Surface chirality [2.2] cyclosimulation organic small molecule with high solid-state luminescence property, preparation method and application of surface chirality [2.2] cyclosimulation organic small molecule

Abstract

The invention provides a planar chiral [2.2] cyclosimulation organic small molecule with high solid-state luminescence performance, a preparation method and application, and relates to the field of organic luminescent materials. The invention provides a planar chiral [2.2] cyclosimulation organic small molecule with high solid-state luminescence performance. The molecular structural formula of the planar chiral [2.2] cyclosimulation organic small molecule is as follows: # imgabs0 #, according to the planar chiral [2.2] cyclosimulation organic small molecule with the high solid-state luminescence property, an electron donating group diphenyl amino and an electron withdrawing group [(2-dimeryl boryl) phenyl] ethynyl are respectively introduced into pseudo meta-positions of two benzene rings of [2.2] cyclosimulation, so that the planar chiral [2.2] cyclosimulation organic small molecule has high solid-state fluorescence quantum yield and high solid-state luminescence asymmetric factors, and the planar chiral [2.2] cyclosimulation organic small molecule has the advantages of high solid-state fluorescence quantum yield and high solid-state luminescence asymmetric factors. The material shows excellent circular polarization luminescence characteristics.

Description

Technical Field

[0001] The present invention relates to the field of organic luminescent materials, and in particular to a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescent performance, a preparation method and application thereof. Background Art

[0002] Polarization is one of the important properties inherent in light. According to the different endpoint trajectories of the light vector, polarized light is mainly divided into linear polarized light, circular polarized light and elliptically polarized light. Among them, circular polarized light is closer to natural light, which can effectively reduce people's visual fatigue and achieve the purpose of healthy eye protection.

[0003] Circularly polarized luminescence (CPL) refers to the phenomenon that a chiral luminescent system or an achiral luminescent system emits differentially left-handed or right-handed circularly polarized light in a chiral environment. This type of material has potential application prospects in the fields of three-dimensional display, optical information storage and processing, biological probes, CPL sensors, asymmetric photochemical synthesis, etc. At present, the most studied CPL materials are transition metal complexes, organic polymers, and organic small molecules; in contrast, organic small molecules have the advantages of easy derivatization, adjustable emission wavelength, simple preparation process, and easy structure determination. Therefore, the research on organic small molecule CPL materials has become an important topic at present. Fluorescence quantum yield (Φ F ) and the luminescence asymmetry factor (g lum ) are two important parameters for measuring the luminescence performance of circularly polarized luminescent materials; at the same time, since the prepared devices are often in a solid state, high solid-state luminescence performance is a very important reference indicator for circularly polarized luminescent materials.

[0004] Due to the aggregation-induced quenching phenomenon caused by intermolecular interactions, the fluorescence quantum yield of organic small molecules in the solid state is generally low; and the luminescence asymmetry factor of the currently disclosed CPL organic small molecules is also generally low (less than 5×10 -3 ). Especially in the solid state, the improvement of the fluorescence quantum yield and luminescence asymmetry factor of CPL organic small molecules is further restricted. Therefore, it is very challenging to obtain organic small molecules with both high fluorescence quantum yield and high luminescence asymmetry factor.

[0005] "Study on Boron-modified [2.2] Cyclomorph Organic Luminescent Materials" (Shandong University doctoral dissertation, Zhang Mengyuan et al.) discloses a pseudo-meta-substituted [2.2] cyclomorph derivative m-BPhNPh2-Cp, the fluorescence quantum yield of which is 0.19 in powder state. Although the luminescence asymmetry factor of the molecule is relatively high in solution, its luminescence asymmetry factor in solid state cannot be detected, and its fluorescence quantum yield is also low. Based on the current research progress, providing a CPL organic small molecule with high solid-state luminescence performance, especially a CPL organic small molecule with both high fluorescence quantum yield and high luminescence asymmetry factor in solid state, has important technical significance and broad application prospects. Summary of the invention

[0006] In order to solve the technical problems existing in the prior art, the present invention provides a planar chiral [2.2] cyclosim organic small molecule with high solid-state luminescence performance, which can simultaneously have a high fluorescence quantum yield and a high luminescence asymmetry factor in a solid state; the present invention also provides a preparation method of the planar chiral [2.2] cyclosim organic small molecule; the present invention also provides the application of the planar chiral [2.2] cyclosim organic small molecule.

[0007] In order to solve the above technical problems, the technical solution adopted by the present invention is as follows: A planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance, the molecular structure is shown below: ; In the formula, -BMes2 is diphenylboryl and -NPh2 is diphenylamino.

[0008] A method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance comprises the following steps: With 4-iodo-15-diphenylamino[2.2]cyclomorph as the starting material, a coupling reaction is first carried out to obtain 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph; and then a borylation reaction is carried out to obtain a planar chiral[2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

[0009] Furthermore, the coupling reaction method is that in a solvent environment, in the presence of cuprous iodide and bistriphenylphosphine palladium dichloride, 4-iodo-15-diphenylamino[2.2]cycloform reacts with 2-bromophenylacetylene to obtain 4-(2-bromophenylacetylene)-15-diphenylamino[2.2]cycloform; The borylation reaction method is that, in a solvent environment, 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph is first contacted with n-butyl lithium for reaction, and then contacted with diphenylboron fluoride for reaction, so as to obtain a planar chiral [2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

[0010] Preferably, in the coupling reaction, the molar ratio of 4-iodo-15-diphenylamino[2.2]cyclomorph, 2-bromophenylacetylene, bistriphenylphosphine palladium dichloride, and cuprous iodide is 1:1-1.3:0.05-0.1:0.06-0.09.

[0011] Preferably, in the coupling reaction, the reaction time of 4-iodo-15-diphenylamino[2.2]cyclopentane and 2-bromophenylacetylene is 12-18 hours.

[0012] Preferably, in the borylation reaction, the molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclopentane to n-butyllithium is 1:1.8-2.2; The molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorpha to diphenylborane is 1:2-3.

[0013] Preferably, in the borylation reaction, the reaction time of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclopentane and n-butyllithium is 1.5-2 h.

[0014] Preferably, in the borylation reaction, the contact reaction time with dimethylborofluoride is 10-15 hours.

[0015] The synthesis route of the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance is: .

[0016] A use of the aforementioned planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the aforementioned preparation method as a circularly polarized luminescent material.

[0017] Application of the aforementioned planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the aforementioned preparation method in the fields of three-dimensional display, optical information storage and processing, biological probes, and CPL sensors.

[0018] Compared with the prior art, the present invention has the following beneficial effects: (1) The planar chiral [2.2] cyclomorph organic small molecule m-BPhANPh2-Cp with solid-state luminescence performance of the present invention uses [2.2] cyclomorph as a structural unit, and introduces an electron-donating group diphenylamino and an electron-withdrawing group [(2-diphenylboryl)phenyl]ethynyl at the pseudo-meta position of the two benzene rings of [2.2] cyclomorph, respectively; the fluorescence of the planar chiral [2.2] cyclomorph organic small molecule is generated by the intramolecular spatial charge transfer between the electron-donating group diphenylamino and the electron-withdrawing group [(2-diphenylboryl)phenyl]ethynyl; in the planar chiral [2.2] cyclomorph organic small molecule, the [2.2] cyclomorph structural unit has stable planar chirality, and the diphenylboryl group with large steric hindrance can effectively inhibit the aggregation-induced quenching phenomenon caused by intermolecular interactions, and can have a high fluorescence quantum yield and luminescence asymmetry factor in the solid state.

[0019] (2) Compared with the [2.2] cyclosim derivative m-BPhNPh2-Cp disclosed in the prior art, the planar chiral [2.2] cyclosim organic small molecule m-BPhANPh2-Cp with solid-state luminescence performance of the present invention has a strong solid-state circularly polarized luminescence signal, and a higher solid-state fluorescence quantum yield and luminescence asymmetry factor.

[0020] (3) The preparation method of the planar chiral [2.2] cyclosimulated organic small molecule m-BPhANPh2-Cp with solid-state luminescence performance of the present invention is simple, the preparation process is easy to control, the reaction yield is high, and it is conducive to large-scale production.

[0021] (4) The planar chiral [2.2] cyclosimulated organic small molecule m-BPhANPh2-Cp with solid-state luminescence performance of the present invention can be used as a circularly polarized luminescent material in the fields of three-dimensional display, optical information storage and processing, biological probes, CPL sensors, etc., and has broad application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 This is the synthesis route of m-BPhANPh2-Cp in Example 1.

[0023] Figure 2 This is the high-resolution mass spectrum of m-BrPhANPh2-Cp prepared in Example 1.

[0024] Figure 3 This is the hydrogen nuclear magnetic resonance spectrum of m-BrPhANPh2-Cp prepared in Example 1.

[0025] Figure 4 This is the high-resolution mass spectrum of m-BPhANPh2-Cp prepared in Example 1.

[0026] Figure 5 This is the hydrogen nuclear magnetic resonance spectrum of m-BPhANPh2-Cp prepared in Example 1.

[0027] Figure 6 This is the fluorescence emission spectrum of the m-BPhANPh2-Cp powder and film prepared in Example 1.

[0028] Figure 7 This is the HPLC chromatogram of m-BPhANPh2-Cp prepared in Example 1.

[0029] Figure 8 This is the circularly polarized luminescence spectrum of the m-BPhANPh2-Cp film prepared in Example 1. DETAILED DESCRIPTION

[0030] 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. It should be noted that the following detailed descriptions are exemplary and are intended to provide further explanation of the present invention. Unless otherwise specified, all technical and scientific terms used in the present invention have the same meanings as those commonly understood by those of ordinary skill in the art to which the present invention belongs.

[0031] It should be noted that the terms used herein are only for describing specific embodiments and are not intended to limit exemplary embodiments according to the present invention. As used herein, "first", "second", etc. are used to distinguish similar objects, and are not used to describe a specific order or sequence. In addition, it should be understood that when the terms "comprising" and / or "including" are used in this specification, it indicates the presence of features, steps, operations, devices, components and / or combinations thereof.

[0032] The embodiment of the present invention provides a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance. The planar chiral [2.2] cyclosimulated organic small molecule is named m-BPhANPh2-Cp and has the following molecular structure: ; In the formula, -BMes2 is diphenylboryl and -NPh2 is diphenylamino.

[0033] The present invention also provides a method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance, comprising: Using 4-iodo-15-diphenylamino[2.2]cyclomorph as the starting material, a Sonogashira coupling reaction is first carried out to obtain 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph, and then a borylation reaction is carried out to obtain a planar chiral[2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

[0034] Furthermore, the method of the Sonogashira coupling reaction is that in a solvent environment, in the presence of cuprous iodide and bistriphenylphosphine palladium dichloride, 4-iodo-15-diphenylamino[2.2]cyclomorph reacts with 2-bromophenylacetylene to obtain 4-(2-bromophenylacetylene)-15-diphenylamino[2.2]cyclomorph; The borylation reaction method is that, in a solvent environment, 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph is first contacted with n-butyl lithium for reaction, and then contacted with diphenylboron fluoride for reaction, so as to obtain a planar chiral [2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

[0035] Furthermore, the method of the Sonogashira coupling reaction is that, in a solvent environment, in the presence of cuprous iodide and bistriphenylphosphine palladium dichloride, 4-iodo-15-diphenylamino[2.2]cycloform and 2-bromophenylacetylene are reacted at room temperature, extracted with an extractant, and the extract phase is dried, desolventized and purified to obtain 4-(2-bromophenylacetylene)-15-diphenylamino[2.2]cycloform.

[0036] The borylation reaction method is that in a solvent environment, 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph is first reacted with n-butyl lithium at low temperature, then reacted with diphenylborane at room temperature, extracted with an extractant, and the extract phase is dried, desolventized and purified to obtain a planar chiral [2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

[0037] Preferably, in the Sonogashira coupling, the molar ratio of 4-iodo-15-diphenylamino[2.2]cyclomorph, 2-bromophenylacetylene, bistriphenylphosphine palladium dichloride, and cuprous iodide is 1:1-1.3:0.05-0.1:0.06-0.09 Preferably, in the Sonogashira coupling, the reaction time is 12-18 h; for example, the reaction time can be 12 h, 14 h, 16 h or 18 h.

[0038] Preferably, in the borylation reaction, the molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclophane to n-butyllithium is 1:1.8-2.2.

[0039] Preferably, in the borylation reaction, the reaction time of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclophane and n-butyllithium is 1.5-2 h; for example, the reaction time can be 1.5 h, 1.7 h or 2 h.

[0040] Preferably, in the borylation reaction, the molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorpha to diphenylborane is 1:2-3; for example, the molar ratio may be 1:2, 1:2.5 or 1:3.

[0041] Preferably, in the borylation reaction, the reaction time of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclopentane and diphenylborane is 10-15 h; for example, the reaction time can be 10 h, 12 h, 13 h or 15 h.

[0042] The present invention also provides the use of the aforementioned planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the aforementioned preparation method as a circularly polarized luminescent material.

[0043] The present invention also provides the application of the aforementioned planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the aforementioned preparation method in the fields of three-dimensional display, optical information storage and processing, biological probes, and CPL sensors.

[0044] The present invention is further described below in conjunction with some specific embodiments.

[0045] Example 1 This embodiment provides a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance. The organic small molecule is named m-BPhANPh2-Cp and has the following molecular structure: ; In the formula, -BMes2 is diphenylboryl and -NPh2 is diphenylamino.

[0046] The present invention also provides a method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance. The specific synthesis route is as follows: Figure 1 As shown, the specific steps are as follows: 1. Coupling reaction Sonogashira coupling reaction to prepare 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclophane (m-BrPhANPh2-Cp): 4-iodo-15-diphenylamino[2.2]cyclobutane (m-INPh2-Cp) (413 mg, 0.824 mmol), 2-bromophenylacetylene (178 mg, 0.989 mmol), cuprous iodide (11 mg, 7% mmol), bistriphenylphosphine palladium dichloride (28.8 mg, 5% mmol) were added to a sealed tube, and diethylamine (12 mL) was used as the solvent. The mixture was replaced with nitrogen and reacted at room temperature in a nitrogen atmosphere for 12 h. After the reaction was completed, the mixture was quenched with a saturated sodium chloride solution and extracted with ethyl acetate. After separation, the extract was dried over anhydrous sodium sulfate, filtered to remove the sodium sulfate, and the solvent was removed by reduced pressure distillation using a rotary evaporator. The mixture was separated and purified by silica gel column chromatography (petroleum ether: dichloromethane = 30:1, R f =0.60); a yellow solid was obtained, namely 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclopentane (m-BrPhANPh2-Cp) (228 mg, 0.44 mmol, yield 63%), melting point Mp: 132.5–133.2°C; 1 H NMR (400MHz, CDCl3): δ7.64(dd,J=8.1,1.0Hz,1H),7.57(dd,J=7.7,1.6Hz,1H),7.35–7. 28(m,5H),7.21–7.15(m,5H),7.11(t,J=7.3Hz,2H),7.03(d,J=7.9Hz,1H),6.94(d,J=7. 7Hz,1H),6.85(d,J=1.7Hz,1H),6.34(dd,J=7.9,1.8Hz,1H),6.23(dd,J=7.7,1.6Hz,1H) ,5.81(d,J=1.6Hz,1H),3.65–3.48(m,1H),3.06–2.66(m,7H); HRMS (ESI): 554.1478[M+H] + , C 36 H 29 BrN measured value: 554.1477. The starting material 4-iodo-15-diphenylamino[2.2]cyclomorph (m-INPh2-Cp) used in this example is an existing compound, and the preparation method is referred to "Study on Boron-modified [2.2]cyclomorph organic luminescent materials" (Shandong University doctoral dissertation, Zhang Mengyuan et al.), P63-65.

[0047] The high-resolution mass spectrum of the 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph (m-BrPhANPh2-Cp) prepared above is as follows: Figure 2 As shown, the H NMR spectrum is Figure 3 shown.

[0048] 2. Boration reaction Preparation of 4-[(2-diphenylboryl)phenyl]ethynyl-15-diphenylamino[2.2]cyclophane (m-BPhANPh2-Cp) by borylation reaction: The m-BrPhANPh2-Cp (228 mg, 0.411 mmol) prepared above was dissolved in anhydrous tetrahydrofuran (THF), replaced with nitrogen, and in a nitrogen atmosphere, a n-hexane solution of n-butyl lithium (0.33 mL, 2.5 mol / L, 0.82 mmol) was added dropwise through a syringe at -78°C. After the addition was completed for 10 minutes, the mixture was kept at -78°C for 1.5 hours, and a solution of dimethylborofluoride (275 mg, 1.03 mmol) in anhydrous THF (5 mL) was added through a syringe. The mixture was naturally warmed to room temperature after addition, and reacted at room temperature for 12 hours. After the reaction was completed, the mixture was quenched with a saturated sodium chloride solution and extracted with ethyl acetate. After separation, the extract was dried with anhydrous sodium sulfate, and the sodium sulfate was removed by filtration. The solvent was removed by reduced pressure distillation using a rotary evaporator. The product was separated and purified by silica gel column chromatography (petroleum ether: dichloromethane = 5:1, R f =0.45); obtain the yellow solid target molecule, namely 4-[(2-diphenylboryl)phenyl]ethynyl-15-diphenylamino[2.2]cyclopentane (m-BPhANPh2-Cp) (235 mg, 0.325 mmol, yield 79%), melting point Mp: 134.7-135.2°C; 1 H NMR (400MHz, CDCl3): δ7.57(d,J=7.6Hz,1H),7.39(td,J=8.0,2.4Hz,1H),7.31(s,1H),7.29–7.25( m,5H),7.14(d,J=7.5Hz,4H),7.09(t,J=7.3Hz,2H),6.89(d,J=7.9Hz,1H),6.82(s,4H),6.58(d,J=7 .6Hz,1H),6.22(dd,J=7.9,1.6Hz,1H),5.98(d,J=1.4Hz,1H),5.91(d,J=7.4Hz,1H),5.75(d,J=1.5H z,1H),3.38–3.29(m,1H),2.99–2.58(m,7H),2.32(s,6H),2.05(s,12H); HRMS (ESI): 724.4109[M+H] + , C 54 H 51 BN measured value: 724.4104.

[0049] The high-resolution mass spectrum of 4-[(2-diphenylboryl)phenyl]ethynyl-15-diphenylamino[2.2]cyclophane (m-BPhANPh2-Cp) prepared in this example is as follows: Figure 4 As shown, the H NMR spectrum is Figure 5 shown.

[0050] Example 2 Determination of relevant properties of 4-[(2-dimethylboryl)phenyl]ethynyl-15-diphenylamino[2.2]cyclomorph (m-BPhANPh2-Cp) in powder / film state: It was determined that the fluorescence emission wavelength of m-BPhANPh2-Cp (prepared according to Example 1) in the powder state was 473 nm, and the fluorescence quantum yield was as high as 0.64. The fluorescence emission wavelength and fluorescence quantum yield of m-BPhANPh2-Cp (prepared according to Example 1) in the film state were basically consistent with those in the powder state, and the fluorescence emission wavelength was 465 nm (e.g. Figure 6 As shown in Figure 3 ), the fluorescence quantum yield is also as high as 0.64. Since the aggregation-induced quenching phenomenon is common in organic small molecules, the m-BPhANPh2-Cp of the present invention has a higher fluorescence quantum yield in the solid state in organic small molecules.

[0051] Example 3 Solid-state circularly polarized luminescence properties of 4-[(2-dimethylboryl)phenyl]ethynyl-15-diphenylamino[2.2]cyclophane (m-BPhANPh2-Cp) in thin film state: In view of the fact that the target molecule m-BPhANPh2-Cp of the present invention (prepared according to Example 1) has a high fluorescence quantum yield, the target molecule m-BPhANPh2-Cp was split (such as Figure 7 As shown, Figure 7 The upper middle picture is the HPLC chromatogram of racemic m-BPhANPh2-Cp, and the middle picture is the HPLC chromatogram of R p HPLC chromatogram of the m-BPhANPh2-Cp with the following configuration: p The HPLC chromatogram of the target molecule m-BPhANPh2-Cp in the thin film state was tested (such as Figure 8 As shown in Figure 2, the Sp-configured m-BPhANPh2-Cp in the film state has a positive signal peak at 475 nm (maximum fluorescence emission wavelength), and its luminescence asymmetry factor is +5.4×10 -3 In the thin film state, the Rp-configured m-BPhANPh2-Cp has a negative signal peak at 469nm (maximum fluorescence emission wavelength), and its luminescence asymmetry factor is -4.3×10 -3Therefore, the m-BPhANPh2-Cp of the present invention has excellent solid-state circularly polarized luminescence performance.

[0052] Therefore, the planar chiral [2.2] cyclosimulated organic small molecule m-BPhANPh2-Cp with high solid-state luminescence performance of the present invention has important value in the field of organic small molecule circularly polarized luminescent materials, and has broad application prospects in the fields of three-dimensional display, optical information storage and processing, biological probes, CPL sensors, etc.

[0053] Unless otherwise specified, all percentages used in the present invention are by mass.

[0054] Finally, it should be noted that the above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art can still modify the technical solutions described in the aforementioned embodiments or replace some of the technical features therein by equivalents. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance, characterized in that: The planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance has a molecular structure as shown below: ； In the formula, -BMes2 is diphenylboryl and -NPh2 is diphenylamino.

2. A method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance, characterized in that: The following steps are included: With 4-iodo-15-diphenylamino[2.2]cyclomorph as the starting material, a coupling reaction is first carried out to obtain 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph; and then a borylation reaction is carried out to obtain a planar chiral[2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

3. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 2, characterized in that: The coupling reaction method is that, in a solvent environment, in the presence of cuprous iodide and bistriphenylphosphine palladium dichloride, 4-iodo-15-diphenylamino[2.2]cyclomorph reacts with 2-bromophenylacetylene to obtain 4-(2-bromophenylacetylene)-15-diphenylamino[2.2]cyclomorph; The borylation reaction method is that, in a solvent environment, 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorph is first contacted with n-butyl lithium for reaction, and then contacted with diphenylboron fluoride for reaction, so as to obtain a planar chiral [2.2]cyclomorph organic small molecule with high solid-state luminescence performance.

4. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 3, characterized in that: In the coupling reaction, the molar ratio of 4-iodo-15-diphenylamino[2.2]cyclomorph, 2-bromophenylacetylene, bistriphenylphosphine palladium dichloride and cuprous iodide is 1:1-1.3:0.05-0.1:0.06-0.

09.

5. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 3, characterized in that: In the coupling reaction, the reaction time of 4-iodo-15-diphenylamino[2.2]cyclophane and 2-bromophenylacetylene is 12-18 hours.

6. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 3, characterized in that: In the borylation reaction, the molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclophane to n-butyllithium is 1:1.8-2.2; The molar ratio of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclomorpha to diphenylborane is 1:2-3.

7. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 3, characterized in that: In the borylation reaction, the reaction time of 4-(2-bromophenylethynyl)-15-diphenylamino[2.2]cyclophane and n-butyllithium is 1.5-2h.

8. The method for preparing a planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance according to claim 3, characterized in that: In the borylation reaction, the contact reaction time with dimethyl borofluoride is 10-15 hours.

9. Use of the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance as claimed in claim 1 or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the preparation method according to any one of claims 2 to 8 as a circularly polarized luminescent material.

10. An application of the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance as claimed in claim 1 or the planar chiral [2.2] cyclosimulated organic small molecule with high solid-state luminescence performance prepared by the preparation method according to any one of claims 2 to 8 in the fields of three-dimensional display, optical information storage and processing, biological probes, and CPL sensors.

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