Light conversion agent, adhesive film composition, wavelength conversion adhesive film and photovoltaic module

Abstract

The invention provides a light conversion agent, an adhesive film composition, a wavelength conversion adhesive film and a photovoltaic module. The chemical structural formula of the light conversion agent is at least one of formulas I-IV. The imidazole derivative with the specific structure is used as the light conversion agent, has good absorption in an ultraviolet region, is wide in range, almost has no absorption in a visible region, has good visible light permeability, and can better meet the difference requirements of different types of photovoltaic devices on wavelength conversion adhesive films, and the main absorption part is more than 350nm. Furthermore, the light conversion agent has very high absolute light-emitting quantum efficiency, the emission wavelength is basically larger than 430 nm, and the wavelength converted by the light conversion agent can be better utilized by a photovoltaic device.

Description

Technical Field

[0001] The present invention relates to the field of optoelectronic technology, and in particular to a light conversion agent, an adhesive film composition, a wavelength conversion adhesive film and a photovoltaic module. Background Art

[0002] Wavelength conversion films have the ability to convert light (primarily ultraviolet light) that cannot be absorbed by photovoltaic devices into usable visible light. This property allows wavelength conversion films to not only effectively prevent damage to photovoltaic devices caused by high-energy ultraviolet light, but also promote the use of solar energy by photovoltaic devices, thereby improving their photoelectric conversion efficiency. The wavelength conversion function of wavelength conversion films mainly comes from the light converter doped with them. Currently, commonly used light converters can be divided into two types: inorganic and organic. Compared with mature inorganic light converters, there are still few types of high-performance organic light converters. However, the good compatibility and dispersibility of organic light converters in adhesive films, as well as their advantages such as easy synthesis and performance modification, make them show better application potential in the field of light conversion adhesive films.

[0003] Organic small molecule luminescent materials are generally small organic molecules containing large conjugated groups. They possess high luminescence efficiency, long lifespan, a wide variety of materials, and ease of synthesis. Among them, the imidazole group, as the most classic molecular building block of organic optoelectronic functional materials, is commonly used to develop organic small molecules with high stability and high luminescence performance. Therefore, screening and designing stable, highly luminescent organic small molecules based on the imidazole group is a promising approach for developing high-performance organic light conversion agents.

[0004] Currently, light-converting agents and wavelength-converting films based on benzotriazole derivatives have been reported. Compared with previous organic light-converting agents, these light-converting agents have significantly improved photostability and have great application potential.

[0005] The wavelength conversion films commonly found on the market today mostly have a maximum UV absorption value fixed at around 345nm, and the effective absorption range is not large enough, with the maximum emission fixed at around 410nm, which cannot meet the diverse needs of photovoltaic devices produced by different manufacturers. To fully function, wavelength conversion films need to have a sufficiently wide UV absorption range, and the stronger the absorption capacity, the better. Furthermore, in terms of the converted wavelength (i.e., the maximum emission wavelength of the light converter), although photovoltaic devices can actually utilize visible light around 410nm, the utilization efficiency is still low. Generally, for light with a wavelength above 450nm, the utilization rate of photovoltaic devices can reach over 90%. Therefore, the closer the emission of the light converter is to 450nm, the better.

[0006] In summary, although the existing technology has made improvements in photostability, its performance in ultraviolet absorption and light conversion still needs to be improved. Summary of the Invention

[0007] The main purpose of the present invention is to provide a light conversion agent, a film composition, a wavelength conversion film and a photovoltaic module to solve the problem that the effective wavelength absorption range of photovoltaic modules in the prior art is relatively low, making it difficult to effectively utilize visible light.

[0008] In order to achieve the above object, according to one aspect of the present invention, a light conversion agent is provided, wherein the chemical structure of the light conversion agent is at least one of Formula I to Formula IV:

[0009]

[0010]

[0011] Where R a 、R b Each independently selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 hydroxyl groups;

[0012] R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 hydroxyl groups;

[0013] R2 is selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 Aryl, substituted or unsubstituted C6~C 40 heteroaryl, substituted or unsubstituted arylamine, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 of hydroxyl groups.

[0014] Furthermore, R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Ester group, substituted or unsubstituted C6~C 40 The aromatic group,

[0015] Preferably, R1 is selected from R3 is selected from H, C1~C 10 Alkyl, substituted or unsubstituted C1~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Any one of an ester group and a substituted or unsubstituted C0-C8 amine group.

[0016] Further, R2 is selected from Any one of the formula, wherein R4 and R5 are independently selected from H, C1 to C 10 Alkyl, C2~C 10 Ester group, C2~C 10 Alkenyl, C1~C 10Any one of an amide group and a C0-C8 amino group; R6 is selected from a methylene group, one or more hydrogen atoms of which are replaced by C1-C 10 Any one of an alkyl-substituted methylene, a single bond, O and S;

[0017] Preferably, R a 、R b Each independently selected from H, C1-C 10 Alkyl, C2~C 10 Alkenyl, C6~C 20 Aryl, C4~C 20 Heteroaryl, C1~C 10 amino, C1~C 10 Amide group, C3~C 10 Cyclic imide, C1~C 10 Alkoxy, C1~C 10 Carboxyl, C2~C 10 The ester group and C0~C 10 of hydroxyl groups.

[0018] Furthermore, the light conversion agent is any one of the structures shown below:

[0019]

[0020]

[0021] Preferably, in the formula, R3 is selected from H, C1-C8 alkyl, C2-C8 alkenyl, C2-C 10 The ester group, R4, R5 are each independently selected from H, C1 ~ C8 alkyl, C2 ~ C8 alkenyl, C2 ~ C 10 ester group.

[0022] According to another aspect of the present application, a film composition is provided, comprising a base resin and a light conversion agent, wherein the light conversion agent is any one of the light conversion agents described above.

[0023] Furthermore, the light conversion agent accounts for 0.01 to 5% by weight of the film composition, preferably 0.01 to 1.5%.

[0024] Furthermore, the matrix resin includes any one or more of EVA, PVA, PMMA, POE and silicone.

[0025] Furthermore, the film composition further includes an auxiliary agent, which includes any one or a combination of at least two of a cross-linking agent, a co-cross-linking agent, a silane coupling agent, a light stabilizer and an inorganic powder.

[0026] According to another aspect of the present application, a wavelength conversion film is provided, which is prepared by mixing, melt extruding and molding a film composition, wherein the film composition is any one of the above-mentioned film compositions.

[0027] According to another aspect of the present application, a photovoltaic module is provided, comprising a wavelength conversion adhesive film, wherein the wavelength conversion adhesive film is the wavelength conversion adhesive film described above.

[0028] The technical solution of the present invention employs the aforementioned imidazole derivative as a light conversion agent. This agent exhibits strong absorption across a wide range in the ultraviolet region, primarily above 350nm, with virtually no absorption in the visible region. This excellent visible light transmittance can better meet the diverse wavelength conversion film requirements of various photovoltaic devices. Furthermore, this light conversion agent exhibits a high absolute luminous quantum efficiency, with emission wavelengths generally exceeding 430nm, enabling the converted wavelengths to be better utilized by photovoltaic devices. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] The accompanying drawings, which constitute part of this application, are intended to provide a further understanding of the present invention. The exemplary embodiments of the present invention and their descriptions are intended to explain the present invention and do not constitute an undue limitation of the present invention. In the accompanying drawings:

[0030] Figure 1 shows the absorption curve of the wavelength conversion adhesive film according to Example 1 of the present invention;

[0031] Figure 2 shows the emission curve of the wavelength conversion adhesive film according to Example 1 of the present invention;

[0032] Figure 3 shows the absorption curve of the wavelength conversion adhesive film according to Example 2 of the present invention;

[0033] Figure 4 The emission curve of the wavelength conversion adhesive film according to Example 2 of the present invention is shown. DETAILED DESCRIPTION

[0034] It should be noted that, in the absence of conflict, the embodiments and features of the embodiments in this application can be combined with each other. The present invention will be described in detail below with reference to the accompanying drawings and in combination with the embodiments.

[0035] In the present application, the term "substituted or unsubstituted" refers to substitution by one or more substituents selected from the group consisting of deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, or a heterocyclic group containing at least one of N, O, and S, or no substituent, or substituted by a substituent in which two or more substituents are linked together among the exemplified substituents, or no substituent. For example, the term "substituent in which two or more substituents are linked together" may refer to a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are linked together.

[0036] As analyzed in the background of this application, existing photovoltaic modules have a low effective wavelength absorption range, making it difficult to effectively utilize visible light. To address this problem, this application provides a light conversion agent, a film composition, a wavelength conversion film, and a photovoltaic module.

[0037] According to a typical embodiment of the present application, a light conversion agent is provided, wherein the chemical structure of the light conversion agent is at least one of Formula I to Formula IV:

[0038]

[0039]

[0040] Where R a 、R b Each independently selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 hydroxyl groups;

[0041] R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 hydroxyl groups;

[0042] R2 is selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 Aryl, substituted or unsubstituted C6~C 40 heteroaryl, substituted or unsubstituted arylamine, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl, substituted or unsubstituted C0~C 20 of hydroxyl groups.

[0043] This application utilizes the aforementioned imidazole derivatives of specific structures as light conversion agents. These agents exhibit strong, broad absorption in the ultraviolet region, primarily above 350nm, with virtually no absorption in the visible region. This excellent visible light transmittance allows them to meet the diverse wavelength conversion film requirements of various photovoltaic devices. Furthermore, these light conversion agents exhibit a high absolute luminous quantum efficiency, with emission wavelengths generally exceeding 430nm, enabling the converted wavelengths to be better utilized by photovoltaic devices.

[0044] In some preferred embodiments of the present application, in order to further improve the absorption intensity and luminescence ability of the light conversion agent to visible light, in the chemical structure of the light conversion agent, R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Ester group, substituted or unsubstituted C6~C 40 Preferably, R1 is selected from R3 is selected from H, C1~C 10 Alkyl, substituted or unsubstituted C1~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Any one of an ester group and a substituted or unsubstituted C0-C8 amine group.

[0045] In some preferred embodiments of the present application, R2 is selected from Any one of the formula, wherein R4 and R5 are independently selected from H, C1 to C 10 Alkyl, C2~C 10 Any one of an ester group and a C0-C8 amino group; R6 is selected from a methylene group, one or more hydrogens of which are replaced by C1-C 10 Any one of a methylene group substituted with an alkyl group, a single bond, O and S.

[0046] In some preferred embodiments of the present application, R a 、R b Each independently selected from H, C1-C 10 Alkyl, C2~C 10 Alkenyl, C6~C 20 Aryl, C4~C 20 Heteroaryl, C1~C 10 amino, C1~C 10 Amide group, C3~C 10 Cyclic imide, C1~C 10 Alkoxy, C1~C 10 Carboxyl, C2~C10 The ester group and C0~C 10 The hydroxyl group of the compound with the corresponding structure has a better effect as a light conversion agent.

[0047] In some typical embodiments of the present application, when the light conversion agent is any one of the structures shown below, the wavelength conversion film based thereon has stronger absorption capacity and higher luminous efficiency, wherein R3 is selected from H, C1-C8 alkyl, C2-C8 alkenyl, R4 and R5 are each independently selected from H, C1-C8 alkyl, C2-C8 alkenyl, C2-C 10 ester group.

[0048]

[0049] The light-converting agent having the above structure can be synthesized by the method in the prior art, and the present application has no limitation thereto. a and R b Each is H, R2 is Taking the compound as an example, the following chemical formula can be used for synthesis:

[0050]

[0051] With a structure of formula I, and R a and R b Each is H, R2 is Taking the compound as an example, the following chemical formula can be used for synthesis:

[0052]

[0053] According to another typical embodiment of the present application, the present application provides a film composition comprising a base resin and a light-converting agent, wherein the light-converting agent is any one of the light-converting agents described above.

[0054] Because this film composition utilizes the aforementioned imidazole derivative as a light conversion agent, it exhibits strong absorption across a wide range in the ultraviolet region, primarily above 350nm, with virtually no absorption in the visible region. This excellent visible light transmittance allows it to better meet the diverse wavelength conversion film requirements of various photovoltaic devices. Furthermore, due to the high absolute luminous quantum efficiency of the light conversion agent, the film formed from this composition exhibits an emission wavelength substantially greater than 430nm, enabling the converted wavelength to be better utilized by photovoltaic devices.

[0055] In some embodiments of the present application, in order to better exert the effect of the light conversion agent, the light conversion agent accounts for 0.01% to 5% by weight of the film composition, preferably 0.01% to 1.5%.

[0056] Calculated by weight percentage, the light conversion film composition includes 85% to 99.98% of a base resin, 0.01% to 5% of a light conversion agent, and 0.01% to 10% of an auxiliary agent, wherein the light conversion agent is the light conversion agent mentioned above.

[0057] The type of the above-mentioned base resin can be selected from the existing technology and is not particularly limited in this application. In some embodiments of the present application, in order to better play the synergistic effect of the base resin and the light conversion agent, the base resin includes any one or more of EVA, PVA, PMMA, POE and silicone.

[0058] Depending on the specific application environment of the adhesive film, the above-mentioned adhesive film composition may also include additives to further improve the corresponding performance of the adhesive film composition. The specific types and amounts of the additives can be referred to in the prior art. In some embodiments of the present application, the additives include any one or a combination of at least two of a crosslinking agent, a co-crosslinking agent, a silane coupling agent, a tackifying agent, a light stabilizer, or an inorganic powder. The above-mentioned main crosslinking agent, co-crosslinking agent, silane coupling agent, light stabilizer, and inorganic powder can be selected from the prior art.

[0059] The addition of a crosslinking agent helps increase the crosslinking rate of the crosslinked encapsulating film; the addition of a silane coupling agent helps improve the interfacial interaction between the co-crosslinking agent and the matrix resin, thereby enhancing the mechanical properties of the crosslinked encapsulating film. Furthermore, the preferred additives mentioned above help enhance their synergistic effect with the light-converting agent, thereby helping to strengthen the compatibility of the light-converting agent with the matrix resin. They also help increase the overall crosslinking density of the light-converting agent, thereby improving the performance of the light-converting film.

[0060] In one embodiment of the present application, the preferred cross-linking agent is selected from any one or more of tert-butyl peroxy isopropyl carbonate, 2,5-dimethyl 2,5-bis(tert-butylperoxy)hexane, 1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, tert-butyl peroxy carbonate-2-ethylhexyl ester, 2,5-dimethyl 2,5-bis(tert-butylperoxy)hexane, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-amylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-amylperoxy)cyclohexane, 2,2-bis(tert-butylperoxy)butane, tert-amyl peroxy carbonate, and tert-butyl peroxy-3,3,5-trimethylhexanoate.

[0061] In one embodiment of the present application, the preferred co-crosslinking agent is selected from pentaerythritol triacrylate, pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetraacrylate, propoxylated pentaerythritol tetraacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propoxylated trimethylolpropane triacrylate, ethoxylated glycerol triacrylate, propoxylated glycerol triacrylate, trimethylolpropane trimethacrylate, ethoxylated trimethylolpropane trimethacrylate, triethylene glycol dimethacrylate, diethylene glycol dimethacrylate. Any one or more of acrylate, ethylene glycol dimethacrylate, polyethylene glycol (200) diacrylate, polyethylene glycol (400) diacrylate, polyethylene glycol (600) diacrylate, polyethylene glycol (200) dimethacrylate, polyethylene glycol (400) dimethacrylate, polyethylene glycol (600) dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, and neopentyl glycol diacrylate.

[0062] In one embodiment of the present application, the preferred silane coupling agent is selected from any one or more of vinyltrimethoxysilane, vinyltriethoxysilane, γ-methacryloxypropyltrimethoxysilane, 3-(2,3-epoxypropoxy)propyltrimethoxysilane, methacrylate silane, and vinyltriisopropoxysilane.

[0063] In one embodiment of the present application, the preferred light stabilizer is selected from any one or more of bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl) sebacate, poly(4-hydroxy-2,2,6,6-tetramethyl-1-piperidinethanol) succinate, 2-hydroxy-4-n-octyloxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-2′-carboxybenzophenone, and 2,4-dihydroxybenzophenone.

[0064] In one embodiment of the present application, the preferred inorganic powder is selected from any one or more of magnesium hydroxide, magnesium oxide, titanium dioxide, etc.

[0065] According to another typical embodiment of the present application, a wavelength-converting film is provided, prepared by mixing and forming a film composition, wherein the film composition is any of the above-described film compositions. Because the wavelength-converting film is prepared using the above-described film composition containing a light-converting agent with the specific structure of the present application, it exhibits good absorption in the ultraviolet region over a wide range, with the primary absorption portion above 350nm, and virtually no absorption in the visible region. This film exhibits excellent visible light transmittance, thus better meeting the diverse wavelength-converting film requirements of different photovoltaic devices. Furthermore, the emission wavelength of the wavelength-converting film is substantially greater than 430nm, enabling the converted wavelength to be better utilized by photovoltaic devices.

[0066] The specific method for preparing a wavelength-converting adhesive film from the aforementioned adhesive film composition can be referenced in the prior art. In some preferred embodiments of the present application, the aforementioned light-converting adhesive film composition is uniformly mixed and then prepared by melt extrusion molding at 80-120°C to obtain a light-converting adhesive film. The resulting light-converting adhesive film exhibits excellent stability and high luminous efficiency, ensuring long-term effective performance, thereby extending the service life of the photovoltaic device.

[0067] According to another typical embodiment of the present application, a photovoltaic module is provided, comprising a wavelength conversion adhesive film, wherein the wavelength conversion adhesive film is the wavelength conversion adhesive film described above. The photovoltaic module comprising the wavelength conversion adhesive film described above has a high utilization rate of light energy.

[0068] Of course, depending on different needs or application scenarios, the application of the above-mentioned wavelength conversion film is not limited to the photovoltaic field, but can also be applied to agricultural film, architectural glass, textiles and other fields.

[0069] The following will further illustrate the beneficial effects that can be achieved by the present application in combination with embodiments and comparative examples.

[0070] Preparation Example 1

[0071] Compound 1 was prepared according to the following formula:

[0072]

[0073] Aniline (1.79 g, 19.2 mmol), p-bromobenzaldehyde (1.07 g, 5.76 mmol), 9,10-phenanthrenequinone (1 g, 4.8 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was evacuated with nitrogen three times. Refluxed under nitrogen for 16 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain the target intermediate (1.65 g, 78%) as a white solid, intermediate 1.

[0074] The above white solid (1.25 g, 2.78 mmol), 4-boronic acid-triphenylamine (964.6 mg, 3.34 mmol), potassium carbonate (1.92 g, 1.39 mmol), and tetrakistriphenylphosphine palladium (161 mg, 0.14 mmol) were placed in a 100 mL round-bottom flask. 30 mL of 1,4-dioxane and 3 mL of deionized water were added. The mixture was purged with nitrogen three times and refluxed under nitrogen for 24 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (1.2 g, 70%), the target compound 1.

[0075] Preparation Example 2

[0076] Compound 2 was prepared according to the following formula:

[0077]

[0078] Aniline (1.79 g, 19.2 mmol), 4-formyltriphenylamine (1.6 g, 5.76 mmol), 9,10-phenanthrenequinone (1 g, 4.8 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was purged with nitrogen three times. The mixture was refluxed under nitrogen for 16 hours. After the reaction was completed, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (2.2 g, 85%), the target compound 2.

[0079] Preparation Example 3

[0080] Compound 3 was prepared according to the following formula:

[0081]

[0082] 3,6-Dibromophenanthrenequinone (2g, 5.5mmol), isobutylboronic acid (1.4g, 6.6mmol), tetrakistriphenylphosphine palladium (0.1g), and potassium carbonate (2.76g, 20mmol) were added to a 100mL round-bottom flask. The atmosphere was purged with nitrogen three times. Then, 15mL of toluene and 10mL of deionized water were added, respectively, and the mixture was stirred at 100°C for 24 hours. After the reaction was completed, the system was cooled to room temperature, 50mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using ethyl acetate / petroleum ether as the eluent to obtain an orange solid (1.6g, 90%), the target intermediate product, 3,6-diisobutylphenanthrenequinone.

[0083] 3,6-Diisobutylphenanthrenequinone (1.5 g, 4.8 mmol), 4-formyltriphenylamine (1.6 g, 5.76 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was evacuated with nitrogen three times. The mixture was refluxed under nitrogen for 16 hours. After the reaction was completed, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (2.5 g, 81%), the target compound 3.

[0084] Preparation Example 4

[0085] Compound 4 was prepared according to the following formula:

[0086]

[0087] Aniline (1.79 g, 19.2 mmol), 10-chloro-9-anthracenecarboxaldehyde (1.39 g, 5.76 mmol), 9,10-phenanthrenequinone (1 g, 4.8 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was purged with nitrogen three times. The mixture was refluxed under nitrogen for 16 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to yield a white solid (2.18 g, 90%).

[0088] The above white intermediate product (1.4 g, 2.78 mmol), 4-(9H-carbazol-9-yl)phenylboronic acid (959.0 mg, 3.34 mmol), K2CO3 (1.92 g, 1.39 mmol), and Pd(PPh3)4 (0.15 g) were placed in a 100 mL round-bottom flask. 30 mL of 1,4-dioxane and 3 mL of deionized water were added. The mixture was purged with nitrogen three times and refluxed under nitrogen for 24 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (1.64 g, 83%), namely, target compound 4.

[0089] Preparation Example 5

[0090] Compound 5 was prepared according to the following formula:

[0091]

[0092] Aniline (1.79 g, 19.2 mmol), 4-bromo-1-naphthaldehyde (1.35 g, 5.76 mmol), 9,10-phenanthrenequinone (1 g, 4.8 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was evacuated with nitrogen three times. The mixture was refluxed under nitrogen for 16 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain the white reaction intermediate (2.11 g, 88%).

[0093] The above intermediate product (1.39 g, 2.78 mmol), 4-boronic acid-triphenylamine (964.6 mg, 3.34 mmol), potassium carbonate (1.92 g, 1.39 mmol), and tetrakistriphenylphosphine palladium (161 mg, 0.14 mmol) were placed in a 100 mL round-bottom flask. 30 mL of 1,4-dioxane and 3 mL of deionized water were added. The mixture was purged with nitrogen three times and refluxed under nitrogen for 24 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (1.46 g, 79%), the target compound 5.

[0094] Preparation Example 6

[0095] Compound 6 was prepared according to the following formula:

[0096]

[0097] Aniline (1.79 g, 19.2 mmol), 6-bromo-2-naphthaldehyde (1.35 g, 5.76 mmol), 9,10-phenanthrenequinone (1 g, 4.8 mmol), and ammonium acetate (2.22 g, 11.52 mmol) were placed in a 100 mL round-bottom flask. 30 mL of acetic acid was added, and the mixture was evacuated with nitrogen three times. The mixture was refluxed under nitrogen for 16 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain the white reaction intermediate (2.04 g, 85%).

[0098] A 100 mL round-bottom flask was charged with the intermediate (1.39 g, 2.78 mmol), carbazole (558.5 mg, 3.34 mmol), sodium tert-butoxide (667.2 mg, 7 mmol), tri-tert-butylphosphine tetrafluoroborate (195 mg, 0.69 mmol), and palladium acetate (0.1 g). After evacuating the flask three times with nitrogen, 20 mL of toluene was added as the solvent and the mixture was refluxed under nitrogen for 24 hours. After the reaction, the system was cooled to room temperature, 50 mL of water was added, and the mixture was extracted three times with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and rotary evaporated. The crude product was purified by column chromatography using dichloromethane / petroleum ether as the eluent to obtain a white solid (1.22 g, 75%), the target compound 6.

[0099] Example 1

[0100] The performance of the wavelength conversion film prepared by using Compound 1 prepared in Example 1 as a light conversion agent was tested:

[0101] In parts by weight, the light-converting adhesive film composition includes 98 parts by weight of ethylene vinyl acetate, 1 part by weight of the target compound 1, 0.5 parts by weight of a cross-linking agent tert-butyl peroxyisopropyl carbonate, 0.3 parts by weight of a co-cross-linking agent trimethylolpropane tetraacrylate, and 0.2 parts by weight of vinyltrimethoxysilane. After the above light-converting adhesive film composition is mixed evenly, the light-converting adhesive film is prepared by melt extrusion molding and winding at 100°C.

[0102] Among them, absorption curve: using air as a reference, the film was tested at room temperature on a Shimadzu UV-2600 ultraviolet spectrophotometer to obtain data, obtain the maximum absorption wavelength, and list them in Table 1; emission curve: the prepared film was also directly placed in a Horiba FL-3 fluorescence spectrometer, and the measured maximum absorption wavelength was used as the excitation wavelength to collect the emission curve, obtain the maximum emission wavelength, and list them in Table 1; quantum efficiency test: at room temperature, using the integrating sphere accessory of the Horiba FL-3 fluorescence spectrometer, with the maximum absorption wavelength as the excitation light source, the absolute quantum efficiency value was measured, and the results are listed in Table 1.

[0103] Down Figure 1 The absorption curve of the wavelength conversion film prepared in Example 1 has a maximum absorption value of about 370nm, a wide effective absorption range, and a half-peak width greater than 50nm. Figure 2 is the emission curve of the film. The maximum emission wavelength is close to 435 nm, showing deep blue fluorescence and a quantum efficiency of 75%.

[0104] Example 2

[0105] The wavelength conversion film was prepared in the same manner as in Example 1, except that the light conversion agent was replaced with Compound 2 prepared in Example 2. The performance of the film was also tested in the same manner as in Example 1.

[0106] Figure 3 The UV-visible absorption spectrum of the prepared EVA film shows good absorption in the UV region, with a maximum absorption peak of about 370 nm, a large absorption range, a half-peak width greater than 50 nm, and almost no absorption in the visible light region (indicating good visible light transmittance). Figure 4 The fluorescence emission spectrum of the prepared EVA film is shown in Figure 2. Its maximum emission peak is located at 435 nm, and it emits deep blue light under a 365 nm UV lamp. The fluorescence quantum efficiency of the prepared film is about 70%.

[0107] Example 3

[0108] The wavelength conversion film was prepared in the same manner as in Example 1, except that the light conversion agent was replaced with Compound 3 prepared in Preparation Example 3, and its performance was tested.

[0109] Example 4

[0110] The wavelength conversion film was prepared in the same manner as in Example 1, except that the light conversion agent was replaced with Compound 4 prepared in Preparation Example 4, and its performance was tested.

[0111] Example 5

[0112] The wavelength conversion film was prepared in the same manner as in Example 1, except that the light conversion agent was replaced with Compound 5 prepared in Preparation Example 5, and its performance was tested.

[0113] Example 6

[0114] The wavelength conversion film was prepared in the same manner as in Example 1, except that the light conversion agent was replaced with Compound 6 prepared in Preparation Example 6, and its performance was tested.

[0115] Example 7

[0116] The difference from Example 1 is that the content of Compound 1 in the film composition is 0.01 wt %.

[0117] Example 8

[0118] The difference from Example 1 is that the content of Compound 1 in the film composition is 0.1 wt %.

[0119] Example 9

[0120] The difference from Example 1 is that the content of Compound 1 in the film composition is 0.5 wt %.

[0121] Example 10

[0122] The difference from Example 1 is that the content of Compound 1 in the film composition is 5 wt %.

[0123] Comparative Example 1

[0124] The difference from Example 1 is that compound 1 is replaced by benzotriazole having the structure of the following formula a. A wavelength conversion adhesive film is prepared according to the same method as Example 1, and its performance is tested.

[0125]

[0126] Comparative Example 2

[0127] The difference from Example 1 is that compound 1 is replaced by benzotriazole having the structure of the following formula b. A wavelength conversion adhesive film is prepared according to the same method as Example 1, and its performance is tested.

[0128]

[0129] The test results of the above embodiments and comparative examples are shown in Table 1 below.

[0130] Table 1

[0131]

[0132] From the above description, it can be seen that the above-mentioned embodiments of the present invention achieve the following technical effects: The imidazole derivatives of the aforementioned specific structure used as light conversion agents exhibit strong and broad absorption in the ultraviolet region, with the primary absorption portion above 350nm, and virtually no absorption in the visible region. This excellent visible light transmittance can better meet the diverse wavelength conversion film requirements of different photovoltaic devices. Furthermore, the light conversion agent exhibits a high absolute luminous quantum efficiency, with emission wavelengths generally exceeding 430nm, enabling the converted wavelengths to be better utilized by photovoltaic devices.

[0133] The foregoing description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Those skilled in the art will readily appreciate that various modifications and variations of the present invention are possible. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the present invention are intended to be within the scope of protection of the present invention.

Claims

1. A light conversion agent, characterized in that The chemical structural formula of the light conversion agent is at least one of Formula I to Formula IV: Where R a 、R b Each independently selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl and substituted or unsubstituted C0~C 20 hydroxyl groups; R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl and substituted or unsubstituted C0~C 20 hydroxyl groups; R2 is selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Heteroalkyl, substituted or unsubstituted C6~C 40 Aryl, substituted or unsubstituted C6~C 40 heteroaryl, substituted or unsubstituted arylamine, substituted or unsubstituted C1~C 20 amino, substituted or unsubstituted C1~C 20 Amide group, substituted or unsubstituted C3~C 20 Cyclic imide, substituted or unsubstituted C1~C 20 Alkoxy, substituted or unsubstituted C1~C 20 Carboxyl, substituted or unsubstituted C2~C 20 Ester group, substituted or unsubstituted C2~C 20 carbonyl and substituted or unsubstituted C0~C 20 of hydroxyl groups.

2. The light conversion agent according to claim 1, characterized in that The R1 is selected from substituted or unsubstituted C1 to C 20 Alkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C1~C 20 Ester group and substituted or unsubstituted C6~C 40 The aromatic group, Preferably, the R1 is selected from Wherein, R3 is selected from H, C1~C 10 Alkyl, substituted or unsubstituted C1~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Any one of an ester group and a substituted or unsubstituted C0-C8 amine group.

3. The light conversion agent according to claim 2, characterized in that The R2 is selected from Any of In the formula, R4 and R5 are independently selected from H, C1 to C 10 Alkyl, C2~C 10 Ester group, C2~C 10 Alkenyl, C1~C 10 Any one of an amide group and a C0-C8 amino group; R6 is selected from methylene, one or more hydrogen atoms of which are replaced by C1-C 10 Any one of an alkyl-substituted methylene, a single bond, O and S; Preferably, the R a 、R b Each independently selected from H, C1-C 10 Alkyl, C2~C 10 Alkenyl, C6~C 20 Aryl, C4~C 20 Heteroaryl, C1~C 10 amino, C1~C 10 Amide group, C3~C 10 Cyclic imide, C1~C 10 Alkoxy, C1~C 10 Carboxyl, C2~C 10 The ester group and C0~C 10 of hydroxyl groups.

4. The light conversion agent according to claim 3, characterized in that The light conversion agent is any one of the following structures: Preferably, in the formula, R3 is selected from H, C1-C8 alkyl, C2-C8 alkenyl and C2-C 10 The ester group, R4, R5 are each independently selected from H, C1 ~ C8 alkyl, C2 ~ C8 alkenyl and C2 ~ C 10 ester group.

5. A film composition comprising a base resin and a light-converting agent, characterized in that: The light conversion agent is the light conversion agent according to any one of claims 1 to 4.

6. The adhesive film composition according to claim 5, characterized in that The light conversion agent accounts for 0.01% to 5% by weight of the adhesive film composition, preferably 0.01% to 1.5%.

7. The adhesive film composition according to claim 5, characterized in that The matrix resin includes any one or more of EVA, PVA, PMMA, POE and silicone.

8. The adhesive film composition according to any one of claims 5 to 7, characterized in that: The adhesive film composition further includes an auxiliary agent, which includes any one or a combination of at least two of a cross-linking agent, a co-cross-linking agent, a silane coupling agent, a light stabilizer and an inorganic powder.

9. A wavelength conversion film, prepared by mixing and melt extruding a film composition, characterized in that: The adhesive film composition is the adhesive film composition according to any one of claims 5 to 8.

10. A photovoltaic module comprising a wavelength conversion film, characterized in that: The wavelength conversion adhesive film is the wavelength conversion adhesive film according to claim 9.

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