N-heterocyclic carbene palladium complex as well as preparation method and application thereof

Abstract

The invention discloses an N-heterocyclic carbene palladium complex as well as a preparation method and application thereof. The structural formula of the N-heterocyclic carbene palladium complex is as shown in a formula (I): # imgabs0 # formula (I), according to the invention, an alkoxy group is introduced into a framework of the N-heterocyclic carbene palladium complex, so that the yield of catalytic preparation of the dioctyl fluorene copolymer is effectively improved, and the dioctyl fluorene copolymer with high molecular weight can be obtained.

Description

Technical Field

[0001] The present invention belongs to the technical field of palladium complexes, and in particular relates to an N-heterocyclic carbene palladium complex, a preparation method thereof, and an application thereof. Background Art

[0002] Perovskite solar cells are a very promising type of solar cells that have emerged in recent years, and have the advantages of high photoelectric conversion efficiency, simple fabrication, and low cost. The photoelectric conversion efficiency is one of the important performances for measuring the quality of perovskite solar cells. At present, there are mainly two technical means to improve the photoelectric conversion efficiency of perovskite solar cells. One is to optimize the structure or regulate the morphology of each layer of the perovskite solar cell to optimize the interfacial performance; the other is to change the material composition of the perovskite solar cell and develop hole transport layer, perovskite absorption layer or electron transport layer materials with better performance.

[0003] The structure of the perovskite solar cell includes a substrate layer, an electron transport layer, a perovskite light absorption layer, a hole transport layer, and a metal back electrode. Among them, in the perovskite solar cell, the hole transport layer material plays an important role in the extraction and transport of carriers, suppressing carrier recombination, protecting the perovskite layer, etc. Therefore, developing highly efficient and stable hole transport materials is a research hotspot in the field of perovskite solar cells.

[0004] As a hole transport material, dioctylfluorene copolymer has broad potential application value. At present, such copolymers are mainly prepared by Suzuki and Stille coupling polymerization methods, but both of these polymerization methods require pre-functionalization of the comonomers to prepare their corresponding halides and metal tin compounds or borate derivatives. The synthesis conditions are harsh, the monomer synthesis reaction steps are many, the cost is high, and the prepared metal tin compounds have poor stability and are not easy to store.

[0005] To solve the defects of preparing fluorene copolymers by Suzuki and Stille coupling polymerization methods, scientific researchers have applied palladium complexes to the catalytic preparation of fluorene copolymers, such as Pd(OAc)2, PdCl2, Pd2(dba)3, etc., but the yields of the prepared fluorene copolymers are not high and the molecular weights are not high. Therefore, developing a palladium complex for preparing high-molecular-weight dioctylfluorene copolymer with high catalytic yield has certain market value. Summary of the Invention

[0006] Aiming at the above deficiencies in the prior art, the present invention provides an N-heterocyclic carbene palladium complex. By introducing an alkoxy group into the skeleton of the N-heterocyclic carbene palladium complex, the yield of catalytic preparation of dioctylfluorene copolymer is effectively improved, and it is beneficial to obtain high-molecular-weight dioctylfluorene copolymer.

[0007] The object of the present invention is to provide an N - heterocyclic carbene palladium complex, and the structural formula of the N - heterocyclic carbene palladium complex is shown as formula (Ⅰ):

[0008]

[0009] Wherein, R is methoxy or hydrogen.

[0010] Another object of the present invention is to provide a preparation method of the above - mentioned N - heterocyclic carbene palladium complex, which comprises the following steps:

[0011] S1. React 2,6 - diisopropylaniline with triethyl orthoformate to obtain an amino - imine compound;

[0012] S2. React the amino - imine compound with bromo - methoxyacetophenone to obtain a methoxy - substituted amino - imine compound;

[0013] S3. React the methoxy - substituted amino - imine compound with acetic anhydride and hydrochloric acid to obtain a methoxy - substituted amino - imine salt;

[0014] S4. React the methoxy - substituted amino - imine salt with 3 - chloropyridine and palladium chloride to obtain an N - heterocyclic carbene palladium complex.

[0015] Preferably, in S1, the molar ratio of 2,6 - diisopropylaniline to triethyl orthoformate is 1.5 - 2.5:1.

[0016] Preferably, in S1, the solvent for the reaction is acetic acid.

[0017] Preferably, in S1, the reaction temperature is 140 - 160 °C and the time is 18 - 30 hours.

[0018] Preferably, in S1, the reaction is carried out under a nitrogen atmosphere.

[0019] Preferably, in S2, the molar ratio of the amino - imine compound to bromo - methoxyacetophenone is 1 - 1.5:1 - 1.5.

[0020] Preferably, in S2, the solvent for the reaction is N,N - diisopropylethylamine.

[0021] Preferably, in S2, the reaction temperature is 120 - 140 °C and the time is 18 - 30 hours.

[0022] Preferably, in S2, the reaction is carried out under a nitrogen atmosphere.

[0023] Preferably, in S3, the dosage ratio of the methoxy - substituted amino - imine compound, acetic anhydride and hydrochloric acid is 1 mmol:1.8 - 2.4 mL:1.2 - 1.8 mL.

[0024] Preferably, in S3, the solvent for the reaction is toluene.

[0025] Preferably, in S3, the temperature of the reaction is 100 - 120 °C and the time is 40 - 55 hours.

[0026] Preferably, in S4, the molar ratio of the methoxy-substituted aminoiminium salt, 3-chloropyridine, and palladium chloride is 1:4 - 8:1.

[0027] Preferably, in S4, the solvent for the reaction is acetone.

[0028] Preferably, in S4, the temperature of the reaction is 50 - 70 °C and the time is 6 - 10 hours.

[0029] Preferably, in S4, the reaction is carried out under the action of a base, and the base is potassium carbonate.

[0030] Another object of the present invention is to provide the use of the azole carbene palladium complex or the azole carbene palladium complex prepared by the preparation method of the azole carbene palladium complex in the catalytic Sonogashira coupling polymerization reaction.

[0031] Another object of the present invention is to provide the use of the azole carbene palladium complex or the azole carbene palladium complex prepared by the preparation method of the azole carbene palladium complex in the reaction of catalyzing 3,5-dichloropyridine and hydroxy-substituted 9,9-dioctylfluorene in the reaction.

[0032] Another object of the present invention is to provide a 9,9-dioctylfluorene copolymer, and the structural formula of the 9,9-dioctylfluorene copolymer is shown in formula (II):

[0033]

[0034] Among them, the number average molecular weight of the 9,9-dioctylfluorene copolymer is 8 - 16.5 KDa, and the PDI is 2 - 2.5.

[0035] Compared with the prior art, the present invention has the following beneficial effects:

[0036] (1) By introducing an alkoxy group into the skeleton of the azole carbene palladium complex, the present invention effectively improves the yield of the catalytic preparation of the dioctylfluorene copolymer and is beneficial to obtaining a high molecular weight dioctylfluorene copolymer.

[0037] (2) The azole carbene palladium complex provided by the present invention has high stability. Applying the polymerization reaction, it can maintain good reaction activity at 100 °C and can obtain a high yield and high molecular weight dioctylfluorene copolymer. Detailed implementation manners

[0038] In order to enable those skilled in the art to better understand the technical solutions in the present invention, the technical solutions of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts shall fall within the scope of protection of the present invention.

[0039] All raw materials of the present invention can be obtained through commercial channels.

[0040] The preparation process of the N-heterocyclic carbene palladium complex in the embodiment of the present invention is as follows:

[0041]

[0042] The structure of the hydroxy-substituted 9,9-dioctylfluorene is as follows:

[0043] The preparation process of the 9,9-dioctylfluorene copolymer in the embodiment of the present invention is as follows:

[0044]

[0045] Example 1

[0046] This example provides an aminoimine compound A1, and its preparation method includes the following steps:

[0047] 2,6-Diisopropylaniline (20 mmol) and triethyl orthoformate (10 mmol) were successively added to a 100 ml two-necked reaction flask, 0.3 ml of AcOH was added, and the reaction was refluxed under N2 protection at 160 °C for 24 h. After the reaction was completed, it was cooled to room temperature, ice-cold absolute ethanol was added, and a large amount of white solid was precipitated by stirring. It was filtered by suction, and the white solid was rinsed with ice-cold absolute ethanol 2-3 times, dried, and the product was collected to obtain the aminoimine compound A1 with a yield of 90%; the 13C and 1H NMR spectra of the aminoimine compound A1 are as follows:

[0048] 1 H NMR (400 MHz, CDCl3) δ 7.16, 7.13, 7.11, 7.07, 7.04, 7.01, 3.27, 3.25, 3.24, 3.22, 3.20, 3.18, 3.17, 3.15, 3.13, 3.12, 3.11, 3.11, 3.09, 3.07, 1.24, 1.23, 1.14, 1.12, 1.11, 1.09, 1.03, 1.01.

[0049] 1313C NMR (101 MHz, CDCl3) δ 153.20, 146.53, 144.77, 142.45, 141.46, 138.07, 132.15, 126.78, 124.31, 122.73, 122.67, 122.30, 122.11, 76.31, 75.99, 75.68, 27.12, 26.98, 23.37, 22.82, 22.46, 21.66.

[0050] Example 2

[0051] This example provides a methoxy-substituted aminoimine compound B1, and its preparation method includes the following steps:

[0052] Add aminoimine compound A1 (3 mmol), α-bromo-4-methoxyacetophenone (3 mmol), and 5 mL of N,N-diisopropylethylamine into a 100 ml three-necked reaction flask in sequence. Under N2 protection, reflux and react at 130 °C for 24 h. After the reaction is completed, add 10 mL of H2O to quench the reaction system, then extract with ethyl acetate as the organic phase for 2 - 3 times. Collect the ethyl acetate organic phase layer and add anhydrous Na2SO4 for drying. After distilling off the solvent under reduced pressure, add 20 mL of anhydrous ethanol to rapidly precipitate a white solid. After placing it in the refrigerator for 2 h, filter off the solvent to obtain a large amount of white solid. After drying, the methoxy-substituted aminoimine compound B1 is obtained, and the yield is 77%; the 1H and 13C NMR spectra of the methoxy-substituted aminoimine compound B1 are as follows:

[0053] 1 1H NMR (400 MHz, CDCl3) δ 8.06, 8.04, 7.33, 7.32, 7.23, 7.21, 7.09, 7.07, 6.95, 6.93, 5.03, 3.86, 3.74, 3.72, 3.71, 3.69, 3.67, 3.66, 3.64, 3.31, 3.29, 3.27, 3.25, 3.24, 3.22, 3.20, 1.33, 1.31, 1.21, 1.20, 1.18.

[0054] 13 13C NMR (101 MHz, CDCl3) δ 191.08, 162.29, 149.59, 147.40, 145.74, 138.92, 137.96, 129.22, 128.27, 127.77, 123.41, 121.63, 121.53, 112.65, 76.31, 75.99, 75.67, 54.49, 54.38, 26.93, 26.62, 23.93, 23.50, 22.66.

[0055] Example 3

[0056] This example provides a methoxy-substituted aminoimine compound B2. The difference from Example 2 is only that α-bromo-4-methoxyacetophenone is replaced with bromo-3,4-dimethoxyacetophenone to obtain an orange solid, namely methoxy-substituted aminoimine compound B2, with a yield of 82%; the nuclear magnetic carbon-hydrogen spectrum of methoxy-substituted aminoimine compound B2 is as follows:

[0057] 1 H NMR(400MHz,CDCl3)δ7.73,7.73,7.71,7.71,7.59,7.59,7.32,7.31,7.23,7.21,7.08,7.08,7.06,7.00,6.98,6.98,6.96,6.89,6.87,5.03,3.73,3.72,3.70,3.68,3.67,3.65,3.63,3.30,3.28,3.26,3.24,3.23,3.21,3.19,1.33,1.31,1.30,1.29,1.28,1.28,1.27,1.21,1.19,1.18.

[0058] 13 C NMR(101MHz,CDCl3)δ191.17,152.14,149.59,148.06,147.39,145.70,138.89,138.01,128.47,127.81,123.43,121.68,121.56,121.34,109.36,108.85,76.32,76.01,75.69,55.00,54.98,54.45,30.56,26.96,26.64,23.91,23.53,22.67,21.63,13.10.

[0059] Example 4

[0060] This example provides a methoxy-substituted aminoimine salt C1, and its preparation method includes the following steps:

[0061] Weigh 1.0 mmol of the methoxy-substituted aminoimine compound B1 and add it to a 50-ml stoppered three-necked flask. Then, add 2 ml of toluene, 2 ml of acetic anhydride, and 1.5 ml of HCl in sequence to dissolve it. Note that when adding hydrochloric acid, the three-necked flask should be placed in ice water, sealed with a rubber stopper, and reacted at 110 °C for 48 h. After the reaction is completed, cool it to room temperature, add 10 ml of water, extract it with ethyl acetate 2-3 times, take the ethyl acetate layer, add anhydrous sodium sulfate to dry for 2 h, and then rotary evaporate the solvent for column chromatography. First, elute the impurity part with ethyl acetate, and then elute the carbene salt part with methanol. Distill off the eluent to obtain a large amount of white solid, dry it, and obtain the methoxy-substituted aminoimine salt C1 with a yield of 78%; the 13C and 1H NMR spectra of the methoxy-substituted aminoimine salt C1 are as follows:

[0062] 1 H NMR(400MHz,CDCl3)δ10.74,10.74,7.82,7.82,7.50,7.48,7.28,7.24,7.23,7.11,7.09,6.77,6.75,3.70,2.53,2.51,2.50,2.48,2.46,2.44,2.44,2.40,2.38,2.37,2.35,2.33,2.31,2.30,1.25,1.23,1.23,1.23,1.21,1.21,1.20,1.18,1.16,1.15,0.98,0.96.

[0063] 13 C NMR(101MHz,CDCl3)δ161.28,145.14,144.90,140.02,136.84,132.29,131.99,130.08,129.41,128.74,125.05,124.65,120.59,116.36,114.75,77.46,77.15,76.83,55.49,29.35,29.25,25.13,24.77,23.85,22.65.

[0064] Example 5

[0065] This example provides a methoxy-substituted aminoimine salt C2. The difference from Example 4 is only that the methoxy-substituted aminoimine compound B1 is replaced with the methoxy-substituted aminoimine compound B2 to obtain a white solid, namely the methoxy-substituted aminoimine salt C2, with a yield of 65%; the 13C and 1H NMR spectra of the methoxy-substituted aminoimine salt C2 are as follows:

[0066] 11H NMR (400 MHz, CDCl3) δ 11.31 (s, 1H), 7.89 (s, 2H), 7.60 (s, 2H), 7.41 (d, J = 6.9 Hz, 4H), 7.19 (s, 2H), 2.66 (d, J = 43.9 Hz, 8H), 1.30 (s, 18H), 1.17 (s, 12H).

[0067] 13 13C NMR (101 MHz, CDCl3) δ 152.23, 140.37, 137.54, 131.90, 131.23, 129.50, 127.79, 125.25, 122.97, 121.01, 35.62, 31.34, 24.73, 14.78.

[0068] Example 6

[0069] This example provides an N-heterocyclic carbene palladium complex D1, and its preparation method includes the following steps:

[0070] Weigh methoxy-substituted amino imine salt C1 (0.5 mmol), palladium chloride (0.5 mmol), potassium carbonate (4 mmol), and 3-chloropyridine (3 mmol) into a reaction flask, add 2 - 4 ml of acetone to cover the solids, react at 60 °C for 8 h, and after treatment, a pale yellow solid, namely N-heterocyclic carbene palladium complex D1, is obtained with a yield of 55%; the 1H and 13C NMR spectra of N-heterocyclic carbene palladium complex D1 are as follows:

[0071] 1 1H NMR (400 MHz, CDCl3) δ 8.64, 8.63, 8.56, 8.56, 8.55, 8.54, 7.56, 7.56, 7.56, 7.55, 7.54, 7.54, 7.54, 7.53, 7.52, 7.51, 7.51, 7.50, 7.49, 7.39, 7.37, 7.33, 7.32, 7.09, 7.07, 7.07, 7.05, 6.90, 6.90, 6.89, 6.88, 6.87, 6.87, 6.74, 6.73, 6.73, 6.72, 6.71, 6.70, 3.75, 3.38, 3.36, 3.35, 3.33, 3.31, 3.30, 3.28, 3.25, 3.24, 3.22, 3.20, 3.19, 3.17, 3.15, 1.56, 1.54, 1.50, 1.48, 1.15, 1.13, 0.78, 0.76.

[0072] 1313C NMR (101 MHz, CDCl3) δ 158.71, 153.14, 149.44, 148.42, 145.70, 145.48, 136.38, 136.11, 134.39, 132.93, 130.91, 129.35, 129.22, 127.44, 123.84, 123.31, 123.07, 121.24, 119.54, 113.06, 76.32, 76.00, 75.69, 54.24, 27.79, 27.64, 25.46, 24.39, 23.41, 22.14.

[0073] Example 7

[0074] This example provides an N-heterocyclic carbene palladium complex D2, and its preparation method includes the following steps:

[0075] Weigh methoxy-substituted amino imine salt C2 (0.5 mmol), palladium chloride (0.5 mmol), potassium carbonate (4 mmol), and 3-chloropyridine (3 mmol) into a reaction flask, add 2 - 4 ml of acetone to cover the solids, react at 60 °C for 8 h, and after treatment, a pale yellow solid, i.e., N-heterocyclic carbene palladium complex D2, is obtained with a yield of 52%; the nuclear magnetic carbon and hydrogen spectra of N-heterocyclic carbene palladium complex D2 are as follows:

[0076] 1 1H NMR (400 MHz, CDCl3) δ 8.64, 8.63, 8.57, 8.56, 8.55, 8.55, 7.57, 7.57, 7.57, 7.56, 7.55, 7.55, 7.54, 7.54, 7.53, 7.52, 7.51, 7.49, 7.39, 7.37, 7.35, 7.33, 7.09, 7.08, 7.07, 7.06, 6.81, 6.80, 6.79, 6.78, 6.66, 6.65, 6.63, 6.61, 6.22, 6.21, 3.83, 3.83, 3.42, 3.37, 3.36, 3.35, 3.33, 3.31, 3.30, 3.28, 3.25, 3.24, 3.22, 3.21, 3.19, 3.17, 3.16, 1.55, 1.53, 1.50, 1.48, 1.15, 1.14, 0.79, 0.77.

[0077] 1313C NMR (101 MHz, CDCl3) δ 153.27, 149.46, 148.43, 148.17, 147.58, 145.92, 145.47, 136.41, 135.86, 134.36, 133.07, 130.94, 129.41, 129.26, 123.97, 123.32, 123.11, 121.42, 119.72, 119.17, 110.12, 76.32, 76.00, 75.69, 54.63, 27.81, 27.69, 25.46, 24.37, 23.54, 22.17.

[0078] Example 8

[0079] This example provides a 9,9-dioctylfluorene copolymer E1, and its preparation method includes the following steps:

[0080] Under a nitrogen atmosphere, 3,5-dichloropyridine (0.5 mmol), hydroxy-substituted 9,9-dioctylfluorene (0.5 mmol), N-heterocyclic carbene palladium complex D1 (0.5 mol%), 2,2-dimethylpropanoic acid (30 mol%), and K2CO3 (1.5 mmol) were added to 4 mL of DMAc, and stirred at 100 °C for 24 h. After cooling to room temperature, the resulting mixture was poured into cold methanol, and a large amount of yellow precipitate was produced. The product was obtained by filtration, washed successively with distilled water and methanol, and then the washed precipitate was purified with n-hexane in a Soxhlet extractor to obtain a yellow solid, namely 9,9-dioctylfluorene copolymer E1. The yield was 95.5%, the number-average molecular weight of 9,9-dioctylfluorene copolymer E1 was 16.2 KDa, the weight-average molecular weight was 40.3 KDa, and the PDI was 2.5.

[0081] Example 9

[0082] This example provides a 9,9-dioctylfluorene copolymer E2, and its preparation method includes the following steps:

[0083] Under a nitrogen atmosphere, 3,5-dichloropyridine (0.5 mmol), hydroxy-substituted 9,9-dioctylfluorene (0.5 mmol), N-heterocyclic carbene palladium complex D2 (0.5 mol%), 2,2-dimethylpropanoic acid (30 mol%), and K2CO3 (1.5 mmol) were added to 4 mL of DMAc, and the mixture was stirred at 100 °C for 24 h. After cooling to room temperature, the resulting mixture was poured into cold methanol, and a large amount of yellow precipitate was produced. The product was obtained by filtration, washed successively with distilled water and methanol, and then the washed precipitate was purified with n-hexane in a Soxhlet extractor to obtain a yellow solid, namely 9,9-dioctylfluorene copolymer E1, with a yield of 82.5%. The number-average molecular weight of 9,9-dioctylfluorene copolymer E2 was 8.0 KDa, the weight-average molecular weight was 17.8 KDa, and the PDI was 2.2.

[0084] The N-heterocyclic carbene palladium complexes prepared in Examples 6-7 of the present invention are used for the preparation of dioctylfluorene copolymers, which can maintain good reaction activity at 100 °C, and dioctylfluorene copolymers with high yield and high molecular weight can be obtained. The N-heterocyclic carbene palladium complexes have high stability.

[0085] Finally, it should be noted that the above examples are only used to illustrate the technical solutions of the present invention and are not intended to limit them. Although the present invention has been described in detail with reference to the above examples, those of ordinary skill in the art should understand that after reading the specification of this application, they can still modify the specific embodiments of the present invention or make equivalent substitutions. However, these modifications or changes are all within the scope of the claims of the present invention pending approval.

Claims

1. A N-heterocyclic carbene palladium complex, characterized in that, The structural formula of the N-heterocyclic carbene palladium complex is shown in Formula (I): Formula (I) Wherein, R is a methoxy group or hydrogen.

2. The preparation method of the N-heterocyclic carbene palladium complex according to claim 1, characterized in that, It includes the following steps: S1. 2,6-Diisopropylaniline reacts with triethyl orthoformate to obtain an aminoimine compound; S2. The aminoimine compound and bromo-methoxyacetophenone react to obtain a methoxy-substituted aminoimine compound; S3. The methoxy-substituted aminoimine compound reacts with acetic anhydride and hydrochloric acid to obtain a methoxy-substituted aminoimine salt; S4. The methoxy-substituted aminoimine salt reacts with 3-chloropyridine and palladium chloride to obtain an N-heterocyclic carbene palladium complex.

3. The preparation method of the N-heterocyclic carbene palladium complex according to claim 2, characterized in that, In S1, the molar ratio of 2,6-diisopropylaniline to triethyl orthoformate is 1.5 - 2.5:

1.

4. The preparation method of the N-heterocyclic carbene palladium complex according to claim 2, characterized in that, In S1, the solvent for the reaction is acetic acid; The temperature of the reaction is 140 - 160 °C, and the time is 18 - 30 hours; The reaction is carried out under a nitrogen atmosphere.

5. The preparation method of the N-heterocyclic carbene palladium complex according to claim 2, characterized in that, In S2, the molar ratio of the aminoimine compound to bromomethoxyacetophenone is 1 - 1.5:1 - 1.5; The solvent for the reaction is N,N-diisopropylethylamine; The temperature of the reaction is 120 - 140 °C, and the time is 18 - 30 hours; The reaction is carried out under a nitrogen atmosphere.

6. The preparation method of the N-heterocyclic carbene palladium complex according to claim 2, wherein, In S3, the dosage ratio of the methoxy-substituted aminoimine compound to acetic anhydride and hydrochloric acid is 1 mmol:1.8 - 2.4 mL:1.2 - 1.8 mL; The solvent for the reaction is toluene; The temperature of the reaction is 100 - 120 °C, and the time is 40 - 55 hours.

7. The preparation method of the N-heterocyclic carbene palladium complex according to claim 2, characterized in that, In S4, the molar ratio of the methoxy-substituted aminoimine salt to 3-chloropyridine and palladium chloride is 1:4 - 8:1; The solvent for the reaction is acetone; The temperature of the reaction is 50 - 70 °C, and the time is 6 - 10 hours; The reaction is carried out under the action of a base, and the base is potassium carbonate.

8. Application of the N-heterocyclic carbene palladium complex according to claim 1 or the N-heterocyclic carbene palladium complex prepared by the preparation method of the N-heterocyclic carbene palladium complex according to any one of claims 2 - 7 in the catalytic Sonogashira coupling polymerization reaction.

9. Use of the N-heterocyclic carbene palladium complex according to claim 1 or the N-heterocyclic carbene palladium complex prepared by the preparation method of the N-heterocyclic carbene palladium complex according to any one of claims 2-7 in the reaction of 3,5-dichloropyridine with 9,9-dioctylfluorene substituted by hydroxyl Reaction.

10. A 9,9-dioctylfluorene copolymer, characterized in that, The structural formula of the 9,9-dioctylfluorene copolymer is shown in Formula (II): Formula (II) Wherein, the number average molecular weight of the 9,9-dioctylfluorene copolymer is 8 - 16.5 KDa, and the PDI is 2 - 2.5.

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