Chiral binaphthalene bridged perylene diimide circular polarization luminescent liquid crystal compound and preparation method thereof
Through the method of bridging chiral binaphthalene and perylene diimide, the chiral binaphthalene bridged perylene diimide is designed and synthesized, and the circularly polarized luminescent material based on binaphthalene in the prior art is solved. The problem of insufficient liquid crystal properties has achieved stable mesomorphic phase and aggregation-induced effects, and has a wide range of applications for displays and light emitting diodes.
Patent Information
- Application Number
- CN202411398041.0
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-10-09
- Publication Date
- 2025-02-07
AI Technical Summary
Among the existing circularly polarized luminescent materials based on binaphthalene, liquid crystal properties are fewer, and axial chiral molecules may cause the circular dichromatic spectral signal to weaken or disappear under solution conditions, and most of them exist in doping form, resulting in waste of resources.
Through the strategy of bridging chiral binaphthalene and perylene diimide, a circularly polarized luminescent liquid crystal compound of chiral binaphthalene bridge is designed and synthesized, and the plane conjugation of molecules is enhanced by using alkynyl linkage and inhibiting the coupling. The rotation of the dihedral angle of naphthalene promotes the self-assembly of molecules to form a columnar phase.
It has achieved a stable mesomorphic phase formed over a wide temperature range, possesses room temperature liquid crystal properties, and optically exhibits aggregation-induced effect, and has potential applications in fields such as electronic books, high-quality displays and light-emitting diodes.
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Abstract
Description
Technical Field
[0001] The invention relates to the technical field of chiral liquid crystal material preparation, in particular to a method for preparing a chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound. Background Art
[0002] Chiral liquid crystal refers to a liquid crystal compound containing one or more asymmetric carbon atoms in the liquid crystal molecular structure. Chiral liquid crystals can be used in display devices with fast switching, high contrast and wide viewing angle due to their spontaneous polarization characteristics, and are widely used in the fields of molecular electronics, optoelectronics, photoconductivity and electroluminescent devices. Since the chiral source of point-chiral liquid crystal molecules is on the carbon chain, far away from the chromophore, there may be a phenomenon of weakening or disappearing circular dichroism spectral signals under solution conditions. The chiral source of axial chiral liquid crystals is on the axis connecting the chromophores, which can well avoid the problem of weakening or disappearing circular dichroism spectral signals. However, most of the liquid crystals based on axial chirality are mainly in the form of doping, that is, the chiral additives are mixed with liquid crystal compounds in a certain proportion, which causes a waste of resources to a certain extent. At present, only a very few examples of circularly polarized luminescent materials based on binaphthyl reported at this stage have liquid crystal properties, and the liquid crystal unit is a rod-shaped molecule. This may be due to two reasons: first, the conjugated structure is not large enough, which is not conducive to the orderly stacking of the mesomorphic phase; second, the σ single bond in the axial chiral molecule can rotate at a large angle, which makes it difficult to form a regular arrangement. Therefore, it is of great significance and certain challenges to synthesize new circularly polarized luminescent liquid crystal materials using cheap and readily available raw materials. Summary of the invention
[0003] The purpose of the present invention is to provide a novel circularly polarized luminescent liquid crystal material and a preparation method thereof, specifically, a chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound and a preparation method thereof.
[0004] The present invention adopts a strategy of bridging chiral binaphthyl and perylene diimide, which, on the one hand, expands the conjugated plane to limit the rotation angle of the σ single bond (i.e., controls the dihedral angle), and on the other hand, introduces an alkyl chain to enhance the solubility, thereby facilitating the self-assembly of the mesomorphic phase; a compound having a molecular structure shown in the following formula I or II is designed and synthesized, namely a chiral binaphthyl bridged perylene diimide circularly polarized luminescent liquid crystal compound.
[0005] The molecular structures of Formula I and Formula II are as follows:
[0006]
[0007] In Formula I and Formula II, R 1 -C6H 13 、-C8H 10 , -C 10 H 21 Any one of R2 -C8H 17 , -C 10 H 21 , -C 12 H 25 Any one of .
[0008] The chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound is prepared by using 3-ethynyl-2,2-dimethoxy-1,1-binaphthyl or 3,3'-diethynyl-2,2'-dimethoxy-1,1'-binaphthyl as one of the reactants and another reactant PDI-n through a palladium-catalyzed Sonogashira cross-coupling reaction to obtain the liquid crystal compound. The reactant PDI-n can be any one of 5-bromo-2,9-bis(2-hexyloctyl)[2,1,9-def:6,5,10-d'e'f]diisoquinoline-1,3,8,10(2H,9H)-tetraketone, 5-bromo-2,9-bis(2-octyldecyl)[2,1,9-def:6,5,10-d'e'f]diisoquinoline-1,3,8,10(2H,9H)-tetraketone, and 5-bromo-2,9-bis(2-decyldodecyl)[2,1,9-def:6,5,10-d'e'f]diisoquinoline-1,3,8,10(2H,9H)-tetraketone. The preparation reaction principle is as follows:
[0009]
[0010]
[0011] For the R / S-BPDI1-n type liquid crystal compound shown in Formula I, the specific preparation method steps are as follows:
[0012] S1. Add R / S-B1, PDI-n, Pd(PPh3)4, CuI and a mixture of toluene and triethylamine into a reaction vessel and react at 85°C for 24 hours under argon protection. The molar ratio of R / S-B1, PDI-n, Pd(PPh3)4 and CuI is 10:5:1:2. Toluene and triethylamine (TOL / EtN3) are mixed in a volume ratio of 2:1 to form a mixed solution.
[0013] S2. After the reaction is completed, the mixture is extracted with dichloromethane, the organic phase is dried with anhydrous MgSO4, filtered, concentrated, and the crude product is separated and purified by silica gel column chromatography, and recrystallized with ethyl acetate and ethanol to obtain a red granular solid, which is the R / S-BPDI1-n liquid crystal compound shown in Formula I. The eluent for silica gel column chromatography is a mixture of toluene and petroleum ether in a volume ratio of 7:1.
[0014] For the R / S-BPDI2-n type liquid crystal compound shown in formula II, the preparation method steps are as follows:
[0015] S1. Add R / S-B2, PDI-n, Pd(PPh3)4, CuI and a mixture of toluene and triethylamine into a reaction vessel and react at 85°C for 48 hours under argon protection. The molar ratio of R / S-B2, PDI-n, Pd(PPh3)4 and CuI is 5:10:1:2. Toluene and triethylamine (TOL / EtN3) are mixed in a volume ratio of 2:1 to form a mixed solution.
[0016] S2. After the reaction is completed, the mixture is extracted with dichloromethane, the organic phase is dried with anhydrous MgSO4, filtered, concentrated, and the crude product is separated and purified by silica gel column chromatography, and recrystallized with ethyl acetate and ethanol to obtain a red granular solid, which is the R / S-BPDI2-n liquid crystal compound shown in Formula II. The eluent for silica gel column chromatography is a mixture of toluene and petroleum ether in a volume ratio of 4:1.
[0017] Compared with the prior art, the present invention is beneficial in that:
[0018] (1) Most of the chiral liquid crystals designed with binaphthyl as the skeleton reported so far are only introduced as dopants into known liquid crystals to induce chiral liquid crystal properties. They are binary mixtures or even multi-component mixtures, and most of them are cholesteric liquid crystals. Different from this, the present invention uses alkynyl groups to connect binaphthyl with perylene diimide. On the one hand, the planar conjugation of the entire molecule is enhanced to a certain extent. On the other hand, the conjugated structure of perylene diimide is large enough to inhibit the rotation of the dihedral angle of binaphthyl. Therefore, the molecules can self-assemble in a certain arrangement and stacking form to form a columnar phase, thereby obtaining chiral discotic liquid crystal molecules based on binaphthyl.
[0019] (2) Tests show that the R / S-BPDI1-n type liquid crystal compound and the R / S-BPDI2-n type liquid crystal compound prepared by the present invention form a stable mesomorphic phase in a wide temperature range and are a room temperature liquid crystal. In addition, the compounds of the present invention also exhibit an aggregation induction effect optically, and have potential application value in electronic books, high-definition displays, light-emitting diodes, etc.
[0020] Other advantages, objectives and features of the present invention will be embodied in part through the following description, and in part will be understood by those skilled in the art through study and practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS
[0021] Figure 1 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI1-1 obtained in Example 1.
[0022] Figure 2 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI1-2 obtained in Example 1.
[0023] Figure 3 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI1-3 obtained in Example 1.
[0024] Figure 4 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI2-1 obtained in Example 2.
[0025] Figure 5 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI2-2 obtained in Example 2.
[0026] Figure 6 This is the hydrogen nuclear magnetic resonance spectrum of the target compound R / S-BPDI2-3 obtained in Example 2.
[0027] Figure 7 This is a graph showing the aggregation-inducing effect of the target compound R / S-BPDI1-1 obtained in Example 1.
[0028] Figure 8 This is a graph showing the aggregation-inducing effect of the target compound R / S-BPDI2-1 obtained in Example 2.
[0029] Fig. 9 This is the polarized texture image of the target compound R / S-BPDI1-1 obtained in Example 1.
[0030] Fig.10 This is the polarized texture image of the target compound R / S-BPDI1-2 obtained in Example 1.
[0031] Fig.11 This is the polarized texture image of the target compound R / S-BPDI1-3 obtained in Example 1.
[0032] Fig.12 This is the polarized texture image of the target compound R / S-BPDI2-1 obtained in Example 2.
[0033] Fig.13 This is the polarized texture image of the target compound R / S-BPDI2-2 obtained in Example 2.
[0034] Fig.14 This is the polarized texture image of the target compound R / S-BPDI2-3 obtained in Example 2.
[0035] Fig.15 This is the CD chart of the target compound R / S-BPDI1-1 obtained in Example 1.
[0036] Fig.16 This is the CD chart of the target compound R / S-BPDI2-1 obtained in Example 2. DETAILED DESCRIPTION
[0037] The preferred embodiments of the present invention are described below in conjunction with the accompanying drawings. It should be understood that the preferred embodiments described herein are only used to illustrate and explain the present invention, and are not used to limit the present invention.
[0038] Example 1
[0039] Synthesis of R / S-BPDI1-n liquid crystal compounds: R / S-B1 (0.30mmol), PDI-n (0.15mmol), Pd(PPh3)4 (0.03mmol), CuI (0.06mmol) were weighed in a 50mL reaction tube, 10mL of a mixture of toluene and triethylamine (toluene and triethylamine volume ratio 2:1) was measured with a syringe and slowly injected into the reaction tube, and reacted at 85°C for 24h under argon protection. After the reaction was completed, dichloromethane was used for extraction, the organic phase was dried with anhydrous MgSO4, filtered, concentrated, and the crude product was chromatographed on a silica gel column (the eluent was a mixture of toluene and petroleum ether, volume ratio V TOL :V PE =7:1) separation and purification, and recrystallization with ethyl acetate and ethanol to obtain a red granular solid, which is a R / S-BPDI1-n type liquid crystal compound.
[0040] When the reactant PDI-n has R 1 -C6H 13 , R 2 -C8H 17 When , the corresponding product is R / S-BPDI1-1, and the yield is 90%.
[0041] When the reactant PDI-n has R 1 -C8H 10 , R 2 For -C 10 H 21 When , the corresponding products are R / S-BPDI1-2, and the yields are 87%.
[0042] When the reactant PDI-n has R 1 For -C 10 H 21 , R 2 For -C 12 H 25 When , the corresponding products are R / S-BPDI1-3, and the yields are 91%.
[0043] Example 2
[0044] Synthesis of R / S-BPDI2-n liquid crystal compounds: R / S-B2 (0.15mmol), PDI-n (0.30mmol), Pd(PPh3)4 (0.03mmol), CuI (0.06mmol) were weighed in a 50mL reaction tube, 10mL of a mixture of toluene and triethylamine (toluene and triethylamine volume ratio 2:1) was measured with a syringe and slowly injected into the reaction tube, and reacted at 85°C for 48h under argon protection. After the reaction was completed, dichloromethane was used for extraction, the organic phase was dried with anhydrous MgSO4, filtered, concentrated, and the crude product was chromatographed on a silica gel column (the eluent was a mixture of toluene and petroleum ether, volume ratio V TOL :V PE =4:1) separation and purification, and recrystallization with ethyl acetate and ethanol to obtain a red granular solid, which is a R / S-BPDI2-n type liquid crystal compound.
[0045] When the reactant PDI-n has R 1 -C6H 13 , R 2 -C8H 17 When , the corresponding product is R / S-BPDI2-1, and the yield is 75%.
[0046] When the reactant PDI-n has R 1 -C8H 10 , R 2 For -C 10 H 21 When , the corresponding product is R / S-BPDI2-2, and the yield is 60%.
[0047] When the reactant PDI-n has R 1 For -C 10 H 21 , R 2 For -C 12 H 25 When , the corresponding product is R / S-BPDI2-3, and the yield is 72%.
[0048] The performance characterization tests of the products prepared in Examples 1 and 2 are as follows:
[0049] (1) H NMR spectra of the six products R / S-BPDI1-1, R / S-BPDI1-2, R / S-BPDI1-3, R / S-BPDI2-1, R / S-BPDI2-2, and R / S-BPDI2-3 1 H NMR (400MHz, CDCl3) is Figure 1-Figure 6 .
[0050] Figure 1 The compound R / S-BPDI1-1 shown has a hydrogen NMR spectrum1 H NMR (400MHz, CDCl3): δ10.48(d,J=8.3Hz,1H),8.79(s,1H),8.59(ddd,J=17.2,11.3,8.1 Hz,5H),8.33(s,1H),8.09(d,J=9.1Hz,1H),7.95(d,J=11.9Hz,2H),7.54(d,J=9.1Hz,1H) ,7.46(d,J=9.0Hz,1H),7.39–7.39–7.35(d,J=9.5Hz,1H),7.33–7.28(m,2H),7.23–7.17 (m,2H),4.10(s,4H),3.90(s,3H),3.69(s,3H),1.99(m,2H),1.29(m,48H),0.83(m,12H).
[0051] Figure 2 The shown compound R / S-BPDI1-2 has a hydrogen NMR spectrum 1 H NMR (400MHz, CDCl3): δ10.46(d,J=7.9Hz,1H),8.78(s,1H),8.58(ddd,J=21.1,19.3,8.1H z,5H),8.32(s,1H),8.09(d,J=9.2Hz,1H),7.99–7.91(d,J=12.1Hz,2H),7.54(d,J=9.2Hz, 1H),7.49(d,J=9.7Hz,1H),7.39–7.35(d,J=9.4Hz,1H),7.33–7.28(m,2H),7.23–7.17(m,2 H),4.09(s,4H),3.90(s,3H),3.69(s,3H),1.97(m,2H),1.46–1.15(m,64H),0.82(m,12H).
[0052] Figure 3 The shown compound R / S-BPDI1-3 has a hydrogen NMR spectrum 1H NMR (400MHz, CDCl3): δ10.50(d,J=8.2Hz,1H),8.81(s,1H),8.65–8.55(ddd,J=17.2,11.3,8 .1Hz,5H),8.33(s,1H),8.09(d,J=9.0Hz,1H),7.95(d,J=13.5,Hz,2H),7.54(d,J=9.2Hz,1H ),7.46(d,J=9.9Hz,1H),7.39–7.35(d,J=9.3Hz,1H),7.33–7.28(m,2H),7.23–7.17(m,2H), 4.10(s,4H),3.89(s,3H),3.69(s,3H),1.97(m,2H),1.42–1.17(m,80H),0.88–0.80(m,12H).
[0053] Figure 4 The compound R / S-BPDI2-1 shown has a hydrogen NMR spectrum 1 H NMR (400MHz, CDCl3): δ10.38(s,2H),8.48(d,J=38.5Hz,16H),8.03(s,2H),7.53(m,2H),7.4 2(d,J=7.7Hz,2H),4.11(s,6H),3.84(s,8H),1.97(m,4H),1.25(m,96H),0.82-0.72(m,24H).
[0054] Figure 5 The compound R / S-BPDI2-2 shown in the figure has a hydrogen NMR spectrum. 1 H NMR (400MHz, CDCl3): δ10.38(s,2H),8.57(d,J=38.5Hz,16H),8.06(s,2H),7.38(m,2H),7.17 (d,J=7.7Hz,2H),4.07(s,6H),3.92(s,8H),1.97(m,4H),1.22(m,128H),0.84-0.76(m,24H).
[0055] Figure 6 The compound R / S-BPDI2-3 shown in the figure has a hydrogen NMR spectrum. 1 H NMR (400MHz, CDCl3): δ10.41 (s, 2H), 8.51 (d, J = 38.5Hz, 16H), 8.02 (s, 2H), 7.51 (m, 2H), 7.42(m,2H),4.11(s,6H),3.89(s,8H),2.03(m,4H),1.24(m,160H),0.84-0.74(m,24H).
[0056] The above-mentioned hydrogen nuclear magnetic spectrum proves that the preparation method of the present invention successfully synthesizes each product.
[0057] (2) Testing the aggregation induction effect of the product: Since the product is soluble in THF, a THF and H2O system was used to test the aggregation induction. Weigh the product R / S-BPDI1-1 (1.2 mg) and dissolve it in 10 mL of dichloromethane. Take 1 mL of the solution into 10 test tubes respectively. After the dichloromethane evaporates, add THF / H2O mixed systems with a ratio of 0:10, 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2, and 9:1 to the test tubes to make the volume 10 mL. Then test the fluorescence emission of each sample. The test results are shown in Figure 7 R / S-BPDI1-2 and R / S-BPDI1-3 were tested using the same test method and the results were similar to Figure 7 resemblance.
[0058] The compound R / S-BPDI2-1 (2.1 mg) was weighed and dissolved in 10 mL of dichloromethane, and 1 mL of the solution was taken into 10 test tubes respectively. After the dichloromethane evaporated, THF / H2O mixed systems with a ratio of 0:10, 1:9, 2:8, 3:7, 4:6, 5:5, 6:4, 7:3, 8:2, and 9:1 were added to the test tubes to make the volume 10 mL, and then the fluorescence emission of each sample was tested respectively. The test results are shown in Figure 8 R / S-BPDI2-2 and R / S-BPDI2-3 were tested using the same test method and the results were similar to Figure 8 resemblance.
[0059] Depend on Figure 7 and Figure 8 It can be seen that the product synthesized by the present invention exhibits an aggregation-inducing effect optically.
[0060] (3) Testing the mesomorphic properties of the products: 2.0 mg of the R / S-BPDI1-n series compounds were placed on a glass slide and placed on a hot plate. The compounds were heated to a molten state using the hot plate and then slowly cooled. The phase changes of the compounds during the cooling process were observed using a POM microscope. The test results are shown in Figure 9-11 2.0 mg of R / S-BPDI2-n series compounds were placed in a glass slide and placed on a hot plate. The compounds were heated to a molten state and then slowly cooled using the hot plate. The phase changes of the compounds during cooling were observed using a POM microscope. The test results are shown in Figure 12-14 It can be seen from the polarized texture diagram that the compound synthesized in the present invention has a classic hexagonal columnar phase structure of discotic liquid crystals. Combined with XRD characterization, it can be more clearly proved that the compound prepared in the present invention has a classic hexagonal columnar phase structure of discotic liquid crystals.
[0061] (4) Testing the chirality of the product: 1.2 mg of each of the R-BPDI1-1 and S-BPDI1-1 series compounds were dissolved in 10 mL of dichloromethane, and then 1 mL of each solution was taken into a test tube and diluted to 10 mL with dichloromethane. The CD signal of R / S-BPDI1-1 was tested using a circular dichroism spectrometer. The test results are shown in Figure 15. R / S-BPDI1-2 and R / S-BPDI1-3 were tested using the same test method, and the results were the same as Fig.15 2.0 mg of R-BPDI2-1 and S-BPDI2-1 series compounds were dissolved in 10 mL of dichloromethane, and then 1 mL of the solution was taken into a test tube and diluted to 10 mL with dichloromethane. The CD signal of R / S-BPDI2-1 was tested using a circular dichroism spectrometer. The test results are shown in Fig.16 R / S-BPDI2-2 and R / S-BPDI2-3 were tested using the same test method and the results were similar to Fig.16 The CD patterns of the products show the existence of chirality.
[0062] In the prior art, in 2015, Takuya Nakashima et al. used binaphthylamine and 3,4,9,10-perylenetetracarboxylic dianhydride to carry out imidization reaction to obtain compound A with the following structural formula, but it is not a liquid crystal molecule. In addition, in 2019, Qing Guo He's research group synthesized a binaphthyl derivative B containing the luminescent element pyrene (structural formula B below), which still has no liquid crystal properties. Among the reported CPL materials based on binaphthyl as the core, almost all of them are doped into the liquid crystal as a chiral additive to induce chiral self-assembly to increase the luminescence asymmetry factor g. lum . The binaphthyl derivatives synthesized by the present invention are chiral discotic liquid crystal molecules, which do not need to be used as chiral additives and can exhibit liquid crystal properties by themselves, and the retention of chirality is also proved in the CD diagram. Tests have shown that the two types of compounds form a stable mesomorphic phase in a wide temperature range and are a room temperature liquid crystal. The synthesis method of the compounds of the present invention can provide a good example for the synthesis of chiral liquid crystals. This type of compound also exhibits an aggregation-inducing effect optically. It has potential application value in electronic books, high-definition displays, light-emitting diodes, etc.
[0063]
[0064] The above description is only a preferred embodiment of the present invention and does not constitute any form of limitation to the present invention. Although the present invention has been disclosed as a preferred embodiment as above, it is not intended to limit the present invention. Any technician familiar with the profession can make some changes or modifications to equivalent embodiments of equivalent changes using the technical contents disclosed above without departing from the scope of the technical solution of the present invention. However, any simple modification, equivalent change and modification made to the above embodiments based on the technical essence of the present invention without departing from the content of the technical solution of the present invention still falls within the scope of the technical solution of the present invention.
Claims
1. A chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound, characterized in that: The molecular structure is shown in Formula I or Formula II: In Formula I and Formula II, R 1 -C6H 13 、-C8H 10 , -C 10 H 21 Any one of R 2 -C8H 17 , -C 10 H 21 , -C 12 H 25 Any one of .
2. A method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound as claimed in claim 1, characterized in that: R / S-B1 or R / S-B2 is used as one of the reactants and is prepared by a palladium-catalyzed Sonogashira cross-coupling reaction with another reactant PDI-n; wherein the molecular structures of R / S-B1, R / S-B2, and PDI-n are as follows: In the formula, R 1 -C6H 13 、-C8H 10 , -C 10 H 21 Any one of R 2 -C8H 17 , -C 10 H 21 , -C 12 H 25 Any one of .
3. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 2, characterized in that: Here are the steps: S1. Add R / S-B1 or R / S-B2, PDI-n, Pd(PPh3)4, CuI and a mixture of toluene and triethylamine into a reaction vessel, and react at 85°C for 24-48h under argon protection; S2. After the reaction is completed, extraction is carried out with dichloromethane, the organic phase is dried over anhydrous MgSO4, filtered, concentrated, and the crude product is separated and purified by silica gel column chromatography, and then recrystallized with ethyl acetate and ethanol to obtain a red granular solid, which is the R / S-BPDI1-n type liquid crystal compound shown in formula I or the R / S-BPDI2-n type liquid crystal compound shown in formula II.
4. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 3, characterized in that: When preparing R / S-BPDI1-n type liquid crystal compounds, the molar ratio of R / S-B1, PDI-n, Pd(PPh3)4 and CuI is 10:5:1:
2.
5. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 4, characterized in that: In step S1, the reaction is carried out at 85° C. for 24 h under argon protection.
6. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 3, characterized in that: When preparing R / S-BPDI2-n type liquid crystal compounds, the molar ratio of R / S-B2, PDI-n, Pd(PPh3)4 and CuI is 5:10:1:
2.
7. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 6, characterized in that: In step S1, the reaction is carried out at 85° C. for 48 h under argon protection.
8. The method for preparing the chiral binaphthyl-bridged perylene diimide circularly polarized luminescent liquid crystal compound according to claim 4 or 6, characterized in that: Toluene and triethylamine are mixed in a volume ratio of 2:1 to form a mixed solution.