Circularly polarized organic room-temperature phosphorescent material and preparation method and application thereof

Abstract

The invention provides an organic circularly-polarized room-temperature phosphorescent material and application thereof. The chiral phosphorescent material with a D-A structure is formed by taking axial chiral binaphthalene as a chiral donor unit (D) and introducing a proper potential phosphorescent acceptor unit (A) into the chiral donor unit (D). On one hand, binaphthalene serving as a chiral donor unit has large steric hindrance, large torsion of molecules is facilitated to reduce the aggregation quenching effect of the molecules, an intersystem crossing process is activated to realize room-temperature phosphorescence emission, and the radiation efficiency of triplet excitons is improved; on the other hand, a rigid eight-membered ring formed by axial chiral binaphthalene and a phosphorescent unit can enable the chiral organic light-emitting material to have a circularly polarized light-emitting property, and an eight-membered ring lock can ensure the stability of chirality and inhibit a racemization process.

Description

Technical Field

[0001] The invention relates to the field of organic room temperature phosphorescent materials, and in particular to a circularly polarized organic room temperature phosphorescent material and a preparation method and application thereof. Background Art

[0002] Organic circularly polarized room temperature phosphorescent (CPRTP) materials that have both circularly polarized luminescence (CPL) and organic room temperature phosphorescence (RTP) properties have broad application prospects in information encryption, asymmetric synthesis, optical communications, 3D display and other fields. However, most CPL materials are fluorescent materials. Due to the instability of triplet excitons, there are still only a handful of CPRTP materials. Therefore, this new research field is expected to achieve important breakthroughs in organic light-emitting materials and provide more cutting-edge application scenarios.

[0003] In 2016, Professor Hirata of Tokyo Institute of Technology first doped a pair of dinaphthylamine derivatives into a β-estradiol matrix and observed yellow long-lasting chiral phosphorescence at room temperature. The quantum yield and lifetime can reach 2.3% and 0.67s, and the asymmetry factor is 10 -3 In 2018, Duan Pengfei and others finally realized the chiral fluorescence and room temperature phosphorescence of the intermolecular charge transfer state by the method of chiral ion eutectic growth. In the same year, An Zhongfu and others introduced a chiral benzyl alcohol unit on the carbazole triazine unit and realized the ultra-long chiral room temperature phosphorescence emission with a lifetime of 420ms. After that, Zheng Youxuan of Nanjing University coupled carbazole with chiral paracyclophane to construct a chiral enantiomer with a luminescence asymmetry factor of 1.2×10 -2 , the RTP lifetime in the crystal state is about 300ms. Chen Runfeng from Nanjing University of Posts and Telecommunications and Professor Ma Xiang from East China University of Science and Technology have also developed cluster luminescence room temperature phosphorescence and chiral binaphthol room temperature phosphorescent polymer systems, providing a new strategy for the design of circularly polarized room temperature phosphorescent materials.

[0004] However, research on circularly polarized RTP materials is still in its early stages. Although the phosphorescent emission properties will be useful for various display and sensing applications, the performance of the constructed chiral room temperature phosphorescent materials is still poor, making it difficult to achieve further application expansion. Summary of the invention

[0005] In view of the fact that the overall number of circularly polarized room temperature phosphorescent materials in the prior art is still very limited, it is necessary to provide new molecular structures and synthesis routes to expand the molecular library; the reported CPRTP molecules have very poor performance in solution and can only show good chiral room temperature phosphorescent properties in a solid state or in a matrix; the reported CPRTP molecules only show application prospects in the field of information encryption and have a narrow range of application fields. The present invention provides a circularly polarized organic room temperature phosphorescent material.

[0006] The technical solution adopted by the present invention to solve the technical problem is to provide a circularly polarized organic room temperature phosphorescent material, the structural formula (I) is as follows:

[0007]

[0008] Among them, X 1 , X 2 is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, carbonyl, alkyl, and aryl; X 3 is selected from one of oxygen, amine, sulfur, sulfoxide, sulfone, and phosphineoxy; R 1 , R 2 , R 3 , R 4 are independently selected from hydrogen, deuterium, halide, cyano, aryl, nitro, substituted or unsubstituted C 3 -C 60 Aromatic ring group, substituted or unsubstituted C 3 -C 60 One of the aromatic heterocyclic groups; wherein X 1 , X 2 , X 3 , R 1 With R 2 There is no interconnection or covalent bonding between them, R 3 , R 4 Can be used with R 1 and R 2 Covalent or non-covalent bonding.

[0009] The present invention also provides a method for preparing a circularly polarized organic room temperature phosphorescent material, wherein the circularly polarized organic room temperature phosphorescent material is prepared by a chiral binaphthyl unit D and a phosphorescent unit A through a nucleophilic substitution reaction and a Schiff base reaction, wherein the chiral binaphthyl unit D and the phosphorescent unit A have the following structural formulas:

[0010]

[0011] Among them, X 1 , X 2 is independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, carbonyl, alkyl, and aryl; X 3 is selected from one of oxygen, amine, sulfur, sulfoxide, sulfone, and phosphineoxy; R 1 , R 2 , R 3 , R 4 are independently selected from hydrogen, deuterium, halide, cyano, aryl, nitro, substituted or unsubstituted C 3 -C 60 Aromatic ring group, substituted or unsubstituted C 3 -C 60 One of the aromatic heterocyclic groups; wherein X1 , X 2 , X 3 , R 1 With R 2 There is no interconnection or covalent bonding between them, R 3 , R 4 Can be used with R 1 and R 2 Covalent or non-covalent bonding; the position where the asterisk is located is the connection position.

[0012] The present invention also provides a circularly polarized organic room temperature phosphorescent material for use in anti-counterfeiting encryption, chiral recognition, chiral catalysis, circularly polarized light-emitting devices, chiral display, 3D display and bio-imaging.

[0013] The implementation of the present invention can achieve the following beneficial effects:

[0014] The present invention provides a class of molecules of organic circularly polarized room temperature phosphorescent materials, which use binaphthyl as a chiral unit and connect potential phosphorescent molecular units to form CPRTP molecules with an eight-membered heterocyclic structure, and this type of structure has not been reported before; the molecules of the present invention have significant room temperature phosphorescence and circularly polarized luminescence properties, and are not limited by the morphology of the material, and can achieve stable and efficient phosphorescence emission in any form including solution, nano-aggregate state, amorphous film state, powder state and crystal state; the embodiments of the present invention provide such organic circularly polarized phosphorescent materials for application not only in anti-counterfeiting but also in the field of bio-imaging, wherein the anti-counterfeiting film and the nanoparticles for bio-imaging include any of the chiral organic luminescent materials described above, and the compounds of the present invention have a high degree of oxygen sensitivity, so they can be used for hypoxic imaging of cells, tissues and living organisms. BRIEF DESCRIPTION OF THE DRAWINGS

[0015] Figure 1 Compound P 1-1 H-NMR and C-NMR spectra;

[0016] Figure 2 Compound P 1-4 H-NMR and C-NMR spectra;

[0017] Figure 3 Compound P 1-5 H-NMR and C-NMR spectra;

[0018] Figure 4 Compound P 1-1 ,P 1-4 and P 1-5 Fluorescence spectra in different ratios of tetrahydrofuran / water solutions;

[0019] Figure 5 Compound P 1-1 ,P 1-4 and P1-5 Circular dichroism (CD) spectrum and circularly polarized luminescence (CPL) spectrum;

[0020] Figure 6 Compound P 1-1 ,P 1-4 and P 1-5 Photophysical properties: (a) All compounds P 1-1 ,P 1-4 and P 1-5 Normalized emission spectra in toluene solution; (b) all compounds P 1-1 ,P 1-4 and P 1-5 Normalized emission spectrum of compound (S)-P in the crystalline state; (c) 1-5 Photoluminescence spectra of all compounds in tetrahydrofuran / water solutions with different water contents; (d) Compound (S)-P 1-1 At 1wt%P 1-1 Photoluminescence spectra of doped polymethyl methacrylate (PMMA) films under different illumination times; (e) All compounds P 1-1 ,P 1-4 and P 1-5 Fluorescence lifetime in the crystalline state (detection wavelength is 440 nm); (f) phosphorescence lifetime in the crystalline state (at room temperature) (detection wavelength is 440 nm); (g) steady-state spectra of all compounds in the crystalline state and transient spectra after a delay of 1 millisecond;

[0021] Figure 7 Compound P 1-1 and P 1-5 Anti-counterfeiting application; under 298K conditions, 365 nm UV light was used to 1-5 Dimethyl sulfoxide solution (10 -5 M) Luminescence changes during illumination from the bottom, and in the presence of P 1-5 Dimethyl sulfoxide gel and P 1-1 Pattern model for write-erase-rewrite process on PMMA film; Figure 8 Compound P 1-5 Bioimaging applications: (a) Bottom-up synthesis of (S)-P 1-5 and PEG-DSPE water-soluble nanoparticles, and their aqueous solutions were injected into the Hela cell xenograft mouse model; (b, c) (S)-P 1-5 DLS and TEM images of nanoparticles. The scale bar in the TEM image is 100 nm. (d) 1-5HeLa cells were treated under hypoxic conditions for 12 h and confocal imaging was performed after laser irradiation (390 nm, duration for 10 min, interval of 120 s); scale bar: 10 μm; (e) In vivo imaging of HeLa cell xenograft mouse model and biological imaging of various organ tissues under 390 nm irradiation after dissection at different times. DETAILED DESCRIPTION

[0022] In order to have a clearer understanding of the technical features, purposes and effects of the present invention, the specific embodiments of the present invention are now described in detail with reference to the accompanying drawings. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments described in this specification, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0023] The organic room temperature phosphorescent material of the present invention is characterized in that its structure is as shown in formula (I);

[0024]

[0025] In formula (I), X in the chiral unit (D) is 1 , X 2 is independently selected from hydrogen, deuterium, halide, cyano, nitro, carbonyl, alkyl, aryl; X 3 Selected from oxygen, amine, sulfur, sulfoxide, sulfone, phosphineoxy;

[0026] In formula (I), R of the phosphorescent unit (A) is 1 , R 2 , R 3 , R 4 are independently selected from hydrogen, deuterium, halide, cyano, aryl, nitro, substituted or unsubstituted C 3 -C 60 Aromatic ring group, substituted or unsubstituted C 3 -C 60 Aromatic heterocyclic group.

[0027] Among them, X 1 , X 2 , X 3 , R 1 With R 2 There is no interconnection or covalent bonding between them, R 3 , R 4 Can be used with R 1 and R 2 Covalent or non-covalent bonding.

[0028] In this experimental example, binaphthyl is used as the chiral donor unit (D), and a charge transfer chiral phosphorescent material with a DA structure is formed by introducing a suitable phosphorescent acceptor unit (A) therein; on the one hand, the chiral binaphthyl as an electron donor has a large steric hindrance, which is conducive to the formation of a large torsion between DA, thereby reducing the concentration quenching effect (ACQ) under the molecular aggregation state; on the other hand, the rigid eight-membered ring structure formed by the chiral binaphthyl and the phosphorescent unit makes the chiral luminescent material have circularly polarized luminescence characteristics, and can stabilize the triplet excitons, providing a favorable guarantee for achieving efficient phosphorescent emission.

[0029] Specifically, in this embodiment, X 1 The connection bit is X 1 Any substitution position of the benzene ring, X 2 The connection bit is X 2 The chiral organic phosphorescent material comprises an R-type isomer and / or an S-type isomer in chiral absolute configuration: wherein the structural formula of the R-type isomer is as follows: As shown, the structural formula of the S-isomer is as follows: As shown; in formula RI, SI, the X of the chiral unit (D) 1 , X 2 is independently selected from hydrogen, deuterium, halide, cyano, nitro, carbonyl, alkyl, aryl; X 3 R in the phosphorescent unit (A) is selected from oxygen, amine, sulfur, sulfoxide, sulfone, and phosphino group; 1 , R 2 , R 3 , R 4 are independently selected from hydrogen, deuterium, halide, cyano, aryl, nitro, substituted or unsubstituted C 3 -C 60 Aromatic ring group, substituted or unsubstituted C 3 -C 60 wherein X 1 , X 2 , X 3 , R 1 With R 2 There is no interconnection or covalent bonding between them, R 3 , R 4 Can be used with R 1 and R 2 Covalent or non-covalent bonding. The organic circularly polarized room temperature phosphorescent material is prepared by using existing or substituted axial chiral binaphthyl and phosphorescent units through nucleophilic substitution reaction and Schiff base reaction.

[0030] In one embodiment, X of the left chiral unit D 1 , X 2 , X 3 The group can be selected from but not limited to

[0031]

[0032] The position where the asterisk is located is the connection position with the phosphorescent unit A. Preferably, D can be selected from

[0033] In one embodiment, R of the right phosphorescent unit A 3 or R 4 The group can be selected from but not limited to

[0034]

[0035]

[0036]

[0037] The position where the asterisk is located is the connection position with the left chiral unit A. Preferably, A can be selected from

[0038]

[0039] Within the above range, the organic circularly polarized room temperature phosphorescent material with a DA structure formed by A and chiral binaphthyl, in which D and A are connected by a geodesic twisted octagonal ring structure, is conducive to the formation of an intramolecular charge transfer state, so that the formed DA-type organic phosphorescent material has a more efficient intersystem crossing process and phosphorescent radiation properties.

[0040] In one embodiment, the organic room temperature phosphorescent target molecule P n-n (i.e. D n With A n The combination of) may be but is not limited to

[0041]

[0042]

[0043]

[0044]

[0045] That is, X1-X3 are all H; of course, the compound P shown in the above structure 1-1 -P 1-84 The chiral organic phosphorescent material may include isomers whose chiral absolute configuration is S type and / or R type. Preferably, the chiral organic phosphorescent material is:

[0046] The chiral organic phosphorescent materials within the above range have typical intramolecular charge transfer properties, distorted eight-membered ring configurations and obvious room temperature phosphorescence properties.

[0047] The present invention will be further described below by means of specific examples.

[0048] Example 1 Compound P 1-1 ,P 1-4 ,P 1-5 Preparation

[0049]

[0050] According to reaction formula (1), under nitrogen protection, A 1 (203.1 mg, 1.2 mmol) (or A 4 (389.3 mg, 1.2 mmol) or A 5 (500.0mg, 1.2mmol)), BINOL (405.3mg, 1.4mmol), potassium carbonate (489.0mg, 3.5mmol) were added to a 25ml round-bottom flask, dissolved with DMF (8mL), and then stirred at room temperature for 24 hours. After the reaction was completed, saturated brine was added to precipitate, filtered and dried. Purified by column chromatography, the target product P was obtained by column chromatography with a volume ratio of petroleum ether: dichloromethane of 3:1. 1-1 (400.0mg)P 1-4 (580.0mg)P 1-5 (690.0 mg). The yields were 81.0%, 85.3%, and 87.3%, respectively. Figure 1 , as shown in 2 and 3.

[0051] Example 2 Compound P 1-23 Preparation

[0052]

[0053] According to reaction formula (1), under nitrogen protection, DFTC-SO (500.0 mg, 2.2 mmol), BINOL (740.0 mg, 2.6 mmol), potassium carbonate (892.8 mg, 6.5 mmol) were added to a 25 ml round-bottom flask, dissolved with DMF (8 mL), and then stirred at room temperature for 24 hours. After the reaction was completed, saturated brine was added to precipitate, filtered and dried. Purified by column chromatography, the target product P was obtained by column chromatography with a volume ratio of petroleum ether: dichloromethane of 3:1. 1-23 (870.0 mg). Yield: 84.4%.

[0054] Example 3 Compound P 1-28 Preparation

[0055]

[0056] According to reaction formula (1), under nitrogen protection, A 28 (500.0 mg, 1.5 mmol), BINOL (499.3 mg, 1.7 mmol), potassium carbonate (602.5 mg, 4.4 mmol) were added to a 25 ml round-bottom flask, dissolved with DMF (8 mL), and then stirred at room temperature for 24 hours. After the reaction was completed, saturated brine was added to precipitate, filtered and dried. Purified by column chromatography, the target product P was obtained by column chromatography with a volume ratio of petroleum ether: dichloromethane of 3:1. 1-28 (520.0 mg). Yield: 74.8%.

[0057] Example 4 Compound P 1-44 Preparation

[0058]

[0059] According to reaction formula (1), under nitrogen protection, A 44 (500.0 mg, 1.3 mmol), BINOL (451.9 mg, 1.6 mmol), potassium carbonate (545.3 mg, 4.0 mmol) were added to a 25 ml round-bottom flask, dissolved with DMF (8 mL), and then stirred at room temperature for 24 hours. After the reaction was completed, saturated brine was added to precipitate, filtered and dried. Purified by column chromatography, the target product P was obtained by column chromatography with a volume ratio of petroleum ether: dichloromethane of 3:1. 1-44 (550.0 mg). Yield: 66.8%.

[0060] The preparation methods of other derivatives involved in the present invention are similar to the methods of the corresponding embodiments above, except that the types of the connected chiral unit D and phosphorescent unit A are different, and all of them can be prepared by nucleophilic substitution reaction.

[0061] Example 1 Compound P 1-1 ,P 1-4 and P 1-5 AIE property test

[0062] For compound P 1-1 ,P 1-4 and P 1-5 Photophysical tests were carried out in water / THF solutions with different volume ratios. The test results are as follows Figure 4 It can be seen that compound P 1-1 ,P 1-4 and P 1-5 With the increase of water ratio, P 1-1 The fluorescence intensity of P 1-4 and P1-5 The phosphorescence peak at 650nm also gradually increases. This is because the aggregation not only restricts the molecular motion, but also isolates the erosion of oxygen, thereby inhibiting the non-radiative transition pathway of the molecules.

[0063] Example 1 Compound P 1-1 ,P 1-4 and P 1-5 Circular dichroism and circular polarization luminescence properties test

[0064] Since the binaphthol unit in the organic chiral phosphorescent material has axial chirality, the compound P 1-1 ,P 1-4 and P 1-5 Carry out circular dichroism and circular polarization luminescence spectrum tests, such as Figure 5 As shown. It can be seen that there are three pairs of enantiomers: (R)-P 1-1 and (S)-P 1-1 , (R)-P 1-4 and (S)-P 1-4 , (R)-P 1-5 and (S)-P 1-5 All exhibit selective absorption and emission of left-handed or right-handed circularly polarized light, and the (R) / (S)-isomers have obvious positive / negative Cotton effects, respectively, which indicates that a variety of circularly polarized phosphorescent materials can be obtained by connecting binaphthol to different phosphorescent units.

[0065] Example 1 Compound P 1-1 ,P 1-4 and P 1-5 Room temperature phosphorescence properties test

[0066] Due to the participation of heteroatom n-π orbitals and the influence of heavy atom effects, compound P 1-1 ,P 1-4 and P 1-5 The luminescence properties of these materials were studied by using steady-state and delayed luminescence spectra. Figure 6 As shown in FIG. 1 , the delayed luminescence spectrum represented by the red curve proves that its low-energy emission peaks are all phosphorescence peaks (delay time is 1 ms). Accordingly, the time-resolved lifetime test shows that compound P 1-1 ,P 1-4 and P 1-5 It has a nanosecond fluorescence lifetime and a microsecond red phosphorescence lifetime. 1-1 ,P 1-4 and P 1-5 Not only in the crystal state ( Figure 6 d) exhibit room temperature phosphorescence in solution ( Figure 6e) and the process of forming nanoaggregates, it can also show obvious phosphorescence emission in solution. It is also important to note that in 1wt% PMMA film, compound P 1-1 It can also show significant light-activated phosphorescence enhancement phenomenon. As the ultraviolet light exposure time increases, the color of the film can gradually change from blue to red. This phenomenon can also be applied to subsequent anti-counterfeiting encryption fields.

[0067] Example 1 Compound P 1-5 and P 1-1 Anti-counterfeiting applications

[0068] like Figure 7 As shown, myristic acid amide, which is transparent in the ultraviolet region, was selected as a gelling agent, and DMSO was made into an opaque white gel and pasted on a glass dish. The gel sample was prepared in air, and the gelling agent and compound P 1-5 The concentrations were 4wt% and 10 -5 M. After irradiating the perforated mask pattern of cat's paw at a distance of zero for about 1 minute using a 365nm UV lamp, a bright red cat's paw pattern can be seen using the same 365nm UV lamp but at a distance greater than 20 cm. This luminescent pattern can stay in the gel for several hours, but is quickly eliminated by heating the gel into a liquid and then cooling and resolidifying it, and its light-activated emission spectrum is the same as the spectrum recorded by the fluid DMSO solution. The second anti-counterfeiting pattern is to dope compound P1 in a PMMA film at 1wt%, use the same 365nm UV lamp to irradiate the perforated mask pattern of lotus at a distance of zero for about 1 minute, then remove the mask pattern and irradiate it with the UV lamp at a distance, and an obvious red phosphorescence enhancement phenomenon can be seen, and the unirradiated area is still blue fluorescence. After standing in the air for 2 hours, it can be found that the PMMA film can be restored to its original pattern-free state. The circularly polarized room temperature phosphorescent material of the present invention shows the dual functions of color change and time change.

[0069] Example 1 Compound P 1-5 Bio-imaging applications

[0070] P 1-5 Applied to hypoxia imaging of living cells. HeLa cells were cultured and loaded with P 1-5 , and confocal imaging was performed under atmospheres with different oxygen contents. Figure 8 As shown in a, under normoxic conditions, HeLa cells can hardly observe phosphorescence emission at 552-652nm. However, when cultured in an oxygen-deficient incubator, the phosphorescence is significantly enhanced. In addition, as the irradiation time of the 390nm light source increases, the phosphorescence intensity gradually increases. Therefore, the oxygen sensitivity of this type of chiral organic phosphorescent material can provide a potential platform for cell hypoxia imaging.

[0071] Then, we explored in vivo hypoxia imaging and injected P 1-5 After the phosphorescent nanoparticles were injected, hypoxic phosphorescence imaging of the tumor site was observed in the bio-imaging mode. The tumor and other organs were then collected by dissection and immediately imaged under 390 nm excitation. Figure 8 The results of b show that under the imaging conditions, other organs are darker in color, but the tumor exhibits stronger phosphorescence due to the hypoxic environment. In addition, the intensity of phosphorescence indicates the uneven distribution of oxygen content in the tumor. The stronger phosphorescence in the center of the tumor indicates that the center of the tumor is more hypoxic than the surface of the tumor. These results show that P 1-5 It can perform hypoxic imaging of tumors.

[0072] In summary, the organic circularly polarized room temperature phosphorescent material and its application provided by the present invention, the present invention uses axial chiral binaphthyl as a chiral donor unit (D), and introduces a suitable potential phosphorescent receptor unit (A) therein to form a chiral phosphorescent material with a DA structure. On the one hand, binaphthyl as a chiral donor unit has a large steric hindrance, which is conducive to the formation of a large twist of the molecule to reduce the aggregation quenching effect of the molecule, activate the intersystem crossing process to achieve room temperature phosphorescent emission, and improve the radiation efficiency of triplet excitons; on the other hand, the rigid eight-membered ring formed by the axial chiral binaphthyl and the phosphorescent unit can make the chiral organic light-emitting material have circularly polarized light-emitting properties, and the eight-membered ring lock can ensure the stability of the chirality and inhibit the racemization process.

[0073] The embodiments of the present invention are described above in conjunction with the accompanying drawings, but the present invention is not limited to the above-mentioned specific embodiments. The above-mentioned specific embodiments are merely illustrative and not restrictive. Under the guidance of the present invention, ordinary technicians in this field can make many modifications without departing from the scope of protection of the present invention and the claims, all of which belong to the scope of protection of the present invention.

Claims

1. A circularly polarized organic room temperature phosphorescent material, characterized in that: The structural formula (I) of the circularly polarized organic room temperature phosphorescent material is as follows: wherein X1 and X2 are independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, carbonyl, alkyl, and aryl; X3 is selected from one of oxygen, amine, sulfur, sulfoxide, sulfone, and phosphino; R1, R2, R3, and R4 are independently selected from one of hydrogen, deuterium, halogen, cyano, aryl, nitro, substituted or unsubstituted C3-C 60 Aromatic ring group, substituted or unsubstituted C3-C 60 wherein X1, X2, X3, R1 and R2 are not interconnected or covalently bonded, and R3 and R4 may be covalently or non-covalently bonded to R1 and R2.

2. The circularly polarized organic room temperature phosphorescent material according to claim 1, characterized in that: The circularly polarized organic room temperature phosphorescent material includes isomers with chiral absolute configurations of R type and / or S type, wherein the structural formula of the R type isomer (RI) and the structural formula of the S type isomer (SI) are respectively as follows:

3. The circularly polarized organic room temperature phosphorescent material according to claim 1, characterized in that: The circularly polarized organic room temperature phosphorescent material has the structural formula shown below:

4. A method for preparing a circularly polarized organic room temperature phosphorescent material as claimed in any one of claims 1 to 3, characterized in that: The circularly polarized organic room temperature phosphorescent material is prepared by a chiral binaphthyl unit D and a phosphorescent unit A through a nucleophilic substitution reaction and a Schiff base reaction, wherein the chiral binaphthyl unit D and the phosphorescent unit A have the following structural formulas: wherein X1 and X2 are independently selected from one of hydrogen, deuterium, halogen, cyano, nitro, carbonyl, alkyl, and aryl; X3 is selected from one of oxygen, amine, sulfur, sulfoxide, sulfone, and phosphino; R1, R2, R3, and R4 are independently selected from one of hydrogen, deuterium, halogen, cyano, aryl, nitro, substituted or unsubstituted C3-C 60 Aromatic ring group, substituted or unsubstituted C3-C 60 One of the aromatic heterocyclic groups; wherein X1, X2, X3, R1 and R2 are not interconnected or covalently bonded, R3 and R4 can be covalently or non-covalently bonded to R1 and R2; the position where the asterisk is located is the connection position.

5. The preparation method according to claim 4, characterized in that: D can be selected from one of the following structural formulas:

6. The preparation method according to claim 4, characterized in that: A can be selected from one of the following structural formulas:

7. Use of the circularly polarized organic room temperature phosphorescent material as described in any one of claims 1 to 3 in anti-counterfeiting encryption.

8. Use of the circularly polarized organic room temperature phosphorescent material according to any one of claims 1 to 3 in biological imaging.

9. Use of the circularly polarized organic room temperature phosphorescent material according to any one of claims 1 to 3 in chiral recognition, chiral catalysis, chiral display and 3D display.

10. Use of the circularly polarized organic room temperature phosphorescent material according to any one of claims 1 to 3 in a circularly polarized light-emitting device.

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