Compound with biquinoline-like structure as well as preparation method and application of compound

Abstract

The invention provides a compound with a biquinoline-like structure as well as a preparation method and application thereof, the compound with the biquinoline-like structure has a structure as shown in a formula I or a formula II, and the compound with the biquinoline-like structure has a relatively large conjugate area, so that delocalization of electrons is facilitated, and meanwhile, the charge transfer performance is improved. The fluorescent light of the molecules is 400 nm, and the molecules are suitable for display illumination or short-wave lasers. Especially, emission of blue light (about 400nm) is crucial to OLED display. Blue-light pixels are one of the basis of RGB display, and preparation of efficient and stable blue-light materials is an important research direction at present. In addition, the narrow half-peak width (narrower than 50nm) shows that the molecules have excellent color purity and are very beneficial to display and illumination applications. Particularly in high-resolution displays, precise color rendition is critical.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic light-emitting materials, and particularly relates to a conjugated compound building block with a bisquinoline-like structure, a preparation method thereof, and an application thereof. Background Art

[0002] Quinoline compounds are a very important class of synthetic building blocks in the field of materials science. Due to their relatively high electron cloud density, they can form complexes with metal ions, bind hydrogen ions, and, with their unique optical properties, such compounds exhibit broad application potential in multiple fields such as corrosion protection, sensor technology, the development of nonlinear optical materials, and the fine tuning of the structure of electronic materials. In terms of synthetic routes, quinoline compounds usually rely on reactions such as the Skraup-Doebner-Von Miller reaction (Denmark, Scott E., and Srikanth Venkatraman. "On the mechanism of the Skraup-Doebner-Von Miller quinoline synthesis." The Journal of Organic Chemistry 71.4 (2006): 1668-1676.), the Combes reaction (He, Yafen, Wei Zhang, and Jinbo Hu. "Concise synthesis of 2,4-bis(fluoroalkyl)quinoline derivatives from arylamines." Tetrahedron 162 (2024): 1340467.), the Conrad–Limpach-Knorr reaction (MISANI, FERNANDA, and MARSTON TAYLOR BOGERT. "The search for superior drugs for tropical diseases. II. Synthetic studies in the quinoline and phenanthroline series. Skraup and Conrad-Limpach-Knorr reactions." The Journal of Organic Chemistry 10.4 (1945): 347-365.), the Povarov reaction (de Paiva, Walysson Ferreira, et al. "The Povarov reaction: A versatile method to synthesize tetrahydroquinolines, quinolines and julolidines." Synthesis 54.14 (2022): 3162-3179.), and Wu, Jiahao, et al."Palladium-catalyzed cascade of aza-Wacker and Povarov reactions of arylamines and 1,6-dienes for hexahydro-cyclopenta[b]quinoline framework." Nature Communications 15.1 (2024): 6776.) and a series of classic methods such as the Gould–Jacobs reaction (Gould, R. Gordon, and Walter A. Jacobs. "The synthesis of certain substituted quinolines and 5,6-benzoquinolines." Journal of the American Chemical Society 61.10 (1939): 2890-2895.). However, these synthetic strategies usually involve complex multi-step reaction processes and generally require relatively harsh reaction conditions, such as the use of high temperatures, strong acids, or strong bases. This undoubtedly increases the difficulty and cost of synthesis. More critically, it is difficult to effectively obtain quinoline compounds with fused ring structures through these traditional methods, and this limitation has largely restricted the research and application expansion of quinoline compounds.

[0003] The Pictet-Spengler reaction is commonly used in biochemistry to prepare quinoline alkaloids. The reaction mechanism involves the condensation of β-arylethylamine with ketones or aldehydes followed by ring closure to prepare the nitrogen heterocyclic compound skeleton ( Joachim, et al. "The Pictet–Spengler reaction in nature and in organic chemistry." Angewandte Chemie International Edition 50.37 (2011): 8538-8564.). However, although it is widely used in organic synthesis, the research on expanding this reaction strategy to construct nitrogen heterocyclic compounds with large conjugated structures is relatively limited, and this field remains to be explored in depth. Summary of the Invention

[0004] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a compound with a bisquinoline-like structure, its preparation method, and applications.

[0005] To achieve the purpose of the present invention, the following technical solutions are adopted:

[0006] On the one hand, the present invention provides a compound with a bisquinoline-like structure, and the compound with the bisquinoline-like structure has a structure shown in the following formula I or formula II:

[0007]

[0008] Wherein ring Ar1 and ring Ar2 are each independently selected from any one of a substituted or unsubstituted C4-C10 heteroaromatic ring and a substituted or unsubstituted C4-C10 heteroaromatic ring;

[0009] The substituents of the substituted ring Ar1 and ring Ar2 are each independently selected from any one of hydrogen, halogen, nitro, and C1-C12 straight-chain or branched-chain alkyl;

[0010] R1 is each independently selected from any one of hydrogen and C1-C12 straight-chain or branched-chain alkyl;

[0011] X1 and X2 are each independently selected from any one of O, S, and Se.

[0012] Preferably, ring Ar1 is selected from any one of the following groups:

[0013]

[0014] Wherein, represents the connection site of the group; R2, R3, and R4 are each independently selected from any one of hydrogen, halogen, nitro, C1-C12 straight-chain or branched-chain alkyl, halogen-substituted C1-C12 straight-chain or branched-chain alkyl, and C1-C12 alkoxy.

[0015] Preferably, ring Ar2 is selected from any one of the following groups:

[0016]

[0017] Wherein, the dotted line represents the fused bond of the ring; R5, R6, R7, and R8 are each independently selected from any one of hydrogen, halogen, nitro, and C1-C12 straight-chain or branched-chain alkyl.

[0018] More preferably, ring Ar1 is selected from phenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,5-dimethylphenyl, or thiophenyl.

[0019] More preferably, ring Ar2 is selected from a benzene ring or a benzene ring substituted with a methyl group.

[0020] Preferably, R1 is selected from hydrogen, methyl, n-pentyl, or 2-methyl-propyl.

[0021] Preferably, the compound with the bisquinoline-like structure is any one of the following compounds 1-10:

[0022]

[0023] On the other hand, the present invention provides a method for preparing a compound having a bisquinoline-like structure as described above, and the preparation method includes the following steps:

[0024] (1) The compound shown in Formula II reacts with the compound shown in Formula III to obtain the compound shown in Formula IV, and the reaction formula is as follows:

[0025]

[0026] (2) The compound shown in Formula IV obtained in step (1) reacts with an aldehyde to obtain a conjugated compound having a bisquinoline structure shown in Formula I, and the reaction formula is as follows:

[0027]

[0028] The molar ratio of the compound shown in Formula II to the compound shown in Formula III in step (1) is 1:2 - 4, such as 1:2, 1:2.3, 1:2.5, 1:2.8, 1:3, 1:3.5, 1:3.8 or 1:4.

[0029] Preferably, the temperature of the reaction in step (1) is 50 - 80 °C, such as 50 °C, 55 °C, 60 °C, 65 °C, 70 °C, 75 °C or 80 °C.

[0030] Preferably, the reaction time in step (1) is 15 - 72 h, such as 15 h, 18 h, 20 h, 24 h, 28 h, 30 h, 36 h, 40 h, 42 h, 48 h, 50 h, 55 h, 58 h, 64 h, 68 h, 70 h or 72 h.

[0031] Preferably, the reaction in step (1) is carried out in a solvent.

[0032] Preferably, the solvent in step (1) includes tetrahydrofuran or diethyl ether.

[0033] Preferably, the reaction in step (1) is carried out under the catalysis of a catalyst, and the catalyst is preferably tetrakis(triphenylphosphine)palladium.

[0034] Preferably, the reaction in step (1) is carried out in the presence of a basic substance, and the basic substance is selected from any one or a combination of at least two of potassium carbonate, sodium carbonate, cesium carbonate or potassium acetate.

[0035] Preferably, the molar ratio of the compound shown in Formula IV to the aldehyde shown in Formula V in step (2) is 1:2 - 4, such as 1:2, 1:2.3, 1:2.5, 1:2.8, 1:3, 1:3.5, 1:3.8 or 1:4.

[0036] Preferably, the temperature of the reaction in step (2) is 80 to 180 °C, such as 80 °C, 100 °C, 120 °C, 140 °C, 150 °C, 170 °C or 180 °C.

[0037] Preferably, the reaction time in step (2) is 2.5 to 48 h, such as 2.5 h, 4 h, 6 h, 8 h, 10 h, 12 h, 14 h, 15 h, 18 h, 20 h, 24 h, 28 h, 30 h, 36 h, 40 h, 42 h or 48 h.

[0038] Preferably, the reaction in step (2) is carried out in a solvent.

[0039] Preferably, the solvent in step (2) includes any one or a combination of at least two of toluene, xylene or mesitylene.

[0040] Preferably, the reaction in step (2) is carried out in the presence of an acidic substance.

[0041] Preferably, the acidic substance includes inorganic acids, organic carboxylic acids, Lewis acids or other acidic substances.

[0042] Preferably, the inorganic acid is hydrochloric acid or sulfuric acid.

[0043] Preferably, the organic carboxylic acid is any one or a combination of at least two of acetic acid, trifluoroacetic acid, p-toluenesulfonic acid or trifluoromethanesulfonic acid.

[0044] Preferably, the Lewis acid is boron trifluoride, iodine or gold(III) chloride.

[0045] Preferably, the other acidic substance is cyanuric chloride.

[0046] Preferably, the reaction in step (2) can be achieved using an ordinary reactor or a microwave reactor.

[0047] On the other hand, the present invention provides the use of the compound of the bisquinoline-like structure as described above as an organic light-emitting material.

[0048] Compared with the prior art, the present invention has the following beneficial effects:

[0049] The compounds with a bisquinoline-like structure of the present invention have a large conjugated area, which is beneficial to the delocalization of electrons and simultaneously improves the charge transport performance. The fluorescence emission of such molecules is at 400 nm, which is suitable for applications in display lighting or short-wave lasers. In particular, blue light emission (around 400 nm) is crucial for OLED displays. Blue pixels are one of the bases of RGB displays, and preparing efficient and stable blue light materials is an important research direction at present. In addition, the narrow full width at half maximum (narrower than 50 nm) indicates that the molecules have excellent color purity, which is very beneficial for display and lighting applications. Especially in high-resolution displays, accurate color reproduction is the key. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 is the UV-visible spectrum of Compounds 1-10;

[0051] Figure 2 is the fluorescence spectrum of Compounds 1-10. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0052] The technical solutions of the present invention will be further described below through specific embodiments. Those skilled in the art should understand that the embodiments are only for helping to understand the present invention and should not be construed as specific limitations on the present invention.

[0053] Example 1

[0054] A conjugated compound 1 with a bisquinoline structure is as follows:

[0055]

[0056] Its preparation method includes the following steps:

[0057] (1)

[0058] Weigh Compound ① (100 mg, 0.34 mmol, 1 eq) and Compound ② (161.68 mg, 0.74 mmol, 2.2 eq) into a pressure tube, and add THF (3 ml) to dissolve. Then add K2CO3 (5.1 ml, 3.36 mmol, 15 eq), and purge with argon for 20 minutes. Add Pd2(PPh3)4 (40 mg, 0.004 mmol, 0.05 eq), and then purge with argon for 20 minutes. The reaction is carried out at 80 °C for 2 days. Add water to quench the reaction. Wash the resulting mixture with DCM (5 ml x 3). Then wash the organic layer with brine, dry over Na2SO4 and concentrate in vacuo. Precipitate from methanol and dichloromethane to obtain a yellow solid (100 mg), yield: 94%. 11H NMR (600 MHz, CDCl3): δ 7.38 (s, 2H), 7.33 (dd, J = 7.6, 1.4 Hz, 2H), 7.22–7.14 (td, J = 8.0, 1.4 Hz, 2H), 6.87–6.77 (m, 4H), 4.10 (s, 4H). 13 13C NMR (151 MHz, CDCl3): δ 144.23, 142.48, 139.18, 131.00, 129.42, 120.12, 118.67, 118.28, 116.00. Mass spectrum: (Q-TOF): Calcd for C 18 H 14 N2S2 m / z = 323.06 [M+H] + , found 323.06 [M+H] + .

[0059] (2)

[0060] Compound ③ (50 mg, 0.155 mmol, 1 eq) and benzaldehyde (0.1 ml) were weighed and placed in a pressure tube, and dissolved in toluene (2.5 ml). Then TFA (1 drop) was added. The reaction was carried out at 130 °C for 2 days. Sodium carbonate solution was added to quench the reaction and neutralize TFA. The resulting mixture was washed with DCM (5 ml x 3). Then the organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. A yellow solid compound ⑤ (i.e., compound 1, 32.5 mg, yield: 42.8%) was obtained by precipitation from methanol and dichloromethane. 1 1H NMR (600 MHz, CDCl3, TFA): δ (ppm): 8.45 (d, J = 8.6 Hz, 2H), 8.30 (d, J = 8.2 Hz, 2H), 8.15 (t, J = 7.7 Hz, 2H), 8.07–7.95 (m, 4H), 7.95–7.84 (m, 8H). 13 13C NMR (151 MHz, CDCl3, TFA): δ (ppm): 156.86, 151.81, 136.20, 134.99, 134.27, 134.10, 131.46, 130.59, 128.76, 128.68, 124.12, 123.82, 123.48, 122.39. Mass spectrum: (Q-TOF): Calcd for C 32 H 18 N2S2 m / z = 495.09 [M+H] + , found 495.09 [M+H] + 。

[0061] Compound 2-10 was synthesized by the same experimental procedure, except that different starting materials were selected according to the structure of the compound. The structural characterization data of the synthesized compounds are as follows:

[0062] Compound 2: Yellow solid (58.9 mg, yield: 62.6%). 1 1H NMR (600 MHz, CDCl3, TFA): δ 8.43 (dd, J = 8.4 Hz, 0.6 Hz, 2H), 8.26 (dd, J = 8.4, 0.6 Hz, 2H), 8.14 (t, J = 7.2 Hz, 2H), 8.02 (t, J = 7.2 Hz, 2H), 7.90 (d, J = 8.4 Hz, 4H), 7.87 (d, J = 8.4 Hz, 4H), 1.53 (s, 18H). 13 13C NMR (151 MHz, CDCl3, TFA): δ 159.10, 156.88, 152.23, 136.38, 135.01, 134.17, 131.40, 128.71, 127.75, 125.84, 124.14, 123.85, 123.39, 122.28, 35.73, 31.05. Mass spectrum: (Q-TOF): Calculated for C 40 H 34 N2S2 m / z = 607.22 [M + H] + , found 607.22 [M + H] + .

[0063] Compound 3: Yellow solid (61.5 mg, yield: 62.8%). 1 1H NMR (600 MHz, CDCl3, TFA): δ 8.42 (d, J = 8.5 Hz, 2H), 8.38 (dd, J = 8.4, 1.2 Hz, 2H), 8.22 (td, J = 7.7, 1.2 Hz, 2H), 8.18 (d, J = 8.0 Hz, 4H), 8.12 (t, J = 7.7 Hz, 2H), 8.09 (d, J = 8.0 Hz, 4H). 13 13C NMR (151 MHz, CDCl3, TFA): δ 157.68, 150.00, 136.27, 135.91, 135.66, 133.90, 132.18, 131.79, 129.46, 127.62, 127.59, 124.01, 123.85, 123.74, 122.06. Mass spectrum:

[0064] (Q-TOF): Calculated for C 34 H 16 F6N2S2 m / z = 631.07 [M + H] +, Test value 631.07 [M+H] + .

[0065] Compound 4: Yellow solid (35.7 mg, yield: 83.2%). 1 H NMR (600 MHz, CDCl3, TFA): δ 8.41 (d, J = 4.2 Hz, 2H), 8.36 (d, J = 4.2 Hz, 2H), 8.18 (t, J = 7.8 Hz, 2H), 8.08 (t, J = 7.8 Hz, 2H), 7.95 (dd, J = 8.4, 4.8 Hz, 4H), 7.59 (t, J = 8.4 Hz, 4H). 13 C NMR (151 MHz, CDCl3, TFA): δ 167.15, 165.43, 157.21, 150.77, 136.10, 135.32, 133.94, 131.77, 131.46, 131.40, 124.58, 124.56, 124.14, 123.91, 123.51, 122.05, 118.34, 118.19. Mass spectrum: (Q-TOF): Calculated for C 32 H 16 N2F2S2 m / z = 531.07 [M+H] + , Test value 531.09 [M+H] + .

[0066] Compound 5: Yellow solid (23.5 mg, yield: 60.8%). 1 H NMR (600 MHz, CDCl3, TFA) δ 8.40 (d, J = 8.5 Hz, 2H), 8.32 (d, J = 8.3 Hz, 2H), 8.13 (t, J = 7.7 Hz, 2H), 8.00 (t, J = 7.7 Hz, 2H), 7.91 (d, J = 8.3 Hz, 4H), 7.37 (d, J = 8.3 Hz, 4H), 4.08 (s, 6H). 13 C NMR (151 MHz, CDCl3, TFA) δ 164.55, 156.63, 151.94, 136.41, 134.92, 134.21, 131.21, 131.02, 124.20, 123.92, 123.22, 122.11, 120.62, 116.26, 56.05. Mass spectrum: (Q-TOF): Calculated for C 34 H 22 N2O2S2 m / z = 555.11 [M+H] + , Test value 555.13 [M+H] + .

[0067] Compound 6: Yellow solid (15.6 mg, yield: 18%). 1 H NMR (600 MHz, CDCl3, TFA) δ 8.50 (s, 2H), 8.30 (d, J = 8.2 Hz, 2H), 8.14 (s, 2H), 8.01 (t, J = 7.6 Hz, 2H), 7.77 (t, J = 7.6 Hz, 2H), 7.47 (d, J = 8.6 Hz, 4H), 7.42 (s, 2H), 3.96 (s, 6H). 13 C NMR (151 MHz, CDCl3, TFA) δ 160.90, 156.65, 151.62, 136.19, 134.78, 134.26, 131.84, 131.30, 129.85, 124.12, 123.76, 123.51, 122.63, 120.77, 120.13, 113.82, 55.79. Mass spectrum:

[0068] (Q-TOF): Calculated for C 34 H 22 N2O2S2 m / z = 555.11 [M+H] + , found 555.13 [M+H] + .

[0069] Compound 7: Yellow solid (17.8 mg, yield: 20.8%). 1 H NMR (600 MHz, CDCl3, TFA) δ 8.50 (d, J = 8.5 Hz, 2H), 8.27 (d, J = 8.2 Hz, 2H), 8.13 (t, J = 7.7 Hz, 2H), 8.00 (t, J = 7.7 Hz, 2H), 7.57 (s, 2H), 7.52 (s, 4H), 2.55 (s, 12H). 13 C NMR (151 MHz, CDCl3, TFA) δ 156.40, 152.32, 140.91, 136.34, 135.75, 134.67, 134.33, 131.14, 128.70, 126.43, 124.16, 123.59, 123.36, 122.64, 21.19. Mass spectrum: (Q-TOF): Calculated for C 36 H 26 N2S2 m / z = 551.15 [M+H] + , found 551.17 [M+H] + .

[0070] Compound 8: Yellow solid (72.7 mg, yield: 92.5%). 11H NMR (600 MHz, CDCl3, TFA): δ 8.43 (dd, J = 8.4 Hz, 0.6 Hz, 2H), 8.36 (dd, J = 8.4 Hz, 0.6 Hz, 2H), 8.17 (t, J = 7.2 Hz, 2H), 8.14 (dd, J = 3 Hz, 0.6 Hz, 2H), 8.05 (t, J = 7.2 Hz, 2H), 8.00 (dd, J = 3 Hz, 0.6 Hz, 2H), 7.61 (dd, J = 5.1, 3.7 Hz, 2H). 13 13C NMR (151 MHz, CDCl3, TFA): δ 156.97, 145.59, 136.38, 135.40, 135.00, 134.42, 134.33, 131.79, 129.96, 127.64, 124.69, 123.99, 123.67, 122.30. Mass spectrum: (Q-TOF): Calcd for C 28 H 14 N2S4 m / z = 507.00 [M+H] + , found 507.02 [M+H] + .

[0071] Compound 9: Yellow solid (18.6 mg, yield: 39.5%). 1 1H NMR (600 MHz, CDCl3, TFA): δ 8.39–8.32 (m, 2H), 8.08–7.96 (m, 4H), 3.85 (t, J = 8.2 Hz, 4H), 2.95 (s, 6H), 2.11–2.00 (m, 4H), 1.74–1.66 (m, 4H), 1.53–1.44 (m, 4H), 0.98 (t, J = 7.2 Hz, 6H). 13 13C NMR (151 MHz, CDCl3, TFA): δ 158.57, 156.81, 136.30, 134.66, 132.66, 131.27, 130.76, 124.15, 123.64, 122.11, 34.46, 31.91, 29.49, 22.11, 17.07, 13.38. Mass spectrum: (Q-TOF): Calcd for C 32 H 34 N2S2 m / z = 511.22 [M+H] + , found 511.22 [M+H] + 。

[0072] Compound 10: Yellow solid (24.0 mg, yield: 32%). 11H NMR (600 MHz, CDCl3) δ 7.99 (d, J = 7.5 Hz, 2H), 7.56 (d, J = 7.5 Hz, 2H), 7.49 (t, J = 7.5 Hz, 2H), 3.36 (d, J = 7.1 Hz, 4H), 2.88 (s, 6H), 2.60 (m, 2H), 1.19 (d, J = 6.6 Hz, 12H). 13 13C NMR (151 MHz, CDCl3) δ 154.40, 148.64, 143.00, 138.27, 132.79, 129.16, 126.36, 126.18, 123.34, 120.49, 46.60, 28.02, 22.81, 18.54. Mass spectrum: (Q-TOF): Calcd for C 30 H 30 N2S2 m / z = 483.19 [M] + , found 483.19 [M+H] + .

[0073] Photophysical property characterization:

[0074] The UV-Vis spectra of compounds 1-10 were measured using an Agilent Technologies Cary 60 UV-Vis spectrophotometer. The results are shown as follows. As can be seen from Figure 1 , all the synthesized bisquinoline-like compounds exhibited two main absorption bands, located at around 255-310 nm and 315-365 nm, respectively. The presence of electron-withdrawing and electron-donating groups had no significant effect on the UV absorption spectra, which may be attributed to the large volume and high rigidity of the quinoline-like core relative to the substituents. Figure 1

[0075] The fluorescence spectra of compounds 1-10 were measured using a Horiba FluoroMax-4 fluorescence spectrophotometer. The results are shown as follows. As can be seen from Figure 2 , all the bisquinoline-like compounds exhibited fluorescence, with the emission maxima ranging from 372 to 420 nm. Notably, due to the alkyl chains, the fluorescence emission spectra of compounds 9 and 10 showed a slight blue shift (from 400 nm to 372 nm), which is meaningful for achieving high-purity sky-blue organic light-emitting materials. Figure 2

[0076] ​​The applicant declares that the present invention illustrates the compound with a bisquinoline-like structure, its preparation method and application through the above-mentioned embodiments. However, the present invention is not limited to the above-mentioned embodiments, that is, it does not mean that the present invention must rely on the above-mentioned embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent substitution of the raw materials selected for the present invention, the addition of auxiliary components, the selection of specific methods, etc. all fall within the protection scope and the disclosure scope of the present invention.

Claims

1. A compound of a bisquinoline-like structure, characterized in that: The compound of the bisquinoline structure has a structure shown in the following formula I: wherein ring Ar1 and ring Ar2 are each independently selected from any one of a substituted or unsubstituted C4-C10 heteroaromatic ring and a substituted or unsubstituted C4-C10 heteroaromatic ring; The substituents in the ring Ar1 and the ring Ar2 are each independently selected from any one of hydrogen, halogen, nitro, and C1-C12 straight or branched alkyl; R1 is independently selected from any one of hydrogen, C1-C12 straight chain or branched alkyl; X1 and X2 are each independently selected from any one of O, S and Se.

2. The compound of the bisquinoline-like structure according to claim 1, characterized in that Ring Ar1 is selected from any one of the following groups: in, Represents the attachment site of the group; R2, R3 and R4 are each independently selected from any one of hydrogen, halogen, nitro, C1~C12 straight or branched alkyl, halogen-substituted C1~C12 straight or branched alkyl, and C1~C12 alkoxy.

3. The compound of the bisquinoline-like structure according to claim 1, characterized in that Ring Ar2 is selected from any one of the following groups: Wherein, the dotted line represents the fused bond of the ring; R5, R6, R7 and R8 are each independently selected from any one of hydrogen, halogen, nitro, C1-C12 straight chain or branched alkyl.

4. The compound of the bisquinoline-like structure according to claim 1, characterized in that Ring Ar1 is selected from phenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,5-dimethylphenyl or thienyl; More preferably, the ring Ar2 is selected from a benzene ring or a methyl-substituted benzene ring.

5. The compound of the bisquinoline-like structure according to claim 1, characterized in that R1 is selected from hydrogen, methyl, n-pentyl or 2-methyl-propyl.

6. The compound of the bisquinoline-like structure according to any one of claims 1 to 5, characterized in that: The compound of the bisquinoline-like structure is any one of the following compounds 1-10:

7. The method for preparing a bisquinoline-like compound according to any one of claims 1 to 6, characterized in that: The preparation method comprises the following steps: (1) The compound represented by formula II reacts with the compound represented by formula III to obtain the compound represented by formula IV. The reaction formula is as follows: (2) The compound of formula IV obtained in step (1) is reacted with the aldehyde of formula V to obtain a conjugated compound of a bisquinoline-like structure of formula I or formula II. The reaction formula is as follows:

8. The preparation method according to claim 7, characterized in that: In step (1), the molar ratio of the compound represented by formula II to the compound represented by formula III is 1:2-4; Preferably, the reaction temperature in step (1) is 50-80°C; Preferably, the reaction time in step (1) is 15 to 72 hours; Preferably, the reaction in step (1) is carried out in a solvent; Preferably, the solvent in step (1) comprises tetrahydrofuran or diethyl ether; Preferably, the reaction in step (1) is carried out under the catalysis of a catalyst, and the catalyst is preferably tetrakistriphenylphosphine palladium; Preferably, the reaction in step (1) is carried out in the presence of an alkaline substance, and the alkaline substance is selected from any one or a combination of at least two of potassium carbonate, sodium carbonate, cesium carbonate or potassium acetate.

9. The preparation method according to claim 7, characterized in that: In step (2), the molar ratio of the compound represented by formula IV to the aldehyde represented by formula V is 1:2-4; Preferably, the reaction temperature in step (2) is 80-180°C; Preferably, the reaction time in step (2) is 2.5 to 48 hours; Preferably, the reaction in step (2) is carried out in a solvent; Preferably, the solvent in step (2) comprises any one of toluene, xylene or mesitylene, or a combination of at least two thereof; Preferably, the reaction in step (2) is carried out in the presence of an acidic substance; Preferably, the acidic substance includes an inorganic acid, an organic carboxylic acid, a Lewis acid or other acidic substances; Preferably, the inorganic acid is hydrochloric acid or sulfuric acid; Preferably, the organic carboxylic acid is any one of acetic acid, trifluoroacetic acid, p-toluenesulfonic acid or trifluoromethanesulfonic acid, or a combination of at least two thereof; Preferably, the Lewis acid is boron trifluoride, iodine or gold trichloride; Preferably, the other acidic substance is cyanuric chloride. Preferably, the reaction in step (2) is carried out using a conventional reactor or a microwave reactor.

10. Use of the bisquinoline-like compound according to any one of claims 1 to 6 as an organic light-emitting material.

Images