Compound, liquid crystal composition, liquid crystal cell, and liquid crystal display device

Abstract

One embodiment of the present application relates to a compound of chemical formula 1, a liquid crystal composition comprising chemical formula 1, a liquid crystal cell, and a liquid crystal display device. The liquid crystal composition comprising the compound of chemical formula 1 can exhibit excellent solubility in a liquid crystal medium, and the liquid crystal composition comprising the compound can advantageously contribute to a contrast ratio and switching performance that can be obtained in a switchable device.

Description

Compounds, liquid crystal compositions, liquid crystal cells, and liquid crystal display devices

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2025-0023411 filed with the Korean Intellectual Property Office on February 24, 2025, and all contents disclosed in the document of said Korean patent application are incorporated into this specification.

[0002] The present application relates to a compound, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device.

[0003] Liquid crystals are used as dielectrics, particularly in display devices, whereby the optical properties of the material may be affected by the applied voltage. In a guest-host system, the liquid crystal medium comprises one or more dichroic dyes in addition to the liquid crystal. Due to a direct dependence on light absorption by the dye molecules, the transmittance of the dye-doped liquid crystal to light can be controlled when the dye molecules change their alignment with the liquid crystal.

[0004] In addition to use in liquid crystal displays, the above-described type of device is also used as a switching element to control the passage of light or energy. In devices for controlling the passage of energy from an external space to an internal space, a number of different technical solutions have been proposed. In one possible mode for the device, a liquid crystal medium combined with one or more of the aforementioned dichroic dyes can generally be used in the switching layers. By applying voltage, a change in the orientational alignment of the dichroic dye molecules can be achieved in these switching layers. Thus, a change in the transmittance of the switching layer can be obtained due to direction-dependent absorption.

[0005] Research is needed on dichroic dye compounds that offer advantages in terms of device performance and reliability, as well as compositions and media containing them.

[0006] (Prior Art) Korean Patent Publication No. 10-2014-0020064

[0007] The present application aims to provide a compound, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device.

[0008] One embodiment of the present application provides a compound of the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] X is O; S; Se; Te; or CRaRb, and

[0013] Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0014] A1, A2, B1, and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups; or are substituted or unsubstituted divalent heterocyclic groups, or can combine with adjacent groups to form substituted or unsubstituted rings, and

[0015] Z1 and Z2 are equal to or different from each other and are each independently directly coupled; -O-; -S-; C(=O)-; -C(RR')-; -C(F2)O-; -OC(F2)-; -C(=O)O-; -OC(=O)-; -OC(H2)-; -C(H2)O-; -C(R)=C(R')-; -C≡C-; -C(R)=C(R')-C(=O)-; -C(=O)-C(R)=C(R')-; -C(R)=C(R')-C(=O)O-; -OC(=O)-C(R)=C(R')- or -N=N- and,

[0016] Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0017] Rc to Rg are the same or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0018] R3 is -ORh; -SRh; -N(R)(R') or a substituted or unsubstituted carbazole group, and

[0019] Rh is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0020] R and R' are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0021] In addition, another embodiment of the present application provides a liquid crystal composition comprising the above compound and a liquid crystal material.

[0022] In addition, another embodiment of the present application provides a liquid crystal cell comprising a first substrate; a liquid crystal layer; and a second substrate, wherein the liquid crystal layer comprises the liquid crystal composition.

[0023] In addition, another embodiment of the present application provides a liquid crystal display device including the liquid crystal cell.

[0024] When a compound according to one embodiment of the present application is used in a liquid crystal composition, a liquid crystal composition with excellent performance, appearance, stability, and / or reliability can be provided even under demanding operating conditions such as increased temperature or direct and extended sunlight irradiation.

[0025] In addition, the liquid crystal composition containing the above compound can exhibit excellent solubility in a liquid crystal medium.

[0026] In addition, a liquid crystal composition containing the above compound can achieve a meaningful and effective dye concentration within a liquid crystal medium.

[0027] A liquid crystal composition containing the above-mentioned compound can advantageously contribute to the contrast ratio and switching performance obtainable in a switchable device.

[0028] FIG. 1 is a diagram illustrating the structure of a liquid crystal cell according to one embodiment of the present application.

[0029] (Explanation of symbols)

[0030] 10: First substrate

[0031] 20: Liquid crystal layer

[0032] 30: Second substrate

[0033] The present application will be described in more detail below.

[0034] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0035] Examples of substituents in this specification are described below, but are not limited thereto.

[0036] The term "substitution" above means that a hydrogen atom bonded to a carbon or nitrogen atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0037] In this specification, the term “substituted or unsubstituted” means one or more substituents selected from the group consisting of halogen groups; cyano groups; hydroxyl groups; oxygen (=O); amine groups; nitro groups; silyl groups; ester groups; sulfide groups; alkyl groups; haloalkyl groups; alkenyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; aryl groups; and heterocyclic groups, or two or more of the exemplified substituents are connected to a substituent, or have no substituents.

[0038] In this specification, hydrogen includes all of hydrogen; deuterium; and tritium.

[0039] In this specification, the halogen group is fluorine, chlorine, bromine, or iodine.

[0040] In this specification, the amine group may be represented as -NR101R102, where R101 and R102 are each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group. The number of carbon atoms in the amine group is not particularly limited, but is preferably 0 to 30.

[0041] In this specification, the silyl group may be represented as -SiR103R104R105, where R103, R104, and R105 are each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group. Specific examples include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, triphenylsilyl groups, and diphenylsilyl groups.

[0042] In this specification, the ester group is represented as -C(=O)OR106 or -OC(=O)R106, wherein R106 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. The number of carbon atoms in the ester group is not particularly limited, but is preferably 2 to 30.

[0043] In this specification, the sulfide group is denoted as -SR107, wherein R107 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group. The number of carbon atoms in the ester group is not particularly limited, but is preferably 2 to 30.

[0044] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, etc., but are not limited thereto.

[0045] In the present specification, the haloalkyl group is an alkyl group substituted with a halogen group, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include CF3, C2F5, etc., but are not limited thereto.

[0046] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0047] In the present specification, the alkenyl group is a substituent comprising a triple bond between carbon atoms, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10.

[0048] In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, b(cyclohexyl), cycloheptyl, cyclooctyl, etc., but is not limited thereto.

[0049] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 30 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, etc., but is not limited thereto.

[0050] In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0051] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0052] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, terphenyl group, pyrenyl group, fluorenyl group, etc., but is not limited thereto.

[0053] In this specification, the aryl group among the aryloxy groups is the same as the examples of aryl groups described above. Specifically, aryloxy groups include phenoxy groups, 1-biphenyloxy groups, etc., but are not limited thereto.

[0054] In the present specification, the heterocyclic group comprises one or more atoms that are not carbon, i.e., heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, S, etc. The number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms is 2 to 30, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group comprises a heterocycloalkyl group and a heteroaryl group, and the heterocycloalkyl group and the heteroaryl group may condense with additional rings such as cycloalkyl and aryl.

[0055] The above heterocycloalkyl group is one in which one or more carbon atoms of a cycloalkyl group are substituted with heteroatoms, examples of which include pyrrolidine, piperidine, oxirane, and oxetane groups, but are not limited thereto, and examples of heterocycloalkyl groups in which additional rings are condensed include indolin and tetrahydroquinoline groups, but are not limited thereto.

[0056] The above heteroaryl group is one in which one or more carbon atoms of an aryl group are substituted with heteroatoms, examples of which include, but are not limited to, thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, pyridine groups, pyrimidine groups, triazine groups, quinoline groups, indole groups, carbazole groups, selenophene groups, dihydrothienodioxine groups, thienopyrrole groups, thienothiazole groups, thienothiophene groups, benzodithiophene groups, etc.

[0057] In this specification, the alkyl carbonyl group is represented as -C(=O)R108, where R108 is an alkyl group, and the description of the alkyl group described above may apply.

[0058] In this specification, the alkoxycarbonyl group is represented as -C(=O)R109, where R109 is an alkoxy group, and the description of the alkoxy group described above may apply.

[0059] In this specification, the alkyl carbonyloxy group is represented as -OC(=O)R110, where R110 is an alkyl group, and the description of the alkyl group described above may apply.

[0060] In this specification, the alkoxycarbonyloxy group is represented as -OC(=O)R111, where R111 is an alkoxy group, and the description of the alkoxy group described above may apply.

[0061] In this specification, the examples of the aforementioned aryl group or heteroaryl group apply, except that the divalent aryl group or divalent heteroaryl group is a divalent group.

[0062] In the present specification, the ring comprises a hydrocarbon ring, a heteroring, or a condensed ring thereof, and specifically comprises an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heteroring, an aromatic heteroring, or a condensed ring thereof.

[0063] Except that the aliphatic hydrocarbon ring and the aromatic hydrocarbon ring are not monovalent, the examples of the aforementioned cycloalkyl group and aryl group apply.

[0064] The examples of the aforementioned heterocyclic rings apply to the aliphatic heterocyclic rings and aromatic heterocyclic rings, except that each is not monovalent.

[0065] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as adjacent groups.

[0066] In this specification, Cn (where n is an integer of 1 or more) means the number of carbon atoms. For example, it means 1 to 60 carbon atoms in C1 to C60.

[0067] dichroic dye compounds

[0068] One embodiment of the present application provides a compound of the following chemical formula 1.

[0069] [Chemical Formula 1]

[0070]

[0071] In the above chemical formula 1, the definition of each substituent is as described above.

[0072] The compound of the present application is characterized by being represented by the above chemical formula 1, specifically comprising thiadiazoloquinoxaline in the compound core portion, and -ORh; -SRh; -N(R)(R') at the terminal R3 or includes substituted or unsubstituted carbazole groups and has a structure of A1(A2)-Z1(Z2)-B1(B2)-Q1(Q2) on both sides of thiadiazoloquinoxaline.

[0073] With such structural features, it is possible to synthesize a dichroic dye with a high absorption coefficient, thereby reducing the amount of dichroic dye used. Additionally, by forming a conjugation system centered on the core structure, compatibility and reliability in the liquid crystal structure can be enhanced, while the dichroic ratio can be increased, thus providing advantages in terms of performance, appearance, stability, and reliability even when used under demanding conditions.

[0074] Specifically, regarding R3 of the above structure, -ORh; -SRh; -N(R)(R') Alternatively, introducing substituted or unsubstituted carbazole groups has the effect of increasing light resistance stability.

[0075] In addition, arylene groups or divalent heterocyclic groups are formed on both or one side of the core structure as A1 and A2, thereby acting as electron donors, which maximizes the ability to sufficiently transfer electrons to the electron acceptor, which is the core structure.

[0076] Z1-B1 and Z2-B2, which are structures connected to the above A1 and A2, are aromatic linkers, and through appropriate linkers, the degree of formation of a conjugated system centered on the core structure can be controlled, thereby determining the absorption wavelength of the dichroic dye and controlling the liquid crystal solubility and compatibility.

[0077] The compound of Chemical Formula 1 above is described.

[0078] In one embodiment of the present application, X is O; S; Se; Te; or CRaRb.

[0079] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0080] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0081] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0082] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0083] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0084] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0085] In one embodiment of the present application, Ra and Rb are the same or different from each other and are each independently hydrogen; deuterium; or a methyl group.

[0086] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups; or are substituted or unsubstituted divalent heterocyclic groups, or combine with adjacent groups to form substituted or unsubstituted rings.

[0087] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups; or substituted or unsubstituted divalent heteroaryl groups, or combine with adjacent groups to form substituted or unsubstituted rings.

[0088] A1, A2, B1, and B2 are the same or different from each other and each independently combines with the adjacent group to form a substituted or unsubstituted ring, which includes the meaning that the substituted or unsubstituted arylene group; or the meaning that adjacent groups substituted on the substituted or unsubstituted divalent heterocyclic ring combine to form a ring.

[0089] The above ring may be a hydrocarbon ring; or a heteroring.

[0090] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heterocyclic group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0091] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heteroaryl group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0092] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0093] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0094] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heterocyclic group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0095] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or a divalent heteroaryl group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0096] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups having 6 to 30 carbon atoms; or divalent heterocyclic groups having 2 to 30 carbon atoms that are substituted or unsubstituted, or are combined with adjacent groups to form substituted or unsubstituted rings.

[0097] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups having 6 to 20 carbon atoms; or divalent heterocyclic groups having 2 to 20 carbon atoms that are substituted or unsubstituted, or are combined with adjacent groups to form substituted or unsubstituted rings.

[0098] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and each independently has a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent thiophene group, or combines with an adjacent group to form a substituted or unsubstituted ring.

[0099] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and each independently have a phenylene group substituted or unsubstituted with a deuterium, halogen group, or alkyl group; a divalent thiophene group substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with an adjacent group to form a substituted or unsubstituted ring.

[0100] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and each independently have a phenylene group substituted or unsubstituted with a deuterium, halogen group, or alkyl group; a divalent thiophene group substituted or unsubstituted with a deuterium, halogen group, or alkyl group, or are combined with an adjacent group to form a substituted or unsubstituted ring.

[0101] In one embodiment of the present application, A1, A2, B1 and B2 are the same or different from each other and each independently has a phenylene group substituted or unsubstituted with a deuterium, -F, or methyl group; a divalent thiophene group substituted or unsubstituted with a deuterium, -F, or methyl group, or combines with an adjacent group to form a substituted or unsubstituted ring.

[0102] In one embodiment of the present application, Z1 and Z2 are the same or different from each other and are each independently directly coupled; -O-; -S-; C(=O)-; -C(RR')-; -C(F2)O-; -OC(F2)-; -C(=O)O-; -OC(=O)-; -OC(H2)-; -C(H2)O-; -C(R)=C(R')-; -C≡C-; -C(R)=C(R')-C(=O)-; -C(=O)-C(R)=C(R')-; -C(R)=C(R')-C(=O)O-; -OC(=O)-C(R)=C(R')- or -N=N-.

[0103] In one embodiment of the present application, Z1 and Z2 are directly coupled.

[0104] In one embodiment of the present application, Z1 is a direct connection.

[0105] In one embodiment of the present application, Z2 is a direct coupling.

[0106] In one embodiment of the present application, Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0107] In one embodiment of the present application, Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

[0108] In one embodiment of the present application, Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted amide group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0109] In one embodiment of the present application, Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted amide group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0110] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted amide group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0111] By including non-aromatic functional groups in the above Q1 and Q2, solubility in the liquid crystal medium can be increased. When the planarity of the dye itself increases due to the core structure and conjugated system, solubility in the liquid crystal medium decreases, and consequently, a problem of reduced compatibility may occur. However, as in the present invention, by introducing various alkyl chains as non-aromatic functional groups at the ends, solubility can be increased and a dye concentration with a significant effect can be achieved.

[0112] In one embodiment of the present application, the Rc to Rg are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0113] In one embodiment of the present application, the Rc to Rg are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0114] In one embodiment of the present application, the Rc to Rg are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0115] In one embodiment of the present application, R3 is -ORh; -SRh; -N(R)(R') or a substituted or unsubstituted carbazole group, Rh is a cycloalkyl group substituted or unsubstituted with a deuterium, halogen group or alkyl group; or an aryl group substituted or unsubstituted with a deuterium, halogen group or alkyl group, and R and R' are the same or different from each other and are each independently hydrogen; deuterium; a cycloalkyl group substituted or unsubstituted with a deuterium, halogen group or alkyl group; or an aryl group substituted or unsubstituted with a deuterium, halogen group or alkyl group.

[0116] In one embodiment of the present application, R3 is -ORh; -SRh; -N(R)(R') or a substituted or unsubstituted carbazole group.

[0117] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0118] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0119] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0120] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0121] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0122] In one embodiment of the present application, the Rh is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0123] In one embodiment of the present application, the Rh is a cycloalkyl group having 3 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; or a heterocyclic group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group.

[0124] In one embodiment of the present application, the Rh is a cycloalkyl group having 3 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; or a heteroaryl group having 2 to 60 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group.

[0125] In one embodiment of the present application, the Rh is a cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group.

[0126] In one embodiment of the present application, the Rh is a cycloalkyl group having 3 to 20 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; or a heterocyclic group having 2 to 20 carbon atoms substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group.

[0127] In one embodiment of the present application, the Rh is a phenyl group substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group; or a cyclohexyl group substituted or unsubstituted with a deuterium, halogen group, alkyl group, or aryl group.

[0128] In one embodiment of the present application, R and R' are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0129] In one embodiment of the present application, R and R' are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0130] In one embodiment of the present application, R and R' are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0131] In one embodiment of the present application, R and R' are the same or different from each other and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0132] In one embodiment of the present application, R and R' are the same or different from each other and are each independently hydrogen; heavy water; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; or a substituted or unsubstituted heterogoaryl group having 2 to 20 carbon atoms.

[0133] In one embodiment of the present application, the compound of Formula 1 is a dichroic dye compound.

[0134] In one embodiment of the present application, A1 or A2 of the above formula 1 may be the same or different from each other and may each independently be any one of the following formulas A-1 to A-3.

[0135] [Chemical Formula A-1]

[0136]

[0137] [Chemical Formula A-2]

[0138]

[0139] [Chemical Formula A-3]

[0140]

[0141] In the above chemical formulas A-1 to A-3,

[0142] Y is O; S; Se; or CRaRb, and

[0143] Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0144] Rc and Rd are the same or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0145] R11 to R14 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0146] r13 and r14 are each integers from 1 to 4, and if r13 and r14 are each 2 or greater, the substituents in parentheses are the same or different, and

[0147] * is the site that combines with another structure in the above chemical formula 1.

[0148] In one embodiment of the present application, Ra and Rb of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0149] In one embodiment of the present application, Ra and Rb of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0150] In one embodiment of the present application, Ra and Rb of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; or a methyl group.

[0151] In one embodiment of the present application, Rc to Rg of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0152] In one embodiment of the present application, Rc to Rg of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0153] In one embodiment of the present application, Rc to Rg of formulas A-1 and A-3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0154] In one embodiment of the present application, R11 to R14 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0155] In one embodiment of the present application, R11 to R14 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0156] In one embodiment of the present application, R11 to R14 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0157] In one embodiment of the present application, R11 to R14 are the same or different from each other and are each independently hydrogen; deuterium; or an alkyl group having 1 to 10 carbon atoms.

[0158] In one embodiment of the present application, the formula 1 may be any one of the following formulas 2 to 6.

[0159] [Chemical Formula 2]

[0160]

[0161] [Chemical Formula 3]

[0162]

[0163] [Chemical Formula 4]

[0164]

[0165] [Chemical Formula 5]

[0166]

[0167] [Chemical Formula 6]

[0168]

[0169] In the above chemical formulas 2 to 6,

[0170] X, R2, and R3 are as defined in Chemical Formula 1 above, and

[0171] Y1 and Y2 are the same or different from each other, and each is independently O; S; Se; or CRaRb, and

[0172] Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0173] R15 to R22 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; -ORc; -SRd; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0174] R31 to R40 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and

[0175] Rc to Rg are the same or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0176] However, at least one of R31 and R32 has a substituent other than hydrogen, or at least one of R33 and R34 has a substituent other than hydrogen,

[0177] r19, r20, r21, and r22 are each integers from 1 to 4, and when r19, r20, and r21 are each 2 or more, the substituents in parentheses are the same or different.

[0178] In one embodiment of the present application, Y1 and Y2 are S.

[0179] In one embodiment of the present application, Ra and Rb of formulas 2 to 6 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0180] In one embodiment of the present application, Ra and Rb of formulas 2 to 6 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0181] In one embodiment of the present application, Ra and Rb of formulas 2 to 6 are the same or different from each other, and each is independently hydrogen; deuterium; or a methyl group.

[0182] In one embodiment of the present application, Rc to Rg of formulas 2 to 6 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0183] In one embodiment of the present application, Rc to Rg of formulas 2 to 6 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0184] In one embodiment of the present application, Rc to Rg of formulas 2 to 6 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0185] In one embodiment of the present application, R15 to R22 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; -ORc; -SRd; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0186] In one embodiment of the present application, R15 to R22 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; -ORc; -SRd; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

[0187] In one embodiment of the present application, R15 to R22 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; -ORc; -SRd; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0188] In one embodiment of the present application, R15 to R22 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; -ORc; -SRd; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0189] In one embodiment of the present application, R15 to R22 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; -ORc; -SRd; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0190] In one embodiment of the present application, R15 to R22 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; -ORc; -SRd; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0191] In one embodiment of the present application, R31 to R40 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group.

[0192] In one embodiment of the present application, R31 to R40 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

[0193] In one embodiment of the present application, R31 to R40 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted amide group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0194] In one embodiment of the present application, R31 to R40 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted amide group; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0195] In one embodiment of the present application, one or more of R31 and R32 have a substituent other than hydrogen, or one or more of R33 and R34 have a substituent other than hydrogen, and said substituent other than hydrogen is a halogen group.

[0196] In one embodiment of the present application, one or more of R31 and R32 have a substituent other than hydrogen, or one or more of R33 and R34 have a substituent other than hydrogen, and said substituent other than hydrogen is -F.

[0197] In one embodiment of the present application, the chemical formula 1 may be any one of the following compounds.

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] According to one embodiment of the present application, the compound of Formula 1 is a dichroic dye compound.

[0207] The solubility of the compound in liquid crystal according to one embodiment of the present application is 50 wt% or more. The upper limit of the solubility is not limited, but, for example, 100 wt% or less.

[0208] A compound according to one embodiment of the present application has a maximum absorption wavelength within a wavelength range of 550 nm to 750 nm.

[0209] A compound according to one embodiment of the present application has a dichroic ratio (DR) of 8.0 or higher.

[0210] In the present application, the dichroic ratio (DR) is a factor that can confirm anisotropy and means a value (Apar / Aper) obtained by dividing the peak absorbance (Apar) when parallel to the polarization direction with respect to polarized light, such as polarized UV, by the absorbance (Aper) when perpendicular to the polarization direction.

[0211] A compound according to one embodiment of the present application can be used in a liquid crystal display device by dissolving it in a liquid crystal material.

[0212]

[0213] Liquid crystal composition

[0214] One embodiment of the present application provides a liquid crystal composition comprising the aforementioned compound and liquid crystal material.

[0215] In one embodiment of the present application, the liquid crystal material is JNC 5011XX, etc., but is not limited thereto.

[0216] In one embodiment of the present application, the liquid crystal composition may additionally include additives commonly used in the art.

[0217] In one embodiment of the present application, the liquid crystal composition may further include a chiral agent.

[0218] In one embodiment of the present application, the chiral agent may enable the liquid crystal layer to achieve a twisted orientation state. The chiral agent is not particularly limited as long as it can induce the desired twisting without impairing liquid crystal properties (e.g., nematic regularity). The chiral agent for inducing twisting in a liquid crystal material includes chirality in its molecular structure.

[0219] In one embodiment of the present application, the chiral agent may be a compound having one or more asymmetric carbons; a compound having an asymmetric point on a heteroatom, such as a chiral amine or chiral sulfoxide; or a compound having an axially asymmetric, optically active site, such as a cumulene or binaphthol, but is not limited thereto.

[0220] In one embodiment of the present application, the chiral agent may be, for example, a low molecular weight compound having a molecular weight of 1,500 g / mol or less. As the chiral agent, commercially available chiral nematic liquid crystals may be used, for example, the chiral dopant liquid crystal S-811 commercially available from Merck or LC756 from BASF.

[0221] The application ratio of the chiral agent is selected to achieve a desired d (cell thickness) / p (helical pitch of the liquid crystal material) ratio in the liquid crystal layer. Generally, the content (weight%) of the chiral agent can be calculated using the formula 100 / HTP (Helixcal Twisting Power) × Pitch (p) (nm). The HTP represents the twisting strength of the chiral agent. Referring to the above method, the content of the chiral agent can be determined by considering the desired pitch. In one example, the content of the chiral agent may be 0.5 to 10 parts by weight per 100 parts by weight of the liquid crystal material. Specifically, the content of the chiral agent may be 1 to 7 parts by weight, or 1 to 5 parts by weight, per 100 parts by weight of the liquid crystal material.

[0222]

[0223] liquid crystal cell

[0224] Another embodiment of the present application provides a liquid crystal cell comprising a first substrate; a liquid crystal layer; and a second substrate, wherein the liquid crystal layer comprises the liquid crystal composition described above.

[0225] In one embodiment of the present application, the liquid crystal cell comprises a first substrate, a liquid crystal layer on one surface of the first substrate, and a second substrate on the surface opposite to the surface of the liquid crystal layer facing the first substrate.

[0226] Referring to FIG. 1, a liquid crystal cell according to one embodiment of the present application may include a structure stacked in the order of a first substrate (10); a liquid crystal layer (20); and a second substrate (30).

[0227] A liquid crystal cell according to one embodiment of the present application may include additional structures as needed in addition to the first substrate, the liquid crystal layer, and the second substrate. For example, the liquid crystal cell may further include an adhesive layer.

[0228] In addition to including a liquid crystal layer comprising the liquid crystal composition described above, a liquid crystal cell according to one embodiment of the present application may be subject to known techniques.

[0229] In one embodiment of the present application, the first substrate and the second substrate are not particularly limited, but, for example, a glass film, a crystalline or amorphous silicon film, an inorganic film such as quartz or ITO (Indium Tin Oxide) film, or a polymer film may be used.

[0230] In one embodiment of the present application, the first substrate and the second substrate may be polymer films.

[0231] In one embodiment of the present application, the polymer film may be TAC (triacetyl cellulose); COP (cyclo olefin copolymer) such as norbornene derivatives; PMMA (poly(methyl methacrylate); PC (polycarbonate); PE (polyethylene); PP (polypropylene); PVA (polyvinyl alcohol); DAC (diacetyl cellulose); Pac (Polyacrylate); PES (poly ether sulfone); PEEK (polyetheretherketon); PEI (polyetherimide); PPS (polyphenylsulfone); PEN (polyethylenemaphthatlate); PET (polyethyleneterephtalate); PI (polyimide); PSF (polysulfone); PAR (polyarylate) or amorphous fluoropolymer, but is not limited thereto.

[0232] In one embodiment of the present application, the first substrate and the second substrate may, if necessary, include a coating layer of a silicon compound such as gold, silver, silicon dioxide or silicon monoxide, or a coating layer such as an anti-reflective layer.

[0233] In one embodiment of the present application, the thickness of the first substrate and the second substrate may each be about 10 μm to about 1,000 μm.

[0234] In one embodiment of the present application, the thickness of the first substrate and the second substrate may each be 20 μm or more, 40 μm or more, 60 μm or more, 80 μm or more, 100 μm or more, 120 μm or more, 140 μm or more, 160 μm or more, or 180 μm or more, and may be 900 μm or less, 800 μm or less, 700 μm or less, 600 μm or less, 500 μm or less, or 400 μm or less. When the thickness of the first substrate and the second substrate satisfies the above range, when manufacturing a transmittance variable device by bonding a liquid crystal cell with an outer substrate, appearance defects such as wrinkles can be reduced.

[0235] In one embodiment of the present application, the liquid crystal layer may be a GHLC layer (Guest host liquid crystal layer), but is not limited thereto.

[0236] In one embodiment of the present application, the thickness of the liquid crystal layer may be 0.01 μm to 30 μm, but is not particularly limited.

[0237] In one embodiment of the present application, the thickness of the liquid crystal layer may be 0.05 μm or more, 0.1 μm or more, 0.5 μm or more, 1 μm or more, 1.5 μm or more, 2 μm or more, 2.5 μm or more, 3 μm or more, 3.5 μm or more, 4 μm or more, 4.5 μm or more, 5 μm or more, 5.5 μm or more, 6 μm or more, 6.5 μm or more, 7 μm or more, 7.5 μm or more, or 8 μm or more, and may be 25 μm or less, 20 μm or less, or 15 μm or less.

[0238] In one embodiment of the present application, the liquid crystal layer may change its orientation state depending on the voltage applied to the liquid crystal cell. For example, when no voltage is applied to the liquid crystal cell, the liquid crystal layer may have a first orientation state, and when voltage is applied to the liquid crystal cell, the liquid crystal layer may have a second orientation state different from the first orientation state. The first orientation state and the second orientation state may each be selected from a horizontal orientation state, a vertical orientation state, a twist orientation state, an inclined orientation state, a hybrid orientation state, etc.

[0239] The above horizontal orientation state refers to a state in which the directors of the liquid crystal material within the liquid crystal layer are arranged approximately parallel to the plane of the liquid crystal layer. For example, the angle formed by the directors with respect to the plane of the liquid crystal layer may be approximately -10° to 10°, or -5° to 5°, or approximately 0°.

[0240] The above vertical orientation state is a state in which the directors of the liquid crystal material within the liquid crystal layer are arranged approximately perpendicularly to the plane of the liquid crystal layer, and for example, the angle formed by the directors with respect to the plane of the liquid crystal layer may be approximately 80° to 100°, or 85° to 95°, or approximately 90°.

[0241] The above twisted orientation state may refer to a helical structure in which the directioners of the liquid crystal material within the liquid crystal layer are twisted along a virtual helical axis to form layers. The above twisted orientation state can be implemented in a vertical, horizontal, or oblique orientation state; that is, the vertical twisted orientation mode is a state in which individual liquid crystal materials are vertically oriented and twisted along a helical axis to form layers, the horizontal twisted orientation mode is a state in which individual liquid crystal materials are horizontally oriented and twisted along a helical axis to form layers, and the oblique twisted orientation mode is a state in which individual liquid crystal compounds are obliquely oriented and twisted along a helical axis to form layers.

[0242] The above hybrid orientation state may refer to an orientation state in which the tilt angle, which is the angle formed by the directioner of the liquid crystal material within the liquid crystal layer with respect to the plane of the liquid crystal layer, gradually increases or decreases along the thickness direction of the liquid crystal layer.

[0243]

[0244] Liquid crystal display

[0245] Another embodiment of the present application provides a liquid crystal display device comprising the liquid crystal cell described above.

[0246] In one embodiment of the present application, the liquid crystal display device may be applied to a lens, a vehicle sunroof, a smart window, etc.

[0247] The present invention will be explained in more detail below through examples. However, the following examples are intended to illustrate the present invention and do not limit the scope of the present invention.

[0248] Synthesis Example. Synthesis of Compounds

[0249] Synthesis Example 1: Synthesis of Compound 1

[0250] Compound 1, a dichroic dye, was synthesized through the following reaction.

[0251] (1) Synthesis of intermediates 1-3

[0252]

[0253] Intermediate 1-1 (1.0 eq), intermediate 1-2 (2.5 eq), tetracyclophenylphosphine palladium (0) (0.02 eq), potassium carbonate (4.0 eq), and THF / water in a 4:1 ratio were added and stirred at 80°C for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, then the substance was extracted using dichloromethane and water. After removing the water by treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. The product was recrystallized with dichloromethane and ethanol to obtain intermediate 1-3 (90%).

[0254]

[0255] (2) Synthesis of intermediates 1-4

[0256]

[0257] Under a nitrogen atmosphere, the above intermediate 1-3 (1.0 eq) was placed in a flask with DMF and stirred. N-bromosuccinimide (2.0 eq) was slowly added dropwise to the reaction mixture, and the mixture was stirred at 60°C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, ethanol was added, and the mixture was stirred. The mixture was filtered to obtain intermediate 1-4 (95%).

[0258]

[0259] (3) Synthesis of intermediates 1-5

[0260]

[0261] The above intermediate 1-4 (1.0 eq) and Fe (10 eq) were placed in a flask, AcOH was added, and the mixture was stirred at 80°C for 3 hours. Subsequently, Glyoxylic acid (1.0 eq) was added and stirred for 1 hour, followed by Celite filtering. The filtrate was subjected to EA / H2O extraction, treated with anhydrous magnesium sulfate to remove water, filtered, and concentrated under reduced pressure. The product was recrystallized with dichloromethane and ethanol to obtain intermediate 1-5 (70%).

[0262]

[0263] (4) Synthesis of intermediates 1-6

[0264]

[0265] The above intermediates 1-5 (1.0 eq) were dissolved in DCM and cooled to -10℃. Subsequently, POCl3 (10 eq) was added dropwise over 1 hour, after which the temperature was raised to room temperature and stirred for 1 hour. After confirming the completion of the reaction, the mixture was concentrated by reducing the pressure without further purification and used in the next reaction.

[0266]

[0267] (5) Synthesis of intermediates 1-8

[0268]

[0269] The above intermediates 1-6 (1.0 eq) and K2CO3 (2 eq) intermediates 1-7 (1.1 eq) were dissolved in DMF and stirred for 1 hour. After the reaction was finished, water was added to the mixture, and the formed solid was filtered to obtain intermediate 1-8 (90%).

[0270]

[0271] (6) Synthesis of Compound 1

[0272]

[0273] Intermediate 1-8 (1.0 eq), intermediate 1-9 (2.5 eq), tetracyclophenylphosphine palladium (0) (0.02 eq), potassium carbonate (4.0 eq), and THF / water in a 4:1 ratio were added and stirred at 80°C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature, then the substance was extracted using dichloromethane and water. After removing the water by treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. The product was recrystallized with acetone and ethanol to obtain compound 1 (70%).

[0274]

[0275] Synthesis Example 2: Synthesis of Compound 2

[0276] (1) Synthesis of intermediate 2-2

[0277]

[0278] The synthesis method is the same as in the synthesis example of intermediate 1-8, except that intermediate 2-1 was used instead of intermediate 1-7.

[0279]

[0280] (2) Synthesis of Compound 2

[0281]

[0282] The synthesis method is the same as in the synthesis example of compound 1, except that intermediate 2-2 is used instead of intermediate 1-8 and intermediate 2-3 is used instead of intermediate 1-9.

[0283]

[0284] Synthesis Example 3: Synthesis of Compound 3

[0285]

[0286] The synthesis method is the same as in the synthesis example of compound 1, except that intermediate 1-10 was used instead of intermediate 1-9.

[0287]

[0288] Comparative Compound 1: A compound that does not contain two aryl groups (or heterocyclic groups) on both sides of the thiadiazoloquinoxaline skeletal structure

[0289]

[0290]

[0291] Comparative Compound 2: A compound that differs from the present invention in that it does not contain two aryl groups (or heterocyclic groups) on both sides of the thiadiazoloquinoxaline skeletal structure and that R3 is an -O-alkyl group.

[0292]

[0293]

[0294] Comparative Compound 3: A compound in which R3 is a phenyl group, different from R3 of the present invention.

[0295]

[0296]

[0297] Comparative Compound 4: A compound that differs from Compound 1 only in that it has only one heteroaryl group at both ends.

[0298]

[0299]

[0300] Comparative Compound 5: A compound that differs from Compound 1 only in that R3 is an aryl group.

[0301]

[0302] <Experimental Example: Measurement of Physical Properties of Dichroic Dyes>

[0303] The physical properties of each of the above compounds 1 to 3 and comparative compounds 1 to 5 as dichroic dyes were measured by the following method, and the results are shown in Table 1.

[0304]

[0305] 1. Experimental Example 1: Solubility

[0306] The solubility measurements for each of the above compounds 1 to 3 and comparative compounds 1 to 5 were performed in a liquid crystal film cell as follows.

[0307] Specifically, 8 parts by weight each of compounds 1 to 3 and comparative compounds 1 to 5 were mixed with 100 parts by weight of a liquid crystal compound (using Mixture LC obtained from Bayi) containing (trans, trans) -4-Ethenyl-4'-propoyl-1,1'-bicyclohexyl, trans-1-Ethoxy-4-(4-propylcyclohexyl)-4-yl]benzene, 5-(Difluoro[(trans,trans)-4'-propyl [1,1'-bicyclohexyl]-4-yl' methoxy'-1,2,3-trifluorobenzene, [1,1-Bicyclohexyl]-4-carboxylic acid, and 4-propyl-3,4,5-trifluorophenyl ester, then a magnetic bar was added and stirred at 60°C for about 2 hours.

[0308] Then, after leaving the liquid crystal mixture in an orbital shaker for about 12 hours or more, the liquid crystal mixture was filtered through a 0.2 μm PP filter to produce a liquid crystal film cell, and the solubility of the dye (compounds 1 to 3 and comparative compounds 1 to 5) was analyzed through this.

[0309] The transmittance of the above compounds 1 to 3 and comparative compounds 1 to 5 according to their concentrations was measured to examine the concentration range in which transmittance increases despite the increase in concentration. In addition, to confirm this, UV-Vis spectra were taken to observe changes in the spectrum shape. Furthermore, the liquid crystal film cell was observed under a microscope to see if dye clumping occurred depending on the angle of the dye, and the results are shown in Table 1 below.

[0310]

[0311] 2. Experimental Example 2: Reliability (Contrast Ratio (CR)) Evaluation

[0312] A liquid crystal medium sample was prepared by adding compounds (each of compounds 1 to 3 and comparative compounds 1 to 5) and a liquid crystal compound (BYNB-25 of Bayi) in a weight ratio of 2:98, and then filtered through a 0.2 μm PP filter to produce a liquid crystal film cell.

[0313] A liquid crystal film cell capable of voltage application was obtained by connecting electrode tapes to the upper and lower PET-ITO plates of the above liquid crystal film cell. After mounting the liquid crystal film cell on the Nippon-Denshoku NHD7000 (haze meter), voltage was applied to the liquid crystal film cell using a voltage application device (function generator) to measure the total transmittance (T.T0V, T.T50V) at 0V and 50V.

[0314] Then, using the above transmittance values, the contrast ratio (CR) was measured according to the following formula, and the results are as shown in Table 1 below.

[0315] Contrast Ratio (CR) = T.T50V(%) / T.T0V(%)

[0316] No. Compound Solubility (parts by weight, based on 100 parts by weight of liquid crystal compound) CR (Contrast Ratio) Example 1 Compound 15.0 15.0 Example 2 Compound 24.0 14.0 Example 3 Compound 33.0 15.0 Comparative Example 1 Comparative Compound 11.0 10.0 Comparative Example 2 Comparative Compound 21.5 10.0 Comparative Example 3 Comparative Compound 31.0 12.0 Comparative Example 4 Comparative Compound 4 <1.0 3.0 Comparative Example 5 Comparative Compound 5 3.0 14.0

[0317] According to Table 1 above, Examples 1 to 3 containing a compound satisfying Formula 1 of the present invention as a dye were found to have superior solubility and superior contrast ratio compared to Comparative Examples 1 to 5 containing Comparative Compounds 1 to 5.

Claims

1. Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above chemical formula 1, X is O; S; Se; Te; or CRaRb, and Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and A1, A2, B1, and B2 are the same or different from each other and are each independently substituted or unsubstituted arylene groups; or are substituted or unsubstituted divalent heterocyclic groups, or can combine with adjacent groups to form substituted or unsubstituted rings, and Z1 and Z2 are equal to or different from each other and are each independently directly coupled; -O-; -S-; C(=O)-; -C(RR')-; -C(F2)O-; -OC(F2)-; -C(=O)O-; -OC(=O)-; -OC(H2)-; -C(H2)O-; -C(R)=C(R')-; -C≡C-; -C(R)=C(R')-C(=O)-; -C(=O)-C(R)=C(R')-; -C(R)=C(R')-C(=O)O-; -OC(=O)-C(R)=C(R')- or -N=N- and, Q1, Q2 and R2 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and Rc to Rg are the same or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R3 is -ORh; -SRh; -N(R)(R') or a substituted or unsubstituted carbazole group, and Rh is a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R and R' are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups are combined to form a substituted or unsubstituted ring.

2. A compound according to claim 1, wherein A1 or A2 of formula 1 is the same or different from each other and each independently is any one of the following formulas A-1 to A-3: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above chemical formulas A-1 to A-3, Y is O; S; Se; or CRaRb, and Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and Rc and Rd are the same or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R11 to R14 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and r13 and r14 are each integers from 1 to 4, and if r13 and r14 are each 2 or greater, the substituents in parentheses are the same or different, and * is the site that combines with another structure in the above chemical formula 1.

3. A compound according to claim 1, wherein the chemical formula 1 is any one of the following chemical formulas 2 to 6: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 2 to 6, X, R2, and R3 are as defined in Chemical Formula 1 above, and Y1 and Y2 are the same or different from each other, and each is independently O; S; Se; or CRaRb, and Ra and Rb are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; -ORc; -SRd; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R15 to R22 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; -ORc; -SRd; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R31 to R40 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -ORc; -SRd; -N(Re)(Rf); Si(Rg)3; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkynyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heterocyclic group, and Rc to Rg are the same or different from one another, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and However, at least one of R31 and R32 has a substituent other than hydrogen, or at least one of R33 and R34 has a substituent other than hydrogen, r19, r20, r21, and r22 are each integers from 1 to 4, and when r19, r20, and r21 are each 2 or more, the substituents in parentheses are the same or different.

4. In Claim 1, The above R3 is -ORh; -SRh; -N(R)(R') or is a substituted or unsubstituted carbazole group, and The above Rh is a cycloalkyl group substituted or unsubstituted with a deuterium, halogen group, or alkyl group; or an aryl group substituted or unsubstituted with a deuterium, halogen group, or alkyl group, and A compound in which the above R and R' are the same or different from each other and each independently is hydrogen; deuterium; a cycloalkyl group substituted or unsubstituted with deuterium, a halogen group or an alkyl group; or an aryl group substituted or unsubstituted with deuterium, a halogen group or an alkyl group.

5. A compound according to Claim 1, wherein the compound of Formula 1 is any one of the following compounds: .

6. A liquid crystal composition comprising a compound according to any one of claims 1 to 5; and a liquid crystal material.

7. A liquid crystal composition according to claim 6, further comprising a chiral agent.

8. A liquid crystal cell comprising a first substrate; a liquid crystal layer; and a second substrate, The liquid crystal layer is a liquid crystal cell comprising a liquid crystal composition according to claim 6.

9. A liquid crystal display device comprising a liquid crystal cell according to claim 8.

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