Dichroic dye compound, liquid crystal composition, liquid crystal cell, and liquid crystal display device

Abstract

One embodiment of the present application relates to a dichroic dye composition including a first compound and a second compound, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device. When the dichroic dye composition according to one embodiment of the present application is used in a liquid crystal composition, it is possible to provide a liquid crystal composition which is excellent in terms of performance, appearance, stability, and reliability even under difficult working conditions such as temperature rise or direct and extended sunlight irradiation.

Description

Dichroic dye composition, liquid crystal composition, liquid crystal cell and liquid crystal display device

[0001] The present application claims the benefit of the filing date of Korean Patent Application No. 10-2025-0011192 filed with the Korean Intellectual Property Office on January 24, 2025, and the filing date of Korean Patent Application No. 10-2026-0010926 filed with the Korean Intellectual Property Office on January 20, 2026, and all contents disclosed in the documents of said Korean patent applications are incorporated into this specification.

[0002] The present application relates to a dichroic dye composition, 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 dyes 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 literature

[0007] (Patent Document 1) Republic of Korea Published Patent Application No. 10-2014-0020064

[0008] The present application aims to provide a dichroic dye composition, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device.

[0009] One embodiment of the present application provides a dichroic dye composition comprising a first compound represented by the following chemical formula 1; and a second compound represented by any one of the following chemical formulas 2 to 4.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] V1 to V4 are the same or different from one another, and each is an independently substituted or unsubstituted divalent aryl group; or a substituted or unsubstituted divalent heteroaryl group, and

[0014] U1 to U4 are the same or different from one another 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')-; -NH-C(=O)-; -C(=O)-NH-; or -N=N-, and

[0015] P1 to P4 are the same or different from one another and each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof, wherein K3 and K4 of -N(K3)(K4) combine with V1, V2, V3, or V4 to form a substituted or unsubstituted N-containing ring, and

[0016] K1 to K7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted alkoxy group, and

[0017] n1 to n4 are each 0 or 1, and

[0018] m1 to m4 are each integers from 1 to 5, and if m1 to m4 are each 2 or greater, the structures inside the parentheses are the same or different from each other,

[0019] [Chemical Formula 2]

[0020]

[0021] [Chemical Formula 3]

[0022]

[0023] [Chemical Formula 4]

[0024]

[0025] In the above chemical formulas 2 to 4,

[0026] X is a substituted or unsubstituted pyrazine ring; a substituted or unsubstituted quinoxaline ring; or a substituted or unsubstituted pyrrolidine-2,5-dione ring, and

[0027] Z1 and Z2 are equal to or different from each other, and each is independently -C(R3)-; or -N-, and

[0028] If both Z1 and Z2 are -C(R3)-, R3 is the same or different, and

[0029] R1 to R3 are the same or different from one another, and each independently is hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, or combines with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring, and

[0030] Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0031] H1 and H2 are identical or different from each other and are each independently substituted or unsubstituted divalent heterocyclic rings, and

[0032] L1 and L2 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-; or -OC(=O)-C(R)=C(R')- and,

[0033] L3 to L6 are the same or different from one another and are each independently directly coupled; -O-; -S-; -N=N-; -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-; or -OC(=O)-C(R)=C(R')- and,

[0034] Y1 is N; or C(R4), and

[0035] Y2 is N; or C(R5), and

[0036] R4 and R5 are the same or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, or combined with each other to form a substituted or unsubstituted cyclohexane ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted pyrazine ring, and

[0037] Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted heterocycloalkyl group; or a combination thereof,

[0038] Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted alkoxy group, and Ra and Rb of -N(Ra)(Rb) combine with A1 or A2 to form a substituted or unsubstituted N-containing ring, and

[0039] A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or are substituted or unsubstituted divalent heteroaryl groups, or each combine with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring, and

[0040] o1 and o2 are each integers from 0 to 3, and if each is 2 or greater, the structure inside the parentheses is the same or different, and

[0041] Q3 and Q4 are the same or different from each other and are each independently -N(Ra')(Rb'); -Si(Ra')(Rb')(Rc'); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a combination thereof,

[0042] Ra' to Rc' are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkoxy group, and Ra' and Rb' of -N(Ra')(Rb') combine with A3 or A4 to form a substituted or unsubstituted N-containing ring when L5 or L6 is a direct bond, and

[0043] A3 and A4 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or are substituted or unsubstituted divalent heteroaryl groups, and where L5 or L6 is a direct bond, they each combine with Ra' and Rb' among the -N(Ra')(Rb') of Q3 and Q4 to form a substituted or unsubstituted N-containing ring, and

[0044] In the above chemical formulas 1 to 4,

[0045] R and R' are the same or different from each other and are each independently hydrogen; deuterium; 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 heteroaryl group.

[0046] In addition, another embodiment of the present application provides a liquid crystal composition comprising the dichroic dye composition and the liquid crystal material.

[0047] 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.

[0048] In addition, another embodiment of the present application provides a liquid crystal display device including the liquid crystal cell.

[0049] When a dichroic dye composition 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 reliability can be provided even under demanding operating conditions such as increased temperature or direct and extended sunlight irradiation.

[0050] In addition, the dichroic dye composition exhibits excellent solubility in a liquid crystal medium and can achieve a meaningful and effective dye concentration within the liquid crystal medium, which can favorably contribute to the contrast ratio and switching performance obtainable in a switchable device.

[0051] FIG. 1 is a diagram illustrating the structure of a liquid crystal cell according to one embodiment of the present application.

[0052] <Explanation of Symbols>

[0053] 10: First substrate

[0054] 20: Liquid crystal layer

[0055] 30: Second substrate

[0056] The present application will be described in more detail below.

[0057] 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.

[0058] Examples of substituents in this specification are described below, but are not limited thereto.

[0059] 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.

[0060] In this specification, the term “substituted or unsubstituted” means one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; hydroxyl group; oxygen (=O); amine group; nitro group; silyl group; ester group; sulfide group; alkyl group; haloalkyl group; alkenyl group; cycloalkyl group; alkoxy group; aryloxy group; aryl group; and heterocyclic group, or two or more of the exemplified substituents are connected to a substituent, or have no substituents.

[0061] In this specification, hydrogen includes all of hydrogen; deuterium; and tritium.

[0062] In this specification, the halogen group is fluorine, chlorine, bromine, or iodine.

[0063] In this specification, the amine group is -NR 101 R 102 It can be represented as, and R 101 and R 102 Each is independently hydrogen, deuterium, alkyl group, alkenyl group, aryl group, or heterocyclic group. The number of carbon atoms in the amine group is not particularly limited, but is preferably 0 to 30.

[0064] In this specification, the silyl group is -SiR 103 R 104 R 105 It can be represented as, and R 103 , R 104 and R 105 Each is independently hydrogen, deuterium, alkyl group, alkenyl group, aryl group, or heterocyclic group. Specific examples include, but are not limited to, trimethylsilyl group, triethylsilyl group, triphenylsilyl group, diphenylsilyl group.

[0065] In this specification, the ester group is -C(=O)OR 106 , or -OC(=O)R 106 Indicated as, and the above R 106 The ester group 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.

[0066] In this specification, the sulfide group is -SR 107 Indicated as, and the above R 107 The ester group 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.

[0067] 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.

[0068] 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.

[0069] 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 30.

[0070] In the present specification, the alkyne 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 30.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] In this specification, the alkyl carbonyl group is -C(=O)R 108 Indicated as, and R 108 is an alkyl group, and the description of the aforementioned alkyl group may apply.

[0081] In this specification, the alkoxycarbonyl group is -C(=O)R 109 Indicated as, and R 109 is an alkoxy group, and the description of the alkoxy group described above can be applied.

[0082] In this specification, the alkyl carbonyloxy group is -OC(=O)R 110 Indicated as, and R 110 is an alkyl group, and the description of the aforementioned alkyl group may apply.

[0083] In this specification, the alkoxycarbonyloxy group is -OC(=O)R 111 Indicated as, and R 111 is an alkoxy group, and the description of the alkoxy group described above can be applied.

[0084] 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.

[0085] In this 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.

[0086] 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.

[0087] The examples of the aforementioned heterocyclic rings apply to the aliphatic heterocyclic rings and aromatic heterocyclic rings, except that each is not monovalent.

[0088] 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.

[0089] 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.

[0090]

[0091] Dichroic dye composition

[0092] One embodiment of the present application provides a dichroic dye composition comprising a first compound represented by the following chemical formula 1; and a second compound represented by any one of the following chemical formulas 2 to 4.

[0093] [Chemical Formula 1]

[0094]

[0095] [Chemical Formula 2]

[0096]

[0097] [Chemical Formula 3]

[0098]

[0099] [Chemical Formula 4]

[0100]

[0101] The definitions of the substituents of the above chemical formulas 1 to 4 are as described above.

[0102] The dichroic dye composition of the present application is characterized by comprising a nickel compound represented by the above chemical formula 1 and a compound represented by any one of the above chemical formulas 2 to 4.

[0103] In particular, by including a nickel composite compound, advantages in terms of performance, appearance, stability, and reliability can be provided even when used under demanding conditions such as increased temperature or direct and extended solar irradiation.

[0104] In addition, the second compound includes a specific condensed ring structure (quinoxaline, pyridopyrazine, pyrazinopyridazine) containing a pyrazine ring in the compound core portion (corresponding to Chemical Formula 2), or includes a structure in which a thiophene ring and an X ring are condensed (corresponding to Chemical Formula 3), and includes non-aromatic functional groups in the terminal Q1 and Q2 structures, and includes a structure of -A1(A2)-L1(L2)-H1(H2)- between the core and the terminals. Alternatively, a dichroic dye with a high absorption coefficient can be synthesized by including a structure in which a 1,2,5-thiadiazole ring and a Y1 and Y2-containing ring are condensed (corresponding to Chemical Formula 4), and with such structural features at the ends, the amount of dichroic dye used can be reduced. Additionally, by forming a conjugation system centered on the core structure, compatibility and reliability in the liquid crystal structure can be improved, and the dichroic ratio can be increased, thereby providing advantages in terms of performance, appearance, stability, and reliability even when used under demanding conditions.

[0105] The function of the electron acceptor is maximized by including a specific condensed ring containing a pyrazine ring as a core structure (corresponding to Formula 2) or a ring formed by the condensation of a thiophene ring, a pyrazine ring, a quinoxaline ring, or a pyrrolidine-2,5-dione ring (corresponding to Formula 3) as a core structure.

[0106] Furthermore, heterocyclic groups (heteroaryls) are formed on both sides of the core structure as H1 and H2, acting as electron donors; this maximizes the ability to sufficiently transfer electrons to the electron acceptor in the core structure.

[0107] L1 and L2, which are structures connected to the above H1 and H2, are non-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.

[0108] Finally, by including non-aromatic functional groups at the ends (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.

[0109]

[0110] 1st compound

[0111] A dichroic dye composition according to one embodiment of the present application comprises the first compound of Formula 1.

[0112] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or substituted or unsubstituted divalent heteroaryl groups.

[0113] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C60 aryl groups; or substituted or unsubstituted divalent C2 to C60 heteroaryl groups.

[0114] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C30 aryl groups; or substituted or unsubstituted divalent C2 to C30 heteroaryl groups.

[0115] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C20 aryl groups; or substituted or unsubstituted divalent C2 to C20 heteroaryl groups.

[0116] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent biphenyl group; or a substituted or unsubstituted divalent dibenzothiophene group.

[0117] In one embodiment of the present application, V1 to V4 are the same or different from each other and are each independently substituted or unsubstituted divalent phenyl groups; or substituted or unsubstituted divalent dibenzothiophen groups.

[0118] In one embodiment of the present application, the repetition numbers n1 to n4 of V1 to V4 are each 0 or 1.

[0119] In one embodiment of the present application, n1 to n4 may be 0.

[0120] In one embodiment of the present application, n1 to n4 may be 1.

[0121] In one embodiment of the present application, U1 to U4 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')-; -NH-C(=O)-; -C(=O)-NH-; or -N=N-.

[0122] In one embodiment of the present application, U1 to U4 are the same or different from each other and are each independently directly coupled; -C(=O)O-; -OC(=O)-; -C(R)=C(R')-; -NH-C(=O)-; or -C(=O)-NH-.

[0123] In one embodiment of the present application, U1 to U4 are direct couplings.

[0124] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0125] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0126] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0127] In one embodiment of the present application, P1 to P4 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted ester group; -O(K1); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0128] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted ester group; -O(K1); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0129] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted ester group; -O(K1); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0130] In one embodiment of the present application, P1 to P4 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted C1 to C10 alkyl group; substituted or unsubstituted ester group; -O(K1); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0131] In one embodiment of the present application, the K1 to K7 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted alkoxy group.

[0132] In one embodiment of the present application, the K1 to K7 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted C1 to C60 alkoxy group.

[0133] In one embodiment of the present application, the K1 to K7 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a substituted or unsubstituted C1 to C30 alkoxy group.

[0134] In one embodiment of the present application, the K1 to K7 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C1 to C60 alkoxy group.

[0135] In one embodiment of the present application, the K1 to K7 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C1 to C30 alkoxy group.

[0136] In one embodiment of the present application, m1 to m4 are each integers from 1 to 5, and when m1 to m4 are each 2 or more, the structures inside the parentheses are the same or different from each other.

[0137] In one embodiment of the present application, m1 to m4 may be 1 or 2.

[0138] In one embodiment of the present application, when m1 to m4 are 2 or more, the structure within the parentheses includes a structure arranged in units of 2 or more. For example, when m1 is 2, it may include a structure of -U1-P1-U1'-P1', where U1' and P1' are identical to the definitions of U1 and P1, respectively.

[0139] In one embodiment of the present application, the formula 1 may be represented by any one of the following formulas 1-1 to 1-4.

[0140] [Chemical Formula 1-1]

[0141]

[0142] [Chemical Formula 1-2]

[0143]

[0144] [Chemical Formula 1-3]

[0145]

[0146] [Chemical Formula 1-4]

[0147]

[0148] In the above chemical formulas 1-1 to 1-4,

[0149] E1 to E4 are the same or different from each other, and each is independently O; S; or N, and

[0150] O1 to O8 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof,

[0151] K1 to K7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted alkoxy group, and

[0152] The definitions of the remaining substituents are the same as the definitions in Chemical Formula 1 above.

[0153] In one embodiment of the present application, Q1 to Q8 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof.

[0154] In one embodiment of the present application, Q1 to Q8 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a carboxyl group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted ester group; -O(K1); or a combination thereof.

[0155] In one embodiment of the present application, the first compound may be any one of the following compounds.

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162] second compound

[0163] In one embodiment of the present application, the second compound is represented by any one of the following chemical formulas 2 to 4.

[0164] [Chemical Formula 2]

[0165]

[0166] [Chemical Formula 3]

[0167]

[0168] [Chemical Formula 4]

[0169]

[0170] In the above chemical formulas 2 to 4, the definition of each substituent is as described above.

[0171] In one embodiment of the present application, the second compound may be represented by the formula 2 or 3.

[0172] <Chemical Formula 2>

[0173] In one embodiment of the present application, the second compound may be represented by the formula 2.

[0174] In one embodiment of the present application, Z1 and Z2 are the same or different from each other and are each independently -C(R3)-; or -N-.

[0175] In one embodiment of the present application, Z1 and Z2 may be -C(R3)- and R3 may be the same or different.

[0176] In one embodiment of the present application, Z1 and Z2 may be -N-.

[0177] In one embodiment of the present application, Z1 may be -C(R3)- and Z2 may be -N-.

[0178] In one embodiment of the present application, Z1 may be -N- and Z2 may be -C(R3)-.

[0179] In one embodiment of the present application, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring.

[0180] In one embodiment of the present application, R1 to R3 are the same or different from each other and each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof, or combine with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring.

[0181] In one embodiment of the present application, R1 to R3 are the same or different from each other and each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof, or combine with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring.

[0182] In one embodiment of the present application, R1 to R3 are the same or different from each other and each independently in one embodiment of the present application, R1 to R3 are the same or different from each other and each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof, or combine with adjacent groups to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring.

[0183] In one embodiment of the present application, the formula 2 may be represented by any one of the following formulas 2-1 to 2-8.

[0184] [Chemical Formula 2-1]

[0185]

[0186] [Chemical Formula 2-2]

[0187]

[0188] [Chemical Formula 2-3]

[0189]

[0190] [Chemical Formula 2-4]

[0191]

[0192] [Chemical Formula 2-5]

[0193]

[0194] [Chemical Formula 2-6]

[0195]

[0196] [Chemical Formula 2-7]

[0197]

[0198] [Chemical Formula 2-8]

[0199]

[0200] In the above chemical formulas 2-1 to 2-8,

[0201] R11 to R18 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof,

[0202] Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0203] The definitions of the remaining substituents are the same as the definitions in Chemical Formula 2 above.

[0204] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); a C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

[0205] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); a C1 to C40 haloalkyl group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0206] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); a C1 to C30 haloalkyl group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0207] In one embodiment of the present application, R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); a haloalkyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0208] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); a C1 to C60 haloalkyl group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0209] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); a C1 to C30 haloalkyl group; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C6 to C30 aryl group.

[0210] In one embodiment of the present application, the R11 to R18 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a cyano group; -O(Rd); -S(Re); a C1 to C20 haloalkyl group; a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0211] In one embodiment of the present application, the formula 2 may be represented by any one of the following formulas 2-1-1 to 2-1-9.

[0212] [Chemical Formula 2-1-1]

[0213]

[0214] [Chemical Formula 2-1-2]

[0215]

[0216] [Chemical Formula 2-1-3]

[0217]

[0218] [Chemical Formula 2-1-4]

[0219]

[0220] [Chemical Formula 2-1-5]

[0221]

[0222] [Chemical Formula 2-1-6]

[0223]

[0224] [Chemical Formula 2-1-7]

[0225]

[0226] [Chemical Formula 2-1-8]

[0227]

[0228] In the above chemical formulas 2-1-1 to 2-1-8,

[0229] Y3 and Y4 are equal to or different from each other, and each is independently O; S; Se; or N(R27), and

[0230] R11 to R18 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -S(Rd); -C(=O)O(Re); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryl group; or a combination thereof,

[0231] Rd and Re are the same or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group, and

[0232] R21 to R27 are the same or different from one another, and each is independently hydrogen; deuterium; a halogen group; a cyano group; an ester group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted alkoxy group, and

[0233] a and b are each integers from 1 to 4, and when a and b are each 2 or greater, the substituents inside the parentheses are the same or different, and

[0234] The definitions of the remaining substituents are the same as the definitions in Chemical Formula 2 above.

[0235] In one embodiment of the present application, R21 to R27 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0236] In one embodiment of the present application, R21 to R27 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C1 to C60 alkoxy group.

[0237] In one embodiment of the present application, R21 to R27 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C1 to C30 alkoxy group.

[0238] In one embodiment of the present application, R21 to R27 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C15 alkyl group; or a substituted or unsubstituted C1 to C15 alkoxy group.

[0239] <Chemical Formula 3>

[0240] In one embodiment of the present application, the second compound may be represented by the formula 3.

[0241] In one embodiment of the present application, X is a substituted or unsubstituted pyrazine ring; a substituted or unsubstituted quinoxaline ring; or a substituted or unsubstituted pyrrolidine-2,5-dione ring.

[0242] In one embodiment of the present application, X may be a substituted or unsubstituted pyrazine ring.

[0243] In one embodiment of the present application, X may be a substituted or unsubstituted quinoxaline ring. In this case, the position condensed with the thiophene ring may be a pyrazine ring among the quinoxaline rings.

[0244] In one embodiment of the present application, X may be a substituted or unsubstituted pyrrolidine-2,5-dione ring.

[0245] In one embodiment of the present application, the formula 3 may be represented by any one of the following formulas 3-1 to 3-3.

[0246] [Chemical Formula 3-1]

[0247]

[0248] [Chemical Formula 3-2]

[0249]

[0250] [Chemical Formula 3-3]

[0251]

[0252] In the above chemical formulas 3-1 to 3-3,

[0253] M1 to M4 are the same or different from one another, and each independently is hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; or substituted or unsubstituted cycloalkyl group, or substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof,

[0254] Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0255] M5 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0256] The definitions of the remaining substituents are the same as those in Chemical Formula 3 above.

[0257] In one embodiment of the present application, M1 to M4 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof.

[0258] In one embodiment of the present application, M1 to M4 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); C1 to C60 haloalkyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

[0259] In one embodiment of the present application, M1 to M4 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); C1 to C40 haloalkyl group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0260] In one embodiment of the present application, M1 to M4 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); C1 to C30 haloalkyl group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0261] In one embodiment of the present application, M1 to M4 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); C1 to C20 haloalkyl group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; substituted or unsubstituted C2 to C20 heteroaryl group; or a combination thereof.

[0262] In one embodiment of the present application, the formula 3 may be represented by any one of the following formulas 3-1-1 to 3-1-3.

[0263] [Chemical Formula 3-1-1]

[0264]

[0265] [Chemical Formula 3-1-2]

[0266]

[0267] [Chemical Formula 3-1-3]

[0268]

[0269] In the above chemical formulas 3-1-1 to 3-1-3,

[0270] Y3 and Y4 are equal to or different from each other, and each is independently O; S; Se; or N(M17), and

[0271] M1 to M4 are the same or different from one another, and each independently is hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; or substituted or unsubstituted cycloalkyl group, or substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof,

[0272] Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0273] M5 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0274] M11 to M17 are the same or different from one another, and each independently is hydrogen; deuterium; a halogen group; a cyano group; an ester group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted alkoxy group, and

[0275] a and b are each integers from 1 to 4, and when a and b are each 2 or greater, the substituents inside the parentheses are the same or different, and

[0276] The definitions of the remaining substituents are the same as those in Chemical Formula 3 above.

[0277] In one embodiment of the present application, M11 to M17 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0278] In one embodiment of the present application, the M11 to M17 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C1 to C60 alkoxy group.

[0279] In one embodiment of the present application, the M11 to M17 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C1 to C30 alkoxy group.

[0280] In one embodiment of the present application, the M11 to M17 may be the same or different from one another and may each independently be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C15 alkyl group; or a substituted or unsubstituted C1 to C15 alkoxy group.

[0281] In one embodiment of the present application, H1 and H2 of the formulas 2 and 3 may be the same or different from each other and may each be an independently substituted or unsubstituted divalent heteroaryl group.

[0282] In one embodiment of the present application, H1 and H2 may be the same or different from each other and may each be independently substituted or unsubstituted divalent C2 to C60 heteroaryl groups.

[0283] In one embodiment of the present application, H1 and H2 may be the same or different from each other and may each be independently substituted or unsubstituted divalent C2 to C40 heteroaryl groups.

[0284] In one embodiment of the present application, H1 and H2 may be the same or different from each other and may each be independently substituted or unsubstituted divalent C2 to C30 heteroaryl groups.

[0285] In one embodiment of the present application, H1 and H2 are the same or different from each other and may each independently be a substituted or unsubstituted divalent thiophene group; a substituted or unsubstituted divalent furan group; a substituted or unsubstituted divalent pyrrole group; a substituted or unsubstituted divalent selenophene group; a substituted or unsubstituted dihydrothienodioxine group; a substituted or unsubstituted divalent thiazole group; a substituted or unsubstituted divalent thienopyrrole group; a substituted or unsubstituted divalent thienothiazole group; a substituted or unsubstituted divalent thienothiophene group; or a substituted or unsubstituted divalent benzodithiophene group.

[0286] In one embodiment of the present application, H1 and H2 are the same or different from each other and each independently comprises: a divalent thiophene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent furan group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent pyrrole group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent selenophene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent dihydrothienodioxine group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; and a divalent thiazole group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group. It may be a divalent thienopyrrole group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent thienothiazole group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; a divalent thienothiophene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; or a divalent benzodithiophene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group.

[0287] In one embodiment of the present application, H1 and H2 may be the same or different from each other and may each be independently represented by any one of the following chemical formulas H-1 to H-4.

[0288] [Chemical Formula H-1]

[0289]

[0290] [Chemical Formula H-2]

[0291]

[0292] [Chemical Formula H-3]

[0293]

[0294] [Chemical Formula H-4]

[0295]

[0296] In the above chemical formulas H-1 to H-4,

[0297] Y1 and Y2 are the same or different from each other, and each is independently O; S; Se; or N(H19), and

[0298] W1 is N or C(H2O), and

[0299] H11 to H20 are the same or different from one another and are each independently hydrogen; deuterium; a halogen group; a cyano group; an ester 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 heteroaryl group,

[0300] * is the site that combines with other structures in the above chemical formulas 2 and 3.

[0301] In one embodiment of the present application, Y1 and Y2 are the same or different from each other and are each independently O; S; Se; or N(H19), and H19 may be a substituted or unsubstituted alkyl group.

[0302] In one embodiment of the present application, W1 is N or C(H2O), and H2O may be hydrogen; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0303] In one embodiment of the present application, H11 to H18 may be the same or different from one another and may each independently be hydrogen; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.

[0304] In one embodiment of the present application, H1 and H2 may be the same or different from each other and may each be independently selected from the following structures.

[0305]

[0306] In the above structure, H21 to H24 are the same or different from each other and each independently hydrogen; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group, and * is a site that bonds with other structures in the above chemical formulas 2 and 3.

[0307] In one embodiment of the present application, L1 and L2 of the formulas 2 and 3 are the same or different from each other and are each independently directly bonded; -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-; or -OC(=O)-C(R)=C(R')-.

[0308] In one embodiment of the present application, L1 and L2 may be the same or different from each other and may each independently be -O-; -S-; -C(=O)-; -C(=O)O-; -OC(=O)-; -OC(H2)-; -C(H2)O-; -C(R)=C(R')-; -C≡C-; -C(R)=C(R')-C(=O)-; or -C(=O)-C(R)=C(R')-.

[0309] In one embodiment of the present application, L1 and L2 may be directly coupled.

[0310] In one embodiment of the present application, Q1 and Q2 of Formulas 2 and 3 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; Alternatively, it is a substituted or unsubstituted alkoxy group, or Ra and Rb of -N(Ra)(Rb) combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0311] In one embodiment of the present application, Ra and Rb of the -N(Ra)(Rb) may be one of the listed substituents, or may combine with A1 or A2 of Formula 2 or 3 to form a substituted or unsubstituted N-containing ring. When both Q1 and Q2 of Formula 2 or 3 are -N(Ra)(Rb), Q1 and Q2 may each independently combine with or not combine with A1 and A2.

[0312] In one embodiment of the present application, Q1 and Q2 do not include an aromatic structure. By not including an aromatic structure in Q1 and Q2, which are terminal structures in the above formulas 2 and 3, the effect of increasing solubility can be expected.

[0313] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkyne group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C1 to C60 alkyl carbonyl group; a substituted or unsubstituted C1 to C60 alkoxycarbonyl group; a substituted or unsubstituted C1 to C60 alkylcarbonyloxy group; a substituted or unsubstituted C1 to C60 alkoxycarbonyloxy group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; A substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; or a substituted or unsubstituted C1 to C60 alkoxy group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0314] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkyne group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C1 to C40 alkyl carbonyl group; a substituted or unsubstituted C1 to C40 alkoxycarbonyl group; a substituted or unsubstituted C1 to C40 alkylcarbonyloxy group; a substituted or unsubstituted C1 to C40 alkoxycarbonyloxy group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; A substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; or a substituted or unsubstituted C1 to C40 alkoxy group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0315] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkyne group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C1 to C30 alkyl carbonyl group; a substituted or unsubstituted C1 to C30 alkoxycarbonyl group; a substituted or unsubstituted C1 to C30 alkylcarbonyloxy group; a substituted or unsubstituted C1 to C30 alkoxycarbonyloxy group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; A substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; or a substituted or unsubstituted C1 to C30 alkoxy group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0316] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkyne group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C1 to C30 alkyl carbonyl group; a substituted or unsubstituted C1 to C30 alkoxycarbonyl group; a substituted or unsubstituted C1 to C30 alkylcarbonyloxy group; a substituted or unsubstituted C1 to C30 alkoxycarbonyloxy group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; It is a substituted or unsubstituted C1 to C30 alkyl group, or Ra and Rb of -N(Ra)(Rb) can combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0317] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); an alkyl group substituted or unsubstituted with a halogen group; a cycloalkyl group; an alkenyl group; an alkyne group; an alkoxy group; an alkyl carbonyl group; an alkoxycarbonyl group; an alkyl carbonyloxy group; an alkoxycarbonyloxy group; a heterocycloalkyl group; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; an alkyl group substituted or unsubstituted with a halogen group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0318] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); C1 to C30 alkyl groups substituted or unsubstituted with halogen groups; C3 to C30 cycloalkyl groups; C2 to C30 alkenyl groups; C2 to C30 alkyne groups; C1 to C30 alkoxy groups; C1 to C30 alkyl carbonyl groups; C1 to C30 alkoxycarbonyl groups; C1 to C30 alkylcarbonyloxy groups; C1 to C30 alkoxycarbonyloxy groups; C2 to C30 heterocycloalkyl groups; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; The alkyl group may be substituted or unsubstituted with a halogen group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0319] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); C1 to C30 alkyl groups substituted or unsubstituted with halogen groups; C3 to C30 cycloalkyl groups; C2 to C30 alkenyl groups; C2 to C30 alkyne groups; C1 to C30 alkoxy groups; C1 to C30 alkyl carbonyl groups; C1 to C30 alkoxycarbonyl groups; C1 to C30 alkylcarbonyloxy groups; C1 to C30 alkoxycarbonyloxy groups; or a combination thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; or alkyl groups substituted or unsubstituted with halogen groups, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0320] In one embodiment of the present application, Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); C1 to C30 alkyl groups substituted or unsubstituted with halogen groups; cyclohexyl groups; ethenyl groups; ethinyl groups; C1 to C30 alkoxy groups; C1 to C30 alkyl carbonyl groups; C1 to C30 alkoxycarbonyl groups; C1 to C30 alkylcarbonyloxy groups; C1 to C30 alkoxycarbonyloxy groups; morpholine groups; tetrahydropyran groups; dioxane groups; piperazine groups; or combinations thereof, and Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; The alkyl group may be substituted or unsubstituted with a halogen group, or Ra and Rb of -N(Ra)(Rb) may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0321] In one embodiment of the present application, A1 and A2 of the formulas 2 and 3 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or substituted or unsubstituted divalent heteroaryl groups, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0322] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or substituted or unsubstituted divalent heteroaryl groups, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring with A1 and A2, respectively, and the substituted or unsubstituted aryl groups; or substituted or unsubstituted divalent heteroaryl groups may be substituted with one or more -Fs.

[0323] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C60 aryl groups; or substituted or unsubstituted divalent C2 to C60 heteroaryl groups, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0324] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C40 aryl groups; or substituted or unsubstituted divalent C2 to C40 heteroaryl groups, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0325] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C30 aryl groups; or substituted or unsubstituted divalent C2 to C30 heteroaryl groups, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0326] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C30 aryl groups; or substituted or unsubstituted divalent C2 to C30 heteroaryl groups, or Ra and Rb of -N(Ra)(Rb) are combined with A1 and A2, respectively, to form a substituted or unsubstituted N-containing ring, and the substituted or unsubstituted divalent C6 to C30 aryl groups; or substituted or unsubstituted divalent C2 to C30 heteroaryl groups may be substituted with one or more -Fs.

[0327] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent naphthyl group; a substituted or unsubstituted divalent fluorene group; a substituted or unsubstituted divalent thiophene group; or a substituted or unsubstituted divalent thienothiazole group, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0328] In one embodiment of the present application, A1 and A2 are the same or different from each other and are each independently a divalent phenyl group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, a haloalkyl group, and an alkoxy group; a divalent naphthyl group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, a haloalkyl group, and an alkoxy group; a divalent fluorene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, a haloalkyl group, and an alkoxy group; a divalent thiophene group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group; or a divalent thienothiazole group substituted or unsubstituted with a substituent selected from a halogen group, an alkyl group, and an alkoxy group, or are combined with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.

[0329] In one embodiment of the present application, when Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form a substituted or unsubstituted N-containing ring.

[0330] In one embodiment of the present application, when Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form a substituted or unsubstituted N-containing C2 to C60 ring.

[0331] In one embodiment of the present application, when Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form a substituted or unsubstituted N-containing C2 to C40 ring.

[0332] In one embodiment of the present application, when Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form a substituted or unsubstituted N-containing C2 to C30 ring.

[0333] In one embodiment of the present application, where Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form a substituted or unsubstituted N-containing heterocycloalkyl and aryl condensation ring.

[0334] In one embodiment of the present application, when Q1 or Q2 is -N(Ra)(Rb), Ra and Rb may combine with A1 or A2 to form an N-containing heterocycloalkyl and aryl condensation ring that is substituted or unsubstituted with a substituent selected from a halogen group and an alkyl group.

[0335] For example, A1-Q1 and A2-Q2 of the above chemical formulas 2 and 3 may include the following structures, and the following structures may be further substituted according to the definitions above.

[0336]

[0337] In one embodiment of the present application, the chemical formula 2 may be any one of the following compounds.

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350] In one embodiment of the present application, the chemical formula 3 may be any one of the following compounds.

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366] <Chemical Formula 4>

[0367] In one embodiment of the present application, the second compound may be represented by the following chemical formula 4.

[0368] [Chemical Formula 4]

[0369]

[0370] The definition of the substituent of Chemical Formula 4 above is as previously stated.

[0371] In one embodiment of the present application, Y1 may be C(R4).

[0372] In one embodiment of the present application, Y1 may be N.

[0373] In one embodiment of the present application, Y2 may be C(R5).

[0374] In one embodiment of the present application, Y2 may be N.

[0375] In one embodiment of the present application, Y1 is C(R4) and Y2 is C(R5), and R4 and R5 may combine with each other to form a substituted or unsubstituted cyclohexane ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted pyrazine ring.

[0376] In one embodiment of the present application, the formula 4 may be represented by any one of the following formulas 4-1 to 4-3.

[0377] [Chemical Formula 4-1]

[0378]

[0379] [Chemical Formula 4-2]

[0380]

[0381] [Chemical Formula 4-3]

[0382]

[0383] [Chemical Formula 4-4]

[0384]

[0385] [Chemical Formula 4-5]

[0386]

[0387] [Chemical Formula 4-6]

[0388]

[0389] In the above chemical formulas 4-1 to 4-6,

[0390] R6 to R9 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof,

[0391] Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0392] The definition of the remaining substituents is the same as the definition in Chemical Formula 4 above.

[0393] In one embodiment of the present application, the R6 to R9 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

[0394] In one embodiment of the present application, the R6 to R9 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0395] In one embodiment of the present application, L3 and L4 are the same or different from each other and are each independently directly coupled; -O-; -S-; -N=N-; -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-; or -OC(=O)-C(R)=C(R')-.

[0396] In one embodiment of the present application, L3 and L4 may be the same or different from each other and each may be independently directly coupled; -O-; -S-; -N=N-; -C(=O)-; or -C≡C-.

[0397] In one embodiment of the present application, A3 and A4 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or are substituted or unsubstituted divalent heteroaryl groups, and when L5 or L6 is a direct bond, they may form a substituted or unsubstituted N-containing ring by bonding with Ra' and Rb' among the -N(Ra')(Rb') of Q3 and Q4, respectively.

[0398] In one embodiment of the present application, A3 and A4 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or substituted or unsubstituted divalent heteroaryl groups, and when L3 or L4 is a direct bond, they are each bonded to Ra' and Rb' among the -N(Ra')(Rb') of Q3 and Q4 to form a substituted or unsubstituted N-containing ring, and the substituted or unsubstituted divalent aryl groups; or substituted or unsubstituted divalent heteroaryl groups may be substituted with one or more -Fs.

[0399] In one embodiment of the present application, A3 and A4 may be the same or different from each other and each independently substituted or unsubstituted divalent C6 to C60 aryl group; or substituted or unsubstituted divalent C2 to C60 heteroaryl group.

[0400] In one embodiment of the present application, A3 and A4 may be the same or different from each other and each independently substituted or unsubstituted divalent C6 to C40 aryl group; or substituted or unsubstituted divalent C2 to C40 heteroaryl group.

[0401] In one embodiment of the present application, A3 and A4 may be the same or different from each other and each independently substituted or unsubstituted divalent C6 to C30 aryl group; or substituted or unsubstituted divalent C2 to C30 heteroaryl group.

[0402] In one embodiment of the present application, A3 and A4 are the same or different from each other and are each independently substituted or unsubstituted divalent C6 to C30 aryl groups; or substituted or unsubstituted divalent C2 to C30 heteroaryl groups, and the substituted or unsubstituted divalent C6 to C60 aryl groups or substituted or unsubstituted divalent C2 to C30 heteroaryl groups may be substituted with one or more -Fs.

[0403] In one embodiment of the present application, A3 and A4 may be the same or different from each other and may each independently be a substituted or unsubstituted divalent phenyl group; a substituted or unsubstituted divalent thiophene group; a substituted or unsubstituted divalent furan group; a substituted or unsubstituted divalent pyrrole group; a substituted or unsubstituted divalent selenopen group; a substituted or unsubstituted thiazole group; a substituted or unsubstituted dihydrothienodioxine group; a substituted or unsubstituted divalent benzothiadiazole group; a substituted or unsubstituted divalent thienothiazole group; a substituted or unsubstituted divalent thienothiophene group; or a substituted or unsubstituted divalent benzodithiophene group.

[0404] In one embodiment of the present application, A3 and A4 may be the same or different from each other and each independently substituted or unsubstituted divalent phenyl group, or may be selected from the following structures.

[0405]

[0406] In the above structure, H21 to H24 are the same or different from each other and each independently hydrogen; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group, and * is a site that bonds with another structure in the above chemical formula 4.

[0407] In one embodiment of the present application, Q3 and Q4 are the same or different from each other and are each independently -N(Ra')(Rb'); -Si(Ra')(Rb')(Rc'); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a combination thereof, and Ra' to Rc' are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Alternatively, if it is a substituted or unsubstituted alkoxy group, or if Ra' and Rb' of -N(Ra')(Rb') are directly bonded to L5 or L6, they combine with A3 or A4 to form a substituted or unsubstituted N-containing ring.

[0408] In one embodiment of the present application, where Q3 and Q4 are -N(Ra')(Rb') and L5 or L6 is a direct bond, Ra' and Rb' can bond with A3 or A4 to form a substituted or unsubstituted N-containing C2 to C60 ring.

[0409] In one embodiment of the present application, where Q3 and Q4 are -N(Ra')(Rb') and L5 or L6 is a direct bond, Ra' and Rb' can bond with A3 or A4 to form a substituted or unsubstituted N-containing C2 to C40 ring.

[0410] In one embodiment of the present application, where Q3 and Q4 are -N(Ra')(Rb') and L5 or L6 is a direct bond, Ra' and Rb' can bond with A3 or A4 to form a substituted or unsubstituted N-containing C2 to C30 ring.

[0411] In one embodiment of the present application, where Q3 and Q4 are -N(Ra')(Rb') and L5 or L6 is a direct bond, Ra' and Rb' can bond with A3 or A4 to form a substituted or unsubstituted N-containing heterocycloalkyl and aryl condensation ring.

[0412] In one embodiment of the present application, where Q3 and Q4 are -N(Ra')(Rb') and L5 or L6 is a direct bond, Ra' and Rb' may bond with A3 or A4 to form an N-containing heterocycloalkyl and aryl condensation ring that is substituted or unsubstituted with a substituent selected from a halogen group and an alkyl group.

[0413] For example, A3-L5-Q3 and A4-L6-Q4 of the above chemical formula 4 may include the following structures, and the following structures may be further substituted according to the definition above.

[0414]

[0415] In one embodiment of the present application, the chemical formula 4 may be any one of the following compounds.

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424] In one embodiment of the present application, the dichroic dye composition may contain 0.05 to 10 parts by weight of the first compound with respect to 100 parts by weight of the total.

[0425] In one embodiment of the present application, the dichroic dye composition may contain 0.1 to 10 parts by weight of the second compound with respect to 100 parts by weight of the total.

[0426] In one embodiment of the present application, the dichroic dye composition may comprise the first compound and the second compound in a weight ratio of 1:1 to 1:200.

[0427] In one embodiment of the present application, the second compound is represented by any one of the formulas 2 to 4 and may further include a third compound different from the second compound.

[0428] In one embodiment of the present application, the dichroic dye composition may contain 0.1 to 10 parts by weight of the third compound with respect to 100 parts by weight of the total.

[0429] The solubility of the dichroic dye composition 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 is, for example, 100 wt% or less.

[0430] A dichroic dye compound according to one embodiment of the present application has a maximum absorption wavelength within a wavelength range of 550 nm to 750 nm.

[0431] A dichroic dye compound according to one embodiment of the present application has a dichroic ratio (DR) of 8.0 or higher.

[0432] In the present application, the dichroic ratio (DR) is a factor capable of confirming anisotropy, wherein the peak absorbance (A) in the case parallel to the polarization direction with respect to polarized light, e.g., polarized UV. parAbsorption (A) when ) is perpendicular to the polarization direction per Value divided by ) (A par / A per It means ).

[0433] A dichroic dye 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.

[0434]

[0435] Liquid crystal composition

[0436] One embodiment of the present application provides a liquid crystal composition comprising the aforementioned dichroic dye compound and liquid crystal material.

[0437] In one embodiment of the present application, the liquid crystal material is JNC 5011XX, etc., but is not limited thereto.

[0438] In one embodiment of the present application, the liquid crystal composition may additionally include additives commonly used in the art.

[0439] In one embodiment of the present application, the liquid crystal composition may further include a chiral agent.

[0440] 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.

[0441] 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.

[0442] In one embodiment of the present application, the chiral agent may be, for example, a low molecular weight compound with a molecular weight of 1,500 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.

[0443] The application ratio of the chiral agent is selected to achieve a desired d / p 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 0.1 to 10 parts by weight per 100 parts by weight of the liquid crystal material. Specifically, the content of the chiral agent may be 0.1 to 7 parts by weight, or 0.1 to 5 parts by weight, per 100 parts by weight of the liquid crystal material.

[0444]

[0445] liquid crystal cell

[0446] 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.

[0447] 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.

[0448] 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).

[0449] 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.

[0450] A liquid crystal cell according to one embodiment of the present application may utilize known techniques in addition to comprising a liquid crystal layer containing the liquid crystal composition described above.

[0451] 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.

[0452] In one embodiment of the present application, the first substrate and the second substrate may be polymer films.

[0453] 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.

[0454] 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.

[0455] 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.

[0456] 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.

[0457] 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.

[0458] 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.

[0459] In one embodiment of the present application, the thickness of the liquid crystal layer may be 0.05㎛ or more, 0.1㎛ or more, 0.5㎛ or more, 1㎛ or more, 1.5㎛ or more, 2㎛ or more, 2.5㎛ or more, 3㎛ or more, 3.5㎛ or more, 4㎛ or more, 4.5㎛ or more, 5㎛ or more, 5.5㎛ or more, 6㎛ or more, 6.5㎛ or more, 7㎛ or more, 7.5㎛ or more, or 8㎛ or more, and may be 25㎛ or less, 20㎛ or less, or 15㎛ or less.

[0460] 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.

[0461] 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°.

[0462] 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°.

[0463] 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.

[0464] 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.

[0465]

[0466] Liquid crystal display

[0467] Another embodiment of the present application provides a liquid crystal display device comprising the liquid crystal cell described above.

[0468] 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.

[0469]

[0470] Preparation of Dichroic Dye Compounds

[0471] Preparation Example 1: Preparation of Compound 1

[0472]

[0473] The above compound 1 was synthesized according to JACS, 1965, 87, 7, 1483.

[0474] MS: [M+H] + = 670.34

[0475] λ max : 779nm, ε: 0.38 (10 -5 M in Toluene)

[0476]

[0477] Preparation Example 2: Preparation of Compound 2

[0478]

[0479] The above compound 2 was synthesized according to Molecular Crystals and Liquid Crystals (1980), 56(8), 249-55.

[0480] MS: [M+H] + = 670.34

[0481] λmax : 851nm, ε: 0.39 (10 -5 M in Toluene)

[0482]

[0483] Preparation Example 3: Preparation of Compound 3

[0484]

[0485] The purchased compound 3 (Hayashibara Ltd., NKX-1199) was recrystallized using toluene and hexane and used.

[0486] MS: [M+H] + = 818.00

[0487] λ max : 915nm, ε:0.33 (10 -5 M in Toluene)

[0488]

[0489] Preparation Example 4: Preparation of Compound 4

[0490] Compound 4 was synthesized through the following reaction.

[0491] (1) Preparation of intermediate 4-1

[0492]

[0493] 27 g (0.1 mol) of 4,4-Dimethoxybenzil CAS: 1226-42-2), 150 ml of AcOH, and 15 ml of 48% HBr were added to a 500 ml round-bottom flask and refluxed for 5 hours. After the reaction was complete, 300 ml of water was added. The mixture was stirred at room temperature for 1 hour, and 14.4 g of intermediate 4-1 was obtained by filtration and drying.

[0494] (2) Preparation of intermediate 4-2

[0495]

[0496] 14.4 g of the above-mentioned intermediate 4-1, 18 g (2.2 eq) of K2CO3, 26.5 g (2.5 eq) of 3-bromoheptane, and 150 ml of DMF were added to a 500 ml round-bottom flask and stirred at 80 °C for 12 hours. After the reaction was complete, 300 ml of H2O and 300 ml of hexane were added and stirred; after phase separation and complete removal of the solvent, intermediate 4-2 was obtained.

[0497] (3) Preparation of Compound 4

[0498]

[0499] The intermediate 4-2 obtained above, 150 ml of 1,4-Dioxane, and 40 g (3 eq) of P2S5 were added to a 500 ml round-bottom flask and refluxed for 6 hours. After cooling to room temperature, 7 g (0.5 eq) of NiCl2·6H2O and 72 ml of H2O were added to the filtered filtrate, and the mixture was refluxed for 12 hours. After cooling to room temperature, the mixture was stirred for 1 hour to obtain a solid. After filtration, the solid was dried using an 80°C vacuum oven to obtain 4.5 g of Compound 4 (yield 15%).

[0500] MS: [M+H] + = 998.40

[0501] λ max : 950nm, ε:0.37 (10 -5 M in Toluene)

[0502]

[0503] Preparation Example 5: Preparation of Compound 5

[0504] Compound 5 was synthesized through the following reaction.

[0505] (1) Preparation of intermediate 5-1

[0506]

[0507] Intermediate 5-1 was obtained in the same manner as the preparation of intermediate 4-2, except that 3-(bromomethyl)heptane was used instead of 3-bromoheptane in the preparation of intermediate 4-2.

[0508] (2) Preparation of Compound 5

[0509]

[0510] 0.4 g of compound 5 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 5-1 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 10%)

[0511] MS: [M+H] + = 1054.46

[0512] λ max : 939nm, ε:0.35 (10 -5 M in Toluene)

[0513]

[0514] Preparation Example 6: Preparation of Compound 6

[0515] Compound 6 was synthesized through the following reaction.

[0516] (1) Preparation of intermediate 6-1

[0517]

[0518] 50 g (2 eq) 4-(heptan-3-yloxy)-3-methoxybenzaldehyde, 2 g (0.05 eq) NaOH, 75 ml EtOH, and 75 ml H2O were added to a 500 ml round-bottom flask and refluxed for 1 hour. After the reaction was complete, the EtOH was removed by vacuum distillation. After adding 300 ml of ethylene acetate to separate layers and remove the solvent, 6-19 g of intermediate (eluent: hexane:THF = 5:1) was obtained through silica gel column purification.

[0519] (2) Preparation of intermediate 6-2

[0520]

[0521] 9 g of the above-mentioned intermediate 6-1, 1.8 g (20 w%) of CuBr2, and 90 ml of DMSO were added to a 500 ml round-bottom flask and stirred at 90 ℃ for 12 hours. After the reaction was complete, 270 ml of H2O and 270 ml of hexane were added and stirred, followed by phase separation and vacuum distillation to obtain intermediate 6-2.

[0522] (3) Preparation of Compound 6

[0523]

[0524] 0.6 g of compound 6 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 6-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 12%)

[0525] MS: [M+H] + = 1118.44

[0526] λ max : 962nm, ε:0.28 (10 -5 M in Toluene)

[0527]

[0528] Preparation Example 7: Preparation of Compound 7

[0529] Compound 7 was synthesized through the following reaction.

[0530] (1) Preparation of intermediate 7-1

[0531]

[0532] 10.1 g (0.1 mol) of benzaldehyde, 25 g (1 eq) of 4-(heptan-3-yloxy)-3-methoxybenzaldehyde, 2 g (0.05 eq) of NaOH, 75 ml of EtOH, and 75 ml of H2O were added to a 500 ml round-bottom flask and refluxed for 1 hour. After the reaction was complete, the EtOH was removed by vacuum distillation. After adding 300 ml of ethylene acetate to separate layers and remove the solvent, 7-19 g of intermediate (eluent: hexane:THF = 5:1) was obtained through silica gel column purification.

[0533] (2) Preparation of intermediate 7-2

[0534]

[0535] 0.6g of intermediate 7-2 was obtained by the same method as the preparation of intermediate 6-2, except that intermediate 7-1 was used instead of intermediate 6-1 in the preparation of intermediate 6-2.

[0536] (3) Preparation of Compound 7

[0537]

[0538] 1.7 g of compound 7 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 7-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 16%)

[0539] MS: [M+H] + = 830.21

[0540] λ max : 922nm, ε:0.34 (10 -5 M in Toluene)

[0541]

[0542] Preparation Example 8: Preparation of Compound 8

[0543] Compound 8 was synthesized through the following reaction.

[0544] (1) Preparation of intermediate 8-1

[0545]

[0546] 7.1 g of intermediate 8-1 was obtained by the same method as the preparation of intermediate 7-1, except that 4-((2-ethylhexyl)oxy)benzaldehyde was used instead of 4-(heptan-3-yloxy)-3-methoxybenzaldehyde in the preparation of intermediate 7-1.

[0547] (2) Preparation of intermediate 8-2

[0548]

[0549] Formula 8-2 was obtained in the same manner as in the preparation of intermediate -2, except that intermediate 8-1 was used instead of intermediate 6-1 in the preparation of intermediate 6-2.

[0550] (3) Preparation of Compound 8

[0551]

[0552] 0.4 g of compound 8 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 8-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 12%)

[0553] MS: [M+H] + = 858.24

[0554] λ max : 930nm, ε:0.36 (10 -5 M in Toluene)

[0555]

[0556] Preparation Example 9: Preparation of Compound 9

[0557] Compound 9 was synthesized through the following reaction.

[0558] (1) Preparation of intermediate 9-1

[0559]

[0560] 7.1 g of intermediate 9-1 was obtained by the same method as the preparation of intermediate 8-1, except that o-tolualdehyde was used instead of benzaldehyde in the preparation of intermediate 8-1.

[0561] (2) Preparation of intermediate 9-2

[0562]

[0563] Intermediate 9-2 was obtained in the same manner as the preparation of intermediate 6-2, except that intermediate 9-1 was used instead of intermediate 6-1 in the preparation of intermediate -2.

[0564] (3) Preparation of Compound 9

[0565]

[0566] 0.4 g of compound 9 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 9-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 12%)

[0567] MS: [M+H] + = 826.25

[0568] λ max : 919nm, ε:0.35 (10 -5 M in Toluene)

[0569]

[0570] Preparation Example 10: Preparation of Compound 10

[0571] Compound 10 was synthesized through the following reaction.

[0572] (1) Preparation of intermediate 10-1

[0573]

[0574] 7.9 g of intermediate 10-1 was obtained by the same method as the preparation of intermediate 7-1, except that 2-chlorobenzaldehyde was used instead of benzaldehyde in the preparation of intermediate 7-1.

[0575] (2) Preparation of intermediate 10-2

[0576]

[0577] 0.8 g of intermediate 10-2 was obtained by the same method as the preparation of intermediate 6-2, except that intermediate 10-1 was used instead of intermediate 6-1 in the preparation of intermediate 6-2.

[0578] (3) Preparation of Compound 10

[0579]

[0580] 2.0 g of compound 10 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 10-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 18%)

[0581] MS: [M+H] + = 898.13

[0582] λ max : 950nm, ε:0.26 (10 -5 M in Toluene)

[0583]

[0584] Preparation Example 11: Preparation of Compound 11

[0585] Compound 11 was synthesized through the following reaction.

[0586] (1) Preparation of intermediate 11-1

[0587]

[0588] 7.5 g of intermediate 11-1 was obtained by the same method as the preparation of intermediate 10-1, except that 3,4-diisobutoxybenzaldehyde was used instead of (heptan-3-yloxy)-3-methoxybenzaldehyde in the preparation of intermediate 10-1.

[0589] (2) Preparation of intermediate 11-2

[0590]

[0591] 0.9 g of intermediate 11-2 was obtained by the same method as the preparation of intermediate 6-2, except that intermediate 11-1 was used instead of intermediate 6-1 in the preparation of intermediate 6-2.

[0592] (3) Preparation of Compound 11

[0593]

[0594] 1.9 g of compound 11 was obtained by the same method as in the preparation of intermediate 4-3, except that intermediate 11-2 was used instead of intermediate 4-2 in the preparation of intermediate 4-3. (Yield 17%)

[0595] MS: [M+H] + = 898.13

[0596] λ max : 894nm, ε:0.27 (10 -5 M in Toluene)

[0597]

[0598] Preparation of a Dichroic Dye Composition

[0599] Comparative Example 1.

[0600] The liquid crystal base mixture of Comparative Example 1 is prepared by mixing 1.30% of the following compound A, 2.60% of compound B, 2.40% of compound C, 0.20% of compound D, and 93.50% of a liquid crystal mixture (B-25 Bayi).

[0601]

[0602] Comparative Example 2.

[0603] The liquid crystal base mixture of Comparative Example 2 is prepared by mixing 1.30% of the following E compound E, 2.30% of the following F compound F, 1.50% of the following G compound, 1.90% of the following H compound, and 93.00% of the liquid crystal mixture (B-25 Bayi).

[0604]

[0605] Comparative Example 3.

[0606] The liquid crystal base mixture of Comparative Example 3 is prepared by mixing the same amount of Compound A, Compound B, Compound C, and Compound D as the mixture of Comparative Example 1 with 0.5% of the following Compound I and 93.00% of the liquid crystal mixture (B-25 Bayi).

[0607]

[0608] Comparative Example 4.

[0609] The liquid crystal base mixture of Comparative Example 4 is prepared by mixing the same amount of compounds E, F, G, and H as the mixture of Comparative Example 2, 0.5% of the following compounds J, and 92.50% of a liquid crystal mixture (B-25 Bayi).

[0610]

[0611] Example 1.

[0612] The liquid crystal base mixture of Example 1 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 1 of the above preparation example is used instead of Compound I.

[0613]

[0614] Example 2.

[0615] The liquid crystal base mixture of Example 2 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 2 of the above preparation example is used instead of Compound I.

[0616]

[0617] Example 3.

[0618] The liquid crystal base mixture of Example 3 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 3 of the above preparation example is used instead of Compound I.

[0619]

[0620] Example 4.

[0621] The liquid crystal base mixture of Example 4 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 4 of the above preparation example is used instead of Compound I.

[0622]

[0623] Example 5.

[0624] The liquid crystal base mixture of Example 5 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 5 of the above preparation example is used instead of Compound I.

[0625]

[0626] Example 6.

[0627] The liquid crystal base mixture of Example 6 is prepared in the same way as the mixture of Comparative Example 3, except that Compound 6 of the above preparation example is used instead of Compound I.

[0628]

[0629] Example 7.

[0630] The liquid crystal base mixture of Example 7 is prepared in the same way as the mixture of Comparative Example 4, except that Compound 7 of the above preparation example is used instead of Compound J.

[0631]

[0632] Example 8.

[0633] The liquid crystal base mixture of Example 8 is prepared in the same way as the mixture of Comparative Example 4, except that Compound 8 of the above preparation example is used instead of Compound J.

[0634]

[0635] Example 9.

[0636] The liquid crystal base mixture of Example 9 is prepared in the same way as the mixture of Comparative Example 4, except that Compound 9 of the above preparation example is used instead of Compound J.

[0637]

[0638] Example 10.

[0639] The liquid crystal base mixture of Example 10 is prepared in the same way as the mixture of Comparative Example 4, except that Compound 10 of the above preparation example is used instead of Compound J.

[0640]

[0641] Example 11.

[0642] The liquid crystal base mixture of Example 11 is prepared in the same way as the mixture of Comparative Example 4, except that Compound 11 of the above preparation example is used instead of Compound J.

[0643]

[0644] <Experimental Example>

[0645] The physical properties of the dichroic dye compositions obtained in the above examples and comparative examples were measured by the following method, and the results are shown in Table 1.

[0646] The mixture obtained from the above examples and comparative examples was filtered through a 0.2 µm PP filter, injected into a prepared glass cell, and the injection port was sealed to fabricate an evaluation liquid crystal film cell. After mounting the corresponding sample on a HunterLAB customized VISTA, L* at 0V and 48V 초기 , a* 초기 , b* 초기 Measure the value, and after 1,000 hours of exposure to the Atlas Ci5000 weathering tester under PV3929 conditions, L* 신뢰성후 , a* 신뢰성후 , b* 신뢰성후 By measuring the value, △E*=((L* 신뢰성후 -L* 초기 )^2+(a* 신뢰성후 -a* 초기 )^2+(b* 신뢰성후 -b* 초기 The value of △E* was calculated using the mathematical formula defined as )^2)^(1 / 2).

[0647] The smaller the △E* value listed in Table 1 below, the less the color change, and the better the reliability can be evaluated.

[0648] Chemical Formula 1 Chemical Formula 2 Chemical Formula 3 Chemical Formula 4 △E*(0V) △E*(48V) Example 1 Compound 1 Compound A Compound B Compound C Compound D3.0 5.3 Example 2 Compound 2 Compound A Compound B Compound C Compound D2.4 4.5 Example 3 Compound 3 Compound A Compound B Compound C Compound D3.2 4.9 Example 4 Compound 4 Compound A Compound B Compound C Compound D2.3 4.3 Example 5 Compound 5 Compound A Compound B Compound C Compound D2.4 5.0 Example 6 Compound 6 Compound A Compound B Compound C Compound D1.9 3.9 Example 7 Compound 7 Compound E Compound F Compound Compound G H-0.7 1.7 Example 8 Compound 8 Compound E Compound F Compound G Compound H-0.8 1.7 Example 9 Compound 9 Compound E Compound F Compound G Compound H-1.0 2.1 Example 10 Compound 10 Compound E Compound F Compound G Compound H-0.6 1.5 Example 11 Compound 11 Compound E Compound F Compound G Compound H-1.4 3.2 Comparative Example 1 - Compound A Compound B Compound C Compound D 5.5 7.6 Comparative Example 2 - Compound E Compound F Compound G Compound H-4.6 5.0 Comparative Example 3 - Compound A Compound B Compound C Compound D Compound I 4.2 4.7 Comparative Example 4 - Compound E compound F compound G compound H compound J3.35.0

[0649] According to Table 1 above, Examples 1 to 11, which used a dichroic dye composition comprising both the first compound represented by Chemical Formula 1 and the second compound represented by any one of Chemical Formulas 2 to 4, showed excellent reliability with less color change compared to Comparative Examples 1 to 4, which used only the second compound represented by any one of Chemical Formulas 2 to 4.

[0650] In addition, a dichroic dye composition containing only the first compound has a maximum absorption wavelength (λ max ) is located in the near-infrared (NIR) region and does not exhibit significant color in the visible light region. As a result, no color was produced, and it was difficult to reliably measure the △E* value.

Claims

1. A first compound represented by the following chemical formula 1; and A dichroic dye composition comprising a second compound represented by any one of the following chemical formulas 2 to 4: [Chemical Formula 1] In the above chemical formula 1, V1 to V4 are the same or different from one another, and each is an independently substituted or unsubstituted divalent aryl group; or a substituted or unsubstituted divalent heteroaryl group, and U1 to U4 are the same or different from one another 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')-; -NH-C(=O)-; -C(=O)-NH-; or -N=N-, and P1 to P4 are the same or different from one another and each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof, wherein K3 and K4 of -N(K3)(K4) combine with V1, V2, V3, or V4 to form a substituted or unsubstituted N-containing ring, and K1 to K7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted alkoxy group, and n1 to n4 are each 0 or 1, and m1 to m4 are each integers from 1 to 5, and if m1 to m4 are each 2 or greater, the structures inside the parentheses are the same or different from each other, [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, X is a substituted or unsubstituted pyrazine ring; a substituted or unsubstituted quinoxaline ring; or a substituted or unsubstituted pyrrolidine-2,5-dione ring, and Z1 and Z2 are equal to or different from each other, and each is independently -C(R3)-; or -N-, and If both Z1 and Z2 are -C-(R3), R3 is the same or different, and R1 to R3 are the same or different from one another, and each independently is hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, or combines with an adjacent group to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted pyrazine ring, and Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and H1 and H2 are identical or different from each other and are each independently substituted or unsubstituted divalent heterocyclic rings, and L1 and L2 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-; or -OC(=O)-C(R)=C(R')- and, L3 to L6 are the same or different from one another and are each independently directly coupled; -O-; -S-; -N=N-; -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-; or -OC(=O)-C(R)=C(R')- and, Y1 is N; or C(R4), and Y2 is N; or C(R5), and R4 and R5 are the same or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; nitro group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, or combined with each other to form a substituted or unsubstituted cyclohexane ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted pyrazine ring, and Q1 and Q2 are the same or different from each other and are each independently -N(Ra)(Rb); -Si(Ra)(Rb)(Rc); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted heterocycloalkyl group; or a combination thereof, Ra to Rc are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted alkoxy group, and Ra and Rb of -N(Ra)(Rb) combine with A1 or A2 to form a substituted or unsubstituted N-containing ring, and A1 and A2 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or are substituted or unsubstituted divalent heteroaryl groups, or each combine with Ra and Rb among the -N(Ra)(Rb) of Q1 and Q2 to form a substituted or unsubstituted N-containing ring, and o1 and o2 are each integers from 0 to 3, and if each is 2 or greater, the structure inside the parentheses is the same or different, and Q3 and Q4 are the same or different from each other and are each independently -N(Ra')(Rb'); -Si(Ra')(Rb')(Rc'); a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted alkyne group; a substituted or unsubstituted alkyl carbonyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted alkoxycarbonyl group; a substituted or unsubstituted alkylcarbonyloxy group; a substituted or unsubstituted alkoxycarbonyloxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted aryloxy group; or a combination thereof, Ra' to Rc' are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkoxy group, and Ra' and Rb' of -N(Ra')(Rb') combine with A3 or A4 to form a substituted or unsubstituted N-containing ring when L5 or L6 is a direct bond, and A3 and A4 are the same or different from each other and are each independently substituted or unsubstituted divalent aryl groups; or are substituted or unsubstituted divalent heteroaryl groups, and where L3 or L4 is a direct bond, they each bond with Ra' and Rb' among the -N(Ra')(Rb') of Q3 and Q4 to form a substituted or unsubstituted N-containing ring, and In the above chemical formulas 1 to 4, R and R' are the same or different from each other and are each independently hydrogen; deuterium; 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 heteroaryl group.

2. In Claim 1, A dichroic dye composition in which the second compound is represented by the chemical formula 2 or 3.

3. In Claim 1, The above second compound is a dichroic dye composition represented by the above chemical formula 4.

4. A dichroic dye composition according to Claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, E1 to E4 are the same or different from each other, and each is independently O; S; or N, and O1 to O8 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; carboxyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; substituted or unsubstituted ester group; substituted or unsubstituted amide group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkyne group; -O(K1); -S(K2); -N(K3)(K4); -Si(K5)(K6)(K7); or a combination thereof, K1 to K7 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a substituted or unsubstituted alkoxy group, and The definitions of the remaining substituents are the same as the definitions in Chemical Formula 1 above.

5. A dichroic dye composition according to Claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-8: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] In the above chemical formulas 2-1 to 2-8, R11 to R18 are the same or different from one another and are each independently hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and The definitions of the remaining substituents are the same as the definitions in Chemical Formula 2 above.

6. A dichroic dye composition according to Claim 1, wherein the formula 3 is represented by any one of the following formulas 3-1 to 3-3: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] In the above chemical formulas 3-1 to 3-3, M1 to M4 are the same or different from one another, and each independently is hydrogen; deuterium; halogen group; cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); haloalkyl group; substituted or unsubstituted alkyl group; or substituted or unsubstituted cycloalkyl group, or substituted or unsubstituted aryl group; substituted or unsubstituted heteroaryl group; or a combination thereof, Rd, Re and Rf are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and M5 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and The definitions of the remaining substituents are the same as those in Chemical Formula 3 above.

7. A dichroic dye composition according to claim 1, wherein the second compound is represented by any one of formulas 2 to 4, and further comprises a third compound different from the second compound.

8. A dichroic dye composition according to claim 1, wherein the first compound is any one of the following compounds: .

9. A dichroic dye composition according to Claim 1, wherein Chemical Formula 2 is any one of the following compounds: .

10. A dichroic dye composition according to Claim 1, wherein Chemical Formula 3 is any one of the following compounds: .

11. A dichroic dye composition according to Claim 1, wherein Chemical Formula 4 is any one of the following compounds: .

12. A dichroic dye composition according to any one of claims 1 to 11; and a liquid crystal composition comprising a liquid crystal material.

13. A liquid crystal composition according to claim 12, further comprising a chiral agent.

14. 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 12.

15. A liquid crystal display device comprising a liquid crystal cell according to claim 14.

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