Light conversion agent based on benzoxazole skeleton and preparation method and application thereof

Abstract

The invention relates to the technical field of photoelectricity, in particular to a light conversion agent based on a benzoxazole skeleton and a preparation method and application of the light conversion agent. The invention provides a light conversion agent based on a benzoxazole skeleton. The light conversion agent comprises an organic compound taking benzoxazole as a parent. According to the light conversion agent based on the benzoxazole skeleton, the problems that an existing light conversion agent is low in ultraviolet light absorption efficiency, and the photoelectric conversion efficiency of a prepared light conversion adhesive film is low are solved.

Description

Technical Field

[0001] The present invention relates to the field of optoelectronic technology, and in particular to a light conversion agent based on a benzoxazole skeleton, and a preparation method and application thereof. Background Art

[0002] As a clean energy source, solar cells have received extensive attention and application in recent years. In particular, due to its high photoelectric conversion efficiency and excellent stability, the penetration rate of solar heterojunction cells (HIT) in the market has gradually increased, and it is expected to replace PERC and TOPCon as the next generation of solar cells. However, HIT cells face aging problems caused by ultraviolet (UV) radiation in practical applications. Ultraviolet rays not only damage the amorphous silicon layer, but also accelerate the degradation of the packaging material, thereby affecting the service life and performance of the battery.

[0003] Light conversion film is a packaging material that can convert ultraviolet light into visible light. It can not only avoid device loss caused by ultraviolet radiation, but also further improve the photoelectric conversion efficiency of the battery. Therefore, the performance of light conversion film has an important impact on the overall performance of solar cells.

[0004] However, the current domestic market size for light-converting adhesive films is very small, mainly because there are many problems with the key ingredient in preparing light-converting adhesive films, the light-converting agent. Existing light-converting agents are divided into inorganic light-converting agents and organic light-converting agents. When inorganic light-converting agents are added to polymer adhesive films, there will be problems such as uneven dispersion and high film haze. Organic light-converting agents are monopolized by a few foreign companies, and domestic organic light-converting agents cannot meet the needs of the high-end market. This situation not only restricts the development of domestic solar cell companies, but also makes related companies subject to others in terms of cost and supply chain.

[0005] Therefore, developing a new, efficient and competitive organic molecular light-converting agent and applying it to light-converting adhesive films is the key to solving the above problems. This will not only help improve the performance of domestic solar cell modules, but also break the foreign technology monopoly and promote independent innovation and healthy development of the domestic photovoltaic industry. Summary of the invention

[0006] In view of this, the purpose of the present invention is to provide a light conversion agent based on a benzoxazole skeleton, which solves the problem that the existing light conversion agent has low absorption efficiency of ultraviolet light and low photoelectric conversion efficiency of the light conversion film prepared.

[0007] In order to achieve the above object, the present invention provides the following technical solutions:

[0008] In a first aspect, the present invention provides a light conversion agent based on a benzoxazole skeleton, wherein the light conversion agent comprises an organic compound based on benzoxazole, and the organic compound has a structure as shown in formula (I) and formula (II):

[0009]

[0010] Preferably,

[0011] In formula (I) and formula (II),

[0012] L 1 and L 2 exists or does not exist, and L 1 and L 2 Same or different;

[0013] Ar 1 to exist or not to exist;

[0014] R 1 ~R 8 Same or different.

[0015] Preferably, in formula (I) and formula (II),

[0016] L 1 and L 2 Each independently is C containing or not containing the first type of heteroatom 3-30 One or more substances in the aromatic compound leave two H atoms to provide a connecting group;

[0017] The first type of heteroatom is selected from one or more of N, O and S;

[0018] L 1 and L 2 There is one or more substituents in the first combination;

[0019] The first group consists of C 1-12 Alkyl, C 1-12 Alkoxy, C 1-12 Alkyl substituted phenyl, C 1-12 The compound is composed of benzyl groups substituted by alkyl groups.

[0020] More preferably, in formula (I) and formula (II),

[0021] L 1 and L 2 A linking group provided by the removal of two H atoms from one or more of the following substances, each independently selected from benzene, diphenyl, terphenyl, naphthalene, anthracene, phenanthrene, dibenzofuran, pyrimidine, triazine, benzothiazole, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, thiophene, furan, benzothiophene, dibenzothiophene, pyrene, perylene, and spirobifluorene;

[0022] L 1 and L 2There is one or more of the following substituents: 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 A substituent combination consisting of an alkyl group substituted with a benzyl group.

[0023] Preferably, in formula (I) and formula (II),

[0024] Ar 1 A linking group provided for the removal of two H atoms from one or more groups in the second combination; or

[0025] Ar 1 Because C 1-30 The connecting group is provided by replacing one or more groups in the second combination with two H atoms by alkyl, alkoxy, alkenyl, phenyl or benzyl;

[0026] The second group consists of C 1-12 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl groups.

[0027] More preferably, in formula (I) and formula (II),

[0028] Ar 1 Because C 1-10 The connecting group provided by replacing at least one of the following groups with two H atoms by alkyl, alkoxy, alkenyl, phenyl or benzyl: 1-10 A combination of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0029] Preferably,

[0030] In formula (I) and formula (II),

[0031] R 1 ~R 8 Each independently selected from a hydrogen atom or a linking group provided by leaving one H atom from one or more groups in the third combination;

[0032] The third group consists of C 1-12 Alkyl, C 1-12 Alkoxy, C 1-12 Alkyl substituted phenyl, C 1-12 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0033] More preferably,

[0034] The third group consists of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0035] Further preferably, in formula (I),

[0036] L 1 and L 2 does not exist;

[0037] Ar 1 Presence or absence; optional presence of Ar 1 A connecting group provided for the removal of two H atoms from one or more groups in combination B or from C 1-10 The connecting group is provided by removing two H atoms from one or more of the alkyl, alkoxy, alkenyl, phenyl, and benzyl groups in combination B; the combination B is composed of C 1-10 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0038] R 1 ~R 8 The same or different, each independently selected from a hydrogen atom or a connecting group provided by leaving one H atom of one or more groups in combination C; the combination C is composed of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0039] More preferably, the compound represented by formula (I) is selected from any one of Compound 1 to Compound 33.

[0040] Further preferably, in formula (I),

[0041] L 1 and L 2 Exist and are the same; L 1 and L 2 A linking group provided by the removal of two H atoms from one or more of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, dibenzofuran, pyrimidine, triazine, benzothiazole, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, thiophene, furan, benzothiophene, dibenzothiophene, pyrene, perylene, and spirobifluorene; L 1and L 2 There is optionally one or more substituents selected from combination A; the combination A consists of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The compound is composed of benzyl groups substituted by alkyl groups.

[0042] Ar 1 Presence or absence; optional presence of Ar 1 A connecting group provided for the removal of two H atoms from one or more groups in combination B or from C 1-10 The connecting group is provided by removing two H atoms from one or more of the alkyl, alkoxy, alkenyl, phenyl, and benzyl groups in combination B; the combination B is composed of C 1-10 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0043] R 1 ~R 8 The same or different, each independently selected from a hydrogen atom or a connecting group provided by leaving one H atom of one or more groups in combination C; the combination C is composed of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0044] More preferably, the compound represented by formula (I) is selected from any one of Compounds 34 to 60.

[0045] Further preferably, in formula (I),

[0046] L 1 and L 2 Exist and different; L 1 and L 2 A linking group provided by the removal of two H atoms from one or more of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, dibenzofuran, pyrimidine, triazine, benzothiazole, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, thiophene, furan, benzothiophene, dibenzothiophene, pyrene, perylene, and spirobifluorene; L 1 and L 2 There is optionally one or more substituents selected from combination A; the combination A consists of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C1-10 The compound is composed of benzyl groups substituted by alkyl groups.

[0047] Ar 1 Presence or absence; optional presence of Ar 1 A connecting group provided for the removal of two H atoms from one or more groups in combination B or from C 1-10 The connecting group is provided by removing two H atoms from one or more of the alkyl, alkoxy, alkenyl, phenyl, and benzyl groups in combination B; the combination B is composed of C 1-10 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0048] R 1 ~R 8 The same or different, each independently selected from a hydrogen atom or a connecting group provided by leaving one H atom of one or more groups in combination C; the combination C is composed of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0049] More preferably, the compound represented by formula (I) is selected from any one of Compound 61 to Compound 72.

[0050] Further preferably, in formula (II),

[0051] L 1 and L 2 does not exist;

[0052] Ar 1 Presence or absence; optional presence of Ar 1 A connecting group provided for the removal of two H atoms from one or more groups in combination B or from C 1-10 The connecting group is provided by removing two H atoms from one or more of the alkyl, alkoxy, alkenyl, phenyl, and benzyl groups in combination B; the combination B is composed of C 1-10 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0053] R 1 ~R 6 The same or different, each independently selected from a hydrogen atom or a connecting group provided by leaving one H atom of one or more groups in combination C; the combination C is composed of C 1-10 Alkyl, C 1-10Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0054] More preferably, the compound represented by formula (II) is selected from any one of Compound 73 to Compound 88.

[0055] Further preferably, in formula (II),

[0056] L 1 and L 2 Exist and are the same; L 1 and L 2 A linking group provided by the removal of two H atoms from one or more of benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, dibenzofuran, pyrimidine, triazine, benzothiazole, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, thiophene, furan, benzothiophene, dibenzothiophene, pyrene, perylene, and spirobifluorene; L 1 and L 2 There is optionally one or more substituents selected from combination A; the combination A consists of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The compound is composed of benzyl groups substituted by alkyl groups.

[0057] Ar 1 Presence or absence; optional presence of Ar 1 A connecting group provided for the removal of two H atoms from one or more groups in combination B or from C 1-10 The connecting group is provided by removing two H atoms from one or more of the alkyl, alkoxy, alkenyl, phenyl, and benzyl groups in combination B; the combination B is composed of C 1-10 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl.

[0058] R 1 ~R 6 The same or different, each independently selected from a hydrogen atom or a connecting group provided by leaving one H atom of one or more groups in combination C; the combination C is composed of C 1-10 Alkyl, C 1-10 Alkoxy, C 1-10 Alkyl substituted phenyl, C 1-10 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

[0059] More preferably, the compound represented by formula (II) is selected from any one of Compound 89 to Compound 106.

[0060] Among them, the structures of Compound 1 to Compound 106 are shown below:

[0061]

[0062]

[0063]

[0064]

[0065] In a second aspect, a method for preparing the light conversion agent of the present invention is provided, comprising the preparation of formula (I), wherein the preparation of formula (I) comprises:

[0066] 1) Preparation of asymmetric benzoxazole-based light conversion agents:

[0067] Step S1.

[0068]

[0069] Step S2.

[0070]

[0071] Step S3.

[0072]

[0073] Step S4.

[0074]

[0075] Among them, R 1 ≠R 5 , R 2 ≠R 6 , R 3 ≠R 7 , R 4 ≠R 8 ;

[0076] 2) Preparation of partially symmetrical benzoxazole-based light conversion agent: Step S1.

[0077]

[0078] Step S2.

[0079]

[0080] Step S3.

[0081]

[0082] Among them, R 1 =R 5 , R 2 =R 6 , R 3 =R 7 , R 4 =R 8 ; L 1 ≠L 2 ;

[0083] 3) Preparation of a completely symmetrical light-converting agent based on a benzoxazole skeleton:

[0084] Step S1.

[0085]

[0086] Step S2.

[0087]

[0088] Among them, R 1 =R 5 , R 2 =R 6 , R 3 =R 7 , R 4 =R 8 ; L 1 =L 2 .

[0089] Preferably, the preparation includes formula (II), wherein the preparation includes: 1) preparation of an asymmetric benzoxazole skeleton-based light conversion agent:

[0090] Step S1.

[0091]

[0092] Step S2.

[0093]

[0094] Step S3.

[0095]

[0096] Among them, R 1 ≠R 4 , R 2 ≠R 5 , R 3 ≠R 6 , L1 ≠L 2 ;

[0097] 2) Preparation of a completely symmetrical light-converting agent based on a benzoxazole skeleton:

[0098] Step S1.

[0099]

[0100] Step S2.

[0101]

[0102] Among them, R 1 =R 4 , R 2 =R 5 , R 3 =R 6 , L 1 =L 2 .

[0103] In a third aspect, a light conversion adhesive film is provided, wherein the light conversion adhesive film comprises the light conversion agent described in the present invention.

[0104] In a fourth aspect, a use of the light conversion agent of the present invention in preparing a light conversion adhesive film is provided.

[0105] A fifth aspect provides application of the light conversion adhesive film described in the present invention in a solar cell module.

[0106] Compared with the prior art, the technical solution provided by the present invention has at least the following beneficial effects or advantages:

[0107] The organic compound provided by the present invention improves the absorption intensity of ultraviolet light by the molecule and the efficiency of converting ultraviolet light into visible light. The benzoxazole structure is used as an acceptor group to absorb energy in the ultraviolet region and efficiently convert it into visible light for radiation, further improving the photoelectric conversion efficiency.

[0108] The raw materials for preparing the organic compound of the present invention are low in price, and the preparation reaction type is a conventional reaction, and large-scale production is possible.

[0109] The light-converting adhesive film formed by adding the benzoxazole skeleton light-converting agent to the adhesive film is applied to a solar cell module, has high light transmittance in the visible light region, has good ultraviolet light absorption performance, and has high efficiency in converting ultraviolet light into visible light. BRIEF DESCRIPTION OF THE DRAWINGS

[0110] In order to more clearly illustrate the technical solution of the present invention, the drawings involved in the description of the embodiments will be briefly introduced below. Obviously, the drawings in the description are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0111] Figure 1 is the H NMR spectrum of compound 13 in Example 1 of the present invention;

[0112] Figure 2 is the H NMR spectrum of compound 43 in Example 2 of the present invention;

[0113] Figure 3 This is the H NMR spectrum of compound 62 of Example 3 of the present invention;

[0114] Figure 4 is the H NMR spectrum of compound 75 of Example 4 of the present invention;

[0115] Figure 5 This is the H NMR spectrum of compound 96 in Example 5 of the present invention. DETAILED DESCRIPTION

[0116] The technical scheme of the present invention is described below in conjunction with the examples, but the present invention is not limited to the following examples. The experimental methods and detection methods described in each example are conventional methods unless otherwise specified; the reagents and materials described are commercially available unless otherwise specified.

[0117] Example 1 Synthesis of Compound 13

[0118]

[0119] Synthesis process of compound 13: 2-aminophenol (1.04 g, 9.50 mmol) and 50 ml of ethanol were added to a three-necked flask, and 4,4'-biphenyldicarboxaldehyde (1 g, 4.75 mmol) and manganese dioxide (1.65 g, 19 mmol) were added after dissolving, and the mixture was reacted at 25°C for 1 h. The manganese dioxide in the system was removed by filtration, and the filtrate was concentrated under reduced pressure, and then recrystallized from toluene and ethanol to obtain a white solid: 1.71 g [purity: 99.3%. Mass spectrum: C 26 H 16 O 2 N 2 , theoretical value: 388.43, measured value: 388.42. 1 HNMR (400 MHz, DMSO-d 6)δ8.09(d,J=1.4Hz,2H),8.06(d,J=1.4Hz,2H),7.65(d,J=1.3Hz,2H),7.63(d,J=1.3Hz,2H),7.61–7.56(m,4H),7.44–7.39(m,4H).].

[0120] Yield: 92.85%.

[0121] Example 2 Synthesis of Compound 43

[0122]

[0123] Synthesis process of intermediate 43-1: 2-aminophenol (1 g, 9.16 mmol) and 50 ml of ethanol were added to a three-necked flask, and 4-bromobenzaldehyde (1.54 g, 8.32 mmol) and manganese dioxide (1.6 g, 18.4 mmol) were added after dissolving, and the mixture was reacted at 25°C for 1 h. The manganese dioxide in the system was removed by filtration, and the filtrate was concentrated under reduced pressure, and then recrystallized from toluene and ethanol to obtain a white solid: 2.18 g [purity: 99%. 1 H NMR (400 MHz, DMSO-d 6 )δ8.03(ddd,J=8.0Hz,1H),7.77(ddd,J=8.5Hz,5H),7.40(ddd,J=8.0Hz,2H)].

[0124] Yield: 95.61%.

[0125] The synthesis process of compound 43: 24 ml of toluene, 5 ml of ethanol, intermediate 43-1 (2.18 g, 7.95 mmol), 9,9-dimethyl-2,7-fluorene diboronic acid (1.13 g, 4.0 mmol) were added to a three-necked flask, heated to 40°C to remove oxygen for 0.5 h, then palladium acetate (0.018 g, 0.08 mmol) was added, and the temperature was continued to rise to reflux for 5 h. After the reaction solution was passed through a column to remove the catalyst, it was concentrated under reduced pressure, and recrystallized from toluene and ethanol to obtain 1.8 g of off-white solid compound 43 [purity: 99.5%. Mass spectrum: C 41 H 28 O 2 N 2 , theoretical value: 580.69, measured value: 580.62. 1 H NMR (400 MHz, DMSO-d 6)δ8.09(d,J=1.3Hz,4H),8.06(d,J=1.4Hz,2H),7.81(d,J=7.7Hz,4H),7.70–7.65(m,3H),7.64(d,J =2.7Hz,1H),7.62(d,J=2.2Hz,4H),7.59(dd,J=9.7,2.4Hz,4H),7.45–7.37(m,5H),1.58(s,6H).].

[0126] Yield: 77.9%.

[0127] Example 3 Synthesis of Compound 62

[0128]

[0129] The synthesis process of intermediate 62-1 is the same as the synthesis of intermediate 43-1 in Example 2;

[0130] Synthesis process of intermediate 62-2: Add 2-aminophenol (1 g, 9.16 mmol) and 50 ml of ethanol to a three-necked flask, add 6-bromo-2-naphthaldehyde (1.95 g, 8.32 mmol) and manganese dioxide (1.6 g, 18.4 mmol) after dissolving, and react at 25°C for 1 hour. Filter to remove manganese dioxide in the system, concentrate the filtrate under reduced pressure, and recrystallize from toluene and ethanol to obtain a white solid: 2.50 g [purity: 99.2%. 1 H NMR (400 MHz, DMSO-d 6 )δ7.24-7.42(2H,7.31(ddd,J=8.6,1.9,0.5Hz),7.36(ddt,J=8.6,2.0,0.5Hz)),7.55-7.75(2 H,7.63(ddd,J=8.1,7.4,1.8Hz),7.68(ddd,J=8.8,8.1,1.8Hz)),7.82-7.97(3H,7.88(ddd,J=8 .8,1.8,0.5Hz),7.91(ddd,J=8.7,1.6,0.4Hz),7.92(tq,J=1.9,0.4Hz)),8.07-8.22(2H,8.13 (ddt,J=8.7,1.9,0.5Hz),8.15(ddd,J=7.4,1.8,0.5Hz)),8.55(1H,ddq,J=2.0,1.6,0.5Hz).].

[0131] Yield: 93%.

[0132] The synthesis process of compound 62: 24 ml of toluene, 5 ml of ethanol, intermediate 62-1 (1 g, 3.65 mmol), intermediate 62-2 (1.18 g, 3.65 mmol), 1,4-phenylenediboronic acid (0.60 g, 3.65 mmol) were added to a three-necked flask, heated to 40 ° C to remove oxygen for 0.5 h, then palladium acetate (0.009 g, 0.04 mmol) was added, and the temperature was continued to rise to reflux for 5 h. After the reaction solution was passed through a column to remove the catalyst, it was concentrated under reduced pressure, and recrystallized from toluene and ethanol to obtain compound 62 as an off-white solid of 1.4 g [purity: 99.2%. Mass spectrum: C 36 H 22 O 2 N 2 , theoretical value: 514.58, measured value: 514.56. 1 HNMR (400 MHz, DMSO-d 6 )δ8.58(t,1H),8.11–8.02(m,4H),7.99(dd,J=2.1Hz,2H),7.87–7.82(m,3H),7.80(dd,J=7.9,2.2 Hz,1H),7.64(dt,J=9.3,1.4Hz,4H),7.62–7.57(m,4H),7.41(dddd,J=6.2,3.3,2.3,0.9Hz,4H).].

[0133] Yield: 75.2%.

[0134] Example 4 Synthesis of Compound 75

[0135]

[0136] The synthesis process of compound 75: 15 ml of toluene, 4 ml of ethanol, 5-bromobenzoxazole (2.40 g, 12.1 mmol), and 1,4-phenylenediboronic acid (1.0 g, 6.03 mmol) were added to a three-necked flask, heated to 40°C to remove oxygen for 0.5 h, then palladium acetate (0.013 g, 0.06 mmol) was added, and the temperature was continued to rise to reflux for 5 h. After the reaction solution was passed through a column to remove the catalyst, it was concentrated under reduced pressure, and recrystallized from toluene and ethanol to obtain 1.44 g of off-white solid compound 75 [purity: 99.6%. Mass spectrum: C 20 H 12 O 2 N 2 , theoretical value: 312.33, measured value: 312.30. 1 H NMR (400 MHz, DMSO-d 6)δ8.48(s,2H),8.06(d,J=2.1Hz,2H),7.85(s,4H),7.71(dd,J=8.1,2.1Hz,2H),7.65–7.58(m,2H).].

[0137] Yield: 76.81%.

[0138] Example 5 Synthesis of Compound 96

[0139] Step S1: Synthesis of Intermediate 96-1

[0140]

[0141] Synthesis process of intermediate 96-1: Add 4-amino-4 ， -Br[1,1 ， -biphenyl]-3-ol (1 g, 3.79 mmol) and 100 ml of ethanol were dissolved, and benzaldehyde (0.44 g, 4.17 mmol) and manganese dioxide (0.66 g, 7.58 mmol) were added and reacted at 25°C for 1 h. The manganese dioxide in the system was removed by filtration, and the filtrate was concentrated under reduced pressure and recrystallized to obtain a white solid: 1.19 g [purity: 99.2%. 1 HNMR (400 MHz, DMSO-d 6 )δ8.19(dd,J=7.1Hz,2H),7.93(dd,J=7.1Hz,3H),7.60(tdd,J=7.7Hz,3H),7.43(ddd,J=8.7Hz,2H),7.23(ddd,J=8.7Hz,2H)】.

[0142] Yield: 90%.

[0143] Step S2: Synthesis of Compound 96

[0144]

[0145] The synthesis process of compound 96: 24 ml of toluene, 5 ml of ethanol, intermediate 96-1 (1.19 g, 3.40 mmol), 9,9-dimethyl-2,7-fluorene diboronic acid (1.48 g, 1.70 mmol) were added to a three-necked flask, heated to 40°C to remove oxygen for 0.5 h, then palladium acetate (0.009 g, 0.04 mmol) was added, and the temperature was continued to rise to reflux for 5 h. After the reaction solution was passed through a column to remove the catalyst, it was concentrated under reduced pressure, and recrystallized from toluene and ethanol to obtain 1.8 g of compound 96 as an off-white solid [purity: 99.5%. Mass spectrum: C 53 H 36 O 2 N 2, theoretical value: 732.88, measured value: 732.85. 1 H-NMR (400 MHz, DMSO-d 6 )(ppm)δ8.14(dd,J=9.5,2.0Hz,4H),8.06(d,J=2.1Hz,1H),7.85(s,8H),7.82(s,1H),7.81–7.78(m,3H),7.75(d,J= 2.1Hz,1H),7.72–7.68(m,2H),7.67(d,J=2.1Hz,2H),7.63(dd,J=7.7,2.2Hz,2H),7.59–7.48(m,6H),1.58(s,6H).].

[0146] Yield: 75%.

[0147] The PLQY results of each compound are shown in Table 1.

[0148] Table 1 UV-visible light conversion efficiency (PLQY)

[0149] Compound Compound 13 Compound 43 Compound 62 Compound 75 Compound 96 PLQY / % 97.6％ 98％ 98.1％ 97.8％ 98.5％

[0150] As can be seen from Table 1, each compound prepared in the embodiment of the present invention has a relatively good ultraviolet-visible light conversion efficiency. Specifically, each compound provided in the embodiment of the present invention improves the absorption intensity of the molecule to ultraviolet light and the efficiency of converting ultraviolet light into visible light; through the benzoxazole structure as an acceptor group, the energy in the ultraviolet region is absorbed and efficiently converted into visible light for radiation, further improving the photoelectric conversion efficiency.

[0151] It should be understood that the disclosed invention is not limited only to the specific method, scheme and material of description, because these all can change.It should also be understood that the terminology used herein is only for the purpose of describing specific embodiment scheme, rather than being intended to limit the scope of the present invention, and the scope of the present invention is only limited to the appended claims.

[0152] Those skilled in the art will also recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments of the invention described herein. Such equivalents are also intended to be encompassed by the appended claims.

Claims

1. A light conversion agent based on a benzoxazole skeleton, characterized in that: The light conversion agent comprises an organic compound based on benzoxazole, and the organic compound has a structure as shown in formula (I) and formula (II):

2. The light conversion agent according to claim 1, characterized in that In formula (I) and formula (II), L1 and L2 are present or absent, and L1 and L2 are the same or different; Ar1 is present or absent; R1 to R8 are the same or different.

3. The light conversion agent according to claim 2, characterized in that: In formula (I) and formula (II), L1 and L2 are each independently C containing or not containing the first type heteroatom 3-30 One or more substances in the aromatic compound leave two H atoms to provide a connecting group; The first type of heteroatom is selected from one or more of N, O and S; One or more substituents in the first combination exist on L1 and L2; The first group consists of C 1-12 Alkyl, C 1-12 Alkoxy, C 1-12 Alkyl substituted phenyl, C 1-12 The compound is composed of benzyl groups substituted by alkyl groups.

4. The light conversion agent according to claim 3, characterized in that: In formula (I) and formula (II), Ar1 is a connecting group provided by leaving two H atoms from one or more groups in the second combination; or Ar1 is composed of C 1-30 A connecting group provided by replacing one or more groups in the second combination with two H atoms by alkyl, alkoxy, alkenyl, phenyl, or benzyl; The second group consists of C 1-12 It is composed of alkyl, alkenyl, alkynyl, phenyl, biphenyl, benzyl, naphthyl, anthracenyl, fluorenyl and carbazolyl groups.

5. The light conversion agent according to claim 4, characterized in that: In formula (I) and formula (II), R1 to R8 are each independently selected from a hydrogen atom or a linking group provided by leaving one H atom from one or more groups in the third combination; The third group consists of C 1-12 Alkyl, C 1-12 Alkoxy, C 1-12 Alkyl substituted phenyl, C 1-12 The alkyl-substituted benzyl, phenyl, benzyl, tolyl, biphenyl, naphthyl, benzotriazolyl, benzoxazolyl, benzothiazolyl, dibenzothiazolyl and triazinyl groups are composed.

6. The method for preparing the light conversion agent according to any one of claims 1 to 5, characterized in that: The preparation of formula (I) comprises: 1) Preparation of asymmetric benzoxazole-based light conversion agents: Step S1. Step S2. Step S3. Step S4. Among them, R1≠R5, R2≠R6, R3≠R7, R4≠R8; 2) Preparation of partially symmetrical light conversion agents based on benzoxazole skeletons: Step S1. Step S2. Step S3. Wherein, R1=R5, R2=R6, R3=R7, R4=R8; L1≠L2; 3) Preparation of a completely symmetrical light conversion agent based on a benzoxazole skeleton: Step S1. Step S2. Among them, R1=R5, R2=R6, R3=R7, R4=R8; L1=L2.

7. The preparation method according to claim 6, characterized in that: Also included is the preparation of formula (II), wherein the preparation of formula (II) comprises: 1) Preparation of asymmetric benzoxazole-based light conversion agents: Step S1. Step S2. Step S3. Among them, R1≠R4, R2≠R5, R3≠R6, L1≠L2; 2) Preparation of a completely symmetrical light-converting agent based on a benzoxazole skeleton: Step S1. Step S2. Among them, R1=R4, R2=R5, R3=R6, and L1=L2.

8. A light-converting adhesive film, characterized in that: The light conversion adhesive film comprises the light conversion agent according to any one of claims 1-5.

9. Use of the light conversion agent according to any one of claims 1 to 5 in the preparation of light conversion adhesive film.

10. Use of the light conversion adhesive film according to claim 8 in a solar cell module.

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