Double-component afterglow material capable of being excited from ultraviolet light to red light as well as preparation method and application of double-component afterglow material

Abstract

The invention discloses a two-component afterglow material capable of being excited from ultraviolet light to red light as well as a preparation method and application of the two-component afterglow material. The two-component afterglow material comprises an organic guest luminescent material and a small molecule host material, the organic guest luminescent material is an acenaphthequinone derivative composed of an electron donor and an electron acceptor, and the two-component afterglow material is prepared by doping the organic guest luminescent material into the small molecule host material and heating and melting. The two-component afterglow material has an excitation wavelength in the range from ultraviolet to red light (254 nm to 650 nm) and achieves near-infrared afterglow at 720 nm with a lifetime of more than 50 ms. In addition, the afterglow emission channel can be regulated and controlled by changing the variety of the small molecule host material. The two-component afterglow material has wide-range excitation wavelength and afterglow channel dynamic adjustability, and can be applied to the aspects of photoelectric devices, display materials, anti-counterfeiting materials or imaging materials and the like.

Description

Technical Field

[0001] The present invention relates to the technical field of organic light-emitting materials, and particularly to a red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light, and its preparation method and application. Background Art

[0002] Organic afterglow materials have been widely studied due to their applications in biological imaging, anti-counterfeiting, information encryption, optoelectronic devices, etc. Currently, there are mainly three types of afterglow materials: room-temperature phosphorescence, thermally activated delayed fluorescence, and long persistent luminescence. Although many afterglow systems have been developed, their excitation wavelengths are generally in the ultraviolet region and the emission wavelengths are in the yellow-green region, and the afterglow characteristics are relatively single. Due to the energy gap law of non-radiative transitions, it is difficult to obtain afterglow emission in the near-infrared region. Host-guest dual-component doping is one of the most commonly used strategies for constructing afterglow materials because it has inherent advantages: simplicity, low cost, diversity of host / guest combinations, etc. In traditional host-guest doping systems, Kasha's exciton model and other studies have shown that due to the negligible transition dipole moment of the lowest triplet excited state, the lowest triplet excited state energy level of organic compounds is insensitive to the microenvironment, so the delayed emission peak remains basically unchanged and does not exhibit dynamics.

[0003] Therefore, developing a red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light is both challenging and attractive, and this will help to expand applications in optoelectronic devices, display materials, anti-counterfeiting materials, or imaging materials, etc. Summary of the Invention

[0004] To solve the above technical problems, the present invention provides a dual-component afterglow material that can be excited from ultraviolet to red light, and its preparation method and application. By incorporating an organic guest luminescent material including an acenaphthenequinone derivative into a small molecule host material and preparing it by heating and melting, a red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light is obtained. The dual-component afterglow material has an excitation wavelength in the range from ultraviolet to red light (254 nm - 650 nm), and realizes a near-infrared afterglow with a lifetime exceeding 50 ms at 720 nm. In addition, the afterglow emission channel can be regulated by changing the type of the small molecule host material.

[0005] The specific technical solutions of the present invention include:

[0006] The present invention provides a dual-component afterglow material that can be excited from ultraviolet to red light. The dual-component afterglow material includes an organic guest luminescent material and a small molecule host material. The organic guest luminescent material is an acenaphthenequinone derivative composed of an electron donor and an electron acceptor, wherein the electron acceptor has the structures shown in the following formulas (A-1) to (A-4), and the electron donor has the structures shown in the following formulas (D-1) to (D-3):

[0007]

[0008] wherein R is selected from one of H, C n H (2n+1) and each R is the same as each other.

[0009] In some embodiments of the present invention, the organic guest luminescent material is composed of any combination of the electron donor and the electron acceptor.

[0010] In some embodiments of the present invention, the small molecule host material has the structures shown in formulas (H-1) to (H-4):

[0011]

[0012]

[0013] In some embodiments of the present invention, the weight of the organic guest luminescent material is 0.01% to 10% of the total weight of the two-component afterglow material. In one embodiment, based on the total weight of the two-component afterglow material, the content of the organic guest luminescent material is 0.01 weight percentage.

[0014] In some embodiments of the present invention, the weight of the organic guest luminescent material is 90% to 99.99% of the total weight of the two-component afterglow material.

[0015] In some embodiments of the present invention, the afterglow lifetime of the two-component afterglow material is ≥0.1 ms, the photoluminescence quantum yield of the two-component afterglow material is ≥0.1%, and the delayed emission peak wavelength of the two-component afterglow material is ≥580 nm. In one embodiment, the maximum afterglow lifetime of the two-component afterglow material is 735.87 ms, the highest photoluminescence quantum yield of the two-component afterglow material is 64.8%, and the longest delayed emission peak wavelength of the two-component afterglow material is 725 nm.

[0016] In some embodiments of the present invention, the two-component afterglow material has a broad range of excitation wavelengths from ultraviolet to red light regions. Preferably, the two-component afterglow material has an excitation wavelength, and a range of the excitation wavelength is between 254 nm and 650 nm.

[0017] In some embodiments of the present invention, when the weight of the organic guest luminescent material exceeds 1% of the total weight of the two-component afterglow material, the two-component afterglow material realizes near-infrared afterglow at a wavelength of 720 nm, and the lifetime of the two-component afterglow material exceeds 50 ms. Preferably, based on the total weight of the two-component afterglow material, the content of the organic guest luminescent material is 10 weight percentage.

[0018] In some embodiments of the present invention, when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-3), the afterglow emission channel of the two-component afterglow material is room temperature phosphorescence type, that is, the two-component afterglow material is a room temperature phosphorescence type afterglow material; when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-1) and / or formula (H-2), the afterglow emission channel of the two-component afterglow material is thermally activated delayed fluorescence type, that is, the two-component afterglow material is a room temperature thermally activated delayed fluorescence type afterglow material; and when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-4), the afterglow emission channel of the two-component afterglow material is long persistent luminescence type, that is, the two-component afterglow material is a long persistent luminescence type afterglow material.

[0019] According to the present invention, there is also provided a method for preparing an ultraviolet to red light excitable two-component afterglow material, the preparation method comprising the following steps:

[0020] Step S01: Provide an organic guest luminescent material and a small molecule host material, wherein the organic guest luminescent material is an acenaphthenequinone derivative;

[0021] Step S02: Grind the organic guest luminescent material and the small molecule host material to be fully mixed uniformly to obtain an intermediate mixture;

[0022] Step S03: Heat the intermediate mixture until the intermediate mixture is completely melted, and cool the melted intermediate mixture to obtain the ultraviolet to red light excitable two-component afterglow material.

[0023] The present invention also relates to an application of the above ultraviolet to red light excitable two-component afterglow material, and the two-component afterglow material as described above is applied in optoelectronic devices, display materials, anti-counterfeiting materials or imaging materials.

[0024] The present invention provides an ultraviolet to red light excitable two-component afterglow material and its preparation method and application. The two-component afterglow material includes an organic guest luminescent material and a small molecule host material. The organic guest luminescent material is an acenaphthenequinone derivative, and the acenaphthenequinone derivative is composed of an electron donor and an electron acceptor. The obtained two-component afterglow material has an excitation wavelength in the range from ultraviolet to red light (254 nm - 650 nm), and realizes a near-infrared afterglow with a lifetime exceeding 50 ms at 720 nm. In addition, by changing the type of the small molecule host material, the afterglow emission channel can be regulated to achieve both a wide range of excitation wavelengths and dynamic tunability of the afterglow channel.

[0025] Describe more details and advantages of the present invention with reference to the embodiments shown in the accompanying drawings. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] By way of example only, some embodiments of the present invention are described herein with reference to the accompanying drawings. Now specifically referring in detail to the accompanying drawings, it should be emphasized that the details shown are by way of example and for the purpose of illustrative discussion of the embodiments of the present invention. In this regard, the description in conjunction with the drawings enables those skilled in the art to clearly understand how to implement the embodiments of the present invention.

[0027] In the drawings:

[0028] Figure 1 It is a schematic flow chart of the preparation method of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light according to the present invention.

[0029] Figure 2 It is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 1 of the present invention.

[0030] Figure 3 It is a schematic diagram of the delayed luminescence lifetime decay curve of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 1 of the present invention.

[0031] Figure 4 It is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 2 of the present invention.

[0032] Figure 5 It is a schematic diagram of the delayed luminescence lifetime decay curve of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 2 of the present invention.

[0033] Figure 6 It is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 3 of the present invention.

[0034] Figure 7 It is a schematic diagram of the delayed luminescence lifetime decay curve of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 3 of the present invention.

[0035] Figure 8 It is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 4 of the present invention.

[0036] Figure 9 It is a schematic diagram of the delayed luminescence lifetime decay curve of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Embodiment 4 of the present invention.

[0037] Figure 10 Schematic diagram of afterglow photos of the red / near-infrared dual-component afterglow materials that can be excited from ultraviolet to red light obtained in Embodiments 1 to 4 of the present invention under excitation light sources of different wavelengths. Detailed implementation manners

[0038] The following introduces the detailed implementation manners of the ultraviolet-to-red-light-excitable dual-component afterglow material of the present invention, its preparation method and application in conjunction with the accompanying drawings. It should be noted that the implementation of the present invention is not limited to the following implementation manners. Those skilled in the art can understand the advantages and effects of the present invention from the content disclosed in this specification. The present invention can be implemented or applied through other different specific embodiments, and various details in this specification can also be modified and changed based on different viewpoints and applications without departing from the concept of the present invention. In addition, the accompanying drawings of the present invention are only simple schematic illustrations and are not drawn according to actual sizes. The following implementation manners will further detail the related technical content of the present invention, but the disclosed content is not used to limit the protection scope of the present invention.

[0039] The present invention discloses an ultraviolet-to-red-light-excitable dual-component afterglow material, its preparation method and application. The dual-component afterglow material includes an organic guest luminescent material and a small molecule host material. The organic guest luminescent material is an acenaphthenequinone derivative composed of an electron donor and an electron acceptor. Among them, the electron acceptor has the structures shown in the following formulas (A-1) to (A-4), and the electron donor has the structures shown in the following formulas (D-1) to (D-3):

[0040]

[0041] Wherein R is selected from one of H, C n H (2n+1) and each R is the same as each other.

[0042] In one embodiment, the organic guest luminescent material is arbitrarily combined by the electron donor and the electron acceptor.

[0043] In one embodiment, the small molecule host material has the structures shown in formulas (H-1) to (H-4):

[0044]

[0045] In one embodiment, the weight of the organic guest luminescent material is 0.01% to 10% of the total weight of the dual-component afterglow material. Preferably, based on the total weight of the dual-component afterglow material, the content of the organic guest luminescent material is 0.01 weight percentage.

[0046] In some embodiments of the present invention, the weight of the organic guest luminescent material is 90% to 99.99% of the total weight of the two-component afterglow material.

[0047] In some embodiments of the present invention, the afterglow lifetime of the two-component afterglow material ≥ 0.1 ms, the photoluminescence quantum yield of the two-component afterglow material is ≥ 0.1%, and the delayed emission peak wavelength of the two-component afterglow material ≥ 580 nm. Preferably, the maximum afterglow lifetime of the two-component afterglow material is 735.87 ms, the highest photoluminescence quantum yield of the two-component afterglow material is 64.8%, and the longest delayed emission peak wavelength of the two-component afterglow material is 725 nm.

[0048] In some embodiments of the present invention, the two-component afterglow material has a broad range of excitation wavelengths from ultraviolet to red light regions. Preferably, the two-component afterglow material has an excitation wavelength, and a range of the excitation wavelength is between 254 nm and 650 nm.

[0049] In some embodiments of the present invention, when the weight of the organic guest luminescent material exceeds 1% of the total weight of the two-component afterglow material, the two-component afterglow material achieves near-infrared afterglow at a wavelength of 720 nm, and the lifetime of the two-component afterglow material exceeds 50 ms. Preferably, based on the total weight of the two-component afterglow material, the content of the organic guest luminescent material is 10 weight percentages.

[0050] In one embodiment, when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-3), the afterglow emission channel of the two-component afterglow material is room temperature phosphorescence type, that is, the two-component afterglow material is a room temperature phosphorescence type afterglow material.

[0051] In one embodiment, when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-1) and / or formula (H-2), the afterglow emission channel of the two-component afterglow material is thermally activated delayed fluorescence type, that is, the two-component afterglow material is a room temperature thermally activated delayed fluorescence type afterglow material.

[0052] In one embodiment, when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-4), the afterglow emission channel of the two-component afterglow material is long persistent luminescence type, that is, the two-component afterglow material is a long persistent luminescence type afterglow material.

[0053] Please refer to Figure 1 , Figure 1Flow schematic diagram of a preparation method for a red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light. The present invention provides a preparation method for a dual-component afterglow material that can be excited from ultraviolet to red light, and the preparation method includes the following steps:

[0054] Step S01: Provide an organic guest luminescent material and a small molecule host material, wherein the organic guest luminescent material is an acenaphthenequinone derivative;

[0055] Step S02: Grind and mix the organic guest luminescent material and the small molecule host material thoroughly to obtain an intermediate mixture;

[0056] Step S03: Heat the intermediate mixture until the intermediate mixture is completely melted, and cool the melted intermediate mixture to obtain the dual-component afterglow material that can be excited from ultraviolet to red light.

[0057] Incidentally, host-guest material chemistry is a branch of supramolecular chemistry, in which host material molecules bind to guest material molecules or ions. One molecule (host material) provides a suitable cavity or space to accommodate another molecule (guest material). The two components of the complex interact through non-covalent forces (most commonly hydrogen bonding). The binding between the host material and the guest material may be highly selective. In this case, host-guest material chemistry can be imagined as a key and lock relationship: the host material molecule is the lock, and the guest material molecule is the key, and only the correct key can perfectly match the lock.

[0058] As used herein, the term "host material" generally refers to a material molecule with a specific shape or structure that can form a cavity or hole to accommodate guest material molecules.

[0059] As used herein, the term "guest material" refers to a molecule that can be embedded in the cavity or hole of the host material molecule. The guest material binds to the host material through non-covalent interactions.

[0060] Therefore, the present invention also relates to an application of the above dual-component afterglow material that can be excited from ultraviolet to red light, and the dual-component afterglow material as described above is applied in optoelectronic devices, display materials, anti-counterfeiting materials or imaging materials.

[0061] The following examples are listed to more specifically illustrate the present invention. However, the present invention is not limited by the following examples and can be appropriately modified and implemented within the scope of the gist of the present invention, and any of them is included in the technical scope of the present invention.

[0062] Example 1

[0063] The red / near-infrared dual-component afterglow material provided in this embodiment, which can be excited from ultraviolet to red light, comprises a host material (H-1) and organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3). The host material (H-1) is directly purchased from a reagent company. Taking the synthesis of an organic guest luminescent material composed of an electron acceptor (A-1) and an electron donor (D-1) (where R is H and each R is the same as each other) as an example, the specific steps for preparing the organic guest luminescent material are as follows:

[0064]

[0065] 5-Bromoacenaphthenequinone (2 g, 7.66 mmol), N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.27 g, 9.20 mmol), potassium carbonate (3.17 g, 23 mmol) and tetrakis(triphenylphosphine)palladium (383 mg, 0.38 mmol) were added to 1,4-dioxane (100 mL) solvent and deionized water (25 mL). The reaction mixture was stirred overnight at 120 °C under a nitrogen atmosphere. The reactants were quenched with water, extracted with dichloromethane, dried over magnesium sulfate, filtered, concentrated, and purified by silica gel column chromatography (DCM:PE = 3:1) to obtain 1.56 g of an intermediate product (dark red solid), yield: 67.7%.

[0066] 1 g (3.32 mmol) of the intermediate product and 359 mg (3.32 mmol) of diaminomaleonitrile anhydride were dissolved in acetic acid (80 mL). The reaction mixture was stirred overnight at 115 °C under a nitrogen atmosphere. The reactants were quenched with water, and the product was obtained by filtration and purified by column chromatography on silica gel (DCM:MeOH = 50:1) to obtain the guest compound (dark purple solid, 1.04 g), yield: 84.0%.

[0067] The specific method for the dual-component afterglow material provided in this embodiment, which can be excited from ultraviolet to red light, is as follows:

[0068] Please refer to Figure 2 、 Figure 3 and Figure 10 , Figure 2 which is a schematic diagram of the transient and delayed luminescence spectra of the red / near-infrared dual-component afterglow material obtained in Example 1 of the present invention, which can be excited from ultraviolet to red light, Figure 3 which is a schematic diagram of the decay curve of the delayed luminescence lifetime of the red / near-infrared dual-component afterglow material obtained in Example 1 of the present invention, which can be excited from ultraviolet to red light, Figure 10Schematic diagram of afterglow photos of the red / near-infrared dual-component afterglow materials that can be excited from ultraviolet to red light obtained in Embodiments 1 to 4 of the present invention under excitation light sources of different wavelengths. The small molecule host material (H-1) and the organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3) (where the mass ratio of the host material (H-1) to the organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3) is 999:1) are ground evenly using a mortar to obtain an intermediate mixture (mixed powder). The obtained intermediate mixture (mixed powder) is placed on a hot plate and heated to complete melting under air conditions and then cooled to obtain the dual-component afterglow material. The delayed emission spectrum of the dual-component afterglow material is as Figure 2 shown, the maximum emission wavelength is 625 nm, and the decay curve of the delayed emission lifetime is as Figure 3 shown, the luminescence lifetime is 100.32 ms, and the photoluminescence quantum yield is 15.3%. The afterglow photos are as Figure 10 shown, and orange-red afterglow can be produced under excitation from ultraviolet light to yellow light.

[0069] Example 2

[0070] The dual-component afterglow material that can be excited from ultraviolet to red light provided in this example includes a small molecule host material (H-2) and organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3). The small molecule host material (H-2) is directly purchased from a reagent company, and the specific synthesis and preparation method of the organic guest luminescent materials is the same as that in Example 1, and will not be elaborated here. The specific method for the dual-component afterglow material that can be excited from ultraviolet to red light provided in this example is as follows:

[0071] Please refer to Figure 4 、 Figure 5 and Figure 10 , Figure 4 which is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Example 2 of the present invention, Figure 5 which is a schematic diagram of the decay curve of the delayed luminescence lifetime of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in Example 2 of the present invention. The small molecule host material (H-2) and the organic guest luminescent materials (where the mass ratio of the small molecule host material (H-2) to the organic guest luminescent materials is 999:1) are ground evenly using a mortar to obtain an intermediate mixture (mixed powder). The obtained intermediate mixture (mixed powder) is placed on a hot plate and heated to complete melting under air conditions and then cooled to obtain the dual-component afterglow material. Its delayed emission spectrum is as Figure 4 shown, the maximum emission wavelength is 670 nm, and the decay curve of the delayed emission lifetime is asFigure 5 As shown, the luminescence lifetime is 47.82 ms and the photoluminescence quantum yield is 12.3%. The afterglow photograph is as Figure 10 shown, and deep red afterglow can be generated under the excitation from ultraviolet light to yellow light.

[0072] Example 3

[0073] The two-component afterglow material with ultraviolet-to-red light excitable provided in this example includes a small molecule host material (H-3) and organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3). The small molecule host material (H-3) is directly purchased from a reagent company. The specific synthesis method of the organic guest luminescent materials is the same as that in Example 1 and will not be elaborated here. The specific method for the two-component afterglow material with ultraviolet-to-red light excitable provided in this example is as follows:

[0074] Please refer to Figure 6 、 Figure 7 and Figure 10 , Figure 6 which is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared two-component afterglow material with ultraviolet-to-red light excitable obtained in Example 3 of the present invention, Figure 7 and which is a schematic diagram of the delayed luminescence lifetime decay curve of the red / near-infrared two-component afterglow material with ultraviolet-to-red light excitable obtained in Example 3 of the present invention. Mix the small molecule host material (H-3) and the organic guest luminescent materials (where the mass ratio of the small molecule host material (H-3) to the organic guest luminescent materials is 999:1), and use a mortar to grind the small molecule host material and the organic guest luminescent materials evenly to obtain an intermediate mixture (mixed powder). Place the obtained intermediate mixture (mixed powder) on a hot plate and heat it to complete melting under air conditions and then cool it to obtain the two-component afterglow material. Its delayed emission spectrum is as Figure 6 shown, the maximum emission wavelength is 580 nm, and the delayed emission lifetime decay curve is as Figure 7 shown, the luminescence lifetime is 735.87 ms, and the photoluminescence quantum yield is 11.0%. The afterglow photograph is as Figure 10 shown, and orange-yellow afterglow can be generated under the excitation from ultraviolet light to yellow light.

[0075] Example 4

[0076] The two-component afterglow material with ultraviolet-to-red light excitable provided in this example includes a small molecule host material (H-4) and organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3). The small molecule host material (H-4) is directly purchased from a reagent company. The specific synthesis method of the organic guest luminescent materials is the same as that in Example 1 and will not be elaborated here. The specific method for the two-component afterglow material with ultraviolet-to-red light excitable provided in this example is as follows:

[0077] Please also refer to Figure 8 、 Figure 9 and Figure 10 , Figure 8 which is a schematic diagram of the instantaneous and delayed luminescence spectra of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in the fourth embodiment of the present invention, Figure 9 and is a schematic diagram of the decay curve of the delayed luminescence lifetime of the red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light obtained in the fourth embodiment of the present invention. The small molecule host material (H-4) and the organic guest luminescent material (where the mass ratio of the small molecule host material (H-4) to the organic guest luminescent material is 999:1) are ground evenly using a mortar to obtain an intermediate mixture (mixed powder). The obtained intermediate mixture (mixed powder) is placed on a hot plate and heated to complete melting under air conditions and then cooled to obtain a dual-component afterglow material. Its delayed emission spectrum is as shown in Figure 8 shown, the maximum emission wavelength is 650 nm, and the decay curve of the delayed emission lifetime is as shown in Figure 9 shown, the luminescence lifetime is 18.22 ms, and the photoluminescence quantum yield is 64.8%. The afterglow photo is as shown in Figure 10 shown, and red afterglow can be generated under the excitation of ultraviolet light to yellow light.

[0078] Example 5

[0079] The red / near-infrared dual-component afterglow material that can be excited from ultraviolet to red light provided in this example includes a small molecule host material (H-1) and organic guest luminescent materials (A-1) to (A4), (D-1) to (D-3). The host material (H-1) is directly purchased from a reagent company, and the specific synthesis method of the organic guest luminescent material is the same as that in Example 1 and will not be elaborated here. The specific method for the dual-component afterglow material that can be excited from ultraviolet to red light provided in this example is as follows:

[0080] The small molecule host material (H-1) and the organic guest luminescent material (where the mass ratio of the small molecule host material (H-1) to the organic guest luminescent material is 90:10) are ground evenly using a mortar to obtain an intermediate mixture (mixed powder). The obtained intermediate mixture (mixed powder) is placed on a hot plate and heated to complete melting under air conditions and then cooled to obtain a dual-component afterglow material. The maximum emission wavelength of the dual-component afterglow material is 720 nm, the luminescence lifetime is 67.52 ms, and the photoluminescence quantum yield is 10.4%.

[0081] The present invention provides a two-component afterglow material that can be excited from ultraviolet to red light, and a preparation method and application thereof. The two-component afterglow material includes an organic guest luminescent material and a small molecule host material. The organic guest luminescent material is an acenaphthenequinone derivative, and the acenaphthenequinone derivative is composed of an electron donor and an electron acceptor. The obtained two-component afterglow material has an excitation wavelength in the range from ultraviolet to red light (254 nm to 650 nm), and realizes a near-infrared afterglow with a lifetime exceeding 50 ms at 720 nm. In addition, by changing the type of the small molecule host material, the afterglow emission channel can be regulated, realizing both a wide range of excitation wavelengths and dynamic tunability of the afterglow channel.

[0082] Although the present invention has been disclosed above in the foregoing preferred embodiments, it is not intended to limit the present invention. Any person skilled in the art, without departing from the spirit and scope of the present invention, may make some changes and modifications. Therefore, the scope of patent protection of the present invention shall be determined by the scope of the patent application attached to this specification. The present invention is not limited to any of the above embodiments or features. The present invention may include various additions or modifications to the described embodiments.

Claims

1. A two-component afterglow material that can be excited from ultraviolet to red light, characterized in that: The two-component afterglow material includes an organic guest luminescent material and a small molecule host material. The organic guest luminescent material is an acenaphthenequinone derivative composed of an electron donor and an electron acceptor. Among them, the electron acceptor has the structures shown in the following formulas (A-1) to (A-4), and the electron donor has the structures shown in the following formulas (D-1) to (D-3): wherein R is selected from H or C n H (2n+1) and each R is the same as one another.

2. The two-component afterglow material according to claim 1, characterized in that: The small molecule host material has the structures shown in the following formulas (H-1) to (H-4):

3. The two-component afterglow material according to claim 1, characterized in that: The weight of the organic guest luminescent material is 0.01% to 10% of the total weight of the two-component afterglow material.

4. The two-component afterglow material according to claim 1, characterized in that: The weight of the organic guest luminescent material is 90% to 99.99% of the total weight of the two-component afterglow material.

5. The two-component afterglow material according to any one of claims 1 to 3, characterized in that: The afterglow lifetime of the two-component afterglow material is ≥0.1 ms, the photoluminescence quantum yield of the two-component afterglow material is ≥0.1%, and the wavelength of the delayed emission peak of the two-component afterglow material is ≥580 nm.

6. The two-component afterglow material according to any one of claims 1 to 3, characterized in that: The two-component afterglow material has an excitation wavelength, and a range of the excitation wavelength is between 254 nm and 650 nm.

7. The two-component afterglow material according to claim 1, characterized in that: When the weight of the organic guest luminescent material exceeds 1% of the total weight of the two-component afterglow material, the two-component afterglow material achieves near-infrared afterglow at a wavelength of 720 nm, and the lifetime of the two-component afterglow material exceeds 50 ms.

8. The two-component afterglow material according to claim 2, wherein: When the organic guest luminescent material is incorporated into the small molecule host material of formula (H-3), the afterglow emission channel of the two-component afterglow material is room temperature phosphorescence type; when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-1) and / or formula (H-2), the afterglow emission channel of the two-component afterglow material is thermally activated delayed fluorescence type; and when the organic guest luminescent material is incorporated into the small molecule host material of formula (H-4), the afterglow emission channel of the two-component afterglow material is long persistent luminescence type.

9. A preparation method of an ultraviolet-to-red-light-excitable two-component afterglow material, characterized in that: The preparation method includes the following steps: Step S01: Provide an organic guest luminescent material and a small molecule host material, where the organic guest luminescent material is an acenaphthenequinone derivative; Step S02: Grind and fully mix the organic guest luminescent material and the small molecule host material evenly to obtain an intermediate mixture; Step S03: Heat the intermediate mixture until the intermediate mixture completely melts, and cool the melted intermediate mixture to obtain the ultraviolet to red light excitable two-component afterglow material.

10. An application of the two-component afterglow material according to any one of claims 1 to 3 in optoelectronic devices, display materials, anti-counterfeiting materials or imaging materials.

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