A benzofluorene photochromic compound and its application

Abstract

The invention discloses a benzofluorene photochromic compound, the general structural formula of which is shown below: The benzofluorene photochromic compound of the invention has a higher optical density difference, a faster fading decay rate and excellent light resistance, and has excellent development and application prospects.

Description

Technical Field

[0001] The invention belongs to the field of photochromic materials, and in particular relates to a benzofluorene photochromic compound and application thereof. Background Art

[0002] The phenomenon of changing color in response to specific light is called photochromism, and the material that causes this photochromism is called photochromic material (Photochromic, photoreversible color-changing compound or photochromic compound). Photochromic compounds are roughly divided into pigment form and dye form or inorganic form and organic form. When a photochromic compound in the form of a solution or dispersion is exposed to sunlight or ultraviolet rays, it changes from colorless to a specific color, and when placed in the dark or without strong ultraviolet radiation, it returns to its original color. At present, the most widely used commercial applications are photochromic glasses, high-end cosmetics, color-changing clothing and color-changing 3C products, etc. Potential application areas include intelligent window film coatings, organic optoelectronic information storage units and color-changing anti-counterfeiting inks, etc.

[0003] Naphthopyrans are widely used in the commercial industry. Under light or UV irradiation, naphthopyrans can produce neutral gray and tea tones, which are particularly suitable for use in the photochromic glasses industry. Especially in strong light or in midsummer, photochromic glasses can easily adjust the light transmittance, and have a wide range of applications. However, traditional naphthopyran photochromic materials do not have a deep color and fade slowly, and cannot achieve rapid decolorization, making it difficult to meet expectations for photochromic products.

[0004] Patent application with publication number CN107253943A discloses a photochromic compound, such as but not limited to a thermally reversible photochromic compound, which can exhibit useful photochromic properties in at least one state and can be used in various applications to impart photochromic properties. Summary of the invention

[0005] The purpose of the present invention is to provide a benzofluorene photochromic compound, which also has a pyranochromic structure. By changing the position of functional groups, extending the conjugated structure and introducing electron-donating groups, the compound has a higher optical density difference, a faster fading decay rate and excellent light resistance, and has excellent development and application prospects.

[0006] Another object of the present invention is to provide a use of the benzofluorene photochromic compound in the preparation of photochromic products.

[0007] In order to achieve the above object, the technical solution adopted by the present invention is as follows:

[0008] The first aspect of the present invention provides a benzofluorene photochromic compound, the general structural formula of which is shown below:

[0009]

[0010] in,

[0011] R 1 Selected from hydrogen, C1-C5 alkoxy;

[0012] R 2 Selected from hydrogen, C1-C5 alkyl;

[0013] R 3 Selected from hydrogen, C1-C5 alkyl;

[0014] R 4 Selected from hydrogen, C1-C5 alkoxy, C1-C5 alkyl;

[0015] R 5 Selected from hydrogen, C1-C5 alkoxy, C1-C5 alkyl;

[0016] R 6 Selected from hydrogen, C1-C5 alkoxy, C1-C5 alkyl, -N(CH 3 ) 2 、-N(CH 2 CH 3 ) 2 ; R 7 Selected from hydrogen, C1-C5 alkoxy, C1-C5 alkyl, -N(CH 3 ) 2 、-N(CH 2 CH 3 ) 2 or, R 4 , R 5 Together with carbon it forms a six-membered ring (e.g. benzene, cyclohexane).

[0017] Preferably, in the benzofluorene photochromic compound,

[0018] R 1 is selected from hydrogen, methoxy, ethoxy, isopropoxy;

[0019] R 2 is selected from hydrogen, methyl, ethyl, isopropyl;

[0020] R 3 is selected from hydrogen, methyl, ethyl, isopropyl;

[0021] R 4 is selected from hydrogen, methoxy, ethoxy, methyl;

[0022] R 5 is selected from hydrogen, methoxy, ethoxy, methyl;

[0023] R 6Selected from hydrogen, methoxy, ethoxy, methyl, -N(CH 3 ) 2 、-N(CH 2 CH 3 ) 2 ;

[0024] R 7 Selected from hydrogen, methoxy, ethoxy, methyl, -N(CH 3 ) 2 、-N(CH 2 CH 3 ) 2 ;

[0025] or, R 4 , R 5 Together with carbon it forms a benzene ring.

[0026] Most preferably, the structure of the benzofluorene photochromic compound is selected from one of the following structures:

[0027]

[0028] The second aspect of the present invention provides a use of the benzofluorene photochromic compound in the preparation of a photochromic product.

[0029] The photochromic product is selected from eyeglass lenses (cast photochromic substrate lenses), optical lens products (magnifying lenses, camera lenses, dimming lenses, etc.), glass products (glass interlayer films, color-changing window glass, color-changing automotive film products, etc.), and electronic consumer products (display screens, display back panels, security elements, anti-counterfeiting originals, decorative products, clothing, accessories, etc.).

[0030] The added mass of the benzofluorene photochromic compound in the eyeglass lens is 0.5-2%.

[0031] The added mass of the benzofluorene photochromic compound of the glass interlayer film is 0.05-0.8%.

[0032] The third aspect of the present invention provides a use of the benzofluorene photochromic compound in the preparation of a photochromic material.

[0033] Due to the adoption of the above technical solution, the present invention has the following advantages and beneficial effects:

[0034] The benzofluorene photochromic compound of the present invention has a high optical density difference and a fast fading decay rate, and can achieve deep color change in areas with strong light, which can provide better protection and aesthetic effects. In addition, the excellent light resistance and stability performance make this type of material not only applicable to commercial photochromic glasses, but also to textile printing and dyeing, green energy-saving glass, photochromic coatings and plastics, etc., with a wide range of applications. DETAILED DESCRIPTION

[0035] In order to explain the present invention more clearly, the present invention is further described below in conjunction with preferred embodiments. It should be understood by those skilled in the art that the following specific description is illustrative rather than restrictive, and should not be used to limit the scope of protection of the present invention.

[0036] Example 1

[0037]

[0038] In a 500mL two-necked flask, add phenylacetic acid (13.6g, 0.10mol) and 250mL toluene solvent, stir for 30min, then add phosphorus oxychloride (25.0mL, 0.27mol). Stir and react at 80°C for 5 hours, cool to room temperature, and concentrate by rotary evaporation to obtain phenylacetyl chloride, which is directly used for the next step without purification.

[0039] Phenylacetyl chloride was directly added to a 500 mL two-necked Schlenk flask, 6-methoxy-1,1-dimethyl-1,3-dihydro-2H-inden-2-one (22.8 g, 0.12 mol) and dry THF (200 mL) were added to the flask, and the Schlenk flask was placed in a low temperature bath (-78 ° C) under nitrogen atmosphere with stirring, and 190 mL of 1.6 mol / L n-butyl lithium was injected. After the injection was complete, the reaction solution was slowly heated to 40 ° C. The reaction was stirred at room temperature for 4 hours, the reaction solution was poured into ice water, 100 mL of dilute hydrochloric acid was added and stirred, and the mixture was extracted with ethyl acetate (3×200 mL). The organic phases were combined and the solvent was dried by spin drying, and the mixture was separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1), and 17.0 g of yellow solid 1-(2-hydroxy-6-methoxy-1,1-dimethyl-1H-inden-3-yl)-2-phenyl-1-one was obtained, with a yield of 55%. MS (ESI, m / z): [M+H] + calcd for(C 20 H 20 O 3 ),309.1;found,309.1.

[0040]

[0041] 1-(2-Hydroxy-6-methoxy-1,1-dimethyl-1H-inden-3-yl)-2-phenyl-1-one (15.0 g, 0.049 mol) was dissolved in 250 mL of toluene solvent and added to a 500 mL three-necked flask with a water separator. 5.0 g of 85% polyphosphoric acid and 5.0 g of pyridinium p-toluenesulfonate were added to the flask. The mixture was stirred under reflux at 110°C for 8 hours. The reaction solution was poured into ice water and extracted with toluene (3×200 mL). The organic phases were combined and the solvent was dried by spin drying. The organic phases were separated by column chromatography (200-300 mesh silica gel, eluted with pure dichloromethane) to obtain 4.7 g of brown solid 9-methoxy-11,11-dimethyl-11H-benzofluorene-6-ol. The yield was 33%. MS (ESI, m / z): [M+H] + calcd for(C 20 H 18 O 2 ),291.1;found,291.1.

[0042]

[0043] In a 500mL two-necked flask, 4,4'-dimethoxybenzophenone (10.0g, 0.041mol) was dissolved in 100mL ethylenediamine, and acetylene lithium ethylenediamine complex (6.3g, 0.062mol) was added. The reaction was stirred at room temperature for 4 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200mL), the organic phase was combined and the solvent was dried, and column chromatography was performed (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1) to obtain 8.6g of light yellow solid 1,1-bis(4-methoxyphenyl)prop-2-ynyl-1-ol, with a yield of 78%. MS (ESI, m / z): [M+H] + calcd for(C 17 H 16 O 3 ),269.1;found,269.1.

[0044]

[0045] In a 250 mL three-necked flask, 1,1-bis(4-methoxyphenyl)prop-2-ynyl-1-ol (1.27 g, 4.7 mmol) and 9-methoxy-11,11-dimethyl-11H-benzofluorene-6-ol (1.1 g, 3.8 mmol) were dissolved in 100 mL of toluene, and 0.7 g of dodecylbenzenesulfonic acid was added. The mixture was heated to 90°C and stirred for 6 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200 mL), the organic phases were combined and the solvent was dried, and separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and dichloromethane in a volume ratio of 1:1), to obtain 760 mg of 11-methoxy-2,2-bis(4-methoxyphenyl)-9,9-dimethyl-2,9-dihydrobenzo[f]indeno[2,1-h]chromene, i.e., compound I-1, with a yield of 37%. The purity was 99.5% as tested by HPLC, and MS (ESI, m / z): [M+H] + calcd for(C 37 H 32 O 4 ),541.2;found,541.2. 1 H NMR (400 MHz, CDCl 3 )δ8.23(d,1H),7.66–7.55(m,4H),7.43-7.32(m,2H),7.27–7.22(m,5H),6.89(d,4H),6.28(d,1H),3.81(s,6H),3.70(s,3H),2.10(s,6H).

[0046] Example 2

[0047]

[0048] In a 500mL two-necked flask, add the compound 2-methoxyphenylacetic acid (16.6g, 0.10mol) and 250mL of toluene solvent, stir for 30min, then add phosphorus oxychloride (25.0mL, 0.27mol). Stir and react at 100°C for 8 hours, cool to room temperature, and concentrate by rotary evaporation to obtain 2-methoxyphenylacetyl chloride, which is directly used for the next step without purification.

[0049] 2-Methoxyphenylacetyl chloride was directly added to a 500 mL two-necked Schlenk flask, 1,3-dihydro-2H-inden-2-one (15.9 g, 0.12 mol) and dry THF (200 mL) were added to the flask, and the Schlenk flask was placed in a low temperature bath (-78°C) and stirred under a nitrogen atmosphere. 190 mL of 1.6 mol / L n-butyl lithium was injected. After the injection was complete, the reaction solution was slowly heated to room temperature and stirred for 2 hours. The reaction solution was poured into ice water, 100 mL of dilute hydrochloric acid was added and stirred, and extracted with ethyl acetate (3×200 mL). The organic phases were combined and the solvent was dried by spin drying, and separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1) to obtain 17.1 g of light yellow solid 1-(2-hydroxy-1H-inden-3-yl)-2-methoxyphenyl-1-ethanone, with a yield of 61%. MS (ESI, m / z): [M+H] + calcd for(C 18 H 16 O 3 ),281.1;found,281.1.

[0050]

[0051] 1-(2-Hydroxy-1H-inden-3-yl)-2-methoxyphenyl-1-ethanone (10.0 g, 0.036 mol) was dissolved in 250 mL of toluene solvent and added to a 500 mL three-necked flask with a water separator. 4.0 g of 85% polyphosphoric acid and 4.0 g of pyridinium p-toluenesulfonate were added to the flask. The mixture was stirred under reflux at 110°C for 8 hours. The reaction solution was poured into ice water and extracted with toluene (3×200 mL). The organic phases were combined and the solvent was dried by spin drying. The mixture was separated by column chromatography (200-300 mesh silica gel, eluted with pure dichloromethane) to obtain 4.1 g of solid 4-methoxy-11H-benzofluorene-6-ol. The yield was 43%. MS (ESI, m / z): [M+H] + calcd for(C 20 H 18 O 2 ),263.1;found,263.1.

[0052]

[0053] In a 250mL three-necked flask, 1,1-bis(4-methoxyphenyl)prop-2-ynyl-1-ol (1.92g, 7.1mmol) and 4-methoxy-11H-benzofluorene-6-ol (1.5g, 5.7mmol) were dissolved in 100mL toluene, and 1.0g dodecylbenzenesulfonic acid was added. Under a nitrogen atmosphere, the mixture was heated to 90°C and stirred for 6 hours. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200mL), the organic phases were combined and the solvent was dried by spin column chromatography (200-300 mesh silica gel, eluted with petroleum ether and dichloromethane in a volume ratio of 1:1), and 1.43g of 5-methoxy-2,2-bis(4-methoxyphenyl)-2,9-dihydrobenzo[f]indeno[2,1-h]chromene, i.e., compound I-2, was obtained, with a yield of 49%. Purity tested by HPLC: 99.5%, MS (ESI, m / z): [M+H] + calcd for(C 37 H 32 O 4 ),513.2;found,513.2. 1 H NMR (400 MHz, CDCl 3 )δ8.24(d,1H),7.74–7.55(m,4H),7.38-7.32(m,2H),7.28–7.22(m,5H),6.89(d,4H),6.58(d,1H),4.24(s,2H),3.81(s,6H),3.79(s,3H).

[0054] Example 3

[0055]

[0056] The phenylacetic acid in Example 1 was replaced with 2,3-dimethoxyphenylacetic acid to obtain solid 3,4,9-trimethoxy-11,11-dimethyl-11H-benzofluorene-6-ol. MS (ESI, m / z): [M+H] + calcd for(C 22 H 22 O 4 ),351.2;found,351.2.

[0057]

[0058] In a 500mL two-necked flask, 4,4'-diethylaminobenzophenone (10.0g, 0.029mol) was dissolved in 100mL ethylenediamine, and acetylene lithium ethylenediamine complex (4.4g, 0.062mol) was added. The reaction was stirred at room temperature for 4 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200mL), the organic phase was combined and the solvent was dried, and column chromatography was performed (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1) to obtain 7.6g of light yellow solid 1,1-bis(4-diethylaminophenyl)prop-2-ynyl-1-ol, with a yield of 75%. MS (ESI, m / z): [M+H] + calcd for(C 23 H 30 N 2 O),351.2;found,351.2.

[0059]

[0060] In a 250 mL three-necked flask, 1,1-bis(4-diethylaminophenyl)prop-2-ynyl-1-ol (2.46 g, 7.0 mmol) and 3,4,9-trimethoxy-11,11-dimethyl-11H-benzofluorene-6-ol (1.5 g, 4.3 mmol) were dissolved in 100 mL of toluene, and 0.8 g of dodecylbenzenesulfonic acid was added. The mixture was heated to 85°C and stirred for 12 hours under a nitrogen atmosphere. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200 mL), the organic phases were combined and the solvent was dried, and separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and dichloromethane in a volume ratio of 1:1), to obtain 890 mg of 5,6,11-trimethoxy-2,2-bis(4-diethylaminophenyl)-9,9-dimethyl-2,9-dihydrobenzo[f]indeno[2,1-h]chromene, i.e., compound I-3, with a yield of 30%. The purity was 99.5% as tested by HPLC, and MS (ESI, m / z): [M+H] + calcd for(C 45 H 50 N 2 O 4 ),683.4;found,683.4. 1 HNMR (400MHz, CDCl 3 )δ8.24(d,1H),7.61–7.48(m,3H),7.38-7.32(m,4H),7.26–7.18(m,5H),6.7 9(d,1H),6.40(d,1H),3.81(s,9H),3.40(q,8H),2.10(s,6H),1.24(t,12H).

[0061] Example 4

[0062]

[0063] In a 500mL two-necked flask, add the compound naphthylacetic acid (18.6g, 0.10mol) and the solvent toluene 250mL, stir for 30min, then add phosphorus oxychloride (25.0mL, 0.27mol). Stir and react at 100℃ for 8 hours, cool to room temperature, and concentrate by rotary evaporation to obtain naphthylacetyl chloride, which can be directly used for the next step without purification.

[0064] Naphthylacetyl chloride was directly added to a 500 mL two-necked Schlenk flask, 5-methoxy-1,3-dihydro-2H-inden-2-one (19.5 g, 0.12 mol) and dry THF (200 mL) were added to the flask, and the Schlenk flask was placed in a low temperature bath (-78°C) and stirred under a nitrogen atmosphere, and 190 mL of 1.6 mol / L n-butyl lithium was injected. After the injection was complete, the reaction solution was slowly heated to room temperature and stirred for 2 hours. The reaction solution was poured into ice water, 100 mL of dilute hydrochloric acid was added and stirred, and extracted with ethyl acetate (3×200 mL). The organic phases were combined and the solvent was dried by spin drying, and separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1) to obtain 17.2 g of solid 1-(2-hydroxy-6-methoxy-1H-inden-3-yl)-2-naphthyl-1-ethanone, with a yield of 52%. MS (ESI, m / z): [M+H] + calcd for(C 22 H 18 O 3 ),331.1;found,331.1.

[0065]

[0066] 1-(2-Hydroxy-6-methoxy-1H-inden-3-yl)-2-naphthyl-1-ethanone (15.0 g, 0.045 mol) was dissolved in 250 mL of toluene solvent and added to a 500 mL three-necked flask with a water separator. 5.0 g of 85% polyphosphoric acid and 5.0 g of pyridinium p-toluenesulfonate were added to the flask. The mixture was stirred under reflux at 110°C for 8 hours. The reaction solution was poured into ice water and extracted with toluene (3×200 mL). The organic phases were combined and the solvent was dried by spin drying. The mixture was separated by column chromatography (200-300 mesh silica gel, eluted with pure dichloromethane) to obtain 3.65 g of solid 11-methoxy-13H-indenadiene [2,1-a] phenanthren-8-ol. The yield was 26%. MS (ESI, m / z): [M+H] + calcd for(C 22 H16 O 2 ),313.1;found,313.1.

[0067]

[0068] In a 500mL two-necked flask, dissolve benzophenone (10.0g, 0.055mol) in 100mL ethylenediamine, and add acetylene lithium ethylenediamine complex (8.4g, 0.082mol). Stir the reaction at room temperature for 4 hours under nitrogen atmosphere. After the reaction, pour the reaction solution into ice water, extract with toluene (3×200mL), combine the organic phases, spin-dry the solvent, and separate by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and ethyl acetate in a volume ratio of 4:1) to obtain 9.4g of light yellow solid 1,1-diphenylprop-2-ynyl-1-ol, yield: 82%. MS (ESI, m / z): [M+H] + calcd for(C 15 H 12 O), 209.1; found, 209.0.

[0069]

[0070] In a 250mL three-necked flask, 1,1-diphenylprop-2-ynyl-1-ol (1.3g, 6.3mmol) and 11-methoxy-13H-indenadiene [2,1-a] phenanthrene-8-ol (1.3g, 4.2mmol) were dissolved in 100mL toluene, and 0.6g dodecylbenzenesulfonic acid was added. Under a nitrogen atmosphere, the mixture was heated to 65°C and stirred for 12 hours. After the reaction, the reaction solution was poured into ice water, extracted with toluene (3×200mL), the organic phases were combined and the solvent was dried by spin drying, and separated by column chromatography (200-300 mesh silica gel, eluted with petroleum ether and dichloromethane in a volume ratio of 1:1), and 950mg 13-methoxy 9,9-diphenyl-9,15-dihydroinden [2,1-h] naphtho [1,2-f] chromene, i.e., compound I-4, was obtained, with a yield of 45%. Purity tested by HPLC: 99.5%, MS (ESI, m / z): [M+H] + calcdfor(C 37 H 26 O 2 ),503.2;found,503.2. 1 H NMR (400 MHz, CDCl 3)δ8.24(d,1H),8.06-7.90(m,3H),7.63–7.45(m,3H),7.38-7.28(m,11H),7.18(d,1H),6.79(d,1H),6.40(d,1H),4.12(s,2H),3.70(s,3H).

[0071] Example 5

[0072] A photochromic compound prepared based on Examples 1 to 4 and a control group is used as a core material for making a cast photochromic substrate lens (eyeglass lens), which is made of the components in parts by weight in Table 1, wherein the photochromic dye used in the control group is 3,3-bis(4-methoxyphenyl)-6,11,13,13-tetramethyl-3,13-dihydrobenzo[h]indeno[2,1-f]chromene.

[0073] Table 1

[0074]

[0075]

[0076] The method for preparing the cast type photochromic substrate lens comprises the following steps:

[0077] In the first step, methyl styrene, hydroxyethyl methacrylate, ethoxylated bisphenol A diacrylate, polyethylene terephthalate, butylated hydroxytoluene, 2-hydroxy-4-methoxybenzophenone, SpeedBlock 770 (bis(2,2,6,6-methyl-4-piperidyl) sebacate, light stabilizer, resin monomers were purchased from Arkema (Shanghai) Chemical Co., Ltd.) and the photochromic compound prepared in Example 1 were mixed evenly, added to a conical flask and stirred for 1 hour, azobisisobutyronitrile was added, and vacuumed at room temperature for 30 minutes, and the mixture was stirred and mixed evenly during the process. Then the temperature was controlled at 40°C, the stirring rate was 300r / min, and the mixture was allowed to stand and vacuumed for 30 minutes.

[0078] In the second step, the mixture prepared in the first step is filtered through a 1.0 μm filter, injected into a glass mold (Jiangsu Asia Pacific Optical Co., Ltd., lens mold, luminosity -2.50, A mold A250) and sealed, and heated from room temperature to 95°C in a curing furnace over 20 hours. The programmed temperature rise curve is: ①0-5h maintain 34°C; ②5-12h uniformly increase to 50°C; ③12-18h uniformly increase to 95°C; ④18-20h maintain 95°C; complete one-step curing to obtain the lens.

[0079] In the third step, the lens obtained in the second step is subjected to mold opening, edge trimming and cleaning processes, and is subjected to secondary curing molding at a constant temperature of 110° C. for 1.5 hours in a precision curing furnace to obtain the cast photochromic substrate lens A.

[0080] The fourth step is to detect the photochromic response value and discoloration half-life (t 1 / 2 ), the test methods and calculation results are based on the corresponding clauses in the national standard GB 10810.3-2006.

[0081] The photochromic compounds prepared in Examples 2 to 4 and the control group were respectively prepared using the above method to obtain lenses B, C, D and E, and compared. The data are shown in Table 2.

[0082] Table 2

[0083]

[0084]

[0085] As can be seen from the data in Table 2, by comparing AD and the control group E, it can be found that AD has a significantly higher photochromic response value, which means that a deeper color change effect can be achieved. In areas with strong light, deep color change can be achieved, which can provide better protection and aesthetic effects. Comparing the discoloration half-life of AD and E, AD has a shorter discoloration half-life, which means that the recovery speed is faster and it can adapt to the environment faster during the rapid conversion between indoors and outdoors. Therefore, AD has the potential to be further developed into high-end commercial photochromic lenses.

[0086] Example 6

[0087] A photochromic compound prepared based on Examples 1 to 4 and a control group is used as a core material for preparing a glass interlayer film. The compound is made of the components in parts by weight in Table 3, wherein the photochromic dye used in the control group is 3,3-bis(4-methoxyphenyl)-6,11,13,13-tetramethyl-3,13-dihydrobenzo[h]indeno[2,1-f]chromene.

[0088] Table 3

[0089] Element Weight Polyvinyl butyral resin 9 servings Dibutyl phthalate 4 servings Ethyl acetate 86 copies SpeedBlock770 0.8 parts Photochromic compounds 0.2 parts

[0090] The method for preparing the glass interlayer film comprises the following steps:

[0091] In the first step, polyvinyl butyral resin, dibutyl phthalate, ethyl acetate, SpeedBlock770 and the photochromic compound are mechanically stirred for 2 hours, mixed evenly, and allowed to stand for 1 hour.

[0092] In the second step, the mixture obtained in the first step is fed into a single screw extruder (type SJ15), uniformly heated to 140°C to become a molten state, and extruded to obtain a glass interlayer film (0.38mm×0.5m). An appropriate amount of the obtained film is cut and placed between two pieces of glass (5mm×50mm×50mm), and the temperature is maintained at 90°C to form laminated glass F.

[0093] The radiation resistance test results and exposure test results of the obtained laminated glass F were detected, and the radiation resistance and exposure test were carried out using the method specified in the national standard GB / T5137.3-2020. The photochromic compounds prepared in Examples 2 to 4 and the control group were respectively prepared by the above method to obtain laminated glasses G, H, I, and J, and the tests were compared. The data are shown in Table 4.

[0094] Table 4

[0095]

[0096] From the data in Table 4, it can be seen that compared with J, F, G, H, and I have better radiation resistance and light resistance. Under the radiation resistance test conditions, the transmittance before and after the color change is almost unchanged, and the stability is good. After more stringent exposure tests, the transmittance change rate before and after the color change is also less than 5%, which is much smaller than the change of the control group, and has the prospect of further commercial development and production of green energy-saving glass materials.

[0097] The above is only a preferred embodiment of the present invention, and does not limit the present invention in any form. Although the present invention has been disclosed as a preferred embodiment, it is not used to limit the present invention. Any technician familiar with this patent can make some changes or modify the technical contents suggested above into equivalent embodiments without departing from the scope of the technical solution of the present invention. However, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention without departing from the content of the technical solution of the present invention still fall within the scope of the solution of the present invention.

Claims

1. A benzofluorene photochromic compound, characterized in that: The structure of the benzofluorene photochromic compound is shown below:

2. Use of the benzofluorene photochromic compound according to claim 1 in the preparation of photochromic products, characterized in that: The photochromic product is selected from eyeglass lenses, optical lens products, glass products, and electronic consumer products.

3. Use of the benzofluorene photochromic compound according to claim 1 in the preparation of photochromic materials.

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