Organic compounds and use thereof

Abstract

Provided in the embodiments of the present application are organic compounds and the use thereof. The organic compounds have a structural general formula as shown in formula (I), wherein A represents an electron acceptor, D represents an electron donor, Z is a sulfur atom, an oxygen atom or NH, R1 is selected from substituted or unsubstituted C1-C10 alkylene groups, n is an integer selected from 0-2, X1 comprises at least one first crosslinkable group, X2 comprises at least one second crosslinkable group, and a cycloaddition crosslinking reaction can occur between the first crosslinkable group and the second crosslinkable group. The organic compounds having said structural characteristics can simultaneously have relatively high glass transition temperatures and relatively high electro-optic coefficients, polarization efficiency, etc., and thus can be used for electro-optic active films, electro-optic devices, etc. having excellent performance.

Description

Organic compounds and their applications

[0001] This application claims priority to the Chinese patent application filed with the State Intellectual Property Office of China on August 17, 2023, with application number 202311052596.5 and application name “Organic Compounds and Their Applications”, the entire contents of which are incorporated by reference into this application. Technical Field

[0002] The embodiments of the present application relate to the technical field of organic electro-optical materials, and in particular to an organic compound and its application. Background Art

[0003] Electro-optic modulators are core devices for photoelectric information conversion and are crucial for overcoming the two major technical challenges of bandwidth and energy consumption in optical communication networks. Electro-optic materials, as the core components of electro-optic modulators, have attracted widespread attention. Organic electro-optic materials are considered promising due to their advantages, such as molecular-level structural design, higher electro-optic coefficients than the inorganic optical material lithium niobate, faster response speeds, and good processability.

[0004] According to the interaction between molecules of organic electro-optical materials after polarization orientation, organic electro-optical materials can be divided into self-assembly type and cross-linking type. Among them, cross-linking electro-optical materials have become a research hotspot in recent years due to their high stability in polarization orientation. Existing cross-linking electro-optical materials usually include chromophores and cross-linking agents (such as small molecules, polymers), or include at least two chromophores, but the content of the effective active ingredient - chromophore in the former is low, and the room for improving the electro-optic coefficient is limited, while the latter can better improve the electro-optic coefficient. Among them, the binary chromophore cross-linking system requires the two chromophores to be adjusted in ratio and then mixed, which is cumbersome to operate, and the glass transition temperature (T g ) usually have differences, resulting in uncertainty in the polarization process and cumbersome polarization steps. Therefore, it is necessary to develop a new cross-linked electro-optical material that is more conducive to practical applications.

[0005] Summary of the Invention

[0006] In view of this, an embodiment of the present application provides a self-crosslinking organic compound, in which a cycloaddition crosslinking reaction can occur between the two crosslinkable groups, thereby avoiding the problem of needing to regulate the ratio of the two chromophores and the difficulty in matching the Tg of the two chromophores in a binary chromophore crosslinking system.

[0007] Specifically, the first aspect of the embodiment of the present application provides an organic compound having the general structural formula shown in formula (I):

[0008] In formula (I), A represents an electron acceptor, D represents an electron donor, Z is a sulfur atom, an oxygen atom or NH, and R1 is selected from substituted or unsubstituted C1-C 10 Alkylene; n is an integer selected from 0-2; X1 includes at least one first crosslinkable group, X2 includes at least one second crosslinkable group, and a cycloaddition crosslinking reaction can occur between the first crosslinkable group and the second crosslinkable group.

[0009] In the organic compound provided in the embodiments of the present application, the two cross-linkable groups that can react with each other are covalently linked to the same chromophore (i.e., the organic compound). This makes the organic compound a self-crosslinking chromophore. When using it to prepare an electro-optically active film, there is no need to introduce a second chromophore, thus avoiding the problems of adjusting the ratio of the two chromophores and the difficulty in matching the Tg of the two chromophores. Furthermore, the electro-optically active film prepared using this self-crosslinking organic compound has both a high electro-optic coefficient and thermal stability, which is conducive to the actual stable and efficient operation of the electro-optical device.

[0010] In some embodiments of the present application, Z is a sulfur atom and R1 is -CH2-CH2. In this case, the organic compound represented by formula (I) is easier to synthesize and has a higher yield.

[0011] In an embodiment of the present application, the first crosslinkable group and the second crosslinkable group are independently selected from one or more of anthracene, acrylate, maleamide, furanyl, aryl azide, and alkynyloxy groups. In this case, the first crosslinkable group and the second crosslinkable group must still be capable of undergoing a cycloaddition crosslinking reaction.

[0012] In some embodiments of the present application, X1 and X2 are independently selected from One or more of the following; the position marked with * is the connection position.

[0013] In the embodiment of the present application, the D independently comprises an aromatic amine structure or a heteroaromatic amine structure containing a tertiary ammonia nitrogen atom. D containing a tertiary ammonia nitrogen atom may have a strong electron-donating ability.

[0014] In some embodiments of the present application, A is specifically X is an oxygen atom, a sulfur atom, NH or CH2. The organic compound represented by formula (I) having this A is relatively easy to synthesize.

[0015] A second aspect of the embodiments of the present application provides a film, which includes a cross-linked product of the organic compounds described above in the embodiments of the present application.

[0016] In some embodiments of the present application, the film is an electro-optically active film having an electro-optic coefficient greater than or equal to 190 pm / V and a glass transition temperature greater than or equal to 150°C. This electro-optically active film can achieve both high thermal stability and electro-optic coefficient, making it suitable for manufacturing components for optical communication systems that require high thermal stability.

[0017] A third aspect of the present application also provides a method for preparing an electro-optically active thin film, comprising the following steps:

[0018] Applying a solution containing the organic compound of the embodiment of the present application on a substrate and drying it to form a film layer;

[0019] applying an electric field to the film layer and heating it at a first temperature to polarize the organic compound;

[0020] The polarized film layer is further heated to a second temperature to allow the organic compound to self-crosslink, and then the temperature is lowered to obtain an electro-optically active thin film.

[0021] The electro-optical active film obtained through the above-mentioned polarization and cross-linking steps has high polarization stability and high glass transition temperature, can work stably for a long time at a relatively high temperature, and is particularly suitable for the production of electro-optical devices.

[0022] The fourth aspect of the embodiments of the present application also provides the use of the above-mentioned organic compounds, the above-mentioned films, and the electro-optically active films prepared by the above-mentioned methods for preparing electro-optically active films in the embodiments of the present application in components of optical communication systems, solar cells, organic electroluminescent devices, and organic photoluminescent devices.

[0023] The components of the optical communication system include one or more of electro-optical devices, optical switches, straight waveguides, bent waveguides, single-mode optical splitters, routers, filters, optical interconnectors, and resonators.

[0024] The embodiments of the present application also provide an electro-optical device, comprising the film described above in the embodiments of the present application, or an electro-optical active film prepared using the method for preparing the electro-optical active film described above in the embodiments of the present application.

[0025] In an embodiment of the present application, the electro-optical device includes one or more of an electro-optic modulator, a coupler, a terahertz detector, an electro-optic frequency shifter, and a frequency comb source. The electro-optical modulator includes one or more of a Mach-Zehnder modulator, a phase modulator, a silicon-organic hybrid modulator, and a plasma-organic hybrid modulator.

[0026] The embodiments of the present application also provide an optical communication system, at least some components of the optical communication system include the film described above in the embodiments of the present application, or an electro-optically active film prepared using the method for preparing the electro-optically active film described above in the embodiments of the present application.

[0027] An embodiment of the present application also provides a phased array lidar system, which includes the film described above in the embodiment of the present application, or an electro-optical active film prepared using the method for preparing the electro-optical active film described above in the embodiment of the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] FIG1 is a schematic structural diagram of an electro-optic modulator provided in an embodiment of the present application.

[0029] FIG2A is a thermogravimetric curve of the chromophore SLD1 provided in Example 1 of the present application.

[0030] FIG2B is a thermogravimetric curve of the chromophore SLD2 provided in Example 2 of the present application.

[0031] FIG3 shows the UV-visible spectra of the chromophore SLD1 in different solvents and films.

[0032] FIG4 shows the UV-visible spectra of the chromophore SLD2 in different solvents and films.

[0033] FIG5 is a schematic diagram showing the electro-optic coefficient of an electro-optically active film tested using the Teng-Man simple reflection method.

[0034] FIG6 shows the polarization curve of the film of chromophore SLD1 after self-crosslinking.

[0035] FIG7 shows the polarization curve of the film of chromophore SLD2 after self-crosslinking. DETAILED DESCRIPTION

[0036] The technical solutions of the embodiments of the present application are described in detail below.

[0037] Given the problems of existing binary chromophore cross-linking systems, such as the need to regulate the ratio of the two chromophores and the difficulty in matching the Tg of the two chromophores, which leads to a cumbersome polarization process, the present invention provides a self-crosslinking organic compound. The term "chromophore" refers to a compound that can absorb light within a certain wavelength peak and produce a certain color. The organic compound provided in this application is also a chromophore.

[0038] Specifically, the organic compound provided in the examples of the present application has the general structural formula shown in formula (I):

[0039] In formula (I), A represents an electron acceptor, D represents an electron donor, Z is a sulfur atom (S), an oxygen atom (O) or NH, and R1 is selected from substituted or unsubstituted C1-C 10 Alkylene; n is an integer selected from 0-2; X1 includes at least one first crosslinkable group, X2 includes at least one second crosslinkable group, and a cycloaddition crosslinking reaction can occur between the first crosslinkable group and the second crosslinkable group.

[0040] In the above-mentioned organic compound provided by the present application, the two cross-linkable groups are respectively connected to the same chromophore (i.e., the organic compound) by means of covalent bonds, and the two cross-linkable groups can undergo a cycloaddition cross-linking reaction with each other, which makes the organic compound a self-cross-linking chromophore with high polarization orientation. When the organic compound is used to prepare an electro-optically active film, the polarized organic compound itself can undergo a cross-linking reaction to obtain an electro-optically active film with a high electro-optical coefficient, without the need to introduce an external substance as a cross-linking agent, for example, without the need to introduce a second chromophore that can undergo a cross-linking reaction with the organic compound, which avoids the problem of regulating the ratio of the two chromophores and the existence of the problem of the T of the two chromophores. g The polarization process is complicated and unstable due to the difficulty in matching. Moreover, since the organic compound can self-crosslink, the crosslinking density of its crosslinked product is large, and the T of the electro-optical active film containing its crosslinked product is large. g It is relatively high and is not easily stimulated by high temperatures and loses its electro-optical activity. It is suitable for making electro-optical devices that can operate stably at high temperatures and can meet the communication industry's requirements for the thermal stability of electro-optical devices.

[0041] In addition, the electro-optical activity of cross-linked organic electro-optical materials is usually achieved by applying an electric field to polarize their molecules. Generally, an electric field is applied to a dry film containing the organic electro-optical material and the dry film is heated to a temperature close to the glass transition temperature T of the organic electro-optical material. g , so that its molecules are reoriented and its dipole moment is aligned with the electric field, and then it is further heated to the crosslinking temperature of the organic electro-optical material to cause intermolecular crosslinking and thus stabilize the already polarized molecules; then it is cooled while the electric field is still in place to maintain the polarization induction and obtain an electro-optically active film. However, if the electro-optically active film is heated again to a temperature close to the T g When the electro-optical activity is lost, the glass transition temperature T g Also higher, the T g The temperature difference between the crosslinking temperature and the crosslinking temperature is appropriate, and the crosslinked organic compound can smoothly exhibit electro-optical activity through polarization and crosslinking; and the T g The electro-optical active film containing the cross-linked product can withstand higher temperatures without losing its electro-optical activity. Therefore, the organic compound provided by the present application can take into account both high electro-optical coefficient and high Tg The electro-optical active film produced by it also has high electro-optical coefficient and high thermal stability.

[0042] In the present application, the first crosslinkable group and the second crosslinkable group may be reactive groups capable of crosslinking by (4+2) or (3+2) cycloaddition. Exemplarily, the first crosslinkable group and the second crosslinkable group may independently include, but are not limited to, one or more of anthracene, acrylate, maleamide, furanyl, aryl azide, alkynyloxy, or derivatives thereof, but need to satisfy the requirement that a cycloaddition crosslinking reaction can occur between the first crosslinkable group and the second crosslinkable group.

[0043] Specifically, an anthracene group can crosslink with an acrylate group or a maleamide group via a (4+2) cycloaddition reaction; a maleamide group can crosslink with a furan group via a (4+2) cycloaddition reaction; and an azidoaryl group can crosslink with an alkynyloxy group via a (3+2) cycloaddition reaction. The presence of reactive groups capable of undergoing cycloaddition crosslinking reactions ensures that the crosslinking temperature of the organic compound is greater than its Tg, facilitating polarization under electric field stimulation and subsequent crosslinking to stabilize the orientation of the polarized molecules and maintain stable electro-optical activity. By regulating the X1 and X2 groups with crosslinkable groups, the variety of organic compounds can be enriched. The acrylate group or its derivative group can include CH2=CH-COO-, CH2=CH-CH2-COO-, CH2=CH-CH2-CH2-COO-, methacrylate group (CH2=C(CH3)-COO-), and the like.

[0044] In some embodiments of the present application, X1 and X2 are independently selected from One or more of; the position marked with * is the connection position. In this case, the compound represented by formula (I) is easier to synthesize. It is understood that when X1 is When X2 is Accordingly, when X2 is When X1 is In some embodiments, one of X1 and X2 is The other is In this case, the glass transition temperature of the compound represented by formula (I) is higher, and the electro-optic coefficient of the electro-optical active film formed using the compound is higher.

[0045] In the present application, R1 is selected from substituted or unsubstituted C1-C 10Alkylene. An alkylene group is a group formed by removing two hydrogen atoms bound to a carbon atom in an alkane, that is, an alkylene group is formed by removing one hydrogen atom bound to a carbon atom from the corresponding alkyl group. Substituted or unsubstituted alkylene groups may be linear or branched. Substituents in substituted alkylene groups may include, but are not limited to, halogen atoms, alkyl groups, alkoxy groups, and the like. In some embodiments, R1 is selected from substituted or unsubstituted C1-C8 alkylene groups, substituted or unsubstituted C1-C6 alkylene groups, or substituted or unsubstituted C2-C4 alkylene groups. An R1 with an appropriate number of carbon atoms can ensure that -R1-Z can be smoothly bonded to the π bridge in formula (I), and that X1 with the first crosslinkable group can be smoothly connected to -O-R1-Z, avoiding steric hindrance and side reactions during connection. In some embodiments, R1 can be an ethylene group (-CH2CH2-), a propylene group (-CH2CH2CH2-), or a butylene group (-CH2CH2CH2-).

[0046] The organic compound represented by formula (I) above has a D-π-A structure. The electron donor (represented by "D") has a lower electron affinity than the electron acceptor (represented by "A"). The portion with multiple conjugated double bonds connecting A and D can be referred to as a π bridge, or a "conjugated bridge." Electrons can be delocalized from the electron donor D to the electron acceptor A through the atomic orbitals in the π bridge. The electron donor D and the electron acceptor A will be described in more detail below.

[0047] In the present application, the electron donor D generally contains a tertiary ammonia nitrogen atom, which can utilize the lone electron pair of the tertiary ammonia nitrogen atom to have a strong electron-donating ability. In the embodiment of the present application, D can be an aromatic amine structure or a heteroaromatic amine structure containing a tertiary ammonia nitrogen atom.

[0048] In some embodiments of the present application, D comprises any one of the structures shown in formula (d-1) to formula (d-6) substituted or substituted:

[0049] in,*, The position marked is the connection position, the position marked with * is connected to -OCO-X2, each a is independently selected from an integer of 1-3, each b is independently selected from an integer of 0-3, and R2, R3, and R4 are independently selected from substituted or unsubstituted alkyl groups.

[0050] wherein each a can be independently 1, 2 or 3; b can be specifically 0, 1, 2 or 3. R2, R3, and R4 can be independently selected from substituted or unsubstituted C1-C 10Alkyl, further can be substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C1-C4 alkyl, etc. Wherein, the substituents in the substituted alkyl may include but are not limited to halogen atoms (such as fluorine, chlorine, bromine, iodine, etc.), univalent polar groups (such as cyano, nitro, hydroxyl, carboxyl, amino, ester group, acyl group, etc.), substituted or unsubstituted alkoxy, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloheteroalkyl, substituted or unsubstituted aryl (such as aryloxy, halogenated aryl), substituted or unsubstituted heteroaryl (such as heteroaryloxy, halogenated heteroaryl), etc. One or more. Wherein, the ring heteroatoms in the cycloheteroalkyl and heteroaryl groups can be independently selected from one or more of N, O, S, P, etc. The introduction of various substituents can enrich the variety of compounds, obtain compound products with slightly different properties, and better realize applications. In some embodiments, R2, R3, and R4 can be methyl or ethyl.

[0051] In addition, the substituents in any of the structures represented by formula (d-1) to formula (d-6) may include, but are not limited to, substituted or unsubstituted alkyl groups. 10 Alkyl, or substituted or unsubstituted C1-C6 alkyl, or substituted or unsubstituted C1-C4 alkyl. Exemplarily, the substituted or unsubstituted alkyl may include one or more of methyl, ethyl, n-propyl, methoxy, ethoxy, etc.

[0052] For the structure represented by the substituted formula (d-2), in some embodiments, it can be specifically or Each a may be the same or different.

[0053] In the embodiment of the present application, the electron acceptor A usually carries at least one electron-withdrawing group, which can be selected from at least one of a cyano group (-CN), a nitro group (-NO2), a fluorine atom (F), a sulfonic acid group (-SO3H), a trihalomethyl group (such as CF3), and a trifluoromethanesulfonyl group (-SO2CF3), but is not limited thereto.

[0054] For example, in some embodiments of the present application, A includes a structure represented by formula (A-1) or formula (A-2):

[0055] in, The positions marked with * are the attachment positions. X is independently selected from oxygen (O), sulfur (S), N (R8), or CH2. R5 and R6 are independently selected from substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Each occurrence of R7 is independently selected from an electron-withdrawing group. R8 is a hydrogen atom (H) or a substituted or unsubstituted alkyl group. The positions marked with * are the attachment positions.

[0056] Specifically, in formula (A-1) or formula (A-2), each R7 may be the same or different, and each occurrence of R7 is independently selected from one or more of cyano (-CN), nitro (-NO2), trihalomethyl (such as trifluoromethyl -CF3), fluorine atom (F), sulfonic acid (-SO3H), trifluoromethanesulfonyl (-SO2CF3), with cyano and / or nitro being more common. In some embodiments, each R7 is cyano.

[0057] When R5 and R6 are substituted or unsubstituted alkyl, they can be substituted or unsubstituted C1-C 20 Alkyl, or substituted or unsubstituted C1-C 12 Alkyl, or substituted or unsubstituted C1-C 10 alkyl, or substituted or unsubstituted C1-C6 alkyl, or substituted or unsubstituted C1-C4 alkyl, etc. The substituents in the substituted alkyl group can refer to the description above in this application. Among them, the substituents in the substituted alkyl group are more commonly halogen atoms, alkoxy groups, hydroxyl groups, and aryl groups. For example, the substituted alkyl group can be a trifluoromethyl group or a benzyl group (i.e., a methyl group substituted with a phenyl group).

[0058] When R5 and R6 are substituted or unsubstituted aryl groups, they can be monocyclic aryl groups or polycyclic aryl groups. The polycyclic aryl groups can be fused ring type or non-fused ring type (such as biphenyls). For non-fused ring type polycyclic aryl groups, the aromatic rings are directly connected or connected through at least one bridging group selected from oxygen atoms, sulfur atoms, alkylene groups, fluorenyl groups, etc. In the embodiment of the present application, the substituted or unsubstituted aryl groups can be substituted or unsubstituted C6-C 20 Aryl, or substituted or unsubstituted C6-C 15 Aryl, or substituted or unsubstituted C6-C 12 Aryl. For example, the substituted or unsubstituted aryl group may be a substituted or unsubstituted group of the following: phenyl, naphthyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, binaphthyl, fluorenyl, spirofluorenyl, etc.

[0059] When R5 and R6 are substituted or unsubstituted heteroaryl, they can be substituted or unsubstituted C3-C 20 Heteroaryl, or substituted or unsubstituted C4-C 15 Heteroaryl, or substituted or unsubstituted C5-C 10 Heteroaryl, etc. Wherein, the ring heteroatoms in the heteroaryl can be selected from one or more of N, O, S, P, etc. In some embodiments, the substituted or unsubstituted heteroaryl can be specifically a substituted or unsubstituted thienyl, such as 2-thienyl, 5-phenyl-2-thienyl and 5-(3-methoxymethylpropyl ether)-2-thienyl.

[0060] Wherein, the substituents in the substituted aryl and substituted heteroaryl may include one or more of a halogen atom, a monovalent polar group, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloheteroalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, etc. The substituents in the substituted aryl or substituted heteroaryl are more commonly halogen atoms, haloalkyl (such as fluoroalkyl), alkoxy, hydroxyalkyl, aryl, etc. Wherein, the number of carbon atoms in the substituted or unsubstituted cycloalkyl and substituted or unsubstituted cycloheteroalkyl may be 2-30, further 3-20, or 3-12, etc. The substituted or unsubstituted aryl may be a substituted or unsubstituted C6-C 30 Aryl, further may be substituted or unsubstituted C6-C 20 Aryl, substituted or unsubstituted C6-C 12 The substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C3-C 30 Heteroaryl, for example, is a substituted or unsubstituted C5-C 20 Heteroaryl, substituted or unsubstituted C6-C 12 Heteroaryl.

[0061] In some embodiments, one of R5 and R6 is methyl or trifluoromethyl, and the other is a substituted or unsubstituted C1-C 10 One of alkyl, phenyl, and thienyl; further, one of R5 and R6 may be trifluoromethyl (-CF3) and the other may be phenyl (-Ph).

[0062] When X is N(R8), R8 may be H, or a substituted or unsubstituted C1-C 10 In some embodiments, R8 is H.

[0063] In some embodiments, A is a structure represented by formula (A-1), and each R7 is a cyano group, one of R5 and R6 is a trifluoromethyl group (-CF3), and the other is a phenyl group (-Ph). In this case, A is specifically X is O, S, NH or CH2, preferably O or NH.

[0064] By regulating X1, X2, A, D, etc. with cross-linkable reaction groups in the above formula (I), the types of the above organic compounds can be enriched, and the glass transition temperature Tg of the organic compound can be regulated, thereby obtaining an electro-optical active film with good heat resistance and high electro-optical activity.

[0065] The following uses the compound represented by the following formula (IA) as an example to illustrate a method for preparing the above-mentioned organic compound in the examples of this application.

[0066] The preparation method of the compound represented by formula (IA) may comprise the following steps:

[0067] (1) Protecting the hydroxyl group on the hydroxyl compound K0 that can provide the electron donor D with a precursor that can provide the first hydroxyl protecting group Q1 to obtain compound K1;

[0068] (2) reacting compound K1 with compound a and compound b having the general formula OH-R1-ZH to obtain compound K2;

[0069] (3) protecting the hydroxyl group on compound K2 using a precursor that can provide a second hydroxyl protecting group Q2 to obtain compound K4;

[0070] (4) reacting compound K3 with diethyl cyanomethylphosphonate to obtain compound K4;

[0071] (5) Compound K4 is reduced with diisobutylaluminum hydride (DIBAL), and then hydrolyzed to obtain compound K5 with an aldehyde group;

[0072] (6) deprotecting the two second hydroxyl protecting groups on compound K5 to obtain compound K6;

[0073] (7) Compound K6 is subjected to an esterification reaction with compound d having the general formula X1-COOH to obtain compound K7;

[0074] (8) Compound K7 is subjected to an esterification reaction with a compound e having the general formula X2-COOH to obtain compound K8;

[0075] (9) reacting compound K8 with compound f that can provide electron acceptor A to obtain the compound represented by the above formula (IA);

[0076] Wherein, Q1 is the first hydroxyl protecting group, Q2 is the second hydroxyl protecting group, a is an integer of 0-3, n is an integer of 0-2, and the meanings of Z, R1, R5, R6, X1, and X2 are as described above in this application.

[0077] In the above preparation method, the hydroxyl protection reaction of steps (1) and (3) can be carried out according to the hydroxyl protection technology known in the art. The above Q1 and Q2 can be the same or different hydroxyl protecting groups, and the hydroxyl protecting groups can include tetrahydropyranyl, or organosilicon groups, etc. Among them, the organosilicon group can be, for example, one or more of tert-butyldimethylsilyl (-Si(CH3)2-C(CH3)3, abbreviated as TMDS), tert-butyldiphenylsilyl (-Si(Ph)2-C(CH3)3), triisopropylsilyl (-Si(CH(CH3)2)3), etc. The compound after the hydroxyl group is protected by the organosilicon group is generally a silyl ether. In some embodiments, the above first hydroxyl protecting groups Q1 and Q2 are both tert-butyldimethylsilyl. At this time, the precursor of the corresponding hydroxyl protecting group can be tert-butyldimethylchlorosilane. At this time, -O-Q1 or -O-Q2 can be called tert-butyldimethylsilyloxy. When the hydroxyl protecting group is Q1 or Q2 is tetrahydropyranyl, the corresponding precursor of the hydroxyl protecting group is 3,4-dihydro-2H-pyran.

[0078] Specifically, the reaction of step (1) is exemplified by taking the first hydroxyl protecting group Q1 as tert-butyldimethylsilyl, and the specific reaction formula is as follows:

[0079] The reaction carried out in step (2) can generate a conjugated polyene compound K2, and introduce a hydroxyl group to leave a reactive site for subsequent grafting of the group X1, so that X1 is connected to the final product. Wherein, -ZH (Z is S, O or NH) is an active group that can open the epoxy group in compound a, specifically a thiol (-SH), a hydroxyl (-OH) or a primary amino group (-NH2). In order to improve the yield of the reaction in step (2), Z is preferably S or NH, and R1 is preferably a straight-chain alkylene group, such as -(CH2) 2～4 .

[0080] Taking compound b as 2-mercaptoethanol as an example, the reaction of step (2) is shown below:

[0081] The reaction in step (4) can achieve the conversion of the cyclic ketone group on the cycloalkenone K3 to the cyano group, thereby increasing the number of carbon atoms so as to subsequently add a carbon-carbon double bond to the π bridge. The reaction equation involved in step (4) is shown below:

[0082] In step (5), DIBAL can reduce the nitrile K4 to an amine, which is then hydrolyzed to obtain the aforementioned aldehyde K5.

[0083] In step (6), the hydroxyl group protected by the hydroxyl protecting groups Q1 and Q2 is deprotected to restore -OH, thereby obtaining a diol compound K6 with two -OH groups. The specific reaction parameters for the deprotection can be selected according to the specific Q1 and Q2. In some embodiments of the present application, when Q1 and Q2 are both tert-butyldimethylsilyl groups, they can be removed in the presence of hydrochloric acid.

[0084] In step (7), the esterification reaction between the diol compound K6 and the carboxylic acid compound can be carried out in the presence of a catalyst (also known as an "activator") and a condensing agent (also known as a "dehydrating agent"). In step (7), the esterification reaction mainly occurs between one hydroxyl group and the carboxyl group in compound K6, and the esterification reaction between the remaining hydroxyl group and the carboxyl group is carried out in step (8). In some embodiments of the present application, when carrying out the esterification reaction in step (7), the condensing agent used can be EDCI (1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride), and the catalyst used can be 4-dimethylaminopyridine (abbreviated as DMAP).

[0085] Similar to step (7), the esterification reaction in step (8) can also be carried out in the presence of a catalyst and a condensing agent. In some embodiments, in the reaction of step (8), EDCI can be used as a condensing agent and DMAP as a catalyst.

[0086] In some embodiments, the compound d used in step (7) can be

[0087] In some embodiments, the compound e used in step (8) can be selected from any one of the following substances, but is not limited thereto:

[0088] The reaction in step (9) is primarily a reaction in which the carbon anion formed by the methyl group in compound f under certain conditions attacks the aldehyde group in compound K8, causing a condensation reaction, removing water, and forming a carbon-carbon double bond. The reaction in step (9) allows the electron acceptor A to be connected to the π bridge.

[0089] The reaction equation in step (9) is as follows:

[0090] The preparation of self-crosslinking organic electro-optical materials is generally difficult, but the preparation method of the compound represented by formula (IA) described above provides a feasible route for preparing organic compounds having groups that can undergo crosslinking reactions with each other, and the yield of each step is high. This preparation method is applicable to the preparation of a variety of organic compounds with different structures. Among them, the hydroxyl compound K0 that can provide the electron donor D in step (1) can be replaced to obtain an organic compound with a different D; the compound f in step (9) can be replaced to obtain an organic compound with a different A; the carboxyl compounds d and e in the above steps (7) and (8) can be replaced to obtain an organic compound with different X1 and X2.

[0091] It should be noted that in the above preparation method, the two hydroxyl protecting groups Q1 and Q2 are removed simultaneously in step (6), and then the esterification reactions of steps (7) and (8) are carried out in sequence. It is understood that in other embodiments of the present application, one of the hydroxyl groups may be deprotected first, and the deprotected hydroxyl group may be subjected to an esterification reaction, and then the deprotection and esterification reactions of the other hydroxyl group may be carried out.

[0092] The present invention also provides a composition comprising the organic compound and a solvent. The composition can be used to prepare a film containing a crosslinked product of the organic compound, in particular, to prepare an electro-optically active film.

[0093] The solvent is capable of dissolving the organic compound. Exemplary solvents may include, but are not limited to, one or more of chloroform (ie, chloroform), dibromomethane, and dichloromethane.

[0094] In some embodiments of the present application, the composition does not contain an external crosslinking agent and may contain only the aforementioned organic compound and a solvent. The organic compound serves as both the effective active component (chromophore) and the crosslinking agent. The electro-optically active film produced using this composition has a high content of the effective active component and exhibits high electro-optical performance.

[0095] The present invention also provides a film comprising a cross-linked product of the aforementioned composition or a cross-linked product of the aforementioned organic compound. The film is obtained by cross-linking the composition containing the aforementioned organic compound.

[0096] In the embodiment of the present application, the film may be an electro-optically active film, which is generally polarized and oriented by an electric field before cross-linking. The electro-optically active film is particularly suitable for manufacturing components of optical communication systems, such as electro-optic modulators.

[0097] In the embodiment of the present application, the glass transition temperature (Tg) of the above-mentioned film is greater than or equal to 150°C, and specifically may be greater than or equal to 160°C, greater than or equal to 180°C, greater than or equal to 200°C, etc. The glass transition temperature of the film provided in the embodiment of the present application is relatively high, especially in the field of electro-optical active films. The high Tg film provided in the embodiment of the present application is particularly helpful for the stable operation of various components of optical communication systems using the film. Among them, Tg can be measured by differential scanning calorimetry (DSC) or thermogravimetric analysis (TGA).

[0098] In the embodiment of the present application, the electro-optic coefficient (r 33 ) is greater than or equal to 190pm / V. Among them, the electro-optic coefficient of the film (r 33 ) is the maximum electro-optic coefficient r measured by the simple reflection method (also known as the Teng-Man method, see CCTeng, HTMan, Simple refection technique for measuring the electro-optic coefficient of poled polymers, Applied Physics Letters, 1990, 56(18), 1734-1736.) 33 Therefore, it can be said that the maximum r of the electro-optical active film provided by the embodiment of the present application is 33 is greater than or equal to 190 pm / V. In some embodiments, the maximum r 33 The electro-optical active film provided in the embodiment of the present application has a r greater than or equal to 195 pm / V, greater than or equal to 200 pm / V, greater than or equal to 230 pm / V, or even greater than or equal to 260 pm / V. 33 Therefore, the electro-optical active film provided by the embodiment of the present application can have both a higher Tg and a higher electro-optical coefficient r 33 , the overall performance is good.

[0099] In the embodiment of the present application, the average polarization efficiency of the film is greater than or equal to 1.5nm 2 / V 2 In some embodiments, the polarization efficiency of the film is greater than or equal to 1.8 nm 2 / V 2 Among them, through multiple polarization field data and corresponding r 33 The average polarization efficiency of the film is calculated by linear least squares regression.33 The slope of the linear fitting curve of the polarization field strength is 1.5-2.5nm. 2 / V 2 , for example, 1.5, 1.6, 1.8, 2.0, 2.2, 2.3 or 2.4 nm 2 / V 2 wait.

[0100] The present invention also provides a method for preparing an electro-optically active thin film, which comprises the following steps:

[0101] (1) coating a solution containing an organic compound according to an embodiment of the present application (such as the above-mentioned composition according to an embodiment of the present application) on a substrate and drying the solution to form a film layer;

[0102] (2) applying an electric field to the film layer and heating it at a first temperature to polarize the organic compound in the film layer;

[0103] (3) The polarized film layer is further heated to a second temperature to allow the organic compound in the film layer to self-crosslink, and then the temperature is lowered to obtain an electro-optically active thin film.

[0104] When an electric field is applied to the film obtained in step (1), at a first temperature, the molecules of the organic compound in the film are reoriented so that their dipole moments are aligned with the electric field; then, heating is continued in the presence of the electric field to cause a cross-linking reaction in the film, thereby stabilizing the already polarized molecules; thereafter, the temperature is lowered while the electric field is still present, so that the polarized molecules can be maintained, thereby obtaining an electro-optically active film. The glass transition temperature of the electro-optically active film is generally higher than that of the film obtained in step (1), which facilitates the long-term stable operation of the electro-optical device made using the electro-optically active film at high temperatures, thereby preventing the electro-optically active film from losing its electro-optical activity due to its inability to withstand high temperatures.

[0105] The applied electric field may specifically be a direct current electric field. The electric field may be applied by connecting the film layer between a positive electrode and a negative electrode. Furthermore, the second temperature is higher than the first temperature, and the second temperature may be referred to as the "crosslinking temperature." The first temperature is generally close to the glass transition temperature Tg of the organic compound described in the embodiments of the present application. Generally, the second temperature may be 20-70°C higher than the first temperature.

[0106] The present application also provides the use of the above-mentioned organic compounds, the above-mentioned compositions, the above-mentioned films, and the electro-optically active films prepared by the above-mentioned methods for preparing electro-optically active films in the embodiments of the present application in components of optical communication systems, solar cells, organic electroluminescent devices, and organic photoluminescent devices.

[0107] In applications such as solar cells, organic electroluminescent devices, and organic photoluminescent devices, the electro-optical activity of the organic compounds described above is not required. These organic compounds or films are typically used as hole transport layers in these solar cells, organic electroluminescent devices, and organic photoluminescent devices. Therefore, the films do not need to exhibit electro-optical activity, and therefore, when preparing the films using the aforementioned preparation methods, no electric field needs to be applied. Of course, even if the films exhibit electro-optical activity, this does not affect their hole transport function. Specifically, when the aforementioned applications are in organic electroluminescent devices or organic photoluminescent devices, the organic compounds or films described above can improve the luminous efficiency of the light-emitting devices. When used in solar cells, such as dye-sensitized solar cells, the solar cells can improve their utilization of sunlight and their photoelectric conversion efficiency. If these solar cells are installed in electric vehicles, they can be charged with solar energy. If these solar cells are made into solar cell glass, they can be used to power indoor spaces using solar energy.

[0108] In more cases, the organic compounds, compositions, films, etc. provided herein can be used in optical communication systems, specifically for manufacturing components of optical communication systems. In embodiments of the present application, the components of the optical communication systems include one or more of electro-optical devices, optical switches, straight waveguides, curved waveguides, single-mode optical splitters, routers, filters, optical interconnects, and resonators. The electro-optical devices include one or more of electro-optical modulators, terahertz detectors, electro-optical frequency shifters, and frequency comb sources. Optical switches can also be referred to as "optical modulators."

[0109] The present application also provides a component of an optical communication system, wherein the component includes the electro-optically active film described above in the embodiment of the present application. The component of the optical communication system may be as described above in the present application.

[0110] The present invention also provides an electro-optical device comprising the electro-optically active film of the present invention, wherein the electro-optically active film can be used as an electro-optical functional layer of the electro-optical device.

[0111] In an embodiment of the present application, the electro-optical device includes one or more of an electro-optic modulator, a coupler, a terahertz detector, an electro-optic frequency shifter, and a frequency comb source. The electro-optical modulator may include, but is not limited to, one or more of a Mach-Zehnder modulator (MZM), a phase modulator, a silicon-organic hybrid modulator, a plasma-organic hybrid modulator, and the like.

[0112] Referring to Figure 1, the present application provides a schematic structural diagram of an electro-optic modulator. The electro-optic modulator 100 includes a first electrode 20, a second electrode 50, and a waveguide layer 30 and an electro-optical functional layer 40 sandwiched therebetween, wherein the waveguide layer 30 is adjacent to the first electrode, and the electro-optical functional layer 40 is adjacent to the second electrode 50. The electro-optical functional layer 40 includes the electro-optically active film described above in the embodiment of the present application. In the embodiment of the present application, the electro-optic modulator 100 also includes a substrate 10, wherein the first electrode 20, the waveguide layer 30, the electro-optical functional layer 40, and the second electrode 50 are sequentially stacked on a side surface of the substrate 10.

[0113] The substrate 10 may be a Si wafer having a silicon oxide layer on its surface. The first electrode 20 may be aluminum or other metal materials. The waveguide layer 30 may include an input waveguide and an output waveguide, both of which have a Y-shaped structure. The input waveguide and the output waveguide are coupled via two modulation arms to form a Mach-Zehnder (MZI) waveguide structure, wherein each output end of the input waveguide is coupled to the input end of the output waveguide via a modulation arm. The waveguide layer 30 may be made of Si. The second electrode 50 may be a traveling wave electrode made of Au (gold) and may include an electrode pair. The orthographic projection of the second electrode 50 on the waveguide layer 30 may fall on the two modulation arms of the band layer 3. In addition, a first dielectric layer 203 (e.g., SiO2) may be provided between the first electrode 20 and the waveguide layer 30, and a second dielectric layer 405 (e.g., SiO2) may be provided between the electro-optical functional layer 40 and the second electrode 50 to provide isolation and protection.

[0114] During operation of the electro-optic modulator, the second electrode 50 and the first electrode 20 can be electrically connected to apply a modulation voltage across the electro-optical functional layer 40, achieving phase modulation through the electro-optical effect of the electro-optic material. Light generated by a laser light source can be input from the input end of the waveguide layer 30, evenly split by the Y-shaped structure, and then enter the two modulation arms of the waveguide layer 30. When the voltage applied across the electro-optical functional layer 40 changes, the refractive index of the electro-optical functional layer 40 changes, and the characteristics of the light wave change, thereby modulating the phase, amplitude, intensity, and polarization state of the optical signals in the upper and lower modulation arms. After modulation, the light from the upper and lower modulation arms is combined by the Y-shaped structure and output from the output end of the waveguide layer 30. The optical power of the output light varies with the modulation signal, achieving electro-optical modulation.

[0115] An embodiment of the present application further provides an optical communication system, comprising at least one component of the aforementioned optical communication system.

[0116] An embodiment of the present application also provides a phased array lidar system, which includes the electro-optical active film described above in the embodiment of the present application.

[0117] The embodiments of the present application are further described below with reference to a number of embodiments.

[0118] Example 1

[0119] An organic compound SLD1, whose structural formula is shown below:

[0120] The preparation of the organic compound SLD-1 comprises:

[0121] 1) Compound K1 1 Synthesis

[0122] The synthetic route is shown below:

[0123] The hydroxy compound K0 1 and tert-butyldimethylsilyl chloride as the reaction raw materials, and the method described in reference (Chem.Mater.2020,32,1408-1421) was used to synthesize compound K1 1 .

[0124] 2) Compound K2 1 Synthesis

[0125] The synthetic route is shown below:

[0126] Sodium metal (0.46 g, 20.00 mmol) was added to 30 mL of ethanol to obtain a solution containing sodium ethoxide (C2H5ONa). The solution was transferred to a two-necked flask under nitrogen atmosphere. After the sodium was completely dissolved, 2-mercaptoethanol (1.56 g, 1.47 mL, 20.00 mmol) was added to the above solution. After reacting at room temperature for 15 minutes, compound a was added. 1 (isophorone oxide, 3.08 g, 20 mmol), stirred at room temperature for 1 h, and then added the above compound K2 1 (5.87 g, 20.0 mmol), and reacted at 65 ° C for 18 hours to obtain a reaction solution. The reaction solution was concentrated using a rotary evaporator, and the concentrated reaction solution was purified by column chromatography using ethyl acetate and hexane (volume ratio of 1:10 to 1:6) as eluents to obtain a red oily compound K2 1 , with a yield of 78.9% (7.81 g, 15.95 mmol).

[0127] Compound K2 1 The mass spectrometry characterization results are: MS (MALDI) (M + ,C 27 H 43 NO3SSi): Calculated value: 489.79; Measured value: 489.81. Compound K2 1The H NMR spectrum results are 1 H NMR (300MHz, CDCl3) δ (ppm): 7.92 (d, J=16.1Hz, 1H), 7.46 (d, J=8.6Hz, 2H), 7.04 (d, J= 16.1Hz,1H),6.68(d,J=8.7Hz,2H),4.02-3.80(m,4H),3.60-3.48(m,4H),3.04(s,3H), 2.59(s,2H),2.45(s,2H),1.07(s,6H),0.87(s,9H),0.01(s,6H). Compound K2 1 The results of the carbon NMR spectrum are: 13 C NMR (126MHz, CDCl3) δ (ppm): 197.05, 160.19, 149.93, 138.56, 129.33, 127.09, 126.69, 123.69, 122 .42,111.62,60.29,60.13,54.31,51.45,40.94,38.99,38.42,31.96,28.17,25.70,17.97,-5.45.

[0128] 3) Compound K3 1 Synthesis

[0129] The synthetic route is shown below:

[0130] Under nitrogen atmosphere, tert-butyldimethylsilyl chloride (3.68 g, 24 mmol) was slowly added to the above compound K3. 1 A solution of 1,3-dimethyl-1-oxo ... 1 , the yield was 93.1% (5.49 g, 9.31 mmol).

[0131] Compound K3 1 The mass spectrometry characterization results are: MS (MALDI) (M + ,C 33 H 57 NO3SSi2): Calculated value: 604.05; Measured value: 603.95. Compound K31 The results of the H NMR spectrum are: 1 H NMR (300MHz, CDCl3) δ (ppm): 7.89 (d, J = 16.2Hz, 1H), 7.44 (d, J = 8.6Hz, 2H), 6.98 (d, J = 16.2Hz, 1H), 6.66 (d, J = 8.7Hz, 2H), 3.77 (t, J = 5.7Hz, 2H), 3.68 (t,J=6.9Hz,2H),3.51(t,J=5.6Hz,2H),3.03(s,3H)2.96-2.78(m,2H),2.5 9(s,2H),2.39(s,2H),1.06(s,6H),0.9-0.77(m,18H),0.08-0.02(m,12H). Compound K3 1 The results of the carbon NMR spectrum are: 13 C NMR (126MHz, CDCl3) δ (ppm): 195.67, 157.70, 150.03, 137.20, 129.20, 128.01, 123.97, 123.37, 111.8 4,62.79,60.12,54.46,51.87,41.18,39.13,36.53,32.14,30.62,28.26,25.77,18.14,-5.45,-5.63.

[0132] 4) Compound K4 1 Synthesis

[0133] The synthetic route is shown below:

[0134] Under nitrogen atmosphere, diethyl (cyanomethyl)phosphonate (Compound C, 1.81 mL, 1.99 g, 11.2 mmol) was slowly added to a two-necked flask containing 12 mL of dry THF containing NaH (0.27 g, 11.2 mol) to obtain a mixture. 1 A solution of 1.69 g, 2.80 mmol) in THF (5 mL) was added to the above mixture. After the solution was clarified, it was refluxed at 68°C for 24 hours to obtain a reaction solution. The THF in the reaction solution was removed by rotary evaporation, and the residue was purified by silica gel column chromatography using ethyl acetate / hexane (volume ratio of 1:15 to 1:10) as the eluent to obtain compound K4 as a red solid. 1 , with a yield of 73.1% (1.28 g, 2.04 mmol).

[0135] Compound K4 1 The mass spectrometry characterization results are: MS (MALDI) (M+ ,C 35 H 58 N2O2SSi2): Calculated value: 627.09; Measured value: 627.13. Compound K4 1 The results of the H NMR spectrum are: 1 H NMR (300 MHz, CDCl3) δ (ppm): 7.84 (d, J = 16.1 Hz, 1H), 7.38 (d, J = 8.4 Hz, 2H), 6.83 (d, J = 16.1 Hz, 1H), 6.64 (d, J = 8.4 Hz, 2H), 6.23 (s, 1H), 3.82-3.61 (m, 4H), 3.48-3.46 (m, 2H), 2.99 (m, 3H), 2.67-2.65 (m, 2H), 2.53 (s, 2H), 2.43 (s, 2H), 0.99 (s, 6H), 0.87 (m, 18H), 0.05-0.02 (m, 12H). Compound K4 1 The results of the carbon NMR spectrum are: 13 C NMR (126MHz, CDCl3) δ (ppm): 158.13, 149.59, 148.68, 134.79, 128.63, 125.94, 124.50, 123.94, 118.84, 111.6 6,94.47,62.11,60.34,54.37,38.86,30.57,29.88,29.53,27.84,25.76,22.51,17.99,14.01,-5.45,-5.61.

[0136] 5) Compound K5 1 Synthesis

[0137] The synthetic route is shown below:

[0138] The above compound K4 1 The solution obtained by dissolving 1.25 g, 2.00 mmol) in 20.0 mL of freshly dried toluene was cooled to -78 ° C under a nitrogen atmosphere, and a 1.5 M hexane solution of diisobutylaluminum hydride (DIBAL) (DIBAL is 4.00 mmol) was slowly added. After stirring and reacting at -78 ° C for 2 h, wet silica gel (1.0 g) containing 10.0 mL of water was added thereto, and the reaction was carried out at 0 ° C for 2 h to obtain a reaction mass. The reaction mass was poured into water, extracted with ethyl acetate, and the obtained organic phase was concentrated using a rotary evaporator. The concentrated residue was purified by silica gel column chromatography and eluted with ethyl acetate / hexane (volume ratio of 1:8 to 1:5) to obtain compound K5 as a red solid. 1, with a yield of 70.1% (0.88 g, 1.40 mmol).

[0139] Compound K5 1 The mass spectrometry characterization results are: MS (MALDI) (M + ,C 35 H 59 NO3SSi2): Calculated value: 630.09; Measured value: 630.15. Compound K5 1 The results of the H NMR spectrum are: 1 H NMR (300MHz, CDCl3) δ (ppm): 10.12 (d, J = 6.4Hz, 1H), 7.94 (d, J = 16.1Hz, 1H), 7 .40(d,J=6.8Hz,2H),6.98(d,J=6.6Hz,1H),6.85(d,J=16.1Hz,1H),6.65(d,J= 6.8Hz,2H),3.76-3.74(m,4H),3.49-3.48(m,2H),3.01(s,3H),2.70-2.67(m, 2H),2.47(s,2H),2.11(s,2H),1.01(s,6H),0.86-0.82(m,18H),0.02(s,12H). Compound K5 1 The results of the carbon NMR spectrum are: 13 C NMR (126MHz, CDCl3) δ (ppm): 190.77, 156.09, 149.77, 149.50, 134.66, 128.57, 127.97, 126.58, 124.35, 11 1.44,62.08,60.25,54.48,41.36,39.62,38.82,37.39,30.42,29.66,28.04,25.51,17.94,-5.49,-5.63.

[0140] 6) Compound K6 1 Synthesis

[0141] The synthetic route is shown below:

[0142] 5.60 mmol of HCl was added to the above compound K5 1The product was dissolved in 10 mL of acetone (0.88 g, 1.40 mmol) and stirred at room temperature for 3 h. The resulting reaction solution was neutralized with sodium bicarbonate and the organic solvent was concentrated using a rotary evaporator. The residue was poured into 20 mL of water and extracted with 100 mL of dichloromethane, then concentrated using a rotary evaporator, dried over Na2SO4, and concentrated to give a crude product. The crude product was purified by flash chromatography on silica gel using a gradient eluent of dichloromethane / ethyl acetate (volume ratio of 10:1 to 5:1) to give Compound K6 as a red solid. 1 , with a yield of 93.1% (0.52 g, 1.30 mmol).

[0143] Compound K6 1 The mass spectrometry characterization results are: MS (MALDI) (M + ,C 23 H 31 NO3S): Calculated value: 401.56; Measured value: 401.78. Compound K6 1 The results of the H NMR spectrum are: 1 H NMR (300MHz, CDCl3) δ (ppm): 10.08 (d, J = 8.1Hz, 1H), 7.94 (d, J = 16.2Hz, 1H), 7.42 (d, J = 8.8Hz, 2H), 6.97 (d, J = 8.1Hz, 1H), 6.86 (d, J = 16.2Hz, 1H), 6.72 ( d,J=8.8Hz,2H),3.84-3.81(m,2H),3.62(m,2H),3.52(m,2H),3.02(s,3H), 2.76-2.74(m,2H),2.71(s,2H)2.49(s,2H),2.36-2.32(m,2H),1.02(s,6H). Compound K6 1 The results of the carbon NMR spectrum are: 13 C NMR (126MHz, CDCl3) δ (ppm): 191.79 157.37, 150.83, 150.17, 135.29, 128.85 127.50,126.49,124.92,124.52,112.12,61.06,59.86,54.54,41.95,39.78,38.74,38.02,29.97,28.17.

[0144] 7) Compound K7 1 Synthesis

[0145] The synthetic route is shown below:

[0146] Under nitrogen atmosphere, the carboxylic acid compound d 1 (3,5-bis(acryloyloxy)benzoic acid, 3.24 g, 12.36 mmol), catalyst DMAP (0.15 g, 1.24 mmol), condensation agent EDCI (2.37 g, 12.36 mmol) and appropriate amount of dichloromethane were placed in a clean and dry test tube and stirred at 0°C for 45 min to obtain a clear solution, and then the above compound K6 was added 1 (4.00 g, 10.30 mmol), continued stirring at 0°C for 2 h, then transferred to an oil bath and heated under reflux overnight to obtain a reaction mass. The reaction mass was extracted with dichloromethane, and the resulting crude organic layer was concentrated under vacuum and purified by column chromatography using a mixed solvent of petroleum ether and ethyl acetate (volume ratio of 8:1 to 2:1) as eluent to obtain a dark red compound K7. 1 , with a yield of 92.3% (5.09 g, 7.88 mmol).

[0147] Compound K7 1 The mass spectrometry characterization results are: MS (MALDI) (M+, C 36 H 39 NO8S): Calculated value: 645.76; Found: 645.75. Compound K7 1 The results of the H NMR spectrum are: 1 H NMR (600MHz, CDCl3) δ (ppm): 10.13 (d, J = 8.0 Hz, 1H, CHO), 7.95-7.91 (m, 1H, CH), 7.70-7.63 (m, 2H, CH), 7.27 (dd, J = 10 .4,5.5Hz,3H,CH),6.97(t,J=7.6Hz,1H,ArH),6.82(d,J=16.2Hz,1H,CH),6.63-6.56(m,4H,ArH),6.33-6.27(m,2H,A rH),6.07-6.03(m,2H,CH),4.39-4.31(m,2H,OCH2),3.85-3.74(m,2H,NCH2),3.53-3.47(m,2H,OCH2),3.00(d,J=4.2 Hz,3H,CH3),2.93(dt,J=12.5,6.2Hz,2H,CH2),2.74(d,J=12.0Hz,2H,CH2),2.53-2.41(m,2H,CH2),1.03(s,6H,CH3). Compound K7 1 The results of the carbon NMR spectrum are: 13C NMR (151MHz, CDCl3) δ (ppm): 191.69, 164.56, 164.01, 156.25, 151.60, 150.92, 150.30, 135.50, 133.66, 132.22, 128. 91,127.43,126.94,125.09,124.62,120.36,112.28,63.95,60.14,54.77,41.73,39.98,38.97,33.27,30.20,28.41.

[0148] 8) Compound K8 1 Synthesis

[0149] The synthetic route is shown below:

[0150] Under nitrogen atmosphere, the carboxylic acid compound e 1 (Specifically 3-(anthracen-9-yl)propionic acid, 9.46 mmol), DMAP (0.11 g, 0.95 mmol) and EDCI (1.81 g, 9.46 mmol) were placed in a clean, dry test tube and stirred at 0°C for 45 minutes until the solution became clear, and then compound K7 was added. 1 (5.09 g, 7.88 mmol), continued stirring at 0°C for 2 hours, transferred to an oil bath and heated under reflux overnight to obtain a reaction mass. The reaction mass was extracted with dichloromethane, and the resulting crude organic layer was concentrated under vacuum and purified by column chromatography using a mixed solvent of petroleum ether and ethyl acetate (volume ratio of 8:1 to 2:1) as eluent to obtain a light red oily compound K8. 1 The yield was 76.8% (5.31 g, 6.05 mmol).

[0151] Compound K8 1 The mass spectrometry characterization results are: MS (MALDI) (M+, C 53 H 51 NO9S): Calculated value: 878.05; Found: 878.06. Compound K8 1 The results of the H NMR spectrum are: 1H NMR (600MHz, CDCl3) δ (ppm): 10.19 (dd, J=7.9, 3.3Hz, 1H, CHO), 8.44-8.34 (m, 2H, ArH), 8.30-8.23 (m, 3H, CH), 8.03-7.98 (m,4H,ArH),7.67-7.64(m,2H,ArH),7.49-7.43(m,3H,ArH),7.41-7.39(m,2H,ArH),6.67-6.62(m,2H,CH),6.62-6.52(m, 3H,ArH),6.36-6.30(m,2H,CH),6.09-6.05(m,2H,CH),4.39(t,J=6.3Hz,2H,OCH2),4.20(dd,J=11.1,4.5Hz,2H,OCH2),4. 14(ddd,J=22.6,14.6,7.7Hz,2H,NCH2),3.93(dt,J=11.6,4.2Hz,2H,SCH2),3.59(t,J=6.0Hz,2H,CH2),2.92(d,J=2.5Hz, 3H, CH3), 2.82 (dd, J = 15.0, 8.4 Hz, 2H, CH2), 2.57-2.46 (m, 2H, CH2), 1.29 (t, J = 7.1 Hz, 2H, CH2), 1.10-1.05 (m, 6H, CH3). Compound K8 1 The results of the carbon NMR spectrum are: 13 C NMR (151MHz, CDCl3) δ (ppm): 191.65, 172.84, 164.84, 163.89, 156.26, 151.15, 150.99, 149.40 ,135.27,133.59,132.43,132.00,131.68,129.58,129.39,128.99,127.38,127.28,127.20,1 27.03,126.85,126.37,126.07,125.33,125.07,124.03,123.82,120.40,112.07,62.75,60.51,50.65,41.80,40.00,38.68,35.35,33.39,30.21,30.08,28.39,23.41,23.25,21.17,14.32.

[0152] 9) Synthesis of compound SLD1

[0153] The synthetic route is shown below:

[0154] Under nitrogen atmosphere, the above compound K8 was added into a two-necked flask. 1 (0.53 g, 6.05 mmol), compound f 1 The product was prepared by distilling water (specifically, 2-(3-cyano-4-methyl-5-phenyl-5-(trifluoromethyl)furan-2(5H))-ethylidene)malononitrile, 6.65 mmol), dissolving it in 5-6 mL of ethanol and then stirring and refluxing at 65°C for 6 hours. After the reaction was complete, the resulting solution was concentrated to obtain a crude product. This crude product was purified twice by column chromatography using petroleum ether and ethyl acetate (1:4 to 1:1) as eluents to obtain a green solid, the organic chromophore SLD1, with a yield of 67.8% (0.48 g, 4.10 mmol).

[0155] The mass spectrometry characterization results of SLD1 are as follows: HRMS (ESI) ([M+H]+, C 69 H 57 F3N4O9S): calculated value: 1175.3877; measured value: 1175.3876. The H NMR spectrum results of SLD1 are: 1H NMR (600MHz, CDCl3) δ (ppm): 8.40-8.29 (m, 2H, ArH), 8.17 (t, J = 7.2Hz, 3H, ArH), 7.99 (d d,J=13.1,5.6Hz,4H,CH),7.47-7.46(m,5H,ArH),7.43(dd,J=8.8,3.1Hz,2H,ArH),7.4 0(d,J=8.9Hz,3H,ArH),7.37-7.28(m,2H,ArH),7.11(dt,J=17.8,8.9Hz,1H,CH),7.01- 6.88(m,2H,ArH),6.84(t,J=2.2Hz,1H,ArH),6.59-6.55(m,3H,CH),6.56-6.45(m,2H,CH ),6.31-6.24(m,1H,ArH),6.01(dd,J=10.5,1.0Hz,1H,CH),4.36(t,J=5.7Hz,2H,OCH2) ,4.16(dd,J=12.2,5.6Hz,2H,OCH2),4.15-4.10(m,2H,NCH2),3.89(t,J=7.5Hz,2H,SCH 2), 3.62 (t, J = 5.7 Hz, 2H, CH2), 2.92 (d, J = 4.0 Hz, 3H, CH3), 2.78 (t, J = 6.6 Hz, 2H, CH2), 2.75-2.73 (m, 2H, CH2), 2.56-2.48 (m, 2H, CH2), 1.01-0.97 (m, 3H, CH3), 0.90 (s, 3H, CH3). The results of the carbon NMR spectrum of SLD1 are: 13 C NMR (151MHz, CDCl3) δ (ppm): 175.69, 173.33, 171.43, 165.53, 164.29, 156.95, 151.43, 150.54, 147. 34,138.11,133.31,132.12,131.89,131.68,131.48,129.82,129.51,129.21,128.40,127.66,126. 85,126.60,126.22,125.12,123.87,117.38,115.05,114.36,114.09,112.46,110.79,63.30,62.36,60.59,58.38,50.64,41.87,41.27,38.46,35.39,33.98,30.55,28.66,27.98,23.36,21.20,14.32.

[0156] Among them, the compound SLD1 provided in Example 1 of the present application can undergo a self-crosslinking reaction at a certain temperature, specifically a Diels-Alder cycloaddition crosslinking reaction between the anthracene group and the acrylate group. Specific examples are as follows:

[0157] Example 2

[0158] An organic compound SLD2, whose structural formula is shown below:

[0159] The main difference between the synthesis method of the organic compound SLD2 and the above SLD1 is that the carboxylic acid compound e used in step (8) is 1 Replaced with the following carboxylic acid compound e 2 (Specifically 3,5-bis(anthracen-9-ylmethoxy)benzoic acid, 9.46 mmol).

[0160] The synthetic route involved in step (8) is shown below:

[0161] In step (8), the obtained compound K8 2 The yield was 73.8% (6.79 g, 5.85 mmol). 2 The reaction of step (9) was carried out to obtain the green solid chromophore SLD2 with a yield of 63.8% (0.56 g, 3.85 mmol).

[0162] Compound K8 2 The mass spectrometry characterization results are: MS (MALDI) (M+, C 73 H 63 NO 11 S): Calculated value: 1162.4200; Found: 1162.4211. Compound K8 2 The results of the H NMR spectrum are: 1H NMR (600MHz, CDCl3) δ (ppm): 10.19 (dd, J = 7.9, 3.3Hz, 1H, CHO), 8.64-8.54 (m, 2H,ArH),8.50-8.43(m,3H,CH),8.33-8.26(m,9H,ArH),8.23-7.98(m,4H,ArH) ,7.87-7.74(m,2H,ArH),7.69-7.63(m,12H,ArH),7.61-7.69(m,2H,ArH),6.8 7-6.82(m,2H,CH),6.82-6.772(m,3H,ArH),6.56-6.50(m,2H,CH),6.39-6.25( m,2H,CH),4.41(t,J=6.3Hz,2H,OCH2),4.33(dd,J=11.1,4.5Hz,2H,OCH2),4. 24(ddd,J=22.6,14.6,7.7Hz,2H,NCH2),3.97(dt,J=11.6,4.2Hz,2H,SCH2),3. 79(t,J=6.0Hz,2H,CH2),2.93(d,J=2.5Hz,3H,CH3),2.92(dd,J=15.0,8.4Hz, 2H, CH2), 2.77-2.56 (m, 2H, CH2), 1.39 (t, J = 7.1Hz, 2H, CH2), 1.10 (s, 6H, CH3). Compound K8 2 The results of the carbon NMR spectrum are: 13 C NMR (151MHz, CDCl3) δ (ppm): 191.65, 172.33, 164.47, 163.99, 156.47, 151.35, 150.88, 149.5 6,135.57,133.71,132.56,132.55,131.77,129.68,129.51,129.49,129.13,128.89,128.66, 128.33,127.43,127.34,127.35,127.23,126.75,126.35,126.27,125.34,125.37,124.45,123.78,122.44,113.47,62.85,60.81,52.77,40.99,40.12,39.77,37.35,34.29,31.33,30.28, 29.39,24.43,24.35,22.27,14.12.

[0163] The mass spectrometry characterization results of SLD2 are as follows: HRMS (ESI) ([M+H]+, C 89 H 69F3N4O 11 S): calculated value: 1459.4714; measured value: 1459.4721. The results of the nuclear magnetic resonance hydrogen spectrum of SLD2 are: 1H NMR (500MHz, CDCl3) δ (ppm): 8.43 (d, J = 7.1Hz, 2H, ArH), 8.14 (d, J = 8.7Hz, 4H, ArH), 7.95 (d, J = 8.2Hz, 4H, ArH), 7.55 (d, J = 1.7Hz, 2H, ArH), 7.47 ( dd,J=12.7,5.6Hz,10H,CH),7.43-7.38(m,9H,CH,ArH),7.28(d,J=12.2Hz,1H,ArH),7.15(d,J=17.4Hz,1H,CH),6.93(s,1H,CH),6.65(d,J=8.8Hz ,2H,ArH),6.52(d,J=17.3Hz,2H,CH),6.39(d,J=14.5Hz,1H,CH),6.20(dd,J=17.3,10.5Hz,2H,CH),5.95(d,J=10.5Hz,2H,ArH),5.78(s,4H,CH2),4.46(d,J=5.4Hz,2H,NCH2),4.16(t,J=6.2Hz,2H,SCH2),3.82-3.69(m,4H,OCH2),3.03(s,3H,NCH3),2.76-2.52(m,4H,CH2),0.82(s,6H,CH3). The results of the carbon NMR spectrum of SLD2 are: 13 C NMR (151MHz, CDCl3) δ (ppm): 174.29, 173.23, 170.44, 166.51, 163.29, 156.85, 150.33, 151.54, 146.24, 137.19, 13 4.31,131.12,131.99,131.77,131.29,129.96,129.66,129.31,129.21,128.56,128.44,128.31,127.78,127.61, 127.55,127.34,126.89,126.77,126.58,126.33,125.22,123.97,117.4,115.35,114.26,114.19,112.56,110.79,63.41,62.33,60.78,58.68,50.75,42.89,43.67,39.57,36.49,34.98,32.53,29.55,28.89,24.21,21.30,14.33.

[0164] Example 3

[0165] An organic compound SLD3, whose structural formula is shown below:

[0166] The main difference between the synthesis method of the organic compound SLD3 and the above-mentioned SLD1 is that the hydroxyl compound used in step (1) is different.

[0167] Example 4

[0168] An organic compound SLD4, whose structural formula is shown below:

[0169] The main difference between the synthesis method of the organic compound SLD4 and the above-mentioned SLD2 is that the hydroxyl compound used in step (1) is different.

[0170] Example 5

[0171] An organic compound SLD5, its structural formula is shown below:

[0172] The main difference between the synthesis method of the above organic compound SLD5 and the above SLD1 is that the hydroxyl compound used in step (1) is different.

[0173] Example 6

[0174] An organic compound SLD6, whose structural formula is shown below:

[0175] The main difference between the synthesis method of the above organic compound SLD6 and the above SLD2 is that the hydroxyl compound used in step (1) is different.

[0176] Example 7

[0177] An organic compound SLD7, whose structural formula is shown below:

[0178] The main difference between the synthesis method of the organic compound SLD7 and the above-mentioned SLD1 is that the hydroxyl compound used in step (1) is different.

[0179] Example 8

[0180] An organic compound SLD8, whose structural formula is shown below:

[0181] The main difference between the synthesis method of the organic compound SLD8 and the above-mentioned SLD2 is that the hydroxyl compound used in step (1) is different.

[0182] Example 9

[0183] An organic compound SLD9, whose structural formula is shown below:

[0184] The main difference between the synthesis method of the above organic compound SLD9 and the above SLD1 is that the hydroxyl compound used in step (1) is different.

[0185] Example 10

[0186] An organic compound SLD10, whose structural formula is shown below:

[0187] The main difference between the synthesis method of the organic compound SLD10 and the synthesis method of SLD2 is that the hydroxyl compound used in step (1) is different.

[0188] Example 11

[0189] An organic compound SLD11 has the following structural formula:

[0190] The main difference between the synthesis method of the organic compound SLD11 and the above-mentioned SLD1 is that the hydroxyl compound used in step (1) is different.

[0191] Example 12

[0192] An organic compound SLD12, whose structural formula is shown below:

[0193] The main difference between the synthesis method of the above organic compound SLD12 and the above SLD2 is that the hydroxyl compound used in step (1) is different.

[0194] Example 13

[0195] An organic compound SLD13, whose structural formula is shown below:

[0196] The main difference between the synthesis method of the organic compound SLD13 and the above-mentioned SLD1 is that the hydroxyl compound used in step (1) is different.

[0197] Example 14

[0198] An organic compound SLD14, whose structural formula is shown below:

[0199] The main difference between the synthesis method of the organic compound SLD14 and the above-mentioned SLD2 is that the hydroxyl compound used in step (1) is different.

[0200] Results characterization:

[0201] (1) DFT theory simulation calculation

[0202] To compare the microscopic nonlinearity, charge transfer, and stereo configuration of different chromophores, the chromophore SLD1-14 provided in the examples of this application was subjected to structural optimization and theoretical calculation of the first-order hyperpolarizability. The theoretical calculations were performed using the Gaussian 09 software package, based on the B3LYP method of the density functional theory (DFT) combined with the 6-31g(d) basis set. During the calculations, we assumed that all molecules were in the trans configuration, optimized the chromophore structure, and calculated the energy levels, dipole moments, electron cloud density, and microscopic first-order hyperpolarizability β of the ground and excited states of the chromophore. The results are shown in Table 1 below.

[0203] Table 1 DFT calculation data of various organic compounds

[0204] Table 1 shows that the first-order hyperpolarizabilities β of SLD1 to SLD14 increase with increasing donor strength (as reflected by decreasing ΔE). Although SLD1 and SLD2 contain different numbers of crosslinkable groups, their donors are both common aniline donors, resulting in similar first-order hyperpolarizabilities.

[0205] (2) Thermal stability and spectral absorption characteristics

[0206] The spectral absorption characteristics and thermal stability of each chromophore were tested. Table 2 below summarizes the test results for chromophores SLD1, SLD2, SLD3, and SLD4. The thermal stability of the chromophores can be characterized by their thermogravimetric curves. The thermogravimetric curve for chromophore SLD1 is shown in Figure 2A, and the thermogravimetric curve for chromophore SLD2 is shown in Figure 2B. The UV-visible spectra of chromophore SLD1 in different solvents and films are shown in Figure 3. The UV-visible spectra of chromophore SLD2 in different solvents and films are shown in Figure 4.

[0207] Table 2

[0208] Note: T in Table 2 d and T g It can be known from the thermogravimetric curve and differential scanning calorimetry curve of each chromophore; max a is the maximum absorption wavelength of each chromophore in chloroform solvent, λ max b It is the maximum absorption wavelength of each chromophore in the cross-linked film (specifically, cross-linking is achieved by heating at 150°C for 30 minutes).

[0209] It can be seen from Table 2 that the chromophores SLD1 to SLD4 provided in the examples of the present application have high thermal stability (T g Above 150℃), it is conducive to the preparation of electro-optically active and stable thin films. Among them, SLD2 has better thermal stability than SLD1 with similar structure. g As high as 200℃, its thermal decomposition temperature T d The maximum absorption wavelength of SLD2 in chloroform, which has an additional anthracene group compared to SLD1, is 753 nm, which is close to 749 nm of SLD1. This proves that the cross-linkable group (specifically the anthracene group) does not affect the light absorption performance of the main structure of the chromophore too much. The larger λ max a This indicates that the chromophore possesses a large first-order hyperpolarizability. Furthermore, the maximum absorption wavelength of the cross-linked SLD2-containing film is nearly identical to that of SLD1. Furthermore, the anthracene absorption peak of the cross-linked chromophore-containing films decreases compared to the uncross-linked films, indicating the participation of the anthracene group in the cross-linking reaction. Furthermore, a comparison between SLD4 and SLD3 shows a similar pattern to that between SLD1 and SLD2.

[0210] (3) Electro-optical performance of assembled devices

[0211] In order to illustrate the conversion of the microscopic hyperpolarizability β of the organic compound provided in the embodiment of the present application into the macroscopic r 33 The ability of the value is first made into an electro-optically active film. Different chromophores are dissolved in freshly distilled dibromomethane respectively, and the obtained solution is filtered through a 0.2mm polytetrafluoroethylene (abbreviated as PTFE) filter and spin-coated on an indium oxide (ITO) glass substrate. After heating at 50°C to remove the solvent dibromomethane, a dry film layer is obtained. The upper surface of the dry film layer is connected to a metal electrode (such as a gold electrode), and the gold electrode is electrically connected to the ITO electrode to apply an electric field to polarize the film layer and then cross-link to obtain a stable film exhibiting electro-optical activity. The specific operation process is: 1) First, a polarizing electric field with an intensity of 10V / μm is applied between the gold electrode and the ITO electrode, and the temperature is raised to 100°C at a rate of 10°C / min. 2) The electric field intensity was then gradually increased to 100-130 V / μm with a step voltage of 1 V / minute. At the same time, the film was heated at 100°C for 5 minutes, 110°C for 5 minutes, 120°C for 5 minutes, 130°C for 5 minutes, 140°C for 5 minutes, and 150°C for 10 minutes. After each film sample was cooled to room temperature, the polarization properties of the obtained electro-optically active film at a wavelength of 1310 nm were tested using the Teng-Man simple reflection method. The relevant results are summarized in Table 3.

[0212] The experimental setup for measuring the electro-optic coefficient using a simple reflection method is shown in FIG5 . The signal light source used is a 1310 nm laser in the communication band. The two polarizers are perpendicular to each other, and the incident angle θ is 45°. After the incident light passes through the ITO glass and the electro-optically active film, it is reflected and emitted from the surface of the metal electrode, interferes with the polarizer 2, and is detected by a phase-locked amplifier and a detector. Different modulation voltages are applied to both sides of the electro-optically active film, and the refractive index of the film changes, causing the optical path and phase state of the incident light to change. After the reflected light interferes with the polarizer 2, polarized light in different phase states exhibits different extinction phenomena. The light intensity detected by the detector will have a certain relationship with the modulation voltage, so that the electro-optic coefficient r of the polarized film at a wavelength of 1310 nm can be calculated. 33 Among them, thin ITO electrodes with low reflectivity and good transparency are used to minimize multiple reflections.

[0213] Table 3 Relevant test data of electro-optical devices assembled with various chromophores

[0214] Note: In Table 3, ρ N represents the number density of the polarizable compound (assuming a mass density of 1 g / cm 3 ). 33 / E p It is also called the average polarization efficiency, which is based on the r measured at different polarization field strengths of each film. 33 The polarization curve obtained by linear least squares regression is also the slope of the polarization curve, which is the average value of multiple polarization experiments. 33 / (E p ρ N ) represents the polarization efficiency per number density, which can better reflect the polarization of the compound.

[0215] FIG6 shows the polarization curve of the film SLD1 after self-crosslinking of the embodiment of the present application, and FIG7 shows the polarization curve of the film SLD2 after crosslinking of the embodiment of the present application. The horizontal axis is the polarization field strength, and the vertical axis is the r of the film at each polarization field strength. 33 The relevant performance indicators are summarized in Table 3. The data points in Figures 6 and 7 were obtained as follows: after the electric field strength applied between the gold electrode and the ITO electrode in step 2) above reached the electric field strength corresponding to each data point, the heating operation in step 2) above was performed to achieve self-crosslinking, and the electro-optically active film was obtained after cooling, and its relevant properties were tested.

[0216] From Table 3 and Figures 6 and 7, it can be seen that the average polarization efficiency of the electro-optical active film formed by polarization and cross-linking of the dry film containing SLD1 is about 2.03nm 2 / V 2, the maximum electro-optic coefficient r obtained under the polarization field 33 The average polarization efficiency of SLD2 after cross-linking is about 1.58nm 2 / V 2 , maximum electro-optic coefficient r 33 It is about 198pm / V. Among them, the average polarization efficiency and maximum electro-optic coefficient of chromophore SLD1 after cross-linking are higher than those of chromophore SLD2. This is mainly because the dianthracene structure of chromophore SLD2 leads to an increase in the molecular weight of the chromophore, resulting in a decrease in the number density of the chromophore. The difference in electro-optic coefficient is mainly affected by the number density and polarization efficiency of the chromophore, while the above-mentioned first-order hyperpolarizability is less affected by this. However, it should be noted that although the electro-optic coefficient of chromophore SLD1 is larger, its glass transition temperature Tg is not as high as that of chromophore SLD2. In general, the use of these two chromophores SLD1 and SLD2 can obtain electro-optically active films with good comprehensive performance, which can take into account higher Tg. g and a higher electro-optical coefficient max.r 33 wait.

[0217] The above merely represents several exemplary embodiments of the present application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the present application. It should be noted that a person of ordinary skill in the art would be able to make various modifications and improvements without departing from the spirit of the present application, and these modifications and improvements fall within the scope of protection of the present application. Therefore, the scope of protection of the present application shall be determined by the appended claims.

[0218] It should be understood that the first, second, and various numerical numbers involved in this document are only for the convenience of description and are not intended to limit the scope of this application. In the various embodiments of this application, the size of the sequence number of each process does not mean the order of execution. Some or all steps can be executed in parallel or in sequence. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of this application.

[0219] In this application, "and / or" describes the relationship between related objects, indicating that three possible relationships exist. For example, "A and / or B" can mean: A exists alone, A and B exist simultaneously, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the related objects are in an "or" relationship.

[0220] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

Claims

1. An organic compound, characterized in that The organic compound has the general structural formula shown in formula (I): In formula (I), A represents an electron acceptor, D represents an electron donor, Z represents a sulfur atom, an oxygen atom or NH, and R1 is selected from substituted or unsubstituted C1-C 10 Alkylene; n is an integer selected from 0-2; X1 includes at least one first crosslinkable group, X2 includes at least one second crosslinkable group, and a cycloaddition crosslinking reaction can occur between the first crosslinkable group and the second crosslinkable group.

2. The organic compound according to claim 1, characterized in that The first crosslinkable group and the second crosslinkable group are independently selected from one or more of anthracene group, acrylate group, maleamide group, furan group, azidoaryl group and alkynyloxy group.

3. The organic compound according to claim 1 or 2, characterized in that Said X1 and X2 are independently selected from One or more of; the position marked with * is the connection position.

4. The organic compound according to any one of claims 1 to 3, characterized in that The Z is a sulfur atom, and R1 is -CH2-CH2.

5. The organic compound according to any one of claims 1 to 4, characterized in that The D independently includes an aromatic amine structure or a heteroaromatic amine structure containing a tertiary amino nitrogen atom.

6. The organic compound according to claim 5, characterized in that The D comprises any structure represented by formula (d-1) to formula (d-6) which is substituted or unsubstituted: in,*, The marked position is the connection position, the position marked with * is connected to -OCO-X2, each a is independently selected from an integer of 1-3, each b is independently selected from an integer of 0-3, and R2, R3, and R4 are independently selected from substituted or unsubstituted alkyl groups.

7. The organic compound according to any one of claims 1 to 6, characterized in that The A comprises a structure shown in formula (A-1) or formula (A-2): in, The marked position is the connection position, X is independently selected from oxygen atom, sulfur atom, N(R8) or CH2, R7 is independently selected from at least one of cyano, nitro, trihalomethyl, fluorine atom, sulfonic acid, trifluoromethanesulfonyl each time it appears, R5 and R6 are independently selected from one of substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and R8 is a hydrogen atom, or a substituted or unsubstituted alkyl.

8. The organic compound according to claim 7, characterized in that A is a structure represented by formula (A-1), and each R7 is a cyano group, one of R5 and R6 is a trifluoromethyl group, and the other is a phenyl group; X is an oxygen atom, a sulfur atom, NH or CH2.

9. A film, characterized in that: The film comprises a cross-linked product of the organic compound according to any one of claims 1 to 8.

10. The film according to claim 9, characterized in that The glass transition temperature of the film is greater than or equal to 150°C.

11. The film according to claim 9 or 10, characterized in that The film is an electro-optically active film, and the maximum electro-optic coefficient of the electro-optically active film is greater than or equal to 190 pm / V.

12. A method for preparing an electro-optically active thin film, characterized in that: The following steps are involved: Applying a solution containing the organic compound according to any one of claims 1 to 8 on a substrate and drying to form a film layer; Applying an electric field to the film layer and heating it at a first temperature to polarize the organic compound; The polarized film layer is further heated to a second temperature to allow the organic compound in the film layer to self-crosslink, and then the temperature is lowered to obtain an electro-optically active film.

13. Use of the organic compound according to any one of claims 1 to 8, the thin film according to any one of claims 9 to 11, and the electro-optically active thin film prepared by the preparation method according to claim 12 in components of optical communication systems, solar cells, organic electroluminescent devices, and organic photoluminescent devices.

14. The use according to claim 13, characterized in that The components of the optical communication system include one or more of electro-optical devices, optical switches, straight waveguides, bent waveguides, single-mode optical splitters, routers, filters, optical interconnectors, and resonators.

15. An electro-optical device, characterized in that: It comprises a film as described in any one of claims 9 to 11, or an electro-optically active film prepared by the preparation method as described in claim 12.

16. The electro-optical device according to claim 15, characterized in that The electro-optical device includes one or more of an electro-optic modulator, a coupler, a terahertz detector, an electro-optic frequency shifter, and a frequency comb source.

17. An optical communication system, characterized in that: At least some of the components of the optical communication system include a film as claimed in any one of claims 9 to 11, or an electro-optically active film made by the preparation method as claimed in claim 12.

18. A phased array laser radar system, characterized in that: It comprises a film as described in any one of claims 9 to 11, or an electro-optically active film prepared by the preparation method as described in claim 12.

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