A binaphthylamine derivative, its preparation method and use

Abstract

This application relates to the field of organic electroluminescence technology, and discloses a binaphthylamine derivative, its preparation method, and its applications. Based on the organic compounds containing binaphthylamine groups as donor structures, this application synthesizes a series of D-A structure molecules by linking different triazine ring derivative acceptors. These molecules exhibit high quantum yield and circularly polarized light properties, and can be used to prepare highly efficient organic electroluminescent devices.

Description

Technical Field

[0001] This application relates to the field of organic light-emitting materials technology, and more specifically, to a binaphthylamine derivative, its preparation method, and its application. Background Technology

[0002] Circularly polarized luminescent materials are a special class of luminescent materials that emit circularly polarized light with specific chirality. This phenomenon is caused by the difference in emission intensity between left-handed and right-handed circularly polarized light when the chiral luminescent material is stimulated to emit light. Circularly polarized luminescent (CPL) materials have attracted widespread attention due to their important applications in many fields, including 3D displays, optical storage, optical anti-counterfeiting, and asymmetric synthesis.

[0003] Therefore, how to increase the circular polarization emission asymmetry factor of organic systems while maintaining high luminescence efficiency is a key research issue in this field.

[0004] Patent application content

[0005] To overcome one of the problems existing in the prior art, the primary objective of this application is to provide a binaphthylamine derivative. This binaphthylamine derivative can increase the circularly polarized emission asymmetry factor of organic systems while maintaining high luminescence efficiency.

[0006] Another objective of this application is to provide a method for preparing the above-mentioned binaphthylamine derivative.

[0007] Another objective of this application is to provide the application of the aforementioned binaphthylamine derivative.

[0008] The above-mentioned objectives of this application are achieved through the following technical solutions:

[0009] A binaphthylamine derivative, which can be used as a circularly polarized luminescent material, has the molecular structure shown in formula (1) or formula (2) as follows:

[0010]

[0011] Wherein, R1 to R4, R6 and R7 are benzene derivatives or triazine derivatives or other substitutes, and R5 and R8 are substituents composed of various carbon, nitrogen, sulfur, silicon and oxygen atoms, and R5 and R8 form a ring structure of 4 atoms or more with the benzene on the naphthalene.

[0012] Ring a and ring b are bonded to two cyclic carbon atoms respectively to form a ring structure with more than four atoms; the atoms in the ring structure are selected from carbon atoms or various heteroatoms.

[0013] Preferably, when R1 to R8 represent substituents, each is independently selected from a benzene ring and its derivatives or a variety of triazine derivatives.

[0014] Preferably, the a, b, c, and d ring structures have substituents or do not have substituents, and the substituents of the ring structures are either not bonded to each other or are bonded to form further ring structures.

[0015] Preferably, when R1 to R8 represent substituents, each substituent is individually selected from a benzene ring and its derivatives or from various triazine derivatives.

[0016] More preferably, the substituent is selected from any one of the following: I to XX:

[0017]

[0018] This application also provides a binaphthylamine derivative, which can be used as a circularly polarized luminescent material. The general structural formula of the binaphthylamine derivative can be represented by any one of the following formulas (3) and (4):

[0019]

[0020] The selectable range of R9 to R14 is the same as that of R1 to R8.

[0021] This application also provides a method for preparing the above-mentioned binaphthylamine derivative, comprising the following steps:

[0022] S1. Preparation of intermediate product R / S-2

[0023] [1,1'-binaphthyl]-2,2'-diamine, bromobenzene, tris(dibenzylacetone)dipalladium, 1,1-binaphthyl-2,2-bis(diphenylphosphine) and sodium tert-butoxide were dispersed in a 30 mL toluene double-necked flask under an inert gas atmosphere and reacted at 110 °C for 12 hours. After the reaction was completed, the solvent was evaporated, and the crude product was further purified to obtain the intermediate product R / S-2.

[0024] S2. Preparation of intermediate product R / S-3

[0025] Under an inert gas atmosphere, the intermediate product R / S-2 obtained in step S1, iodobenzene, tris(dibenzylideneacetone)dipalladium, 1,1-binaphthyl-2,2-bisdiphenylphosphine and sodium tert-butoxide were dispersed in a toluene double-necked flask and reacted at 110°C for 6 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain intermediate product R / S-3.

[0026] S3. Preparation of the target product A3

[0027] Under an inert gas atmosphere, the intermediate product R / S-3 obtained in step S2, palladium acetate and copper acetate were dispersed in a 30 mL N'N-dimethylformamide double-necked flask and reacted at 130 °C for 12 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain the target product A3.

[0028] Preferably, the crude product in steps S1, S2 and S3 is further purified by column chromatography.

[0029] The application of the binaphthylamine derivative in this application is as a luminescent material, luminescent device, or smart material.

[0030] Compared with the prior art, the beneficial effects of this application are:

[0031] The binaphthylamine derivative provided in this application, using a binaphthylamine derivative as its core, exhibits pure blue light emission spectrum characteristics and high quantum yield, meeting the photoelectric performance requirements of organic electroluminescent devices. Simultaneously, it can increase the circularly polarized emission asymmetry factor of the organic system, exceeding a maximum of 1×10⁻⁶. -2 . Attached Figure Description

[0032] Figure 1 Compound A3 prepared in Example 1 of this application 1 HMNR diagram;

[0033] Figure 2 Compound A11 prepared in Example 2 of this application 1 HMNR diagram;

[0034] Figure 3 The circular dichroism chromatogram of compound A3 prepared in Example 1 of this application;

[0035] Figure 4 The circular dichroism chromatogram of compound A11 prepared in Example 2 of this application;

[0036] Figure 5 The CPL spectrum of compound A3 prepared in Example 1 of this application;

[0037] Figure 6 The ultraviolet absorption and emission patterns of compounds A3 and A11 prepared in Examples 1 and 2 of this application are shown.

[0038] Figure 7 This is a photoluminescence quantum yield diagram of compound A3 prepared in Example 1 of this application before deoxygenation;

[0039] Figure 8 This is a photoluminescence quantum yield diagram of compound A11 prepared in Example 2 of this application before deoxygenation. Detailed Implementation

[0040] The embodiments of this application will be described in detail below with reference to examples. However, those skilled in the art will understand that the following examples are for illustrative purposes only and should not be considered as limiting the scope of this application. Unless otherwise specified in the examples, conventional conditions or conditions recommended by the manufacturer shall apply. Reagents or instruments whose manufacturers are not specified are all commercially available conventional products.

[0041] It should be noted that:

[0042] Unless otherwise specified, all embodiments and preferred embodiments mentioned herein can be combined to form new technical solutions.

[0043] In this application, unless otherwise specified, percentage (%) or parts refer to weight percentage or parts relative to the composition.

[0044] Unless otherwise specified, the components or preferred components involved in this application may be combined to form new technical solutions.

[0045] In this application, unless otherwise stated, the numerical range "a~b" represents a shortened representation of any combination of real numbers between a and b, where a and b are real numbers. For example, the numerical range "1~5" means that all real numbers between "1~5" have been listed in this document, and "1~5" is simply a shortened representation of these numerical combinations.

[0046] The “scope” disclosed in this application may be in the form of a lower limit and an upper limit, and may be one or more lower limits and one or more upper limits, respectively.

[0047] In this application, unless otherwise stated, the various reactions or operation steps may be performed sequentially or in a particular order. Preferably, the reaction methods described herein are performed sequentially.

[0048] Unless otherwise stated, the technical and scientific terms used herein have the same meanings as those familiar to a person skilled in the art. Furthermore, any methods or materials similar to or equivalent to those described herein may also be used in this application.

[0049] This application provides a binaphthylamine derivative that can be used as a circularly polarized luminescent material, having the molecular structure shown in formula (1) or formula (2) below:

[0050]

[0051] In this context, R1 to R4, R6, and R7 are benzene derivatives, triazine derivatives, or other substitutes; R5 and R8 are substituents composed of various carbon, nitrogen, sulfur, silicon, and oxygen atoms; and R5 and R8 form a ring structure of 4 atoms or more with the benzene on the naphthalene. The solid arrows in formulas (1) and (2) represent cyclic structures, while the dashed arrows indicate that they can form rings or not. When the dashed arrows form rings, the non-radiative transitions of atoms can be reduced, thereby increasing the quantum yield.

[0052] Ring a and ring b are bonded to two cyclic carbon atoms respectively to form a ring structure with more than four atoms; the atoms in the ring structure are selected from carbon atoms or various heteroatoms.

[0053] The binaphthylamine derivatives provided in this application are organic compounds based on binaphthylamine derivatives. Using a binaphthylamine group as the donor structure, different triazine ring derivative acceptors are linked to synthesize a series of DA structure molecules. These molecules have pure blue light emission spectrum characteristics, high quantum yield, and circularly polarized light properties. They can be used to prepare high-efficiency organic electroluminescent devices and increase the circularly polarized light asymmetry factor of organic systems.

[0054] In some preferred embodiments, when R1 to R8 represent substituents, each is independently selected from a benzene ring and its derivatives or a variety of triazine derivatives.

[0055] In some preferred embodiments, the a, b, c, and d ring structures may or may not have substituents, and the substituents of the ring structures may not be bonded to each other or may be bonded to form further ring structures.

[0056] In some preferred embodiments, the atoms of the further ring structure have hydrogen atoms, deuterium atoms or substituents, wherein R6 and R7 are each independently selected from benzene rings and their derivatives or from various triazine derivatives.

[0057] In some preferred embodiments, when R1 to R8 represent substituents, each substituent is individually selected from a benzene ring and its derivatives or a variety of triazine derivatives.

[0058] In some preferred embodiments, the substituent is selected from any one of the following: I to XX:

[0059]

[0060] In some embodiments, this application also provides a binaphthylamine derivative, which can be used as a circularly polarized luminescent material, and the general structural formula of the binaphthylamine derivative can be represented by any one of the following formulas (3) and (4):

[0061]

[0062] Among them, R9~R 14 The selectable range is the same as that of R1 to R8.

[0063] In some more preferred embodiments, the binaphthylamine derivatives described in formulas (3) and (4) may preferably be any one of the following compounds A1 to A19:

[0064]

[0065]

[0066] This application also provides a method for preparing the above-mentioned binaphthylamine derivative, comprising the following steps:

[0067] S1. Preparation of intermediate product R / S-2

[0068] [1,1'-binaphthyl]-2,2'-diamine, bromobenzene, tris(dibenzylacetone)dipalladium, 1,1-binaphthyl-2,2-bis(diphenylphosphine) and sodium tert-butoxide were dispersed in a 30 mL toluene double-necked flask under an inert gas atmosphere and reacted at 110 °C for 12 hours. After the reaction was completed, the solvent was evaporated, and the crude product was further purified to obtain the intermediate product R / S-2.

[0069] S2. Preparation of intermediate product R / S-3

[0070] Under an inert gas atmosphere, the intermediate product R / S-2 obtained in step S1, iodobenzene, tris(dibenzylideneacetone)dipalladium, 1,1-binaphthyl-2,2-bisdiphenylphosphine and sodium tert-butoxide were dispersed in a toluene double-necked flask and reacted at 110°C for 6 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain intermediate product R / S-3.

[0071] S3. Preparation of intermediate product R / S-4

[0072] Under an inert gas atmosphere, the intermediate product R / S-3, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine, tris(dibenzylideneacetone)dipalladium, tritert-butylphosphide tetrafluoroborate and sodium tert-butoxide obtained in step S2 were dispersed in a 30 mL toluene double-necked flask and reacted at 110 °C for 4 hours. After the reaction was completed, the solvent was evaporated, and the crude product was further purified to obtain the intermediate product R / S-4.

[0073] S4. Preparation of the target product A3

[0074] Under an inert gas atmosphere, the intermediate product R / S-4 obtained in step S3, palladium acetate and copper acetate were dispersed in a 30 mL N'N-dimethylformamide double-necked flask and reacted at 130 °C for 12 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain the target product A3.

[0075] In some preferred embodiments, the crude product in steps S1, S2, S3 and S4 is further purified by column chromatography.

[0076] The preparation methods of the binaphthylamine derivatives A3 and A11 will be described in detail below.

[0077] Example 1

[0078] The preparation method of intermediate product R / S-2 is as follows:

[0079] Under a nitrogen atmosphere, [1,1'-binaphthyl]-2,2'-diamine R / S-1 (2.7 g, 9.5 mmol, 1 eq), bromobenzene (3.29 g, 20.9 mmol, 2.2 eq), tris(dibenzylacetone)dipalladium (Pd3(dba)2) (173 mg, 0.19 mmol, 0.02 eq), 1,1-binaphthyl-2,2-bis(diphenylphosphine) (BINAP) (118 mg, 0.19 mmol, 0.02 eq), and sodium tert-butoxide (NaOtBu) (2.6 g, 28.4 mmol, 3 eq) were dispersed in a 30 mL toluene double-necked flask. The reaction was carried out at 110 °C for 12 h. After the reaction was complete, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 4:1). Intermediate product R / S-2 was obtained, with a yield of 3.5 g (yield 85%).

[0080] The chemical reaction equations for this preparation step are as follows:

[0081]

[0082] S2. Preparation of intermediate product R / S-3

[0083] Under a nitrogen atmosphere, intermediate R / S-2 (1.75 g, 4 mmol, 1 eq), iodobenzene (0.897 g, 4.4 mmol, 1.1 eq), tris(dibenzylacetone)palladium (Pd3(dba)2) (73.2 mg, 0.08 mmol, 0.02 eq), 1,1-binaphthyl-2,2-bis(diphenylphosphine) (BINAP) (50 mg, 0.08 mmol, 0.02 eq), and sodium tert-butoxide (NaOtBu) (1.176 g, 12 mmol, 3 eq) were dispersed in a 30 mL toluene double-necked flask. The reaction was carried out at 110 °C for 6 hours. After the reaction was completed, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 4:1). Intermediate R / S-3 was obtained, with a yield of 1.9 g (80%).

[0084] The chemical reaction equations for this preparation step are as follows:

[0085]

[0086] S3. Preparation of intermediate product R / S-4

[0087] Under a nitrogen atmosphere, intermediate R / S-3 (1.0 g, 2 mmol, 1 eq), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (1.16 g, 3 mmol, 1.5 eq), tris(dibenzylacetone)dipalladium (Pd3(dba)2) (91.5 mg, 0.1 mmol, 0.05 eq), tri-tert-butylphosphide tetrafluoroborate (58 mg, 0.2 mmol, 0.1 eq), and sodium tert-butoxide (NaOtBu) (0.576 g, 6 mmol, 3 eq) were dispersed in a 30 mL toluene double-necked flask. The reaction was carried out at 110 °C for 4 hours. After the reaction was complete, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 5:1). Intermediate R / S-4 was given, with a yield of 1.4 g (85.5%).

[0088] The chemical reaction equations for this preparation step are as follows:

[0089]

[0090] S4. Preparation of the target product A3

[0091] Under a nitrogen atmosphere, intermediate R / S-4 (1.1 g, 1.34 mmol, 1 eq), palladium acetate (Pd(OAc)2) (607.9 mg, 2.69 mmol, 2 eq), and copper acetate (Cu(OAc)2) (727.62 mg, 4.02 mmol, 3 eq) were dispersed in a 30 mL double-necked flask containing N,N-dimethylformamide (DMF). The reaction was carried out at 110 °C for 4 hours. After the reaction was complete, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 5:1). Product A3 was given, with a yield of 1.01 g (92.4%).

[0092] The chemical reaction equations for this preparation step are as follows:

[0093]

[0094] Example 2

[0095] S1. Preparation of intermediate product R / S-2

[0096] Under a nitrogen atmosphere, [1,1'-binaphthyl]-2,2'-diamine R / S-1 (2.7 g, 9.5 mmol, 1 eq), bromobenzene (3.29 g, 20.9 mmol, 2.2 eq), tris(dibenzylacetone)dipalladium (Pd3(dba)2) (173 mg, 0.19 mmol, 0.02 eq), 1,1-binaphthyl-2,2-bis(diphenylphosphine) (BINAP) (118 mg, 0.19 mmol, 0.02 eq), and sodium tert-butoxide (NaOtBu) (2.6 g, 28.4 mmol, 3 eq) were dispersed in a 30 mL toluene double-necked flask. The reaction was carried out at 110 °C for 12 h. After the reaction was complete, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 4:1). Intermediate product R / S-2 was obtained, with a yield of 3.5 g (yield 85%).

[0097] The chemical reaction equations for this preparation step are as follows:

[0098]

[0099] S2. Preparation of intermediate product R / S-3'

[0100] Under a nitrogen atmosphere, intermediate R / S-2 (1.75 g, 4 mmol, 1 eq), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2.328 g, 6 mmol, 1.5 eq), tris(dibenzylacetone)dipalladium (Pd3(dba)2) (73.2 mg, 0.08 mmol, 0.02 eq), 1,1-binaphthyl-2,2-bis(diphenylphosphine) (BINAP) (50 mg, 0.08 mmol, 0.02 eq), and sodium tert-butoxide (NaOtBu) (1.176 g, 12 mmol, 3 eq) were dispersed in a 30 mL toluene double-necked flask. The reaction was carried out at 110 °C for 6 hours. After the reaction was completed, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 3:1). Intermediate product R / S-3' was obtained, with a yield of 3.2 g (76% yield).

[0101] The chemical reaction equations for this preparation step are as follows:

[0102]

[0103] S3. Preparation of the target product A11

[0104] Under a nitrogen atmosphere, intermediate R / S-3' (1.5 g, 1.43 mmol, 1 eq), palladium acetate (Pd(OAc)2) (646.4 mg, 2.86 mmol, 2 eq), and copper acetate (Cu(OAc)2) (776.5 mg, 4.29 mmol, 3 eq) were dispersed in a 30 mL double-necked flask containing N,N-dimethylformamide (DMF). The reaction was carried out at 110 °C for 4 hours. After the reaction was complete, the solvent was evaporated, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (v / v 5:1). Product A11 was obtained, with a yield of 1.37 g (91.4%).

[0105] The chemical reaction equations for this preparation step are as follows:

[0106]

[0107] Performance testing

[0108] The naphthylamine derivative compounds A3 and A11 prepared in Examples 1 and 2 were characterized and their performance was tested. The results are as follows: Figures 1-8 As shown.

[0109] The testing method is as follows:

[0110] Compound structure determination: A Bruker 400MHz superconducting nuclear magnetic resonance spectrometer was used with deuterated chloroform as the solvent; Ultraviolet absorption spectroscopy determination: A Shimadzu UV-2700 UV-Vis spectrophotometer was used, with a scanning range of [missing information].

[0111] 200–450 nm;

[0112] Emission spectroscopy detection: A steady-state / transient fluorescence spectrometer (FLS980) was used with an excitation wavelength of 365 nm.

[0113] The test temperature was 300K.

[0114] The test results are as follows:

[0115] from Figure 1 It can be seen that the characteristic wavenumber (ppm) of compound A3 prepared in Example 1 is 1 ¹H NMR (400MHz, Chloroform-d) δ 8.74–8.70 (m, 4H), 8.19 (d, J = 8.3Hz, 2H), 7.84 (dd, J = 16.4, 8.8Hz, 2H), 7.73 (d, J = 8.8Hz, 1H), 7.69–7.66 (m, 2H), 7.56 (qd, J = 8.6, 7.6, 3.6Hz, 7H), 7.20–7.07 (m, 2H), 6.83–6.44 (m, 21H). The ¹H molecular magnetic resonance peak energies correspond one-to-one with the target product, and the number is reasonable. This indicates that Example 1 successfully prepared the naphthylamine derivative compound A3, and that the compound has a simple structure and high purity.

[0116] from Figure 2 It can be seen that the characteristic wavenumber (ppm) of compound A11 prepared in Example 2 is 1 ¹H NMR (400MHz, Chloroform-d) δ 8.29–8.18 (m, 8H), 7.97 (d, J = 8.7Hz, 2H), 7.87 (d, J = 8.7Hz, 2H), 7.73 (d, J = 8.2Hz, 2H), 7.55 (d, J = 26.8Hz, 2H), 7.17 (t, J = 8.3Hz, 14H), 6.96–6.43 (m, 18H), 6.35 (d, J = 8.5Hz, 2H). The ¹H NMR peak energies correspond one-to-one with the target product, and the number is reasonable. This indicates that Example 2 successfully prepared the naphthylamine derivative compound A11, and that the compound has a simple structure and high purity.

[0117] Figure 3 The image shows a circular dichroism (CD) chromatogram of compound A3 prepared in Example 1 of this application. Figure 3It can be seen that the A3 compounds with R and S configurations have positive and negative CD signals, respectively, and the CD signals of the two are symmetrically distributed.

[0118] Figure 4 The circular dichroism (CD) chromatogram of compound A11 prepared in Example 2 of this application is shown. Figure 4 As can be seen, the R and S configurations of A11 compounds have positive and negative CD signals, respectively, and the CD signals of the two are symmetrically distributed.

[0119] Figure 5 The CPL spectrum of compound A3 prepared in Example 1 of this application is shown. Figure 5 It can be seen that the photoluminescence asymmetry factor of the S-configuration A3 compound exceeds 1×10⁻⁶. -2 .

[0120] Figure 6 The images show the UV absorption and emission spectra of compounds A3 and A11 prepared in Examples 1 and 2 of this application. Figure 6 As can be seen, the ultraviolet absorption peaks of compounds A3 and A11 prepared in this application are at wavelengths of 380 nm and 362 nm, respectively; while the fluorescence emission peaks of compounds A3 and A11 are at 450 nm and 440 nm, respectively, and the full width at half maximum (FWHM) of compounds A3 and A11 are 57 nm and 65 nm, respectively, which have high color purity blue light emission and can achieve short-wavelength emission.

[0121] Figure 7 This is a photoluminescence quantum yield diagram of compound A3 prepared in Example 1 of this application before deoxygenation. From... Figure 7 As can be seen from the above, the A3 prepared in this application achieved a photoluminescence quantum yield of 54.4% before deoxygenation, which is a high quantum yield and can be used to fabricate a more efficient circularly polarized light-emitting device.

[0122] Figure 8 This is a photoluminescence quantum yield diagram of compound A11 prepared in Example 2 of this application before deoxygenation. From... Figure 8 As can be seen from the above, the photoluminescence quantum yield of the A11 prepared in this application reached 48.2% before deoxygenation, which has a high quantum yield and can be used to make a more efficient circularly polarized light-emitting device.

[0123] In this application, besides compounds A3 and A11, several other binaphthylamine derivatives are structurally similar to compounds A3 / A11. They are compounds with circular polarization characteristics, consisting of a binaphthylamine derivative as the parent core and connected with a stable group and an electron-withdrawing triazine ring derivative group. Therefore, through similar preparation methods and the same characterization and testing methods, it can be known that such binaphthylamine derivative compounds all have circular polarization properties.

[0124] The binaphthylamine derivative in this application is an axially chiral molecule, while the triazine ring can serve as a chiral center or chiral inducing element. When the two are combined, a stronger chiral center or chiral environment is generated, thereby enhancing the CPL signal. The triazine ring can act as an electron acceptor, while the amino group of binaphthylamine can act as an electron donor. This structural design can facilitate efficient ICT processes, which are generally associated with enhanced luminescence efficiency and CPL activity. The introduction of the triazine ring expands the conjugated system of the binaphthylamine derivative, which helps to tune luminescent properties such as emission wavelength and luminescence efficiency. Furthermore, the binaphthylamine-triazine-bound derivative may form a more rigid molecular structure, which helps to reduce nonradiative transitions and improve luminescence efficiency.

[0125] This application provides a class of binaphthylamine derivatives. Organic compounds based on binaphthylamine derivatives use binaphthylamine groups as donor structures and connect different triazine ring derivative acceptors to synthesize a series of DA structure molecules with high quantum yield and circularly polarized light properties, which can be used to prepare high-efficiency organic electroluminescent devices.

[0126] Meanwhile, this application achieves the controllable preparation of binaphthylamine derivatives; the preparation cost is low, the raw material sources are wide-ranging, and large-scale production can be realized, which has broad commercial prospects.

[0127] In the description of this specification, the references to terms such as "one embodiment," "some embodiments," "illustrative embodiment," "example," "specific example," or "some examples," etc., indicate that a specific feature, structure, material, or characteristic described in connection with an embodiment or example is included in at least one embodiment or example of this application. In this specification, the illustrative expressions of the above terms do not necessarily refer to the same embodiment or example. Furthermore, the specific features, structures, materials, or characteristics described may be combined in any suitable manner in one or more embodiments or examples.

[0128] Although several embodiments of this application have been shown and described, those skilled in the art will understand that various changes, modifications, substitutions and variations can be made to these embodiments without departing from the principles and spirit of this application, the scope of which is defined by the claims and their equivalents.

Claims

1. A binaphthylamine derivative, which can be used as a circularly polarized luminescent material, characterized in that, It has the following molecular structural formula: 。 2. The method for preparing the binaphthylamine derivative according to claim 1, characterized in that, Includes the following steps: S1. Preparation of intermediate product R / S-2 [1,1'-binaphthyl]-2,2'-diamine, bromobenzene, tris(dibenzylacetone)dipalladium, 1,1-binaphthyl-2,2-bis(diphenylphosphine) and sodium tert-butoxide were dispersed in a toluene double-necked flask under an inert gas atmosphere and reacted at 110°C for 12 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain the intermediate product R / S-2. S2. Preparation of intermediate product R / S-3 Under an inert gas atmosphere, the intermediate product R / S-2 obtained in step S1, iodobenzene, tris(dibenzylideneacetone)dipalladium, 1,1-binaphthyl-2,2-bisdiphenylphosphine and sodium tert-butoxide were dispersed in a toluene double-necked flask and reacted at 110°C for 6 hours. After the reaction was completed, the solvent was evaporated and the crude product was further purified to obtain intermediate product R / S-3. S3. Preparation of intermediate product R / S-4 Under an inert gas atmosphere, the intermediate product R / S-3, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine, tris(dibenzylideneacetone)dipalladium, tritert-butylphosphide tetrafluoroborate and sodium tert-butoxide obtained in step S2 were dispersed in a 30 mL toluene double-necked flask and reacted at 110 °C for 4 hours. After the reaction was completed, the crude product obtained after evaporating the solvent was further purified to obtain intermediate product R / S-4. S4. Preparation of target product A3 Under an inert gas atmosphere, the intermediate product R / S-4 obtained in step S3, palladium acetate and copper acetate were dispersed in a 30 mL N'N-dimethylformamide double-necked flask and reacted at 130 °C for 12 hours. After the reaction was completed, the crude product obtained after evaporating the solvent was further purified to obtain the target product A3.

3. The method for preparing the binaphthylamine derivative according to claim 2, characterized in that, The crude product described in steps S1, S2, S3 and S4 is further purified by column chromatography.

4. The application of the naphthylamine derivative of claim 1 as a luminescent material, luminescent device, or smart material.

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