Triazole organic compound and application thereof

Abstract

The invention belongs to the field of light conversion adhesive films, and particularly relates to a triazole organic compound and application thereof. The triazole organic compound has a structure as shown in a formula I, wherein R1, R2 and Ar are defined in the specification. According to the light conversion agent, the light conversion adhesive film composition and the light conversion adhesive film, the range of an absorption spectrum can be adjusted, and the wave band of ultraviolet light can be selectively absorbed. According to the light conversion agent, the light conversion adhesive film composition and the light conversion adhesive film, the range of an emission spectrum can be adjusted, the emission spectrum can be adjusted to an interval range with relatively high EQE (Energy Quality Equation) of HJT (High Junction Test), and the power of a component is improved. The light conversion agent disclosed by the invention has good weather resistance. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the field of light-converting adhesive films, and specifically relates to a triazole organic compound and application thereof. Background Art

[0002] As a clean energy with abundant resources and no need for transportation, solar energy is expected to become an alternative energy source to replace traditional fossil fuels. Therefore, the development of solar energy collection and conversion technology has gradually become the focus of national and social attention. Photovoltaic devices can directly convert solar energy into electrical energy, which is one of the most effective ways to utilize solar energy. So far, the demand for photovoltaic installations around the world continues to increase. The vast majority of photovoltaic devices can only effectively utilize sunlight in the visible and near-infrared bands, and the utilization efficiency of ultraviolet light in sunlight (wavelength less than 400nm) is low. Not only that, the presence of ultraviolet light in sunlight will also reduce the service life of photovoltaic devices, especially for heterojunction (HJT) cells that are expected to replace PERC and TOPCon as the third-generation solar cells.

[0003] The use of wavelength conversion film can not only effectively absorb the ultraviolet light in sunlight to avoid damage to the service life of photovoltaic devices, but also convert ultraviolet light into usable visible light, thereby improving the photoelectric conversion efficiency of photovoltaic devices. At present, although the use of packaging films with ultraviolet absorption function can improve the stability of components, the efficiency of components is seriously reduced. Therefore, some companies have begun to use phosphors with down-conversion functions and disperse them in the film. The film can convert ultraviolet light into visible light, which can not only protect the battery, but also maintain efficient component power output.

[0004] The technical core of the light conversion film lies in the selection of a suitable light conversion agent. The current light conversion agents are mainly divided into inorganic light conversion agents and organic light conversion agents. Compared with inorganic light conversion agents, organic light conversion agents have the advantages of low price, wide variety, and easy performance control. In addition, since the base film of the light conversion film is an organic polymer material, the organic light conversion agent and the base film often show better dispersibility and compatibility, and have less impact on the light transmittance of the light conversion film. Organic light conversion agents are often natural light conversion agent materials. Conventional organic light conversion agents are some down-converting organic luminescent small molecules that can absorb ultraviolet light well and convert it into visible light (generally blue light or sky blue light). However, the stability of existing organic light conversion agents is poor, and the corresponding light conversion film usually has a high water vapor permeability, which greatly reduces the service life of photovoltaic modules.

[0005] There is still a lot of room for improvement in the current light-conversion film. First, the wavelength of light conversion of mass-produced light-conversion films is distributed around 420nm, which is not the wavelength with the highest EQE response of HJT cells. Further increasing the wavelength of light conversion to above 440nm can increase the power of the module; secondly, since the maximum absorption wavelength is around 345nm, a large part of ultraviolet light will still pass through the film to the cell, causing damage to the cell. Summary of the invention

[0006] The purpose of the present invention is to provide a triazole organic compound and application thereof.

[0007] In a first aspect of the present invention, an organic compound is provided, the structure of which is shown in Formula I:

[0008]

[0009] In formula I, Ar is selected from a substituted or unsubstituted C6-C14 arylene group, a substituted or unsubstituted 5-14 membered heteroarylene group having one or more heteroatoms selected from N, O, Se, and S;

[0010] R1 and R2 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy;

[0011] The term "substituted" refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of halogen, C1-C20 alkyl, (-C1-C6 alkylene-O) n - C1-C6 alkyl, C1-C20 alkoxy, n is an integer selected from 1-10.

[0012] In one or more embodiments, Ar is selected from substituted or unsubstituted C6-C10 arylene, substituted or unsubstituted 5-12 membered heteroarylene having one or more heteroatoms selected from N, O, Se, S, wherein the "substituted" refers to being substituted by a group selected from halogen, C1-C20 alkyl, C1-C20 alkoxy.

[0013] In one or more embodiments, Ar is selected from: Wherein, each X is independently selected from O, S or Se, each R is independently selected from H, halogen, C1-C10 alkyl, C1-C10 alkoxy, and Ar also has two sites for connecting with other structures of organic compounds.

[0014] In one or more embodiments, Ar is selected from: Wherein, each X is independently selected from O, S, and Se, each R is independently selected from H, halogen, C1-C6 alkyl, and C1-C6 alkoxy, and Ar also has two sites for connecting with other structures of organic compounds.

[0015] In one or more embodiments, Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted 5-membered heteroarylene, substituted or unsubstituted 10-membered heteroarylene.

[0016] In one or more embodiments, the 5-membered heteroarylene group is selected from furanyl, pyrroleyl, thienyl, and selenopheneyl groups; and / or, the 10-membered heteroarylene group is selected from difuranyl, dithienyl, and diselenopheneyl groups.

[0017] In one or more embodiments, Ar is selected from phenylene optionally substituted with substituents selected from halogen, C1-C6 alkoxy, C1-C6 alkyl, and 5-10 membered heteroarylene optionally substituted with substituents selected from halogen, C1-C6 alkoxy, and C1-C6 alkyl.

[0018] In one or more embodiments, the 5-10 membered heteroarylene group is selected from furanyl, pyrroleyl, thienyl, and dithienyl.

[0019] In one or more embodiments, R1 and R2 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, wherein "substituted" means that one or more hydrogen atoms on the group are replaced by a substituent selected from the group consisting of C1-C10 alkyl, (-C1-C4 alkylene-O) n - C1-C4 alkyl, C1-C10 alkoxy, n is an integer selected from 1-5.

[0020] In one or more embodiments, R1 and R2 are each independently selected from "*" refers to the position where the group is attached to other structures of the organic compound.

[0021] In one or more embodiments, R1 and R2 are each independently C1-C6 alkyl optionally substituted with C1-C6 alkoxy.

[0022] In one or more embodiments, the organic compound is selected from the group consisting of:

[0023]

[0024] The second aspect of the present invention provides use of the organic compound described in the first aspect of the present invention as a light conversion agent.

[0025] The third aspect of the present invention provides a light conversion adhesive film composition, wherein the light conversion adhesive film composition comprises the organic compound described in the first aspect of the present invention.

[0026] In one or more embodiments, the light conversion adhesive film composition further includes a base resin.

[0027] In one or more embodiments, the base resin is selected from one or more of ethylene-vinyl acetate copolymer, ethylene-octene copolymer, polyvinyl butyral, and silicone polymer resin.

[0028] In one or more embodiments, the mass fraction of the organic compound in the light conversion adhesive film composition is 0.01-5 wt %.

[0029] In one or more embodiments, the light conversion adhesive film composition further includes one or more of an antioxidant, a coupling agent, and an initiator.

[0030] The fourth aspect of the present invention provides a light conversion adhesive film prepared using the light conversion adhesive film composition described in the third aspect of the present invention.

[0031] A fifth aspect of the present invention provides a photovoltaic module, wherein the photovoltaic module comprises the light conversion adhesive film described in the fourth aspect of the present invention.

[0032] In one or more embodiments, the photovoltaic module is selected from one or more of a crystalline silicon cell, a perovskite cell, and a perovskite / crystalline silicon tandem cell.

[0033] The present invention has the following beneficial effects:

[0034] (1) The light conversion agent, light conversion adhesive film composition and light conversion adhesive film synthesis method of the present invention are simple and have low raw material cost.

[0035] (2) The light conversion agent, light conversion adhesive film composition and light conversion adhesive film of the present invention can adjust the range of the absorption spectrum and selectively absorb the wavelength band of ultraviolet light.

[0036] (3) The light conversion agent, light conversion adhesive film composition and light conversion adhesive film of the present invention can adjust the range of the emission spectrum, red-shift the absorption band and emission band of the light conversion agent, adjust the emission spectrum to the range of relatively high EQE of HJT, and improve the power of the component.

[0037] (4) The light conversion agent of the present invention has good weather resistance (ie, a higher light conversion efficiency retention rate).

[0038] (5) The light conversion agent of the present invention can effectively improve the ability of the light conversion film to convert ultraviolet light into visible light by introducing two triazole structures. DETAILED DESCRIPTION

[0039] In order to enable those skilled in the art to understand the characteristics and effects of the present invention, the following is a general description and definition of the terms and expressions mentioned in the specification and claims. Unless otherwise specified, all technical and scientific terms used in the text are the common meanings understood by those skilled in the art for the present invention. In the event of a conflict, the definition in this specification shall prevail.

[0040] The theories or mechanisms described and disclosed herein, whether correct or incorrect, should not limit the scope of the present invention in any way, that is, the present invention can be implemented without being limited by any specific theory or mechanism.

[0041] Herein, “comprising”, “including”, “containing” and similar terms encompass the meanings of “consisting essentially of” and “consisting of”. For example, when “A comprises B and C” is disclosed herein, “A consists essentially of B and C” and “A consists of B and C” should be deemed to be disclosed herein.

[0042] In this article, all features such as values, quantities, contents and concentrations defined in the form of numerical ranges or percentage ranges are only for brevity and convenience. Accordingly, the description of numerical ranges or percentage ranges should be considered to have included and specifically disclosed all possible secondary ranges and individual values ​​within the range (including integers and fractions).

[0043] In this document, unless otherwise specified, percentage refers to mass percentage and ratio refers to mass ratio.

[0044] Herein, when describing embodiments or examples, it should be understood that they are not used to limit the present invention to these embodiments or examples. On the contrary, all substitutes, improvements and equivalents of the methods and materials described in the present invention can be included in the scope limited by the claims.

[0045] In this document, in order to make the description concise, not all possible combinations of various technical features in various embodiments or examples are described. Therefore, as long as there is no contradiction in the combination of these technical features, the various technical features in various embodiments or examples can be combined arbitrarily, and all possible combinations should be considered to be within the scope of this specification.

[0046] As used herein, "alkyl" refers to a straight or branched monovalent saturated hydrocarbon group having a specified number of carbon atoms, and specific alkyl groups are those having 1 to 20 carbon atoms ("C1-C20 alkyl"), usually containing 1-16 carbon atoms (C1-C16 alkyl), preferably containing 1-10 carbon atoms (C1-C10 alkyl), and more preferably containing 1-6 carbon atoms (C1-C6 alkyl). Examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and the like. In some embodiments, the alkyl group suitable for the present invention can be a C1-C20 alkyl group, such as a C1 alkyl group, a C2 alkyl group, a C3 alkyl group, a C4 alkyl group, a C5 alkyl group, a C6 alkyl group, a C7 alkyl group, a C8 alkyl group, a C9 alkyl group, a C10 alkyl group, a C11 alkyl group, a C12 alkyl group, a C13 alkyl group, a C14 alkyl group, a C15 alkyl group, a C16 alkyl group, a C17 alkyl group, a C18 alkyl group, a C19 alkyl group, and a C20 alkyl group.

[0047] As used herein, "alkylene" refers to a group that is the same as an alkyl group but has a divalent radical. Specific alkylene groups have 1 to 6 carbon atoms (C 1-6 Alkylene), more preferably containing 1 to 4 carbon atoms (C 1-4 Examples of the alkylene group include a methylene group (-CH2-), an ethylene group (-CH2CH2-), a propylene group (-CH2CH2CH2-), a butylene group (-CH2CH2CH2CH2-), and the like.

[0048] As used herein, "alkoxy" refers to alkyl-O-, and preferred alkoxy is C1-C20 alkoxy, such as C1-C16 alkoxy, C1-C10 alkoxy, C1-C8 alkoxy, C1-C6 alkoxy, C1-C4 alkoxy, which includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, sec-butoxy, n-pentoxy, n-hexyloxy, 1,2-dimethylbutoxy and the like.

[0049] As used herein, "halo" or "halogen" refers to an element of Group 17 with an atomic number of 9 to 85. "Halogen" or "halogen atom" refers to F, Cl, Br, I. "Halogenated" means substituted with an atom selected from F, Cl, Br, I.

[0050] As used herein, "aryl" refers to an unsaturated aromatic carbocyclic monovalent group having a single ring (e.g., phenyl) or multiple fused rings (e.g., naphthyl or anthracenyl), wherein the fused rings may or may not be aromatic. In one variation, the aryl group contains 6 to 14 ring carbon atoms ("C6-C14 aryl"), preferably C6-C10 aryl. An aryl group having more than one ring and at least one of which is a non-aromatic ring may be attached to the parent structure at an aromatic ring position or at a non-aromatic ring position. Examples of aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, indenyl, azulenyl, biphenyl, biphenylene, fluorenyl. As used herein, "arylidene" refers to an unsaturated aromatic carbocyclic divalent group having a single ring (e.g., phenyl) or multiple fused rings (e.g., naphthyl or anthracenyl), wherein the fused rings may or may not be aromatic. Arylene is a divalent group of aryl. In one variation, the arylene group contains 6 to 14 ring carbon atoms ("C6-C14 arylene"), with C6-C10 arylene being preferred.

[0051] As used herein, "heteroaryl" refers to a monovalent group containing 5-14, preferably 5-10 ring atoms, and having 6, 10 or 14 π electrons shared on the ring system. As used herein, "heteroarylene" refers to a divalent group containing 5-14, preferably 5-10 ring atoms, and having 6, 10 or 14 π electrons shared on the ring system. The ring atoms contained in the heteroaryl or heteroarylene are carbon atoms and heteroatoms selected from N, O, S, and Se. In the present invention, the preferred heteroaryl is a heteroaryl containing N, S or O atoms, and more preferably a heteroaryl containing N or S atoms. Examples of heteroaryl groups include triazolyl, thienyl, furanyl, pyranyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, benzimidazolyl, dibenzothienyl, dibenzopyridinyl, pyrazolopyrimidinyl, and the like.

[0052] The present invention provides an organic compound, the structure of which is shown in Formula I:

[0053]

[0054] In formula I, Ar is selected from a substituted or unsubstituted C6-C14 arylene group, a substituted or unsubstituted 5-14 membered heteroarylene group having one or more heteroatoms selected from N, O, Se, and S;

[0055] R1 and R2 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy;

[0056] The term "substituted" refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of halogen, C1-C20 alkyl, (-C1-C6 alkylene-O)n - C1-C6 alkyl, C1-C20 alkoxy, n is an integer selected from 1-10.

[0057] In some embodiments, Ar is selected from substituted or unsubstituted C6-C10 arylene, substituted or unsubstituted 5-12 membered heteroarylene having one or more heteroatoms selected from N, O, Se, S, and the "substituted" refers to substitution with a group selected from halogen, C1-C20 alkyl, and C1-C20 alkoxy.

[0058] In some embodiments, Ar is selected from: Wherein, each X is independently selected from O, S or Se, each R is independently selected from H, halogen, C1-C10 alkyl, C1-C10 alkoxy, and Ar also has two sites for connecting with other structures of organic compounds. Preferably, Ar is selected from: Wherein, each X is independently selected from O, S, and Se, each R is independently selected from H, halogen, C1-C6 alkyl, and C1-C6 alkoxy, and Ar also has two sites for connecting with other structures of organic compounds.

[0059] In some embodiments, Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted 5-membered heteroarylene, substituted or unsubstituted 10-membered heteroarylene. Preferably, the 5-membered heteroarylene is selected from furanyl, pyrroleyl, thienyl, selenopheneyl; and / or, the 10-membered heteroarylene is selected from bifuranyl, bithienyl, biselenopheneyl.

[0060] In some embodiments, Ar is selected from phenylene optionally substituted by a substituent selected from halogen, C1-C6 alkoxy, C1-C6 alkyl; 5-10 membered heteroarylene optionally substituted by a substituent selected from halogen, C1-C6 alkoxy, C1-C6 alkyl. Preferably, the 5-10 membered heteroarylene is selected from furanyl, pyrroleyl, thienyl, dithienyl.

[0061] In some embodiments, R1 and R2 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkoxy, wherein "substituted" means that one or more hydrogen atoms on the group are replaced by a substituent selected from the group consisting of C1-C10 alkyl, (-C1-C4 alkylene-O) n - C1-C4 alkyl, C1-C10 alkoxy, n is an integer selected from 1-5.

[0062] In some embodiments, R1 and R2 are each independently selected from "*" refers to the position where the group is attached to other structures of the organic compound.

[0063] In some embodiments, R1 and R2 are each independently C1-C6 alkyl optionally substituted with C1-C6 alkoxy.

[0064] In some embodiments, the organic compound is selected from the group consisting of:

[0065] The present invention also provides the use of the organic compound of the present invention as a light conversion agent. The organic compound of the present invention as a light conversion agent can play a role in regulating the absorption wavelength and emission wavelength of existing light conversion agents, and the use of the organic compound of the present invention as a light conversion agent can improve the light conversion efficiency and weather resistance of the light conversion adhesive film (improve the light conversion efficiency retention rate).

[0066] The present invention also provides a light-converting adhesive film composition, which includes the organic compound of the present invention. In some embodiments, the light-converting adhesive film composition also includes a base resin. Preferably, the base resin is selected from one or more of ethylene-vinyl acetate copolymer (EVA), ethylene-octene copolymer (POE), polyvinyl butyral (PVB), and silicone polymer resin. In some embodiments, in the light-converting adhesive film composition, the mass fraction of the organic compound is 0.01-5wt%.

[0067] The light conversion adhesive film composition further includes one or more of an antioxidant, a coupling agent, and an initiator. In some embodiments, the light conversion adhesive film composition further includes an antioxidant; preferably, the antioxidant is selected from antioxidant 152. In some embodiments, the light conversion adhesive film composition further includes a coupling agent; preferably, the coupling agent is selected from silane coupling agent KH570. In some embodiments, the light conversion adhesive film composition further includes an initiator; preferably, the initiator is selected from TBEC.

[0068] The present invention also provides a light-converting adhesive film prepared using the light-converting adhesive film composition of the present invention. In some embodiments, the light-converting adhesive film composition of the present invention is heated and melted, and stretched into a film by conventional equipment in the field of light-converting adhesive films. Preferably, the absorption wavelength of the light-converting adhesive film of the present invention is 280-450nm; preferably, the absorption wavelength of the light-converting adhesive film of the present invention is 320-400nm. Preferably, the emission wavelength of the light-converting adhesive film of the present invention is 400-600nm; preferably, the emission wavelength of the light-converting adhesive film of the present invention is 410-450nm. Preferably, the maximum absorption wavelength of the light-converting adhesive film of the present invention is 350-380nm. Preferably, the maximum emission wavelength of the light-converting adhesive film of the present invention is 410-445nm.

[0069] The present invention also provides a photovoltaic module, the photovoltaic module comprising the light conversion adhesive film of the present invention. Preferably, the photovoltaic module is selected from one or more of crystalline silicon cells, perovskite cells, and perovskite / crystalline silicon stacked cells.

[0070] The present invention also provides the use of the organic compound of the present invention in the preparation of a light-converting adhesive film composition, a light-converting adhesive film and a photovoltaic module.

[0071] The present invention also provides application of the light conversion adhesive film composition of the present invention in preparing light conversion adhesive films and photovoltaic modules.

[0072] The present invention also provides application of the light conversion adhesive film of the present invention in preparing photovoltaic modules.

[0073] The present invention also provides the use of the organic compound of the present invention and the light conversion adhesive film composition of the present invention in improving the absorption wavelength and emission wavelength of the light conversion adhesive film.

[0074] The present invention also provides the use of the organic compound of the present invention and the light conversion adhesive film composition of the present invention in improving the light conversion efficiency and / or improving the weather resistance of the light conversion adhesive film. Specifically, the improvement of the weather resistance of the light conversion adhesive film is to improve the light conversion efficiency retention rate of the light conversion adhesive film after aging.

[0075] The present invention will be further described below in conjunction with specific examples. It should be understood that these examples are only used to illustrate the present invention and are not intended to limit the scope of the present invention. The experimental methods in the following examples without specifying specific conditions are usually based on conventional conditions or the conditions recommended by the manufacturer. Unless otherwise stated, percentages and parts are calculated by weight.

[0076] Herein, the organic silicon polymer resin is Dow DC184 organic silicon material.

[0077] Example 1

[0078] In parts by weight, the light-converting adhesive film composition includes 99 parts by weight of ethylene-vinyl acetate copolymer (3-5 mm round particles), 0.2 parts by weight of triazole compound, 0.3 parts by weight of TBEC, 0.3 parts by weight of silane coupling agent KH570, and 0.2 parts by weight of antioxidant 152, wherein the structural formula of the triazole compound is as follows:

[0079]

[0080] The preparation method is as follows: 3 mmol of 4-bromobenzotriazole derivative and 1 mmol of 1,4-phenyldiboronic acid are dissolved in 10 mL of 1,4-dioxane, 2 mmol of potassium carbonate and 1 mL of deionized water are added, and then the reaction environment is replaced with an inert gas (argon), heated to 95°C, reacted for 24 hours, cooled to room temperature, quenched with water and extracted with dichloromethane, spin-dried, and the target product is extracted using column chromatography, and the target product is a white powder.

[0081] 1 H NMR (500MHz, Chloroform-d) δ = 8.05 (dd, J = 7.5, 1.5, 1H), 7.78 (dd, J = 7.5, 1.5, 1H), 7.57 (s, 2H),7.51(t,J=7.5,1H),3.88(d,J=7.0,2H),2.33(dp,J=13.7,6.9,1H),1.04(d,J=6.8,6H).

[0082] Example 2

[0083] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-octene copolymer (3-5 mm round particles) and 0.5 parts by weight of triazole compound, wherein the structural formula of the triazole compound is as follows:

[0084]

[0085] The preparation method is as follows: repeat the method of Example 1, and use 1,4-dimethoxy-2,5-phenylenediboronic acid to replace 1,4-phenylenediboronic acid.

[0086] 1 H NMR (500MHz, Chloroform-d) δ = 8.08 (dd, J = 7.5, 1.5, 1H), 7.68 (dd, J = 7.5, 1.5, 1H), 7.44 (t, J = 7.5, 1H),7.19(s,1H),3.86(s,2H),3.76(d,J=7.0,2H),2.32(dp,J=13.6,6.8,1H),1.04(d,J=6.8,6H).

[0087] Example 3

[0088] In parts by weight, the light-converting adhesive film composition includes 99 parts by weight of an organic silicon polymer resin (3-5 mm round particles), 0.5 parts by weight of a triazole compound, and 0.5 parts by weight of an antioxidant 152, wherein the triazole compound has the following structural formula:

[0089]

[0090] The preparation method is as follows: 3 mmol of 4-bromobenzotriazole derivative and 1 mmol of 2,5-thiophenediboronic acid are dissolved in 10 mL of 1,4-dioxane, 2 mmol of potassium carbonate and 1 mL of deionized water are added, and then the reaction environment is replaced with an inert gas (argon), heated to 95°C, reacted for 24 hours, cooled to room temperature, quenched with water and extracted with dichloromethane, spin-dried, and the target product is extracted using column chromatography, and the target product is a white powder.

[0091] 1 H NMR (500MHz, Chloroform-d) δ = 7.83 (dd, J = 7.5, 1.5, 1H), 7.77–7.71 (m, 2H), 7.48 ( t,J=7.4,1H),3.88(d,J=7.0,2H),2.35(dp,J=13.6,6.9,1H),1.04(d,J=6.8,6H).

[0092] Example 4

[0093] In parts by weight, the light-converting adhesive film composition includes 99 parts by weight of an organic silicon polymer resin (3-5 mm round particles), 0.5 parts by weight of a triazole compound, and 0.5 parts by weight of an antioxidant 152, wherein the triazole compound has the following structural formula:

[0094]

[0095] The preparation method is as follows: 3 mmol of 4-bromobenzotriazole derivative and 1 mmol of 2,2'-bithiophene diboronic acid are dissolved in 10 mL of 1,4-dioxane, 2 mmol of potassium carbonate and 1 mL of deionized water are added, and then the reaction environment is replaced with an inert gas (argon), heated to 95°C, reacted for 24 hours, cooled to room temperature, quenched with water and extracted with dichloromethane, spin-dried, and the target product is extracted using column chromatography, and the target product is a white powder.

[0096] 1 H NMR (500MHz, Chloroform-d) δ = 7.82 (dd, J = 7.5, 1.5, 1H), 7.75 (dd, J = 7.5, 1.5, 1H), 7.57–7.49 ( m,2H),7.41(d,J=7.5,1H),3.88(d,J=7.0,2H),2.35(dp,J=13.6,6.9,1H),1.05(d,J=6.8,6H).

[0097] Example 5

[0098] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-octene copolymer (3-5 mm round particles) and 0.5 parts by weight of triazole compound, wherein the structural formula of the triazole compound is as follows:

[0099]

[0100] The preparation method is as follows: 3 mmol of 4-bromobenzotriazole derivative and 1 mmol of 2,5-furandiboronic acid are dissolved in 10 mL of 1,4-dioxane, 2 mmol of potassium carbonate and 1 mL of deionized water are added, and then the reaction environment is replaced with an inert gas (argon), heated to 95°C, reacted for 24 hours, cooled to room temperature, quenched with water and extracted with dichloromethane, spin-dried, and the target product is extracted using column chromatography, and the target product is a white powder.

[0101] 1 H NMR(500MHz,Chloroform-d)δ8.03–7.92(m,2H),7.50(dd,J=10.4,7.7Hz,1H),3 .96(d,J=4.2Hz,2H),2.28(dpd,J=11.7,7.5,3.1Hz,1H),1.07(d,J=7.4Hz,6H).

[0102] Example 6

[0103] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-vinyl acetate copolymer (3-5 mm round particles) and 0.5 parts by weight of a triazole compound, wherein the structural formula of the triazole compound is as follows:

[0104]

[0105] The preparation method is as follows: 3 mmol of 4-bromobenzotriazole derivative and 1 mmol of 2,5-nitromethylpyrrole diboronic acid are dissolved in 10 mL of 1,4-dioxane, 2 mmol of potassium carbonate and 1 mL of deionized water are added, and then the reaction environment is replaced with an inert gas (argon), heated to 95°C, reacted for 24 hours, cooled to room temperature, quenched with water and extracted with dichloromethane, spin-dried, and the target product is extracted using column chromatography, and the target product is a white powder.

[0106] 1H NMR(500MHz,Chloroform-d)δ7.95(ddd,J=9.0,7.9,1.1Hz,2H),7.57(dd,J=8.4,7.7Hz,1H),6.55(s ,1H),3.97(d,J=4.4Hz,2H),3.70(s,1H),2.28(dpd,J=11.7,7.5,3.1Hz,1H),1.07(d,J=7.4Hz,5H).

[0107] Example 7

[0108] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-octene copolymer (3-5 mm round particles) and 0.5 parts by weight of triazole compound, wherein the structural formula of the triazole compound is as follows:

[0109]

[0110] The preparation method is as follows: repeat the method of Example 1, and use 1,4-dimethyl-2,5-phenylenediboronic acid to replace 1,4-phenylenediboronic acid.

[0111] 1 H NMR(500MHz,Chloroform-d)δ8.02–7.92(m,2H),7.73(s,1H),7.57(dd,J=9.0,7.6Hz, 1H), 3.97 (d, J = 4.4Hz, 2H), 2.28 (dpd, J = 11.7, 7.5, 3.1Hz, 1H), 1.07 (d, J = 7.4Hz, 5H).

[0112] Example 8

[0113] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of an organic silicon polymer resin (3-5 mm round particles) and 0.5 parts by weight of a triazole compound, wherein the structural formula of the triazole compound is as follows:

[0114]

[0115] The preparation method is as follows: repeat the method of Example 1, and use 1,4-dichloro-2,5-phenylenediboronic acid to replace 1,4-phenylenediboronic acid.

[0116] 1H NMR(500MHz,Chloroform-d)δ8.03–7.96(m,2H),7.90(s,1H),7.62(dd,J=9.0,7.6Hz, 1H), 3.97 (d, J = 4.4Hz, 2H), 2.28 (dpd, J = 11.7, 7.5, 3.1Hz, 1H), 1.07 (d, J = 7.4Hz, 5H).

[0117] Example 9

[0118] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-octene copolymer (3-5 mm round particles) and 0.5 parts by weight of triazole compound, wherein the structural formula of the triazole compound is as follows:

[0119]

[0120] The preparation method is as follows: repeat the method of Example 2, and use an alkoxy-substituted 4-bromobenzotriazole derivative to replace the original alkyl-substituted 4-bromobenzotriazole derivative.

[0121] 1 H NMR (500MHz, Chloroform-d) δ7.99–7.90(m,2H),7.56(dd,J=9.0,7.7Hz,1H),5.35(s,2H),3.86(s,2H),3.71(q,J=5.6Hz,2H),1.22(t,J=5.6Hz,3H).

[0122] Comparative Example 1

[0123] In parts by weight, the light-converting adhesive film composition includes 99.5 parts by weight of ethylene-vinyl acetate copolymer (3-5 mm round particles) and 0.5 parts by weight of a triazole compound, wherein the triazole compound has the following structural formula and can be synthesized using existing methods in the art:

[0124]

[0125] Preparation of light-converting film

[0126] The materials are mixed according to the formula of the light-converting adhesive film composition of Examples 1-9, and then a casting machine is used (the working conditions of the casting machine: the temperature of zone 1 is 90°C, the temperatures of zones 2 and 3 are 100°C, the temperature of zone 4 is 90°C, the temperature of the film head is 90°C, the rotation speed is 50rpm, and the traction speed controls the film thickness to 0.5mm) for film casting.

[0127] Test Case

[0128] The test method of the maximum absorption wavelength is: use an ultraviolet spectrophotometer, set the test range to 280-500nm, and the step length to 5nm, and perform an absorption test on the prepared light conversion film. The wavelength corresponding to the maximum absorption is the maximum absorption wavelength.

[0129] The test method for the maximum emission wavelength is: use a fluorescence spectrometer, set the excitation wavelength according to the maximum absorption wavelength, set the fluorescence test range to 280-500nm, with a step length of 5nm, and perform a fluorescence spectrum test on the prepared light-converting adhesive film. The wavelength corresponding to the maximum fluorescence is the maximum emission wavelength.

[0130] Test method for light conversion efficiency: Test the fluorescence quantum yield of the prepared light conversion film. Refer to the "General Test Method for Absolute Measurement of Photoluminescence Quantum Efficiency of Fluorescent Materials" for the test method.

[0131] Light conversion efficiency retention rate: in UV aging box (energy density is 200W / m 2 ) in which the light-converting film is irradiated with a cumulative irradiation of 60 kWh / m 2 After that, the light conversion efficiency is tested again and compared with the initial light conversion efficiency before aging, the light conversion efficiency retention rate of the light conversion film can be obtained.

[0132] The maximum absorption wavelength, maximum emission wavelength and light conversion efficiency were tested using the above method. The results are shown in Table 1.

[0133] Table 1

[0134]

[0135]

[0136] Compared with the light conversion adhesive film prepared from the light conversion adhesive film composition of comparative example 1, the absorption wavelength and emission wavelength of the light conversion adhesive film can be red-shifted without affecting the light conversion efficiency, and the light conversion efficiency retention rate of the light conversion adhesive film after aging is maintained at more than 97%. The present invention utilizes the conjugated structure of bistriazole to enhance the electron delocalization characteristics of the light conversion agent molecule and increase the conjugated characteristics of the molecule, thereby reducing the molecular band gap of the light conversion agent and red-shifting its absorption spectrum and fluorescence spectrum.

Claims

1. An organic compound, characterized in that The structure of the organic compound is shown in Formula I: In formula I, Ar is selected from a substituted or unsubstituted C6-C14 arylene group, a substituted or unsubstituted 5-14 membered heteroarylene group having one or more heteroatoms selected from N, O, Se, and S; R1 and R2 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy; The term "substituted" refers to the substitution of one or more hydrogen atoms on the group by a substituent selected from the group consisting of halogen, C1-C20 alkyl, (-C1-C6 alkylene-O) n - C1-C6 alkyl, C1-C20 alkoxy, n is an integer selected from 1-10.

2. The organic compound according to claim 1, characterized in that Ar is selected from substituted or unsubstituted C6-C10 arylene, substituted or unsubstituted 5-12 membered heteroarylene having one or more heteroatoms selected from N, O, Se, S, wherein the "substituted" means substituted by a group selected from halogen, C1-C20 alkyl, C1-C20 alkoxy.

3. The organic compound according to claim 1, characterized in that Ar is selected from: Wherein, each X is independently selected from O, S, and Se, each R is independently selected from H, halogen, C1-C10 alkyl, and C1-C10 alkoxy, and Ar also has two sites for connecting with other structures of the organic compound.

4. The organic compound according to claim 1, characterized in that Ar is selected from: Wherein, each X is independently selected from O, S, and Se, each R is independently selected from H, halogen, C1-C6 alkyl, and C1-C6 alkoxy, and Ar also has two sites for connection with other structures of the organic compound.

5. The organic compound according to claim 1, characterized in that Ar is selected from substituted or unsubstituted phenylene, substituted or unsubstituted 5-membered heteroarylene, and substituted or unsubstituted 10-membered heteroarylene.

6. The organic compound according to claim 5, characterized in that The 5-membered heteroarylene group is selected from a furanyl group, a pyrroleyl group, a thiopheneyl group, and a selenopheneyl group; and / or the 10-membered heteroarylene group is selected from a difuranyl group, a dithiopheneyl group, and a diselenopheneyl group.

7. The organic compound according to claim 1, characterized in that Ar is selected from phenylene optionally substituted by a substituent selected from halogen, C1-C6 alkoxy, C1-C6 alkyl, and 5-10 membered heteroarylene optionally substituted by a substituent selected from halogen, C1-C6 alkoxy, C1-C6 alkyl.

8. The organic compound according to claim 7, characterized in that The 5-10 membered heteroarylene group is selected from furanyl group, pyrroleyl group, thienyl group and dithienyl group.

9. The organic compound according to claim 1, characterized in that R1 and R2 are each independently selected from substituted or unsubstituted C1-C10 alkyl or substituted or unsubstituted C1-C10 alkoxy, wherein "substituted" means that one or more hydrogen atoms on the group are replaced by a substituent selected from the group consisting of C1-C10 alkyl, (-C1-C4 alkylene-O) n -C1-C4 alkyl, C1-C10 alkoxy group, wherein n is an integer selected from 1-5.

10. The organic compound according to claim 1, characterized in that R1 and R2 are each independently selected from "*" refers to the position where the group is connected to other structures of the organic compound.

11. The organic compound according to claim 1, characterized in that R1 and R2 are each independently a C1-C6 alkyl group optionally substituted by a C1-C6 alkoxy group.

12. The organic compound according to claim 1, characterized in that The organic compound is selected from the group consisting of:

13. Use of the organic compound according to any one of claims 1 to 12 as a light conversion agent.

14. A light conversion adhesive film composition, comprising the organic compound according to any one of claims 1 to 12.

15. The light conversion adhesive film composition according to claim 14, characterized in that: The light conversion adhesive film composition also includes a base resin. 16 . The light conversion adhesive film composition as claimed in claim 15 , wherein the matrix resin is selected from one or more of ethylene-vinyl acetate copolymer, ethylene-octene copolymer, polyvinyl butyral, and silicone polymer resin.

17. The light conversion adhesive film composition according to claim 14, characterized in that: In the light conversion adhesive film composition, the mass fraction of the organic compound is 0.01-5wt%.

18. The light conversion adhesive film composition according to claim 14, characterized in that: The light conversion adhesive film composition further comprises one or more of an antioxidant, a coupling agent, and an initiator.

19. A light conversion adhesive film prepared using the light conversion adhesive film composition according to any one of claims 14 to 18.

20. A photovoltaic module, characterized in that: The photovoltaic module comprises the light-converting adhesive film described in claim 19.

21. The photovoltaic module according to claim 1, characterized in that: The photovoltaic module is selected from one or more of crystalline silicon cells, perovskite cells, and perovskite / crystalline silicon stacked cells.

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