Organic compound and use thereof

Abstract

The present invention provides an organic compound and a use thereof. The molecular structure of the organic compound comprises a chromophore and a chiral group connected to the chromophore by means of a chemical bond. In the present invention, the organic compound serving as a chiral dichroic dye has an order parameter higher than a conventional chiral agent, a high dichroic ratio value, high solubility, high absorbance, and a suitable spiral twisting force constant. The organic compound has chirality, and can partially or completely replace a chiral agent, and reduce the cost of the chiral agent.

Description

An organic compound and its application

[0001] This application claims priority to a Chinese patent application filed on February 28, 2024, with application number 202410220355.5 and invention name “An organic compound and its application,” the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention belongs to the technical field of liquid crystal materials, and in particular relates to an organic compound and application thereof. Background Art

[0003] Liquid crystal materials are liquid crystal materials that exist between solid and liquid phases. Their phases can be broadly categorized as nematic, smectic, and cholesteric. Based on their operating modes, they can be classified into dynamic scattering (DS), guest-host (GH), twisted nematic (TN), super twisted nematic (STN), and vertical alignment (VA).

[0004] Liquid crystal elements are made by clamping liquid crystal materials (liquid crystal compositions) between two electrodes. Due to their special electro-optical properties, they are widely used in display devices and dimming devices. Display devices include electronic calculators, various test instruments, automobile dashboards, computers, laptops, mobile phones, televisions, etc., and dimming devices include 3D glasses, automobile rearview mirrors, architectural glass, welding light valves, camera viewfinders, etc.

[0005] With the rapid development of liquid crystal technology, dichroic dyes have also received increasing attention in this field. For example, most liquid crystal elements require the use of a linear polarizer to obtain polarized light, resulting in low light utilization efficiency. However, by adding a dichroic dye to a dye liquid crystal composition (i.e., a guest-host liquid crystal composition), the dichroic property of the dichroic dye (i.e., different absorbance for polarized light perpendicular to and parallel to the absorption axis of the dichroic dye molecule, also known as absorption anisotropy) is utilized. This allows liquid crystal elements using guest-host liquid crystal compositions to achieve monochrome or multicolor displays with little or no use of a polarizer, resulting in high brightness and display contrast, wide viewing angle, and the ability to eliminate color aberration. In particular, in reflective mode liquid crystal elements without a backlight, luminous displays can be achieved with high light utilization efficiency.

[0006] Current liquid crystal dimming technologies include multilayer dimming technology using liquid crystal compositions containing dichroic dyes as switching layers; guest-host liquid crystal compositions (comprising dichroic dyes and nematic matrix liquid crystals) that directly achieve dimming by utilizing the absorption dichroism of the dichroic dyes; polymer-dispersed liquid crystals (PDLCs), which combine nematic liquid crystals with molecular polymers and manipulate the arrangement of the nematic liquid crystals to create different refractive indices, resulting in a macroscopic state transition between light transmission and light dispersion for dimming; and polymer-stabilized cholesteric liquid crystals (PSCTs), which utilize the bistability of cholesteric liquid crystal compositions to achieve dimming, and add bimesogenic compounds to achieve three-state dimming: transparent, shielded, and highly transparent states. These dimming technologies all utilize dye-based liquid crystal compositions (i.e., guest-host liquid crystal compositions) with dichroic dyes, leveraging the absorption dichroism of the dichroic dyes to achieve a wider range of transmittance modulation.

[0007] For guest-host liquid crystal compositions containing dichroic dyes, the better and more uniform the guest-host liquid crystal composition's light absorption within the absorption band, the more uniform the transmittance curve distribution, and the better the black effect displayed by the display device. Therefore, the dichroic dye must have good and uniform absorption within the absorption band, and also high solubility in the liquid crystal composition. In guest-host liquid crystal compositions, transmittance and the solubility of the dichroic dye in the liquid crystal significantly affect the display quality of the guest-host display device, in terms of contrast and color reproduction. While increasing the concentration of the dichroic dye can improve contrast, this compromises the luminescent display characteristic of guest-host displays. Therefore, it is crucial that the dichroic dye maintains two properties with the parent liquid crystal: low transmittance (high contrast) and high solubility.

[0008] Currently, a wide variety of dichroic dyes have been discovered that can provide high color intensity, high saturation, and a good dichroic ratio for use in liquid crystals. However, most existing dichroic dyes lack chirality and often require use with chiral agents, and they also have low solubility.

[0009] Therefore, developing a dichroic dye with high dichroic ratio, high solubility and high absorbance, without the need to add a chiral agent or with a reduced chiral agent content, and capable of being better used with liquid crystals, is an urgent problem to be solved in this field.

[0010] Summary of the Invention

[0011] In response to the shortcomings of the prior art, the present invention provides an organic compound, a liquid crystal composition, and a liquid crystal device containing the same. The organic compound, as a chiral dichroic dye, has an order parameter higher than that of conventional chiral agents, a high dichroic ratio, high solubility, high absorbance, and a suitable helical twisting force constant (HTP value). Furthermore, the organic compound possesses chirality and can partially or completely replace the use of chiral agents in liquid crystal materials, thereby reducing the cost of chiral agents.

[0012] To achieve this object, the present invention adopts the following technical solutions:

[0013] In a first aspect, the present invention provides an organic compound, wherein the molecular structure of the organic compound includes a chromophore and a chiral group connected to the chromophore via a chemical bond.

[0014] In the present invention, the organic compound introduces a chiral group into the molecular chain of the chromophore through a specific molecular structure design, providing a chiral effect. At the same time, its branched structure can increase the solubility of the chromophore itself, especially for chromophores containing rigid structures, and can effectively improve the solubility of dyes with rigid structures; as a chiral dichroic dye, it is used in a liquid crystal composition, which can not only improve the solubility of the dye in the liquid crystal composition, but also reduce the use of chiral agents, and even eliminate the need to add chiral agents, thereby reducing costs and avoiding the problem of low solubility caused by chiral agents. At the same time, the organic compound has an order parameter higher than that of conventional chiral agents, a high dichroic ratio, high absorbance and a wide range of helical twisting force constants, and can be applied to different functional scenarios and has a wide range of applications.

[0015] Preferably, the organic compound has a structure shown in Formula I:

[0016] wherein A is selected from a chromophore.

[0017] Z is selected from a single bond, -O-, -S-, -NR N1 -、-NR N2 -CR C1 -, -O-CO-, -CO-O-, -CO-O-CR C1 R C2 -、-CR C3 R C4 -, -C=N-, -N=C-, -C≡C-, -CR C5 =CR C6 -、-CO-、-O-CR C7 R C8 -、-CR C9 R C10 Any one of -O-, -SO- or -SO2-.

[0018] R1, R2, and R3 are each independently selected from any one of H, -C≡CH, a C1-C10 straight-chain or branched alkyl group, a C6-C12 aryl group, or a cholesterol ester group, and R1, R2, and R3 are each different.

[0019] n is selected from integers ≥ 1, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, etc.; and when n is greater than 1, the chiral groups may be the same or different.

[0020] In the present invention, in the structure shown in Formula I, A represents a chromophore, Z represents a chemical bond, represents a chiral group connected to A through Z, n represents the number of chiral groups connected to A, and the chiral groups connected to A may be the same or different.

[0021] R N1 、R N2 、R C1 、R C2 、R C3 、R C4 、R C5 、R C6 、R C7 、R C8 、R C9 、R C10 Each is independently selected from H or a C1-C6 straight or branched alkyl group.

[0022] “*” indicates that the carbon atom is chiral carbon.

[0023] In the present invention, the C6 to C12 indicates that the molecular chain or molecular structure contains 6 to 12 carbon atoms, for example, 6, 7, 8, 9, 10, 11, and 12; the C1 to C6 indicates that the molecular chain contains 1 to 6 carbon atoms, for example, 1, 2, 3, 4, 5, and 6; if the same expression is used below, it means the same meaning.

[0024] Preferably, R1, R2, and R3 are each independently selected from any one of H, a C1-C6 straight-chain alkyl group, a phenyl group, or a cholesterol ester group, and R1, R2, and R3 are different from each other.

[0025] Preferably, n is an integer selected from 1 to 5.

[0026] Preferably, the group It is linked to any position of A, and more preferably to the end of A's molecular chain.

[0027] In the present invention, different chiral groups in the organic compound can be connected to the same molecular chain end of A or different molecular chain ends.

[0028] Preferably, among the organic compounds, At least one selected from the following groups:

[0029] Dashed lines indicate the junction sites.

[0030] Preferably, said A is selected from rigid chromophores.

[0031] Preferably, the rigid chromophore is selected from dichroic rigid chromophores.

[0032] Preferably, the dichroic rigid chromophore group is selected from any one of a dichroic azo chromophore group, a dichroic rylene group, and a dichroic heterocyclic chromophore group.

[0033] Preferably, the dichroic azo chromophore group has a structure shown in Formula II;

[0034] Ar1-N=N-[Ar2-N=N] a -[Ar3-N=N] b -[N=C] c -[Ar4-N=N] d -Ar5 Formula II

[0035] wherein Ar1 and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C12 aryl group or a substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10) heteroaryl group.

[0036] In the present invention, the C2-C10 heteroaryl group includes a heteroaryl group containing one ring or two rings.

[0037] Ar2, Ar3, and Ar4 are each independently selected from substituted or unsubstituted C6-C12 arylene groups.

[0038] The substituted substituents include halogen, -CF3, -OCF3, sulfo, carboxyl, hydroxyl, nitro, cyano, phosphate, C1-C18 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C14, C16, C18, etc.) straight or branched alkyl, C6-C18 (e.g., C6, C7, C8, C9, C10, C12, C14, C16, C18, etc.) aryl, C2-C18 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, C14, C16, C18, etc.) amide, formyl, -COOR A1 、-COR A2 、-SO2R A3 、-CONR A4 R A5 、-NR A6 RA7 , C1-C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, etc.) alkoxy, C3-C12 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C12, etc.) cycloalkyl, C1-C12 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, etc.) alkylthio or C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C12, etc.) heteroaryl; the C1-C At least one H in the C1-C18 straight-chain or branched alkyl, C1-C12 alkoxy, C1-C12 alkylthio, or C3-C12 cycloalkyl group can be independently substituted by any one of amino, halogen, or cyano; at least one H in the C6-C18 aryl group can be substituted by any one of amino, cyano, halogen, C1-C8 straight-chain or branched alkyl, or C1-C8 straight-chain or branched haloalkyl; at least one CH2 or CH in the C1-C18 straight-chain or branched alkyl, C1-C12 alkoxy, or C3-C12 cycloalkyl group can be independently substituted by -O-, -NR- N1 - or -S-; at least one H in the C2-C10 heteroaryl group may be substituted by a substituent, and the range of the substituent is the same as the range of the aforementioned substituent.

[0039] The substituents can be connected to form a ring by chemical bonds; the substituents and the ring structure connected to them can be connected by a single bond, -O-, -S- or -NR N2 -Connect into a ring.

[0040] R A1 、R A2 、R A3 Each independently selected from C1-C12 straight or branched alkyl, C3-C18 cycloalkyl, C6-C12 aryl, any one of; at least one H in the C1~C12 straight-chain or branched alkyl group may be substituted by halogen, cyano or hydroxyl; at least one H in the C3~C18 cycloalkyl group may be substituted by halogen, cyano, hydroxyl or C1~C12 haloalkyl; at least one CH2 or CH in the C3~C18 cycloalkyl group may be replaced by O; at least one H in the C6~C12 aryl group may be substituted by halogen, cyano, hydroxyl, C1~C12 alkyl or C1~C12 haloalkyl.

[0041] R A11 is selected from C3-C18 cycloalkyl, wherein at least one H in the C3-C18 cycloalkyl may be substituted by halogen, cyano or hydroxyl; R A12 is selected from H, halogen, cyano or hydroxy.

[0042] R A13is selected from C3-C18 cycloalkylene, wherein at least one H in the C3-C18 cycloalkylene may be substituted by halogen, cyano, hydroxyl, C1-C12 alkyl or C1-C12 haloalkyl; R A14 Selected from H, halogen, cyano, hydroxy, C1-C12 alkyl or C1-C12 haloalkyl.

[0043] Dashed lines indicate the junction sites.

[0044] R A4 、R A5 、R A6 、R A7 Each is independently selected from any one of H, C1-C8 alkyl, C3-C12 cycloalkyl, phenyl or chiral group; R A4 With R A5 、R A6 With R A7 Can be independently connected by a single bond, -O-, -S- or -NR N2 -Connect into a ring.

[0045] R N1 、R N2 Each is independently selected from H or C1-C8 alkyl.

[0046] a, b, and d are each independently selected from integers of 0 to 2, for example, 0, 1, or 2; and c is selected from 0 or 1.

[0047] Preferably, Ar1 and Ar5 are each independently selected from the following groups, or any one of the following groups substituted by a substituent: The substituents are selected from the same range as Formula II; the number of the substituents is 1 or 2; and the dotted line represents the connection site.

[0048] Preferably, when c and d are each independently 0, or when c is 1 and d is 1, Ar5 is selected from the following groups, or any one of the following groups substituted by a substituent:

[0049] The substituent is selected from -NR A6 R A7 , C1 to C8 linear or branched alkyl, phenyl, halogen or cyano, wherein R A6 、R A7 Each is independently selected from any one of H, C1-C4 alkyl, C3-C12 cycloalkyl, phenyl or chiral group; R A6 With R A7 Can be separated by single bond, -O-, -S- or -NR N2 - connected into a circle; dotted lines indicate the connection sites.

[0050] Preferably, when c is not 0 and d is 0, Ar5 is selected from the following groups, or any one of the following groups substituted by a substituent:

[0051] The substituents include C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylthio, hydroxy, halogen, nitro, cyano, -COOR A1 、-COR A2 、-SO2R A3 、-CONR A4 R A5 、-NR A6 R A7 , C6-C12 aryl, C2-C10 heteroaryl or C3-C18 cycloalkyl; at least one H in the C1-C12 alkyl, C1-C12 alkoxy and C1-C12 alkylthio group can be independently substituted by halogen, hydroxyl or amino; at least one CH2 and CH in the C1-C12 alkyl, C1-C12 alkoxy and C3-C18 cycloalkyl group can be independently replaced by -O-, -NR- or -S-; at least one H in the C6-C12 aryl and C2-C10 heteroaryl group can be independently replaced by cyano, halogen, hydroxyl, -NR- A6 R A7 , C1~C12 alkyl, C1~C12 alkoxy, C1~C12 alkylthio; at least one H in the C3~C18 cycloalkyl group may be replaced by C1~C12 haloalkyl, halogen, CN, OH, C1~C12 alkoxy, C1~C12 alkylthio or -NR A6 R A7 Substitution; the substituent may form a 5-7 membered heterocyclic structure with the ring structure to which it is connected, wherein the heterocyclic structure contains at least one heteroatom, which is selected from at least one of O, S, and NR; at least one H in the heterocyclic structure may be replaced by a C1-C4 alkyl, Substitution; R is selected from C1~C12 alkyl, C3~C12 cycloalkyl or phenyl; at least one H in the phenyl group may be substituted by C1~C6 alkyl, F or CN.

[0052] Preferably, Ar2, Ar3, and Ar4 are each independently selected from the following groups, or any one of the following groups substituted by a substituent:

[0053] The substituent is selected from any one of a C1-C4 straight-chain or branched alkyl group, a C1-C4 alkoxy group, a halogen, a cyano group, a sulfo group, a carboxyl group, an amino group, a phenyl group or a C2-C8 amide group; at least one H in the C1-C4 straight-chain or branched alkyl group, the C1-C4 alkoxy group or the phenyl group can be independently replaced by an amino group, a halogen, a hydroxyl group or a cyano group; the dotted line indicates the connection site.

[0054] Preferably, the dichroic azo chromophore group has a structure shown in formula II-1 to formula II-5, or is substituted with a substituent and has any one of the structures shown in formula II-1 to formula II-5, and at least one H in the structure shown in formula II-1 to formula II-5 is replaced by replace:

[0055] The substituents are selected from the same range as those in Formula II.

[0056] Preferably, the dichroic rylene group has a structure shown in Formula III:

[0057] Wherein, X1, X2, Y1, and Y2 are each independently selected from H or -COOM; and at least one group among X1, X2, Y1, and Y2 is selected from -COOM; and X1 and X2, Y1 and Y2 can each independently be connected to form the structure shown in ring (a), ring (b), or ring (c).

[0058] Dashed lines indicate fusion sites; R N selected from H, substituted or unsubstituted C1-C30 (e.g., C1, C2, C4, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.) linear or branched alkyl, substituted or unsubstituted C3-C8 (e.g., C3, C4, C5, C6, C7, C8) cycloalkyl, substituted or unsubstituted C any one of C6-C20 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, etc.) aryl, substituted or unsubstituted C6-C20 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, etc.) heteroaryl; -O-, -S-, -NR- 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21-, -CO-, -SO- or -SO2-; the C3-C8 cycloalkyl, C6-C20 aryl or C6-C20 heteroaryl may be fused with a 5-7 membered saturated ring or a 5-7 membered unsaturated ring; the carbon skeleton of the 5-7 membered saturated ring or the 5-7 membered unsaturated ring may be inserted with -O-, -S-, -NR 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one H in the C6-C20 aryl or C6-C20 heteroaryl may be substituted by an azo group; R 21 is selected from hydrogen or C1-C18 straight or branched chain alkyl, wherein R 21 When the group appears more than once, it may be the same or different; Z is selected from any one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridinylene; M is selected from H, halogen or -B(OR B )2; R B Any one selected from H, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl; M, ring (a), ring (b) or ring (c) may be independently connected to a chiral group.

[0059] R is selected from any one of substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 heteroaryloxy, and substituted or unsubstituted C6-C30 heteroarylthio; the C6-C30 aryloxy, C6-C30 arylthio, C6-C30 heteroaryloxy, and C6-C30 heteroarylthio may each independently be fused to a 5-7 membered saturated ring or a 5-7 membered unsaturated ring; the carbon skeleton of the 5-7 membered saturated ring or the 5-7 membered unsaturated ring may be inserted with -O-, -S-, or -NR 21 -、-N=CR 21 -、 -C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-.

[0060] The number of the substituted substituents is at least one; the substituted substituents include C1-C30 straight chain or branched alkyl, C3-C8 cycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, -U-aryl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 22 、-CR 22 =C(R 23)2, hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 or-POR 22 R 23 At least one of .

[0061] In the substituent, -O-, -S-, -NR- 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the H in the C1-C30 straight or branched alkyl group may be replaced by a C1-C12 alkoxy group, a C1-C6 alkylthio group, a -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 , aryl, C1~C18 alkyl substituted aryl, C4~C7 saturated or unsaturated cycloalkyl, C1~C18 alkyl substituted C4~C7 saturated or unsaturated cycloalkyl; the carbon skeleton of the C4~C7 saturated or unsaturated cycloalkyl may be inserted with one or more -O-, -S-, -NR 21 -、-N=CR 21 -、-CR 21 =CR 21-, -CO-, -SO-, -SO2-; the C3-C8 cycloalkyl group may be fused with a 5- to 7-membered saturated or unsaturated ring; the carbon skeleton of the 5- to 7-membered saturated or unsaturated ring may be inserted with -O-, -S-, -NR 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the 5- to 7-membered saturated or unsaturated rings may be C1-C8 alkyl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 At least one of the substitutions;

[0062] In the substituents, C6-C20 aryl, C6-C20 heteroaryl, -U-aryl can be fused with a 5-7 membered saturated or unsaturated ring; -O-, -S-, -NR- can be inserted into the carbon skeleton of the 5-7 membered saturated or unsaturated ring. 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the C6-C20 aryl, C6-C20 heteroaryl, -U-aryl, 5-7 membered saturated or unsaturated rings, at least one H of which may be C1-C18 alkyl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 , aryl or heteroaryl, wherein the aryl or heteroaryl is independently substituted by C1-C18 alkyl, C1-C12 alkoxy, hydroxyl, mercapto, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 or-POR 22 R 23 At least one of the substitutions.

[0063] In the above substituents, -U- represents -O-, -S-, or -NR 21 -, -CO-, -SO- or -SO2-.

[0064] R 22 、R 23 are each independently selected from H.

[0065] m is an integer selected from 0 to 4, for example, 0, 1, 2, 3, or 4; n is an integer selected from 1 to 8, for example, 1, 2, 3, 4, 5, 6, 7, or 8.

[0066] Preferably, when m is 1, n is selected from an integer of 3 to 6; when m is 2, n is selected from an integer of 2 to 8.

[0067] Preferably, the dichroic rylene group has a structure shown in formula III-1 to formula III-4, or is substituted with a substituent and has any one of the structures shown in formula III-1 to formula III-4, and at least one H in the structure shown in formula III-1 to formula III-4 is replaced by replace;

[0068] Preferably, the dichroic heterocyclic chromophore has a structure shown in Formula IV, and at least one H in the structure shown in Formula IV is replace.

[0069] Ar 23-L3-(Ar 22 -L2) x -Ar 21 -L1-PL 1′ -Ar 21′ -(L 2′ -Ar 22′ ) x′ -L 3′ -Ar 23′ Formula IV

[0070] Wherein, P is selected from any one of the following structures; the straight line represents the connection site;

[0071] L1, L 1′ Each independently represents a single bond, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -N=N-, -CH=N-, -N=CH-, -N=N(O)-, -N(O)=N-, -CR 31 =CR 31 -、-(CR 31 =CR 31 )2-, -C≡C-, -CF=CF-, -C(=O)-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -CH=CH-COO- or -OCO-CH=CH-.

[0072] L2, L 2′ Each independently represents a single bond, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -N=N-, -CH=N-, -N=CH-, -N=N(O)-, -N(O)=N-, -CR 31 =CR 31 -、-(CR 31 =CR 31 )2-, -C≡C-, -CF=CF-, -C(=O)-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -CH=CH-COO-, -OCO-CH=CH-, -O-, -S-, -C(R 31 )2-, -C(O)-O-, -OC(O)-, -OC(O)-O-, -SCH2-, -CH2S-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2- or -(CF2) n1 -; n1 represents an integer greater than or equal to 1.

[0073] L3, L3′ Each independently represents a single bond, -O-, -S-, -C(R 31 )2-、-C(R 31 )2O-、-OC(R 31 )2-、-CR 31 =CR 31 -, -C≡C-, or a combination of at least two of the above groups.

[0074] Ar 21 、Ar 22 、Ar 23 、Ar 21′ 、Ar 22′ 、Ar 23′ Each independently selected from unsubstituted or substituted by at least one R 32 Substituted C5-C30 aryl, unsubstituted or replaced by at least one R 32 Any one of substituted C5-C30 heteroaryl groups.

[0075] R 31 、R 32 Each independently represents H, D, F, Cl, -CN, -N(R 33 )2, C1-C15 straight chain or branched alkyl, C1-C15 straight chain or branched alkoxy, C1-C15 straight chain or branched thioalkoxy, C2-C15 straight chain or branched alkenyl, C2-C15 straight chain or branched alkynyl, C5-C30 aryl or C5-C30 heteroaryl, wherein at least one H in the above groups can be replaced by R 33 Substitution, at least one CH2 group in the above groups can be replaced by -R 33 C=CR 33 -, -C≡C-, -CO-, -CS-, -C(=O)O-, -O(C=O)-, -Si(R 33 )2-、-NR 33 -, -O- or -S-.

[0076] R in different groups 33 Same or different, represents H, D, F, Cl, -CN, -N(R 34 )2, C1-C15 straight chain or branched alkyl, C1-C15 straight chain or branched alkoxy, C1-C15 straight chain or branched thioalkoxy, C2-C15 straight chain or branched alkenyl, C2-C15 straight chain or branched alkynyl, C5-C30 aryl or C5-C30 heteroaryl, wherein at least one H in the above groups can be replaced by R 34 Substitution, at least one CH2 group in the above groups can be replaced by -R 34 C=CR 34-, -C≡C-, -C=O-, -C=S-, -C(=O)O-, -O(C=O)-, -Si(R 34 )2-、-NR 34 -, -O- or -S-.

[0077] R in different groups 34 The same or different represents H, F, a C1-C20 aliphatic organic group, a C5-C20 aryl group, or a C5-C20 heteroaryl group; at least one H in the C1-C20 aliphatic organic group, a C5-C20 aryl group, or a C5-C20 heteroaryl group may be replaced by F.

[0078] E1 and E2 are each independently selected from O or -NR 39 .

[0079] R in different groups 39 、R 40 are the same or different, each independently representing H, D, F, Cl, -CN, -N(R 41 )2, C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C2~C15 straight chain or branched alkynyl, C5~C30 aryl or C5~C30 heteroaryl, wherein at least one H in the C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C1~C15 straight chain or branched alkynyl can be replaced by R 41 or R 50 At least one CH2 can be replaced by -R 41 、-C=CR 41 -, -C≡C-, -C=O-, -C=S-, -C(=O)O-, -O(C=O)-, -Si(R 41 )2-、-NR 41 -, -O- or -S-; at least one H in the C5-C30 aryl or C5-C30 heteroaryl may be replaced by R 50 replace.

[0080] R in different groups 41 Same or different, represents H, D, F, Cl, -CN, -N(R 42)2, C1~C15 straight chain or branched alkyl, C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C2~C15 straight chain or branched alkynyl, C5~C30 aryl or C5~C30 heteroaryl, wherein at least one H in the C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C1~C15 straight chain or branched alkynyl can be replaced by R 60 Substituted, at least one CH2 group may be -R 42 C=CR 42 -, -C≡C-, C=O, C=S, -C(=O)O-, -O(C=O)-, -Si(R 42 )2-、-NR 42 -, -O- or -S-, at least one H in the C5-C30 aryl or C5-C30 heteroaryl may be replaced by R 42 replace.

[0081] R in different groups 42 Identical or different, represents H, F, a C1-C20 aliphatic organic group, a C5-C20 aryl group, or a C5-C20 heteroaryl group; at least one H in the C1-C20 aliphatic organic group, the C5-C20 aryl group, or the C5-C20 heteroaryl group may be replaced by F.

[0082] R in different groups 50 Same or different, represents H, F, -CN, -CO-, -N(R 51 )2, -SO2R 51 , -CH=C(CN)2, any one of C1-C25 straight or branched alkyl, C3-C20 cycloalkyl, wherein one or more non-adjacent CH2, CH in C1-C25 straight or branched alkyl, C3-C20 cycloalkyl can be replaced by -O-, -S-, -C(R 51 )=C(R 51 )-、-C≡C-、-N(R 51 )-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, and at least one H may be replaced by F, Cl, Br, I or CN;

[0083] R in different groups 51 Same or different, R 51 、R 60Each is independently selected from any one of H, halogen, C1-C12 straight or branched alkyl, and C3-C12 cycloalkyl, wherein one or more non-adjacent CH2 and CH in the C1-C12 straight or branched alkyl and C3-C12 cycloalkyl can be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, and at least one H can be replaced by F or Cl.

[0084] W is selected from O, S or Se.

[0085] x and x' are each independently selected from integers of 0 to 4, for example, 0, 1, 2, 3, 4, etc.; and when x and x' are greater than 1, Ar 22 Can be the same or different; Ar 22′ Can be the same or different.

[0086] Preferably, the L1, L 1′ Each is independently selected from a single bond, -N=N-, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -CH=CH-, -CF=CF- or -C≡C-, more preferably a single bond, and when P is L1, L 1′ For a single bond.

[0087] Preferably, L2, L 2′ Each is independently selected from a single bond, -N=N-, -CH2CH2-, -CF2CF2-, -CH=CH-, -CF=CF-, -C≡C-, -OCH2-, -CH2O-, -OCF2- or -CF2O-, further preferably -N=N-, -OCF2-, -CF2O- or a single bond, more preferably -N=N- or a single bond.

[0088] Preferably, E1 and E2 are each independently selected from O.

[0089] Preferably, R 39 Selected from -CN; R 40 Selected from H, unsubstituted or replaced by R 50 Substituted C1-C15 straight-chain or branched alkyl, C5-C18 aryl or C5-C18 heteroaryl.

[0090] Preferably, R 50Selected from -CN, C1~C12 straight-chain alkyl, C1~C15 straight-chain alkoxy, C3~C25 branched alkyl or C3~C25 branched alkoxy, further preferably n-pentyl, n-hexyl, n-heptyl, 2-ethylhexyl, 2-ethylheptyl, 2-ethyloctyl, 2-ethylnonyl, 2-ethyldecyl, 3-ethylhexyl, 3-ethylheptyl, 3-ethyloctyl, 3-ethylnonyl, 3-ethyldecyl, 2-octyldodecyl or -CN.

[0091] Preferably, R 60 It is selected from a C1 to C9 straight-chain alkyl group, and more preferably an ethyl group.

[0092] Preferably, W is selected from S.

[0093] In the present invention, the organic compound is selected from any one of the following structural compounds;

[0094] Here, “*” indicates that the carbon atom is a chiral carbon.

[0095] In the present invention, the heteroaryl group comprises at least 5 aromatic ring atoms, at least one of which is a heteroatom. The heteroatom is preferably selected from N, O, and S. The heteroaryl group comprises at least one ring, or may be a heteroaryl group with two or more rings.

[0096] In the present invention, an aryl or heteroaryl group is understood to mean a single aromatic ring (e.g., benzene), a single heteroaromatic ring (e.g., pyridine, pyrimidine, or thiophene), or a fused (fused) aromatic or heteroaromatic polycyclic ring (e.g., naphthalene, phenanthrene, quinoline, or carbazole). Within the meaning of the present invention, a fused (fused) aromatic or heteroaromatic polycyclic ring consists of two or more single aromatic or heteroaromatic rings fused to one another. The polycyclic ring may also contain independent non-conjugated units, as is the case with fluorenyl groups.

[0097] Aryl or heteroaryl groups which can each be substituted by the above-mentioned radicals and which can be bonded to the aromatics or heteroaromatics via any position are understood in particular to be radicals derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, perylene, fluoranthene, benzanthracene, triphenylene, tetracene, pentacene, benzopyrene, fluorene, spirobifluorene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, ... phenanthene, dibenzothiophene, selenophene, benzoselenophene, dibenzoselenophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthalene imidazole, phenimidazole, pyridimidazole, pyrazimidazole, quinoxaline imidazole, oxazole, benzo Oxazole, naphthoxazole, anthraxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole.

[0098] In the present invention, the substituted or unsubstituted alkyl, alkenyl, and alkynyl groups preferably include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, octenyl, cyclooctenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, or octynyl.

[0099] In the present invention, the substituted or unsubstituted alkoxy or thioalkoxy is preferably methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cyclohexyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-trifluoroethoxy, thiomethyl, thioethyl, thio-n-propyl, thio-isopropyl, thio-n-butyl, thio-isobutyl, thio-sec-butyl, thio-tert-butyl, thio-n-butyl, thio- pentyl, thio-sec-pentyl, thio-n-hexyl, thiocyclohexyl, thio-n-heptyl, thiocycloheptyl, thio-n-octyl, thiocyclooctyl, thio-2-ethylhexyl, thiotrifluoromethyl, thiopentafluoroethyl, thio-2,2,2-trifluoroethyl, thiovinyl, thiopropenyl, thiobutenyl, thiopentenyl, thiocyclopentenyl, thiohexenyl, thiocyclohexenyl, thioheptenyl, thiocycloheptenyl, thiooctenyl, thiocyclooctenyl, thioethynyl, thiopropynyl, thiobutynyl, thiopentynyl, thiohexynyl, thioheptynyl or thiooctynyl.

[0100] In the present invention, the aliphatic organic group includes any non-aromatic or heteroaromatic organic group, preferably an alkyl group having 1 to 15 carbon atoms, an alkoxy group having 1 to 15 carbon atoms, or an alkenyl or alkynyl group having 2 to 15 carbon atoms.

[0101] In the present invention, the organic compounds can be prepared by conventional methods or known methods.

[0102] In a second aspect, the present invention provides a chiral dichroic dye, wherein the chiral dichroic dye comprises at least one organic compound according to the first aspect.

[0103] The numerical range described in the present invention includes not only the point values ​​listed above, but also any point values ​​between the above numerical ranges that are not listed. Due to space limitations and for the sake of simplicity, the present invention no longer exhaustively lists the specific point values ​​included in the range.

[0104] Compared with the prior art, the present invention has the following beneficial effects:

[0105] The organic compound provided by the present invention, through a specific molecular structure design, introduces a chiral group of a specific structure into the molecular chain. As a chiral dichroic dye, the organic compound has an order parameter higher than that of conventional chiral agents, a high dichroic ratio, high solubility, high absorbance, and a suitable helical twisting force constant. When used in a liquid crystal composition, it can not only improve the solubility of the dye in the liquid crystal composition, but also reduce the use of chiral agents, or even eliminate the need for adding chiral agents, thereby reducing costs and avoiding the problem of low solubility caused by chiral agents. DETAILED DESCRIPTION

[0106] The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the embodiments are merely to help understand the present invention and should not be regarded as specific limitations of the present invention.

[0107] The materials used in the present invention are as follows:

[0108] NBS N-bromosuccinimide

[0109] DMF N,N-dimethylformamide

[0110] THF Tetrahydrofuran

[0111] NMP N-Methylpyrrolidone

[0112] EA Ethyl acetate

[0113] PE petroleum ether

[0114] DCM dichloromethane;

[0115] In the present invention, in the preparation method, overnight means about 12 to 15 hours; room temperature means a temperature range of 18 to 23° C.; similar environmental conditions also include atmospheric pressure, and the atmospheric pressure environment is one atmosphere.

[0116] Example 1

[0117] This embodiment provides an organic compound with the structural formula The preparation method of the organic compound comprises the following steps:

[0118] (1) Intermediate 1a Synthesis

[0119] I: 35% hydrochloric acid (113.2 g), water (84.85 g), and 4-(trifluoromethyl)aniline (50.00 g) were added to a 1 L four-necked flask and reacted at 25°C for 35 min. The mixture was then cooled to -5°C and sodium nitrite solution (22.48 g of sodium nitrite dissolved in 50 mL of water) was added dropwise. After addition, the mixture was reacted at -5°C for 4 h to obtain reaction solution 1a.

[0120] II: HOCH2SO3Na (54.10 g), water (250.0 mL), and aniline (34.68 g) were added to a 500 mL four-necked flask and reacted at 65°C for 6 h to obtain reaction solution 2a;

[0121] III. The reaction solution 1a was added dropwise to the reaction solution 2a, and a saturated potassium acetate solution was added thereto to adjust the pH to about 5. The mixture was reacted at -5°C for 18 h. After the reaction was completed, the mixture was filtered and the filter cake was transferred to a 2 L four-necked flask. 600.0 mL of 25% KOH solution was added and the mixture was reacted at 75°C for 15 h. The mixture was cooled and filtered. The filter cake was washed with 50.00 mL of water and dried with air at 50°C for 18 h to obtain 70.05 g of a yellow solid with an HPLC purity of 77.49%, i.e., intermediate 1a.

[0122] (2) Intermediate 1b Synthesis

[0123] I. Intermediate 1a (40.00 g), 35% HCl (54.98 g), and DMF (800.0 mL) were added to a 1 L four-necked flask, and the mixture was reacted at 25°C for 1.5 h. The temperature was then adjusted to -5°C, and a sodium nitrite solution (10.93 g of sodium nitrite dissolved in 40.00 g of water) was added dropwise. After the addition was complete, the mixture was reacted for 2-5 h. Aminosulfonic acid (14.64 g) was added, and the mixture was reacted at -5°C for 1.5 h to obtain reaction solution 1b.

[0124] II. 1-Naphthylamine (23.75 g), DMF (80.00 mL), and 35% HCl (17.28 g) were added to a 2 L four-necked flask, and the reaction solution 1b was added dropwise thereto. The mixture was reacted at -5°C for 2.5 h. Subsequently, 2000 mL of water was added to the reaction system, and the mixture was filtered. 2000 mL of toluene was added to the obtained filter cake, and the mixture was refluxed at 115°C for 3 h. The mixture was filtered at 45°C, and the obtained filter cake was air-dried at 50°C to obtain 48.21 g of a dark green solid with HPLC purity of 74.49%, thereby obtaining intermediate 1b.

[0125] (3) Chiral intermediate 1c Synthesis

[0126] 1-Naphthylamine (5.00 g), (S)-1-bromo-2-methylbutane (6.33 g), K2CO3 (5.79 g), and DMF (35.00 mL) were added to a 250-mL four-necked flask and reacted at 100°C for 14 h. After the reaction, 140.0 mL of water was added and the mixture was extracted twice with 50.00 mL × 2 EA. The organic phase was washed with water, concentrated, and purified by column chromatography to obtain 3.66 g of a yellow liquid with a GC purity of 91.40%, thus obtaining chiral intermediate 1c.

[0127] (4) Preparation of organic compounds

[0128] I. Add intermediate 1b (5.00 g) and NMP (100.0 mL) to a 250 mL four-necked flask. Adjust the temperature of the flask to -5°C and add 40% nitrosylsulfuric acid (4.17 g) dropwise. After completion of the addition, react for 3 h to obtain reaction solution 1.

[0129] II. Intermediate 1c (3.11 g) and NMP (10.00 mL) were added to a 500 mL four-necked flask, the temperature was adjusted to -5°C, and reaction solution 1 was added dropwise thereto. After the addition was completed, the reaction was allowed to react for 14 h. After the reaction was completed, 1940 mL of water was added to the reaction system, stirred for 0.5 h, and filtered. 500.0 mL of methanol was added to the obtained crude product, the mixture was slurried at 70°C, filtered at 25°C, and the filter cake was air-dried at 50°C to obtain 2.22 g of a dark solid with HPLC purity of 96.70%, thereby obtaining the organic compound.

[0130] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0131] 1H NMR(400MHz,Chloroform-d)δ9.28–9.24(m,1H),9.21–9.17(m,1H),9.14–9.10(m,1H),8.33–8.24(m,3H),8.18(d, J=8.7Hz,2H),8.09(d,J=6.1Hz,4H),7.85(dd,J=8.6,3.1Hz,3H),7.82–7.77(m,2H),7.75–7.71(m,1H),7.62–7.57( m,1H),6.77(d,J=8.7Hz,1H),5.22(t,J=5.5Hz,1H),3.43(dt,J=11.8,5.7Hz,1H),3.32–3.23(m,1H),2.00–1.90(m, 1H), 1.66 (ddd, J=13.2, 7.5, 5.5Hz, 1H), 1.40 (dt, J=14.2, 7.4Hz, 1H), 1.14 (d, J=6.6Hz, 3H), 1.05 (t, J=7.4Hz, 3H).

[0132] Example 2

[0133] This embodiment provides an organic compound with the structural formula The preparation method of the organic compound comprises the following steps:

[0134] (1) Chiral intermediate 2a Synthesis

[0135] 1-Naphthylamine (7.00 g), K2CO3 (8.11 g), (R)-2-bromooctane (14.91 g), and DMF (35.00 mL) were added to a 100 mL three-necked flask and reacted at 100°C for 6 h. After the reaction, 150.0 mL of water was added, and the mixture was extracted twice with 200.0 mL of 2EA. The organic phases were combined and purified by column chromatography to obtain 4.50 g of a light yellow liquid with a GC purity of 89.03%, thereby obtaining chiral intermediate 2a.

[0136] (2) Synthesis of organic compounds

[0137] Intermediate 1b (5.00 g) and NMP (100.0 mL) were added to a 250 mL four-necked flask, the temperature was adjusted to -5°C, and 40% nitrosylsulfuric acid (4.17 g) was added dropwise. The reaction was allowed to proceed for 3 h. After the reaction, chiral intermediate 2a (3.53 g) was added, and saturated potassium acetate solution was added to adjust the pH to approximately 5. The reaction was continued at -5°C for 14 h. After the reaction was completed, 100.0 mL of water was added to the reaction system, stirred for 0.5 h, and filtered. 500.0 mL of methanol was added to the crude product, the mixture was slurried at 65°C, filtered at 25°C, and the filter cake was dried under air at 50°C to obtain 4.68 g of a dark solid with an HPLC purity of 96.98%, thus obtaining the organic compound.

[0138] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0139] 1H NMR(400MHz,Chloroform-d)δ9.25(d,J=8.5Hz,1H),9.22–9.16(m,1H),9.14–9.09(m,1H),8.31(d,J=8.6Hz,1H),8.29–8.23(m ,2H),8.20–8.14(m,2H),8.08(d,J=8.1Hz,4H),7.83(dd,J=9.0,3.0Hz,3H),7.81–7.75(m,2H),7.72(ddd,J=8.3,6.8,1.1Hz,1H ),7.61–7.55(m,1H),6.77(d,J=8.7Hz,1H),5.04(s,1H),3.89(d,J=6.8Hz,1H),1.80(ddt,J=11.8,9.9,4.5Hz,1H),1.68(ddt, J=13.4,8.7,6.4Hz,1H),1.58(s,2H),1.55–1.46(m,2H),1.41(d,J=6.3Hz,4H),1.34(dd,J=6.8,4.0Hz,3H),0.97–0.89(m,3H).

[0140] Example 3

[0141] This embodiment provides an organic compound with the structural formula The preparation method of the organic compound comprises the following steps:

[0142] (1) Intermediate 3a Synthesis

[0143] I. 35% hydrochloric acid (113.2 g), water (84.85 g), and 4-(trifluoromethyl)aniline (50.00 g) were added to a 1 L four-necked flask, and the mixture was reacted at 25° C. for 35 min. The temperature was adjusted to −5° C., and sodium nitrite solution (20.98 g of sodium nitrite dissolved in 50.00 mL of water) was added dropwise, and the mixture was reacted for 4 h. After completion of the reaction, urea (3.73 g) was added thereto, and the mixture was reacted at −5° C. for 1.5 h to obtain reaction solution 1.

[0144] II. m-Toluidine (39.90 g), 35% hydrochloric acid (38.79 g), and DMF (100.0 mL) were added to a 1 L four-necked flask, the temperature was adjusted to -5°C, reaction solution 1 was added dropwise thereto, the reaction was allowed to react overnight, and the mixture was filtered at 25°C. The filter cake was washed with 60.00 mL of water. To the obtained crude product, 600.0 mL of anhydrous ethanol and 100.0 mL of water were added, the mixture was heated to reflux, and the mixture was slowly cooled to room temperature and filtered. The filter cake was air-dried at 50°C for 18 h to obtain 52.76 g of a red solid (intermediate 3a) with HPLC purity of 95.30%.

[0145] (2) Chiral intermediate 3b Synthesis

[0146] Aniline (20.00 g), (S)-1-bromo-2-methylbutane (38.93 g), K2CO3 (35.62 g), and DMF (80.00 mL) were added to a 250 mL four-necked flask and reacted at 105°C for 22 h. After the reaction was completed, 320.0 mL of water was added, and the mixture was extracted with 200.0 mL×2 EA. The organic phases were combined, washed with water, dried, and then column chromatography was performed to obtain 19.90 g of a light yellow liquid, IY=56.76%, and HPLC purity: 74.26%.

[0147] (3) Synthesis of organic compounds

[0148] I. Intermediate 3a (40.00 g), 35% HCl (52.22 g), and DMF (800.0 mL) were added to a 1 L four-necked flask and reacted at 25°C for 1.5 h. The temperature was adjusted to -5°C, and sodium nitrite solution (13.84 g of sodium nitrite dissolved in 40.00 g of water) was added dropwise. The reaction was continued for 3 h to obtain reaction solution 1.

[0149] II. Chiral intermediate 3b (25.30 g) and DMF (80.00 mL) were added to a 1 L four-necked flask, the temperature was adjusted to -5°C, and reaction solution 1 was added dropwise thereto. After reacting for 1 h, potassium acetate (28.11 g) was added to adjust the pH. After reacting at -5°C for 14 h, 2000 mL of water was added to the reaction system, stirred for 0.5 h, and filtered at 20°C. 90.00 mL of toluene and 90.00 mL of 2-propanol were added to the crude product, and the mixture was slurried at 25°C for 4 h. The mixture was filtered and the filter cake was dried under air at 50°C to obtain 36.33 g of a brownish-red solid with HPLC purity of 98.76%. The organic compound was obtained.

[0150] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0151] 1H NMR(400MHz,Chloroform-d)δ8.04(d,J=8.3Hz,2H),7.92–7.87(m,2H),7.87–7.8 4(m,1H),7.82(d,J=1.9Hz,2H),7.81–7.77(m,2H),6.71–6.66(m,2H),3.19(dd,J= 12.6,6.1Hz,1H),3.04(dd,J=12.6,7.2Hz,1H),2.85(s,3H),1.75(dq,J=13.3,6.6 Hz,1H),1.54(dtd,J=14.9,7.4,5.3Hz,1H),1.33–1.21(m,1H),1.05–0.96(m,6H).

[0152] Example 4

[0153] This embodiment provides an organic compound with the structural formula The preparation method of the organic compound comprises:

[0154] (1) Intermediate 4a Synthesis

[0155] Intermediate 1b (2.00 g), 4-(diethylamino) salicylaldehyde (1.84 g), glacial acetic acid (1.00 mL), 2-propanol (15.00 mL), and molecular sieves (6.70 g) were added to a 250 mL three-necked flask and refluxed for 5 h. The mixture was cooled to 25° C. and filtered. The insoluble matter was removed by column chromatography of the filter cake. The chromatographic solution was concentrated at 45° C. to obtain a crude product. The crude product was slurried in 100.0 mL of 2-propanol and filtered. The filter cake was air-dried at 50° C. for 18 h to obtain 1.24 g of a dark green solid with HPLC purity of 99.37%.

[0156] (2) Synthesis of organic compounds

[0157] Intermediate 4a (5.68 g), (S)-1-bromo-2-methylbutane (2.16 g), Cs2CO3 (4.67 g), and DMF (30.00 mL) were added to a 250 mL three-necked flask and reacted at 110°C for 3 h. After the reaction, the temperature was lowered, 150.0 mL of water was added, and the mixture was filtered. The filter cake was slurried with 150.0 mL of anhydrous ethanol, filtered, and the filter cake was air-dried at 50°C to obtain 1.53 g of a brown-red solid with HPLC purity of 97.67%, thereby obtaining the organic compound.

[0158] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0159] 1H NMR(400MHz,Chloroform-d)δ9.06(d,J=8.4Hz,1H),8.93(s,1H),8.54(d,J=8.4Hz,1H),8.26(d,J=8.9Hz,1H),8.22(d,J=6.6Hz,1H),8.2 1(s,1H),8.18–8.14(m,2H),8.08(d,J=8.2Hz,2H),8.05(d,J=8.1Hz,1H),7.83(d,J=8.3Hz,2H),7.73(ddd,J=8.3,6.7,1.4Hz,1H),7.62(d dd,J=8.2,6.8,1.3Hz,1H),7.14(d,J=8.1Hz,1H),6.44(dd,J=9.0,2.3Hz,1H),6.15(d,J=2.3Hz,1H),3.91(ddd,J=30.3,8.8,6.0Hz,2H),3 .49(q,J=7.1Hz,4H),1.95(dq,J=12.9,6.4Hz,1H),1.66–1.56(m,2H),1.28(t,J=7.0Hz,6H),1.07(d,J=6.7Hz,3H),0.98(t,J=7.5Hz,3H).

[0160] Example 5

[0161] This embodiment provides an organometallic compound with the structural formula The preparation method of the organic compound comprises the following steps:

[0162] (1) Chiral intermediate 5a Synthesis

[0163] I. Add p-nitrobenzoic acid (50.00 g), N,N-dicyclohexylcarbodiimide DCC (74.08 g), 4-dimethylaminopyridine DMAP (7.31 g), and DCM (250.0 mL) to a 1 L four-necked flask. Adjust the temperature to 5°C, add (S)-2-methyl-1-butanol (31.65 g) dropwise, and react at 25°C for 12 h. After completion of the reaction, quench with 500.0 mL of water, allow the mixture to stand for separation, discard the aqueous phase, concentrate the organic phase, and perform column chromatography to obtain 66.59 g of a light yellow liquid with an IY ratio of 93.85%, thereby obtaining reactant 1.

[0164] II. Add reactant 1 (66.59 g), Pd / C (3.33 g), and anhydrous ethanol (350.0 mL) into a 500 mL four-necked flask, replace with N2 three times, then replace with H2 three times, and react at 45°C for 42 h. After the reaction, filter out the insoluble matter, concentrate the filtrate, and perform column chromatography to obtain 41.91 g of a light yellow oil with a GC purity of 72.04%, thereby obtaining chiral intermediate 5a.

[0165] (2) Intermediate 5b Synthesis

[0166] I. 35% hydrochloric acid (17.59 g), water (13.19 g), and chiral intermediate 5a (10.00 g) were added to a 250 mL four-necked flask, and the mixture was reacted at 25° C. for 35 min. The temperature was adjusted to −5° C., and sodium nitrite solution (3.26 g of sodium nitrite dissolved in 10.00 mL of water) was added dropwise. The mixture was reacted for 4 h. After completion of the reaction, urea (2.90 g) was added thereto, and the mixture was reacted at −5° C. for 2 h to obtain reaction solution 1.

[0167] II. m-Toluidine (6.20 g), 35% hydrochloric acid (6.03 g), and DMF (10.0 mL) were added to a 500 mL four-necked flask, the temperature was adjusted to -5°C, and the reaction solution 1 was added dropwise thereto. Then, KOAc (9.47 g) was added to adjust the pH. The reaction was allowed to react overnight. After completion of the reaction, 200.0 mL of water was added to the reaction solution, and the mixture was filtered at 25°C. The filter cake was washed with 60.00 mL of water. 100.0 mL of toluene was added to the crude product, and the mixture was heated to reflux. The mixture was slowly cooled to room temperature and filtered. The filter cake was air-dried at 50°C for 18 h to obtain 3.86 g of a brownish-red solid with HPLC purity of 90.17%.

[0168] (3) Synthesis of organic compounds

[0169] I. Intermediate 5b (3.83 g), 35% HCl (4.29 g), and DMF (80.0 mL) were added to a 250 mL four-necked flask and reacted at 25°C for 1.5 h. The temperature was adjusted to -5°C, and sodium nitrite solution (0.89 g of sodium nitrite dissolved in 4.00 g of water) was added dropwise. The reaction was continued for 3 h to obtain reaction solution 1.

[0170] II. N-phenylpyrrole (25.30 g) and DMF-2 (10.00 mL) were added to a 500 mL four-necked flask, the temperature was adjusted to -5 ° C, reaction solution 1 was added dropwise thereto, and the reaction was continued for 2 h. Potassium acetate (2.31 g) was added to adjust the pH, and the reaction was continued at -5 ° C for 14 h. 200.0 mL of water was added to the reaction system, stirred for 0.5 h, and filtered at 20 ° C. 50.00 mL of toluene and 50.00 mL of 2-propanol were added to the obtained crude product, and the mixture was beaten at 25 ° C for 3 h. The mixture was filtered and the filter cake was dried by air at 50 ° C to give 2.23 g of a brownish-red solid with an HPLC purity of 96.16%, thereby obtaining the organic compound.

[0171] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0172] 1H NMR (400MHz, Chloroform-d) δ8.24 (dd, J=8.6, 3.8Hz, 2H), 7.99 (ddd, J=21.6, 8.8, 3.6 Hz,4H),7.86(q,J=3.4Hz,2H),7.81(d,J=4.8Hz,1H),6.68(dd,J=9.0,3.8Hz,2H),4.35–4.17(m,2H),3.48(q,J=4.7, 3.9Hz, 4H), 2.87 (d, J = 3.7Hz, 3H), 2.12 (dt, J = 7.2, 3.5Hz, 4H), 1.59 (d, J = 3.8Hz, 7H), 1.36 (s, 1H), 1.20–0.95 (m, 6H).

[0173] Example 6

[0174] This embodiment provides an organic compound with the structural formula The preparation method of the organic compound comprises the following steps:

[0175] (1) Chiral intermediate 6a Synthesis

[0176] I. 35% hydrochloric acid (17.59 g), water (13.19 g), and intermediate 5a (10.00 g) were added to a 250 mL four-necked flask and incubated at 25 ° C for 35 min. The temperature was adjusted to -5 ° C, and sodium nitrite solution (3.26 g of sodium nitrite dissolved in 10.00 mL of water) was added dropwise. The reaction was allowed to proceed for 4 h. After completion of the reaction, urea (2.90 g) was added thereto, and the reaction was continued at -5 ° C for 2 h to obtain reaction solution 1.

[0177] II. m-Toluidine (6.20 g), 35% hydrochloric acid (6.03 g), and DMF (10.0 mL) were added to a 500 mL four-necked flask, the temperature was adjusted to -5°C, reaction solution 1 was added thereto, and then KOAc (9.47 g) was added to adjust the pH. The reaction was allowed to react overnight. After completion of the reaction, 200.0 mL of water was added to the reaction solution, and the mixture was filtered at 25°C. The filter cake was washed with 60.00 mL of water. 100.0 mL of toluene was added to the obtained crude product, the mixture was heated to reflux, and the mixture was slowly cooled to room temperature and filtered. The filter cake was air-dried at 50°C for 18 h to obtain 3.86 g of a brownish-red solid with HPLC purity of 90.17%.

[0178] (2) Intermediate 6b Synthesis

[0179] I. 35% hydrochloric acid (2.70 g), DMF (54.00 mL), and chiral intermediate 6a (2.70 g) were added to a 250 mL four-necked flask, and the mixture was reacted at 25°C for 35 min. The temperature was adjusted to -5°C, and sodium nitrite solution (0.60 g of sodium nitrite dissolved in 3.00 mL of water) was added dropwise. The mixture was reacted for 4 h. After completion of the reaction, urea (1.90 g) was added thereto, and the mixture was reacted at -5°C for 2 h to obtain reaction solution 1.

[0180] II. Add m-toluidine (1.07 g) and DMF (10.0 mL) to a 250 mL four-necked flask, adjust the temperature to -5 ° C, add reaction solution 1, and then add KOAc (1.63 g) to adjust the pH. The reaction is allowed to react overnight. After the reaction is completed, 200.0 mL of water is added to the reaction solution, filtered at 25 ° C, and the filter cake is washed with 20.00 mL of water. The filter cake is air-dried at 50 ° C for 18 h to obtain 3.20 g of a brown-red solid.

[0181] (3) Synthesis of organic compounds

[0182] Intermediate 6b (3.20 g) and NMP (65.00 mL) were added to a 250 mL four-necked flask, the temperature was adjusted to -5°C, 40% nitrosylsulfuric acid (2.99 g) was added dropwise, and the reaction was continued for 4 h. Then, 2-pyrrolidone thiophene (1.27 g) was added thereto, potassium acetate was added to adjust the pH to about 5, and the reaction was continued at -5°C for 14 h. 200.0 mL of water was added to the reaction system, stirred for 0.5 h, and filtered at 20°C. 50.00 mL of 2-propanol was added to the obtained crude product, and the mixture was slurried at 25°C for 4 h. The filter cake was dried by air at 50°C to obtain a brownish-red solid to obtain the organic compound.

[0183] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0184] 1H NMR(400MHz,Chloroform-d)δ8.05–8.00(m,2H),7.95(s,1H),7.90–7.82(m,3H),7.78–7.70(m,3H),7.63(t,J=3.5Hz,1H),6.38(s,1H),6.09(d,J =4.8Hz,1H),4.06(s,1H),3.52(d,J=7.7Hz,5H),2.87(dd,J=16.1,2.9Hz ,6H),1.98(d,J=12.2Hz,4H),1.89(t,J=15.6Hz,4H),1.79–1.68(m,6H).

[0185] Example 7

[0186] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0187] (1) Intermediate 7a Synthesis

[0188] I. 35% hydrochloric acid (17.41 g), DMF (20.00 mL), and chiral intermediate 5a (9.90 g) were added to a 250 mL four-necked flask, and the mixture was reacted at 25°C for 35 min. The temperature was adjusted to -5°C, and sodium nitrite solution (3.46 g of sodium nitrite dissolved in 10.00 mL of water) was added dropwise. The mixture was reacted for 4 h. After the reaction was completed, sulfamic acid (4.64 g) was added thereto, and the mixture was reacted at -5°C for 2 h to obtain reaction solution 1.

[0189] II. 1-naphthylamine (7.52 g), 35% hydrochloric acid (5.47 g), and DMF (20.0 mL) were added to a 500 mL four-necked flask, the temperature was adjusted to -5 ° C, reaction solution 1 was added dropwise thereto, and the reaction was allowed to react for 2 h. After completion of the reaction, 100.0 mL of water was added to the reaction solution, and the mixture was filtered at 25 ° C. The filter cake was washed with 20.00 mL of water, and 200.0 mL of toluene and 200.0 mL of isopropanol were added to the crude product, and the mixture was slurried and filtered at 25 ° C. The filter cake was air-dried at 50 ° C for 18 h to give 14.26 g of a dark green solid with HPLC purity of 80.31%.

[0190] (2) Intermediate 7b Synthesis

[0191] I. Intermediate 7a (14.00 g), 35% HCl (14.12 g), and DMF (280.0 mL) were added to a 500 mL four-necked flask, and the mixture was reacted at 25°C for 2 h. The temperature was then adjusted to -10-0°C, and a sodium nitrite solution (2.81 g of sodium nitrite dissolved in 14.00 g of water) was added dropwise. The mixture was reacted for 3 h. Aminosulfonic acid (3.76 g) was added thereto, and the mixture was reacted at -5°C for 1.5 h to obtain reaction solution 1.

[0192] II. 1-Naphthylamine (6.10 g), DMF (20.00 mL) and 35% HCl (4.44 g) were added to a 1 L four-necked flask, the temperature was adjusted to -5°C, reaction solution 1 was added dropwise thereto, and the reaction was allowed to react for 2.5 h. Then, 900.0 mL of water was added to the reaction system, and the mixture was filtered. 200.0 mL of isopropanol was added to the filter cake, and the mixture was refluxed for 4 h. The mixture was filtered at 25°C, and the filter cake was air-dried at 50°C to give 8.25 g of a dark green solid with HPLC purity of 41.31%.

[0193] (3) Synthesis of organic compounds

[0194] Intermediate 7b (4.00 g) and NMP (80.0 mL) were added to a 250 mL four-necked flask, the temperature was adjusted to -5°C, 40% nitrosylsulfuric acid (2.71 g) was added dropwise, and the reaction was continued for 4 h. N-sec-butyl 1-naphthylamine (1.70 g) was added thereto, potassium acetate was added to adjust the pH to about 5, and the reaction was continued at -5°C for 14 h. 240.0 mL of water was added to the reaction system, stirred for 0.5 h, and filtered at 20°C. 60.00 mL of methanol was added to the obtained crude product, and the mixture was refluxed for 3 h, filtered, and the filter cake was air-dried at 50°C to obtain 3.53 g of a brownish-red solid, namely the organic compound.

[0195] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0196] 1H NMR(400MHz,Chloroform-d)δ9.28(d,J=22.3Hz,4H),9.13(s,1H),8.40–8.27(m,4H),8.20 (d,J=7.3Hz,4H),8.11(d,J=8.7Hz,1H),7.84(d,J=13.1Hz,5H),7.76(s,1H),7.62(s,1H),6 .82(d,J=8.6Hz,1H),5.06(s,1H),4.33(s,1H),4.26(s,1H),3.88(s,1H),1.98(s,1H),1.88 (s,1H),1.78(s,1H),1.45(dd,J=6.4,2.8Hz,3H),1.17–1.09(m,6H),1.06(t,J=7.4Hz,3H).

[0197] Example 8

[0198] This embodiment provides an organometallic compound, The preparation method of the organic compound comprises the following steps:

[0199] (1) Intermediate 8a Synthesis

[0200] (S)-1-bromo-2-methylbutane (30 g), potassium phthalimide (55.5 g) and DMF (50 mL) were placed in a reactor, heated to 110 ° C, kept warm for 8 hours, cooled to room temperature, added with 200 mL of water, extracted with 100 mL of EA, and the organic phase was collected, washed with 50 mL of water, dried with sodium sulfate (30 g), and the solvent was evaporated to obtain 35 g of a crude product.

[0201] (2) Intermediate 8b Synthesis

[0202] Intermediate 8a (35 g), hydrazine hydrate (50 g, 30%), and methanol (150 mL) were added to a 500 mL four-necked flask and heated under reflux for 8 h. The temperature was then cooled to room temperature, and water (500 mL) was added. The mixture was extracted with DCM (200 mL) × 2. The DCM phases were combined, washed with water, dried over anhydrous sodium sulfate, and the DCM and methanol were removed by short distillation under normal pressure to obtain 10 g of the product with a GC purity of 80%.

[0203] (3) Synthesis of organic compounds

[0204] 3,4,9,10-Perylenetetracarboxylic dianhydride (1 g), intermediate 8b (2 g), DMF (20 mL), and propionic acid (2 mL) were placed in a 100 mL reaction flask, purged with nitrogen, and heated to 100°C for 48 h. The mixture was cooled to room temperature, and extracted twice with 50 mL of water and DCM (50 mL each). The DCM phases were combined, washed with 50 mL of water, and the solvent was removed. The mixture was then applied to a 100-200 mesh silica gel column and chromatographed on a PE+DCM column to yield 1 g of an orange solid with a purity greater than 95%, thereby obtaining the organic compound.

[0205] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0206] 1H NMR(400MHz,Chloroform-d)δ8.72(d,J=8.0Hz,4H),8.66(d,J=8.1Hz,4H),4.14(dd, J=7.3,3.3Hz,4H),2.09(d,J=7.1Hz,2H),1.37–1.27(m,4H),0.99(d,J=6.5Hz,12H).

[0207] Example 9

[0208] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0209] 3,9-Perylene acid (1 g), (S)-(-)-2-methylbutanol (2 g), toluene (20 mL), and concentrated sulfuric acid (0.5 mL) were placed in a 100 mL reaction flask and heated under reflux for 20 h. The mixture was cooled to room temperature, washed with water (20 mL), dried over sodium sulfate, and the solvent removed. The mixture was then applied to a 100-200 mesh silica gel column and chromatographed on a PE+DCM column to obtain 0.5 g of an orange solid with a purity greater than 95%, thereby obtaining the organic compound.

[0210] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0211] 1H NMR(400MHz,Chloroform-d)δ8.23(d,J=7.9Hz,2H),8.17(d,J=2.0Hz,2H),8.16 (d,J=5.5Hz,2H),7.73(dd,J=17.2,8.0Hz,1H),7.65–7.58(m,2H),7.50(t,J=7. 8Hz,1H),4.37–4.31(m,2H),4.27(dt,J=7.1,2.9Hz,2H),2.00–1.94(m,2H),1.6 7–1.59(m,4H),1.12(d,J=2.2Hz,3H),1.11(d,J=2.2Hz,3H),1.06–1.02(m,6H).

[0212] Example 10

[0213] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0214] (1) Intermediate 10a Synthesis

[0215] 2,6-Diisopropyl 4-bromoaniline (40 g), benzyl bromide (67 g), potassium carbonate (71 g), and 200 mL of DMF were placed in a reactor, heated to 110°C for 20 h, cooled to room temperature, added with water (400 g), extracted twice with EA (200 mL), washed with 200 mL of water, dried over sodium sulfate, and separated by a PE column to obtain 60 g of intermediate 10a with a GC purity of 98.5%.

[0216] (2) Intermediate 10b Synthesis

[0217] Intermediate 10a (30 g), pinacol diboronate (22.5 g), potassium acetate (13 g), toluene (200 mL), and Pd-132 (0.1 g) were heated under reflux under nitrogen purge for 4 hours. The mixture was cooled to room temperature, washed twice with 100 mL of water, and then dried. The crude product was slurried with 200 mL of ethanol, filtered, and dried to yield 27 g of product with a GC purity of 99%.

[0218] (3) Intermediate 10c Synthesis

[0219] Intermediate 10b (28 g), 20% aqueous sodium hydroxide solution (20 g), and THF (150 mL) were added to a 500 mL reaction flask, and 10 g of hydrogen peroxide (30%) was added dropwise at room temperature. After reacting for 1 h, the mixture was quenched with saturated aqueous sodium bisulfite solution (20 g). The THF was removed, and the mixture was extracted with EA (200 mL) and water (100 mL). The mixture was dried over sodium sulfate and evaporated to give 20 g of intermediate 10c with a GC purity of 99%.

[0220] (4) Intermediate 10d Synthesis

[0221] Intermediate 10c (20 g), (S)-1-bromo-2-methylbutane (12 g), cesium carbonate (31.4 g), and DMF (200 mL) were added to a 500 mL reaction flask and heated to 110°C for 8 h. The mixture was cooled to room temperature, and water (400 mL) was added. Extraction with EA (400 mL) was performed, and the residue was evaporated to dryness. Column chromatography was performed to obtain 17 g of intermediate 10d with a GC purity of 97.5%.

[0222] (5) Intermediate 10e Synthesis

[0223] Intermediate 10d (17 g), palladium on carbon (1 g), and THF (100 mL) were added to an autoclave, the atmosphere was replaced with nitrogen, and hydrogen was introduced at a pressure of 0.5 MPa and an internal temperature of 50°C. The reaction was allowed to complete after 10 h. The palladium on carbon was filtered out, dried, and purified by PE:DCM column chromatography to obtain 8 g of intermediate 10e with a purity of 98%.

[0224] (6) Intermediate 10f Synthesis

[0225] 3,4,9,10-Perylenetetracarboxylic dianhydride (12 g), intermediate 10e (4 g), zinc acetate (10 g), and quinoline (100 mL) were added to a 250 mL reaction flask. After nitrogen purging, the reaction was heated to 190°C for 20 h. The quinoline (mL) was evaporated under reduced pressure, the temperature was lowered to 80°C, ethanol (200 mL) was added, and the temperature was lowered to room temperature and stirred for 1 h. The mixture was then filtered and the filter cake was washed with ethanol until the filtrate was colorless. The filter cake was dried and purified by PE+DCM column chromatography to obtain 4 g of red intermediate 10f with an HPLC purity of 97%.

[0226] (7) Synthesis of organic compounds

[0227] Intermediate 10f (3 g), potassium tert-butoxide (7.5 g), 1,8-diazabicycloundec-7-ene DBU (9 g), and ethanolamine (9 g) were nitrogen-purged and heated to 170° C. for 8 h. After cooling to room temperature, ethanol (100 mL) was added for crystallization. The mixture was filtered and the filter cake was washed with ethanol until the filtrate was colorless. The filter cake was subjected to column chromatography, washed with DCM, and dried to obtain 2 g of a blue-green solid sample with a purity of 99%, thereby obtaining the organic compound.

[0228] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0229] 1H NMR(400MHz,Chloroform-d)δ8.69(dd,J=7.9,3.5Hz,4H),8.58–8.30(m,12H),6.88(d,J=3.5Hz,4H),3.98–3.77(m,4H),2.79(d,J= 9.7Hz, 4H), 1.93 (m, 2H), 1.75 (m, 2H), 1.33 (m, 2H), 1.22 (dd, J = 6.9, 3.4Hz, 24H), 1.08 (dd, J = 6.8, 3.4Hz, 6H), 1.02 (d, J = 8.1Hz, 6H).

[0230] Example 11

[0231] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0232] 3,4,9,10-Perylenetetracarboxylic dianhydride (1 g), intermediate 10e (2 g), NMP (10 mL), and propionic acid (2 mL) were placed in a reactor, heated to an internal temperature of 150° C., reacted for 24 h, cooled to room temperature, added with water (30 mL), stirred for 0.5 h, and filtered to obtain a red crude product; column chromatography, eluted with DCM, obtained 0.5 g of the product with an HPLC purity of 98%, i.e., the organic compound was obtained.

[0233] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0234] 1H NMR (400MHz, Chloroform-d) δ8.72(d,J=8.0Hz,4H),8.66(d,J=8.1Hz,4H),6.88(d,J=3.5Hz,4H), 3.98–3.77(m,4H),2.79(d,J=9. 7Hz, 4H), 1.93 (m, 2H), 1.75 (m, 2H), 1.33 (m, 2H), 1.22 (dd, J = 6.9, 3.4Hz, 24H), 1.08 (dd, J = 6.8, 3.4Hz, 6H), 1.02 (d, J = 8.1Hz, 6H).

[0235] Example 12

[0236] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0237] (1) Intermediate 12a Synthesis

[0238] (S)-1-Bromo-2-methylbutane (1g), zinc powder (8.7g), and anhydrous DMF were used as the solvent. The reaction was initiated at 80°C, and the remaining (S)-1-bromo-2-methylbutane (9g) was added dropwise. The reaction was allowed to complete for 2 hours to yield the zinc reagent. Intermediate 10a (14.5g) and anhydrous DMF (50mL) were used as the base, and 1,1'-bis(diphenylphosphinoferrocenepalladium) dichloride (0.5g) was added. The mixture was heated to 70°C, and the zinc reagent was added dropwise. The reaction was allowed to react for 5 hours. The reaction was quenched with dilute hydrochloric acid, extracted with EA, washed with water, and dried. Crystallization from ethanol (20mL) yielded 10.2g of intermediate 12a with an HPLC purity of 95%.

[0239] (2) Intermediate 12b Synthesis

[0240] Intermediate 12a (10.2 g), palladium on carbon (0.1 g), and THF (100 mL) were added to an autoclave, the atmosphere was replaced with nitrogen, and hydrogen was introduced at a pressure of 0.5 MPa and an internal temperature of 50°C. The reaction was allowed to proceed for 10 h. The palladium on carbon was filtered, dried, and purified by PE:DCM column chromatography to yield 5.8 g of intermediate 12b with a purity of 95%.

[0241] (3) Intermediate 12c Synthesis

[0242] 3,4,9,10-Perylenetetracarboxylic dianhydride (14 g), intermediate 12b (5 g), zinc acetate (12 g), and quinoline (100 mL) were added to a 250 mL reaction flask. After nitrogen purging, the mixture was heated to 190°C for 20 h. Quinoline (80 mL) was evaporated under reduced pressure, the temperature was lowered to 80°C, ethanol (200 mL) was added, and the mixture was cooled to room temperature and stirred for 1 h. The mixture was then filtered and the filter cake was washed with ethanol until the filtrate was colorless. The filter cake was dried and purified by PE+DCM column chromatography to yield 4.5 g of red intermediate 12c with an HPLC purity of 97%.

[0243] (4) Synthesis of organic compounds

[0244] Intermediate 12c (4.5 g), potassium tert-butoxide (11 g), DBU (12 g), and ethanolamine (16 g) were placed in a reactor. After nitrogen replacement, the reaction was heated to 170° C. for 8 h. The reaction mixture was cooled to room temperature and ethanol (100 mL) was added for crystallization. The reaction mixture was filtered, and the filter cake was washed with ethanol until the filtrate was colorless. The filter cake was subjected to column chromatography, washed with DCM, and dried to obtain 2.5 g of a blue-green solid sample with a purity of 99%, thereby obtaining the organic compound.

[0245] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0246] 1H NMR(400MHz,Chloroform-d)δ8.69(dd,J=7.9,3.5Hz,4H),8.58–8.30(m,12H),6.88(d,J=3.5Hz,4H),2.79(d,J=9.7Hz,4H),2.53–2 .28(m,4H),1.93(m,2H),1.75(m,2H),1.33(m,2H),1.22(dd,J=6.9,3.4Hz,24H),1.08(dd,J=6.8,3.4Hz,6H),1.02(d,J=8.1Hz,6H).

[0247] Example 13

[0248] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0249] (1) Intermediate 13a Synthesis

[0250] 4,7-Dibromobenzo[c][1,2,5]thiadiazole (5g), 2-cyanothiophene (5g), potassium phosphate (14g), and Pd-132 (0.01g) were dissolved in a mixture of DMF (20mL) and water (2mL) in a 100mL single-necked flask. The mixture was refluxed at 100°C for 8 hours. TLC confirmed the complete reaction of 4,7-dibromobenzo[c][1,2,5]thiadiazole. The mixture was extracted with 50mL of water and 50mL of ethyl acetate. The organic phase was extracted three times with 50mL of water and once with ethyl acetate (50mL). The combined organic phases were extracted once with saturated brine (50mL). The organic phase was dried over anhydrous sodium sulfate and 100g of silica gel powder was added. The mixture was purified by flash column chromatography to obtain 4.3g of a dark yellow pure product with a yield of 86%.

[0251] (2) Intermediate 13b Synthesis

[0252] Intermediate 13a (4.3 g) was dissolved in dichloromethane (30 mL) and placed in a 100 mL single-necked flask. N-bromosuccinimide (NBS) (5.2 g) was added portionwise at 25°C. After the reaction of intermediate 13a was complete as determined by HPLC, saturated sodium bisulfite solution (20 mL) was added to quench the reaction. The mixture was stirred at room temperature for 20 minutes, separated, and the organic phase was dried over anhydrous sodium sulfate to obtain 6.5 g of a pure brown product in a 100% yield.

[0253] (3) Synthesis of organic compounds

[0254] Intermediate 13b (6.5 g, 14.3 mmol), 2-fluoro-4-((2S)-2-methyl-1-butoxy)phenylboronic acid pinacol ester (9.61 g, 33.2 mmol), potassium carbonate (7.9 g, 57 mmol), and Pd132 (0.01 g, 0.014 mmol) were dissolved in a mixed solvent of THF (50 mL) and water (10 mL) in a 100 mL single-necked flask and refluxed at 70° C. for 8 hours. Thin layer chromatography detected that the reaction of intermediate 13b was complete. The solvent was dried, and 50 mL of water and 50 mL of ethyl acetate were added for extraction. The aqueous phase was extracted three times with ethyl acetate (50 mL×3). The organic phases were combined and extracted once with saturated brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, 100 g of silica gel powder was added, and flash column chromatography was performed to obtain 7.55 g of a reddish-brown pure product with a yield of 80%, thereby obtaining the organic compound.

[0255] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0256] 1H NMR(400MHz,Chloroform-d)δ8.17(dd,J=4.1,2.2Hz,2H),7.96(d,J=2.5Hz,2H),7.67( dd,J=4.3,2.3Hz,2H),7.52(dt,J=9.6,2.5Hz,2H),6.99(td,J=5.9,4.8,2.6Hz,4H),3. 99(dtd,J=27.1,6.6,4.2Hz,4H),2.20–2.04(m,2H),1.80(ddd,J=14.2,9.7,5.8Hz,2H) ,1.46(dd,J=13.6,6.9Hz,2H), 1.22(dd,J=6.9,2.5Hz,6H), 1.07(td,J=7.2,2.4Hz,6H).

[0257] Example 14

[0258] This embodiment provides an organic compound, ; The preparation method of the organic compound comprises the following steps:

[0259] (1) Intermediate 14a Synthesis

[0260] Sodium (5 g) was dissolved in tert-amyl alcohol (100 mL) and refluxed for 2 h. The temperature was cooled to 25°C, dimethyl succinate (8 g) was added, and the mixture was heated to 100°C. 2-Cyanothiophene (13 g) was added portionwise and the reaction was continued for 48 h. Water (100 mL) was added to the reaction solution, which was filtered with suction. The crude product was recrystallized from a mixed solvent of PE (100 mL) and THF (10 mL) to obtain 10 g of pure product 14a.

[0261] (2) Intermediate 14b Synthesis

[0262] 14a (10 g) was dissolved in DMF (50 mL), and isooctane bromide (19.3 g) and potassium carbonate (14.1 g) were added. The mixture was refluxed for 24 h. TLC confirmed the complete reaction of 14a. Water was added to the reaction solution, and the mixture was extracted three times with EA (150 mL). The combined organic phases were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and dehydrated. 16.7 g of pure 14b was obtained by PE crystallization.

[0263] (3) Intermediate 14c Synthesis

[0264] Intermediate 14b (16.7 g) was dissolved in THF, and NBS (11.85 g) was added and monitored by TLC. After the reaction of intermediate 14b was completed, saturated sodium sulfite solution was added to quench the reaction, and the mixture was extracted three times with EA (150 mL). The organic phases were combined and washed with saturated sodium chloride aqueous solution. The organic phase was dried over anhydrous sodium sulfate and evaporated to obtain 21.4 g of the pure product.

[0265] (4) Intermediate 14d Synthesis

[0266] p-Bromophenol (20 g), (S)-1-bromo-2-methylbutane (21 g), potassium carbonate (24 g), and DMF (200 mL) were added to a 500 mL reaction flask and heated to 110°C for 8 h. The mixture was cooled to room temperature, and 400 mL of water was added. Extraction was performed with 400 mL of EA, and the mixture was evaporated to dryness. Column chromatography was performed to obtain 25 g of intermediate 14d with a GC purity of 99%.

[0267] (5) Intermediate 14e Synthesis

[0268] Intermediate 14d (25 g), pinacol diboronate (31 g), potassium acetate (15.2 g), toluene (200 mL), and Pd132 (0.1 g) were placed in a reactor under nitrogen purge and heated under reflux for 4 h. The reaction mixture was cooled to room temperature, washed twice with 100 mL of water, and then dried. The crude product was slurried in ethanol (200 mL), filtered, and the filter cake dried to yield 26 g of product with a GC purity of 99%.

[0269] (6) Synthesis of organic compounds

[0270] Intermediate 14c (21.4 g), intermediate 14e (14.98 g), potassium carbonate (12.78 g) and palladium catalyst (0.02 g) were dissolved in a mixed solution of THF (100 mL) and water (20 mL), and the reaction was stirred at 70° C. under nitrogen protection. TLC detection was performed until the reaction of intermediate 14c was complete. Water (100 mL) and EA (100 mL) were added to the reaction solution, and the mixture was separated and extracted. The organic layer was retained and dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography with a mixed solvent of PE and EA to obtain 23.3 g of a pure product with an HPLC purity of 99%, thereby obtaining the organic compound.

[0271] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0272] 1H NMR(400MHz,Chloroform-d)δ8.94(d,J=3.6Hz,2H),7.64–7.54(m,4H),7.35(d,J=3.8Hz ,2H),7.00–6.89(m,4H),4.12–4.03(m,4H),3.87(ddd,J=9.0,6.0,2.8Hz,2H),3.79(dt,J =9.2,4.6Hz,2H),2.00–1.83(m,4H),1.60(dd,J=14.6,7.8Hz,2H),1.42–1.35(m,8H),1. 26(d,J=7.4Hz,12H),1.06–1.01(m,6H),0.97(dd,J=7.3,2.9Hz,4H),0.92–0.84(m,12H).

[0273] Example 15

[0274] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0275] (1) Intermediate 15a Synthesis

[0276] 2-Fluoro-4-bromophenol (20 g), (S)-1-bromo-2-methylbutane (20 g), potassium carbonate (24 g), and 200 mL of DMF were added to a 500 mL reaction flask and heated to an internal temperature of 110°C for 8 h. The reaction was then cooled to room temperature, and water (400 mL) was added. Extraction with EA (400 mL) was performed, and the mixture was evaporated to dryness. Column chromatography was performed to obtain 24 g of intermediate 15a with a GC purity of 99%.

[0277] (2) Intermediate 15b Synthesis

[0278] Magnesium turnings (2.3 g) were added to a 500 mL reaction flask. Intermediate 15a (24 g) was diluted with THF (120 mL), and 20 mL was added to the reaction flask. After heating and initiation, the remaining 100 mL was added dropwise to the reaction flask. The reaction was allowed to complete after 1 h. The temperature was lowered to -30°C, and trimethyl borate (12.5 g) was added dropwise. After completion of the addition, the reaction was continued at -20°C for 1 h. Concentrated hydrochloric acid (40 g) was added dropwise to quench the reaction. The mixture was extracted with EA, dried, slurried with PE (100 mL), and dried to obtain 17 g of pure product.

[0279] (3) Synthesis of organic compounds

[0280] Intermediate 14c (10.7 g) was dissolved in THF, and intermediate 15b (7.49 g), potassium carbonate (6.39 g) and palladium catalyst (0.01 g) were added to a mixed solution of THF (100 mL) and water (20 mL). The mixture was stirred at 70° C. under nitrogen protection and detected by TLC until the reaction of intermediate 14c was complete. Water (100 mL) and EA (100 mL) were added to the reaction solution, and the mixture was separated and extracted. The organic layer was retained and dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography with a mixed solvent of PE and EA to obtain 11.7 g of a pure product with a purity of 99%, thereby obtaining the organic compound.

[0281] The structure of the organic compound was characterized by hydrogen nuclear magnetic resonance spectroscopy, and the results were as follows:

[0282] 1H NMR(400MHz,Chloroform-d)δ8.97(d,J=4.2Hz,2H),7.67(t,J=3.4Hz,2H),7. 44(d,J=9.2Hz,2H),7.06–6.89(m,4H),4.10(d,J=7.6Hz,4H),3.97(d,J=7.3Hz ,2H),3.89(d,J=7.5Hz,2H),1.99(d,J=35.4Hz,4H),1.63(s,2H),1.43–1.30(m ,12H),1.26(s,6H),1.15–1.06(m,6H),1.02–0.94(m,6H),0.92–0.81(m,12H).

[0283] Example 16

[0284] This embodiment provides an organic compound, The specific synthesis method of the organic compound is shown in Example 5.

[0285] Example 17

[0286] This embodiment provides an organic compound, The preparation method of the organic compound comprises the following steps:

[0287] (1) Intermediate 17a Synthesis

[0288] Catechol (20 g, (S)-1-bromo-2-methylbutane (68.11 g), powdered potassium carbonate (87.70 g), and 200 mL of DMF were placed in a 1-L four-necked flask under nitrogen. Condensed water was added, magnetic stirring was activated, and the mixture was heated to an internal temperature of 90°C overnight. GC analysis confirmed the absence of residual starting material. Post-treatment column chromatography afforded 16 g of intermediate 17a.

[0289] (2) Intermediate 17b Synthesis

[0290] 5 g of intermediate S1 and 25 mL of acetic acid were placed in a 250 mL four-necked flask. Magnetic stirring was initiated and concentrated nitric acid was added dropwise. A dry ice-alcohol bath was immediately used to control the internal temperature below 35°C. After 1 h of reaction, GC analysis confirmed complete reaction. Post-processing yielded 6 g of intermediate 17b as a yellow solid.

[0291] (3) Intermediate 17c Synthesis

[0292] Intermediate S2 (6 g), palladium on carbon (0.3 g), and ethanol (60 mL) were placed in a 500 mL single-necked flask, connected to a spherical condenser, and the atmosphere was purged with nitrogen three times and hydrogen three times. The mixture was then catalytically hydrogenated in an oil bath at 40°C overnight. GC analysis confirmed the reaction was complete, and post-processing afforded 6 g of intermediate 17c.

[0293] (4) Synthesis of organic compounds

[0294] Intermediate S3 (1.5 g), tetrachloroperylene anhydride (1 g), zinc acetate (0.52 g), and 15 mL of redistilled quinoline were placed in a 100 mL single-necked flask, fitted with a condenser, and magnetically stirred. After nitrogen displacement three times, the oil was heated to 160°C and reacted for 5 h. TLC confirmed the formation of product. Column chromatography using PE and DCM afforded 0.92 g of a red solid.

[0295] Comparative Example 1 (Intermediate 4a)

[0296] This comparative example provides an organic compound, (Intermediate 4a), no chiral group is introduced into the molecular structure.

[0297] Comparative Example 2

[0298] This comparative example provides an organic compound, The preparation method of the organic compound is referred to Example 13.

[0299] Comparative Example 3

[0300] This comparative example provides an organic compound, The synthesis method of the organic compound is shown in Example 12.

[0301] Performance Testing

[0302] The organic compounds provided in Examples 1 to 17 and Comparative Examples 1 to 3 of the present invention were mixed with the liquid crystal composition A to prepare a liquid crystal display device, and the performance test was performed.

[0303] The formula of the liquid crystal composition A is shown in Table 1 in terms of mass percentage. For ease of expression, the group structure of each compound in the liquid crystal composition A is represented by the codes listed in Table 2.

[0304] Table 1

[0305] Table 2

[0306] Take the following compound as an example:

[0307] If the structural formula is represented by the codes listed in Table 2, it can be expressed as: nPPN, where n in the code represents the number of carbon atoms in the left-hand alkyl group. For example, if n is "5", it means that the alkyl group is -C5H9; P in the code represents 1,4-phenylene, and N represents cyano.

[0308] The liquid crystal display device is prepared by uniformly mixing a dichroic dye (the organic compounds provided in Examples 1 to 17 and Comparative Examples 1 to 3) with a liquid crystal composition A (unless otherwise specified, the mass percentage of the dichroic dye is 1% and the mass percentage of the liquid crystal composition A is 99%) to obtain a dye liquid crystal. The liquid crystal mixture A and the prepared dye liquid crystal are respectively poured into a 30 mm x 30 mm upper and lower antiparallel cell with a thickness of 10 μm; and the maximum absorption value λ is measured. max (nm), maximum absorbance A, dichroic ratio, order parameter and HTP value.

[0309] (1) Test dichroic ratio and order parameter

[0310] Linearly polarized light is obtained using a Thorlabs CCM1-PBS251 polarizing prism with a wavelength of 420 to 680 nm. First, the matrix liquid crystal cell is adjusted so that the vibration direction of the incident linear polarization light is parallel to the alignment direction, and the baseline is taken. Then, the dye liquid crystal cell is adjusted so that the vibration direction of the incident linear polarization light is parallel to the alignment direction, and the absorbance peak A is measured. ∥ , record A ∥ The corresponding wavelength is λ max Then rotate the polarizing prism or CELL by 90° so that the vibration direction of the linear polarized light incident on the CELL is perpendicular to the alignment direction, and measure λ using the same method. max A at wavelength ⊥ The dichroic ratio and order parameter were calculated according to the following formula.

[0311] Dichroic ratio (D) calculation formula:

[0312] D=A ∥ / A ⊥ ;

[0313] Order parameter (S) calculation formula:

[0314] S=(A ∥ -A ⊥ ) / (2A ⊥ +A ∥ ).

[0315] (2) Measure HTP value

[0316] Add different concentrations of dichroic dye (adjust the actual solubility if the solubility is less than 1%) to liquid crystal composition A and mix thoroughly (total amount is 100%). Heat and stir until the liquid crystal becomes clear. Turn off the heat and stir until the temperature reaches room temperature. Use a dropper to draw the liquid crystal to be tested and drop it onto the side of the wedge-shaped cell. Once the filling is complete, place the wedge-shaped cell flat and let it stand for 12 hours.

[0317] Select a section of uniform staggered lines through a reading microscope, first align the crosshairs with one staggered line X1, record the reading, turn the left and right rotation rods, align it with another staggered line X2, and record the reading. In this way, record the reading of each line of the selected uniform staggered line, and the difference between two adjacent staggered lines will be △X;

[0318] Pitch P = 2 × ΔX × tan × 1000 (μm), tan = 0.0196.

[0319] HTP=1 / CP, C is the mass concentration (%) of the dichroic dye in the liquid crystal composition.

[0320] (3) Measuring the handedness of organic compounds

[0321] Prepare a chiral agent mixed solution: add 1 wt % of the organic matter provided in Examples 1-17 of the present invention (when the solubility is lower than 1%, prepare according to the actual solubility) to 99 wt % of liquid crystal composition A to prepare a dye liquid crystal with a test organic matter content of 1 wt %.

[0322] Mix 99 wt% of the dye liquid crystal to be tested (the organic compound provided in Examples 1 to 17 of the present invention, with a solid content of 1 wt%) with 1 wt% of the chiral agent CB15. Use a dropper to draw up the mixture and drip it onto the side of the wedge-shaped box. After the filling is completed, lay the wedge-shaped box flat and let it stand for 12 hours.

[0323] Identifying left-hand and right-hand helical rotation: Using a reading microscope and following the HTP value measurement method, read the difference ΔX between the two staggered lines and calculate the pitch P1. Then, test the pitch P2 of a comparative liquid crystal composed of 1wt% CB15 and 99% liquid crystal mixture A. CB15 is known to be right-handed. If the pitch P1 is less than P2, the measured example is right-handed; if the pitch P1 is greater than P2, the measured example is left-handed.

[0324] The specific test results are shown in Table 3.

[0325] Table 3

[0326] Note: “ / ” indicates that no clear phase misalignment line was observed during the test and the HTP value could not be calculated.

[0327] (4) Solubility test

[0328] Solubility testing method: The organic compound to be tested is mixed with liquid crystal composition A at a gradient of concentrations to form dye liquid crystals with varying dye concentrations. Each liquid crystal is then poured into a 10-micron liquid crystal cell and placed at 25°C for 15 days. Microscopic observation is then made to detect crystal precipitation. The average of the two concentrations, the one where no precipitation occurred and the one where precipitation occurred, is used for a second round of testing. If no precipitation occurs, the average is used as the final solubility. If precipitation occurs, the concentration where no precipitation occurred is used as the solubility. For examples with solubility ≥ 1%, the concentration gradient is 0.1; for examples with solubility < 1%, the concentration gradient is 0.05.

[0329] Taking the organic compounds provided in Examples 4, 10, 12, and 13 as examples, the test results are shown in Table 4.

[0330] Table 4

[0331] Note: The parent liquid crystals are all liquid crystal composition A

[0332] As can be seen from Tables 3 and 4, the organic compounds provided by the present invention, through a specific molecular structure design, introduce chiral groups of specific structures into the molecular chain. As dichroic dyes, while providing a chiral effect, the branched structure can increase the solubility of the dye itself. This not only improves the solubility of the dye in the liquid crystal composition, but also reduces the use of chiral agents, or even eliminates the need for the addition of chiral agents, thereby reducing costs and avoiding the problem of low solubility caused by chiral agents. At the same time, compared with conventional chiral agents, the organic compounds provided by the present invention have a high dichroic ratio and order parameter, which is beneficial for improving the order, contrast, and color reproducibility of the liquid crystal composition, thereby obtaining a high-quality liquid crystal device. The liquid crystal composition including the organic compound has a dichroic ratio of 7 to 14 and an HTP value of 0.8 to 4.3.

[0333] The specific embodiments described above further illustrate the objectives, technical solutions and beneficial effects of the present invention in detail. It should be understood that the above are only specific embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. An organic compound, characterized in that The molecular structure of the organic compound includes a chromophore and a chiral group connected to the chromophore via a chemical bond.

2. The organic compound according to claim 1, characterized in that The organic compound has a structure shown in Formula I: wherein A is selected from a chromophore; Z is selected from a single bond, -O-, -S-, -NR N1 -、-NR N2 -CR C1 -, -O-CO-, -CO-O-, -CO-O-CR C1 R C2 -、-CR C3 R C4 -, -C=N-, -N=C-, -C≡C-, -CR C5 =CR C6 -、-CO-、-O-CR C7 R C8 -、-CR C9 R C10 Any one of -O-, -SO- or -SO2-; R1, R2, and R3 are each independently selected from any one of H, -C≡CH, a C1-C10 straight-chain or branched alkyl group, a C6-C12 aryl group, or a cholesterol ester group, and R1, R2, and R3 are each different; n is selected from an integer ≥ 1; and when n is greater than 1, the chiral groups may be the same or different; R N1 、R N2 、R C1 、R C2 、R C3 、R C4 、R C5 、R C6 、R C7 、R C8 、R C9 、R C10 Each independently selected from H or a C1-C6 straight or branched alkyl group; "*" indicates that the carbon atom is chiral carbon.

3. The organic compound according to claim 1, characterized in that R1, R2, and R3 are each independently selected from any one of H, a C1-C6 straight-chain alkyl group, a phenyl group, or a cholesterol ester group, and R1, R2, and R3 are different; Said n is selected from an integer of 1 to 5; Group Connected to any position of A, the dotted line indicates the connection site.

4. The organic compound according to claim 1, characterized in that Group Connected to the end of A's molecular chain.

5. The organic compound according to claim 1, characterized in that Among the organic compounds, At least one selected from the following groups: Dashed lines indicate the junction sites.

6. The organic compound according to claim 1, characterized in that The A is selected from rigid chromophores.

7. The organic compound according to claim 6, characterized in that The rigid chromophore is selected from dichroic rigid chromophores.

8. The organic compound according to claim 7, characterized in that The dichroic rigid chromophore is selected from any one of a dichroic azo chromophore, a dichroic rylene group or a dichroic heterocyclic chromophore.

9. The organic compound according to claim 8, characterized in that The dichroic azo chromophore group has a structure shown in Formula II; Ar1-N=N-[Ar2-N=N] a -[Ar3-N=N] b -[N=C] c -[Ar4-N=N] d -Ar5 Formula II; wherein Ar1 and Ar5 are each independently selected from any one of a substituted or unsubstituted C6-C12 aryl group or a substituted or unsubstituted C2-C10 heteroaryl group; Ar2, Ar3, Ar4 are each independently selected from substituted or unsubstituted C6-C12 arylene groups; The substituted substituents include halogen, -CF3, -OCF3, sulfo, carboxyl, hydroxyl, nitro, cyano, phosphate, C1-C18 straight or branched alkyl, C6-C18 aryl, C2-C18 amide, formyl, -COOR A1 、-COR A2 、-SO2R A3 、-CONR A4 R A5 、-NR A6 R A7 , any one of C1~C12 alkoxy, C3~C12 cycloalkyl, C1~C12 alkylthio or C2~C10 heteroaryl; at least one H in the C1~C18 straight or branched alkyl, C1~C12 alkoxy, C1~C12 alkylthio, C3~C12 cycloalkyl can be independently substituted by any one of amino, halogen, and cyano; at least one H in the C6~C18 aryl can be substituted by any one of amino, cyano, halogen, C1~C8 straight or branched alkyl, C1~C8 straight or branched haloalkyl; at least one CH2, CH in the C1~C18 straight or branched alkyl, C1~C12 alkoxy, C3~C12 cycloalkyl can be independently substituted by -O-, -NR N1 - or -S- substituted; at least one H in the C2-C10 heteroaryl group may be substituted by a substituent, and the range of the substituent is the same as the range of the aforementioned substituent; The substituents can be connected to form a ring by chemical bonds; the substituents and the ring structure connected to them can be connected by a single bond, -O-, -S- or -NR N2 - connected into a ring; R A1 、R A2 、R A3 Each independently selected from C1-C12 straight or branched alkyl, C3-C18 cycloalkyl, C6-C12 aryl, Any one of the C1 to C12 linear or branched alkyl groups; at least one H may be substituted by halogen, cyano or hydroxyl; at least one H in the C3-C18 cycloalkyl group may be substituted by halogen, cyano, hydroxyl or C1-C12 haloalkyl; at least one CH2 or CH in the C3-C18 cycloalkyl group may be replaced by O; at least one H in the C6-C12 aryl group may be substituted by halogen, cyano, hydroxyl, C1-C12 alkyl or C1-C12 haloalkyl; R A11 is selected from C3-C18 cycloalkyl, wherein at least one H in the C3-C18 cycloalkyl may be substituted by halogen, cyano or hydroxyl; R A12 is selected from H, halogen, cyano or hydroxy; R A13 is selected from C3-C18 cycloalkylene, wherein at least one H in the C3-C18 cycloalkylene may be substituted by halogen, cyano, hydroxyl, C1-C12 alkyl or C1-C12 haloalkyl; R A14 is selected from H, halogen, cyano, hydroxy, C1-C12 alkyl or C1-C12 haloalkyl; Dashed lines indicate junction sites; R A4 、R A5 、R A6 、R A7 Each is independently selected from any one of H, C1-C8 alkyl, C3-C12 cycloalkyl, phenyl or chiral group; R A4 With R A5 、R A6 With R A7 Can be independently connected by a single bond, -O-, -S- or -NR N2 - connected into a ring; R N1 、R N2 Each independently selected from H or C1-C8 alkyl; a, b, and d are each independently selected from integers of 0 to 2; and c is selected from 0 or 1.

10. The organic compound according to claim 9, characterized in that Ar1 and Ar5 are each independently selected from the following groups, or any one of the following groups substituted by a substituent: The substituents are selected from the same range as Formula II; the number of the substituents is 1 or 2; and the dotted line represents the connection site.

11. The organic compound according to claim 10, characterized in that When c and d are each independently 0, or when c is 1 and d is 1, Ar5 is selected from the following groups, or any one of the following groups substituted by a substituent: The substituent is selected from -NR A6 R A7 , C1 to C8 linear or branched alkyl, phenyl, halogen or cyano, wherein R A6 、R A7 Each is independently selected from any one of H, C1-C4 alkyl, C3-C12 cycloalkyl, phenyl or chiral group; R A6 With R A7 Can be separated by single bond, -O-, -S- or -NR N2 - connected into a ring; the dotted line indicates the connection site; When c is not 0 and d is 0, Ar5 is selected from the following groups, or any one of the following groups substituted by a substituent: The substituents include C1-C12 alkyl, C1-C12 alkoxy, C1-C12 alkylthio, hydroxy, halogen, nitro, cyano, -COOR A1 、-COR A2 、-SO2R A3 、-CONR A4 R A5 、-NR A6 R A7 , C6-C12 aryl, C2-C10 heteroaryl or C3-C18 cycloalkyl; at least one H in the C1-C12 alkyl, C1-C12 alkoxy and C1-C12 alkylthio group can be independently substituted by halogen, hydroxyl or amino; at least one CH2 and CH in the C1-C12 alkyl, C1-C12 alkoxy and C3-C18 cycloalkyl group can be independently replaced by -O-, -NR- or -S-; at least one H in the C6-C12 aryl and C2-C10 heteroaryl group can be independently replaced by cyano, halogen, hydroxyl, -NR- A6 R A7 , C1~C12 alkyl, C1~C12 alkoxy, C1~C12 alkylthio; at least one H in the C3~C18 cycloalkyl group may be replaced by C1~C12 haloalkyl, halogen, CN, OH, C1~C12 alkoxy, C1~C12 alkylthio or -NR A6 R A7 Substitution; the substituent may form a 5-7 membered heterocyclic structure with the ring structure to which it is connected, wherein the heterocyclic structure contains at least one heteroatom, which is selected from at least one of O, S, and NR; at least one H in the heterocyclic structure may be replaced by a C1-C4 alkyl, Substitution; R is selected from C1~C12 alkyl, C3~C12 cycloalkyl or phenyl; at least one H in the phenyl group may be substituted by C1~C6 alkyl, F or CN.

12. The organic compound according to claim 9, characterized in that Ar2, Ar3, and Ar4 are each independently selected from the following groups, or any one of the following groups substituted by a substituent: The substituent is selected from any one of a C1-C4 straight-chain or branched alkyl group, a C1-C4 alkoxy group, a halogen, a cyano group, a sulfo group, a carboxyl group, an amino group, a phenyl group or a C2-C8 amide group; at least one H in the C1-C4 straight-chain or branched alkyl group, the C1-C4 alkoxy group or the phenyl group can be independently replaced by an amino group, a halogen, a hydroxyl group or a cyano group; the dotted line indicates the connection site.

13. The organic compound according to claim 8, characterized in that The dichroic rylene group has a structure shown in formula III: Wherein, X1, X2, Y1, Y2 are each independently selected from H or -COOM; and at least one of X1, X2, Y1, Y2 is selected from -COOM; X1 and X2, Y1 and Y2 can each independently be connected to form a ring (a), ring (b) or ring (c) as shown in the following structure: structure; Dashed lines indicate fusion sites; R N Any one selected from H, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl; -O-, -S-, -NR- can be inserted into the carbon skeleton of the C1-C30 straight or branched alkyl 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; the C3-C8 cycloalkyl, C6-C20 aryl or C6-C20 heteroaryl may be fused with a 5-7 membered saturated ring or a 5-7 membered unsaturated ring; the carbon skeleton of the 5-7 membered saturated ring or the 5-7 membered unsaturated ring may be inserted with -O-, -S-, -NR 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one H in the C6-C20 aryl or C6-C20 heteroaryl may be substituted by an azo group; R 21 is selected from hydrogen or C1-C18 straight or branched chain alkyl, wherein R 21 When the group appears more than once, it may be the same or different; Z is selected from any one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted pyridinylene; M is selected from H, halogen or -B(OR B )2; R B Any one selected from H, substituted or unsubstituted C1-C30 straight or branched alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C6-C20 heteroaryl; M, ring (a), ring (b) or ring (c) may each independently be connected to a chiral group; R is selected from any one of substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 arylthio, substituted or unsubstituted C6-C30 heteroaryloxy, and substituted or unsubstituted C6-C30 heteroarylthio; the C6-C30 aryloxy, C6-C30 arylthio, C6-C30 heteroaryloxy, and C6-C30 heteroarylthio may each independently be fused to a 5-7 membered saturated ring or a 5-7 membered unsaturated ring; the carbon skeleton of the 5-7 membered saturated ring or the 5-7 membered unsaturated ring may be inserted with -O-, -S-, or -NR 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2- at least one; The number of the substituted substituents is at least one; the substituted substituents include C1-C30 straight chain or branched alkyl, C3-C8 cycloalkyl, C6-C20 aryl, C5-C20 heteroaryl, -U-aryl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 22 、-CR 22 =C(R 23 )2, hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 or-POR 22 R 23 at least one of; In the substituents, -O-, -S-, -NR- 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the C1-C30 straight or branched alkyl groups may be replaced by a C1-C12 alkoxy group, a C1-C6 alkylthio group, a -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 , aryl, C1~C18 alkyl substituted aryl, C4~C7 saturated or unsaturated cycloalkyl, C1~C18 alkyl substituted C4~C7 saturated or unsaturated cycloalkyl; the carbon skeleton of the C4~C7 saturated or unsaturated cycloalkyl may be inserted with one or more -O-, -S-, -NR 21 -、-N=CR 21 -、-CR 21 =CR 21 -, -CO-, -SO-, -SO2-; the C3-C8 cycloalkyl group may be fused with a 5- to 7-membered saturated or unsaturated ring; the carbon skeleton of the 5- to 7-membered saturated or unsaturated ring may be inserted with -O-, -S-, -NR 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the 5- to 7-membered saturated or unsaturated rings may be C1-C8 alkyl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 At least one substitution in In the substituents, C6-C20 aryl, C6-C20 heteroaryl, -U-aryl can be fused with a 5-7 membered saturated or unsaturated ring; -O-, -S-, -NR- can be inserted into the carbon skeleton of the 5-7 membered saturated or unsaturated ring. 21 -、-N=CR 21 -、-C≡C-、-CR 21 =CR 21 -, -CO-, -SO- or -SO2-; at least one of the C6-C20 aryl, C6-C20 heteroaryl, -U-aryl, 5-7 membered saturated or unsaturated rings, at least one H of which may be C1-C18 alkyl, C1-C12 alkoxy, C1-C6 alkylthio, -C≡CR 21 、-CR 21 =CR 21 R 22 , hydroxyl, thiol, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 、-POR 22 R 23 , aryl or heteroaryl, wherein the aryl or heteroaryl is independently substituted by C1-C18 alkyl, C1-C12 alkoxy, hydroxyl, mercapto, halogen, cyano, nitro, -NR 22 R 23 、-NR 22 COR 23 、-CONR 22 R 23 、-SO2NR 22 R 23 、-COOR 22 、-SO3R 22 、-PR 22 R 23 or-POR 22 R 23 At least one substitution in In the above substituents, -U- represents -O-, -S-, or -NR 21 -, -CO-, -SO- or -SO2-; R 22 、R 23 are each independently selected from H; m is selected from integers of 0 to 4; n is selected from integers of 1 to 8.

14. The organic compound according to claim 13, characterized in that When m is 1, n is selected from an integer of 3 to 6; when m is 2, n is selected from an integer of 2 to 8.

15. The organic compound according to claim 8, characterized in that The dichroic heterocyclic chromophore has a structure shown in Formula IV, and at least one H in the structure shown in Formula IV is Substitution; Ar 23 -L3-(Ar 22 -L2) x -Ar 21 -L1-PL 1′ -Ar 21′ -(L 2′ -Ar 22′ ) x′ -L 3′ -Ar 23′ Formula IV Wherein, P is selected from any one of the following structures; the straight line represents the connection site; L1, L 1′ Each independently represents a single bond, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -N=N-, -CH=N-, -N=CH-, -N=N(O)-, -N(O)=N-, -CR 31 =CR 31 -、-(CR 31 =CR 31 )2-, -C≡C-, -CF=CF-, -C(=O)-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -CH=CH-COO- or -OCO-CH=CH-; L2, L 2′ Each independently represents a single bond, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -N=N-, -CH=N-, -N=CH-, -N=N(O)-, -N(O)=N-, -CR 31 =CR 31 -、-(CR 31 =CR 31 )2-、-C≡C-、 -CF=CF-, -C(=O)-, -CH=CH-C(=O)-, -C(=O)-CH=CH-, -CH=CH-COO-, -OCO-CH=CH-, -O-, -S-, -C(R 31 )2-, -C(O)-O-, -OC(O)-, -OC(O)-O-, -SCH2-, -CH2S-, -CF2S-, -SCF2-, -(CH2) n1 -, -CF2CH2-, -CH2CF2- or -(CF2) n1 -; n1 represents an integer greater than or equal to 1; L3, L 3′ Each independently represents a single bond, -O-, -S-, -C(R 31 )2-、-C(R 31 )2O-、-OC(R 31 )2-、-CR 31 =CR 31 -, -C≡C- or a combination of at least two of the above groups; Ar 21 、Ar 22 、Ar 23 、Ar 21′ 、Ar 22′ 、Ar 23′ Each independently selected from unsubstituted or substituted by at least one R 32 Substituted C5-C30 aryl, unsubstituted or replaced by at least one R 32 Any one of substituted C5-C30 heteroaryl groups; R 31 、R 32 Each independently represents H, D, F, Cl, -CN, -N(R 33 )2, C1-C15 straight chain or branched alkyl, C1-C15 straight chain or branched alkoxy, C1-C15 straight chain or branched thioalkoxy, C2-C15 straight chain or branched alkenyl, C2-C15 straight chain or branched alkynyl, C5-C30 aryl or C5-C30 heteroaryl, wherein at least one H in the above groups can be replaced by R 33 Substitution, at least one CH2 group in the above groups can be replaced by -R 33 C=CR 33 -, -C≡C-, -C=O-, -C=S-, -C(=O)O-, -O(C=O)-, -Si(R 33 )2-、-NR 33 -, -O-, or -S- substitution; R in different groups 33 Same or different, represents H, D, F, Cl, -CN, -N(R 34 )2, C1-C15 straight chain or branched alkyl, C1-C15 straight chain or branched alkoxy, C1-C15 straight chain or branched thioalkoxy, C2-C15 straight chain or branched alkenyl, C2-C15 straight chain or branched alkynyl, C5-C30 aryl or C5-C30 heteroaryl, wherein at least one H in the above groups can be replaced by R 34 Substitution, at least one CH2 group in the above groups can be replaced by -R 34 C=CR 34 -, -C≡C-, -CO-, -CS-, -C(=O)O-, -O(C=O)-, -Si(R 34 )2-、-NR 34 -, -O-, or -S- substitution; R in different groups 34 The same or different, represents H, F, a C1-C20 aliphatic organic group, a C5-C20 aryl group, or a C5-C20 heteroaryl group; at least one H in the C1-C20 aliphatic organic group, a C5-C20 aryl group, or a C5-C20 heteroaryl group may be replaced by F; E1 and E2 are each independently selected from O or -NR 39 ; R in different groups 39 、R 40 are the same or different, each independently representing H, D, F, Cl, -CN, -N(R 41 )2, C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C2~C15 straight chain or branched alkynyl, C5~C30 aryl or C5~C30 heteroaryl, wherein at least one H in the C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C1~C15 straight chain or branched alkynyl can be replaced by R 41 or R 50 At least one CH2 can be replaced by -R 41 、-C=CR 41 -, -C≡C-, -C=O-, -C=S-, -C(=O)O-, -O(C=O)-, -Si(R 41 )2-、-NR 41 -, -O- or -S-; at least one H in the C5-C30 aryl or C5-C30 heteroaryl may be replaced by R 50 replace; R in different groups 41 Same or different, represents H, D, F, Cl, -CN, -N(R 42 )2, C1~C15 straight chain or branched alkyl, C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C2~C15 straight chain or branched alkynyl, C5~C30 aryl or C5~C30 heteroaryl, wherein at least one H in the C1~C15 straight chain or branched alkoxy, C1~C15 straight chain or branched thioalkoxy, C2~C15 straight chain or branched alkenyl, C1~C15 straight chain or branched alkynyl can be replaced by R 60 Substituted, at least one CH2 group may be -R 42 C=CR 42 -, -C≡C-, C=O, C=S, -C(=O)O-, -O(C=O)-, -Si(R 42 )2-、-NR 42 -, -O- or -S-, at least one H in the C5-C30 aryl or C5-C30 heteroaryl may be replaced by R 42 replace; R in different groups 42 The same or different, represents H, F, C1 to C20 aliphatic organic group, C5 to C20 aryl group or C5-C20 heteroaryl; at least one H in the C1-C20 aliphatic organic group, C5-C20 aryl group, or C5-C20 heteroaryl group may be replaced by F; R in different groups 50 Same or different, represents H, F, -CN, -CO-, -N(R 51 )2, -SO2R 51 , -CH=C(CN)2, any one of C1-C25 straight or branched alkyl, C3-C20 cycloalkyl, wherein one or more non-adjacent CH2, CH in C1-C25 straight or branched alkyl, C3-C20 cycloalkyl can be replaced by -O-, -S-, -C(R 51 )=C(R 51 )-、-C≡C-、-N(R 51 )-, -CO-, -CO-O-, -O-CO- or -O-CO-O-, and at least one H may be replaced by F, Cl, Br, I or CN; R in different groups 51 Same or different, R 51 、R 60 Each is independently selected from any one of H, halogen, C1-C12 linear or branched alkyl, and C3-C12 cycloalkyl, wherein one or more non-adjacent CH2 or CH in the C1-C12 linear or branched alkyl or C3-C12 cycloalkyl may be replaced by -O-, -S-, -CO-, -CO-O-, -O-CO-, or -O-CO-O-, and at least one H may be replaced by F or Cl; W is selected from O, S or Se; x and x' are each independently selected from integers of 0 to 4, and when x and x' are greater than 1, Ar 22 Can be the same or different; Ar 22′ Can be the same or different.

16. The organic compound according to claim 15, characterized in that The L1, L 1′ , L2, L 2′ Each is independently selected from a single bond, -N=N-, -CH2CH2-, -CF2CF2-, -OCH2-, -OCF2-, -CH2O-, -CF2O-, -CH=CH-, -CF=CF- or -C≡C-.

17. The organic compound according to claim 16, characterized in that When P is L1, L 1′ For a single bond.

18. The organic compound according to claim 15, characterized in that R 39 Selected from -CN; R 40 Selected from H, unsubstituted or replaced by R 50 Substituted C1-C15 straight-chain or branched alkyl, C5-C18 aryl or C5-C18 heteroaryl.

19. The organic compound according to claim 15, characterized in that R 50 Selected from -CN, C1-C12 straight chain alkyl, C1-C15 straight chain alkoxy, C3-C25 branched chain alkyl or C3-C25 branched chain alkoxy.

20. The organic compound according to claim 15, characterized in that R 50 is selected from n-pentyl, n-hexyl, n-heptyl, 2-ethylhexyl, 2-ethylheptyl, 2-ethyloctyl, 2-ethylnonyl, 2-ethyldecyl, 3-ethylhexyl, 3-ethylheptyl, 3-ethyloctyl, 3-ethylnonyl, 3-ethyldecyl, 2-octyldodecyl or -CN.

21. The organic compound according to claim 15, characterized in that R 60 A straight chain alkyl group selected from C1 to C9.

22. The organic compound according to claim 15, characterized in that R 60 Selected from ethyl.

23. The organic compound according to claim 1, characterized in that The organic compound is selected from any one of the following structural compounds; Here, "*" indicates that the carbon atom is chiral carbon.

24. A chiral dichroic dye, characterized in that The chiral dichroic dye includes at least one organic compound according to claim 1 .

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