A non-aromatic circularly polarized room temperature phosphorescent material and its preparation and application

Abstract

The present invention discloses a non-aromatic circularly polarized room temperature phosphorescent material and its preparation and application. The preparation method of the present invention comprises the following steps: adding non-aromatic chiral molecules containing urea bonds to an organic solvent, heating until clear, and then gradually cooling until a supramolecular assembly with circularly polarized phosphorescent properties is formed, namely, the non-aromatic circularly polarized room temperature phosphorescent material. The present invention utilizes supramolecular assembly of non-aromatic chiral molecules containing urea bonds to impart circularly polarized phosphorescent properties, thereby achieving both the phosphorescent and circular polarization properties of non-aromatic molecules. The preparation method is simple and highly operable.

Description

Technical Field

[0001] The present invention belongs to the field of circularly polarized luminescence, and specifically relates to a non-aromatic circularly polarized room temperature phosphorescent material and its preparation and application. The circularly polarized room temperature phosphorescent material has applications in anti-counterfeiting and optical devices. Background Art

[0002] When excited by incident light, certain chiral materials emit left and right circularly polarized light of varying intensities. This phenomenon, known as circularly polarized luminescence (CPL), also reflects the chirality of the excited state. Circularly polarized luminescence (CPL) materials have broad application prospects in 3D optical displays, optical data storage, anti-counterfeiting, information encryption, and optical devices.

[0003] In recent years, organic room-temperature phosphorescent (RTP) materials have attracted widespread attention from researchers due to their long lifetime and rich excited state properties, and have potential applications in fields such as information encryption, displays, organic light-emitting diodes, and biomedicine. Early research on phosphorescent materials focused on metal-containing compounds, such as europium, iridium, and platinum-containing complexes. Limited new metal resources and high toxicity have hindered their further development. Therefore, metal-free organic phosphorescent materials have received increasing attention. Compared with organometallic compounds, pure organic compounds are challenging due to weak spin-orbit coupling (SOC) and fast non-radiative decay of triplet excitons due to thermal molecular motion and collisions, as well as quenching by oxygen and moisture, which greatly limits their practical applications, especially in the field of biotechnology.

[0004] Circularly polarized room temperature phosphorescent (CP-RTP) materials have broad applications in information encoding, anti-counterfeiting, bioimaging, biotherapy, and optoelectronics. To achieve CP-RTP, chirality and room temperature phosphorescence are prerequisites, and the level of circularly polarized phosphorescence can be evaluated using the luminescence asymmetry factor and the phosphorescence lifetime. Traditional organic materials cannot produce room temperature phosphorescence because they cannot convert the spin-allowed, short-lived singlet excited state into the spin-forbidden, long-lived triplet excited state. Various approaches have been used to impart room temperature phosphorescence to these organic materials, such as by introducing chemical moieties (such as metal ions, aromatic carbon groups, and halogens), stabilizing triplet excitons, suppressing non-radiative relaxation that restricts molecular motion, inert atmospheres, and ultralow temperatures. Currently reported CP-RTP materials are mainly organic room temperature phosphorescent materials of this type, while the research on non-aromatic organic CP-RTP materials is very difficult. Summary of the Invention

[0005] The purpose of the present invention is to provide a non-aromatic circularly polarized room temperature phosphorescent material and its preparation and application. The present invention develops a series of non-aromatic chiral molecules containing urea bonds, which are assembled into a new type of circularly polarized room temperature phosphorescent material. The operation method is simple, the applicability is strong, and the prepared material has a wide range of applications.

[0006] The non-aromatic chiral molecule containing a urea bond provided by the present invention contains a urea bond and a C10-C20 straight-chain or branched alkyl group;

[0007] Specifically, the non-aromatic chiral molecules containing urea bonds are L / D-cystine derivatives, L / D-lysine derivatives, L / D-glutamic acid derivatives, and RR / SS-cyclohexanediamine derivatives containing urea bonds, preferably L / D-lysine derivatives containing urea bonds.

[0008] The non-aromatic chiral molecule containing a urea bond provided by the present invention is prepared by reacting an amino compound containing at least one chiral carbon atom without an aromatic ring with R-isocyanate.

[0009] Wherein, when the amino compound contains two or more chiral carbon atoms, the configurations of the two or more chiral carbon atoms are the same, such as the same R type or the same S type;

[0010] Specifically, the amino compound is selected from at least one of L / D-cystine derivatives, L / D-lysine derivatives, L / D-glutamic acid derivatives, and RR / SS-cyclohexanediamine derivatives, and R in R-isocyanate is a C10-C20 linear or branched alkyl group;

[0011] Alternatively, the non-aromatic chiral molecule containing a urea bond is prepared by reacting N,N'-bis-C10-C20 linear or branched alkyl-L / D-amino-glutamic acid diamide with X-C1-C6 alkyl-isocyanate, wherein X represents a halogen, specifically Cl or Br.

[0012] The non-aromatic chiral molecule containing a urea bond may be any of the following:

[0013]

[0014]

[0015]

[0016] The present invention also provides a non-aromatic circularly polarized room temperature phosphorescent material.

[0017] The non-aromatic circularly polarized room temperature phosphorescent material provided by the present invention is assembled from the above-mentioned non-aromatic chiral molecules containing urea bonds.

[0018] The non-aromatic circularly polarized room temperature phosphorescent material is prepared by a method comprising the following steps:

[0019] The non-aromatic chiral molecule containing a urea bond is added to an organic solvent, heated until clear, and then gradually cooled until a supramolecular assembly is formed, namely, a non-aromatic circularly polarized room temperature phosphorescent material.

[0020] In the above method, the organic solvent includes at least one of tetrahydrofuran, acetone, chloroform, and dichloromethane.

[0021] The concentration of the non-aromatic chiral molecule containing a urea bond in the organic solvent is 3 to 100 mg / ml, specifically 10 to 30 mg / ml, more specifically 10 mg / ml or 30 mg / ml.

[0022] The application of the above-mentioned non-aromatic chiral molecules containing urea bonds and the non-aromatic circularly polarized room temperature phosphorescent materials prepared therefrom in biomedicine, optical information storage and encryption, and optical devices also falls within the scope of protection of the present invention.

[0023] The present invention also provides an application device, which is made of the above-mentioned non-aromatic circularly polarized room temperature phosphorescent material.

[0024] The application device is at least one of an anti-counterfeiting device, a 3D display, OLEDs, a chiral separation film and a photoelectric device.

[0025] In the above method, the raw materials for synthesizing the non-aromatic chiral molecules containing urea bonds are all publicly available materials on the market.

[0026] The present invention has the following advantages:

[0027] (1) The present invention obtains non-aromatic chiral molecules containing urea bonds through simple synthetic steps, and obtains supramolecular assemblies with circularly polarized phosphorescent properties through assembly.

[0028] (2) The present invention prepares the obtained supramolecular assembly into an application device with circularly polarized phosphorescent properties, which has potential applications in anti-counterfeiting, 3D display, etc.

[0029] (3) The preparation method of the present invention has mild conditions, operates at room temperature, has little environmental impact, and is low in cost, which is of great significance for the study of non-aromatic circularly polarized phosphorescent materials.

[0030] The present invention develops a class of non-aromatic circularly polarized room temperature phosphorescent materials and explores their chiral optical properties and application research. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1a18NCO prepared in the present invention is the H NMR spectrum;

[0032] Figure 1b 18NCO prepared in the present invention is the H NMR spectrum;

[0033] Figure 1c CP-RTP luminescence spectra of L-Lys-18NCO and D-Lys-18NCO (excitation = 360 nm) prepared in Example 1 of the present invention;

[0034] Figure 2a 14NCO prepared in the present invention is the H NMR spectrum;

[0035] Figure 2b 14NCO prepared in the present invention is the H NMR spectrum;

[0036] Figure 2c CP-RTP luminescence spectra of L-Lys-14NCO and D-Lys-14NCO (excitation = 360 nm) prepared in Example 2 of the present invention;

[0037] Figure 3a 1H NMR spectrum of L-Lys-12NCO prepared in the examples of the present invention;

[0038] Figure 3b 1 is the H NMR spectrum of D-Lys-12NCO prepared in the examples of the present invention;

[0039] Figure 3c CP-RTP luminescence spectra of L-Lys-12NCO and D-Lys-12NCO (excitation = 360 nm) prepared in Example 3 of the present invention;

[0040] Figure 4a This is the H NMR spectrum of L-Cys-18NCO prepared in the examples of the present invention;

[0041] Figure 4b 1H NMR spectrum of D-Cys-18NCO prepared in the examples of the present invention;

[0042] Figure 4c CP-RTP luminescence spectra of L-Cys-18NCO and D-Cys-18NCO (excitation = 300 nm) prepared in Example 4 of the present invention;

[0043] Figure 5a : This is the H NMR spectrum of R,R-cyclohexanediamine-18NCO prepared in the examples of the present invention;

[0044] Figure 5bThis is the H NMR spectrum of S,S-cyclohexanediamine-18NCO prepared in the examples of the present invention;

[0045] Figure 5c CP-RTP luminescence spectra of R,R-cyclohexanediamine-18NCO and S,S-cyclohexanediamine-18NCO (excitation = 340 nm) prepared in Example 5 of the present invention;

[0046] Figure 6a LG-Cl-NCO prepared in the embodiment of the present invention is the H NMR spectrum;

[0047] Figure 6b : This is the H NMR spectrum of DG-Cl-NCO prepared in the embodiment of the present invention;

[0048] Figure 6c This is the CP-RTP luminescence spectrum of LG-Cl-NCO and DG-Cl-NCO (excitation = 340 nm) prepared in Example 6 of the present invention;

[0049] Figure 7a H NMR spectrum of LG-Br-NCO prepared in the embodiment of the present invention;

[0050] Figure 7b H NMR spectrum of LG-Br-NCO prepared in the embodiment of the present invention;

[0051] Figure 7c This is the CP-RTP luminescence spectrum of LG-Br-NCO and DG-Br-NCO (excitation = 340 nm) prepared in Example 7 of the present invention. DETAILED DESCRIPTION

[0052] The present invention will be further described in detail below in conjunction with specific embodiments. The examples provided are only for illustrating the present invention and are not intended to limit the scope of the present invention. The examples provided below can serve as a guide for further improvements by those skilled in the art and are not intended to limit the present invention in any way.

[0053] Unless otherwise specified, the experimental methods in the following examples are conventional methods and were performed according to the techniques or conditions described in the literature in the field or according to the product instructions. The materials and reagents used in the following examples, unless otherwise specified, were all commercially available.

[0054] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 1 below is as follows:

[0055] 1 mmol of L / D-lysine methyl ester dihydrochloride (purchased from Inochem) and 2.4 mmol of octadecyl isocyanate (purchased from Inochem) were added in a molar ratio of 1:2.4 in 100 mL of CH2Cl2 (dichloromethane, purchased from Sinopharm Group), and 2.4 mmol of TEA (triethylamine, purchased from Sinopharm Group) was added and reacted at room temperature for 48 hours. After the reaction was completed, the product was washed with dichloromethane three times and filtered to obtain L / D-Lys-18NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 1a , 1b.

[0056]

[0057] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 2 below is as follows:

[0058] 1 mmol of L / D-lysine methyl ester dihydrochloride (purchased from Inochem) and 2.4 mmol of tetradecyl isocyanate (purchased from Inochem) were added in a molar ratio of 1:2.4 in 100 mL of CH2Cl2 (dichloromethane, purchased from Sinopharm Group), and 2.4 mmol of TEA (triethylamine, purchased from Sinopharm Group) was added and reacted at room temperature for 48 hours. After the reaction was completed, it was washed with dichloromethane three times and filtered to obtain L / D-Lys-14NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 2a , 2b.

[0059]

[0060]

[0061] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 3 below is as follows:

[0062] 1 mmol of L / D-lysine methyl ester dihydrochloride (purchased from Inochem) and 2.4 mmol of dodecyl isocyanate (purchased from Inochem) were added to 100 mL of CH2Cl2 (dichloromethane, purchased from Sinopharm Group) in a molar ratio of 1:2.4. 2.4 mmol of TEA (triethylamine, purchased from Sinopharm Group) was added and reacted at room temperature for 48 hours. After the reaction was completed, the product was washed with dichloromethane three times and filtered to obtain L / D-Lys-12NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 3a , 3b.

[0063]

[0064] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 4 below is as follows:

[0065] 1 mmol of L / D-cystine methyl ester dihydrochloride (purchased from Inochem) and 2.4 mmol of octadecyl isocyanate (purchased from Inochem) were added to 100 mL of CH2Cl2 (dichloromethane, purchased from Sinopharm Group) in a molar ratio of 1:2.4. 2.4 mmol of TEA (triethylamine, purchased from Sinopharm Group) was added and reacted at room temperature for 48 hours. After the reaction was completed, it was washed with dichloromethane three times and filtered to obtain L / D-Cys-18NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 4a , 4b.

[0066]

[0067]

[0068] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 5 below is as follows:

[0069] 1 mmol of R,R-cyclohexanediamine or S,S-cyclohexanediamine (purchased from Inochem) and 1.2 mmol of octadecyl isocyanate (purchased from Inochem) were reacted in 100 mL of CH2Cl2 (dichloromethane, purchased from Sinopharm Group) at room temperature for 48 hours. After the reaction was completed, the product was washed with dichloromethane three times and filtered to obtain RR / SS-cyclohexanediamine-18NCO (yield 90%) for later use. Structural confirmation data can be found in Figure 5a , 5b.

[0070]

[0071] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 6 below is as follows:

[0072] The synthesis of N,N'-dioctadecyl-L-amino-glutamic acid diamide (LG) and N,N'-dioctadecyl-D-aminoglutamic acid diamide (DG) has been previously reported [Xuefeng Zhu, Yuangang Li, Pengfei Duan* and Minghua Liu*. Self-Assembled Ultralong Chiral Nanotubes and Tuning of Their Chirality through the Mixing of Enantiomeric Components[J]. Chemistry-A European Journal, 2010, 16:8034-8040.]. In this experiment, LG and DG were directly synthesized as raw materials to synthesize the target compounds. The specific synthesis method is as follows.

[0073] LG or DG (2.06 g, 3.00 mmol) was dispersed in chloroform (purchased from Sinopharm Group) solvent. After the mixture was completely dissolved, 2-chloroisocyanate (0.32 g, 3.00 mmol) was slowly added dropwise and reacted at 110°C for 1 hour. After the reaction was completed, it was washed with chloroform three times and filtered to obtain LG-Cl-NCO or DG-Cl-NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 6a , 6b. This molecule is an intermediate of a molecule previously reported in the literature [Changxia Liu, Dong Yang, Li Zhang* and Minghua Liu*. Water-inversed helicity of nanostructures from ionic self-assembly of achiral gelator and an achiral component[J]. SoftMatter, 2019, 15, 6557.]

[0074]

[0075] The preparation method of the non-aromatic chiral molecule containing a urea bond used in Example 7 is as follows:

[0076] The synthesis of N,N'-dioctadecyl-L-amino-glutamic acid diamide (LG) and N,N'-dioctadecyl-D-aminoglutamic acid diamide (DG) has been previously reported [Xuefeng Zhu, Yuangang Li, Pengfei Duan* and Minghua Liu*. Self-Assembled Ultralong Chiral Nanotubes and Tuning of Their Chirality through the Mixing of Enantiomeric Components[J]. Chemistry-A European Journal, 2010, 16:8034-8040.]. In this experiment, LG and DG were directly synthesized as raw materials to synthesize the target compounds. The specific synthesis method is as follows.

[0077] LG or DG (2.06 g, 3.00 mmol) was dispersed in chloroform (purchased from Sinopharm Group) solvent. After the mixture was completely dissolved, 2-bromoisocyanate (0.32 g, 3.00 mmol) was slowly added dropwise and reacted at 110°C for 1 hour. After the reaction was completed, it was washed with chloroform three times and filtered to obtain LG-Br-NCO or DG-Br-NCO (yield 95%) for later use. Structural confirmation data can be found in Figure 7a , 7b.

[0078]

[0079]

[0080] Example 1

[0081] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0082] (1) 30 mg of a non-aromatic chiral molecule L-Lys-18NCO containing a urea bond was added to 1 ml of tetrahydrofuran, an organic solvent, and heated until clear. The temperature was then gradually lowered until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0083] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0084] L-Lys-18NCO was replaced by D-Lys-18NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0085] The supramolecular assembly L / D-Lys-18NCO was excited by light with a wavelength of 360 nm and CPL test was performed. The results are as follows: Figure 1a As shown, the maximum emission wavelength is 430 nm, where L / D-Lys-18NCO can obtain a mirror-symmetrical CPL signal. The lifetime of the supramolecular assembly L / D-Lys-18NCO was tested under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, with lifetimes of 32.4 ms and 25.0 ms, respectively.

[0086] Example 2

[0087] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0088] (1) 30 mg of a non-aromatic chiral molecule L-Lys-14NCO containing a urea bond was added to 1 ml of an organic solvent, tetrahydrofuran, and heated until clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0089] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0090] L-Lys-14NCO was replaced by D-Lys-14NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0091] The supramolecular assembly L / D-Lys-14NCO was excited by light with a wavelength of 360 nm and CPL test was performed. The results are as follows: Figure 2a As shown, the maximum emission wavelength is 430 nm, where L / D-Lys-14NCO can obtain a mirror-symmetrical CPL signal. Under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, the lifetime of the supramolecular assembly L / D-Lys-14NCO was tested, and the lifetimes were 185.64 μs and 185.63 μs, respectively.

[0092] Example 3

[0093] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0094] (1) 30 mg of a non-aromatic chiral molecule L-Lys-12NCO containing a urea bond was added to 1 ml of an organic solvent, tetrahydrofuran, and heated until clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0095] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0096] L-Lys-12NCO was replaced by D-Lys-12NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0097] The supramolecular assembly L / D-Lys-12NCO was excited by light with a wavelength of 360 nm and CPL test was performed. The results are as follows: Figure 3a As shown, the maximum emission wavelength is 430 nm, where L / D-Lys-12NCO can obtain a mirror-symmetrical CPL signal. Under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, the lifetime of the supramolecular assembly L / D-Lys-12NCO was tested, and the lifetimes were 163.30 μs and 156.76 μs, respectively.

[0098] Example 4

[0099] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0100] (1) 10 mg of a non-aromatic chiral molecule L-Cys-18NCO containing a urea bond was added to 1 mL of an organic solvent, acetone, and heated until the solution became clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0101] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0102] L-Cys-18NCO was replaced by D-Cys-18NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0103] The supramolecular assembly L / D-Cys-18NCO was excited by light with a wavelength of 300 nm and CPL test was performed. The results are as follows: Figure 4a As shown, the maximum emission wavelength is 400 nm, where L / D-Cys-18NCO can obtain a mirror-symmetric CPL signal. Under the conditions of excitation wavelength of 300 nm and emission wavelength of 400 nm, the lifetime of the supramolecular assembly L / D-Cys-18NCO was tested, and the lifetimes were 627.70 μs and 594.20 μs, respectively.

[0104] Example 5

[0105] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0106] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, RR-cyclohexanediamine-18NCO, was added to 1 mL of an organic solvent, chloroform, and heated until the solution became clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0107] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0108] The organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions by replacing RR-cyclohexanediamine-18NCO with SS-cyclohexanediamine-18NCO.

[0109] The supramolecular assembly RR / SS-cyclohexanediamine-18NCO was excited by light with a wavelength of 340 nm and CPL test was performed. The results are as follows: Figure 5a As shown, the maximum emission wavelength is 430 nm, where RR / SS-cyclohexanediamine-18NCO can obtain a mirror-symmetrical CPL signal. The lifetime of the supramolecular assembly RR / SS-cyclohexanediamine-18NCO was tested under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, and the lifetimes were 29.89 μs and 30.89 μs, respectively.

[0110] Example 6

[0111] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0112] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, LG-Cl-NCO, was added to 1 mL of an organic solvent, chloroform, and heated until the solution became clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0113] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0114] LG-Cl-NCO was replaced by DG-Cl-NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0115] The supramolecular assembly LG / DG-Cl-NCO was excited by light with a wavelength of 340 nm and the CPL test results were as follows: Figure 6a As shown, the maximum emission wavelength is 430 nm, where LG / DG-Cl-NCO can obtain a mirror-symmetric CPL signal. Under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, the lifetime of the supramolecular assembly LG / DG-Cl-NCO was tested, and the lifetimes were 29.32 μs and 29.91 μs, respectively.

[0116] Example 7

[0117] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0118] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, LG-Br-NCO, was added to 1 mL of an organic solvent, chloroform, and heated until the solution became clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0119] (2) The obtained supramolecular assembly is prepared into an application device, that is, a device with circularly polarized room temperature phosphorescence performance is obtained.

[0120] LG-Br-NCO was replaced by DG-Br-NCO, and the organic material with circularly polarized room temperature phosphorescence was prepared again using the above conditions.

[0121] The supramolecular assembly LG / DG-Br-NCO was excited by light with a wavelength of 340 nm and the CPL test results were as follows: Figure 7a As shown, the maximum emission wavelength is 430 nm, where LG / DG-Br-NCO can obtain a mirror-symmetrical CPL signal. Under the conditions of excitation wavelength of 360 nm and emission wavelength of 430 nm, the lifetime of the supramolecular assembly LG / DG-Br-NCO was tested, and the lifetimes were 18.39 μs and 16.40 μs, respectively.

[0122] Comparative Example 1

[0123] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, LG-Br-NCO, was added to 1 mL of the organic solvent dimethyl sulfoxide, heated until clear, and then gradually cooled until a supramolecular assembly was formed;

[0124] (2) The obtained supramolecular assembly is prepared into an application device.

[0125] The organic material was prepared again using the above conditions, except that LG-Br-NCO was replaced by DG-Br-NCO.

[0126] Light with a wavelength of 340 nm was used as the excitation wavelength to excite the supramolecular assembly LG / DG-Br-NCO. A CPL test was performed, but no CPL signal was found and no light was emitted.

[0127] Comparative Example 2

[0128] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, LG-Cl-NCO, was added to 1 mL of an organic solvent, dimethyl sulfoxide, and heated until the solution became clear. The solution was then gradually cooled until a supramolecular assembly with circularly polarized phosphorescence was formed.

[0129] (2) The obtained supramolecular assembly is prepared into an application device.

[0130] The organic material was prepared again using the above conditions, replacing LG-Cl-NCO with DG-Cl-NCO.

[0131] Light with a wavelength of 340 nm was used as the excitation wavelength to excite the supramolecular assembly LG / DG-Cl-NCO. A CPL test was performed, but no CPL signal was found and no light was emitted.

[0132] Comparative Example 3

[0133] The present invention provides a preparation and application of a non-aromatic circularly polarized room temperature phosphorescent material, comprising the following steps:

[0134] (1) 10 mg of a non-aromatic chiral molecule containing a urea bond, RR-cyclohexanediamine-18NCO, was added to 1 mL of dimethyl sulfoxide (DMSO) as an organic solvent, heated until clear, and then gradually cooled until a supramolecular assembly was formed.

[0135] (2) The obtained supramolecular assembly is prepared into an application device.

[0136] The organic material was prepared again using the above conditions except that RR-cyclohexanediamine-18NCO was replaced by SS-cyclohexanediamine-18NCO.

[0137] Light with a wavelength of 340 nm was used as the excitation wavelength to excite the supramolecular assembly RR / SS-cyclohexanediamine-18NCO. CPL testing was performed, but no CPL signal was found and no luminescence was observed.

[0138] It can be seen from Comparative Examples 1-3 that non-aromatic chiral molecules containing urea bonds need to be supramolecularly assembled in a specific solvent to obtain supramolecular assemblies with circularly polarized phosphorescence properties.

[0139] The present invention has been described in detail above. For those skilled in the art, without departing from the purpose and scope of the present invention, and without the need to carry out unnecessary experimental conditions, the present invention can be implemented in a wide range under equivalent parameters, concentrations and conditions. Although the present invention provides specific embodiments, it should be understood that further improvements can be made to the present invention. In short, according to the principles of the present invention, this application is intended to include any changes, uses or improvements to the present invention, including changes that depart from the disclosed scope in this application and are made using conventional techniques known in the art.

Claims

1. A non-aromatic circularly polarized room temperature phosphorescent material, assembled from non-aromatic chiral molecules containing urea bonds, wherein the non-aromatic chiral molecules containing urea bonds are any of the following: 。 2. A method for preparing the non-aromatic circularly polarized room temperature phosphorescent material according to claim 1, comprising the steps of: adding the non-aromatic chiral molecule containing a urea bond to an organic solvent, heating until clear, and then gradually cooling until a supramolecular assembly is formed, i.e., the non-aromatic circularly polarized room temperature phosphorescent material.

3. The method according to claim 2, wherein: The organic solvent is selected from at least one of tetrahydrofuran, acetone, chloroform and dichloromethane; The concentration of the non-aromatic chiral molecule containing a urea bond in the organic solvent is 3-100 mg / ml.

4. Use of the non-aromatic circularly polarized room temperature phosphorescent material according to claim 1 in optical information storage and encryption, and optical devices. 5 . An application device, wherein the application device is made of the non-aromatic circularly polarized room temperature phosphorescent material according to claim 1 .

6. The application device according to claim 5, characterized in that: The application device is at least one of an anti-counterfeiting device, a 3D display, OLEDs, a chiral separation film and a photoelectric device.

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