Long chain alkyl polyaromatic amine, its preparation method and application

Abstract

The application discloses long-chain alkyl polyaromatic amine, a preparation method and application thereof, and a structural formula of the long-chain alkyl polyaromatic amine is shown as formula (I): formula (I); wherein R is alkyl with 5-12 carbon atoms, the weight average molecular weight is 5000-136000 g / mol, and the PDI is 1.41-2.24; the long-chain alkyl polyaromatic amine provided by the application has high fluorescence intensity, can stably emit fluorescence under high temperature and long-term light irradiation, and has a long fluorescence lifetime.

Description

TECHNICAL FIELD

[0001] The application belongs to the technical field of organic polymer, and particularly relates to a long-chain alkyl polyaromatic amine as well as a preparation method and application thereof. BACKGROUND

[0002] The fluorescent material refers to a kind of material that can convert incident light to generate converted light with predetermined wavelength, and is widely used in display, light conversion film and lighting field.

[0003] The fluorescent material refers to a kind of material that can emit wavelength light after absorbing photon excitation, in particular, refers to a kind of material that can absorb ultraviolet light below 400 nanometers and emit visible light with wavelength of 400-650 nanometers. In recent years, with the continuous innovation and development of new energy technology, the polymer fluorescent material can be used in fluorescent concentrated solar cell, used for improving the photoelectric conversion efficiency of solar module, and improving the service life of photovoltaic module by absorbing ultraviolet rays.

[0004] However, the solar cell usually needs to be prepared at a high temperature, or needs to be used under long-term light irradiation, and under high temperature or long-term light irradiation, the fluorescent lifetime of the fluorescent material is reduced. Therefore, it is an urgent problem to provide a material that can stably emit fluorescent light under high temperature and long-term light irradiation. SUMMARY

[0005] In view of the deficiencies in the prior art, the application provides a long-chain alkyl polyaromatic amine, which has high fluorescent intensity and can stably emit fluorescent light under high temperature and long-term light irradiation, and has a long fluorescent lifetime.

[0006] The application aims to provide a long-chain alkyl polyaromatic amine, and the structural formula of the long-chain alkyl polyaromatic amine is shown as formula (I): Formula (I);

[0007] In the formula, R is an alkyl group with carbon atom number of 5-12, the weight average molecular weight is 5000-136000 g / mol, and the PDI is 1.41-2.24.

[0008] In some embodiments of the application, the R is a pentyl group, a hexyl group, an octyl group or a dodecyl group.

[0009] In some embodiments of the application, the structural formula of the long-chain alkyl polyaromatic amine is shown as formula (II): Formula (II);

[0010] In the formula, the weight average molecular weight is 5000-136000 g / mol, and the PDI is 1.41-2.02.

[0011] In some embodiments of the present application, the long-chain alkyl polyarylamine has a structural formula as shown in formula (III): Formula (III);

[0012] wherein the weight average molecular weight is 92117 g / mol and the PDI is 2.24.

[0013] In some embodiments of the present application, the long-chain alkyl polyarylamine has a structural formula as shown in formula (IV): Formula (V);

[0014] wherein the weight average molecular weight is 35817 g / mol and the PDI is 1.54.

[0015] Another object of the present application is to provide a preparation method of the long-chain alkyl polyarylamine, comprising the following steps: reacting an alkyl-substituted aniline and 4, 4'-dibromobiphenyl under the action of a palladium catalyst and an auxiliary agent to obtain the long-chain alkyl polyarylamine.

[0016] In some embodiments of the present application, the palladium catalyst has a structure as shown in formula (VI): Formula (VI);

[0017] wherein R1 and R2 are independently hydrogen, methyl, ethyl or isopropyl, and R1 and R2 are not hydrogen at the same time.

[0018] In some embodiments of the present application, the auxiliary agent comprises an organic base and a solvent.

[0019] In some embodiments of the present application, the molar ratio of the alkyl-substituted aniline to 4, 4'-dibromobiphenyl is 1:1.

[0020] In some embodiments of the present application, the molar ratio of the palladium catalyst to 4, 4'-dibromobiphenyl is 0.005-0.02:1.

[0021] In some embodiments of the present application, the reaction temperature is 100-120°C and the reaction time is 12-36 hours.

[0022] In some embodiments of the present application, the reaction further comprises a post-processing step after the reaction.

[0023] In some embodiments of the present application, the molar ratio of 4, 4'-dibromobiphenyl to the organic base is 1:2-4.

[0024] In some embodiments of the present application, the organic base is potassium tert-butoxide.

[0025] In some embodiments of the present application, the solvent is toluene.

[0026] Compared with the prior art, the present application has the following beneficial effects:

[0027] (1) Pure solid poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (i.e. PTAA) may be too close to the benzene ring, and thus aggregation-induced quenching (i.e. ACQ effect) occurs, resulting in very weak fluorescence intensity. In the present application, long-chain alkyl is introduced into the side chain of polyarylamine, and due to the steric effect of long-chain alkyl, the polyarylamine forms a non-planar structure, reduces the intermolecular interaction, and inhibits the generation of excimer, so that the AIE property (i.e. exhibiting stronger fluorescence in the aggregated state) can be exhibited, and the fluorescence intensity is enhanced.

[0028] (2) The long-chain alkyl polyarylamine of the present application can stably emit fluorescence under high temperature and long-term light irradiation, and has a long fluorescence lifetime.

[0029] (3) Compared with long-chain alkyl polyarylamine substituted with pentyl, hexyl or octyl, long-chain alkyl polyarylamine substituted with dodecyl not only has high fluorescence intensity, but also has higher stability. BRIEF DESCRIPTION OF DRAWINGS

[0030] Figure 1 NMR hydrogen spectrum of long-chain alkyl polyarylamine prepared for Example 1.

[0031] Figure 2 NMR hydrogen spectrum of long-chain alkyl polyarylamine prepared for Example 2.

[0032] Figure 3 NMR hydrogen spectrum of long-chain alkyl polyarylamine prepared for Example 3.

[0033] Figure 4 NMR hydrogen spectrum of long-chain alkyl polyarylamine prepared for Example 4. DETAILED DESCRIPTION

[0034] In order for those skilled in the art to better understand the technical solutions in the present application, the technical solutions of the present application will be described clearly and completely below in combination with the embodiments of the present application. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative labor should belong to the scope of protection of the present application.

[0035] All raw materials of the present application can be obtained through commercial channels.

[0036] t -BuOK is potassium tert-butoxide;

[0037] The structure of the imidazole salt ligand L1 is as follows: ;

[0038] The structure of imidazolium salt ligand L2 is shown below: ;

[0039] The structure of imidazolium salt ligand L3 is shown below: ;

[0040] The structure of imidazolium salt ligand L4 is shown below: .

[0041] Example 1

[0042] This example provides a palladium catalyst C1, the method of preparation thereof comprising the following steps:

[0043] Imidazolium salt ligand L1 (1.0 mmol), potassium carbonate (10 mmol) and palladium dichloride (1.0 mmol) were added to 10 mL of N-methylimidazole, mixed at room temperature, then the mixture was heated to 80 °C and stirred for 12 hours, after the end of the reaction, the liquid was removed under reduced pressure, the crude product was dissolved in 5 mL of dichloromethane, then 20 mL of n-hexane were added, the palladium complex precipitate was collected by filtration and washed with n-hexane (2 x 20 mL), dried, obtaining a palladium catalyst powder C1 in off-white color, with a yield of 81 %; the nuclear magnetic resonance spectrum of palladium catalyst C1 is as follows:

[0044] 1 H NMR (400 MHz, CDCl3) δ 7.50 (td, J = 1.6, 0.8 Hz, 1H), 7.12-7.07(m, 5H), 7.00 (dd, J = 5.6, 1.7 Hz, 1H), 6.85-6.81 (m, 4H), 6.60 (s, 4H),3.82 (s, 6H), 3.72 (d, J = 0.6 Hz, 3H), 2.31 (s, 12H), 2.26 (d, J = 0.7 Hz,6H).

[0045] 13 C NMR (101 MHz, CDCl3) δ 162.02, 156.48, 133.58, 133.45, 133.24,130.79, 130.15, 129.44, 127.53, 122.13, 116.03, 103.07, 62.77, 55.35, 35.03,21.03, 18.14.

[0046] The structure of palladium catalyst C1 is shown below:

[0047] Example 2

[0048] This example provides a palladium catalyst C2, the method of preparation of which comprises the following steps:

[0049] Imidazolium salt ligand L2 (1.0 mmol), potassium carbonate (8 mmol) and palladium dichloride (1.0 mmol) were added to 8 mL of N-methylimidazole, mixed at room temperature, then the mixture was heated to 70°C and stirred for 16 hours, after the end of the reaction, the liquid was removed under reduced pressure, the crude product was dissolved in 5 mL of dichloromethane, then 20 mL of n-hexane were added, the palladium complex precipitate was collected by filtration and washed with n-hexane (2 x 20 mL), dried, obtaining a greyish white powder of palladium catalyst C2 with a yield of 76%; the nuclear magnetic resonance carbon hydrogen spectrum of palladium catalyst C2 is as follows:

[0050] 1 H NMR (400 MHz, CDCl3) δ 7.50 (tt, J = 1.4, 0.7 Hz, 1H), 7.13-7.08(m, 5H), 7.00 (dd, J = 5.6, 1.7 Hz, 1H), 6.87-6.80 (m, 8H), 6.79-6.73 (m,2H), 3.82 (s, 6H), 3.72 (t, J = 0.7 Hz, 3H), 2.50 (qd, J = 7.5, 0.9 Hz, 8H),1.26 (t, J = 7.5 Hz, 12H).

[0051] 13 C NMR (101 MHz, CDCl3) δ 162.02, 156.48, 141.57, 136.09, 130.79,129.44, 128.76, 127.53, 127.01, 122.13, 116.03, 103.07, 62.77, 55.35, 35.03,24.15, 14.23.

[0052] The structure of palladium catalyst C2 is shown below: .

[0053] Example 3

[0054] This example provides a palladium catalyst C3, the method of preparation of which comprises the following steps:

[0055] Imidazole salt ligand L3 (1.0 mmol), potassium carbonate (12 mmol) and palladium dichloride (1.0 mmol) were added to 12 mL of N-methylimidazole, mixed at room temperature, then the mixture was heated at 90 °C and stirred for 10 hours, after the reaction was completed, the liquid was removed under reduced pressure, the crude product was dissolved in 5 mL of dichloromethane, then 20 mL of n-hexane was added, the obtained palladium complex was precipitated by filtration and washed with n-hexane (2 x 20 mL), dried to obtain a grayish white palladium catalyst powder C3 with a yield of 74%; the nuclear magnetic carbon hydrogen spectrum of palladium catalyst C3 is as follows:

[0056] 1 H NMR (400 MHz, CDCl3) δ 7.50 (tt, J = 1.5, 0.7 Hz, 1H), 7.12-7.08(m, 5H), 7.00 (dd, J = 5.6, 1.7 Hz, 1H), 6.94-6.90 (m, 4H), 6.85-6.81 (m,4H), 6.76 (dd, J = 8.8, 7.7 Hz, 2H), 3.82 (s, 6H), 3.72 (t, J = 0.7 Hz, 3H),2.89 (hd, J = 6.8, 0.7 Hz, 4H), 1.28 (d, J = 6.9 Hz, 24H).

[0057] 13 C NMR (101 MHz, CDCl3) δ 162.02, 156.48, 144.25, 141.09, 130.79,129.44, 127.53, 127.24, 126.60, 122.13, 116.03, 103.07, 62.77, 55.35, 35.03,28.88, 24.04.

[0058] The structure of palladium catalyst C3 is as follows: .

[0059] Example 4

[0060] The present embodiment provides a long-chain alkyl polyarylamine, and a preparation method thereof, which comprises the following steps:

[0061] 4-pentyl aniline (0.5 mmol), 4, 4'-dibromobiphenyl (0.5 mmol), palladium catalyst C1 (0.01 mmol), potassium carbonate (0.5 mmol) and N-methylimidazole (5 mL) were added to a three-necked flask, mixed at room temperature, then the mixture was heated at 90 °C and stirred for 10 hours, after the reaction was completed, the liquid was removed under reduced pressure, the crude product was dissolved in 5 mL of dichloromethane, then 20 mL of n-hexane was added, the obtained palladium complex was precipitated by filtration and washed with n-hexane (2 x 20 mL), dried to obtain a grayish white palladium catalyst powder C4 with a yield of 74%; the nuclear magnetic carbon hydrogen spectrum of palladium catalyst C4 is as follows: tBuok (1.5 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 110 °C and stirred for 24 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 73.6%. The weight-average molecular weight (Mw) was 35817 g / mol, and the molecular weight distribution index (PDI) was 1.54. The structure of the long-chain alkyl polyarylamine is shown below:

[0062] .

[0063] Example 5

[0064] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0065] 4-Hexylaniline (0.5 mmol), 4,4'-dibromobiphenyl (0.5 mmol), palladium catalyst C2 (0.01 mmol), t Buok (1.5 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 110 °C and stirred for 24 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 76.6%. The weight-average molecular weight (Mw) was 34415 g / mol, and the molecular weight distribution index (PDI) was 2.08. The structure of the long-chain alkyl polyarylamine is shown below:

[0066] .

[0067] Example 6

[0068] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0069] 4-Octoaniline (1 mmol), 4,4'-dibromobiphenyl (1 mmol), palladium catalyst C1 (0.01 mmol), t-BuOK (3 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 110 °C and stirred for 24 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 65.4%. The weight-average molecular weight (Mw) was 92117 g / mol, and the molecular weight distribution index (PDI) was 2.24. The structure of the long-chain alkyl polyarylamine is shown below:

[0070] .

[0071] Example 7

[0072] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0073] 4-Dodecylaniline (1 mmol), 4,4'-dibromobiphenyl (1 mmol), palladium catalyst C3 (0.01 mmol), t -BuOK (3 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 110 °C and stirred for 24 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 57.4%. The weight-average molecular weight (Mw) was 135241 g / mol, and the molecular weight distribution index (PDI) was 1.69. The structure of the long-chain alkyl polyarylamine is shown below:

[0074] .

[0075] Example 8

[0076] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0077] 4-Dodecylaniline (1 mmol), 4,4'-dibromobiphenyl (1 mmol), palladium catalyst C2 (0.02 mmol), t-BuOK (2 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 100 °C and stirred for 36 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 62.3%. The weight-average molecular weight (Mw) was 33524 g / mol, and the molecular weight distribution index (PDI) was 2.02. The structure of the long-chain alkyl polyarylamine is shown below:

[0078] .

[0079] Example 9

[0080] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0081] 4-Dodecylaniline (1 mmol), 4,4'-dibromobiphenyl (1 mmol), palladium catalyst C1 (0.005 mmol), t -BuOK (4 mmol) was added to a 20 mL reaction tube, followed by 1.5 mL of toluene. The mixture was heated to 120 °C and stirred for 36 h under nitrogen protection. After cooling to room temperature, a grayish-black liquid was obtained. The mixture was settled in 50 mL of methanol, precipitating a gray solid. The solid was filtered, dried, and the mixture was added to a 20 mL reaction tube. The mixture was then filtered again, and the filtrate was collected and washed in 50 mL of methanol. The washing process was repeated twice, followed by filtration and drying to obtain a pale yellow solid with a yield of 71.8%. The weight-average molecular weight (Mw) was 25697 g / mol, and the molecular weight distribution index (PDI) was 1.91. The structure of the long-chain alkyl polyarylamine is shown below:

[0082] .

[0083] Example 10

[0084] This embodiment provides a long-chain alkyl polyarylamine, the preparation method of which includes the following steps:

[0085] 4-Dodecylaniline (0.05 mmol), 4,4'-dibromobiphenyl (0.05 mmol), palladium catalyst C3 (0.015 mmol), tBuOK (2.5 mmol) was added into a 20 mL reaction tube, 1.5 mL of toluene was added, the temperature was raised to 115 °C under the protection of nitrogen, stirring for 30 h, and then cooled to room temperature to obtain a gray-black liquid. The mixture was settled in 50 mL of methanol to precipitate a gray solid, which was filtered and dried. The mixture was added into a 20 mL reaction tube, and then filtered under suction. The filtrate was collected and washed by settling in 50 mL of methanol under suction. The filtration under suction was repeated twice, and then dried to obtain a light yellow solid with a yield of 59.6 %, a weight average molecular weight Mw of 11531 g / mol, and a molecular weight distribution index PDI of 1.41. The structure of the long-chain alkyl polyarylamine is as follows:

[0086] .

[0087] Example 11

[0088] The present example provides a long-chain alkyl polyarylamine, and a preparation method thereof includes the following steps:

[0089] 4-dodecylaniline (0.5 mmol), 4, 4'-dibromobiphenyl (0.5 mmol), palladium catalyst C1 (0.008 mmol), 2, 2'-bipyridine (0.01 mmol), and 1, 4-dioxane (2 mL) were added into a 20 mL reaction tube, and then filtered under suction. The filtrate was collected and washed by settling in 50 mL of methanol under suction. The filtration under suction was repeated twice, and then dried to obtain a light yellow solid with a yield of 59.6 %, a weight average molecular weight Mw of 11531 g / mol, and a molecular weight distribution index PDI of 1.41. The structure of the long-chain alkyl polyarylamine is as follows: t BuOK (3.5 mmol) was added into a 20 mL reaction tube, 1.5 mL of toluene was added, the temperature was raised to 105 °C under the protection of nitrogen, stirring for 18 h, and then cooled to room temperature to obtain a gray-black liquid. The mixture was settled in 50 mL of methanol to precipitate a gray solid, which was filtered and dried. The mixture was added into a 20 mL reaction tube, and then filtered under suction. The filtrate was collected and washed by settling in 50 mL of methanol under suction. The filtration under suction was repeated twice, and then dried to obtain a light yellow solid with a yield of 53.8 %, a weight average molecular weight Mw of 5067 g / mol, and a molecular weight distribution index PDI of 1.86. The structure of the long-chain alkyl polyarylamine is as follows:

[0090] .

[0091] Comparative Example 1

[0092] The present comparative example provides a poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (i.e., PTAA), and a preparation method thereof includes the following steps:

[0093] 2, 4, 6-trimethylaniline (0.5 mmol), 4, 4'-dibromobiphenyl (0.5 mmol), palladium catalyst C1 (0.01 mmol), 2, 2'-bipyridine (0.01 mmol), and 1, 4-dioxane (2 mL) were added into a 20 mL reaction tube, and then filtered under suction. The filtrate was collected and washed by settling in 50 mL of methanol under suction. The filtration under suction was repeated twice, and then dried to obtain a light yellow solid with a yield of 59.6 %, a weight average molecular weight Mw of 11531 g / mol, and a molecular weight distribution index PDI of 1.41. The structure of the long-chain alkyl polyarylamine is as follows: t-BuOK (1.5 mmol) was added into a 20 mL reaction tube, 1.5 mL of toluene was added, the temperature was raised to 110 ℃ under the protection of nitrogen, and stirred for 24 h, and then cooled to room temperature to obtain a gray-black liquid. The mixture was settled in 50 mL of methanol, and a gray solid was precipitated. The mixture was filtered and dried. The mixture was added into a 20 mL reaction tube, and filtered under suction. The filtrate was collected and settled in 50 mL of methanol for washing. The mixture was filtered under suction, and the washing was repeated twice. The mixture was filtered under suction and dried to obtain a light yellow solid, with a yield of 74.1 %, a weight average molecular weight Mw of 35817 g / mol, and a molecular weight distribution index PDI of 1.64. The structure of the long-chain alkyl polyarylamine is as follows:

[0094] .

[0095] The long-chain alkyl polyarylamines of Examples 5-11 and Comparative Example 1 were subjected to fluorescence tests, and the results are shown in Table 1.

[0096] Table 1. Fluorescence properties of the long-chain alkyl polyarylamines of Examples 4-11 and Comparative Example 1.

[0097]

[0098] As can be seen from Table 1, the long-chain alkyl polyarylamines prepared in Examples 4-11 have strong fluorescence intensity.

[0099] The long-chain alkyl polyarylamines of Examples 4-11 and Comparative Example 1 were respectively stored under light at 100 ℃ in air for 10 days. The fluorescence intensity of the long-chain alkyl polyarylamines after 10 days was tested, and the results are shown in Table 2.

[0100] Table 2. Fluorescence properties of the long-chain alkyl polyarylamines of Examples 4-11 and Comparative Example 1.

[0101]

[0102] As can be seen from Table 2, the long-chain alkyl polyarylamines prepared in Examples 7-11 can stably emit fluorescence under high temperature and long-term light, and have a long fluorescence lifetime.

[0103] Finally, it should be noted that the above examples are only used to illustrate the technical solutions of the present application, and not to limit them. Although the present application has been described in detail with reference to the above examples, those skilled in the art should understand that the specific embodiments of the present application can be modified or replaced by equivalents after reading the present application. However, these modifications or changes do not deviate from the scope of the present application.

Claims

1. A long chain alkyl polyaromatic amine characterized in that, The long-chain alkyl polyarylamine has a structural formula as shown in formula (II). Formula (II); The weight average molecular weight is 5000-136000 g / mol, and the PDI is 1.41-2.

02.

2. The process for the preparation of long chain alkyl polyaromatic amines as claimed in claim 1, wherein, The method comprises the following steps: The long-chain alkyl polyarylamine is obtained by reacting 4-dodecyl aniline and 4, 4'-dibromobiphenyl under the action of a palladium catalyst and an auxiliary agent.

3. The method of preparing long chain alkyl polyaryl amines according to claim 2, characterized in that, The structure of the palladium catalyst is shown in formula (VI): Formula (VI); R1 and R2 are independently hydrogen, methyl, ethyl or isopropyl, and R1 and R2 are not hydrogen at the same time. The auxiliary agent comprises an organic base and a solvent.

4. The method of claim 2, wherein the long chain alkyl polyaromatic amine is prepared by the reaction of a long chain alkyl polyamine and a dihaloaromatic compound in the presence of a base. The molar ratio of the 4-dodecyl aniline to the 4, 4'-dibromobiphenyl is 1:

1.

5. The method of claim 2, wherein the long chain alkyl polyaromatic amine is prepared by the reaction of a long chain alkyl polyamine and a dihaloaromatic compound in the presence of a base. The molar ratio of the palladium catalyst to the 4, 4'-dibromobiphenyl is 0.005-0.02:

1.

6. The method of claim 2, wherein the long chain alkyl polyaromatic amine is prepared by the reaction of a long chain alkyl polyamine with a polyaromatic amine in the presence of a base. The temperature of the reaction is 100-120 DEG C, and the time is 12-36 hours.

7. The method of claim 2, wherein the long chain alkyl polyaromatic amine is prepared by the reaction of a long chain alkyl polyamine with a polyaromatic amine in the presence of a base. The reaction further comprises a post-treatment step after the reaction.

8. The method for preparing long-chain alkyl polyarylamines according to claim 3, characterized in that, The molar ratio of the 4, 4'-dibromobiphenyl to the organic base is 1:2-4.

9. The method of claim 3, wherein the long chain alkyl polyaromatic amine is prepared by the reaction of a long chain alkyl polyamine and a dihaloaromatic compound in the presence of a base. The organic base is potassium tert-butoxide.

10. The method for preparing long-chain alkyl polyarylamines according to claim 3, characterized in that, The solvent is toluene.

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