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

Abstract

The invention provides a light conversion agent, a light conversion adhesive film composition, a light conversion adhesive film and a photovoltaic module. The light conversion agent is a naphthotriazole compound, and the structural general formula of the naphthotriazole compound is as follows: # imgabs0 #, wherein i is any integer from 0 to 100; r1 and R '1 are selected from substituent groups such as substituted or non-substituted C1-C20 alkyl groups, and R2, R3, R4 and R' 4 are independently selected from substituent groups such as H and substituted or non-substituted C1-C20 alkyl groups. Compared with the prior art, the naphthotriazole with one more benzene ring in the application has a larger conjugate surface, so that the naphthotriazole has better coordination in the aspects of electron donating and electron withdrawing, and the naphthotriazole ring can always show wider-band absorption. The light conversion adhesive film prepared from the light conversion adhesive film composition has excellent light stability and high luminous efficiency, and can effectively play a role for a long time, so that the service life of a photovoltaic device (such as a photovoltaic module) is prolonged.

Description

Technical Field

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

[0002] As a clean energy source that's abundant and requires no transportation, solar energy holds great promise as a viable alternative to traditional fossil fuels. Consequently, the development of solar energy collection and conversion technologies has become a focus of national and societal attention. Photovoltaic devices, which directly convert solar energy into electricity, are one of the most efficient ways to utilize solar energy. Global demand for installed photovoltaic capacity continues to grow.

[0003] Since most photovoltaic devices can only effectively utilize sunlight in the visible and near-infrared wavelengths, their efficiency in utilizing ultraviolet light (wavelengths less than 400nm) is relatively low. Furthermore, the presence of ultraviolet light in sunlight can reduce the lifespan of photovoltaic devices, especially for heterojunction (HJT) cells, which are expected to replace PERC and TOPCon as third-generation solar cells. The use of light-conversion films can not only effectively absorb ultraviolet light in sunlight, preventing it from damaging the lifespan of photovoltaic devices, but also convert it into usable visible light, thereby improving the photovoltaic device's photoelectric conversion efficiency.

[0004] With the development of HJT cell technology, the importance of light-converting films has grown significantly. This is because, to achieve higher photoelectric conversion efficiency, HJT cells sacrifice UV stability in their modules. However, everyday photovoltaic devices inevitably face strong UV exposure. Therefore, using a light-converting film with high UV absorption and strong luminescence for module encapsulation not only effectively absorbs UV light from sunlight to prevent module damage, but also converts the absorbed UV light into visible light, increasing the cell's utilization of sunlight and achieving a gain effect. In short, the development of a high-performance light-converting film is of great significance to the development of HJT cells.

[0005] The core of light-converting film technology lies in the selection of light-converting agents. Currently, common types of light-converting agents include organic small molecules, polymers, quantum dots, and organometallic complexes. However, considering various factors such as cost, dispersibility, light-conversion performance, and visible light transmittance, organic small molecule light-converting agents (compared to inorganic light-converting agents) have the greatest application potential. However, organic light-converting agents currently exhibit poor photostability. Under UV irradiation, their light-conversion ability readily degrades significantly and yellows, which is often an unacceptable defect for film products. In recent years, a series of organic small molecule light-converting agents based on triazole structures have been developed, demonstrating high photostability. These research results demonstrate that the photostability limitations of organic small molecule light-converting agents are not insurmountable. However, there is still a pressing need to develop light-converting films with higher photoelectric conversion efficiency, improved stability, and longer lifespan. Summary of the Invention

[0006] The main purpose of the present invention is to provide a light conversion agent, a light conversion adhesive film composition, a light conversion adhesive film and a photovoltaic module to solve the problems of low photoelectric conversion efficiency, poor stability and short service life of traditional light conversion adhesive films in the prior art.

[0007] In order to achieve the above object, according to one aspect of the present invention, a light conversion agent is provided. The light conversion agent is a naphthotriazole compound. The general structural formula of the naphthotriazole compound is as follows:

[0008]

[0009] Wherein, i is any integer from 0 to 100; L i independently selected from any one of substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene; R1 and R'1 are independently selected from any one of substituted or unsubstituted C1~C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30 aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 any one of the substituted or unsubstituted hydroxyl groups; R2, R3, R4 and R'4 are independently selected from H, substituted or unsubstituted C1~C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30 aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C 20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; wherein the heteroatoms in the heteroalkyl, heteroaryl and heteroarylene groups are selected from any one or more of N, O and S; one or more methylene groups in R1, R'1, R2, R3, R4 and R'4 are optionally substituted by -O- or -S-.

[0010] Furthermore, when the above R1, R2, R3 and R4 have substituents, the substituents are selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, geminal cycloalkyl, C3-C6 heterocycloalkyl, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, amide, C2-C 10any one or more of the ester groups of ; preferably, the substituents are selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyl, vinyl, propenyl, butenyl, pentenyl, hexenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, formamide, methyl formate, ethyl formate, ethyl propionate, butyl propionate, ethyl butyrate, butyl butyrate, methyl hexanoate, methyl heptanoate, and ethyl octanoate.

[0011] Furthermore, the above R1 is selected from substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10 Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10 any one of substituted or unsubstituted hydrocarbon hydroxyl groups; R2, R3 and R4 are each independently selected from H, substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C4~C 20 Heteroaryl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10 wherein R1, R2, R3 and R4 are each independently selected from any one of the following substituents, which are substituted or unsubstituted: n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, isopentyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptyl alkenyl, octenyl, nonenyl, decenyl, allyl, phenyl, naphthyl, biphenyl, furyl, thienyl, indolyl, pyridyl, benzofuranyl, benzothienyl, methyl formate, ethyl formate, ethyl propionate, butyl propionate, ethyl butyrate, butyl butyrate, methyl hexanoate, methyl heptanoate, ethyl octanoate, amino, formylamino, acetylamino, propionylamino, butyrylamino, pentanoylamino, cyclopropionylamino, cyclobutyrylamino, cyclopropionimido, cyclobutyimido, carboxyl, carbonyl.

[0012] Furthermore, the general structural formula of the naphthotriazole compound is as follows:

[0013]

[0014] wherein m and n are each independently 1, 2, 3 or 4; R1 is selected from substituted or unsubstituted C1 to C 12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16 Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 any one of amino substituted or unsubstituted by aryl, C5-C8 alkyl substituted or unsubstituted acylamino, substituted or unsubstituted C5-C8 cyclic acylamino, substituted or unsubstituted C5-C8 cyclic imido, C5-C8 alkyl substituted or unsubstituted carboxyl, C5-C8 alkyl substituted or unsubstituted carbonyl, C5-C8 alkyl substituted or unsubstituted hydroxyl; preferably R4, R5 and R6 are each independently selected from H, substituted or unsubstituted C1-C8 12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 R4 is preferably H; preferably R1, R5 and R6 are each independently selected from any one of substituted or unsubstituted C5~C8 straight-chain alkyl, substituted or unsubstituted C5~C8 branched-chain alkyl, substituted or unsubstituted C5~C8 alkenyl, substituted or unsubstituted C4~C8 ester, phenyl substituted or unsubstituted amino; further, preferably R1, R5 and R6 are each independently selected from any one of

[0015]

[0016] Further, preferably R1 is selected from Any one of; preferably R5 and R6 are each independently selected from Any one of, further, preferably R5 and R6 are Any one of .

[0017] According to another aspect of the present invention, a light-converting adhesive film composition is provided. Calculated by weight, the light-converting adhesive film composition comprises 80% to 99.98% of a base resin, 0.01% to 10% of a light-converting agent, and 0.01% to 10% of an auxiliary agent, wherein the light-converting agent is the light-converting agent described above.

[0018] Furthermore, in terms of weight percentage, the light-converting adhesive film composition comprises 98% to 99.98% of a base resin, 0.01% to 1% of a light-converting agent, and 0.01% to 1% of an auxiliary agent; further, the mass ratio of the light-converting agent to the auxiliary agent is preferably 1:2 to 500, preferably 1:2 to 50.

[0019] Furthermore, the matrix resin is selected from any one or more of EVA, PVA, PMMA, POE, and silicone.

[0020] Furthermore, the auxiliary agent includes any one or a combination of at least two of a main cross-linking agent, an auxiliary cross-linking agent, a silane coupling agent and an inorganic powder.

[0021] According to another aspect of the present invention, a light-converting adhesive film is provided, which is prepared by mixing and molding an adhesive film composition, wherein the adhesive film composition is the light-converting adhesive film composition described above.

[0022] According to another aspect of the present invention, a photovoltaic module is provided, comprising a light conversion adhesive film, wherein the light conversion adhesive film is the aforementioned light conversion adhesive film.

[0023] The technical solution of the present invention is applied. The triazole structure is a structural unit of a classic optoelectronic functional material with very unique electronic properties. Specifically, the three connected N atoms on the five-membered aromatic ring of the triazole structure not only enable the triazole to have both the ability to donate and withdraw electrons, but also, compared with imidazole, the triazole structure also has a higher electron cloud density. When the triazole structure is connected to the aromatic ring to form a structure such as benzotriazole or naphthotriazole, the low-density π electron cloud of the benzene ring can effectively alleviate the electron cloud density on the triazole, thereby making the benzotriazole and naphthotriazole structures become very special rich electron acceptors. Such a rich electron acceptor structure can also form an effective conjugated system even if it is connected to some electron-donating groups with weaker electron-donating abilities, thereby realizing the transition and recovery of electrons from the ground state to the excited state, and radiating luminescence. Need to explain in particular, compared to benzotriazole, the naphthotriazole of an extra phenyl ring in the application is owing to having larger conjugated face, thereby make naphthotriazole no matter all have better coordination aspect electron giving, electron withdrawing, thereby when the periphery of naphthotriazole ring is connected some auxochrome groups, naphthotriazole ring often can show the absorption of more broadband.In addition, a phenyl ring more must cause naphthotriazole than the LUMO of benzotriazole lower, therefore, when the peripheral auxochrome group of naphthotriazole ring is identical, naphthotriazole all shows more red-shifted absorption and the emission effect than benzotriazole. In a word, for photovoltaic device, the light-converting agent with naphthotriazole as core has better light-converting performance.Meanwhile, naphthotriazole has more substitution sites, thereby makes it more conducive to the performance of light-converting agent being adjusted and optimized. Therefore, when we adopt naphthotriazole as luminescent core, the periphery of naphthotriazole ring is with some groups with electron donating ability, such as aryl, heteroaryl, amino etc. as auxochrome, just be easy to make naphthotriazole molecule have the characteristic of high luminescence, strong absorption. Further, when we replace the H atom on naphthotriazole with some alkyl, alkenyl, ester chain, particularly long-chain substituent, not only can effectively improve the solubility of light conversion agent, particularly alkyl substituent can also form a protective film at the periphery of luminescent group, thereby improving the light stability of light conversion adhesive film material. Meanwhile, the existence of these alkyl substituents can also avoid the luminescence quenching phenomenon caused by the accumulation of condensed ring aromatic hydrocarbons, and then improve the luminous efficiency of light conversion adhesive film material as a whole. Therefore, the light conversion adhesive film obtained using the light conversion adhesive film composition of the application has excellent light stability and high luminous efficiency concurrently, can effectively play a role for a long time, thereby improving the service life of photovoltaic device (such as photovoltaic module). DETAILED DESCRIPTION

[0024] It should be noted that, in the absence of conflict, the embodiments and features in the embodiments of the present application can be combined with each other. The present invention will be described in detail below with reference to the embodiments.

[0025] As analyzed in the background technology, traditional light-converting adhesive films in the prior art have problems such as low photoelectric conversion efficiency, poor stability and short service life. To solve this problem, the present invention provides a light-converting agent, a light-converting adhesive film composition, a light-converting adhesive film and a photovoltaic module.

[0026] In a typical embodiment of the present application, a light conversion agent is provided. The light conversion agent is a naphthotriazole compound. The general structural formula of the naphthotriazole compound is as follows:

[0027]

[0028] Wherein, i is any integer from 0 to 100; L i independently selected from any one of substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene; R1 and R'1 are independently selected from any one of substituted or unsubstituted C1~C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30 aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C 20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 any one of the substituted or unsubstituted hydroxyl groups; R2, R3, R4 and R'4 are independently selected from H, substituted or unsubstituted C1~C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C 20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; wherein the heteroatoms in the heteroalkyl, heteroaryl and heteroarylene groups are selected from any one or more of N, O and S; one or more methylene groups in R1, R'1, R2, R3, R4 and R'4 are optionally substituted by -O- or -S-.

[0029] As a classic building block of optoelectronic functional materials, the triazole structure possesses unique electronic properties. Specifically, the three connected nitrogen atoms on the five-membered aromatic ring of the triazole structure not only enable the triazole to possess both electron-donating and electron-withdrawing capabilities, but also possess a higher electron cloud density compared to imidazole. When the triazole structure is linked to an aromatic ring to form structures such as benzotriazole or naphthotriazole, the low-density π-electron cloud of the benzene ring effectively mitigates the electron cloud density on the triazole, making these structures highly specialized electron-rich acceptors. Such electron-rich acceptor structures can form effective conjugated systems even when linked to electron-donating groups with weaker electron-donating abilities, enabling electron transitions and recovery from the ground state to the excited state, resulting in luminescence. Need to explain in particular, compared to benzotriazole, the naphthotriazole of an extra phenyl ring in the application is owing to having larger conjugated face, thereby make naphthotriazole no matter all have better coordination aspect electron giving, electron withdrawing, thereby when the periphery of naphthotriazole ring is connected some auxochrome groups, naphthotriazole ring often can show the absorption of more broadband.In addition, a phenyl ring more must cause naphthotriazole than the LUMO of benzotriazole lower, therefore, when the peripheral auxochrome group of naphthotriazole ring is identical, naphthotriazole all shows more red-shifted absorption and the emission effect than benzotriazole. In a word, for photovoltaic device, the light-converting agent with naphthotriazole as core has better light-converting performance.Meanwhile, naphthotriazole has more substitution sites, thereby makes it more conducive to the performance of light-converting agent being adjusted and optimized. Therefore, when we adopt naphthotriazole as luminescent core, the periphery of naphthotriazole ring is with some groups with electron donating ability, such as aryl, heteroaryl, amino etc. as auxochrome, just be easy to make naphthotriazole molecule have the characteristic of high luminescence, strong absorption. Further, when we replace the H atom on naphthotriazole with some alkyl, alkenyl, ester chain, particularly long-chain substituent, not only can effectively improve the solubility of light conversion agent, particularly alkyl substituent can also form a protective film at the periphery of luminescent group, thereby improving the light stability of light conversion adhesive film material. Meanwhile, the existence of these alkyl substituents can also avoid the luminescence quenching phenomenon caused by the accumulation of condensed ring aromatic hydrocarbons, and then improve the luminous efficiency of light conversion adhesive film material as a whole. Therefore, the light conversion adhesive film obtained using the light conversion adhesive film composition of the application has excellent light stability and high luminous efficiency concurrently, can effectively play a role for a long time, thereby improving the service life of photovoltaic device (such as photovoltaic module).

[0030] In addition, the preferred L i Independently selected from substituted or unsubstituted C1-C 10 Alkylene, substituted or unsubstituted C2~C 10 Alkenylene, substituted or unsubstituted C4~C 40 Arylene, substituted or unsubstituted C2~C40 Any one of the heteroarylene groups; Further, in some embodiments, preferably L i At least one of the following is selected from 1,2-vinylene, 1,4-phenylene, 1,1'-biphenyl-4,4'-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 9H-fluorene-2,7-diyl, perylene-3,9-diyl, perylene-3,10-diyl or pyrene-1,6-diyl, 1H-pyrrole-2,5-diyl, furan-2,5-diyl, thiophene-2,5-diyl, thiophene thiophene-2,5-diyl, benzo[c]thiophene-1,3-diyl, dibenzo[b,d]thiophene-2,8-diyl, 9H-carbazole-3,6-diyl, 9H-carbazole-2,7-diyl, dibenzo[b,d]furan-2,8-diyl, 10H-phenothiazine-3,7-diyl and 10H-phenothiazine-2,8-diyl; each of which is optionally substituted.

[0031] In one embodiment of the present application, when R1, R2, R3 and R4 have substituents, the substituents are selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, geminal cycloalkyl, C3-C6 heterocycloalkyl, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, amide, C2-C 10 any one or more of the ester groups of ; preferably, the substituents are selected from methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyl, vinyl, propenyl, butenyl, pentenyl, hexenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, formamide, methyl formate, ethyl formate, ethyl propionate, butyl propionate, ethyl butyrate, butyl butyrate, methyl hexanoate, methyl heptanoate, and ethyl octanoate.

[0032] Compared to larger molecular weight light-converting agents, the relatively small molecular weight naphthotriazole light-converting agents described in this application not only offer significant advantages in production difficulty and cost control, but also tend to exhibit better photostability and adjustability. This may be due to the relatively small conjugated system of naphthotriazole light-converting agents. Therefore, selecting relatively small substituents within a certain range not only reduces production costs but also allows for simpler and more direct optimization of the light-converting agent's structure, thereby improving its performance.

[0033] In one embodiment of the present application, the above R1 is selected from substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10 Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10 any one of substituted or unsubstituted hydrocarbon hydroxyl groups; R2, R3 and R4 are each independently selected from H, substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C4~C 20 Heteroaryl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10 Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10wherein R1, R2, R3 and R4 are each independently selected from any one of the following substituents, which are substituted or unsubstituted: n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, isopentyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptyl alkenyl, octenyl, nonenyl, decenyl, allyl, phenyl, naphthyl, biphenyl, furyl, thienyl, indolyl, pyridyl, benzofuranyl, benzothienyl, methyl formate, ethyl formate, ethyl propionate, butyl propionate, ethyl butyrate, butyl butyrate, methyl hexanoate, methyl heptanoate, ethyl octanoate, amino, formylamino, acetylamino, propionylamino, butyrylamino, pentanoylamino, cyclopropionylamino, cyclobutyrylamino, cyclopropionimido, cyclobutyimido, carboxyl, carbonyl.

[0034] When the above substituents are preferably selected for R1, R2, R3 and R4, it helps to adjust and optimize the electronic structure of the luminescent core group, while supplementing the requirements for other properties of the light-converting agent during application. Specifically, the presence of an alkyl group can not only minimize the probability of luminescence quenching caused by the accumulation of relatively planar luminescent cores, but also enhance the solubility of the light-converting agent in the light-converting adhesive film composition, thereby improving the compatibility of the light-converting agent in the adhesive film. At the same time, the alkyl group can also serve as a protective layer to improve the stability of the light-converting agent. The role of the alkenyl group is similar to that of the alkyl group, but if the selected alkenyl group is a terminal alkenyl group, the terminal alkenyl group can also undergo a free radical cross-linking reaction with the adhesive film matrix resin, thereby making the light-converting agent more stable in the adhesive film, thereby reducing the migration rate of the additive caused by the high temperature environment in actual use scenarios. Ester groups and other substituents with heteroatoms, such as amino, amide, and carbonyl groups, not only function similarly to alkyl groups, but the presence of these heteroatoms, particularly N, O, and S atoms, can also form non-covalent interactions such as hydrogen bonds with heteroatoms in the film matrix resin. This hinders the movement of the entire light-converting agent molecule within the film, enhancing its rigidity and, in turn, reducing energy loss and improving light conversion efficiency. Substituents such as aryl and alkenyl groups can also modulate the electronic structure of the light-converting agent, allowing its light-conversion properties to be adjusted and optimized according to application requirements.

[0035] In one embodiment of the present application, the general structural formula of the naphthotriazole compound is as follows:

[0036]

[0037] wherein m and n are each independently 1, 2, 3 or 4; R1 is selected from substituted or unsubstituted C1 to C12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16 Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 any one of amino substituted or unsubstituted by aryl, C5-C8 alkyl substituted or unsubstituted acylamino, substituted or unsubstituted C5-C8 cyclic acylamino, substituted or unsubstituted C5-C8 cyclic imido, C5-C8 alkyl substituted or unsubstituted carboxyl, C5-C8 alkyl substituted or unsubstituted carbonyl, C5-C8 alkyl substituted or unsubstituted hydroxyl; preferably R4, R5 and R6 are each independently selected from H, substituted or unsubstituted C1-C8 12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16 Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 any one of aryl substituted or unsubstituted amino, C5~C8 hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C5~C8 cyclic acylamino, substituted or unsubstituted C5~C8 cyclic imino, C5~C8 hydrocarbon substituted or unsubstituted carboxyl, C5~C8 hydrocarbon substituted or unsubstituted carbonyl, C5~C8 hydrocarbon substituted or unsubstituted hydroxyl; preferably R4 is H; preferably R1, R5 and R6 are each independently selected from any one or more of substituted or unsubstituted C5~C8 straight-chain alkyl, substituted or unsubstituted C3~C8 branched alkyl, substituted or unsubstituted C5~C8 alkenyl, substituted or unsubstituted C4~C8 ester, phenyl substituted or unsubstituted amino, further preferably R1, R5 and R6 are each independently selected from

[0038]

[0039] Further, preferably R1 is selected from Further, preferably R1 is selected from Any one of; preferably R5 and R6 are each independently selected from Any one of, further, preferably R5 and R6 are Any one of .

[0040] When further considering the performance requirements of the light-converting agent, it is appropriate to select C4-C8 straight-chain alkanes, C4-C8 alkenes, or C4-C8 esters for R1, while short-chain esters and tert-butyl groups for R5 and R6 are preferred. Dividing the roles of different substituents is a good way to improve the overall performance of the material. Excessively long or numerous alkyl chains can lead to insufficient rigidity or even liquidization, thus compromising its light conversion efficiency. Considering the production cost constraints on molecular weight, C4-C8 substituents are a suitable choice. However, if the peripheral benzene rings of naphthotriazole are unsubstituted, π-π stacking between adjacent molecules will inevitably occur, leading to luminescence quenching. Therefore, the tert-butyl group, as a substituent with the smallest unit size but the best steric effect, is clearly a suitable choice for this application.

[0041] In another typical embodiment of the present application, a light-converting adhesive film composition is provided, which comprises, by weight percentage, 80% to 99.98% of a base resin, 0.01% to 10% of a light-converting agent, and 0.01% to 10% of an auxiliary agent, wherein the light-converting agent is the aforementioned light-converting agent.

[0042] The preferred content of the aforementioned light-converting adhesive film composition helps to more fully utilize the functions of each component and enhances their overall synergistic effect. The preferred mass ratio of the light-converting agent to the auxiliary agent helps to fully utilize their synergistic effect, thereby enhancing the compatibility of the light-converting agent with the matrix resin. This allows the broadband absorption effect of the naphthotriazole ring to be fully utilized, thereby improving the overall luminous efficiency of the light-converting adhesive film material. Therefore, the light-converting adhesive film obtained using the light-converting adhesive film composition of the present application exhibits both excellent light stability and high luminous efficiency, ensuring long-term effective performance and thus extending the service life of photovoltaic devices (such as photovoltaic modules).

[0043] In one embodiment of the present application, the light-converting adhesive film composition comprises, by weight percentage, 98% to 99.98% of a base resin, 0.01% to 1% of a light-converting agent, and 0.01% to 1% of an auxiliary agent; further, the mass ratio of the light-converting agent to the auxiliary agent is preferably 1:2 to 500, preferably 1:2 to 50.

[0044] The preferred contents of the above components and the mass ratio of the light conversion agent to the auxiliary agent help to further enhance the synergistic effect of the components, thereby improving the crosslinking effect of the crosslinking agent and further improving the performance of the light conversion adhesive film.

[0045] Preferably, the above-mentioned matrix resin is selected from any one or more of EVA, PVA, PMMA, and POE, so as to better cooperate with components such as the light-converting agent to obtain a light-converting adhesive film with excellent performance. The above-mentioned matrix resin is cheap, which helps to reduce costs. Of course, those skilled in the art can also use other matrix resins, which will not be repeated here.

[0046] In one embodiment of the present application, the auxiliary agent includes any one or a combination of at least two of a main cross-linking agent, an auxiliary cross-linking agent, a silane coupling agent, a light stabilizer and an inorganic powder.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] In another typical embodiment of the present application, a light-converting adhesive film is provided. The light-converting adhesive film is prepared by mixing and molding an adhesive film composition, and the adhesive film composition is the aforementioned light-converting adhesive film composition.

[0054] In some preferred embodiments of the present application, after the aforementioned light-converting adhesive film composition is evenly mixed, a light-converting adhesive film is prepared by a preparation process such as melt extrusion molding at 80-120°C. The obtained light-converting adhesive film has both excellent stability and high luminous efficiency, and can effectively function for a long time, thereby improving the service life of the photovoltaic device.

[0055] In another typical embodiment of the present application, a photovoltaic module is provided, comprising a light-converting adhesive film, which is the light-converting adhesive film described above.

[0056] The photovoltaic module including the above-mentioned light-converting film of the present application has excellent photoelectric conversion efficiency. Of course, there are more choices according to different needs and application scenarios. The light-converting film of the present application is not limited to photovoltaic devices, agricultural films, architectural glass and other fields.

[0057] The beneficial effects of the present application will be described below with reference to specific embodiments and comparative examples.

[0058] Example 1

[0059] In parts by weight, the light-converting adhesive film composition includes 98.8 parts by weight of ethylene vinyl acetate, 0.2 parts by weight of naphthotriazole compounds, 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 light-converting adhesive film composition is mixed evenly, it is melt-extruded into a film at 100°C to obtain a light-converting adhesive film.

[0060] Among them, the structural formula of the naphthotriazole compound is as follows:

[0061] (labeled as naphthotriazole compound a)

[0062] Furthermore, the synthetic route of naphthotriazole compounds is as follows:

[0063]

[0064] The specific steps are as follows:

[0065] Synthesis of M1:

[0066] Dissolve 2,3-diaminonaphthalene (5 g, 31.6 mmol) in 200 mL of acetic acid. Add liquid bromine (15.2 g, 94.8 mmol) dropwise to the acetic acid solution while stirring. Stir at room temperature for 3 to 6 hours and stop the reaction. Pour the reaction product into water for precipitation. After filtration, wash the filter cake with a large amount of deionized water to obtain an off-white solid powder, which is the crude product. Use ethyl acetate / petroleum ether as eluent and purify the crude product by column chromatography to obtain pure M1 (7.5 g, 75%).

[0067] Synthesis of M2:

[0068] M1 (5 g, 15.8 mmol) was dissolved in 100 mL of acetic acid. Under stirring, an aqueous sodium nitrite solution (2.2 g, 31.6 mmol) was added dropwise to the acetic acid solution to obtain a mixed solution. The mixed solution was stirred at room temperature for half an hour, and the product system was cooled. The product system was filtered and washed with alkali to remove acid, and finally a relatively pure white solid powder, namely M2 (4.65 g, 90%), was obtained.

[0069] Synthesis of M3:

[0070] M2 (4 g, 12.2 mmol) and sodium hydroxide (0.8 g) were dissolved in 80 mL of DMF to obtain a reaction system. 1-Bromooctane (2.8 g, 14.6 mmol) was slowly added dropwise to the reaction system while stirring the reaction system. The reaction system was stirred overnight at 40° C., and then washed with water, extracted, and separated to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as an eluent to obtain a relatively pure white solid powder, namely M3 (2.4 g, 45%).

[0071] Synthesis of naphthotriazole compound a:

[0072] M3 (2g, 4.6mmol), 4-tert-butylphenylboronic acid (1.95g, 10.9mmol), potassium carbonate (2.54g, 18.4mmol) and tetrakis triphenylphosphine palladium (0.1g) were mixed in a two-necked flask to obtain a mixed system. After nitrogen replacement of the mixed system, 30mL of toluene and 10mL of deionized water were injected therein. The mixed system was heated to 100°C and the reaction was stopped after stirring for 24h to obtain a reaction product. The reaction product was washed, extracted and separated in sequence to obtain an organic phase, which was dried and filtered with anhydrous magnesium sulfate to obtain a crude product. The crude product was mixed to obtain a mixed sample, and ethyl acetate / petroleum ether mixed solvent was used as eluent to separate and purify the mixed sample by column chromatography to finally obtain a relatively pure off-white solid powder, i.e., naphthotriazole compound a (2.06g, 82%).

[0073] Example 2

[0074] The difference from Example 1 is that the structural formula of the benzotriazole compound is as follows:

[0075] (labeled as naphthotriazole compound b), and finally a light-converting adhesive film was obtained.

[0076] Among them, the synthesis route of naphthotriazole compounds is as follows:

[0077]

[0078] The specific steps are as follows:

[0079] The synthesis of M1 and M2 in Example 2 is consistent with the synthesis process in Example 1.

[0080] Synthesis of M4:

[0081] M2 (4 g, 12.2 mmol) and sodium hydroxide (0.8 g) were dissolved in 80 mL of DMF to obtain a reaction system. Under stirring, ethyl 4-bromobutyrate (2.86 g, 14.6 mmol) was slowly added dropwise to the reaction system. The reaction system was stirred overnight at 40° C., washed with water, extracted, and separated to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as an eluent to obtain a relatively pure white solid powder, namely M4 (2.7 g, 50%).

[0082] Synthesis of naphthotriazole compound b:

[0083] M4 (2g, 4.5mmol), 4-tert-butylphenylboronic acid (1.92g, 10.8mmol), potassium carbonate (2.48g, 18mmol) and tetrakistriphenylphosphine palladium (0.1g) were mixed in a two-necked flask to obtain a mixed system. After nitrogen replacement of the mixed system, 30mL of toluene and 10mL of deionized water were injected therein. The mixture was heated to 100°C and stirred for 24h before the reaction was stopped. The reaction product was washed, extracted and separated in sequence to obtain an organic phase, which was dried over anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample, and ethyl acetate / petroleum ether mixed solvent was used as eluent to separate and purify the mixed sample by column chromatography to obtain a relatively pure off-white solid powder, i.e., naphthotriazole compound b (1.97g, 80%).

[0084] Example 3

[0085] The difference from Example 1 is that the structural formula of the benzotriazole compound is as follows:

[0086] (labeled as naphthotriazole compound c), and finally a light-converting adhesive film was obtained.

[0087] Among them, the synthesis route of naphthotriazole compounds is as follows:

[0088]

[0089] The specific steps are as follows:

[0090] The synthesis of M1 and M2 in Example 3 is consistent with the synthesis process in Example 1.

[0091] Synthesis of M5:

[0092] M2 (4 g, 12.2 mmol) and sodium hydroxide (0.8 g) were dissolved in 80 mL of DMF to obtain a reaction system. 6-Bromo-1-hexene (2.38 g, 14.6 mmol) was slowly added dropwise to the reaction system while stirring the reaction system. The reaction system was stirred overnight at 40° C., washed with water, extracted, and separated to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as the eluent to obtain a relatively pure white solid powder, namely M5 (2.4 g, 48%).

[0093] Synthesis of naphthotriazole compound c:

[0094] M5 (2 g, 4.9 mmol), 4-tert-butylphenylboronic acid (1.92 g, 10.8 mmol), potassium carbonate (2.7 g, 19.6 mmol) and tetrakistriphenylphosphine palladium (0.1 g) were mixed in a two-necked flask to obtain a mixed system. After nitrogen replacement of the mixed system, 30 mL of toluene and 10 mL of deionized water were injected therein. The mixture was heated to 100 ° C. and stirred for 24 h before the reaction was stopped to obtain a reaction product. The reaction product was washed, extracted and separated in sequence to obtain an organic phase, which was dried with anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample, and ethyl acetate / petroleum ether mixed solvent was used as eluent. The mixed sample was separated and purified by column chromatography to finally obtain a relatively pure off-white solid powder, i.e., naphthotriazole compound c (2.15 g, 85%).

[0095] Example 4

[0096] The difference from Example 1 is that the structural formula of the benzotriazole compound is as follows:

[0097] (labeled as naphthotriazole compound d), and finally a light-converting adhesive film was obtained.

[0098] Among them, the synthesis route of naphthotriazole compounds is as follows:

[0099]

[0100] The specific steps are as follows:

[0101] The synthesis of M1 and M2 in Example 4 is consistent with the synthesis process in Example 1.

[0102] Synthesis of M6:

[0103] M2 (4 g, 12.2 mmol) and sodium hydroxide (0.8 g) were dissolved in 80 mL of DMF to obtain a reaction system. 2-Bromoethyl acrylate (2.6 g, 14.6 mmol) was slowly added dropwise to the reaction system under stirring. The reaction system was stirred overnight at 40° C., washed with water, extracted, and separated to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as the eluent to obtain a relatively pure white solid powder, namely M6 (2.18 g, 42%).

[0104] Synthesis of naphthotriazole compound d:

[0105] M6 (2 g, 4.7 mmol), 4-tert-butylphenylboronic acid (1.84 g, 10.3 mmol), potassium carbonate (2.59 g, 18.8 mmol), and tetrakistriphenylphosphine palladium (0.1 g) were mixed in a two-necked flask to obtain a mixture. After nitrogen displacement, 30 mL of toluene and 10 mL of deionized water were injected into the mixture. The mixture was heated to 100°C and stirred for 24 h before the reaction was stopped. The reaction product was washed, extracted, and separated in sequence to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as the eluent to obtain a relatively pure off-white solid powder, namely, naphthotriazole compound d (2.05 g, 82%).

[0106] Example 5

[0107] The difference from Example 1 is that the structural formula of the benzotriazole compound is as follows:

[0108] (labeled as naphthotriazole compound e), and finally a light-converting adhesive film was obtained.

[0109] Among them, the synthesis route of naphthotriazole compounds is as follows:

[0110]

[0111] The specific steps are as follows:

[0112] The synthesis of M1, M2, and M3 in Example 5 is consistent with the synthesis process in Example 1.

[0113] Synthesis of naphthotriazole compounds e:

[0114] M3 (2 g, 4.6 mmol), 4-triphenylamine borate (3.15 g, 10.9 mmol), potassium carbonate (2.54 g, 18.4 mmol) and tetrakistriphenylphosphine palladium (0.1 g) were mixed in a two-necked flask to obtain a mixed system. After nitrogen replacement of the mixed system, 30 mL of toluene and 10 mL of deionized water were injected therein. The mixture was heated to 100 ° C. and stirred for 24 h before the reaction was stopped. The reaction product was washed, extracted and separated in sequence to obtain an organic phase, which was dried with anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample, and ethyl acetate / petroleum ether mixed solvent was used as eluent to separate and purify the mixed sample by column chromatography to finally obtain a relatively pure off-white solid powder, namely naphthotriazole compound e (2.76 g, 78%).

[0115] Example 6

[0116] The difference from Example 1 is that the structural formula of the benzotriazole compound is as follows:

[0117] (labeled as naphthotriazole compound f), and finally a light-converting adhesive film was obtained.

[0118] Among them, the synthesis route of naphthotriazole compounds is as follows:

[0119]

[0120] The specific steps are as follows:

[0121] The synthesis of M1 and M2 in Example 6 is consistent with the synthesis process in Example 1.

[0122] Synthesis of M7:

[0123] M2 (4 g, 12.2 mmol) and sodium hydroxide (0.8 g) were dissolved in 80 mL of DMF to obtain a reaction system. Under stirring, isobutyl bromide (2.0 g, 14.6 mmol) was slowly added dropwise to the reaction system. The reaction system was stirred overnight at 40° C., washed, extracted, and separated to obtain an organic phase. The organic phase was dried over anhydrous magnesium sulfate and filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample. The mixed sample was separated and purified by column chromatography using an ethyl acetate / petroleum ether mixed solvent as the eluent to obtain a relatively pure white solid powder, namely M7 (2.48 g, 52%).

[0124] Synthesis of naphthotriazole compound f:

[0125] M7 (2 g, 5.2 mmol), 4-(2-methoxy-2-oxoethyl)phenylboronic acid (2.22 g, 11.4 mmol), potassium carbonate (2.87 g, 20.8 mmol) and tetrakistriphenylphosphine palladium (0.1 g) were mixed in a two-necked flask to obtain a mixed system. After nitrogen replacement of the mixed system, 30 mL of toluene and 10 mL of deionized water were injected into the mixed system. The mixture was heated to 100 ° C. and stirred for 24 h before the reaction was stopped. The reaction product was washed, extracted and separated in sequence to obtain an organic phase, which was dried over anhydrous magnesium sulfate and then filtered to obtain a crude product. The crude product was mixed to obtain a mixed sample, and ethyl acetate / petroleum ether mixed solvent was used as eluent to separate and purify the mixed sample by column chromatography to obtain a relatively pure off-white solid powder, namely naphthotriazole compound f (2.17 g, 80%).

[0126] Example 7

[0127] The difference from Example 1 is that, in parts by weight, the light-converting adhesive film composition includes 98 parts by weight of ethylene vinyl acetate, 1 part by weight of naphthotriazole compound a, 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, to finally obtain a light-converting adhesive film.

[0128] Example 8

[0129] The difference from Example 1 is that, in parts by weight, the light-converting adhesive film composition includes 98 parts by weight of ethylene vinyl acetate, 0.67 parts by weight of naphthotriazole compound a, 0.63 parts by weight of a cross-linking agent tert-butyl peroxyisopropyl carbonate, 0.4 parts by weight of a co-cross-linking agent trimethylolpropane tetraacrylate, and 0.3 parts by weight of vinyltrimethoxysilane, ultimately obtaining a light-converting adhesive film.

[0130] Example 9

[0131] The difference from Example 1 is that, in parts by weight, the light-converting adhesive film composition includes 98 parts by weight of ethylene vinyl acetate, 0.039 parts by weight of naphthotriazole compound a, 1 part by weight of a cross-linking agent tert-butyl peroxyisopropyl carbonate, 0.66 parts by weight of a co-cross-linking agent trimethylolpropane tetraacrylate, and 0.301 parts by weight of vinyltrimethoxysilane, ultimately obtaining a light-converting adhesive film.

[0132] Example 10

[0133] The difference from Example 1 is that, in parts by weight, the light-converting adhesive film composition includes 98 parts by weight of ethylene vinyl acetate, 0.08 parts by weight of naphthotriazole compound a, 1 part by weight of a cross-linking agent tert-butyl peroxyisopropyl carbonate, 0.62 parts by weight of a co-cross-linking agent trimethylolpropane tetraacrylate, and 0.3 parts by weight of vinyltrimethoxysilane, to finally obtain a light-converting adhesive film.

[0134] Example 11

[0135] The difference from Example 1 is that, based on parts by weight, the base resin is ethylene-1-octene, and a light-converting adhesive film is finally obtained.

[0136] Comparative Example 1

[0137] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202310353493.6), and finally a light-converting adhesive film is obtained.

[0138] Comparative Example 2

[0139] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202310353493.6), and finally a light-converting adhesive film is obtained.

[0140] Comparative Example 3

[0141] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202310353493.6), and finally a light-converting adhesive film is obtained.

[0142] Comparative Example 4

[0143] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202311535255.3), and finally a light-converting adhesive film is obtained.

[0144] Comparative Example 5

[0145] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202311535255.3), and finally a light-converting adhesive film is obtained.

[0146] Comparative Example 6

[0147] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202311712843.X), and finally a light-converting adhesive film is obtained.

[0148] Comparative Example 7

[0149] The difference from Example 1 is that the light conversion agent is (disclosed in the Chinese patent application document with application number 202311712843.X), and finally a light-converting adhesive film is obtained.

[0150] Comparative Example 8

[0151] The difference from Example 1 is that, in parts by weight, the light-converting adhesive film composition includes 70 parts by weight of a base resin, 15 parts by weight of a naphthotriazole compound a, 5 parts by weight of a cross-linking agent tert-butyl peroxyisopropyl carbonate, 5 parts by weight of a co-cross-linking agent trimethylolpropane tetraacrylate, and 5 parts by weight of vinyltrimethoxysilane, and finally a light-converting adhesive film is obtained.

[0152] Test Method

[0153] Photovoltaic modules were prepared using the light-converting adhesive films obtained in the above embodiments and comparative examples of the present application. Specifically, the glass, light-converting adhesive film, and glass were stacked in sequence, and then vacuum-laminated to obtain a pre-pressed module. The following test methods were used to test the following properties of the photovoltaic module, and the above test results are listed in Table 1.

[0154] Light conversion efficiency: Horiba spectrometer FL-3, absolute quantum efficiency test was performed using an integrating sphere at room temperature.

[0155] Aging test: The upper and lower surfaces of the light-converting adhesive films obtained in the above embodiments and comparative examples were laminated with glass layers to obtain pre-pressed components, and UV300 aging tests were performed in a multi-fold UV aging box (power 142W, temperature 70°C).

[0156] Yellowing index: The yellowing index (ΔYI) of the pre-pressed components before and after the aging test was measured in accordance with the national standard GB 2409 "Test method for yellowness index of plastics".

[0157] Water vapor transmission rate: The test method refers to the standard GB / T 29848 "Ethylene-vinyl acetate copolymer (EVA) film for photovoltaic module encapsulation".

[0158] Table 1

[0159]

[0160]

[0161] It can be seen from the above that compared with the comparative example, the absorption wavelength and emission wavelength of the light-converting adhesive film obtained in the embodiment of the present application are significantly longer, that is, a significant red shift occurs. In the embodiment of the present application, the emission wavelength is closer to 500nm, and therefore, the gain effect on the photovoltaic module (such as the power of the photovoltaic module) is better.

[0162] From the above description, it can be seen that the above embodiments of the present invention achieve the following technical effects:

[0163] As a classic building block of optoelectronic functional materials, the triazole structure possesses unique electronic properties. Specifically, the three connected nitrogen atoms on the five-membered aromatic ring of the triazole structure not only enable the triazole to possess both electron-donating and electron-withdrawing capabilities, but also possess a higher electron cloud density compared to imidazole. When the triazole structure is linked to an aromatic ring to form structures such as benzotriazole or naphthotriazole, the low-density π-electron cloud of the benzene ring effectively mitigates the electron cloud density on the triazole, making these structures highly specialized electron-rich acceptors. Such electron-rich acceptor structures can form effective conjugated systems even when linked to electron-donating groups with weaker electron-donating abilities, enabling electron transitions and recovery from the ground state to the excited state, resulting in luminescence. Need to explain in particular, compared to benzotriazole, the naphthotriazole of an extra phenyl ring in the application is owing to having larger conjugated face, thereby make naphthotriazole no matter all have better coordination aspect electron giving, electron withdrawing, thereby when the periphery of naphthotriazole ring is connected some auxochrome groups, naphthotriazole ring often can show the absorption of more broadband.In addition, a phenyl ring more must cause naphthotriazole than the LUMO of benzotriazole lower, therefore, when the peripheral auxochrome group of naphthotriazole ring is identical, naphthotriazole all shows more red-shifted absorption and the emission effect than benzotriazole. In a word, for photovoltaic device, the light-converting agent with naphthotriazole as core has better light-converting performance.Meanwhile, naphthotriazole has more substitution sites, thereby makes it more conducive to the performance of light-converting agent being adjusted and optimized. Therefore, when we adopt naphthotriazole as luminescent core, the periphery of naphthotriazole ring is with some groups with electron donating ability, such as aryl, heteroaryl, amino etc. as auxochrome, just be easy to make naphthotriazole molecule have the characteristic of high luminescence, strong absorption. Further, when we replace the H atom on naphthotriazole with some alkyl, alkenyl, ester chain, particularly long-chain substituent, not only can effectively improve the solubility of light conversion agent, particularly alkyl substituent can also form a protective film at the periphery of luminescent group, thereby improving the light stability of light conversion adhesive film material. Meanwhile, the existence of these alkyl substituents can also avoid the luminescence quenching phenomenon caused by the accumulation of condensed ring aromatic hydrocarbons, and then improve the luminous efficiency of light conversion adhesive film material as a whole. Therefore, the light conversion adhesive film obtained using the light conversion adhesive film composition of the application has excellent light stability and high luminous efficiency concurrently, can effectively play a role for a long time, thereby improving the service life of photovoltaic device (such as photovoltaic module).

[0164] The above are merely preferred embodiments of the present invention and are 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 shall be included within the scope of protection of the present invention.

Claims

1. A light conversion agent, characterized in that The light conversion agent is a naphthotriazole compound, and the general structural formula of the naphthotriazole compound is as follows: Wherein, i is any integer from 0 to 100; L i independently selected from any one of substituted or unsubstituted alkylene, substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, and substituted or unsubstituted heteroarylene; R1 and R'1 are each independently selected from substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30 Aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C 20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 Any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; R2, R3, R4 and R'4 are each independently selected from H, substituted or unsubstituted C1-C 20 Alkyl, substituted or unsubstituted C2~C 20 Heteroalkyl, substituted or unsubstituted C2~C 20 Alkenyl, substituted or unsubstituted C6~C 40 aryl, substituted or unsubstituted C4~C 40 Heteroaryl, substituted or unsubstituted C2~C 20 Ester group, C1~C 20 Hydrocarbon substituted or unsubstituted amino, C6~C 30 Aryl substituted or unsubstituted amino, C1~C 20 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 20 Cyclic acylamino, substituted or unsubstituted C3~C 20 Cyclic imido, C1~C 20 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 20 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 20 Any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; The heteroatoms in the heteroalkyl, heteroaryl and heteroarylene groups are selected from any one or more of N, O and S; One or more methylene groups in the R1, R'1, R2, R3, R4 and R'4 are optionally substituted by -O- or -S-.

2. The light conversion agent according to claim 1, characterized in that When R1, R2, R3 and R4 have substituents, the substituents are selected from C1-C6 alkyl, C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, geminal cycloalkyl, C3-C6 heterocycloalkyl, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, amide, C2-C 10 Any one or more of the ester groups; Preferably, the substituent is selected from any one or more of methyl, ethyl, propyl, butyl, pentyl, hexyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, vinyl, propenyl, butenyl, pentenyl, hexenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, phenyl, anilino, naphthyl, biphenyl, halogen, hydroxyl, carboxyl, nitro, trifluoromethyl, trifluoromethoxy, cyano, amino, formamide, methyl formate, ethyl formate, ethyl propionate, butyl propionate, ethyl butyrate, butyl butyrate, methyl hexanoate, methyl heptanoate, and ethyl octanoate.

3. The light conversion agent according to claim 1 or 2, characterized in that The R1 is selected from substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 Aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10 Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10 Any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; The R2, R3 and R4 are each independently selected from H, substituted or unsubstituted C2 to C 10 Straight chain alkyl, substituted or unsubstituted C3~C 15 branched alkyl, substituted or unsubstituted C2~C 10 Heteroalkyl, substituted or unsubstituted C2~C 10 Alkenyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C4~C 20 Heteroaryl, substituted or unsubstituted C2~C 10 Ester group, C1~C 10 Hydrocarbon substituted or unsubstituted amino, C6~C 20 Aryl substituted or unsubstituted amino, C1~C 10 Hydrocarbon substituted or unsubstituted acylamino, substituted or unsubstituted C3~C 10 Cyclic acylamino, substituted or unsubstituted C3~C 10 Cyclic imido, C1~C 10 Hydrocarbon substituted or unsubstituted carboxyl, C1~C 10 Hydrocarbon substituted or unsubstituted carbonyl, C1~C 10 Any one of a hydrocarbon-substituted or unsubstituted hydroxyl group; Preferably, R1, R2, R3 and R4 are each independently selected from any one of the following substituted or unsubstituted substituents: n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, isobutyl, isopentyl, isohexyl, isoheptyl, isooctyl, isononyl, isodecyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, alkyl, aryl, thiophene, thiophene, thiophene-1, thiophene-2, thiophene-3, thiophene-4, thiophene-5, thiophene-6, thiophene-7, thiophene-8, thiophene-9, thiophene-11, thiophene-12, thiophene-13, thiophene-14, thiophene-15, thiophene-16, thiophene-17, thiophene-18, thiophene-19, thiophene-20, thiophene-21, thiophene-22, thiophene-23, thiophene-24, thiophene-25, thiophene-26, thiophene-27, thiophene-28, thiophene-29, thiophene-30, thiophene-31, thiophene-32 4. The light conversion agent according to claim 1 or 2, characterized in that The general structural formula of the naphthotriazole compound is as follows: wherein m and n are each independently 1, 2, 3 or 4; The R1 is selected from substituted or unsubstituted C1 to C 12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16 Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 any one of an aryl-substituted or unsubstituted amino group, a C5-C8 hydrocarbon-substituted or unsubstituted acylamino group, a substituted or unsubstituted C5-C8 cyclic acylamino group, a substituted or unsubstituted C5-C8 cyclic imido group, a C5-C8 hydrocarbon-substituted or unsubstituted carboxyl group, a C5-C8 hydrocarbon-substituted or unsubstituted carbonyl group, and a C5-C8 hydrocarbon-substituted or unsubstituted hydroxyl group; Preferably, R4, R5 and R6 are each independently selected from H, substituted or unsubstituted C1-C 12 Straight chain alkyl, substituted or unsubstituted C3~C 10 branched alkyl, substituted or unsubstituted C2~C 16 Alkenyl, substituted or unsubstituted C3~C8 ester group, C5~C8 alkyl substituted or unsubstituted amino group, C6~C 10 any one of an aryl-substituted or unsubstituted amino group, a C5-C8 hydrocarbon-substituted or unsubstituted acylamino group, a substituted or unsubstituted C5-C8 cyclic acylamino group, a substituted or unsubstituted C5-C8 cyclic imido group, a C5-C8 hydrocarbon-substituted or unsubstituted carboxyl group, a C5-C8 hydrocarbon-substituted or unsubstituted carbonyl group, and a C5-C8 hydrocarbon-substituted or unsubstituted hydroxyl group; preferably, R4 is H; Preferably, R1, R5 and R6 are each independently selected from any one or more of substituted or unsubstituted C5-C8 linear alkyl, substituted or unsubstituted C4-C8 branched alkyl, substituted or unsubstituted C5-C8 alkenyl, substituted or unsubstituted C3-C8 ester, phenyl substituted or unsubstituted amino. Further, preferably, R1, R5 and R6 are each independently selected from Further, preferably, R1 is selected from Any of the following; Preferably, the R5 and the R6 are each independently selected from Any one of, further, preferably said R5 and said R6 are both Any one of .

5. A light-converting adhesive film composition, characterized in that: Measured in percentage by weight, the light-converting adhesive film composition comprises: 80% to 99.98% base resin; 0.01% to 10% of a light-converting agent; and 0.01% to 10% additives, Wherein, the light conversion agent is the light conversion agent according to any one of claims 1 to 4.

6. The light conversion adhesive film composition according to claim 5, characterized in that: Measured in percentage by weight, the light-converting adhesive film composition comprises: 98% to 99.98% of the base resin; 0.01% to 1% of the light conversion agent; and 0.01% to 1% of the auxiliary agent; Furthermore, it is preferred that the mass ratio of the light conversion agent to the auxiliary agent is 1:2-500, more preferably 1:2-50.

7. The light conversion adhesive film composition according to claim 5 or 6, characterized in that: The matrix resin is selected from any one or more of EVA, PVA, PMMA, POE, and silicone.

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

9. A light-converting adhesive film, prepared by mixing and molding an adhesive film composition, characterized in that: The adhesive film composition is the light-converting adhesive film composition according to any one of claims 5 to 8.

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

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