KR-20260067324-A - DICHROIC DYE COMPOUND, LIQUID CRYSTAL COMPOSITION, LIQUID CRYSTAL CELL, AND LIQUID CRYSTAL DISPLAY DEVICE

KR20260067324AKR 20260067324 AKR20260067324 AKR 20260067324AKR-20260067324-A

Abstract

The present application relates to a dichroic dye compound represented by Chemical Formula 1, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device according to one embodiment of the present application.

Inventors

문상필
윤소라
이호용
레두이 히에유
김지선
이예원
장한빛
정동민
황병희
황승연
김진홍

Assignees

주식회사 엘지화학

Dates

Publication Date: 20260512
Application Date: 20251028
Priority Date: 20241105

Claims (9)

Dichroic dye compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X and Z are equal to or different from each other, and each independently is C(R3); or N, If X and Z are both 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; a halogen group; a cyano group; -O(Rd); -S(Re); -C(=O)O(Rf); a haloalkyl group; 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 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(F 2 )O-; -OC(F 2 )-; -C(=O)O-; -OC(=O)-; -OC(H 2 )-; -C(H 2 )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, R and R' are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and Q1 and Q2 are the same or different from each other and are each independently hydrogen; deuterium; -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 alkynyl 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, At least one of Q1 and Q2 is -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 alkynyl 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 of two or fewer rings, or each combine with Ra and Rb of -N(Ra)(Rb) to form a substituted or unsubstituted N-containing ring.
A dichroic dye compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-8: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] In the above chemical formulas 1-1 to 1-8, 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 1 above.
A dichroic dye compound according to claim 1, wherein H1 and H2 are the same or different from each other and each independently represented by any one of the following chemical formulas H-1 to H-4: [Chemical Formula H-1] [Chemical Formula H-2] [Chemical Formula H-3] [Chemical Formula H-4] In the above chemical formulas H-1 to H-4, Y1 and Y2 are the same or different from each other, and each is independently O; S; Se; or N(H19), and W1 is N or C(H2O), and 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, * is the site that combines with another structure in the above chemical formula 1.
A dichroic dye compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 9: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] In the above chemical formulas 2 to 9, Y3 and Y4 are equal to or different from each other, and each is independently O; S; Se; or N(R27), and 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 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 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 The definitions of the remaining substituents are the same as the definitions in Chemical Formula 1 above.
A dichroic dye compound according to claim 1, wherein the dichroic dye compound is any one of the following compounds: .
A liquid crystal composition comprising a dichroic dye compound according to any one of claims 1 to 5; and a liquid crystal material.
A liquid crystal composition according to claim 6, further comprising a chiral agent.
A liquid crystal cell comprising a first substrate; a liquid crystal layer; and a second substrate, The liquid crystal layer is a liquid crystal cell comprising a liquid crystal composition according to claim 6.
A liquid crystal display device comprising a liquid crystal cell according to claim 8.

Description

Dichroic dye compound, liquid crystal composition, liquid crystal cell, and liquid crystal display device The present application relates to a dichroic dye compound, a liquid crystal composition, a liquid crystal cell, and a liquid crystal display device. This application claims the benefit of the filing date of Korean Patent Application No. 10-2024-0155283 filed with the Korean Intellectual Property Office on November 5, 2024, the entire contents of which are incorporated herein. Liquid crystals are used as dielectrics, particularly in display devices, whereby the optical properties of the material may be affected by the applied voltage. In a guest-host system, the liquid crystal medium comprises one or more dichroic dyes in addition to the liquid crystal. Due to a direct dependence on light absorption by the dye molecules, the transmittance of the dye-doped liquid crystal to light can be controlled when the dye molecules change their alignment with the liquid crystal. 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. 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. FIG. 1 is a diagram illustrating the structure of a liquid crystal cell according to one embodiment of the present application. The present application will be described in more detail below. 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. Examples of substituents in this specification are described below, but are not limited thereto. 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. In this specification, the term “substituted or unsubstituted” means one or more substituents selected from the group consisting of halogen groups; cyano groups; hydroxyl groups; oxygen (=O); amine groups; nitro groups; silyl groups; ester groups; sulfide groups; alkyl groups; haloalkyl groups; alkenyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; alkyl carbonyl groups; alkoxycarbonyl groups; aryl groups; and heterocyclic groups, or two or more of the exemplified substituents are connected to a substituent, or have no substituents. In this specification, hydrogen includes all of hydrogen; deuterium; and tritium. In this specification, the halogen group is fluorine, chlorine, bromine, or iodine. In this specification, the amine group may be represented as -NR 101 R 102 , where R 101 and R 102 are each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group. The number of carbon atoms in the amine group is not particularly limited, but is preferably 0 to 30. In this specification, the silyl group may be represented as -SiR 103 R 104 R 105 , where R 103 , R 104 , and R 105 are each independently hydrogen, deuterium, an alkyl group, an alkenyl group, an aryl group, or a heterocyclic group. Specific examples include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, etc. In this specification, the ester group is represented as -C(=O)OR 106 or -OC(=O)R 106 , wherein R 106 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. In this specification, the sulfide group is represented as -SR 107 , wherein R 107 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. In