Organic compounds containing a benzotriazole structure, and applications thereof, a composition for encapsulating adhesive, and a method for preparing an encapsulating adhesive

Abstract

The application relates to the field of solar cells, and discloses an organic compound containing a benzotriazole structure, application of the organic compound, a composition for encapsulation glue, and a method for preparing encapsulation glue. The compound provided by the application has a structure shown in formula (I), H on an ortho-methyl group forms a weak interaction with a nitrogen atom, a whole chelate ring is formed, absorption of ultraviolet light is increased, after the ultraviolet light is absorbed, energy is transferred to a light-emitting unit through intramolecular charge transfer, and then the energy is converted into visible light radiation, absorption of visible light by the solar cell is promoted, and photoelectric conversion efficiency is improved.

Description

Technical Field

[0001] This invention relates to the field of solar cells, and more specifically to organic compounds containing a benzotriazole structure and their applications, compositions for encapsulating adhesives, and methods for preparing encapsulating adhesives. Background Technology

[0002] With the deterioration of the environment, ultraviolet radiation is increasingly affecting humans.

[0003] In the field of solar cells, some cells age severely after being exposed to ultraviolet radiation, especially heterojunction modules. Their ultra-high photoelectric conversion efficiency is largely due to the excellent surface passivation ability of intrinsic amorphous silicon over crystalline silicon. However, the drawback is that the TCO film and amorphous silicon film absorb ultraviolet light, resulting in a lower current in the cells than ordinary cells, which leads to a decrease in module power.

[0004] Therefore, heterojunction modules have very high requirements for UV resistance. Although UV cut-off layers and UV absorbers can block UV radiation from reaching the module, they also reduce the module's light conversion efficiency. Therefore, in the photovoltaic field, it is necessary not only to prevent UV radiation aging of solar cell modules, but also to have a high-transmittance film layer in the visible light region, while simultaneously improving the photoelectric conversion efficiency of the module.

[0005] Light transfer agent is a product that can absorb negative gain light and convert it into positive gain light. It is added to the film as an additive or auxiliary agent to form a light transfer film.

[0006] Light transfer agents can not only absorb ultraviolet light, but also convert the absorbed ultraviolet light into visible light.

[0007] The functional principle of photoconverters is that after the material absorbs energy of a certain wavelength, the electrons are excited to the excited state and are in a high-energy state. This energy can be transferred to the central ion, causing its electrons to jump from the unstable high-energy state back to the stable ground state. At the same time, during the return process, the energy is released in the form of light, thereby realizing photoconversion.

[0008] However, existing encapsulation materials have low visible light transmittance, poor absorption of ultraviolet light, and low efficiency in converting ultraviolet light into visible light, thus limiting their ability to improve the conversion efficiency and weather resistance of solar cells.

[0009] Therefore, it is particularly urgent to develop ultraviolet light converters with high transmittance, the ability to absorb ultraviolet light and convert it into visible light with high efficiency, and high weather resistance. Summary of the Invention

[0010] The purpose of this invention is to overcome the shortcomings of existing technologies, such as low visible light transmittance, poor absorption of ultraviolet light by light conversion materials, and low efficiency in converting ultraviolet light into visible light.

[0011] To achieve the above objectives, a first aspect of the present invention provides an organic compound containing a benzotriazole structure, the organic compound having the structure shown in formula (I):

[0012]

[0013] In equation (I),

[0014] L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-20 Alkyl groups, where n is an integer from 1 to 20, and m is an integer from 1 to 20;

[0015] R1 is selected from H and C. 1-20 alkyl, C 1-20 alkoxy, unsubstituted or C 1-6 At least one group in the alkyl group substituted with C 5-12 Any one of the aromatic groups;

[0016] R4 is H or -C(R2)(R3)-CH3;

[0017] R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H;

[0018] Alternatively, the two R3s in formula (I) can cyclize together to form a 5-6 saturated carbon ring.

[0019] A second aspect of the invention provides the use of the organic compounds containing the benzotriazole structure described in the first aspect in encapsulating adhesives.

[0020] A third aspect of the present invention provides a composition for encapsulating adhesive, the composition comprising 100 parts by weight of a matrix material, 0.005-2 parts by weight of an ultraviolet light converter, 0-2 parts by weight of a photoinitiator, 0.1-1 parts by weight of a light stabilizer, 0-3 parts by weight of a crosslinking agent, 0-2 parts by weight of a co-crosslinking agent, 0.05-1 parts by weight of an antioxidant, and 0.2-1 parts by weight of a silane coupling agent; wherein the ultraviolet light converter is selected from the organic compounds containing a benzotriazole structure described in the first aspect.

[0021] A fourth aspect of the present invention provides a method for preparing an encapsulating adhesive, the method comprising: curing a material I containing each component of a composition to obtain the encapsulating adhesive; wherein the composition is the encapsulating adhesive composition described in the third aspect.

[0022] The present invention has at least the following specific advantages:

[0023] The organic compound of this invention comprises a triazole molecule, wherein the nitrogen atom at position 1 and / or 3 of the triazole can form a weak interaction with the H atom on the ortho-methyl group and the nitrogen atom, forming a chelate ring and increasing the conjugated area of ​​the molecule. As an ultraviolet light conversion agent, this organic compound can increase the absorption of ultraviolet light. After absorbing ultraviolet light, it transfers energy to the light-emitting unit through intramolecular charge transfer, and then converts it into visible light radiation, promoting the absorption of visible light by the solar cell and improving the photoelectric conversion efficiency of the photovoltaic module. At the same time, the chelate ring structure formed by this invention can increase the stability of the organic compound. As an ultraviolet light conversion agent, it can increase the stability of the ultraviolet light conversion encapsulation film, thereby improving the aging resistance of the photovoltaic module.

[0024] The organic compound provided by this invention has strong absorption of ultraviolet light, which is then converted into visible light and emitted. Furthermore, the ultraviolet light conversion encapsulation film containing the organic compound of this invention has high transmittance, which can increase the transmittance of visible light and thus improve the photoelectric conversion efficiency of photovoltaic modules. Detailed Implementation

[0025] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0026] In this invention, unless otherwise specified, groups of the same type have similar interpretations, and will not be described in detail here.

[0027] "L stands for -(CH2)" n -、-(CHR L ) m The expression "-, -C(CH3)(CH3)-, at least one linking group formed by removing any two leaving H atoms from benzene" indicates that L can be -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)- or a group formed by removing any two H atoms from benzene; L can also be -(CH2).n -、-(CHR L ) m -, -C(CH3)(CH3)-, and at least two of the following groups formed by removing any two leaving hydrogen atoms from benzene; for example, when L is -(CH2). n - and - (CHR) L ) m -When, for -(CH2) n - and - (CHR) L ) m The connection relationship of - is not subject to any special requirements and can be represented by -(CH2). n - and - (CHR) L ) m Any one of the elements can be connected to the parent nucleus structure, and can also be -(CH2). n -(CHR L ) m -(CH2) n - in the form of -.

[0028] C 1-20 The alkyl group refers to a straight-chain or branched alkyl group with a total number of carbon atoms of 1-20 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20). Exemplarily, it can be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, etc.

[0029] The linkage group formed by removing any two H atoms that can leave benzene can be represented by the linkage group formed by the removal of two H atoms at the para, meta, or ortho positions of benzene.

[0030] The aromatic group in this invention is interpreted broadly.

[0031] By C 1-6 At least one group in the alkyl group substituted with C 5-12 The aromatic group indicates that the total number of cyclic carbon atoms in the aromatic group is 5-12, containing "C". 1-6 When "alkyl" is mentioned, the "C" is used. 1-6 The number of carbon atoms in the alkyl group is not included in the C100. 5-12 The aromatic group is within the range of "5-12"; the aromatic group can be, for example, phenyl, naphthyl, etc.

[0032] "5-6 saturated carbon ring" means that the number of atoms forming the ring is 5 or 6, and all the atoms forming the ring are carbon atoms. The carbon ring is a saturated carbon ring.

[0033] "n is an integer from 1 to 20" means that n can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.

[0034] "m is an integer from 1 to 20" means that m can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.

[0035] As previously stated, a first aspect of the present invention provides an organic compound containing a benzotriazole structure, the organic compound having the structure shown in formula (I):

[0036]

[0037] In equation (I),

[0038] L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two H atoms from benzene, R L C 1-20 Alkyl groups, where n is an integer from 1 to 20, and m is an integer from 1 to 20;

[0039] R1 is selected from H and C. 1-20 alkyl, C 1-20 alkoxy, unsubstituted or C 1-6 At least one group in the alkyl group substituted with C 5-12 Any one of the aromatic groups;

[0040] R4 is H or -C(R2)(R3)-CH3;

[0041] R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H;

[0042] Alternatively, the two R3s in formula (I) can cyclize together to form a 5-6 saturated carbon ring.

[0043] Preferably, in formula (I),

[0044] L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two H atoms from benzene, RL C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10;

[0045] R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups;

[0046] R4 is H or -C(R2)(R3)-CH3;

[0047] R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H;

[0048] Alternatively, the two R3s in formula (I) can cyclize together to form a 5-6 saturated carbon ring.

[0049] Particularly preferably, the organic compound represented by formula (I) is selected from any one of the following:

[0050]

[0051]

[0052]

[0053] According to the first preferred embodiment, in formula (I),

[0054] L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10;

[0055] R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups;

[0056] R4 is H;

[0057] R2 and R3 are each independently selected from H and C. 1-8 Alkyl groups, and R2 and R3 are not both H.

[0058] In the aforementioned first preferred embodiment, more preferably, the organic compound represented by formula (I) is selected from any one of the following:

[0059]

[0060]

[0061] According to the second preferred embodiment, in formula (I), L may or may not exist, and optionally, L is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10;

[0062] R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups;

[0063] R4 is -C(R2)(R3)-CH3;

[0064] R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H.

[0065] In the aforementioned second preferred embodiment, more preferably, the organic compound represented by formula (I) is selected from any one of the following:

[0066]

[0067] According to the third preferred embodiment, in formula (I),

[0068] L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10;

[0069] R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups;

[0070] R4 is -C(R2)(R3)-CH3;

[0071] R2 is selected from H and C. 1-12 Alkyl groups;

[0072] The two R3s in formula (I) cyclize together to form a 5-6 saturated carbon ring.

[0073] In the aforementioned third preferred embodiment, more preferably, the organic compound represented by formula (I) is selected from any one of the following:

[0074]

[0075]

[0076] This invention does not impose any particular limitation on the specific methods for preparing the aforementioned organic compounds. Those skilled in the art can obtain the aforementioned organic compounds by combining the specific structural formulas provided by this invention with conventional process routes in the field of organic synthesis. Furthermore, several examples are exemplarily listed below to illustrate the methods for preparing the organic compounds of this invention. Those skilled in the art can also obtain specific methods for preparing all other organic compounds by changing the types of raw materials according to the methods for preparing the organic compounds described below. This invention will not elaborate on the preparation methods for all organic compounds, and this should not be construed as a limitation of the invention.

[0077] A second aspect of the invention provides the use of the organic compounds containing the benzotriazole structure described in the first aspect in encapsulating adhesives.

[0078] Preferably, the encapsulating adhesive is a light conversion encapsulating adhesive; more preferably, the encapsulating adhesive is an ultraviolet light conversion encapsulating adhesive.

[0079] As previously described, a third aspect of the present invention provides a composition for encapsulating adhesives, the composition comprising 100 parts by weight of a matrix material, 0.005-2 parts by weight of an ultraviolet light converter, 0-2 parts by weight of a photoinitiator, 0.1-1 parts by weight of a light stabilizer, 0-3 parts by weight of a crosslinking agent, 0-2 parts by weight of a co-crosslinking agent, 0.05-1 parts by weight of an antioxidant, and 0.2-1 parts by weight of a silane coupling agent; wherein the ultraviolet light converter is selected from the organic compounds containing a benzotriazole structure described in the first aspect.

[0080] More preferably, the composition contains 100 parts by weight of a matrix material, 0.01-1 parts by weight of an ultraviolet light converter, 0.1-2 parts by weight of a photoinitiator, 0.1-1 parts by weight of a light stabilizer, 0.1-3 parts by weight of a crosslinking agent, 0.1-2 parts by weight of a co-crosslinking agent, 0.05-1 parts by weight of an antioxidant, and 0.2-1 parts by weight of a silane coupling agent.

[0081] Preferably, the matrix material is an ethylene copolymer.

[0082] More preferably, the ethylene copolymer is any one or a mixture of at least two of the following: ethylene-vinyl acetate copolymer, ethylene-butene copolymer, ethylene-octene copolymer, ethylene-methyl acrylate copolymer, ethylene-ethyl acrylate copolymer, ethylene-vinyl acetate-based multi-component copolymer, ethylene-methyl acrylate-based multi-component copolymer, ethylene-ethyl acrylate-based multi-component copolymer, ethylene-methyl methacrylate-based multi-component copolymer, ethylene-ethyl methacrylate-based multi-component copolymer, and ethylene-α-olefin copolymer.

[0083] Particularly preferred is that the matrix material is an ethylene-vinyl acetate copolymer.

[0084] More preferably, the vinyl acetate structural unit content in the ethylene-vinyl acetate copolymer used as the matrix material is 25-35 wt%, the melt index of the ethylene-vinyl acetate copolymer is 0.1-40 g / min, the melting point is 40-90℃ (under the test conditions of 190℃ / 2.16 kg), and the light transmittance is ≥90%.

[0085] Preferably, the photoinitiator is selected from: 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxycyclohexylphenyl ketone, benzophenone, (2,4,6-trimethylbenzoyl)diphenylphosphine oxide, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, 2-hydroxy-2-methyl-1-phenylpropanone (2-hydroxy-1-(4-(2-hydroxy-2-methylpropionylphenyl)benzyl)-2-methyl-1-propanone, titanoceramsite photoinitiators, thiopyridinone / iodonium salt systems, organic peroxide systems, borate / dye systems, hexaaryl diimidazole / dye systems, coumarin ketone / dye systems, benzoyl ketal photoinitiators, acetophenone photoinitiators, anthraquinone photoinitiators and their derivatives, benzoate photoinitiators, bicyclic diketone compounds, camphorquinone, any one or a mixture of at least two of the following.

[0086] Preferably, the light stabilizer is selected from one or a mixture of at least two of the following: bis(2,2,6,6-tetramethyl-4-piperidinol) sebacate, bis-2,2,6,6-tetramethylpiperidinol sebacate, 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, [[3,5-di-tert-butyl-4-hydroxyphenyl]methyl]butylmalonate di(1,2,2,6,6-pentamethyl-4-piperidinol), bis(2,2,6,6-tetramethyl-4-piperidinol) sebacate, and 2,4-dichloro-6-(4-morpholino)-1,3,5-triazine.

[0087] Preferably, the crosslinking agent is selected from: tert-butyl peroxide, tert-butyl peroxide-isopropyl carbonate, cyclohexanone peroxide, tert-butyl hydrogen peroxide, dicumyl peroxide, di(tert-butyl peroxide-isopropyl)benzene, benzoyl peroxide, di(2,4-dichlorobenzoyl peroxide), tert-butyl peroxybenzoate, tert-butyl peroxycarbonate-2-ethylhexyl peroxide, tert-butyl peracetate, tert-butyl peroxide-3,5,5-trimethylhexanoate, di(4-tert-butylcyclohexanone) peroxybicarbonate, tert-amyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, 1,1-di-tert-butyl peroxycyclohexane, and 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, or a mixture of at least two of the following.

[0088] Preferably, the crosslinking agent is selected from one or a mixture of at least two of the following: triallyl isocyanurate, ethylene glycol dimethacrylate, N,N′-m-phenylbismaleimide, trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, ethoxylated trimethylolpropane triacrylate, propanetriol triacrylate, and ethoxylated pentaerythritol tetraacrylate.

[0089] Preferably, the antioxidant is selected from one or a mixture of at least two of the following: 2,6-di-tert-butyl-p-cresol, di(2,4-dicumylphenyl)pentaerythritol diphosphite, distearate pentaerythritol diphosphite, β-(3,5-di-tert-butyl-4-hydroxybenzyl)propionate, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanuric acid, β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate n-octadecyl alcohol, tetrakis(β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate)pentaerythritol ester, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), tetrakis(2,4-di-tert-butylphenyl-4,4'-biphenyl) diphosphite, tris(2,4-di-tert-butylphenyl) phosphite, and tris(nonylphenyl) phosphite.

[0090] Preferably, the silane coupling agent is selected from one or a mixture of at least two of the following: vinyltriethoxysilane, vinyltrimethoxysilane, vinyltri(2-methoxyethoxy)silane, 3-triethoxysilyl-1-propylamine, (triethoxysilyl)ethylene, γ-glycidoxypropyltrimethoxysilane, vinyltrichlorosilane, γ-methacryloyloxypropyltrimethoxysilane, γ-methacryloyloxypropyltriisopropoxysilane, 3-thiopropyltrimethoxysilane, and 3-thiopropyltriethoxysilane.

[0091] As previously stated, a fourth aspect of the present invention provides a method for preparing an encapsulating adhesive, the method comprising: curing a material I containing each component of a composition to obtain the encapsulating adhesive; wherein the composition is the encapsulating adhesive composition described in the third aspect.

[0092] In a more preferred embodiment, the curing process includes: sequentially mixing and casting the material I.

[0093] According to a particularly preferred embodiment, the method for preparing the encapsulating adhesive includes: uniformly mixing a matrix material, an ultraviolet light converter, a light stabilizer, a crosslinking agent, a co-crosslinking agent, an antioxidant, and a silane coupling agent, and then sequentially performing kneading and casting to obtain an encapsulating adhesive film.

[0094] Preferably, the mixing conditions include: a mixing temperature of 70℃-120℃; a mixing time of 10min-40min; and a stirring speed of 100rpm-300rpm.

[0095] Preferably, the thickness of the encapsulating film obtained after casting is 0.3 mm to 0.8 mm. More preferably, the thickness of the ultraviolet light conversion encapsulating film is 0.5 mm.

[0096] Optionally, the casting process is carried out in a casting machine, through plasticizing extrusion, stretching, traction, and winding, to obtain the encapsulating adhesive (film).

[0097] In a preferred embodiment, the present invention also provides a photovoltaic module comprising photovoltaic glass, an encapsulating film layer I, a solar cell, an encapsulating film layer II, and a photovoltaic backsheet, which are sequentially stacked; the materials forming the encapsulating film layer I and the encapsulating film layer II are each independently selected from at least one of the ultraviolet light conversion encapsulating films described above in the present invention.

[0098] Preferably, the present invention also provides a method for preparing the photovoltaic module, comprising:

[0099] (1) Photovoltaic glass, encapsulating film I, solar cell, encapsulating film II and photovoltaic backsheet are stacked in sequence to obtain intermediate body I;

[0100] (2) The intermediate I is subjected to hot pressing to obtain the photovoltaic module;

[0101] The encapsulating film I and the encapsulating film II are each independently selected from at least one of the ultraviolet light conversion encapsulating films described above in this invention.

[0102] More preferably, in the method for preparing the photovoltaic module, the method includes: sequentially stacking photovoltaic glass, the ultraviolet light conversion encapsulation film, solar cells, the ultraviolet light conversion encapsulation film, and a photovoltaic backsheet, and then heating and pressing them to obtain the photovoltaic module.

[0103] Preferably, in step (2), the conditions for the hot pressing treatment include: heating temperature of 80-170℃, pressing pressure of 40KPa-70KPa, and pressing time of 15-30min.

[0104] The present invention will be described in detail below through examples.

[0105] For the following examples where specific experimental steps or conditions are not specified, the procedures or conditions described in the literature of this field can be followed. Reagents or instruments whose manufacturers are not specified are all commercially available standard products.

[0106] Unless otherwise specified, room temperature and ambient temperature as used below refer to 25±1℃.

[0107] The ethylene-vinyl acetate copolymer used in this invention has a vinyl acetate structural unit content of 28 wt%, a melt index of 20 g / 10 min (under test conditions of 190 °C / 2.16 kg), and a melting point of 75 °C.

[0108] Preparation Example 1

[0109]

[0110] Synthesis of Intermediate 1-1: In a 500 mL three-necked flask, 0.05 mol of 4,7-dibromo-2H-benzo[d][1,2,3]triazole, 0.05 mol of diiodoisobutane, 0.125 mol of sodium tert-butoxide, 0.5 mmol of tris(dibenzylacetone)dipalladium, 0.5 mmol of tritert-butylphosphine, and 140 mL of toluene solvent were added sequentially. The mixture was stirred under nitrogen purging and heated to reflux for 8 h. HPLC analysis confirmed the reaction was complete. The reaction mixture was cooled to room temperature, and 250 mL of deionized water was added. The mixture was stirred for 10 min. The organic phase was washed three times with water, and the two phases were combined and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the organic solvent was evaporated. The residue was separated by silica gel column chromatography to obtain Intermediate 1-1 (yield: 82.5%).

[0111] Synthesis of Compound 1: The synthesis method was the same as that for intermediate 1-1, yielding Compound 1 (yield: 75.7%).

[0112] Mass spectrometry: C34H27N5, theoretical value: 505.23, measured value: 505.21. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.87~0.94 (6H, d), 1.97~2.11 (1H, m), 5.15~5.21 (2H, d), 7.07~7.24 (8H, m), 7.37~7.43 (2H, m), 7.50~7.54 (2H, m), 7.67~7.70 (2H, m), 8.15~8.23 (2H, m), 8.52~8.57 (2H, m).

[0113] Preparation Example 2

[0114]

[0115] Synthesis of intermediate 9-1: In a 500 ml three-necked flask, under nitrogen protection, 1,4-dioxane solvent (160 ml), intermediate 1-1 (0.05 mol), boron pinacol ester (0.1 mol), potassium acetate (0.25 mol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (1 mmol) were added sequentially. The mixture was heated to reflux for 4 h. HPLC analysis showed that the reaction was complete. After cooling the reaction solution to room temperature, the solution was evaporated under reduced pressure to obtain a crude product. The crude product was dissolved in toluene solvent, heated and stirred, and then heated to reflux. The solution was decolorized by hot silica gel column chromatography. The filtrate was evaporated under reduced pressure to obtain a small amount of solvent. Ethanol (200 ml) was added, and the mixture was stirred and recrystallized to obtain intermediate 9-1 (yield: 87.2%).

[0116] Synthesis of intermediate 9-2: In a 500 mL three-necked flask under nitrogen protection, intermediate 9-1 (0.03 mol), 2-chloro-2-bromopropane (0.06 mol), and a mixed solution of toluene, ethanol, and water (toluene, ethanol, and water in a volume ratio of 3:2:1) (100 mL) were added sequentially with stirring. Potassium carbonate (0.15 mol) and tetrakis(triphenylphosphine)palladium (0.6 mmol) were then added sequentially, and the mixture was heated to reflux for 6 h. HPLC analysis indicated that the reaction was essentially complete. Deionized water (150 mL) was added to the reaction solution, and the mixture was stirred for 10 min. The organic phase was washed three times with water, and the two phases were combined and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the organic solvent was evaporated, and the residue was separated by silica gel column chromatography to obtain intermediate 9-2 (yield: 68.3%).

[0117] Synthesis of compound 9: The synthesis method was the same as that for intermediate 1-1, yielding compound 9 (yield: 76.4%).

[0118] Mass spectrometry: C40H39N5, theoretical value: 589.32, measured value: 589.35. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.88~0.94 (6H, d), 1.76~1.80 (12H, s), 1.97~2.13 (1H, m), 4.95~5.00 (2H, d), 7.07~7.20 (6H, m), 7.37~7.45 (2H, m), 7.50~7.55 (2H, m), 7.74~7.80 (2H, m), 7.94~7.97 (2H, s), 8.32~8.36 (2H, m), 8.53~8.57 (2H, m).

[0119] Preparation Example 3

[0120]

[0121] Synthesis of intermediate 33-1: The synthesis method is the same as that of intermediate 1-1, yielding intermediate 33-1 (yield: 81.7%).

[0122] Synthesis of intermediate 33-2: The synthesis method is the same as that of intermediate 9-2, yielding intermediate 33-2 (yield: 67.5%).

[0123] Synthesis of compound 33: The synthesis method was the same as that for intermediate 1-1, yielding compound 33 (yield: 73.8%).

[0124] Mass spectrometry: C48H39N5, theoretical value: 685.32, measured value: 685.37. ¹H-NMR (400MHz, CDCl3) (ppm) δ=0.80~0.86(6H, d), 0.91~0.98(3H, d), 1.34~1.47(1H, m), 2.46~2.61(1H, m), 4.95~5.04 (1H, m), 5.27~5.36 (1H, m), 7.07~7.24 (8H, m), 7.36~7.43 (2H, m), 7.49~7.55 (2H , m), 7.88~7.95 (8H, m), 8.05~8.08 (2H, m), 8.15~8.22 (2H, d), 8.52~8.57 (2H, m).

[0125] Preparation Example 4

[0126]

[0127] Synthesis of intermediate 40-1: The synthesis method is the same as that of intermediate 9-1, yielding intermediate 40-1 (yield: 88.3%).

[0128] Synthesis of intermediate 40-2: The synthesis method is the same as that of intermediate 9-2, yielding intermediate 40-2 (yield: 67.4%).

[0129] Synthesis of intermediate 40-3: The synthesis method is the same as that of intermediate 1-1, yielding intermediate 40-3 (yield: 81.5%).

[0130] Synthesis of compound 40: The synthesis method was the same as that for intermediate 1-1, yielding compound 40 (yield: 77.3%).

[0131] Mass spectrometry: C53H65N5, theoretical value: 771.52, measured value: 771.55. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.87~0.93(12H, d), 1.18~1.22(36H, d), 2.10~2.26(2H, m), 5.38~5.45(1H, m), 7.12~7.17(2H, m), 7.32~7.37(2H, m), 7.38~7.42(2H, m), 7.50~7.54(2H, m), 7.68~7.70(2H, m), 8.18~8.20(2H, d), 8.95~8.97(2H, d).

[0132] Preparation Example 5

[0133]

[0134] Synthesis of compound 42: The synthesis method was the same as that for intermediate 1-1, yielding compound 42 (yield: 75.2%).

[0135] Mass spectrometry: C41H41N5O4, theoretical value: 667.32, measured value: 667.35. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.80~0.91 (12H, d), 1.97~2.09 (2H, m), 3.79~3.80 (12H, m), 5.40~5.43 (1H, m), 6.55~6.60 (2H, m), 7.15~7.20 (2H, m), 7.28~7.40 (4H, m), 7.65~7.67 (2H, m), 7.68~7.70 (2H, m), 8.20~8.22 (2H, m).

[0136] Preparation Example 6

[0137]

[0138] Synthesis of intermediate 46-1: The synthesis method is the same as that of intermediate 9-1, yielding intermediate 46-1 (yield: 69.5%).

[0139] Synthesis of intermediate 46-2: The synthesis method is the same as that for intermediate 9-2, yielding intermediate 46-2 (yield: 88.5%).

[0140] Synthesis of compound 46: The synthesis method was the same as that for intermediate 1-1, yielding compound 46 (yield: 78.6%).

[0141] Mass spectrometry: C45H49N5, theoretical value: 659.40, measured value: 659.46. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.87~0.93 (12H, d), 1.34~1.43 (12H, d), 2.13~2.29 (2H, m), 5.46~5.52 (5H, m), 7.18~7.28 (4H, m), 7.41~7.53 (4H, m), 7.62~7.68 (2H, m), 7.73~7.78 (2H, m), 7.86~7.88 (2H, m), 8.13~8.15 (2H, m), 8.16~8.18 (2H, m).

[0142] Preparation Example 7

[0143]

[0144] Synthesis of intermediate 54-1: The synthesis method is the same as that of intermediate 1-1, yielding intermediate 54-1 (yield: 83.0%).

[0145] Synthesis of compound 54: The synthesis method was the same as that for intermediate 1-1, yielding compound 54 (yield: 74.8%).

[0146] Mass spectrometry: C42H41N5, theoretical value: 615.34, measured value: 615.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.88~1.02 (8H, m), 1.25~1.35 (1H, m), 1.63~1.82 (3H, m), 2.15~2.30 (2H, m), 2.49~2.51 (12H, m), 4.29~4.40 (1H, m), 7.20~7.25 (2H, m), 7.32~7.41 (4H, m), 7.45~7.49 (2H, m), 7.68~7.70 (2H, m), 8.02~8.04 (2H, m), 8.79~8.81 (2H, m).

[0147] Preparation Example 8

[0148]

[0149] Synthesis of intermediate 73-1: The synthesis method is the same as that of intermediate 1-1, yielding intermediate 73-1 (yield: 82.8%).

[0150] Synthesis of compound 73: The synthesis method was the same as that for intermediate 1-1, yielding compound 73 (yield: 76.2%).

[0151] Mass spectrometry: C39H35N5, theoretical value: 573.29, measured value: 573.33. 1H-NMR (400MHz, CDCl3) (ppm) δ=0.95~0.97 (12H, d), 1.21~1.30 (2H, m), 1.47~1.55 (2H, m), 4.74~4.76 (1H, s), 7.09~7.22 (8H, m), 7.38~7.42 (2H, m), 7.50~7.54 (2H, m), 7.68~7.70 (2H, s), 8.17~8.21 (2H, m), 8.54~8.56 (2H, m).

[0152] Encapsulation film examples

[0153] The preparation method of the encapsulating film includes the following steps:

[0154] The matrix material, UV conversion agent, photoinitiator, light stabilizer, crosslinking agent, co-crosslinking agent, antioxidant, and silane coupling agent are mixed evenly in a mixing tank and then fed into a twin-screw extruder. The mixture is kneaded at 90°C and 200 rpm. After that, it is plasticized, extruded, stretched, drawn, and wound in a casting machine to obtain a UV conversion encapsulation film with a thickness of 0.5 mm.

[0155] Example 1 of encapsulating film

[0156] This embodiment provides an ultraviolet light conversion encapsulating film, prepared using the above-described preparation method. The base material is 100g of ethylene-vinyl acetate copolymer, the ultraviolet light converter is 0.1g of compound 1, the photoinitiator is 1g of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butanone, the light stabilizer is 0.1g of bis-2,2,6,6-tetramethylpiperidinol sebacate, the crosslinking agent is 0.5g of 2-ethylhexyl carbonate tert-butyl peroxide, the co-crosslinking agent is 0.5g of N,N′-m-phenylbismaleimide, the antioxidant is 0.05g of tri(nonylphenyl) phosphite, and the silane coupling agent is 0.2g of 3-thiopropyltriethoxysilane.

[0157] Encapsulation film Examples 2-9:

[0158] Encapsulating films Example 2-Example 9 were prepared using a method similar to that used in Encapsulating Film Example 1, except that compound 1 in Encapsulating Film Example 1 was replaced with the compounds in Table 1.

[0159] Comparative Examples of Encapsulating Films 1-3:

[0160] Comparative Examples 1-3 of encapsulating films were prepared using a method similar to that used in Example 1 of the encapsulating film, except that compound 1 in Example 1 of the encapsulating film was replaced with Ref1, Ref2, and Ref3, respectively.

[0161]

[0162] Test case

[0163] Performance tests were conducted on the ultraviolet light conversion encapsulating films obtained in the examples and comparative examples of encapsulating films:

[0164] The transmittance test standard is in accordance with GB / T29848-2018. The transmittance test is conducted using a specific ultraviolet-visible spectrophotometer (PerkinElmer LAMBDA950); the test is performed in the visible light band.

[0165] UV aging resistance test: Tested according to IEC 61215 standard. Test conditions: Sample area 12cm*6cm, irradiance 120W / m². 2 The test was conducted for 1440 hours under the conditions of 85℃ and 85% humidity, and the decay rate compared to the initial brightness was measured.

[0166] Photovoltaic modules including encapsulating film examples and comparative examples were tested for photoelectric conversion efficiency. The photovoltaic module was prepared by stacking photovoltaic glass, ultraviolet light conversion encapsulating film, solar cells, ultraviolet light conversion encapsulating film, and photovoltaic backsheet neatly, and placing them in a laminator for lamination at 100°C for 20 minutes at a lamination pressure of 60 kPa. After lamination, the modules were removed and cooled to obtain the photovoltaic module. (The two ultraviolet light conversion encapsulating films in the same photovoltaic module are of the same type).

[0167] Photovoltaic conversion efficiency test: A standard sunlight beam was emitted using a solar simulator for testing (spectral AM 1.5G, incident power 100mW / cm²). 2 (Temperature 25℃).

[0168] The test results are shown in Table 1.

[0169] The method for calculating the photoelectric conversion efficiency improvement rate in Table 1 is as follows: the photoelectric conversion efficiency of Comparative Example 1 of the encapsulating film is taken as the comparison standard of 100%, and the photoelectric conversion efficiency of the other encapsulating films is compared with it to calculate the improvement rate.

[0170] Photoelectric conversion efficiency improvement % = (Photoelectric conversion efficiency of the encapsulating film in the current example - Photoelectric conversion efficiency of the encapsulating film in Comparative Example 1) / Photoelectric conversion efficiency of the encapsulating film in Comparative Example 1 × 100%

[0171] Table 1

[0172]

[0173] The results above demonstrate that the organic compounds provided by this invention, when added to the encapsulant film, particularly when used as an ultraviolet light conversion encapsulant film in solar cell modules, offer the advantage of high visible light transmittance. They exhibit good absorption of ultraviolet light and can convert it into visible light, thereby significantly improving the light conversion efficiency of solar photovoltaic modules.

[0174] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. An organic compound containing a benzotriazole structure, characterized in that, The organic compound has the structure shown in formula (I): In equation (I), L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-20 Alkyl groups, where n is an integer from 1 to 20, and m is an integer from 1 to 20; R1 is selected from H and C. 1-20 alkyl, C 1-20 alkoxy, unsubstituted or C 1-6 At least one group in the alkyl group substituted with C 5-12 Any one of the aromatic groups; R4 is H or -C(R2)(R3)-CH3; R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H; Alternatively, the two R3s in formula (I) can cyclize together to form a 5-6 saturated carbon ring.

2. The organic compound containing a benzotriazole structure according to claim 1, characterized in that, In equation (I), L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10; R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups; R4 is H or -C(R2)(R3)-CH3; R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H; Alternatively, the two R3s in formula (I) can cyclize together to form a 5-6 saturated carbon ring.

3. The organic compound containing a benzotriazole structure according to claim 1 or 2, characterized in that, The organic compound represented by formula (I) is selected from any one of the following:

4. The organic compound containing a benzotriazole structure according to claim 1 or 2, characterized in that, In equation (I), L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10; R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups; R4 is H; R2 and R3 are each independently selected from H and C. 1-8 Alkyl groups, and R2 and R3 are not both H; Preferably, the organic compound represented by formula (I) is selected from any one of the following:

5. The organic compound containing a benzotriazole structure according to claim 1 or 2, characterized in that, In equation (I), L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10; R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups; R4 is -C(R2)(R3)-CH3; R2 and R3 are each independently selected from H and C. 1-12 Alkyl groups, and R2 and R3 are not both H; Preferably, the organic compound represented by formula (I) is selected from any one of the following:

6. The organic compound containing a benzotriazole structure according to claim 1 or 2, characterized in that, In equation (I), L may or may not exist; if L is present, it is selected from -(CH2). n -、-(CHR L ) m -, -C(CH3)(CH3)-, or at least one linking group formed by removing any two leaving H atoms from benzene, R L C 1-12 Alkyl groups, where n is an integer from 1 to 10, and m is an integer from 1 to 10; R1 is selected from H and C. 1-10 alkyl, C 1-10 Any one of alkoxy or phenyl groups; R4 is -C(R2)(R3)-CH3; R2 is selected from H and C. 1-12 Alkyl groups; The two R3s in formula (I) cyclize together to form a 5-6 saturated carbon ring; Preferably, the organic compound represented by formula (I) is selected from any one of the following:

7. The use of the organic compound containing a benzotriazole structure as described in any one of claims 1-6 in encapsulating adhesives; Preferably, the encapsulating adhesive is an ultraviolet light conversion encapsulating adhesive.

8. A composition for encapsulating adhesive, characterized in that, The composition contains 100 parts by weight of matrix material, 0.005-2 parts by weight of ultraviolet light converter, 0-2 parts by weight of photoinitiator, 0.1-1 parts by weight of light stabilizer, 0-3 parts by weight of crosslinking agent, 0-2 parts by weight of co-crosslinking agent, 0.05-1 parts by weight of antioxidant and 0.2-1 parts by weight of silane coupling agent; The ultraviolet light converter is selected from the organic compounds containing the benzotriazole structure as described in any one of claims 1-6.

9. The composition for encapsulating adhesive according to claim 8, characterized in that, The matrix material is an ethylene-vinyl acetate copolymer; Preferably, the vinyl acetate structural unit content in the ethylene-vinyl acetate copolymer used as the matrix material is 25-35 wt%, the melt index of the ethylene-vinyl acetate copolymer is 0.1-40 g / min, the melting point is 40-90 °C, and the light transmittance is ≥90%.

10. A method for preparing an encapsulating adhesive, characterized in that, The method includes: curing material I containing each component of the composition to obtain the encapsulating adhesive; The composition is the encapsulating adhesive composition as described in claim 8 or 9.

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