-chain groups such as alkyl groups; and branched C3-C 20 It is understood to include suitably branched groups such as, but not limited to, alkyl groups.

[0042] Examples of aliphatic groups include, but are not limited to, alkenyl groups. As used herein, the term "alkenyl" and related terms such as "alkenyl group" refer to any C2-C 20 Alkenyl group, or C2-C 10 Alkenyl groups, or C2-C6 alkenyl groups, refer to groups containing at least two carbon atoms, e.g., 2-20 carbon atoms, which are linear or branched; and which contain one or more internal and / or terminal alkene (or alkenyl) groups. Examples of alkenyl groups include, but are not limited to, the examples of linear or branched alkyl groups described herein above having at least two carbon atoms and at least one alkene (or alkenyl) group, such as, but not limited to, ethenyl, linear or branched propenyl, linear or branched butenyl, linear or branched pentenyl, linear or branched hexenyl, etc.

[0043] Examples of aliphatic groups include, but are not limited to, alkynyl groups. As used herein, the term "alkynyl" and related terms such as "alkynyl group" refer to C2-C 20 Alkynyl group or C2-C 10 Alkynyl groups, or C2-C6 alkynyl groups, refer to groups containing at least two carbon atoms, e.g., 2-20 carbon atoms, which are linear or branched; and which contain one or more internal and / or terminal alkyne (or alkynyl) groups. Examples of alkynyl groups include, but are not limited to, the examples of linear or branched alkyl groups described herein above having at least two carbon atoms and at least one alkyne (or alkynyl) group, such as, but not limited to, ethynyl, propynyl, butynyl, linear or branched pentynyl, linear or branched hexynyl, etc.

[0044] As used herein, the terms "haloaliphatic" and related terms such as "haloaliphatic group" refer to any group consisting of C1 to C 20 Haloaliphatic group, or C1-C 10Haloaliphatic group, or C1-C6 haloaliphatic group, refers to an acyclic and non-aromatic hydrocarbon group containing at least one carbon atom, for example 1-20 carbon atoms; containing at least one halo group selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I); being linear or branched; optionally containing one or more internal and / or terminal alkene groups; and optionally containing one or more internal and / or terminal alkyne groups. When containing two or more alkene groups, the alkene groups of the haloaliphatic group can be conjugated and / or non-conjugated. When containing two or more alkyne groups, the alkyne groups of the haloaliphatic group can be conjugated and / or non-conjugated. When containing at least one alkene group and at least one alkyne group, the alkene groups and alkyne groups of the haloaliphatic group can be conjugated and / or non-conjugated with respect to each other. At least one available hydrogen and up to all available hydrogens of a haloaliphatic group can be replaced with a halo group, such as those selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I). As a result, the term "haloaliphatic" as used herein is intended to encompass related terms such as, but not limited to, "perhaloaliphatic" and "perhaloaliphatic group." Includes terms such as:

[0045] Examples of haloaliphatic groups include, but are not limited to, haloalkyl groups. As used herein, the terms "haloalkyl" and related terms such as "haloalkyl group" refer to C1-C 20 Haloalkyl or C1-C 10Haloalkyl, or C1-C6 haloalkyl, refers to a group containing at least one carbon atom, e.g., 1-20 carbon atoms, being linear or branched; containing at least one halo group, such as those selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I); and being saturated (thus not containing alkene and alkyne groups). At least one available hydrogen and up to all available hydrogens of the haloalkyl group can be replaced with a halo group, such as those selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I). As a result, the term "haloalkyl" as used herein includes related terms such as, but not limited to, "perhaloalkyl" and "perhaloalkyl group." Examples of haloalkyl groups include, but are not limited to, the examples of straight chain or branched alkyl groups described above containing at least one halo group, such as, but not limited to, halomethyl, haloethyl, straight chain or branched halopropyl, straight chain or branched halobutyl, straight chain or branched halopentyl, straight chain or branched halohexyl, etc., each independently containing at least one halo group.

[0046] Examples of haloaliphatic groups include, but are not limited to, haloalkenyl groups. As used herein, the term "haloalkenyl" and related terms such as "haloalkenyl group" refer to any C2-C 20 Haloalkenyl, or C2-C 10Haloalkenyl, or C2-C6 haloalkenyl, refers to a group containing at least two carbon atoms, e.g., 2-20 carbon atoms, which is linear or branched; contains at least one halo group, such as those selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I); and contains one or more internal and / or terminal alkene (or alkenyl) groups. Examples of haloalkenyl groups include, but are not limited to, the linear or branched alkyl groups described above having at least two carbon atoms, at least one alkene (or alkenyl) group and at least one halo group, such as, but not limited to, haloethenyl, linear or branched halopropenyl, linear or branched halobutenyi, linear or branched halopentenyl, linear or branched halohexenyi, each of which independently contains at least one halo group.

[0047] Examples of haloaliphatic groups include, but are not limited to, haloalkynyl groups. As used herein, the term "haloalkynyl" and related terms such as "haloalkynyl group" refer to any C2-C 20 Haloalkynyl, or C2-C 10 Haloalkynyl, or C2-C6 haloalkynyl, refers to a group containing at least two carbon atoms, e.g., 2-20 carbon atoms, being linear or branched; containing at least one halo group (or halogen group) such as those selected from fluoro (F), chloro (Cl), bromo (Br) and / or iodo (I); and containing one or more internal and / or terminal alkyne (or alkynyl) groups. Examples of haloalkynyl groups include, but are not limited to, the linear or branched alkyl groups listed above having at least two carbon atoms, at least one alkyne (or alkynyl) group and at least one halo group, such as, but not limited to, haloethynyl, halopropynyl, halobutynyl, linear or branched halopentynyl, linear or branched halohexynyl, and the like, each independently containing at least one halo group.

[0048] As used herein, the term "cycloaliphatic" and related terms such as "cycloaliphatic group" refer to a cycloaliphatic group having a C3 to C 20 Cycloaliphatic group, or C3~C 10 Cyclic and aromatic groups containing at least 3 carbon atoms, for example 3 to 20 carbon atoms, such as cycloaliphatic groups or C3 to C8 cycloaliphatic groups. "Aromatic" refers to a non-aromatic hydrocarbon group having at least one unsaturated group selected from an alkene and / or an alkyne; optionally containing two or more fused cycloaliphatic rings.

[0049] Examples of cyclic aliphatic groups include, but are not limited to, cycloalkyl groups. As used herein, the terms "cycloalkyl" and related terms such as "cycloalkyl group" refer to any group having a C to C 20 Cycloalkyl group or C3-C 10 Cycloalkyl groups, or C3-C8 cycloalkyl groups, refer to groups containing at least three carbon atoms, e.g., 3-20 carbon atoms; optionally containing at least one unsaturated group selected from an alkene and / or an alkyne; and optionally containing two or more fused cyclic aliphatic rings. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, norbornyl, decahydronaphthalenyl, tetradecahydroanthracenyl, tetradecahydrophenanthrenyl, and dodecahydro-1H-phenalenyl.

[0050] As used herein, the term "heterocyclic aliphatic" and related terms such as "heterocyclic aliphatic group" refer to a heterocyclic ring system having a C2-C 20 Heterocyclic aliphatic group or C2-C 10Heterocyclic aliphatic group, or C2-C8 heterocyclic aliphatic group, refers to a cyclic and non-aromatic group containing at least two carbon atoms, e.g., 2-20 carbon atoms; having at least one heteroatom in the ring, such as, but not limited to, O, S, N, P, and combinations thereof; optionally containing at least one unsaturated group selected from an alkene and / or an alkyne; and optionally containing two or more fused non-aromatic rings, at least one of which is a fused heterocyclic aliphatic ring.

[0051] Examples of heterocyclic aliphatic groups include, but are not limited to, heterocycloalkyl groups. As used herein, the terms "heterocycloalkyl" and related terms such as "heterocycloalkyl group" refer to any group having a C2-C 20 Heterocycloalkyl group or C2-C 10 Heterocycloalkyl groups, or C2-C8 heterocycloalkyl groups, refer to groups containing at least two carbon atoms, e.g., 2-20 carbon atoms; having at least one heteroatom in the ring, such as, but not limited to, O, S, N, P, and combinations thereof; optionally containing at least one unsaturated group selected from an alkene and / or an alkyne; and optionally containing two or more fused non-aromatic rings, at least one of which is a fused heterocycloalkyl ring. Examples of heterocycloalkyl groups include, but are not limited to, imidazolyl, tetrahydrofuranyl, tetrahydropyranyl, piperidinyl, piperazinyl, morpholinyl, 7-oxabicyclo[2.2.1]heptanyl, octahydrocyclopenta[b]pyranyl, and octahydro-1H-isochromenyl.

[0052] As used herein, the term "aryl" and related terms such as "aryl group" refer to any C6-C 20 Aryl group or C6-C 14By aryl is meant a cyclic aromatic group containing at least six carbon atoms; optionally containing at least two fused rings, at least one of which is a fused aromatic ring. Examples of aryl groups include, but are not limited to, phenyl, naphthalenyl, anthracenyl, phenanthrenyl, triphenylenyl, 9,10-dihydroanthracenyl, 9,10-dihydrophenanthrenyl, and triptycenyl.

[0053] As used herein, the term "heteroaryl" and related terms such as "heteroaryl group" refer to any heteroaryl having a C3-C 20 Heteroaryl group or C5-C 14 Heteroaryl groups, for example, have at least three carbon atoms and a few aromatic rings, such as -O-, -N- and / or -S-. and optionally at least two fused rings, at least one of which is a fused heteroaromatic ring. Examples of heteroaryl groups include, but are not limited to, pyrazolyl, imidazolyl, triazinyl, furanyl, thiophenyl, pyranyl, pyridinyl, isoquinolinyl, and pyrimidinyl.

[0054] As used herein, the term "alkoxy" and related terms such as "alkoxy group" refer to a group represented by -OR, where R is a linear or branched alkyl group containing at least one carbon atom, such as 1 to 20 carbon atoms, e.g., C1 to C6. 20 Alkyl or C1-C 10 Alkyl, or C1-C6 alkyl; correspondingly, an alkoxy group is, for example, C1-C 20 Alkoxy or C1-C 10Examples of alkoxy groups include, but are not limited to, the examples of alkyl groups described herein above that contain a terminal divalent oxygen linkage or group (or a terminal ether linkage or group), such as, but not limited to, methoxy (CH3-O-), ethoxy (CH3CH2-O-), n-propoxy (CH3CH2CH2-O-), isopropoxy, straight-chain or branched butoxy, straight-chain or branched pentoxy, straight-chain or branched hexoxy, and the like.

[0055] As used herein, the term “amino” and related terms such as “amino group” refer to —N(R 11 )(R 12 ) wherein R 11 and R 12 are each independently selected from, for example, hydrogen, an aliphatic group, a cycloaliphatic group, a heterocycloaliphatic group, an aryl group, and a heteroaryl group. As used herein, the term "primary amino" and related terms such as "primary amino group" refer to a group represented by -NH2.

[0056] As used herein, the terms "halogen," "halogen group," and / or related terms such as "halo group" refer to a single-bonded halogen atom, such as those selected from fluoro (F), chloro (Cl), bromo (Br), and / or iodo (I).

[0057] As used herein, and unless otherwise stated, the terms "hydrogen" and related terms such as "hydrogen group" refer to a single-bonded hydrogen (-H).

[0058] With respect to formula (II) and according to some embodiments, P can be selected from the group consisting of acrylate (CH2=CHC(O)O-), methacrylate (CH2=C(CH3)C(O)O-); trihalomethacrylate (CH2=C(CX'3)C(O)O- (where each X' is independently a halogen or halo group); cyanoacrylate (CH2=C(CN)C(O)O-); oxirane. [ka] hydroxyl (-OH); primary amino (-NH2); carboxylic acid (-C(O)OH); carboxylic acid ester (-C(O)OR, as previously described herein); siloxane; carbosilane; cyano (-CN); and nitro (-NO2). Examples of trihalomethacrylates that can be selected as P include, but are not limited to, trifluoromethacrylate and trichloromethacrylate.

[0059] According to some embodiments, P in formula (II) is selected from a siloxane group. In some further embodiments, P in formula (II) is selected from a siloxane having 2 to 6 Si atoms. According to some additional embodiments, P in formula (II) is selected from a siloxane having 2 to 6 Si atoms. ) is selected from siloxane groups represented by the following formula: [ka] With respect to formula (A), n' is 1 to 5; each R 13 is independently selected for each n' from methyl, ethyl, or phenyl; and each R 14 is independently selected from methyl, ethyl, or phenyl.

[0060] According to some embodiments, P in formula (II) is selected from a carbosilane group. According to some further embodiments, P in formula (II) is selected from a carbosilane group having 2-5 Si atoms and 1-5 methylene groups between each pair of Si atoms.

[0061] According to some additional embodiments, P of formula (II) is selected from a carbosilane group represented by formula (B): [ka] With respect to Formula (B), t' is 1 to 4; u is, independently for each t', 1 to 5; 16is independently selected for each t' from methyl, ethyl, or phenyl; and each R 17 is independently selected from methyl, ethyl, or phenyl.

[0062] According to some embodiments, with respect to Formula (II) and independently for each v, the subscript d, independently for each occurrence, is from 0 to 20, or from 0 to 15, or from 0 to 12, or from 0 to 10, or from 0 to 8, or from 0 to 5.

[0063] According to some embodiments, with respect to Formula (II) and independently for each v, the subscripts e, f, and g are, independently for each occurrence, 0 to 3 (such as 0, 1, 2, or 3).

[0064] In some embodiments, for each occurrence of Formula (II), e' and f' are independently 0 to 6 (such as 0, 1, 2, 3, 4, 5, or 6 and combinations thereof), provided that the sum of e' and f' is at least 2, such as 2 to 10 (such as 2, 3, 4, 5, 6, 7, 8, 9, or 10), or 2 to 5 (such as 2, 3, 4, or 5), or 2 to 4 (such as 2, 3, or 4).

[0065] Further, with respect to formula (II), S1, S2, S3 and S4 are independently selected for each occurrence from a spacer unit selected from -CH2-; -O-; -C(O)-; -N=N-; -CH=CH-; -C≡C-; -CH=N-; -CF2-; or -NH-, with the proviso that when two spacer units containing heteroatoms are linked together, the spacer units are linked such that the heteroatoms are not directly bonded to each other. Adjacent spacer units may be linked together by any of a number of linkages, including, but not limited to, alkyl linkages; ether linkages; carboxylic acid ester linkages, -OC(O)- and / or C(O)-O-; carbonate linkages. A variety of divalent linkages can be formed, such as, for example, -OC(O)-O-; amide linkages, -NH-C(O)- and / or -C(O)-NH-; urea linkages, -NH-C(O)-NH-; carbamate linkages, -OC(O)-NH- and / or -NH-C(O)-O-; dione linkages, -C(O)-C(O)-; and combinations thereof, provided that the spacer units are attached such that the heteroatoms are not directly bonded to each other. By way of non-limiting example, and in some embodiments, a spacer unit in which heteroatoms are linked such that they are not directly bonded to each other means, but is not limited to, that -O- is not directly bonded to -O-; that -NH- is not directly bonded to -NH-; that -O- and -NH- are not directly bonded to each other; that -N=N- is not directly bonded to -N=N-; that -N=N- is not directly bonded to -O-; that -N=N- is not directly bonded to -NH-; that the nitrogen of -CH=N- is not directly bonded to the N of -CH=N-; and that the N of -CH=N- is not directly bonded to -O-, -NH-, or -N=N-.

[0066] According to some embodiments, and with respect to formula (II), S1, S2, S3 and S4, for each occurrence, are independently selected from spacer units selected from -(CH2)-, -O-, -C(O)- or -NH-; and subscripts e, f and g, for each occurrence, are independently 0 to 3 (such as 0, 1, 2 or 3), with the proviso that when two spacer units containing heteroatoms are linked together, the spacer units are linked such that the heteroatoms are not directly linked to each other.

[0067] With respect to formula (II) and according to some embodiments of the present invention, Q1, Q2 and Q3, for each occurrence, are independently selected from unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; unsubstituted or substituted naphthyl; or unsubstituted or substituted triptycenyl; each cycloalkyl substituent, each phenyl substituent, each naphthyl substituent and each triptycenyl substituent are independently selected from -(S1) d -P, where S1, d and P are each as defined for formula (II).

[0068] In some embodiments and with respect to Formula (II), Q1, Q2, and Q3, for each occurrence, are independently a divalent radical selected from the group consisting of unsubstituted or substituted 1,4-cyclohexyl; unsubstituted or substituted 1,4-phenyl; unsubstituted or substituted 1,5-naphthyl; unsubstituted or substituted 2,6-naphthyl; unsubstituted or substituted 1,8-naphthyl; and unsubstituted or substituted 1,4-triptycenyl; each 1,4-cycloalkyl substituent, each 1,4-phenyl substituent, each 1,5-naphthyl substituent, each 2,6-naphthyl substituent, each 1,8-naphthyl substituent, and each 1,4-triptycenyl substituent, are independently in each occurrence -(S1) d -P, where S1, d and P are each as defined for formula (II).

[0069] In some embodiments of the invention, for formula (II), P is selected from hydrogen, alkyl, alkoxy, acrylate, or methacrylate; and formula (III) is further described as follows: for formula (III), (i) y is 1 to 30; (ii) each A, for each y, is a divalent group selected from the group consisting of alkyl and haloalkyl; (iii) each B, for each y, is independently -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R a is independently methyl, ethyl, or phenyl, and each R3, for each n, is selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each R5 is independently selected from methyl, ethyl, or phenyl; and (iv) is a divalent radical selected from the group consisting of alkyl groups and haloalkyl groups.

[0070] The polyvalent linking group X in formula (I), in some embodiments, is selected from Si; a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; or an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms, each of the aliphatic group substituents being independently selected from -(S1) d -P, where S1, d and P are each as defined for formula (II).

[0071] In some embodiments, the polyvalent linking group X of formula (I) is selected from polyvalent siloxanes having 2 to 6 Si atoms or 2 to 5 Si atoms. In some further embodiments, the polyvalent siloxanes that can be selected for X of formula (I) are selected from linear, branched, or cyclic siloxanes having 2 to 6 Si atoms or 2 to 5 Si atoms. In some additional embodiments, the cyclic siloxanes that can be selected for X include cyclotrisiloxane and cyclotetrasiloxane.

[0072] Cyclotrisiloxanes that can be selected as X in formula (I) include, but are not limited to, those represented by the following formula (C): [ka]

[0073] With respect to formula (C), each R9 is independently methyl, ethyl, or phenyl; t in formula (I) is 0; and v in formula (I) is 3.

[0074] Cyclotetrasiloxanes that can be selected as X in formula (I) include, but are not limited to, those represented by formula (D) below. [ka]

[0075] Regarding formula (D), each R 10 is independently methyl, ethyl, or phenyl; t in formula (I) is 0; and v in formula (I) is 4.

[0076] In some embodiments, the polyvalent linking group X of formula (I) is selected from polyvalent carbosilanes having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms.

[0077] According to some further embodiments, the polyvalent linking group X of formula (I) is selected from the group consisting of Si;10 Alkyl (C1-C 10 The alkyl substituents are independently -(S1) d -P, where S1, d and P are each as defined for formula (II); a siloxane represented by the following formula (1); or a carbosilane represented by the following formula (2).

[0078] With respect to formula (1) below, each R6 is independently selected from methyl, ethyl, or phenyl. [ka]

[0079] In some embodiments, formula (1) is a non-limiting example of a branched polyvalent siloxane that can be selected as X in formula (I).

[0080] The polyvalent linking group X of formula (I), in some embodiments, is represented by formula (1), wherein each R6 is independently selected from methyl or phenyl.

[0081] With respect to formula (2) below, R7 is a divalent aliphatic group having 1 to 5 carbon atoms, and each R8 is independently selected from methyl, ethyl, or phenyl. [ka]

[0082] The polyvalent linking group X of formula (I), in some embodiments, is represented by formula (2), where R7 is a divalent C1-C5 alkyl group; and each R8 is independently selected from methyl, ethyl, or phenyl. In some embodiments, R7 of formula (2) is -CH2CH2-.

[0083] In some embodiments of the present invention and with respect to formula (I), subscript t is 0; subscript v is 4; and X is a siloxane represented by the following formula (1a): [ka]

[0084] With respect to formula (1a), d' is 0 to 3; each R 18 is independently selected for each d' from methyl, ethyl, or phenyl; and each R 19 is independently selected from methyl, ethyl or phenyl. Further, with respect to formula (1a), each of the four single bonds has unsatisfied valences extending from the two Si atoms and independently represents a single bond to a -L-[mesogenic] group (or moiety) of formula (I).

[0085] In some embodiments of the present invention and with respect to formula (I), subscript t is 0; subscript v is 4; and X is a carbosilane represented by the following formula (2a): [ka] With respect to formula (2a), q is 0 to 3 (e.g., 1 to 3); w is, independently for each q, 1 to 3; 20 is independently selected for each q from methyl, ethyl, or phenyl; y is 1 to 3; and each R 21 is independently selected from methyl, ethyl or phenyl. Further, with respect to formula (2a), each of the four single bonds has unsatisfied valences extending from the two Si atoms and independently represents a single bond to a -L-[mesogenic] group (or moiety) of formula (I).

[0086] In some embodiments of the present invention and with respect to formula (I), subscript t is 0; subscript v is 4; and X is represented by formula (3): [ka]

[0087] In some embodiments of the present invention and with respect to formula (I), subscript t is 0; subscript v is 3; and X is represented by formula (4): [ka]

[0088] In some embodiments of the present invention and with respect to formula (I), subscript t is 0; subscript v is 4; and X is represented by formula (5): [ka]

[0089] With respect to formula (I) and according to some embodiments, the polyvalent linking group X is Si; t is 1; and R4 is -(S1) d -P, where S1, d, and P are each as defined for formula (II); and the subscript v is 3. Further, with respect to formula (I) and according to some embodiments, the polyvalent linking group X is Si; t is 1; R4 is -(S1) d and R4-X is represented by the following formula (6): [ka]

[0090] With respect to formula (I) and according to some embodiments, the polyvalent linking group X is P (i.e., and subscript v is 3. In further embodiments of the present invention and with respect to formula (I), subscript t is 1; R4=O; subscript v is 3; X is P (i.e., phosphorus); and R4-X is represented by the following formula (7): [ka]

[0091] In some embodiments of the present invention, t in formula (I) is 0, 1, or 2. In some further embodiments, t is 2 and the two R groups together define a double-bonded oxygen group (i.e., =O).

[0092] With respect to formula (I), the bond between X and R4 is depicted as a single bond, but in some embodiments, it may be a double bond, depending on the R4 selected. For purposes of illustration, when R4 is selected from =O, the bond between X and R4 is a double bond (=). For purposes of further illustration, when R4 is -(S1) d When selected from -P, the bond between X and R4 is a single bond (-).

[0093] According to some embodiments of the present invention, for at least one mesogen, P in formula (II) is independently in each occurrence selected from acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic acid ester, siloxane, carbosilane, cyano or nitro.

[0094] In some further embodiments of the present invention, each mesogen of Formula (I) is represented, independently for each v, by Formula (IV): [ka]

[0095] With respect to formula (IV) and according to some further embodiments, R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; S2, S3, S4, Q2, Q3, e', f', e, f and g are each independently as defined and described herein above with respect to formula (II).

[0096] According to some embodiments of the present invention, at least one mesogen of formula (I) is represented, independently for each v, by formula (IV):

[0097] In some embodiments of the invention, at least one mesogen of formula (I) is represented by formula (II) for at least one subscript v and for fewer than all subscripts v', independently in each occurrence, where P in formula (II) is selected from acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic acid ester, siloxane, carbosilane, cyano or nitro. According to further such embodiments, at least one subscript v is selected from the group consisting of aryl, methacrylate, trihalomethacrylate, cyanoacrylate, cyanoacrylate, ester, siloxane, carbosilane, cyano, and nitro. For letter v and for any fewer than all subscript v', at least one mesogen of formula (I) is represented, independently in each occurrence, by formula (IV) above, wherein R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; S2, S3, S4, Q2, Q3, e', f', e and f are each independently as defined and described herein above for formula (II).

[0098] By way of non-limiting illustration, a terminal R-substituted divalent 1,4-cyclohexyl moiety of formula (IV) [ka] is -Q1-(S1) of formula (II) d-P terminal moiety, where Q1 is a divalent 1,4-cyclohexyl group; subscript d is 0; and P is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy (designated as R).

[0099] In some additional embodiments of the mesogen-containing compounds of the present invention and with reference to formula (I), for each subscript v, each mesogen is the same.

[0100] With respect to formula (I) and according to some embodiments, each mesogen comprises, for each subscript v, at least four cyclic groups.

[0101] With respect to formula (I) and according to some embodiments, each linking group -L-, for each subscript v, independently has at least 25 bonds, or at least 30 bonds, e.g., 25 to 200 bonds (or 30 to 200 bonds, or 35 to 200 bonds); or 25 to 150 bonds (or 30 to 150 bonds, or 35 to 150 bonds); or 25 to 100 bonds (or 30 to 100 bonds, or 35 to 100 bonds); or 25 to 80 bonds (or or 25 to 75 bonds (or 30 to 75 bonds, or 35 to 75 bonds); or 25 to 70 bonds (or 30 to 70 bonds, or 35 to 70 bonds); or 25 to 60 bonds (or 30 to 60 bonds, or 35 to 60 bonds); or 25 to 45 bonds (or 30 to 45 bonds, or 35 to 45 bonds), each bond being independently selected from a single bond, a double bond or a triple bond.

[0102] Further, with regard to formula (I) and according to some embodiments, each linking group -L-, for each subscript v, does not contain mesogenic character in each instance.

[0103] According to some embodiments, and with respect to Formula (I), each linking group -L-, for each subscript v, is independently in each occurrence selected from the following formulae L(1) through L(10), including combinations of two or more thereof: [ka] [ka] [ka]

[0104] For formulas L(1) through L(10), each t is, independently for each occurrence, 1 to 20.

[0105] The present invention relates to liquid crystal compositions comprising the mesogen-containing compounds of the present invention, such as those described with respect to formula (I). In some embodiments, the liquid crystal compositions according to the present invention can further comprise at least one of a photochromic compound, a dichroic compound, and / or a photochromic-dichroic compound, in addition to at least one compound represented by formula I.

[0106] Classes of photochromic compounds that can be present in the liquid crystal compositions of the present invention include, but are not limited to, indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, diarylalkenylethenes, and mixtures thereof.

[0107] The photochromic-dichroic compound that can be present in the liquid crystal composition of the present invention typically comprises at least one photochromic moiety and at least one covalently bonded extension group, and the extension group comprises at least one mesogenic segment.In some embodiments, each photochromic moiety of the photochromic-dichroic compound is selected from indeno-fused naphthopyran, naphtho[1,2-b]pyran, naphtho[2,1-b]pyran, spirofluoroeno[1,2-b]pyran, phenanthropyran, quinolinopyran, fluoroanthenopyran, spiropyran, benzoxazine, naphthoxazine, spiro(indoline)naphthoxazine, spiro(indoline)pyridobenzoxazine, spiro(indoline)fluoranthenoxazine, spiro(indoline)quinoxazine, fulgide, fulgimide, diarylethene, diarylalkylethene, diarylalkenylethene and combinations thereof.

[0108] Classes and examples of extender groups of photochromic-dichroic compounds that can be included in the liquid crystal composition of the present invention include, but are not limited to, those described in columns 37 to 51 of U.S. Pat. No. 9,334,439 B2, the disclosure of which is incorporated herein by reference.

[0109] The liquid crystal composition according to the present invention can optionally further comprise at least one additive. Examples of such optional additives include, but are not limited to, liquid crystal materials, liquid crystal property control additives, nonlinear optical materials, dyes (e.g., static dyes), dichroic dyes, blue light blocking (or filtering) agents, alignment promoters, speed enhancers, photoinitiators, thermal initiators, surfactants, polymerization inhibitors, solvents, light stabilizers, thermal stabilizers, release agents, rheology modifiers, gelling agents, leveling agents, free radical scavengers, coupling agents, tilt control agents, block or nonblock polymer-based materials, and / or adhesion promoters. Classes and examples of blue light blocking (or filtering) agents include, but are not limited to, those described in U.S. Pat. No. 9,683,102 B2 and U.S. Pat. Appl. Pub. No. 2015 / 0234208 A1, the relevant portions of which are incorporated herein by reference.

[0110] Examples of dichroic dyes that may be included in the liquid crystal composition of the present invention include, but are not limited to, azomethines, indigoids, thioindigoids, merocyanines, indanes, quinophthalone dyes, perylenes, phthaloperines, triphenodioxazines, indoloquinoxalines, imidazo-triazines, tetrazines, azo and (poly)azo dyes, benzoquinones, naphthoquinones, anthroquinones and (poly)anthroquinones, anthropyrimidinones, iodine, iodates, or combinations of two or more thereof.

[0111] According to the present invention there is further provided an optical element comprising a substrate; and a layer on (or above) at least a portion of a surface of the substrate, the layer comprising at least one mesogen-containing compound according to the present invention.

[0112] The substrate of the optical element is an optical substrate in some embodiments, which may include organic materials (such as organic polymers), inorganic materials, or combinations thereof (e.g., composite materials). Examples of substrates that can be included in the optical element of the present invention include, but are not limited to, those described in U.S. Patent No. 8,628,685 B2, column 35, line 5 to column 36, line 57, the disclosure of which is incorporated herein by reference.

[0113] The layer disposed on the substrate of the optical element of the present invention may, in some embodiments, include an organic matrix, such as an organic polymer matrix, which may be a cured (or crosslinked) organic matrix or a thermoplastic organic matrix. Thus, each layer of the optical element of the present invention may be selected from a cured (or crosslinked) layer and a thermoplastic layer. The organic matrix of each layer of the optical element of the present invention may include bonds such as, but not limited to, ether bonds; carboxylic acid ester bonds; urethane bonds; amide bonds; urea bonds; carbonate bonds; bonds formed from radical polymerization of radically polymerizable ethylenically unsaturated groups, such as, but not limited to, vinyl groups, allyl groups, and / or (meth)acrylate groups; and combinations of two or more of these.

[0114] Each layer of the optical element of the present invention can be formed by art-recognized methods, including, but not limited to, lamination and coating methods. Coating methods include, but are not limited to, spray coating, spin coating, curtain coating, dip coating, microjet coating (such as inkjet coating), in-mold coating, and combinations thereof. Lamination methods include, but are not limited to, extrusion lamination (such as directly onto a substrate), in-mold lamination (where a laminate is placed into a mold against which a substrate is formed within the mold), thermal lamination (where a laminate is heat fused onto a substrate), adhesive lamination (where a laminate is adhered onto a substrate by an intervening adhesive layer), and combinations thereof. Examples include:

[0115] In some embodiments of the present invention, the optical element further comprises an alignment layer interposed between the substrate and the layer (comprising the mesogen-containing compound of the present invention), the alignment layer being at least partially alignable by exposure to at least one of a magnetic field, an electric field, linearly polarized radiation, a shear force, or a combination of two or more thereof. Classes and examples of materials that can be used as or to form the alignment layer include, but are not limited to, the alignment mechanisms, alignment materials, alignment media, and alignment mechanisms described in U.S. Pat. No. 8,926,091 B2 at column 5, line 5 to column 6, line 4; column 7, line 56 to column 24, line 36; and in the Examples, the disclosures of which are incorporated herein by reference.

[0116] In some embodiments, the optical element of the present invention may include one or more additional layers, such as, but not limited to, a primer layer, an anti-reflection layer, a protective layer, a hard coat layer, and a polarizing layer. Classifications and examples of such additional optional layers are described in U.S. Pat. No. 8,828,284 B2, column 20, line 30 to column 21, line 38, the disclosure of which is incorporated herein by reference.

[0117] In some embodiments, the optical element of the present invention is selected from an ophthalmic element, a display element, a window, a mirror, and a liquid crystal cell element.

[0118] In some further embodiments, the ophthalmic elements of the present invention are selected from corrective lenses, non-corrective lenses, contact lenses, intraocular lenses, magnifying lenses, protective lenses, and visors.

[0119] The present invention may be further characterized by one or more of the following non-limiting clauses.

[0120] Clause 1: Formula (I): [ka] (In the formula, v is 3 or 4; t is 0 or 1; (A) each mesogen is independently represented by the following formula (II) for each v: [ka] With respect to formula (II), P is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, acrylamide, methacrylamide, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic ester, siloxane, carbosilane, cyano, or nitro; S1, S2, S3 and S4 are independently selected for each occurrence from a spacer unit selected from -CH2-; -O-; -C(O)-; -N=N-; -CH=CH-; -C≡C-; -CH=N-; -CF2-; or -NH-, provided that when two spacer units containing heteroatoms are bonded together, the spacer unit is not required to bond the heteroatoms directly to each other. provided that they are combined in such a way that they are not merged; d is between 0 and 20; e, f and g are, independently for each occurrence, 0 to 3; Q1, Q2 and Q3, for each occurrence, are independently a divalent radical selected from the group consisting of an unsubstituted or substituted cycloaliphatic group; an unsubstituted or substituted heterocycloaliphatic group; an unsubstituted or substituted aryl; and an unsubstituted or substituted heteroaryl; each cycloaliphatic group substituent, each heterocycloaliphatic group substituent, each aryl substituent and each heteroaryl substituent are independently in each occurrence -(S1) d -P, where S1, d and P are each as defined for formula (II); and e' and f', independently for each occurrence, are 0 to 6, provided that the sum of e' and f' is at least 2; (B) each -L-, independently for each v, is represented by the following formula (III): [ka] wherein: (i) y is 0 to 30; (ii) each A is, independently for each y, a divalent group selected from the group consisting of a single bond, an aliphatic group, and a haloaliphatic group; (iii) each B, for each y, is independently: -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R a is independently selected from methyl, ethyl, or phenyl, and each R3, for each n, is independently selected from methyl, ethyl, or phenyl; [ka] (wherein t' is 1 to 4, u' is, independently for each t', 1 to 5, and each R 16is independently selected for each t′ from methyl, ethyl, or phenyl, and each R 17 is independently selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each 5 is independently selected from methyl, ethyl, or phenyl; and (iv) E is a divalent radical selected from the group consisting of an aliphatic group and a haloaliphatic group; (C) X is Si; N; Ge; P; a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms; an unsubstituted or substituted cyclic aliphatic group; an unsubstituted or a substituted heterocyclic aliphatic group; an unsubstituted or substituted aryl group; and an unsubstituted or substituted heteroaryl group; each of the aliphatic group substituents, each of the cyclic aliphatic group substituents, each of the heterocyclic aliphatic group substituents, each of the aryl group substituents, and each of the heteroaryl group substituents are independently in each occurrence -(S1) d -P, where S1, d and P are each as defined for formula (II); and (D) R4 is -(S1) d -P (wherein S1, d and P are each as defined for formula (II)); =O; and unsubstituted or substituted phenyl groups (wherein each phenyl substituent is independently -(S1) d -P, where S1, d and P are each as defined for formula (II). is selected from the group consisting of provided that at least one mesogen contains at least four cyclic groups; and each -L- independently contains an average chain length of at least 15 bonds, and further provided that at least one -L- contains an average chain length of at least 25 bonds. The mesogen-containing compound is represented by:

[0121] Clause 2: independently for each mesogen and independently for each formula (II), Q1, Q2 and Q3 are, independently for each occurrence, a divalent radical selected from the group consisting of unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; unsubstituted or substituted naphthyl; and unsubstituted or substituted triptycenyl, each cycloalkyl substituent, each phenyl substituent, each naphthyl substituent and each triptycenyl substituent are, independently in each occurrence, -(S1) d -P, where S1, d and P are each as defined for formula (II); and X is a polyvalent group selected from the group consisting of Si; a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; and an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms, the substituents of each aliphatic group being independently -(S1) d -P, wherein S1, d and P are each as defined for formula (II).

[0122] Clause 3: independently for each mesogen and independently for each formula (II), Q1, Q2 and Q3 are, independently for each occurrence, a divalent radical selected from the group consisting of unsubstituted or substituted 1,4-cyclohexyl; unsubstituted or substituted 1,4-phenyl; unsubstituted or substituted 1,5-naphthyl; unsubstituted or substituted 2,6-naphthyl; and unsubstituted or substituted 1,8-naphthyl, wherein each 1,4-cycloalkyl substituent, each 1,4-phenyl substituent, each 1,5-naphthyl substituent, each 2,6-naphthyl substituent and each 1,8-naphthyl substituent is, independently in each occurrence, -(S1) d -P, where S1, d and P are each as defined for formula (II); and X is Si; unsubstituted or substituted C1-C 10 Alkyl (where each of C1 to C 10 The alkyl substituents are independently -(S1)d -P, where S1, d and P are each as defined for formula (II); [ka] (wherein, for formula (1), each R6 is independently selected from methyl, ethyl, or phenyl). and the following formula (2): [ka] wherein for formula (2), R7 is a divalent aliphatic group having 1 to 5 carbon atoms, and each R8 is independently selected from methyl, ethyl, or phenyl. 3. The mesogen-containing compound according to claim 1 or 2, wherein R is a polyvalent group selected from the group consisting of:

[0123] Clause 4: independently for each mesogen and independently for each formula (II), P is selected from hydrogen, alkyl, alkoxy, acrylate, or methacrylate; With respect to formula (III), (i) y is 1 to 30; (ii) each A is, independently for each y, a divalent group selected from the group consisting of alkyl and haloalkyl; (iii) each B, for each y, is independently: -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R ais independently methyl, ethyl, or phenyl, and each R3, for each n, is independently selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each R5 is independently selected from methyl, ethyl, or phenyl; and (iv) The mesogen-containing compound according to any one of clauses 1 to 3, wherein E is a divalent group selected from the group consisting of alkyl groups and haloalkyl groups.

[0124] Clause 5: A mesogen-containing compound according to any one of clauses 1 to 3, wherein for at least one mesogen, P in formula (II) is independently selected in each occurrence from acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic acid ester, siloxane, carbosilane, cyano or nitro.

[0125] Clause 6: The at least one mesogen is, independently for each v, represented by the following formula (IV): [ka] wherein R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy; and S2, S3, S4, Q2, Q3, e', f', e, f and g are each independently as defined for formula (II). 6. The mesogen-containing compound according to any one of clauses 1 to 3 or 5, represented by:

[0126] Clause 7: Each mesogen, independently for each v, has the following formula (IV): [ka] wherein R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy; and S2, S3, S4, Q2, Q3, e', f', e, f and g are each independently as defined for formula (II). 7. The mesogen-containing compound according to any one of clauses 1 to 3 or 6, represented by:

[0127] Clause 8: at least one mesogen is represented, independently in each occurrence, by formula (II) for at least one v and for fewer than all v', P in formula (II) is selected from acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic acid ester, siloxane, carbosilane, cyano, or nitro; and The at least one mesogen may, for at least one v and for fewer than all v', independently in each occurrence, be represented by the following formula (IV): [ka] wherein R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy; and S2, S3, S4, Q2, Q3, e', f', e, f and g are each independently as defined for formula (II). 7. The mesogen-containing compound according to any one of clauses 1 to 3, 5 or 6, represented by:

[0128] Clause 9: The siloxane selected as P in formula (II) is represented by the following formula (A): [ka] (For Formula (A), n' is 1 to 4; independently for each n', each R 13 is independently selected from methyl, ethyl, or phenyl; and each R 14 are independently selected from methyl, ethyl, or phenyl. 7. The mesogen-containing compound according to any one of clauses 1 to 3, 5 or 6, represented by:

[0129] Clause 10: The carbosilane selected as P in formula (II) is a carbosilane represented by the following formula (B): [ka] (For Formula (B), t' is 1 to 4; u is, independently for each t', 1 to 5; each R 16 is independently selected for each t' from methyl, ethyl, or phenyl; and each R 17 is selected from methyl, ethyl or phenyl 10. The mesogen-containing compound according to any one of clauses 1 to 3, 5, 6, 8 or 9, represented by:

[0130] Clause 11: For formula (I), t is 0, v is 3, and X is a group represented by the following formula (C): [ka] (For formula (C), each R9 is independently methyl, ethyl, or phenyl. 11. The mesogen-containing compound according to any one of clauses 1, 2 or 4-10, which is a trivalent cyclotrisiloxane represented by:

[0131] Clause 12: For formula (I), t is 0, v is 4, and X is a group represented by the following formula (D): [ka] (For formula (D), each R 10 are independently methyl, ethyl or phenyl. 11. The mesogen-containing compound according to any one of clauses 1, 2 or 4-10, which is a tetravalent cyclotetrasiloxane represented by:

[0132] Clause 13: For formula (I), t is 0, v is 4, and X is a group represented by the following formula (1a): [ka] (In formula (1a), d' is 0 to 3; each R 18 is independently selected for each d' from methyl, ethyl, or phenyl; and each R 19 are independently selected from methyl, ethyl, or phenyl. 11. The mesogen-containing compound according to any one of clauses 1, 2 or 4-10, which is a tetravalent siloxane represented by:

[0133] Clause 14: For formula (I), t is 0, v is 4, and X is a group represented by the following formula (2a): [ka] (For formula (2a), q is 0 to 3 (e.g., 1 to 3); w is, independently for each q, 1 to 3; 20 is independently selected for each q from methyl, ethyl, or phenyl; y is 1 to 3; and each R 21 are independently selected from methyl, ethyl, or phenyl. 11. The mesogen-containing compound according to any one of clauses 1, 2 or 4-10, which is a tetravalent carbosilane represented by:

[0134] Clause 15: The mesogen-containing compound of any one of clauses 1 to 14, wherein for each v, each mesogen is the same.

[0135] Clause 16: The mesogen-containing compound of any one of clauses 1 to 15, wherein each -L-, independently for each v, contains an average chain length of at least 25 bonds or at least 30 bonds.

[0136] Clause 17: The mesogen-containing compound of any one of clauses 1 to 16, wherein each -L-, independently for each v, comprises an average chain length of from 25 to 200 bonds, or from 30 to 150 bonds, or from 35 to 100 bonds.

[0137] Clause 18: The mesogen-containing compound of any one of clauses 1 to 17, wherein each -L- is, independently for each v, selected from formulas L(1) to L(10) as described hereinabove, including combinations of any two thereof.

[0138] Item 19: A liquid crystal composition comprising the mesogen-containing compound according to any one of items 1 to 18.

[0139] Clause 20: The liquid crystal composition of clause 19, further comprising at least one of a photochromic compound, a dichroic compound, or a photochromic-dichroic compound.

[0140] Clause 21: The photochromic-dichroic compound comprises at least one photochromic moiety, and the photochromic compound and each photochromic moiety of the photochromic-dichroic compound are independently selected from indeno-fused naphthopyrans, naphtho[1,2-b]pyrans, naphtho[2,1-b]pyrans, spirofluoroeno[1,2-b]pyrans, phenanthropyrans, quinolinopyrans, fluoroanthenopyrans, spiropyrans, benzoxazines, naphthoxazines, spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines, spiro(indoline)fluoranthenoxazines, spiro(indoline)quinoxazines, fulgides, fulgimides, diarylethenes, diarylalkylethenes, diarylalkenylethenes, and mixtures thereof. The liquid crystal composition of clause 20.

[0141] Clause 22: Substrate; a layer on at least a portion of a surface of said substrate, said layer comprising at least one mesogen-containing compound according to any one of claims 1 to 18; An optical element comprising:

[0142] Clause 23: The optical element described in Clause 22, further comprising an alignment layer interposed between the substrate and the layer, the alignment layer being at least partially alignable by exposure to at least one of a magnetic field, an electric field, linearly polarized radiation, a shear force or a combination of two or more thereof.

[0143] Clause 24: The optical element described in Clause 23, wherein the optical element is selected from a display element, a window, a mirror, a liquid crystal cell element and an ophthalmic element.

[0144] Clause 25: The optical element described in Clause 24, wherein the ophthalmic element is selected from corrective lenses, non-corrective lenses, contact lenses, intraocular lenses, magnifying lenses, protective lenses and visors.

[0145] The present invention is more particularly described in the following examples, which are intended to be illustrative only, since numerous modifications and variations therein will be apparent to those skilled in the art. EXAMPLES

[0146] In Part 1 of the following examples, the intermediate mesogen-containing segment [ka] Part 1 describes the preparation of intermediate central segments or moieties each comprising a multivalent non-mesogenic core X to which v linking groups -L- and t R4 groups are attached. Part 2 describes the preparation of intermediate central segments or moieties each comprising a multivalent non-mesogenic core X to which v linking groups -L- and t R4 groups are attached. Part 3 describes the preparation of mesogen-containing compounds according to the invention and comparative mesogen-containing compounds. Part 4 describes the preparation of liquid crystal coating formulations. Part 5 describes the production of coated substrates (test strips). Part 6 describes the photochromic performance testing of the coated substrates of Part 5 and the test results.

[0147] Part 1 The preparation of the intermediate mesogen-containing segments S1-S10 is illustrated as follows: Representative structures of the intermediate mesogen-containing segments S1-S10 are shown in Table 1.

[0148] Segment S1 Segment S1 was prepared according to Example 1, step 8 of US Patent Application Publication No. 2017 / 0275534 A1.

[0149] Segment S2 Toluene (1.5 L) and triethylamine ("Et3N", 15.0 mL) were added to a single-neck round-bottom flask containing segment S1 (400 g) and succinic anhydride (74.0 g). The suspension was heated to 80° C. and stirred for 5 h. The reaction mixture was poured into hot ethyl acetate ("EtOAc", 1.5 L, 65° C.) with stirring, and the flask was then rinsed with tetrahydrofuran ("THF", 100 mL). The resulting solution was allowed to cool to room temperature and crystallized overnight to give 410 g of product (88% yield). 1 H NMR showed the product to have a structure consistent with 4-oxo-4-((8-(4-((4-((4'-pentyl-[1,1'-bi(cyclohexane))]-4-carbonyl))oxy)phenoxy)carbonyl)phenoxy)octyl)oxy)butanoic acid.

[0150] Segment S3 Segment S1 (25.0 g) and ε-caprolactone (18.5 g) were suspended in dichloromethane ("DCM", 100 mL) and then diphenyl phosphate ("DPP", 2.52 g) was added in one portion. After stirring at room temperature for 6 h, the crude reaction solution was washed with HCl (1 M, 2×100 mL), NaOH (5% wt / vol aqueous solution, 2×100 mL) and saturated brine (2×50 mL). The organic phase was then dried over MgSO4 and then filtered through Celite. The filtrate was passed through a plug of silica gel topped with Celite using 10% EtOAc in DCM as the eluent. The material was concentrated to an off-white waxy solid and then dissolved in DCM (1 mL / g). The solution was filtered through Celite to remove insoluble material. The solution was concentrated to 50 mL and then slowly added to cold hexane (0° C., 430 mL). Yield: 37.18g.

[0151] Segment S4 Segment S4 is the 3-chloropropan-1-ol from step 1 Prepared according to the procedure of steps 1 to 6 of Example 2 of U.S. Pat. No. 8,349,210 B2, except that in step 3, 6-chlorohexan-1-ol was replaced with 8-chlorooctan-1-ol, and in step 4, 6-chlorohexan-1-ol was replaced with 8-chlorooctan-1-ol.

[0152] Segment S5 Segment S5 was prepared using the procedure for segment S2, replacing segment S1 with an equimolar amount of segment S4.

[0153] Segment S6 Segment S6 was prepared using the procedure for segment S3, except that segment S4 was used instead of segment S1 and 8 molar equivalents of ε-caprolactone were used.

[0154] Segment S7 Segment S7 was prepared using the procedures of steps 1 and 2 of Example 7 of US Patent Application Publication No. 2017 / 0275534 A1.

[0155] Segment S8 Segment S8 was prepared according to Example 8, step 2 of US Patent Application Publication No. 2012 / 0002141 A1.

[0156] Segment S9 To a solution of segment S2 (21.6 g), bis(hydroxypropyl)tetramethyldisiloxane (15.0 g), and 2-(dimethylamino)pyridinium p-toluenesulfonate ("DPTS", 0.9 g) in DCM was added N,N'-dicyclohexylcarbodiimide ("DCC", 7.4 g) over 5 hours. 1,3-dicyclohexylurea ("DCU") was removed and the material was chromatographed using DCM-EtOAC (50:1 to 10:1) to give the desired product. Yield: 14.0 g.

[0157] Segment S10 The synthesis of segment S10 was carried out following a similar procedure to segment S9, using the following amounts: segment S2 (21.6 g), 1H,1H,11H,11H-perfluoro-3,6,9-trioxaundecane-1,11-diol (24.6 g), DPTS (0.9 g), DCM and DCC (7.4 g). Yield: 22.0 g.

[0158] [Table 1]

[0159] Part 2 Below, the preparation of intermediate central segments (or moieties) C1-C4 is described, each of which comprises a multivalent non-mesogenic core X to which v linking groups -L- and t R4 groups are attached. Representative structures of intermediate central segments C1-C4 are shown in Table 2.

[0160] Segment C1 2-Ethyl-2-(hydroxymethyl)-1,3-propanediol (7.42 g) and ε-caprolactone (75.9 g) were placed in a nitrogen purged flask and heated to 150° C. until homogeneous, then tin(II) 2-ethylhexanoate (0.83 g) was added. The resulting mixture was stirred at 150° C. under nitrogen for 24 hours. The cooled reaction mixture was stirred with hexane (300 mL) and then decanted. This process was repeated three times to obtain a viscous liquid, which was dried under vacuum. Yield: 84 g.

[0161] Segment C2 A solution of segment C1 (43.0 g), succinic anhydride (8.8 g), EtN (5 mL), and toluene (200 mL) was heated at 90 °C for 6 h. The solvent was removed under reduced pressure. The resulting solid was used without further purification.

[0162] Segment C3 Step 1: Step 1 was carried out following a similar procedure as in segment C1 using the following amounts: pentaerythritol (7.54 g), ε-caprolactone (50.6 g), tin(II) 2-ethylhexanoate (1.0 mL). Yield: 58.0 g.

[0163] Step 2: The same reaction conditions as described for Segment S2 above were applied to the product from step 1 above to give Segment C3, except that the product was purified in a similar manner as described for Segment C1 above. Yield: 80.0 g.

[0164] Segment C4 The synthesis of segment C4 was carried out following a similar procedure to segment S2 using the following amounts: pentaerythritol (5.0 g), succinic anhydride (18.3 g), Et3N (5.0 mL), toluene (100 mL). Yield: 15.0 g.

[0165] [Table 2]

[0166] Part 3 The preparation of mesogen-containing compounds according to the present invention (Examples 1-4, 6, 9, 10, 12 and 14) and comparative mesogen-containing compounds (Comparative Examples / CE5, 7, 8, 11, 13 and 15) is described below. Representative structures of mesogen-containing compounds according to the present invention and comparative mesogen-containing compounds are shown in Table 8.

[0167] Example 1 Step 1: 2-(hydroxymethyl)-2-methylpropane-1,3 in acetone (500 mL) A flask containing -diol (100.0 g), 2,2-dimethoxypropane (130 g), and 4-toluenesulfonic acid ("TsOH", 4.0 g) was stirred under nitrogen at room temperature for 24 hours. Aq. NaHCO3 (100 mL, 4.3 M) was added. The solution was concentrated, dissolved in 500 mL of DCM, and washed with water. The organic layer was passed through a short silica plug and concentrated to give (2,2,5-trimethyl-1,3-dioxan-5-yl)methanol.

[0168] Step 2: To a solution of segment S5 (14.64 g), the product from step 1 above (3.52 g), and 4-dimethylaminopyridine (DMAP) (0.48 g) in DCM (100 mL) was added DCC (4.94 g). The resulting mixture was stirred at room temperature for several hours. DCU was removed by filtration, and the filtrate was purified by column chromatography.

[0169] Step 3: The product from step 2 above was dissolved in DCM-methanol (MeOH) (1:1, 200 mL) and TsOH (0.8 g) was added. After stirring overnight, the solution was washed with NaHCO3 and brine. This material was chromatographed (eluent was 17-66% EtOAc in DCM).

[0170] Step 4: To a solution of the product from step 3 above (4.4 g) and ε-caprolactone (4.81 g) in DCM (100 mL) was added DPP (0.66 g). The solution was stirred at room temperature for 8 h. DMAP (0.32 g), segment S2 (8.36 g) and DCC (2.61 g) were added and the reaction was allowed to stir overnight. DCU was removed by filtration. The filtrate was washed twice with HCl (1 M), twice with NaOH (5% wt / vol.) and twice with saturated brine, followed by purification via column chromatography (eluent gradient from DCM to DCM-EtOAc (5:1)).

[0171] Example 2 Step 1: Step 1 was carried out using a procedure similar to that of step 1 of Example 1, except that 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid was used instead of 2-(hydroxymethyl)-2-methylpropane-1,3 diol and the crude product was washed with ethanolic ammonia instead of aqueous NaHCO. Yield: 35.0 g.

[0172] Step 2: The product from step 1 above (4.53 g), segment S6 (30.9 g), DPTS (3.12 g) and DCC (5.78 g) were dissolved in DCM (500 mL). After stirring overnight, starting segment S6 was still present. To the product from step 1 above (3.48 g) was further added DCC (4.12 g). After 3 days, the mixture was partially concentrated and the DCU was removed by filtration. The filtrate was washed with water and brine, dried over MgSO4, and passed through a silica gel plug (eluent gradient from DCM to DCM-EtOAc (5:1)). The resulting material was purified by precipitation from EtOAc-MeOH. Yield: 26.5 g.

[0173] Step 3: Step 3 was carried out following a similar procedure to step 3 of example 1 using the following amounts: product from step 2 above (26.5 g), TsOH (0.6 g), DCM-MeOH (1:1, 200 mL). Yield: 16.0 g.

[0174] Step 4: The synthesis of Example 2 was carried out using a procedure similar to that of Step 2 of Example 1 above, using the following amounts: product from Step 3 above (3.09 g), segment S2 (3.17 g), DMAP (0.1 g), DCC (1.0 g) and DCM (100 mL). Yield: 2.5 g, 41%.

[0175] Examples 3, 4 and CE-5 The mesogen-containing compounds of Examples 3, 4 and CE-5 were prepared according to the following general procedure.

[0176] One molar equivalent of trifunctional carboxylic acid (tri-COOH) intermediate central segment (C2), three molar equivalents of alcohol (OH) functional intermediate mesogen-containing segment (S9, S10 or S7), summarized in Table 3 below, and DPTS (0.3 eq) were mixed in enough DCM to dilute approximately 90% by weight. DCC (4.0 eq) was added in one portion and the reaction was stirred at room temperature. DCU was removed and the filtrate was chromatographed using DCM-EtOAc (10:1 to 3:1) as eluent to give the desired product. 1 1 H NMR was used to confirm the structures of all products and the lengths of the oligomers in the purified products.

[0177] [Table 3]

[0178] Examples 6, CE-7 and CE-8 The mesogen-containing compounds of Examples 6, CE-7 and CE-8 were prepared according to the following general procedure.

[0179] One molar equivalent of a trifunctional hydroxyl (tri-OH) intermediate central segment (as indicated), 3.5 molar equivalents of a carboxylic acid (COOH) functional intermediate mesogen-containing segment (S8, S5 or S2), 4-toluenesulfonic acid (0.5 equivalents), and DMAP (0.5 equivalents), as summarized in Table 4 below, were mixed in enough DCM to dilute approximately 90% by weight. DCC (3.25-4.0 equivalents) was added in one portion. After stirring under nitrogen for 24 hours, the DCU precipitate was removed and the material was chromatographed (eluent was DCM / EtOAc). The material was dissolved in EtOAc, filtered through Celite, and then precipitated from MeOH to give the desired product. 1 1 H NMR was used to confirm the structures of all products and the lengths of the oligomers in the purified products.

[0180] [Table 4]

[0181] Example 9 Step 1: Step 1 was carried out according to a similar procedure to Example 14 (described in detail herein) using the following amounts: segment S1 (30.0 g), DPP (6.0 g), ε-caprolactone (27.5 g), DCM (100 mL), 3-(allyloxy)propionic acid (8.0 g), DCC (15.0 g), DMAP (2.95 g). Yield: 50.0 g

[0182] Step 2: A nitrogen purged Schlenk tube was charged with the product of step 2 above (15.0 g), 1,3-diphenyltetrakis(dimethylsiloxy)disiloxane (1.6 g), Karsted catalyst (5 drops, 2% Pt in xylene) and toluene (25 mL). The Schlenk tube was then covered with aluminum foil, sealed with a rubber septum and stirred at room temperature for 6 days. The solvent was removed and the solid was dissolved in DCM before chromatography (eluent was 60% EtOAc in DCM). The waxy solid was dissolved in EtOAc (1 g / 5 mL) and filtered through Celite. A clear solution was precipitated by pouring into cold MeOH (1:5 vol / vol%, 0° C.). The precipitated product was filtered, washed with MeOH and dried under vacuum at room temperature. Yield: 9 g, 51%.

[0183] Examples 10 and CE-11 The mesogen-containing compounds of Examples 10 and CE-11 were prepared according to the following general procedure.

[0184] One molar equivalent of a tetrafunctional carboxylic acid (tetra-COOH) intermediate central segment (as indicated), four molar equivalents of an alcohol (OH) functional intermediate mesogen-containing segment (S9 or S1), summarized in Table 5 below, and DPTS (0.4-1.5 equivalents) were mixed in enough DCM to dilute approximately 90% by weight. DCC (4.5 equivalents) was added in one portion and the reaction was stirred at room temperature. The DCU was removed and the filtrate was chromatographed using DCM-EtOAc (3:1) as eluent or recrystallized from THF / ethanol (2 / 1) to give the desired product. 1 HNMR was used to confirm the structures of all products and the lengths of the oligomers in the purified products.

[0185] [Table 5]

[0186] Examples 12 and CE-13 The mesogen-containing compounds of Examples 12 and CE-13 were prepared according to the following general procedure.

[0187] One molar equivalent of chlorosilane (as indicated) and Et3N (3.5-5 eq.), summarized in Table 6 below, were dissolved in DCM and cooled on ice. A solution of the alcohol (OH)-functional intermediate mesogen-containing segment (S3, 3 eq.; or S6, 4 eq.) in DCM was added slowly over several minutes. The crude reaction solution was washed with water (2×100 mL) and saturated brine (2×50 mL). The organic phase was dried over MgSO4 and then filtered through Celite. The filtrate was passed through a silica gel plug topped with Celite (eluent was 10-20% EtOAc in DCM). The resulting off-white waxy solid was dissolved in DCM (1 mL / g). The solution was filtered through Celite to remove insoluble material and the filtrate was slowly poured into cold hexane (0° C., 100 mL) to precipitate the material. 1 1 H NMR was used to confirm the structures of all products and the lengths of the oligomers in the purified products.

[0188] [Table 6]

[0189] Examples 14 and CE-15 The mesogen-containing compounds of Examples 14 and CE-15 were prepared according to the following general procedure.

[0190] The alcohol (OH) functional intermediate mesogen-containing segment (4.0-4.5 molar equivalents) summarized in Table 7 below was mixed with ε-caprolactone (molar equivalents shown). To this was added DPP (2.0-2.25 equivalents) and the mixture was stirred under nitrogen for 4 hours to form a new alcohol. Next, 1 molar equivalent of the tetracarboxylic acid (tetra-COOH) intermediate middle segment (as shown), DMAP (2.0-2.26 equivalents) and DCC (6 equivalents) were added. After stirring overnight, the DCU was removed and the filtrate was washed twice with NaHCO3, twice with 5% NaOH, twice with 10% HCl and twice with saturated brine. After stirring with MgSO4, the material was passed through a pad of silica gel (eluent was 5-25% EtOAc in DCM). The crude product was redissolved in EtOAc (1 g / 4 mL), filtered through Celite, and precipitated from a mixture of EtOAc and MeOH (1:8 v / v). 1 1 H NMR was used to confirm the structures of all products and the lengths of the oligomers in the purified products.

[0191] [Table 7]

[0192] [Table 8]

[0193] [Table 9]

[0194] [Table 10]

[0195] [Table 11]

[0196] Part 4 The preparation of liquid crystal coating formulations is described as follows: Part 4a describes the preparation of a standard liquid crystal coating formulation; Part 4b describes the preparation of a liquid crystal coating formulation containing a mesogen-containing compound.

[0197] Part 4a. Preparation of standard liquid crystal coating formulations. The ingredients of Charge 1 as listed in Table 9 were placed in a suitable vessel equipped with a stir bar and stirred at room temperature until a homogenous solution was obtained. Charge 2 was then added and the resulting mixture was stirred at 90° C. for 1 hour. The liquid crystal monomer (Charge 3) was then added and the solution was stirred at 90° C. for an additional hour. The temperature of the solution was then reduced to 60° C. and Charge 4 was added to the solution and the mixture was stirred for 30 minutes to obtain the final solution.

[0198] [Table 12]

[0199] Part 4b. Preparation of liquid crystal coating formulations containing mesogen-containing compounds. The liquid crystal coating formulation containing the mesogen-containing compound is (shown in Table 10) to the standard liquid crystal coating formulation described in Part 4a. Mixtures were prepared as summarized in Table 10 below, with each mesogen-containing compound being added to 5.4 parts of the standard liquid crystal coating formulation. The components were combined and stirred at 80°C for 1 hour to obtain a homogeneous solution. The amount added is calculated based on 2.2 mol% of the liquid crystal monomer. Anhydrous magnesium sulfate was then added to the solution, followed by stirring at room temperature for 30 minutes. The magnesium sulfate was then filtered off by centrifugation, and the filtrate was used for spin coating.

[0200] [Table 13]

[0201] Part 5 The preparation of coated substrates (test specimens) using the liquid crystal coating formulation of Part 4b (Table 10) is described as follows.

[0202] The following procedure was used to form coated substrates (test specimens): Each liquid crystal coating formulation described in Part 4b (Table 10) was spin coated onto a CR-39® lens substrate having an alignment layer at a speed of 400 revolutions per minute (rpm) for 6 seconds, followed by 1250 rpm for 6 seconds. Each coated substrate was placed in a 60-75° C. oven for 30 minutes to induce alignment, after which they were heated to 1000° C. for 30 minutes at 0.388 Watts / cm. 2 of UVA and 0.165 watts / cm 2 and 7.386 Joules / cm 2 of UVA and 3.337 Joules / cm 2 The UV dose was measured at 1000 uV in a Belcan tube under nitrogen atmosphere while moving on a conveyor belt at 2 ft / min (61 cm / min). The coating was cured under two ultraviolet lamps in a UV curing oven designed and manufactured by Ionochemical Engineering.

[0203] Part 6 The following describes the photochromic performance testing of the Part 5 coated substrates (test specimens) and the test results, including the absorption ratio and optical response measurements and results.

[0204] The specimens were conditioned in a multi-stage custom-built conditioning unit prior to response testing on an optical bench. First, they were exposed to 365 nm ultraviolet light for 10 minutes at a distance of approximately 10 cm from the electromagnetic radiation source to preactivate the photochromic compounds. The UVA irradiance at the sample was measured to be 7.7 watts per square meter. Next, the specimens were heated to 70°F (21.1°C) and held for 10 minutes. Finally, the heating element was turned off and an F17T8 yellow halogen light was turned on for 30 minutes to bleach or inactivate the photochromic compounds in the specimens. The irradiance from the yellow halogen light at the specimens was measured to be 9.0 Klux. The specimens were then stored in the dark for at least 1 hour prior to testing to allow them to continue to cool and return to their ground state bleached state.

[0205] An optical bench was used to measure the optical properties of the specimens and derive the absorption ratio and photochromic properties. Each specimen was placed on the optical bench with the activation light source positioned at an incidence angle of 30° to 35° to the surface of the test sample. The activation light source used was a xenon arc lamp powered by a Newport / Oriel Model 69911 300 watt power supply, equipped with a UNIBLITZ® VS-25 high-speed computer-controlled shutter that was momentarily closed during data collection to prevent stray light from interfering with the data collection process, a SCHOTT® 3 mm KG-2 heat-absorbing filter to remove short-wavelength radiation, a neutral density filter for intensity attenuation, and a focusing lens for beam collimation. The arc lamp was equipped with a digital exposure controller and sensor (Newport / Oriel Model 68945) to maintain fine adjustment of the output over time.

[0206] A broadband light source for monitoring the response measurements was positioned perpendicular to the surface of the test specimen. A split-end, bifurcated fiber optic cable was used to collect and combine separately filtered light from a 100 watt tungsten halogen lamp (controlled by a LAMBDA® ZUP60-14 constant voltage power supply) to increase the signal at shorter visible wavelengths. The light from one side of the tungsten halogen lamp was filtered with a SCHOTT® KG1 filter to absorb heat and a HOYA® B-440 filter to pass short wavelengths. The other light was either filtered with a SCHOTT® KG1 filter or unfiltered. Light was collected by focusing the light from both sides of the lamp into separate ends of a split-end, bifurcated fiber optic cable, then combined into one light source exiting a single end of the cable. A 4-6 inch (10.2-15.25 cm) light pipe was attached to one end of the cable to ensure proper mixing. The broadband light source was fitted with a UNIBLITZ® VS-25 high-speed computer-controlled shutter that was opened momentarily during data collection.

[0207] Polarization of the light source was achieved by passing light from one end of the cable through a Moxtek, PROFLUX® polarizer held on a computer-driven (analyzer polarizer) motorized rotation stage (Physik Instrumente Model M-061.PD, M660, U651 or equivalent). The monitoring light was set up so that one polarization plane (0°) was perpendicular to the plane of the optical bench table and the second polarization plane (90°) was parallel to the plane of the optical bench table. Specimens were run in air at 23°C ± 0.1°C (this temperature was maintained by a temperature-controlled air cell).

[0208] To orient the specimens made in part 4, a second polarizer was added to the light path (polarizer from OptoSigma, research grade film polarizer such as SPF-50C-32). The second polarizer was set at 90° (+ / - 0.1 degrees) of the first analyzer polarizer. The sample was placed in an air cell in a self-centering holder mounted on a rotation stage (Physik Instrumente models M-061.PD, M660, U651 or equivalent). A laser beam (Coherent-ULN635 diode laser) was directed through the crossed polarizers and the sample. The signal strength of the laser beam was measured by relative counting with a spectrophotometer. The specimen was rotated 120 degrees in 3 degree increments to find the minimum transmitted light intensity of the laser beam. The specimen was then positioned near the minimum transmitted light intensity and then rotated 12 degrees in 0.1 degree increments to locate the minimum transmission to ±0.1 degrees depending on the quality of the sample. The specimen was then finally positioned at the minimum transmission angle. At this point, the specimen was positioned parallel or perpendicular to the polarizer of the Moxtek analyzer. The second polarizer and the diode laser light were removed from the light path. Using this process, the specimens were oriented to ±0.1 degrees before any activation.

[0209] To perform the measurements, each specimen was exposed to approximately 6.7 W / m2 of radiation from an activation light source. 2 The photochromic compounds were activated by exposure to 1000 uA for 15 minutes. Exposure was verified at the beginning of each day using an International Light Research Radiometer (Model ILT950(FC)) equipped with a detector system. Light from a monitoring light source polarized in the 0° polarization plane was then passed through the sample and focused onto a 1 inch (2.54 cm) integrating sphere and transferred to an OCEAN OPTICS® integrating sphere using a single function fiber optic cable. The polarizer was connected to an S2000 spectrophotometer. Spectral information after passing through the sample was collected using OCEAN OPTICS Drivers in combination with appropriate software from Transitions Optical, Ltd. While activating the photochromic material, the position of the polarizer was rotated back and forth to polarize the light from the monitoring light source to a 90° polarization plane and back. Data was collected for approximately 600-1200 seconds at 5 second intervals during activation. For each test, the rotation of the polarizer was adjusted and data was collected in the following order of polarization planes: 0°, 90°, 90°, 0°.

[0210] The absorbance ratio (AR) is the ratio of absorbance measured with 90° polarized light (orientation perpendicular to the analyzer polarizer, minimum transmission) and 0° polarized light (orientation parallel to the analyzer polarizer, maximum transmission).

[0211] The change in optical density (ΔOD) from the bleached (non-activated) state to the darkened (activated) state was determined by checking the initial transmittance and opening the shutter to provide UV light from the xenon lamp to change the specimen from the bleached to the activated state. Data was collected at selected time intervals, the transmittance in the activated state was measured, and the change in optical density was calculated according to the following formula: ΔOD=log(%Tb / %Ta), where %Tb is the percent transmittance in the bleached state and %Ta is the percent transmittance in the activated state, and the logarithm is base 10.

[0212] The fade half-life (T1 / 2) is the time interval (seconds) until the ΔOD of the activated form of the photochromic compound in the test strip reaches half of the ΔOD measured after 15 minutes or after saturation or near saturation, achieved at room temperature after removing the activating light source, e.g., by closing a shutter.

[0213] Photochromic performance test results (absorption ratios and fade half-lives) obtained from representative examples according to the present invention (Examples) and comparative examples (CE) are summarized in Table 11 below.

[0214] [Table 14]

[0215] [Table 15]

[0216] The photochromic performance results, summarized in Table 11, show that the mesogen-containing compounds according to the invention (Mesogens) contain only three cyclic groups, compared to comparative mesogen-containing compounds in which the mesogen group contains only three cyclic groups. It has been shown that the mesogen-containing compounds according to the present invention (wherein each -L-linking group independently has an average chain length of at least 15 bonds and at least one -L-linking group has an average chain length of at least 25 bonds) have desirable solubility properties compared to CE-25 (comprising a comparative mesogen-containing compound CE-8 having three distinct -L-[mesogen] extensions) and CE-30 (comprising a comparative mesogen-containing compound CE-11 having four distinct -L-[mesogen] extensions).

[0217] With further reference to the performance results summarized in Table 11, in all cases the comparative mesogen-containing compounds / formulations did not provide an improvement in the absorption ratio compared to the standard liquid crystal coating formulation alone (CE-16).

[0218] The invention has been described with reference to specific details of specific embodiments thereof. It is not intended that such details be considered limitations on the scope of the invention except insofar as they are included in the appended claims. For example, the present invention provides the following: (Item 1) The following formula (I) [ka] (In the formula, v is 3 or 4; t is 0 or 1; (A) each mesogen is independently represented by the following formula (II) for each v: [ka] With respect to formula (II), P is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, acrylamide, methacrylamide, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic ester, siloxane, carbosilane, cyano, or nitro; S1, S2, S3 and S4 are independently for each occurrence selected from a spacer unit selected from -CH2-; -O-; -C(O)-; -N=N-; -CH=CH-; -C≡C-; -CH=N-; -CF2-; or -NH-, with the proviso that when two spacer units containing heteroatoms are linked together, said spacer units are linked such that the heteroatoms are not directly linked to each other; d is between 0 and 20; e, f and g are, independently for each occurrence, 0 to 3; Q1, Q2 and Q3, for each occurrence, are independently a divalent radical selected from the group consisting of an unsubstituted or substituted cycloaliphatic group; an unsubstituted or substituted heterocycloaliphatic group; an unsubstituted or substituted aryl; and an unsubstituted or substituted heteroaryl; each cycloaliphatic group substituent, each heterocycloaliphatic group substituent, each aryl substituent and each heteroaryl substituent are independently in each occurrence -(S1) d -P, where S1, d and P are each as defined for formula (II); and e' and f', independently for each occurrence, are 0 to 6, provided that the sum of e' and f' is at least 2; (B) each -L-, independently for each v, is represented by the following formula (III): [ka] wherein: (i) y is 0 to 30; (ii) each A is, independently for each y, a divalent group selected from the group consisting of a single bond, an aliphatic group, and a haloaliphatic group; (iii) each B, for each y, is independently: -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R a is independently methyl, ethyl, or phenyl, and each R3 is independently selected for each n from methyl, ethyl, or phenyl. selected); [ka] (wherein t' is 1 to 4, u' is, independently for each t', 1 to 5, and each R 16 is independently selected for each t′ from methyl, ethyl, or phenyl, and each R 17 is independently selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each 5 is independently selected from methyl, ethyl, or phenyl; and (iv) E is a divalent radical selected from the group consisting of an aliphatic group and a haloaliphatic group; (C) X is a polyvalent group selected from the group consisting of Si; N; Ge; P; a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms; an unsubstituted or substituted cyclic aliphatic group; an unsubstituted or substituted heterocyclic aliphatic group; an unsubstituted or substituted aryl group; and an unsubstituted or substituted heteroaryl group; and each of the substituents of the aliphatic group, the substituent of the cyclic aliphatic group, the substituent of the heterocyclic aliphatic group, the substituent of the aryl, and the substituent of the heteroaryl is independently in each occurrence -(S1). d -P, where S1, d and P are each as defined for formula (II); and (D) R4 is -(S1) d -P (wherein S1, d and P are each as defined for formula (II)); =O; and unsubstituted or substituted phenyl groups (wherein each phenyl substituent is independently -(S1) d -P, where S1, d and P are each as defined for formula (II), with the proviso that at least one mesogen comprises at least four cyclic groups; and each -L- independently contains an average chain length of at least 15 bonds, and further provided that at least one -L- contains an average chain length of at least 25 bonds. The mesogen-containing compound is represented by: (Item 2) Independently for each mesogen and independently for each Formula (II): Q1, Q2 and Q3 are, independently for each occurrence, a divalent radical selected from the group consisting of unsubstituted or substituted cycloalkyl; unsubstituted or substituted phenyl; unsubstituted or substituted naphthyl; and unsubstituted or substituted triptycenyl, each cycloalkyl substituent, each phenyl substituent, each naphthyl substituent and each triptycenyl substituent are, independently in each occurrence, -(S1) d-P, where S1, d and P are each as defined for formula (II); and X is a polyvalent group selected from the group consisting of Si; a siloxane having 2 to 6 Si atoms; a carbosilane having 2 to 5 Si atoms and 1 to 5 methylene groups between each pair of Si atoms; and an unsubstituted or substituted aliphatic group having 1 to 10 carbon atoms, the substituents of each aliphatic group being independently -(S1) d -P, wherein S1, d and P are each as defined for formula (II). (Item 3) Independently for each mesogen and independently for each Formula (II): Q1, Q2 and Q3 are independently for each occurrence unsubstituted or substituted 1,4-cyclohexyl; unsubstituted or substituted 1,4-phenyl; unsubstituted or substituted 1,5-naphthyl; unsubstituted or substituted and unsubstituted or substituted 1,8-naphthyl, wherein each 1,4-cycloalkyl substituent, each 1,4-phenyl substituent, each 1,5-naphthyl substituent, each 2,6-naphthyl substituent, and each 1,8-naphthyl substituent is independently, in each occurrence, -(S1) d -P, where S1, d and P are each as defined for formula (II); and X is Si; unsubstituted or substituted C1-C 10 Alkyl (where each of C1 to C 10 The alkyl substituents are independently -(S1) d -P, where S1, d and P are each as defined for formula (II); [ka] wherein for formula (1), each R6 is independently selected from methyl, ethyl, or phenyl; and [ka] (wherein for formula (2), R7 is a divalent aliphatic group having 1 to 5 carbon atoms, and each R8 is independently selected from methyl, ethyl, or phenyl). (Item 4) Independently for each mesogen and independently for each Formula (II): P is selected from hydrogen, alkyl, alkoxy, acrylate, or methacrylate; With respect to formula (III), (i) y is 1 to 30; (ii) each A is, independently for each y, a divalent group selected from the group consisting of alkyl and haloalkyl; (iii) each B, for each y, is independently: -O-; -C(O)O-; -OC(O)O-; -C(O)N(R1)- (wherein R1 is H or alkyl); -NH-C(O)O-; -N(R2)C(O)N(R2)- (wherein each R2 is independently selected from H or alkyl); [ka] (wherein n is 1 to 4, and each R a is independently methyl, ethyl, or phenyl, and each R3, for each n, is independently selected from methyl, ethyl, or phenyl; and -Si(R5)(R5)-, where each R5 is independently selected from methyl, ethyl, or phenyl; and (iv) The mesogen-containing compound according to item 3, wherein E is a divalent group selected from the group consisting of alkyl groups and haloalkyl groups. (Item 5) 2. The mesogen-containing compound according to item 1, wherein for at least one mesogen, P in formula (II) is independently selected in each occurrence from acrylate, methacrylate, trihalomethacrylate, cyanoacrylate, oxirane, hydroxyl, primary amino, carboxylic acid, carboxylic acid ester, siloxane, carbosilane, cyano or nitro. (Item 6) The at least one mesogen may, for at least one v, independently in each occurrence, be represented by the following formula (IV): [ka] wherein R is selected from hydrogen, halogen, alkyl, haloalkyl, alkoxy, or haloalkoxy; and S2, S3, S4, Q2, Q3, e', f', e, f and g are each independently as defined for formula (II). 2. The mesogen-containing compound according to item 1, represented by: (Item 7) 2. The mesogen-containing compound according to item 1, wherein for each v, each mesogen is the same. (Item 8) 2. The mesogen-containing compound according to item 1, wherein each -L-, independently for each v, contains an average chain length of at least 25 bonds. (Item 9) Item 2. A liquid crystal composition comprising the mesogen-containing compound according to item 1. (Item 10) 10. The liquid crystal composition according to item 9, further comprising at least one of a photochromic compound, a dichroic compound, or a photochromic-dichroic compound. (Item 11) The photochromic-dichroic compound includes at least one photochromic moiety, and the photochromic compound and each photochromic moiety of the photochromic-dichroic compound may, independently in each occurrence, be an indeno-fused naphthopyran, naphtho[1,2-b]pyran, naphtho[2,1-b]pyran, spirofluoroeno[1,2-b]pyran, phenanthropyran, quinolinopyran, fluoroanthenopyran, spiropyran, benzoxazine, naphthoxazine, spiro(indoline)naphthoxazine, spiro( 11. The liquid crystal composition according to item 10, wherein the compound is selected from the group consisting of: spiro(indoline)pyridobenzoxazine, spiro(indoline)fluoranthenoxazine, spiro(indoline)quinoxazine, fulgide, fulgimide, diarylethene, diarylalkylethene, diarylalkenylethene or mixtures thereof. (Item 12) A substrate; a layer on at least a portion of the surface of the substrate, the layer comprising a mesogen-containing compound according to item 1; An optical element comprising: (Item 13) Item 13. The optical element according to item 12, further comprising an alignment layer interposed between the substrate and the layer, the alignment layer being at least partially alignable by exposure to at least one of a magnetic field, an electric field, linearly polarized radiation, a shear force, or a combination of two or more thereof. (Item 14) 14. The optical element according to item 13, selected from a display element, a window, a mirror, a liquid crystal cell element or an ophthalmic element. (Item 15) Item 15. The optical element according to item 14, wherein the ophthalmic element is selected from a corrective lens, a non-corrective lens, a contact lens, an intraocular lens, a magnifying lens, a protective lens or a visor.

Claims

[Claim 1] The invention described in the specification.

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