A chiral molecule based on tetraphenylpyrazine and derivatives or enantiomers thereof or preparation method and application

Abstract

The application discloses a kind of chiral molecules based on tetraphenylpyrazine and its derivative or its enantiomer or preparation method and application.The chiral molecules based on tetraphenylpyrazine and its derivative have the structure shown in the following formula (I).Wherein, R1, R2 are each independently selected from hydrogen, alkyl containing 1-9 carbon atoms, alkoxy containing 1-9 carbon atoms, halogen;R3, R4, R5 are each independently selected from hydrogen or halogen;R6 is each independently selected from 1-22 carbon atoms straight-chain alkyl;Binaphthyl has the chiral configuration of R or S.The chiral molecules based on tetraphenylpyrazine and its derivative can produce deep blue light emission in different states, have very high fluorescence quantum yield and very high brightness in thin film state, and the enantiomer also has strong mirror chiral property, and can be applied in the fields of illumination, three-dimensional display and full-color display.

Description

TECHNICAL FIELD

[0001] The present application belongs to the field of organic light-emitting materials, and more particularly relates to a chiral molecule based on tetraphenylpyrazine and derivatives or enantiomers thereof or a preparation method and application. BACKGROUND

[0002] Since entering the new era, human society has been developing vigorously, and technology has been developing with the fast car of the new era and has been pouring into the tide of globalization. The continuous change of information technology gradually affects the channel of people's access to information. With the rapid development and popularization of mobile Internet, mobile communication devices have become necessities in people's daily life, and display technology, as a major means of information presentation, has also begun to develop rapidly.

[0003] Currently, the display device presents various complex pictures based on three primary colors (red, green, and blue). However, the development of three primary color materials is not synchronized. Efficient green and red light materials have achieved commercial application, but efficient blue light materials are still relatively scarce, and there is an urgent need to develop high-efficiency deep blue light materials. Traditional blue light materials such as anthracene, fluorene, and pyrene have very planar and rigid molecular structures, which makes them have high fluorescence quantum yield in solution state, but in the aggregation state, they will have ACQ effect of fluorescence weakening or even complete quenching, which seriously limits their application in the aggregation state. Fortunately, in 2001, Professor Tang Benzhong's research group discovered the AIE phenomenon which is completely opposite to it. Molecules with AIE phenomenon have weak fluorescence or do not emit light in solution state, but in the aggregation state, due to the hindering of twisted molecular structure movement, the non-radiative decay path is blocked, and the radiation channel is opened, realizing the enhancement of fluorescence emission. Based on the excellent photophysical properties of AIE molecules in the aggregation state, it perfectly makes up for the application defects of ACQ molecules in the aggregation state. Developing high-brightness deep blue light materials based on AIE molecules has inherent advantages.

[0004] Chiral materials have attracted widespread attention from many scholars due to their mysterious chiral properties. In particular, chiral fluorescent molecules have excellent chiral properties due to their chiral properties. Many chiral molecules with high luminescent properties also have excellent chiral properties. Therefore, combining AIE molecules with excellent photophysical properties with chiral molecules can often achieve 1+1>2 effect and obtain chiral molecules with excellent photophysical properties. In addition, chiral molecules have potential application prospects in the field of 3D display, which promotes the development of high-brightness deep blue chiral molecules.

[0005] Therefore, based on the urgent need for high-fluorescence quantum yield high-brightness deep blue chiral materials, developing high-fluorescence quantum yield high-brightness deep blue chiral materials is of great significance to promote the development of display and lighting fields. SUMMARY

[0006] In view of the above technical problems, the primary object of the present application is to provide a chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof. The chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof has deep blue light emission in solution state, thin film state and powder state, and has very high fluorescence quantum yield and high brightness in thin film state, and has chiral property.

[0007] The second object of the present application is to provide a preparation method of the chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof.

[0008] The third object of the present application is to provide an application of the chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof in preparing a luminescent material.

[0009] The fourth object of the present application is to provide a luminescent chiral material.

[0010] The fifth object of the present application is to provide a luminescent thin film.

[0011] The sixth object of the present application is to provide an application of the luminescent thin film in the field of illumination, three-dimensional display or full-color display.

[0012] In order to achieve the above objects, the present application is implemented by the following technical solutions:

[0013] A chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof, the chiral molecule based on tetraphenylpyrazine and its derivative has the following structure shown in formula (I):

[0014]

[0015] wherein R1, R2 are each independently selected from hydrogen, alkyl containing 1-9 carbon atoms, alkoxy containing 1-9 carbon atoms, halogen; R3, R4, R5 are each independently selected from hydrogen or halogen; R6 are each independently selected from linear alkyl of 1-22 carbon atoms; in the structure shown in formula (I), the binaphthyl has R or S chiral configuration.

[0016] The present application provides a chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof, the chiral molecule based on tetraphenylpyrazine and its derivative or enantiomer thereof selects an AIE molecule tetraphenylpyrazine derivative with good thermal stability, light stability, chemical stability and high luminescent performance as a fluorophore, and selects a binaphthyl derivative with stable chiral stereoscopic configuration and high chiral induction as a chiral nucleus, the tetraphenylpyrazine endows the chiral molecule and its derivative with excellent luminescent performance, and the introduction of the binaphthyl makes the chiral molecule and its derivative have chiral property.

[0017] The test results show that the chiral molecule based on tetraphenylpyrazine and its derivative or its enantiomer has deep blue light absorption range at 385 nm in solution state, and the fluorescence spectrum in solution state, thin film state and powder state is in deep blue light emission wavelength range, the luminescent film prepared based on the above chiral molecule has very high fluorescence quantum yield and very high brightness, and the enantiomer has strong mirror chirality signal.

[0018] Preferably, the chiral molecule based on tetraphenylpyrazine and its derivative comprises enantiomers as shown in formula (R-I) and formula (S-I):

[0019]

[0020] Preferably, R1 and R2 are each independently selected from hydrogen, alkyl containing 1-3 carbon atoms, alkoxy containing 1-3 carbon atoms, halogen; R3, R4 and R5 are each independently selected from hydrogen or chlorine; and R6 is each independently selected from linear alkyl containing 1-8 carbon atoms.

[0021] Preferably, the chiral molecule based on tetraphenylpyrazine and its derivative has any one of the following structures:

[0022]

[0023] Further, the present application also claims a preparation method of a chiral molecule based on tetraphenylpyrazine and its derivative or its enantiomer, which comprises: obtaining the compound of formula (I) by subjecting a compound of formula (II) to a Sonogashira reaction with a compound of formula (III).

[0024]

[0025] In some specific embodiments, the preparation method of the chiral molecule based on tetraphenylpyrazine and its derivative or its enantiomer comprises: mixing the compound of formula (II), the compound of formula (III), a solvent, a reaction medium, a palladium catalyst and a copper catalyst, heating the mixture to react, purifying, and obtaining the compound of formula (I).

[0026] Preferably, the palladium catalyst is zero-valent or divalent palladium catalyst.

[0027] Further preferably, the palladium catalyst is one or more of dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium and dichlorobis(diphenylphosphino)ferrocene palladium.

[0028] Preferably, the copper catalyst is monovalent copper catalyst.

[0029] Further preferably, the copper catalyst is one or more of cuprous iodide, cuprous bromide, cuprous chloride.

[0030] Preferably, the reaction medium is one or more of triethylamine, diethylamine, potassium carbonate.

[0031] Preferably, the molar ratio of the compound of formula (II) to the compound of formula (III) is 1:2-6.

[0032] Preferably, the solvent is one or more of tetrahydrofuran, N,N-dimethylformamide, 1,4-dioxane.

[0033] Preferably, the temperature of the reaction is 80-90℃.

[0034] Preferably, the operation of purification is as follows: after the reaction is completed, the reaction solution is cooled to room temperature, the solvent is removed by distillation under reduced pressure, then dichloromethane is added for dissolution, followed by washing, drying and filtration, and then the solvent is removed by distillation under reduced pressure to obtain the crude product, which is then finely purified by column chromatography.

[0035] Preferably, the drying is performed using anhydrous sodium sulfate.

[0036] Preferably, the column chromatography uses a mixed solvent of petroleum ether and dichloromethane as the eluent. Further preferably, the volume ratio of the petroleum ether to dichloromethane is 2-5:1.

[0037] Further, the present application claims a kind of based on tetraphenylpyrazine chiral molecule and its derivative or its enantiomer in the application of preparing luminescent material.

[0038] Further, the present application also claims a kind of luminescent chiral material, comprising the above-mentioned based on tetraphenylpyrazine chiral molecule and its derivative or its enantiomer.

[0039] The chiral molecule and its derivative or its enantiomer provided by the present application have deep blue light emission in solution state, thin film state and powder state, and the emission wavelengths are 437nm, 434nm and 449nm respectively, all of which are within the deep blue light emission wavelength range. The thin film state has very high fluorescence quantum yield and very high brightness, and the brightness of the thin film state is as high as 58554.2L·mol -1 cm -1 At the same time, the enantiomer presents strong mirror symmetry circular dichroism spectrum and has chiral property.

[0040] Based on this, the present application claims a kind of luminescent film, comprising:

[0041] (a) based on tetraphenylpyrazine chiral molecule and its derivative or its enantiomer;And

[0042] (b) a polyacrylate polymer.

[0043] The mass ratio of the chiral molecule based on tetraphenylpyrazine and its derivative or its enantiomer to the polyacrylate polymer is 1:10-100.

[0044] Preferably, the polyacrylate polymer is polymethyl methacrylate.

[0045] Further, the application claims the application of the light-emitting film in the fields of lighting, three-dimensional display and full-color display.

[0046] Compared with the prior art, the application has the following beneficial effects:

[0047] The application provides a chiral molecule based on tetraphenylpyrazine and its derivative or its enantiomer, which has a maximum emission peak in a fluorescence spectrum in a solution state, a film state and a powder state in a deep blue light emission range, and has very high fluorescence quantum yield and very high brightness in the film state, and the brightness can reach 58554.2 L·mol -1 cm -1 Meanwhile, the enantiomer has a circular dichroism spectrum in the film state which presents a clear mirror symmetry shape, indicating that the enantiomer has chiral characteristics. BRIEF DESCRIPTION OF DRAWINGS

[0048] Figure 1 It is a nuclear magnetic resonance hydrogen spectrum of the compound of formula (R-L-V) in Example 1 with deuterated chloroform as a solvent.

[0049] Figure 2 It is a nuclear magnetic resonance carbon spectrum of the compound of formula (R-L-V) in Example 1 with deuterated chloroform as a solvent.

[0050] Figure 3 It is a nuclear magnetic resonance hydrogen spectrum of the compound of formula (S-L-V) in Example 1 with deuterated chloroform as a solvent.

[0051] Figure 4 It is a nuclear magnetic resonance carbon spectrum of the compound of formula (S-L-V) in Example 1 with deuterated chloroform as a solvent.

[0052] Figure 5 It is a nuclear magnetic resonance hydrogen spectrum of the compound of formula (R-V) in Example 2 with deuterated chloroform as a solvent.

[0053] Figure 6 It is a nuclear magnetic resonance carbon spectrum of the compound of formula (R-V) in Example 2 with deuterated chloroform as a solvent.

[0054] Figure 7 It is a nuclear magnetic resonance hydrogen spectrum of the compound of formula (S-V) in Example 2 with deuterated chloroform as a solvent.

[0055] Figure 8 The UV absorption spectrum and fluorescence spectrum of the sample of the compound of formula (R-V) and the compound of formula (S-V) prepared in Example 2 are shown in FIG. 2. In FIG. 2,

[0056] Figure 9 The UV absorption spectrum and fluorescence spectrum of the sample of the compound of formula (R-L-V) and the compound of formula (S-L-V) prepared in Example 1 are shown in FIG. 1. In FIG. 1, Figure 9 A in FIG. 1 is the UV absorption spectrum of the sample of the compound of formula (R-L-V) and the compound of formula (S-L-V); Figure 9 B in FIG. 1 is the fluorescence spectrum of the compound of formula (R-L-V) in solution, in powder, and in the thin film prepared in Example 3; Figure 9 C in FIG. 1 is the fluorescence spectrum of the compound of formula (S-L-V) in solution, in powder, and in the thin film prepared in Example 3.

[0057] Figure 10 The UV absorption spectrum and fluorescence spectrum of the sample of the compound of formula (R-V) and the compound of formula (S-V) prepared in Example 2 are shown in FIG. 2. In FIG. 2, Figure 10 A in FIG. 2 is the UV absorption spectrum of the sample of the compound of formula (R-V) and the compound of formula (S-V); Figure 10 B in FIG. 2 is the fluorescence spectrum of the compound of formula (R-V) in solution, in powder, and in the thin film prepared in Example 3; Figure 10 C in FIG. 2 is the fluorescence spectrum of the compound of formula (S-V) in solution, in powder, and in the thin film prepared in Example 3.

[0058] Figure 11 The fluorescence quantum yield and brightness map of the thin films of the compound of formula (R-L-V), the compound of formula (S-L-V), the compound of formula (R-V), and the compound of formula (S-V) prepared in Example 3 are shown in FIG. 3. In FIG. 3, Figure 11 A in FIG. 3 is the fluorescence quantum yield of the thin films of the compound of formula (R-L-V), the compound of formula (S-L-V), the compound of formula (R-V), and the compound of formula (S-V) prepared in Example 3; Figure 11 B in FIG. 3 is the brightness map of the thin films of the compound of formula (R-L-V), the compound of formula (S-L-V), the compound of formula (R-V), and the compound of formula (S-V) prepared in Example 3.

[0059] Figure 12 The circular dichroism spectrum of the thin films of the compound of formula (R-L-V) and the compound of formula (S-L-V) prepared in Example 3 is shown in FIG. 4.

[0060] Figure 13 The circular dichroism spectrum of the thin films of the compound of formula (R-V) and the compound of formula (S-V) prepared in Example 3 is shown in FIG. 5. DETAILED DESCRIPTION

[0061] The present application is further described in conjunction with the accompanying drawings and specific examples, which are intended to illustrate but not to limit the present application. Unless otherwise specified, the reagents, methods and apparatus employed in the present application are of a kind commonly used in the art.

[0062] Example 1

[0063] 1. Chiral molecule formula (R-L-V) compound based on tetraphenylpyrazine

[0064]

[0065] (1) In a reaction bottle, formula (I) compound, trimethylsilyl acetylene, dichlorobis(triphenylphosphine)palladium, cuprous iodide, triphenylphosphine (molar ratio of raw materials is 1:2:0.02:0.04:0.04) were added, tetrahydrofuran and triethylamine were added respectively under nitrogen atmosphere, heated to 80°C and refluxed overnight, purified to obtain intermediate formula (II) compound.

[0066] (2) In a reaction bottle, formula (II) compound was added, tetrahydrofuran was added under nitrogen atmosphere, then potassium hydroxide methanol solution (concentration is 0.56 mol / L) was added, the molar ratio of formula (II) compound and potassium hydroxide is 1:6, the reaction was carried out at room temperature overnight, after the reaction was completed, dilute hydrochloric acid was added to quench the reaction, purified to obtain intermediate formula (III) compound.

[0067] (3) In a 500 mL two-necked round bottom flask, formula (R-L-IV) compound (1.2 g, 1.7 mmol), formula (III) compound (1.7 g, 4 mmol), dichlorobis(triphenylphosphine)palladium (124 mg, 0.18 mmol), cuprous iodide (13.5 mg, 0.07 mmol) were added in turn, then 84 mL of tetrahydrofuran (THF) and 42 mL of triethylamine were added under nitrogen atmosphere. Subsequently, it was stirred at 85°C for 24 hours. The reaction mixture was concentrated under vacuum, dissolved in dichloromethane (DCM), washed with water three times, dried with anhydrous sodium sulfate, filtered, the obtained organic phase was concentrated under vacuum, further purified by silica gel chromatography column (eluent: V(petroleum ether (PE)) / V(dichloromethane (DCM))=2:1) to obtain 942 mg of chiral molecule formula (R-L-V) compound based on tetraphenylpyrazine with a yield of 40%, and the product was white powder. The proton nuclear magnetic resonance spectrum of formula (R-L-V) compound in deuterated chloroform solvent and the carbon nuclear magnetic resonance spectrum of formula (R-L-V) compound in deuterated chloroform solvent are shown in Figure 1 and 2 .

[0068] The corresponding spectrum data values are as follows: 1H NMR (400 MHz, CDCI3) δ (ppm): 8.39 (d, 2H), 7.91-7.52 (m, 22H), 7.51-7.29 (m, 18H), 7.22 (d, 2H), 7.10 (d, 2H), 4.05-3.90 (m, 4H), 1.43 (d, 4H), 1.19-0.87 (m, 12H), 0.77 (t, 6H).

[0069] 13 C NMR (400 MHz, CDCI3) δ (ppm): 154.02, 148.61, 147.41, 138.76, 138.31, 132.24, 131.66, 130.56, 129.93, 128.86, 128.39, 123.18, 121.37, 121.08, 119.89, 94.92, 88.22, 69.59, 32.28, 29.17, 25.36, 22.52, 13.96.

[0070] 2. Chiral molecular compound of formula (S-L-V) based on tetraphenylpyrazine

[0071] The compound of formula (S-L-V) and formula (R-L-V) are prepared by the same method, and they are enantiomers of each other. The compound of formula (S-L-V) prepared is shown by the following1H NMR spectrum with deuterated chloroform as solvent, and13C NMR spectrum with deuterated chloroform as solvent: Figure 3 and 4 .

[0072] The corresponding spectral data values are shown as follows: 1 H NMR (400 MHz, CDCI3) δ (ppm): 8.39 (d, 2H), 7.91-7.52 (m, 22H), 7.51-7.29 (m, 18H), 7.22 (d, 2H), 7.10 (d, 2H), 4.05-3.90 (m, 4H), 1.43 (d, 4H), 1.19-0.87 (m, 12H), 0.77 (t, 6H).

[0073] 13C NMR (400 MHz, CDCI3) δ (ppm): 154.14, 148.72, 147.52, 138.87, 138.42, 132.35, 131.77, 130.68, 130.09, 128.97, 128.50, 127.93, 123.30, 121.48, 121.19, 120.00, 95.04, 88.33, 77.48, 77.16, 76.84, 69.70, 31.39, 29.28, 25.47, 22.63, 14.07.

[0074] Example 2

[0075] 1. Chiral molecular compound based on tetraphenylpyrazine of formula (R-V)

[0076]

[0077] (1) In a 500 mL two-necked round bottom flask, compound of formula (R-IV) (1 g, 1.8 mmol), compound of formula (III) (1.7 g, 4 mmol), palladium dichloride bis-triphenylphosphine (123 mg, 0.18 mmol), cuprous iodide (13.4 mg, 0.07 mmol) were successively added, then 84 mL of THF and 42 mL of triethylamine were added under nitrogen atmosphere. Subsequently, the mixture was stirred at 85°C for 24 hours. The reaction completed mixture was concentrated under vacuum, then dissolved in DCM, washed with water three times, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum, then further purified by silica gel chromatography column (eluent: V(PE) / V(DCM)=2:1) to obtain 968 mg of chiral molecular compound based on tetraphenylpyrazine of formula (R-V) with a yield of 45%, and the product was a white powder.

[0078] The1H NMR spectrum of compound of formula (R-V) in deuterated chloroform as solvent, the13C NMR spectrum of compound of formula (R-V) in deuterated chloroform as solvent are shown in Figure 5 and 6 .

[0079] The corresponding spectral data values are shown as follows: 1 H NMR (400 MHz, CDCI3) δ (ppm): 8.41 (d, 2H), 7.84 - 7.49 (m, 22H), 7.38 (d, 18H), 7.28 - 7.17 (m, 2H), 7.08 (d, 2H), 5.71 - 3.04 (m, 4H), 1.11 (t, 6H).

[0080] 13C NMR (400 MHz, CDCI3) d (ppm): 153.79, 148.56, 147.34, 138.77, 138.28, 132.17, 131.62, 130.58, 129.90, 128.81, 128.34, 127.81, 127.27, 125.16, 123.09, 121.40, 121.05, 119.92, 94.98, 88.13, 65.13, 29.69, 29.41, 14.86.

[0081] 2. Chiral molecule of formula (S-V) based on tetraphenylpyrazine

[0082] The compound of formula (S-V) and formula (R-V) are prepared by the same method, and they are enantiomers of each other. The compound of formula (S-V) prepared is shown by the following1H NMR spectrum with deuterated chloroform as solvent, and13C NMR spectrum with deuterated chloroform as solvent. Figure 7 and 8

[0083] The corresponding spectral data values are shown as follows: 1 H NMR (400 MHz, CDCI3) d (ppm): 8.41 (d, 2H), 8.02-7.53 (m, 22H), 7.53-7.29 (m, 18H), 7.22 (dd, 2H), 7.15-6.98 (m, 2H), 4.16-4.01 (m, 4H), 1.11 (t, 6H).

[0084] 13 C NMR (400 MHz, CDCI3) d (ppm): 154.26, 149.02, 147.81, 139.24, 138.75, 132.63, 132.09, 131.04, 130.79-130.04, 129.27, 129.04-128.55, 128.27, 127.74, 125.63, 123.56, 121.87, 121.52, 120.39, 95.45, 88.60, 77.80, 77.48, 77.16, 65.59, 30.16, 15.33.

[0085] Example 3 Preparation of thin film of chiral molecule based on tetraphenylpyrazine and its derivatives

[0086] ​1 mg of the chiral molecules based on tetraphenylpyrazine and its derivatives of formula (R-L-V) compound, formula (S-L-V) compound, formula (R-V) compound and formula (S-V) compound prepared in Example 1 and Example 2 respectively were mixed with 100 mg of polymethyl methacrylate (PMMA), 1 mL of chloroform was added as solvent, after being dissolved thoroughly, 100 μL of the mixed solvent was dropped on a 1 x 2 cm quartz sheet, the solvent was evaporated at room temperature, and the corresponding formula (R-L-V) compound thin film, formula (S-L-V) compound thin film, formula (R-V) compound thin film and formula (S-V) compound thin film were obtained after the solvent was completely evaporated.

[0087] Example 4 Optical physical property test of the chiral molecules based on tetraphenylpyrazine and its derivatives

[0088] Firstly, the UV absorption spectrum of the tetrahydrofuran solution of the chiral molecules based on tetraphenylpyrazine and its derivatives of formula (R-L-V) compound, formula (S-L-V) compound, formula (R-V) compound and formula (S-V) compound prepared in Example 1 and Example 2 was tested (the concentration was 1 x 10 -5 mol / L).

[0089] The test results are shown in A of Figure 9 and A of Figure 10 The maximum absorption wavelength of the four chiral molecules based on tetraphenylpyrazine and its derivatives in the tetrahydrofuran solution is in the deep blue light absorption range of 385 nm, and the molar extinction coefficient of formula (R-L-V) compound and formula (S-L-V) compound can reach 80700 L·mol -1 cm -1 , and the molar extinction coefficient of formula (R-V) compound and formula (S-V) compound can reach 81100 L·mol -1 cm -1 .

[0090] The fluorescence spectrum test results of the chiral molecules based on tetraphenylpyrazine and its derivatives of formula (R-L-V) compound, formula (S-L-V) compound, formula (R-V) compound and formula (S-V) compound prepared in Example 1 and Example 2 in solution state, powder state and thin film state prepared in Example 3 are shown in B and C of Figure 9 and B and C of Figure 10 The fluorescence emission peaks of the four molecules in the three states are all in the deep blue light emission range. At the same time, the fluorescence quantum yields of the thin film state are shown in A of Figure 11 , which are 71.8%, 68.6%, 72.2% and 71.9% respectively, showing very high fluorescence quantum yield.

[0091] The brightness calculation method based on chiral molecules and their derivatives of tetraphenylpyrazine is as follows: the ultraviolet absorption spectrum of chiral molecules and their derivatives based on tetraphenylpyrazine is tested, the molar extinction coefficient corresponding to the maximum absorption wavelength is obtained, the fluorescence quantum yield is tested, and the brightness is obtained by multiplying the measured molar extinction coefficient by the fluorescence quantum yield.

[0092] Based on the above calculation method, the brightness of the chiral molecule and its derivatives (RLV), (SLV), (RV), and (SV) compounds prepared in Examples 1 and 2, based on tetraphenylpyrazine, was calculated. Figure 11 As shown in B, the values ​​are: 57942.6 L·mol⁻¹ -1 cm -1 55360.2 L·mol -1 cm -1 58554.2 L·mol -1 cm -1 and 58310.9 L·mol -1 cm -1 They all exhibit very high brightness values.

[0093] Example 5: Chiral Tests Based on Tetraphenylpyrazine Chiral Molecules and Their Derivatives

[0094] The circular dichroism spectral results of the thin films based on the chiral molecule of tetraphenylpyrazine and its derivatives, namely, RLV, SLV, RV, and SV compounds, prepared in Example 3 are as follows: Figure 12 and Figure 13 As shown, the circular dichroism spectra of compounds of formula (RLV), (SLV), (RV), and (SV), which are enantiomers, all exhibit strong mirror-symmetry patterns. Figure 12 The Cotton peak at 396 nm is attributed to the characteristic absorption of the tetraphenylpyrazine unit in compounds of formula (RLV) and formula (SLV). Figure 13 The Cotton peak at 390 nm is attributed to the characteristic absorption of the tetraphenylpyrazine unit in compounds (RV) and (SV), indicating that the chirality of the binaphthalene chiral core was successfully transferred to the entire molecular backbone of the four molecules.

[0095] The foregoing embodiments are merely illustrative, used to explain some features of the method described in this invention. The appended claims are intended to claim the broadest possible scope, and the embodiments presented herein are demonstrated by the applicant's actual experimental results. Therefore, the applicant intends that the appended claims are not limited by the selection of examples illustrating the features of the invention. Some numerical ranges used in the claims also include sub-ranges within them, and variations within these ranges should also be interpreted as being covered by the appended claims where possible.

Claims

1. A chiral molecule based on tetraphenylpyrazine or an enantiomer thereof, characterized in that, The chiral molecule based on tetraphenylpyrazine has the following formula (I) structure: wherein R1, R2 are each independently selected from hydrogen, alkyl group containing 1-9 carbon atoms, alkoxy group containing 1-9 carbon atoms, halogen; R3, R4, R5 are each independently selected from hydrogen or halogen; R6 are each independently selected from linear alkyl group of 1-22 carbon atoms; In the structure of formula (I), the binaphthyl has R or S chiral configuration.

2. The chiral molecule or an enantiomer thereof according to claim 1, wherein The chiral molecule based on tetraphenylpyrazine comprises enantiomers as formula (R-I) and formula (S-I): 。 3. The chiral molecule or an enantiomer thereof according to claim 1, wherein wherein, R1, R2 are each independently selected from hydrogen, alkyl group containing 1-3 carbon atoms, alkoxy group containing 1-3 carbon atoms, halogen; R3, R4, R5 are each independently selected from hydrogen or chlorine; R6 are each independently selected from linear alkyl group of 1-8 carbon atoms.

4. The chiral molecule or an enantiomer thereof according to claim 1, wherein The chiral molecule based on tetraphenylpyrazine has any one of the following structures: 。 5. Process for the preparation of chiral molecules based on tetraphenylpyrazine or enantiomers thereof according to any one of claims 1 to 4, characterized in that, The compound of formula (II) is reacted with the compound of formula (III) through Sonogashira reaction to obtain the compound of formula (I); the reaction formula is shown as follows: 。 6. Use of the chiral molecule based on tetraphenylpyrazine or its enantiomer according to any one of claims 1-4 in the preparation of a light-emitting material.

7. A luminescent chiral material, characterized in that The light-emitting material comprises the chiral molecule based on tetraphenylpyrazine or its enantiomer according to any one of claims 1-4.

8. A light emitting film, characterized by The light-emitting material comprises: (a) the chiral molecule based on tetraphenylpyrazine or its enantiomer according to any one of claims 1-4; and (b) a polyacrylate polymer; The mass ratio of the chiral molecule based on tetraphenylpyrazine or its enantiomer to the polyacrylate polymer is 1:10-100.

9. The light emitting film of claim 8, wherein, The polyacrylate polymer is polymethyl methacrylate.

10. Use of the light-emitting film according to claims 8-9 in the field of illumination, three-dimensional display or full-color display.

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