Fluorine-containing organic compounds and their use

Abstract

The application provides a fluorine-containing organic compound and a preparation method and application thereof. The fluorine-containing organic compound has a structure as shown in formula 1: wherein n is 40-60, R1 is a fluorine-containing alkyl group, R2 is selected from H or a methyl group, and R3 is selected from a tert-butyl group, a 2-cyanopropyl group or a 3-carboxyl-2-cyanopropyl group. The fluorine-containing organic compound obtained by introducing a fluorine-containing group into an organic structure has a lower refractive index. An ink prepared by using the fluorine-containing organic compound not only has a lower refractive index, but also effectively avoids precipitation and agglomeration problems compared with organic-inorganic resins. The ink containing the fluorine-containing organic compound has excellent stability and leveling.

Description

Technical Field

[0001] This invention belongs to the field of polymer materials technology, and particularly relates to a fluorine-containing organic compound and its applications. Background Technology

[0002] Leading panel manufacturers plan to apply low-refractive-index capping layers (CPLs) to OLED displays for smartphones, with commercialization expected as early as 2025. The CPL, formed on top of the cathode, helps direct light emitted from the emitting layer towards the front of the display panel. Currently, OLED screens widely use high-refractive-index CPL panels. Applying low-refractive-index CPLs on top of these can reduce light loss, further improve the optical efficiency of the display, and also have a positive effect on product lifespan. Dongjinsemichem, Raptor, and P&H Tech have all developed corresponding low-refractive-index products.

[0003] Low-refractive-index resins are mainly divided into organic resins and organic-inorganic hybrid resins. The refractive index (nD) of organic resins is typically between 1.31 and 1.39, while that of organic-inorganic hybrid resins is typically between 1.2 and 1.4. For organic-inorganic hybrid resins, because the inorganic portion is essentially a solid, it only exhibits liquid properties when dispersed within the organic monomers, thus making aggregation and precipitation risks unavoidable. Therefore, studying low-refractive-index organic resins is more feasible than studying low-refractive-index inorganic-organic hybrid resins. Summary of the Invention

[0004] This invention aims to at least partially solve one of the technical problems in the prior art. Therefore, one object of this invention is to provide a fluorinated organic compound and its applications.

[0005] In a first aspect, the present invention provides a fluorinated organic compound, the structure of which is shown in Formula 1: , Wherein, n is 40-60, R1 is a fluorinated alkyl group, R2 is selected from H or methyl, and R3 is selected from tert-butyl, 2-cyanopropyl or 3-carboxy-2-cyanopropyl.

[0006] According to the above-mentioned fluorinated organic compound provided by the present invention, in order to solve the problem of high refractive index of organic monomer system, the above-mentioned fluorinated organic compound obtained by introducing fluorinated groups into organic structure has a lower refractive index, and compared with organic and inorganic resins, it effectively avoids precipitation and agglomeration problems. The ink containing the fluorinated organic compound has excellent stability and leveling properties.

[0007] In some embodiments of the present invention, the refractive index of the fluorinated organic compound is 1.28-1.38, preferably 1.28-1.34, and more preferably 1.28-1.32.

[0008] According to the fluorinated organic compounds provided by the present invention, the fluorinated alkyl group has 2-20 carbon atoms.

[0009] Preferably, R1 includes one of perfluoroalkylmethyl, perfluoroalkylethyl, perfluoroalkylpropyl, perfluoroalkylbutyl, polyfluoroalkylmethyl, polyfluoroalkylethyl, polyfluoroalkylpropyl, and polyfluoroalkylbutyl.

[0010] More preferably, R1 is selected from or , where a is an integer from 0 to 15 and b is an integer from 1 to 4.

[0011] According to the fluorinated organic compound provided by the present invention, the number average molecular weight of the fluorinated organic compound is 1000-10000.

[0012] As an example, the fluorinated organic compound includes at least one of the following structures: , , , , , , , , , , , , , , , , , , , .

[0013] In some embodiments of the present invention, the method for using the above-mentioned fluorinated organic compounds includes: (1) N-acryloyloxysuccinimide and 2-methyl-2-propylbenzodithiolate undergo RAFT polymerization under the action of an initiator to obtain compound A; (2) Compound A and a fluorinated alcohol undergo a substitution reaction under the action of a catalyst to give compound B; (3) Compound B undergoes a reduction reaction under the action of a reducing agent to obtain compound C; (4) The compound C and the acryloyl chloride compounds undergo a substitution reaction under the action of an acidifying agent to obtain a fluorinated organic compound.

[0014] According to the method for preparing fluorinated organic compounds provided by the present invention, firstly, N-acryloyloxysuccinimide and 2-methyl-2-propylbenzodithiol salt undergo RAFT polymerization in an organic solvent under the action of an initiator to obtain compound A, as follows: Then, compound A and a fluorinated alcohol undergo a substitution reaction in an organic solvent under the action of a catalyst to give compound B, as shown in the following reaction process: Furthermore, compound B undergoes a reduction reaction in an organic solvent under the action of a reducing agent to give compound C, as shown in the following reaction process: Finally, compound C and acryloyl chloride compounds undergo a substitution reaction in an organic solvent under the action of an acidifying agent to give a fluorinated organic compound, as shown in the following reaction process: .

[0015] According to the method for preparing fluorinated organic compounds provided by the present invention, in step (1), the polymerization reaction occurs at a temperature of 75°C-85°C.

[0016] In some embodiments of the present invention, the initiator in step (1) includes, but is not limited to, azobisisobutyronitrile (AIBN), azobisisovalerate, azobisisoheptanenitrile, azoisobutylcyanoformamide, azobiscyclohexylformitrile, or dimethyl azobisisobutyrate.

[0017] In some embodiments of the present invention, the organic solvent in step (1) includes, but is not limited to, dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or toluene.

[0018] According to the method for preparing fluorinated organic compounds provided by the present invention, in step (2), the fluorinated alcohol compound includes one of perfluoroalkyl methanol, perfluoroalkyl ethanol, perfluoroalkyl propanol, perfluoroalkyl butanol, polyfluoroalkyl methanol, polyfluoroalkyl ethanol, polyfluoroalkyl propanol, and polyfluoroalkyl butanol; Preferably, the fluorinated alcohol compound includes one of tetrafluoropropanol, perfluorobutylethyl alcohol, perfluorohexylethyl alcohol, 2,2,3,3,3-pentafluoro-1-propanol, dodecafluoroheptanol, 3-perfluorooctylpropanol, 2-perfluoromethylethyl alcohol, 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, and 2,2,3,3,4,4,4-heptafluoro-1-butanol; According to the method for preparing fluorinated organic compounds provided by the present invention, in step (2), the substitution reaction occurs at room temperature for 5-7 hours.

[0019] In some embodiments of the present invention, the catalyst in step (2) includes, but is not limited to, triethylamine, N,N-diisopropylethylamine (DIPEA), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or pyridine.

[0020] In some embodiments of the present invention, the organic solvent in step (2) includes, but is not limited to, dichloromethane, dichloroethane, petroleum ether, tetrahydrofuran, or toluene.

[0021] According to the method for preparing fluorinated organic compounds provided by the present invention, in step (3), the reduction reaction occurs at a temperature of 45℃-55℃ for a time of 3h-5h.

[0022] In some embodiments of the present invention, the reducing agent in step (3) includes, but is not limited to, sodium borohydride, potassium borohydride, nickel borohydride, dithiothreitol, or tris(2-carbonylethyl)phosphine hydrochloride.

[0023] In some embodiments of the present invention, the organic solvent in step (3) includes, but is not limited to, methanol, ethanol, acetonitrile or acetone.

[0024] According to the method for preparing fluorinated organic compounds provided by the present invention, the acryloyl chloride compounds include acryloyl chloride or methacryloyl chloride.

[0025] In some embodiments of the present invention, the acid-coating agent in step (4) includes, but is not limited to, triethylamine, N,N-diisopropylethylamine (DIPEA), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or pyridine.

[0026] In some embodiments of the present invention, the substitution reaction in step (4) occurs at room temperature for 3.5 h to 4.5 h.

[0027] In some embodiments of the present invention, the organic solvent in step (4) includes, but is not limited to, dichloromethane, dichloroethane, petroleum ether, tetrahydrofuran, or toluene.

[0028] In a second aspect, the present invention provides an ink comprising the aforementioned fluorinated organic compound. Consequently, the ink has a low refractive index and, compared to organic-inorganic resins, effectively avoids precipitation and agglomeration problems, exhibiting excellent stability and leveling properties.

[0029] In some embodiments of the present invention, the ink comprises 20-60% of the fluorinated organic compound by weight percentage. Controlling the weight percentage of the fluorinated organic compound in the ink within the above range can effectively regulate the refractive index of the ink.

[0030] In some embodiments of the present invention, the refractive index of the fluorinated organic compound is 1.28-1.38. Using inks containing fluorinated organic compounds with a refractive index of 1.28-1.38 can reduce the overall refractive index of the ink and increase the leveling properties of the system.

[0031] In some embodiments of the present invention, the ink further comprises an initiator, preferably comprising 3%-10% of the total mass of the ink. Adding an initiator can promote the UV curing of the ink.

[0032] In some embodiments of this formulation, the initiator includes, but is not limited to, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (TPO), (2,4,6-trimethylbenzoyl)di(p-tolyl)phosphine oxide (TMO), phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (819), benzoyladium dimethyl ketal, 2,2-diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxy-cyclohexylbenzophenone, and 2-hydroxy-2-methyl-1-phenylpropanone.

[0033] In a third aspect, the present invention proposes the application of the above-mentioned ink in optical fiber coating, cable coating, AR / VR industry or display devices.

[0034] In a fourth aspect, the present invention provides an organic light-emitting device comprising a capping layer comprising the aforementioned fluorinated organic compound or the aforementioned ink. Consequently, the organic light-emitting device exhibits superior optical efficiency.

[0035] The present invention has at least the following technical effects: This invention introduces fluorine-containing groups into an organic structure to obtain fluorine-containing organic compounds with low refractive index. This not only effectively solves the problem of high refractive index of organic monolithic resins, but also effectively avoids precipitation and aggregation problems compared to organic-inorganic resins.

[0036] The ink provided by this invention has a lower refractive index and exhibits excellent stability and leveling properties. Furthermore, organic light-emitting devices prepared using the fluorinated organic compounds or inks of this invention demonstrate superior optical efficiency. Detailed Implementation

[0037] Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without inventive effort are within the scope of protection of this invention. The invention will now be described with reference to specific embodiments. It should be noted that these embodiments are merely descriptive and do not limit the invention in any way.

[0038] Example 1 (1) Preparation of compound A Prepare a 500mL three-necked flask and place it in an oven to ensure the reaction flask is dry. After heating to remove impurities, evacuate to room temperature. Purge the reaction flask with nitrogen and evacuate again. Repeat this step three times to replace the air in the reaction flask with nitrogen, ensuring the polymerization reaction proceeds under anhydrous and oxygen-free conditions. Add 33.40g (0.2mol) N-acryloyloxysuccinimide, 0.42g (2mmol) 2-methyl-2-propylbenzodithiol salt, 0.16g (1mmol) AIBN, and 200mL dioxane to the reaction flask sequentially. Turn on the stirrer at 800r / min to dissolve all the reactants in the solvent. Heat to 80℃ to carry out the reaction, and cool to room temperature after the reaction is complete. Concentrate the reaction solution, add isopropyl ether and water, extract, concentrate the organic phase, and concentrate the filtrate to obtain 13.52g of a pale yellow oil (compound A).

[0039] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0040] (2) Preparation of compound B Prepare a 250 mL three-necked flask. Add 10 g (1.28 mmol) of compound A, 6.6 g (50 mmol) of tetrafluoropropanol, 11.66 g (115.43 mmol) of triethylamine, and 150 mL of dichloromethane to the reaction flask in sequence. Stir magnetically and react at room temperature for 6 h. Wash with water to remove triethylamine, concentrate the organic phase to obtain a white solid, remove tetrafluoropropanol by slurrying with petroleum ether, and filter to obtain 12.7 g of white solid (compound B).

[0041] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.650 - 6.55(m, 5H), 4.13 - 3.74 (m, 263H), 1.63 - 1.41(s, 9H).

[0042] (3) Preparation of compound C Prepare a 250 mL three-necked flask. Add 8 g (1.12 mmol) of compound B, 5.72 g (151.31 mmol) of sodium borohydride, and 150 mL of methanol to the reaction flask in sequence. React at 50 °C for 4 h. After the reaction is complete, filter to remove insoluble matter, concentrate under reduced pressure to remove methanol, add dichloromethane and 1 N NaOH, extract, collect the aqueous phase, adjust the pH of the aqueous phase to 2-3 with 2 N HCl, precipitate solid, and filter to obtain 7.2 g of crude compound C.

[0043] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.57 (s, 1H), 4.13 - 3.74 (m, 263H), 1.63 - 1.41 (s, 9H).

[0044] (4) Preparation of compounds shown in formula 1-2 In a 100 mL three-necked flask, 5 g (0.57 mmol) of compound C, 5.22 g (51.72 mmol) of triethylamine, and 50 mL of dichloromethane were added sequentially. 4.68 g (51.72 mmol) of acryloyl chloride was added dropwise at 0-5 °C. After the addition was complete, the mixture was allowed to rise to room temperature and react for 4 h. The insoluble matter was removed by filtration, the filtrate was decolorized with silica gel, concentrated, and the crude product was purified by molecular distillation to obtain 4.77 g of a colorless transparent liquid (the compound shown in Formula 1-2). n=53.

[0045] The proton NMR spectra of the compounds shown in Formula 1-2 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.56 (s, 1H), 5.57 (s, 1H), 4.13 - 3.74 (m, 263H), 1.63 - 1.41 (s, 9H).

[0046] Example 2 (1) Preparation of compound A The difference between the preparation process of compound A in Example 2 and that in Example 1 is that perfluorobutylethyl alcohol was used in Example 2.

[0047] The proton NMR data for compound A are as follows: 1H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0048] (2) Preparation of compound B In the preparation of compound B in Example 2, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.50 g of white solid compound B was obtained.

[0049] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.650 - 6.55(m, 5H), 4.13 - 3.74 (m, 367H), 1.63 - 1.41(s, 9H).

[0050] (3) Preparation of compound C In the preparation of compound C in Example 2, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 8.31 g of white solid compound C was finally obtained.

[0051] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 4.13 - 3.74(m, 367H), 1.63 - 1.41(s, 9H).

[0052] (4) Preparation of compounds shown in formulas 1-4 The compound shown in Formulas 1-4 in Example 2 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and finally 5.11 g of colorless transparent liquid was obtained. n=52.

[0053] The proton NMR spectra of the compounds shown in Formulas 1-4 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 4.13 - 3.74 (m, 367H), 1.63-1.41(s, 9H).

[0054] Example 3 (1) Preparation of compound A The difference between the preparation process of compound A in Example 3 and that in Example 1 is that perfluorohexylethyl alcohol was used in Example 3.

[0055] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0056] (2) Preparation of compound B In the preparation of compound B in Example 3, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.28 g of white solid compound B was obtained.

[0057] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 371H), 1.57 - 1.26(s, 9H).

[0058] (3) Preparation of compound C In the preparation of compound C in Example 3, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 7.87 g of white solid compound C was finally obtained.

[0059] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 4.13 - 3.74 (m, 371H), 1.63 - 1.41 (s, 9H).

[0060] (4) Preparation of compounds shown in formulas 1-6 The compounds shown in Formulas 1-6 in Example 3 were prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.12 g of colorless transparent liquid was finally obtained. n=54.

[0061] The proton NMR spectra of the compounds shown in Formulas 1-6 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 4.13 - 3.74 (m, 377H), 1.63-1.41(s, 9H).

[0062] Example 4 (1) Preparation of compound A The difference between the preparation process of compound A in Example 4 and that in Example 1 is that 2-perfluorooctylethyl alcohol was used in Example 4.

[0063] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0064] (2) Preparation of compound B In the preparation of compound B in Example 4, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.34 g of white solid compound B was obtained.

[0065] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 373H), 1.57 - 1.26(s, 9H).

[0066] (3) Preparation of compound C In the preparation of compound C in Example 4, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 7.91g of white solid compound C was finally obtained.

[0067] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 373H), 1.57 - 1.26 (s, 9H).

[0068] (4) Preparation of compounds shown in formulas 1-8 The compound shown in Formulas 1-8 in Example 4 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and finally 5.01 g of colorless transparent liquid was obtained. n=52.

[0069] The proton NMR spectra of the compounds shown in Formulas 1-8 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 363H), 1.57-1.26(s, 9H).

[0070] Example 5 (1) Preparation of compound A The difference between the preparation process of compound A in Example 5 and that in Example 1 is that 2,2,3,3,3-pentafluoro-1-propanol was used in Example 5.

[0071] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0072] (2) Preparation of compound B In the preparation of compound B in Example 5, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.77 g of white solid compound B was obtained.

[0073] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 266H), 1.57 - 1.26(s, 9H).

[0074] (3) Preparation of compound C In the preparation of compound C in Example 5, compound B prepared in step (2) was used, and the reaction conditions were the same as in Example 1. Finally, 8.03 g of white solid compound C was obtained.

[0075] The proton NMR data for compound C are as follows: 1H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 266H), 1.57 - 1.26 (s, 9H).

[0076] (4) Preparation of compounds shown in formula 1-10 The compound shown in Formulas 1-10 in Example 5 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.26 g of colorless transparent liquid was finally obtained. n=53.

[0077] The proton NMR data of the compounds shown in Formulas 1-10 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 6.51 (dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 266H), 1.57 - 1.26 (s, 9H).

[0078] Example 6 (1) Preparation of compound A The difference between the preparation process of compound A in Example 6 and that in Example 1 is that in Example 6, dodecafluoroheptanol was used.

[0079] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0080] (2) Preparation of compound B In the preparation of compound B in Example 6, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.17 g of white solid compound B was obtained.

[0081] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 267H), 1.57 - 1.26(s, 9H).

[0082] (3) Preparation of compound C In the preparation of compound C in Example 6, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 7.65g of white solid compound C was finally obtained.

[0083] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 267H), 1.57 - 1.26 (s, 9H).

[0084] (4) Preparation of compounds shown in formula 1-12 The compound shown in Formulas 1-12 in Example 6 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.65 g of colorless transparent liquid was finally obtained. n=53.

[0085] The proton NMR spectra of the compounds shown in Formula 1-12 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 267H), 1.57-1.26(s, 9H).

[0086] Example 7 (1) Preparation of compound A The difference between the preparation process of compound A in Example 7 and that in Example 1 is that 3-perfluorooctylpropanol was used in Example 7.

[0087] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0088] (2) Preparation of compound B In the preparation of compound B in Example 7, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.25 g of white solid compound B was obtained.

[0089] The proton NMR data for compound B are as follows: 1H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 460H), 1.57 - 1.26(s, 9H).

[0090] (3) Preparation of compound C In the preparation of compound C in Example 7, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 7.85g of white solid compound C was finally obtained.

[0091] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 460H), 1.57 - 1.26 (s, 9H).

[0092] (4) Preparation of compounds shown in formula 1-16 The compound shown in Formula 1-16 in Example 7 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.26 g of colorless transparent liquid was finally obtained. n=51.

[0093] The proton NMR data of the compounds shown in Formula 1-14 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 460H), 1.57-1.26(s, 9H).

[0094] Example 8 (1) Preparation of compound A The difference between the preparation process of compound A in Example 8 and that in Example 1 is that 2-perfluoromethylethyl alcohol was used in Example 8.

[0095] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0096] (2) Preparation of compound B In the preparation of compound B in Example 8, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.98 g of white solid compound B was obtained.

[0097] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 371H), 1.57 - 1.26(s, 9H).

[0098] (3) Preparation of compound C In the preparation of compound C in Example 8, compound B prepared in step (2) was used, and the reaction conditions were the same as in Example 1. Finally, 7.33g of white solid compound C was obtained.

[0099] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26 (s, 9H).

[0100] (4) Preparation of compounds shown in formula 1-14 The compound shown in Formula 1-14 in Example 8 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.62 g of colorless transparent liquid was finally obtained. n=52.

[0101] The proton NMR data of the compounds shown in Formula 1-14 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 363H), 1.57-1.26(s, 9H).

[0102] Example 9 (1) Preparation of compound A The difference between the preparation process of compound A in Example 9 and that in Example 1 is that 2,2,3,3,4,4,5,5-octafluoro-1-pentanol was used in Example 9.

[0103] The proton NMR data for compound A are as follows: 1H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0104] (2) Preparation of compound B In the preparation of compound B in Example 9, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.19 g of white solid compound B was obtained.

[0105] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 274H), 1.57 - 1.26(s, 9H).

[0106] (3) Preparation of compound C In the preparation of compound C in Example 9, compound B prepared in step (2) was used, and the reaction conditions were the same as in Example 1. Finally, 7.28 g of white solid compound C was obtained.

[0107] The proton NMR data for compound C are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 275H), 1.57 - 1.26 (s, 9H).

[0108] (4) Preparation of compounds shown in formula 1-18 The compound shown in Formula 1-18 in Example 9 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and finally 4.07 g of colorless transparent liquid was obtained. n=55.

[0109] The proton NMR data of the compounds shown in Formula 1-18 are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 6.51(dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 274H), 1.57-1.26(s, 9H).

[0110] Example 10 (1) Preparation of compound A The difference between the preparation process of compound A in Example 10 and that in Example 1 is that 2,2,3,3,4,4,4-heptafluoro-1-butanol was used in Example 10.

[0111] The proton NMR data for compound A are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 367H), 1.57 - 1.26(s, 9H).

[0112] (2) Preparation of compound B In the preparation of compound B in Example 10, compound A prepared in step (1) was used, and the reaction conditions were the same as in Example 1. Finally, 8.17 g of white solid compound B was obtained.

[0113] The proton NMR data for compound B are as follows: 1 H NMR (500 MHz, Chloroform-d) δ 7.540 - 6.32(m, 5H), 3.88 - 2.44 (m, 261H), 1.57 - 1.26(s, 9H).

[0114] (3) Preparation of compound C In the preparation of compound C in Example 10, compound B prepared in step (2) was used. The reaction conditions were the same as in Example 1, and 7.28 g of white solid compound C was finally obtained.

[0115] The 1H NMR data of compound C are as follows: 1H NMR (500 MHz, Chloroform-d) δ 5.32 (s, 1H), 3.88 - 2.44 (m, 261H), 1.57 - 1.26 (s, 9H).

[0116] (4) Preparation of compounds shown in formula 1-20 The compound shown in Formula 1-20 in Example 10 was prepared using compound C prepared in step (3) under the same reaction conditions as in Example 1, and 4.44 g of colorless transparent liquid was finally obtained. n=52 The proton NMR data of the compounds shown in Formula 1-20 are as follows: 1H NMR (500 MHz, Chloroform-d) δ 6.51 (dd, J=17.1, 10.4Hz, 1H), 6.28 (d, J=16.3Hz, 1H), 5.84 (d, J=10.4Hz, 1H), 5.32 (s, 1H), 3.88 - 2.44 (m, 261H), 1.57 - 1.26 (s, 9H).

[0117] To verify the refractive index of the fluorinated organic compounds of the present invention, the fluorinated organic compounds obtained in Examples 1-10 were tested using an Abbe refractometer: The liquid to be tested was added to the surface of the refracting prism using a clean dropper, and the light-gathering prism was covered and locked with a handwheel, ensuring that the liquid layer was uniform, filled the field of view, and was free of air bubbles. The light-shielding plate was opened, the reflector was closed, and the eyepiece diopter was adjusted to make the crosshairs clear. At this time, the handwheel was rotated and the position of the light-dark boundary line was found in the eyepiece field of view. The handwheel was then rotated again until the boundary line was free of any color. The handwheel was finely adjusted so that the boundary line was located in the center of the crosshairs. The condenser lens was then rotated appropriately. The value displayed below the eyepiece field of view at this time is the refractive index of the liquid being tested.

[0118] The results of the refractive index determination of the fluorinated organic compounds in Examples 1-10 are shown in Table 1.

[0119] Table 1

[0120] As can be seen from Table 1, the refractive index of the fluorinated organic compounds in the embodiments of the present invention is less than 1.37, that is, the refractive index of the fluorinated organic compounds in the embodiments of the present invention is between 1.28 and 1.37. In particular, the refractive index of some compounds is between 1.28 and 1.33, which has a low refractive index and effectively avoids precipitation and agglomeration problems compared with organic and inorganic resins.

[0121] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A fluorine-containing organic compound, characterized in that, The structure of the fluorine-containing organic compound is shown in Formula 1: ， Wherein, n is 40-60, R1 is selected from fluorinated alkyl groups, R2 is selected from H or methyl, and R3 is selected from tert-butyl, 2-cyanopropyl or 3-carboxy-2-cyanopropyl.

2. The fluorinated organic compound according to claim 1, characterized in that, The fluorinated alkyl group has 2-20 carbon atoms; Preferably, R1 includes one of perfluoroalkylmethyl, perfluoroalkylethyl, perfluoroalkylpropyl, perfluoroalkylbutyl, polyfluoroalkylmethyl, polyfluoroalkylethyl, polyfluoroalkylpropyl, and polyfluoroalkylbutyl. More preferably, R1 is selected from or , where a is an integer from 0 to 15 and b is an integer from 1 to 4.

3. The fluorinated organic compound according to claim 1, characterized in that, The number average molecular weight of the fluorinated organic compound is 1000-10000.

4. The fluorinated organic compound according to any one of claims 1-3, characterized in that, The fluorinated organic compound includes at least one of the following structures: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 5. An ink, characterized in that, Includes the fluorinated organic compound described in any one of claims 1-4.

6. The ink according to claim 5, characterized in that, The ink comprises 20-60% of the fluorinated organic compound by weight percentage.

7. The ink according to claim 5, characterized in that, The refractive index of the fluorinated organic compound is 1.28-1.

38.

8. The ink according to claim 5, characterized in that, The ink further comprises an initiator; preferably, the initiator is selected from one or more of 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, (2,4,6-trimethylbenzoyl)di(p-tolyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, benzoyladium dimethyl ketal, 2,2-diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxy-cyclohexylbenzophenone, and 2-hydroxy-2-methyl-1-phenylpropanone.

9. The use of the ink according to any one of claims 5 to 8 in optical fiber coating, cable coating, AR / VR industry or display device.

10. An organic light-emitting device, comprising a capping layer, characterized in that, The coating layer comprises a fluorinated organic compound as described in any one of claims 1-4 or an ink as described in any one of claims 5-8.

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