Organic semiconductor material, preparation method thereof and organic electroluminescent device

Abstract

The invention discloses an organic semiconductor material and a preparation method thereof, and an organic electroluminescent device, the organic semiconductor material is obtained by blending a first compound and a second compound, the chemical formula of the first compound is # imgabs 0 #, and the chemical formula of the second compound is # imgabs 1 #. The organic semiconductor material with a shallower LUMO energy level and a deeper HOMO energy level is obtained by using a heavy element effect, and the band gap width of the organic semiconductor material is effectively increased, so that the light-emitting wavelength of the organic electroluminescent device is obviously blue-shifted; by introducing the high-mobility group and the high-stability group, the stability and mobility of the organic semiconductor material are enhanced; in addition, compared with the existing material, the organic semiconductor material provided by the invention has higher conductivity, higher current efficiency, higher external quantum efficiency, lower driving voltage and longer device service life.

Description

Technical Field

[0001] The present invention relates to the field of organic light emitting technology, and in particular to an organic semiconductor material and a preparation method thereof, and an organic electroluminescent device. Background Art

[0002] Recently, organic light-emitting diode (OLED) display technology has become the focus of flexible display and other technologies. Compared with red and green light, blue light technology has become a technical difficulty that hinders the continued development of OLED panels due to its poor lifespan and low efficiency. Although the first generation of fluorescent technology can achieve a higher blue light display lifespan, its theoretical maximum internal quantum efficiency of 25% has not been broken, resulting in a large number of triplet excitons not being properly utilized. With the development of phosphorescence technology and thermally activated delayed fluorescence technology (TADF), its maximum internal quantum efficiency of 100% can effectively improve the external quantum efficiency. However, TADF materials face serious efficiency roll-off at high brightness, and their device lifespan is far from meeting the commercial use standards. Therefore, the development of long-life, high-brightness deep blue light phosphorescent materials has broad application prospects.

[0003] In OLED devices, the role of the host material is to disperse the guest material and prevent the guest material from being seriously aggregated and quenched in the light-emitting layer due to accumulation. In addition, the host material should also have a high mobility to reduce the energy loss during carrier transmission. In addition, the host material should also match the energy levels of the transmission material and the guest material so that the electrons and holes injected through the electrode can be effectively transmitted. The stability of the host material also directly affects the stability and life of the device. In the field of OLED blue phosphorescence, the development of long-life host materials is of great significance.

[0004] However, existing host materials have defects such as small band gap, poor stability, and low mobility. The small band gap makes the existing host material system difficult to be compatible with blue light materials with shorter luminescent wavelengths. The deeper LUMO energy level and the shallower HOMO energy level make it difficult for electrons and holes to be injected smoothly. The lower stability leads to a poor device life, and the lower mobility leads to greater losses during the electron-hole injection process. The device must be driven with a higher driving voltage, and the higher driving voltage further leads to accelerated device life aging.

[0005] Therefore, the prior art still needs to be improved and developed. Summary of the invention

[0006] In view of the above-mentioned deficiencies in the prior art, the present invention provides an organic semiconductor material and a preparation method thereof, and an organic electroluminescent device, so as to solve the problems of small band gap, poor stability and low mobility of the existing host materials.

[0007] The technical solution adopted by the present invention to solve the above technical problems is as follows:

[0008] In a first aspect of the present invention, an organic semiconductor material is provided. The organic semiconductor material is obtained by mixing a first compound and a second compound. The chemical formula of the first compound is The chemical formula of the second compound is

[0009]

[0010] wherein Ar1, Ar2, and Ar3 are independently hydrogen, deuterium, benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms, or a substituted or unsubstituted aromatic amine group having 3-30 carbon atoms; Ar4, Ar5, Ar6, and Ar7 are independently benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms; L1, L2, and L3 are independently no chemical bond, a direct bond, a substituted or unsubstituted straight carbon chain having 1-8 carbon atoms, or a substituted or unsubstituted sub-aromatic group having 3-30 carbon atoms; Ar8, Ar9, and Ar10 are independently substituted or unsubstituted. 10 ,Ar 11 are independently one of benzene, a substituted or unsubstituted aromatic group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 3 to 30 carbon atoms, Ar 12 ,Ar 13 ,Ar 14 L4, L5 and L6 are independently one of hydrogen, deuterium, benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms, and a substituted or unsubstituted aromatic amine group having 3-30 carbon atoms. L4, L5 and L6 are independently one of a chemical bond-free group, a direct bond, a substituted or unsubstituted straight carbon chain having 1-8 carbon atoms, and a substituted or unsubstituted sub-aromatic group having 3-30 carbon atoms.

[0011] The substituents of the substituted or unsubstituted aryl group having 3 to 30 carbon atoms are one or more of methyl, isopropyl, tert-butyl, cyclohexyl, fluoro, cyano, amino, nitro, aldehyde, ester, alkoxy, and siloxy groups; the substituents of the substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms are one or more of methyl, isopropyl, tert-butyl, cyclohexyl, fluoro, cyano, amino, nitro, aldehyde, ester, alkoxy, and siloxy groups.

[0012] The substituent of the substituted or unsubstituted arylene group having 3 to 30 carbon atoms is one or more of methyl, isopropyl, tert-butyl, cyclohexyl, fluoro, cyano, amino, nitro, aldehyde, ester, alkoxy and siloxy.

[0013] The substituent of the substituted or unsubstituted aromatic amine group having 3 to 30 carbon atoms is one or more of methyl, isopropyl, tert-butyl, cyclohexyl, fluoro, cyano, amino, nitro, aldehyde, ester, alkoxy and siloxy groups.

[0014] The organic semiconductor material provided by the present invention can be used as the main material in the light-emitting layer of an organic electroluminescent device. The present invention introduces the heavy metal element bismuth into the main material (i.e., the organic semiconductor material), and obtains a material with a deeper HOMO (highest occupied molecular orbital) and a shallower LUMO energy level (lowest unoccupied molecular orbital), a larger energy band width and a higher triplet energy level by utilizing the heavy element effect. The organic semiconductor material of the present invention utilizes the heavy element effect of the bismuth element, and the spin-orbit coupling of the molecule is enhanced, thereby increasing the probability of S0→T1 absorption transition and S1→T1 system-to-system crossover, increasing the number of T1 state particles, effectively increasing the band gap width of the main material, making the luminescent wavelength significantly blue-shifted, and being compatible with guest materials with shorter luminescent wavelengths, achieving better display effects. The heavy element effect of the heavy metal element bismuth is utilized in the present invention, and high-mobility groups such as dibenzofuranyl and fluorenyl are introduced to effectively increase the mobility of the main material, reduce the loss of electrons and holes in the injection process, and have a greater current efficiency and a lower turn-on voltage than existing materials, thereby effectively improving the external quantum efficiency. Since the material of the present invention has a higher mobility and introduces side chain groups with high stability such as dibenzofuranyl, fluorenyl, biphenyl, etc., the operating voltage of the device during operation is effectively reduced, so that the device of the material of the present invention has a longer life.

[0015] Preferably, part or all of the hydrogen atoms in the first compound and the second compound are hydrogen atoms, protium atoms or deuterium atoms.

[0016] Preferably, the mass ratio of the first compound to the second compound is (4-8):(2-6).

[0017] Preferably, the mass ratio of the first compound to the second compound is 60:27.

[0018] Preferably, the first compound is one of the following structures:

[0019]

[0020]

[0021] The second compound is one of the following structures:

[0022]

[0023]

[0024] A second aspect of the present invention provides a method for preparing the above-mentioned organic semiconductor material, the preparation method comprising the following steps: mixing a first compound and a second compound to obtain an exciplex, namely the organic semiconductor material.

[0025] Preferably, the method for preparing the first compound comprises the following steps:

[0026] Dissolve bismuth trichloride in solvent 1, and add organic metal compounds M-Ar2, M-Ar3, and M-Ar1-L1-X containing Ar2, Ar3, and Ar1 in sequence at a low temperature below 0°C to react and obtain intermediate A-1;

[0027] Intermediate A-2 and intermediate A-3 are dissolved in solvent 2, and reacted in the presence of catalyst 1 and base 1 to obtain intermediate A-4;

[0028] The intermediate A-1 and the intermediate A-4 are dissolved in a solvent 3, and reacted in the presence of a catalyst 2 and a base 1 to obtain a first compound;

[0029] The route of the above reaction is as follows:

[0030]

[0031] Preferably, the solvent 1 is tetrahydrofuran, n-hexane, ether or toluene, the organometallic compound includes but is not limited to an organic lithium reagent, an organic magnesium reagent, an organic copper reagent, the solvent 2 is N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone, the catalyst 1 is copper powder or cuprous iodide, the base 1 is potassium tert-butoxide or sodium tert-butoxide, the catalyst 2 is a palladium catalyst, including but not limited to tetrakis(triphenylphosphine)palladium, tetrakis(tri-tert-phosphine)palladium, bis(triphenylphosphine)palladium dichloride, the solvent 3 is N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone, and the base 1 is potassium tert-butoxide or sodium tert-butoxide.

[0032] Preferably, the method for preparing the second compound comprises the following steps:

[0033] Dissolve bismuth trichloride in solvent 1, and add the following in turn at a low temperature below 0°C: 12 ,Ar 13 ,Ar 14 Organometallic compounds M-Ar 12 、M-Ar 13 、M-Ar 14 -L6-X, the reaction yields intermediate A-5;

[0034] The intermediate A-6 and trichlorotriazine are dissolved in solvent 1 at a low temperature below 0°C, and after the reaction, the intermediate A7 is added and reacted at a low temperature below 0°C to obtain the intermediate A-8;

[0035] The intermediate A-1, magnesium and iodine are dissolved in a solvent 4, and refluxed at a temperature higher than the boiling point of the solvent 4, and then the intermediate A-8 is added to react to obtain a second compound;

[0036] The route of the above reaction is as follows:

[0037]

[0038] Preferably, the solvent 1 is tetrahydrofuran, n-hexane, diethyl ether or toluene, the organometallic compound includes but is not limited to an organolithium reagent, an organomagnesium reagent, and an organocopper reagent, and the solvent 4 is tetrahydrofuran or diethyl ether.

[0039] In a third aspect of the present invention, an organic electroluminescent device is provided, comprising a cathode, an anode and a light-emitting layer disposed between the cathode and the anode, wherein the light-emitting layer is prepared from a host material and a guest material, wherein the host material is the above-mentioned organic semiconductor material;

[0040] In the light-emitting layer, the mass fraction of the guest material is 5%-15%, the mass fraction of the first compound is 45%-70%, and the mass fraction of the second compound is 25%-40%.

[0041] Preferably, the light-emitting layer is prepared by mixing the first compound, the second compound and the guest material in a certain ratio, and then using evaporation, spin coating, blade coating and other methods.

[0042] Preferably, during the evaporation process, the guest material, the first compound and the second compound are placed in different evaporation sources respectively, and the evaporation rates are controlled to deposit them into thin films according to different mass ratios.

[0043] Preferably, during the spin coating and blade coating process, the guest material, the first compound and the second compound are configured into different concentration components of the same solution, and then the thin film is prepared by the spin coating and blade coating process.

[0044] Beneficial effects:

[0045] The invention discloses an organic semiconductor material and a preparation method thereof, and an organic electroluminescent device. The heavy metal element bismuth is introduced into the organic semiconductor material of the invention, and the heavy element effect is utilized to obtain an organic semiconductor material with a shallower LUMO and a deeper HOMO energy level, thereby effectively increasing the band gap width of the organic semiconductor material, so that the luminescent wavelength of the organic electroluminescent device is significantly blue-shifted. The invention enhances the stability and mobility of the organic semiconductor material by introducing a high-mobility group and a high-stability group. In addition, compared with existing materials, the organic semiconductor material of the invention has higher conductivity, higher current efficiency, higher external quantum efficiency, lower driving voltage and longer device service life. DETAILED DESCRIPTION

[0046] The present invention provides an organic semiconductor material and a method for preparing the same, and an organic electroluminescent device. The technical solutions in the embodiments of the present invention are described clearly and completely below. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments, and are only for illustrating the present invention but not for limiting the present invention. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in the field without creative work are within the scope of protection of the present invention.

[0047] Example 1

[0048]

[0049] Intermediate 1 Synthesis method: Dissolve bismuth trichloride (10 g, 31.7 mmol) in 50 mL of strictly dehydrated tetrahydrofuran, and cool the mixed solution to -78°C, then quickly add 33.4 mL of 1.9 M phenyl lithium (63.4 mmol) dibutyl ether solution to the reaction system and stir vigorously, stir at -78°C for 2 hours, and continue stirring at 0°C for 12 hours. After the reaction, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by intermediate 1 (9.84 g, yield 78%).

[0050] 1HNMR(500MHz,Chloroform-d)δ7.64-7.58(m,4H),7.40-7.34(m,4H),7.34-7.27(m,2H).

[0051]

[0052] Synthesis method of intermediate 2: 1,3-dibromobenzene (2.9 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran that had been strictly dehydrated, and the mixture was cooled to -78°C, and then 5 mL of 2.5 M butyl lithium (12.5 mmol) n-hexane solution was slowly added to the reaction system and stirred vigorously. After reacting at -78°C for 2 hours, intermediate 1 (5 g, 12.5 mmol) was added and stirred for 2 hours, and then stirred at 0°C for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain the compound represented by intermediate 2 (4.48 g, yield 69%).

[0053] 1HNMR(500MHz,Chloroform-d)δ7.70(t,J=1.9Hz,1H),7.60-7.52(m,4H),7.54(d,J=1.7Hz,2H),7.37-7.24(m,7H).

[0054] Example 2

[0055]

[0056] Synthesis method of intermediate 3: 4-bromodibenzofuran (30 g, 121.4 mmol) was dissolved in 200 mL of tetrahydrofuran strictly dehydrated, and the mixture was cooled to -78°C, then 53.4 mL of 2.5 M butyl lithium (133.5 mmol) n-hexane solution was slowly added to the reaction system and stirred vigorously, after reacting at -78°C for 2 hours, bismuth trichloride (38.3 g, 121.4 mmol) was added and stirred for 2 hours, and then stirred for 12 hours at 0°C to obtain intermediate 3-1. The reaction system was cooled to -78°C, 63.9 mL of 1.9 M phenyl lithium (121.4 mmol) dibutyl ether solution was slowly added to the reaction system and stirred vigorously, after reacting at -78°C for 2 hours, the reaction system was heated to 0°C and continued to react for 12 hours to obtain intermediate 3-2. Take another flask and dissolve 1,3-dibromobenzene (28.5g, 121.4mmol) in 200mL of tetrahydrofuran that has been strictly dehydrated, and cool the above mixture to -78°C. Slowly drop 48.6mL of 2.5M butyl lithium (121.4mmol) n-hexane solution into the reaction system and stir vigorously. After reacting at -78°C for 2 hours, use a double-ended needle to transfer the reaction mixture to the reaction system containing intermediate 3-2 and stir vigorously at -78°C for 4 hours. Then warm the reaction mixture to 0°C and continue stirring for 24 hours. After the reaction is completed, filter the mixture, extract with chloroform, extract the aqueous phase with 300mL of dichloromethane three times, combine the organic phases, dry with anhydrous magnesium sulfate, and purify the crude product by silica gel column chromatography to obtain the compound represented by intermediate 3 (22.9g, yield 31%).

[0057] 1HNMR(500MHz,Chloroform-d)δ8.06(dd,J=9.0,1.2Hz,1H),7.97(dd,J=8.5,1.3Hz,1H),7.70(t,J=1.9Hz,1H),7.6 6(dd,J=6.8,1.2Hz,1H),7.59(ddd,J=7.1,1.9,1.2Hz,1H),7.57-7.51(m,2H),7.55-7.39(m,2H),7.41-7.23(m,8H).

[0058] Example 3

[0059] In this embodiment, the synthesis method of other asymmetric Bi-containing intermediates is listed. The only difference from the method in Example 2 of the present invention is that the chemical raw materials used are different. Taking Example 2 as an example, the first step raw material in the one-pot reaction is defined as raw material A, the second step raw material is defined as raw material B, and the third step raw material is defined as raw material C. Intermediate products with different structures can be obtained by different raw materials A, raw materials B and raw materials C. The structural formulas of intermediate products with different structures obtained by different raw materials A, raw materials B and raw materials C are listed in Table 1 below.

[0060]

[0061] Table 1: Intermediate structures obtained by using different raw materials A, B, and C according to the method of Example 2

[0062]

[0063]

[0064] The following is the hydrogen NMR spectrum of the above intermediate:

[0065] Intermediate 4: 1 H NMR (500MHz, Chloroform-d) δ7.72-7.65(m,2H),7.68-7.63(m,2H),7.62-7.53(m,10H),7.48-7.32(m,7H),7.28(t,J=7.3Hz,1H).

[0066] Intermediate 5: 1H NMR(500MHz,Chloroform-d)δ7.99-7.94(m,2H),7.84(ddt,J=11.3,7.0,1.4Hz,4H),7.69(t,J=1.9Hz,1H),7.63(ddd,J=7.1,2.0, 1.3Hz,1H),7.53-7.46(m,4H),7.44(dd,J=7.3,1.2Hz,2H),7.39(td,J=7.2,1.2Hz,2H),7.37-7.32(m,1H),7.28(t,J=7.3Hz,1H).

[0067] Intermediate 6: 1 H NMR(500MHz,Chloroform-d)δ8.06(dd,J=9.1,1.3Hz,2H),7.97(dd,J=8.3,1.2Hz,2H),7.70-7.65(m,2H),7.65(d,J=1.5Hz,1H),7.62(dt,J=7.1,1.6Hz, 1H),7.48(ddd,J=8.9,6.7,1.4Hz,2H),7.41(d,J=17.2Hz,1H),7.41-7.36(m ,1H),7.38-7.32(m,2H),7.28(t,J=7.3Hz,1H),7.24(dt,J=8.6,0.9Hz,2H).

[0068] Intermediate 7: 1 H NMR (500MHz, Chloroform-d) δ7.76-7.68(m,3H),7.60-7.55(m,2H),7.55-7.48(m,2H),7.49(d,J=2.3Hz,2H),7.40-7.24(m,7H),1.55(s,6H).

[0069] Intermediate 7: 1 H NMR(500MHz,Chloroform-d)δ7.96-7.90(m,3H),7.87(dd,J=7.6,2.1Hz,1H),7.81(d,J=2.1Hz,1H),7.71 -7.65(m,2H),7.64-7.59(m,2H),7.57-7.52(m,2H),7.49(ddd,J=6.9,3.6,2.2Hz,2H),7.39-7.27(m,5H).

[0070] Intermediate 13: 1H NMR(500MHz,Chloroform-d)δ8.24(dd,J=6.9,1.0Hz,1H),8.01(dd,J=7.4,1.4Hz,1H) ,7.79-7.72(m,1H),7.59-7.50(m,5H),7.44(dd,J=7.4,1.2Hz,1H),7.36-7.23(m,7H).

[0071] Example 4

[0072]

[0073] Synthesis method of compound 1: Carbazole (15 g, 89.7 mmol) and 3-bromo-9H-carbazole (22.1 g, 89.7 mmol) were added to 200 mL of N,N-dimethylformamide which had been strictly dehydrated in a nitrogen atmosphere. Copper powder (0.57 g, 8.9 mmol) and potassium carbonate (37.2 g, 269.1 mmol) were added in a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, the aqueous phase was extracted three times with 300 mL of dichloromethane, the organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain 9H-3,9'-bicarbazole (25.6 g, yield 86%).

[0074] 1 H NMR(500MHz,Chloroform-d)δ9.47(s,1H),8.14(dt,J=7.4,1.4Hz,3H),7.87(d,J=2.2Hz,1H),7.69-7.62(m,2H),7.59(d,J=8 .0Hz,1H),7.52(dd,J=7.6,1.5Hz,1H),7.40(dd,J=8.1,2.2Hz,1H),7.38-7.33(m,1H),7.36-7.27(m,4H),7.27-7.20(m,1H).

[0075] In a nitrogen atmosphere, intermediate 2 (5 g, 9.6 mmol) and 9H-3,9'-bicarbazole (3.5 g, 10.6 mmol) were added to 50 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.011 g, 0.096 mmol) and sodium tert-butoxide (1.85 g, 19.2 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 1 (5.32 g, yield 72%).

[0076] 1 H NMR(500MHz,Chloroform-d)δ8.17-8.09(m,3H),7.89(d,J=2.1Hz,1H),7.73(t,J=1.9Hz,1H),7.68-7.63( m,4H),7.57-7.52(m,4H),7.48-7.43(m,2H),7.41(t,J=6.2Hz,1H),7.39-7.35(m,2H),7.35-7.28(m,12H).

[0077] Example 5

[0078]

[0079] Synthesis method of compound 2: In a nitrogen atmosphere, intermediate 4 (10 g, 14.9 mmol) and 9H-3,9'-bicarbazole (5.45 g, 16.4 mmol) were added to 100 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.17 g, 0.15 mmol) and sodium tert-butoxide (2.86 g, 29.8 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 2 (9.48 g, yield 69%).

[0080] 1 H NMR(500MHz,Chloroform-d)δ8.17-8.07(m,3H),7.89(d,J=2.1Hz,1H),7.73(t,J=1.9Hz,1H), 7.68-7.63(m,8H),7.62-7.54(m,8H),7.49-7.42(m,6H),7.42-7.35(m,5H),7.35-7.27(m,5H).

[0081] Example 6

[0082]

[0083] Synthesis of compound 4: In a nitrogen atmosphere, intermediate 4 (8 g, 11.9 mmol) and 9H-3,9'-bicarbazole (4.36 g, 13.1 mmol) were added to 100 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.14 g, 0.12 mmol) and sodium tert-butoxide (2.29 g, 23.8 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 4 (7.58 g, yield 71%).

[0084] 1 H NMR(500MHz,Chloroform-d)δ8.17-8.08(m,3H),7.99-7.94(m,2H),7.89(d,J=2.1Hz,1H),7.84(ddt,J=11.5,7.0 ,1.5Hz,4H),7.77(t,J=2.0Hz,1H),7.68-7.62(m,4H),7.54-7.47(m,5H),7.47-7.41(m,3H),7.41-7.27(m,10H).

[0085] Example 7

[0086]

[0087] Synthesis of compound 12: In a nitrogen atmosphere, intermediate 3 (15 g, 24.6 mmol) and 9H-3,9'-bicarbazole (8.99 g, 27.1 mmol) were added to 150 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.29 g, 0.25 mmol) and sodium tert-butoxide (4.72 g, 49.2 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 12 (11.4 g, yield 66%).

[0088] 1H NMR(500MHz,Chloroform-d)δ8.18-8.09(m,3H),8.06(dd,J=9.0,1.3Hz,1H),7. 97(dd,J=8.6,1.3Hz,1H),7.89(d,J=2.1Hz,1H),7.74(t,J=1.9Hz,1H),7.70-7.6 1(m,5H),7.57-7.51(m,2H),7.50-7.47(m,2H),7.46(dd,J=3.3,1.7Hz,1H),7.42 -7.38(m,2H),7.38-7.35(m,2H),7.35-7.28(m,8H),7.26(dd,J=8.7,1.2Hz,1H).

[0089] Example 8

[0090]

[0091] Synthesis of compound 16: In a nitrogen atmosphere, intermediate 6 (10 g, 14.3 mmol) and 9H-3,9'-bicarbazole (5.23 g, 15.7 mmol) were added to 100 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.17 g, 0.14 mmol) and sodium tert-butoxide (2.75 g, 28.6 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 16 (9.79 g, yield 72%).

[0092] 1 H NMR(500MHz,Chloroform-d)δ8.17-8.08(m,3H),8.06(dd,J=9.1,1.3Hz,2H),7.97(dd,J=8.6,1.2Hz,2H),7.89(d,J=2. 1Hz,1H),7.76(t,J=1.9Hz,1H),7.69-7.62(m,6H),7.51-7.44(m,4H),7.42-7.28(m,12H),7.24(dd,J=8.6,1.2Hz,2H).

[0093] Example 9

[0094]

[0095] Synthesis of compound 38: In a nitrogen atmosphere, intermediate 7 (12 g, 17.5 mmol) and 9H-3,9'-bicarbazole (6.4 g, 19.3 mmol) were added to 120 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.202 g, 0.014 mmol) and sodium tert-butoxide (3.37 g, 35.0 mmol) were added under a nitrogen atmosphere and reacted at 120°C for 24 hours. After the reaction, the mixture was filtered, extracted with chloroform, and the aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and the crude product was purified by silica gel column chromatography to obtain compound 38 (12.9 g, yield 79%).

[0096] 1 H NMR(500MHz,Chloroform-d)δ8.17-8.07(m,3H),7.92-7.86(m,4H),7.83-7.76(m,2H),7.68-7.58( m,7H),7.57-7.52(m,2H),7.49(ddd,J=6.9,3.5,2.2Hz,2H),7.47-7.41(m,2H),7.40-7.25(m,11H).

[0097] Example 10

[0098]

[0099] Synthesis of Compound 51: Compound 1 (8 g, 10.4 mmol) was added to 100 mL of deuterated benzene. Anhydrous zinc chloride (5.66 g, 41.5 mmol) was added under a nitrogen atmosphere and reacted at 100°C for 24 hours. After the reaction, the mixture was filtered and extracted with chloroform. The aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography to obtain Compound 51 (8.22 g, yield 99%).

[0100] HRMS(ESI):calcd for C 42 HD 29 BiN2[M+H] + 800.4002, found 800.4104. Example 11

[0101]

[0102] Synthesis of intermediate 8: Dissolve carbazole (10 g, 59.9 mmol) in 100 mL of strictly dehydrated tetrahydrofuran, cool the mixture to -78°C, then quickly add 26.4 mL of 2.5 M butyl lithium (65.9 mmol) in cyclohexane to the reaction system and stir vigorously. After stirring the reaction at -78°C for 1 hour, add trichlorotriazine (5.52 g, 30 mmol) and stir for 1 hour. Continue stirring the reaction at 0°C for 12 hours. After the reaction is completed, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by intermediate 8 (7.89 g, yield 59%).

[0103] 1 H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.2Hz,4H),7.75(dd,J=6.3,1.4Hz,4H),7.46(dd d,J=7.5,6.3,1.3Hz,2H),7.39(ddd,J=7.4,6.3,1.2Hz,2H),7.31(ddd,J=8.6,7.2,1.4Hz,4H).

[0104] Synthesis of compound 56: Dissolve intermediate 2 (14 g, 26.9 mmol) in 150 mL of strictly dehydrated ether, and add magnesium (1.29 g, 53.9 mmol) and iodine (0.14 g, 0.54 mmol) in a flask under a nitrogen atmosphere. Heat the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 8 (13.2 g, 29.6 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 56 (17.8 g, yield 78%).

[0105] 1 H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.1Hz,4H),7.85(ddd,J=8.8,2.2,1.2Hz,1H),7.76(dd,J=6.3,1.4Hz,4H),7.74-7.6 8(m,2H),7.61(dd,J=8.8,7.1Hz,1H),7.58-7.51(m,4H),7.46(ddd,J=7.4,6.3,1.1Hz,2H),7.42-7.36(m,2H),7.36-7.26(m,10H).

[0106] Example 12

[0107]

[0108] Synthesis of compound 58: Dissolve intermediate 4 (9 g, 13.4 mmol) in 100 mL of strictly dehydrated ether, and add magnesium (0.64 g, 26.8 mmol) and iodine (0.034 g, 0.14 mmol) to the above mixture under a nitrogen atmosphere. Heat the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 8 (6.57 g, 14.7 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 58 (9.67 g, yield 72%).

[0109] 1 H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.1Hz,4H),7.85(ddd,J=8.8,2.2,1.2Hz,1H),7.76(dd,J=6.3,1.4Hz,4H),7.7 4-7.68(m,2H),7.67-7.63(m,4H),7.63-7.54(m,9H),7.45(tdd,J=8.1,6.5,1.1Hz,6H),7.41-7.35(m,4H),7.34-7.28(m,4H).

[0110] Embodiment 13

[0111]

[0112] Synthesis method of intermediate 9: 3,6-diphenyl-9,H-carbazole (10 g, 31.3 mmol) was dissolved in 100 mL of tetrahydrofuran that had been strictly dehydrated, and the mixture was cooled to -78°C. 13.8 mL of 2.5 M butyl lithium (34.4 mmol) cyclohexane solution was quickly added to the reaction system and stirred vigorously. After stirring the reaction at -78°C for 1 hour, trichlorotriazine (2.89 g, 15.7 mmol) was added and stirred for 1 hour. The reaction was continued to stir at 0°C for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain the compound represented by intermediate 9 (5.99 g, yield 51%).

[0113] 1H NMR(500MHz,Chloroform-d)δ8.21(d,J=2.0Hz,1H),8.11(d,J=2.0Hz,1H),7.97(d,J=6.8Hz,1H),7.8 4-7.76(m,2H),7.71(dd,J=6.8,2.2Hz,1H),7.64-7.56(m,4H),7.49-7.41(m,4H),7.41-7.34(m,2H).

[0114] Synthesis of compound 60: Dissolve intermediate 2 (6 g, 11.6 mmol) in 50 mL of strictly dehydrated ether, and add magnesium (0.55 g, 23.2 mmol) and iodine (0.03 g, 0.12 mmol) to the above mixture under a nitrogen atmosphere. Heat the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 9 (4.79 g, 6.38 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 60 (8.43 g, yield 63%).

[0115] 1 H NMR(500MHz,Chloroform-d)δ8.21(d,J=2.0Hz,2H),8.11(d,J=2.0Hz,2H),7.98(d,J=6.8Hz,2H),7.85(ddd,J=8.8,2.2,1.2Hz,1H), 7.83-7.78(m,4H),7.74-7.68(m,4H),7.64-7.58(m,9H),7.57-7.52(m,4H),7.49-7.42(m,8H),7.41-7.36(m,4H),7.35-7.24(m,6H).

[0116] Embodiment 14

[0117]

[0118] Synthesis method of intermediate 10: 4-bromo-9,H-carbazole (20 g, 81.3 mmol) and 1-naphthaleneboronic acid (15.4 g, 89.4 mmol) were dissolved in 150 mL of strictly dehydrated toluene. Tetrakis(triphenylphosphine)palladium (0.47 g, 0.41 mmol) and potassium carbonate (22.5 g, 162.6 mmol) were added to the reaction system under a nitrogen atmosphere. The reaction was stirred at 110°C for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain the compound represented by intermediate 10 (22.2 g, yield 93%).

[0119] 1 H NMR(500MHz,Chloroform-d)δ9.66(s,1H),8.14(dd,J=7.1,1.4Hz,1H),8.07-7.98( m,2H),7.96-7.90(m,1H),7.67-7.53(m,3H),7.52-7.45(m,4H),7.45-7.30(m,3H).

[0120] Synthesis method of intermediate 11: Intermediate 10 (20 g, 68.2 mmol) and 2,3-dichloro-5,6-dicyanobenzoquinone (46.4 g, 204.6 mmol) were dissolved in 500 mL of dichloromethane. The reaction was stirred at room temperature for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain the compound represented by intermediate 11 (11.5 g, yield 58%).

[0121] 1 H NMR(500MHz,Chloroform-d)δ9.43(s,1H),8.16-8.02(m,4H),7.69(dd,J=7.4,1 .4Hz,2H),7.65-7.59(m,2H),7.51(dd,J=8.0,1.4Hz,2H),7.46(t,J=7.7Hz,2H).

[0122] Synthesis of intermediate 12: Intermediate 11 (10 g, 34.3 mmol) was dissolved in 100 mL of tetrahydrofuran that had been strictly dehydrated, and the mixture was cooled to -78°C. 15.1 mL of 2.5 M butyl lithium (37.8 mmol) cyclohexane solution was quickly added to the reaction system and stirred vigorously. After stirring the reaction at -78°C for 1 hour, trichlorotriazine (3.16 g, 17.2 mmol) was added and stirred for 1 hour. The reaction was continued to stir at 0°C for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the crude product was purified by silica gel column chromatography to obtain the compound represented by intermediate 12 (5.71 g, yield 48%).

[0123] 1 H NMR(500MHz,Chloroform-d)δ8.13-8.07(m,4H),7.99(d,J=7.2Hz,4H),7.90(dd,J=7.3, 1.1Hz,2H),7.84(dd,J=5.2,3.2Hz,2H),7.67-7.57(m,10H),7.45(dd,J=7.1,6.4Hz,2H).

[0124] Synthesis of compound 68: Dissolve intermediate 2 (5 g, 7.2 mmol) in 50 mL of strictly dehydrated ether, and add magnesium (0.34 g, 14.4 mmol) and iodine (0.017 g, 0.07 mmol) in a flask under a nitrogen atmosphere. Warm the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 12 (4.99 g, 7.2 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 68 (4.03 g, yield 51%).

[0125] 1 H NMR(500MHz,Chloroform-d)δ8.13-8.07(m,4H),7.99(d,J=7.1Hz,4H),7.90(dd,J=7.3,1.1Hz,2H),7.87-7.82( m,3H),7.74-7.67(m,2H),7.66-7.58(m,11H),7.57-7.51(m,4H),7.45(dd,J=7.2,6.3Hz,2H),7.36-7.26(m,6H).

[0126] Embodiment 15

[0127]

[0128] Synthesis of compound 79: Dissolve intermediate 3 (12 g, 19.7 mmol) in 100 mL of strictly dehydrated ether, and add magnesium (0.95 g, 39.4 mmol) and iodine (0.05 g, 0.2 mmol) to the above mixture under a nitrogen atmosphere. Heat the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 8 (4.4 g, 9.9 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 79 (7.5 g, yield 81%).

[0129] 1H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.1Hz,4H),8.06(dd,J=9.0,1.2Hz,1H),7.97(dd,J=8.6,1.3Hz,1H),7.85(ddd,J=8.8,2.2,1.2Hz ,1H),7.75(td,J=7.2,6.8,1.3Hz,5H),7.70(t,J=2.2Hz,1H),7.66(dd,J=6.7,1.5Hz,1H),7.61(dd,J=8.8,7.2Hz,1H),7.56-7.52(m,2H),7.51-

[0130] 7.28(m,14H),7.26(dd,J=8.7,1.2Hz,1H).

[0131] Example 16

[0132]

[0133] Synthesis of compound 94: Dissolve intermediate 13 (11 g, 19.3 mmol) in 100 mL of strictly dehydrated ether, and add magnesium (0.92 g, 38.6 mmol) and iodine (0.05 g, 0.2 mmol) to the above mixture under a nitrogen atmosphere. Heat the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 8 (4.3 g, 9.7 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by vacuum distillation, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 94 (6.69 g, yield 77%).

[0134] 1 H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.1Hz,4H),8.11-8.01(m,2H),7.91(dd,J=7.2,1.1Hz,1H),7.76(d d,J=6.2,1.5Hz,4H),7.64-7.50(m,6H),7.49-7.42(m,3H),7.39(ddd,J=7.5,6.2,1.2Hz,2H),7.36-7.27(m,10H).

[0135] Embodiment 17

[0136]

[0137] Synthesis of intermediate 14: Intermediate 2 (10 g, 19.3 mmol) was added to 100 mL of deuterated benzene. Anhydrous zinc chloride (5.25 g, 38.6 mmol) was added under a nitrogen atmosphere and reacted at 100° C. for 24 hours. After the reaction, the mixture was filtered and extracted with chloroform. The aqueous phase was extracted three times with 300 mL of dichloromethane. The organic phases were combined and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography to obtain intermediate 14 (10.2 g, yield 99%).

[0138] Synthesis of compound 101: Dissolve intermediate 14 (5 g, 9.38 mmol) in 50 mL of strictly dehydrated ether, and add magnesium (0.45 g, 18.8 mmol) and iodine (0.025 g, 0.1 mmol) in a flask under a nitrogen atmosphere. Warm the reaction system to reflux temperature and stir vigorously. Continue stirring for 1 hour after the mixture turns reddish brown to complete the reaction. Add intermediate 8 (2.09 g, 4.69 mmol) to the reaction system and stir at reflux temperature for 4 hours. After the reaction is completed, add water to quench, remove the solvent by distillation under reduced pressure, and purify the crude product by silica gel column chromatography to obtain the compound represented by compound 101 (3.32 g, yield 82%).

[0139] 1 H NMR(500MHz,Chloroform-d)δ8.23(dd,J=7.8,1.1Hz,4H),7.76(dd,J=6.4,1.4Hz,4H),7.46(ddd,J=7 .3,6.2,1.1Hz,2H),7.39(ddd,J=7.4,6.3,1.3Hz,2H),7.31(td,J=7.6,1.4Hz,4H).HRMS(ESI):calcd for C45H17D14BiN5[M+H]+864.3302,found864.3299.

[0140] Application Examples

[0141] The application example of the present invention provides anthracene-based An organic electroluminescent device of a similar host material comprises a metal cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, a hole transport layer, a hole injection layer, and an ITO anode stacked in sequence from top to bottom, and the device is prepared by an evaporation method.

[0142] The metal cathode is aluminum, with a deposition rate of 0.1-0.3nm / s and a thickness of 120nm;

[0143] The electron injection layer uses lithium fluoride, with a evaporation rate of 0.05-0.1nm / s and a thickness of 5nm;

[0144] The electron transport layer is formed by co-doping mSiTrz and Liq with the following structure, wherein the doping ratio of mSiTrz and Liq is 50:50, the evaporation rate is 0.05-0.1nm / s, and the thickness is 30nm;

[0145]

[0146] The hole blocking layer uses a compound mSiTrz having the following structure, with a deposition rate of 0.05-0.1 nm / s and a thickness of 5 nm;

[0147]

[0148] The light-emitting layer is formed by co-doping a host material and a guest material, wherein the host material is composed of a P-type semiconductor material represented by the first compound provided by the present invention and an N-type semiconductor material represented by the second compound. The host material is compared with the currently commercialized P-type semiconductor material SiCzCz and N-type semiconductor material SiTrzCz2 composed of an excited compound host material, and the guest material is PtON-tb-DTB having the following structure, and the mass ratio of the host material to the guest material is P-type semiconductor material: N-type semiconductor material: guest material = 60:27:13, the evaporation rate is 0.003-0.2nm / s, and the thickness is 35nm;

[0149]

[0150] The electron blocking layer uses a compound SiCzCz with the following structure, with a deposition rate of 0.05-0.1nm / s and a thickness of 5nm;

[0151]

[0152] The hole transport layer uses a compound BCFN with the following structure, with a deposition rate of 0.05-0.1 nm / s and a thickness of 60 nm;

[0153]

[0154] The hole injection layer uses the compound HATCN with the following structure, with a deposition rate of 0.05-0.1 nm / s and a thickness of 10 nm;

[0155]

[0156] The anode is made of indium tin oxide (ITO).

[0157] The performance of organic electroluminescent devices prepared using different host materials was tested, and the results are shown in Table 2:

[0158] Table 2: Device performance table

[0159]

[0160]

[0161] As can be seen from Table 2, the host material provided by the present invention, compared with the commercial material LBH001, has a lower turn-on voltage, a lower color coordinate y value, a higher current efficiency, external quantum efficiency and a longer lifespan in the organic electroluminescent device prepared.

[0162] Performance Testing

[0163] By DFT calculation simulation method, Spartan 22 software, B3LYP functional, 6-31G (d, p) basis set. The main material prepared in the embodiment of the present invention is compared with the currently commercialized material, and the results are shown in Table 3 and Table 4:

[0164] Table 3: Performance values ​​of the simulation

[0165]

[0166]

[0167] Table 4: Performance values ​​of the simulation

[0168]

[0169]

[0170] It can be seen from the calculation data and device data that the main material (i.e., organic semiconductor material) provided by the present invention introduces the heavy metal element bismuth into the main material compared with the commercial materials SiCzCz and SiTrzCz2, and the heavy element effect is used to obtain a material with a deeper HOMO and a shallower LUMO energy level, a larger energy band width and a higher triplet energy level. The organic semiconductor material of the present invention effectively increases the band gap width of the main material, makes the luminescent wavelength significantly blue-shifted, obtains a smaller color coordinate y value, and is compatible with guest materials with shorter luminescent wavelengths to achieve better display effects. In the present invention, the heavy element effect of the heavy metal element bismuth is utilized, and the introduction of high-mobility groups effectively increases the mobility of the main material, reduces the loss of electrons and holes in the injection process, and has a greater current efficiency and a lower turn-on voltage than existing materials, thereby effectively improving the external quantum efficiency. Since the mobility of the material of the present invention is higher and a side chain group with higher stability is introduced, the operating voltage of the device during operation is effectively reduced, so that the device of the material of the present invention has a longer life.

[0171] In summary, the host material provided by the present invention can be applied to an organic electroluminescent device to effectively improve the performance of the device, including efficiency, color coordinates and service life.

[0172] It should be understood that the application of the present invention is not limited to the above examples. For ordinary technicians in this field, improvements or changes can be made based on the above description. All these improvements and changes should fall within the scope of protection of the claims attached to the present invention.

Claims

1. An organic semiconductor material, characterized in that The organic semiconductor material is obtained by mixing a first compound and a second compound, wherein the chemical formula of the first compound is The chemical formula of the second compound is wherein Ar1, Ar2, and Ar3 are independently hydrogen, deuterium, benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms, or a substituted or unsubstituted aromatic amine group having 3-30 carbon atoms; Ar4, Ar5, Ar6, and Ar7 are independently benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms; L1, L2, and L3 are independently no chemical bond, a direct bond, a substituted or unsubstituted straight carbon chain having 1-8 carbon atoms, or a substituted or unsubstituted sub-aromatic group having 3-30 carbon atoms; Ar8, Ar9, and Ar10 are independently substituted or unsubstituted. 10 ,Ar 11 are independently one of benzene, a substituted or unsubstituted aromatic group having 3 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 3 to 30 carbon atoms, Ar 12 ,Ar 13 ,Ar 14 L4, L5 and L6 are independently one of hydrogen, deuterium, benzene, a substituted or unsubstituted aromatic group having 3-30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 3-30 carbon atoms, and a substituted or unsubstituted aromatic amine group having 3-30 carbon atoms. L4, L5 and L6 are independently one of a chemical bond-free group, a direct bond, a substituted or unsubstituted straight carbon chain having 1-8 carbon atoms, and a substituted or unsubstituted sub-aromatic group having 3-30 carbon atoms.

2. The organic semiconductor material according to claim 1, characterized in that Some or all of the hydrogen atoms in the first compound and the second compound are hydrogen atoms, protium atoms or deuterium atoms.

3. The organic semiconductor material according to claim 1, characterized in that The mass ratio of the first compound to the second compound is (4-8):(2-6).

4. The organic semiconductor material according to claim 1, characterized in that The first compound is one of the following structures: The second compound is one of the following structures:

5. A method for preparing an organic semiconductor material according to claim 1, characterized in that: The preparation method comprises the following steps: The first compound and the second compound are mixed to obtain an exciplex, which is the organic semiconductor material.

6. The method for preparing an organic semiconductor material according to claim 5, characterized in that: The preparation method of the first compound comprises the following steps: Dissolve bismuth trichloride in solvent 1, and add organic metal compounds M-Ar2, M-Ar3, and M-Ar1-L1-X containing Ar2, Ar3, and Ar1 in sequence at a low temperature below 0°C to react to obtain intermediate A-1; Intermediate A-2 and intermediate A-3 are dissolved in solvent 2, and reacted in the presence of catalyst 1 and base 1 to obtain intermediate A-4; The intermediate A-1 and the intermediate A-4 are dissolved in a solvent 3, and reacted in the presence of a catalyst 2 and a base 1 to obtain a first compound; The route of the above reaction is as follows:

7. The method for preparing an organic semiconductor material according to claim 6, characterized in that: The solvent 1 is tetrahydrofuran, n-hexane, ether or toluene, the solvent 2 is N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone, the catalyst 1 is copper powder or cuprous iodide, the base 1 is potassium tert-butoxide or sodium tert-butoxide, the catalyst 2 is a palladium catalyst, the solvent 3 is N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone, and the base 1 is potassium tert-butoxide or sodium tert-butoxide.

8. The method for preparing an organic semiconductor material according to claim 5, characterized in that: The preparation method of the second compound comprises the following steps: Dissolve bismuth trichloride in solvent 1, and add the following in turn at a low temperature below 0°C: 12 ,Ar 13 ,Ar 14 Organometallic compounds M-Ar 12 、M-Ar 13 、M-Ar 14 -L6-X, the reaction yields intermediate A-5; The intermediate A-6 and trichlorotriazine are dissolved in solvent 1 at a low temperature below 0°C, and after the reaction, the intermediate A7 is added and reacted at a low temperature below 0°C to obtain the intermediate A-8; The intermediate A-1, magnesium and iodine are dissolved in a solvent 4, and refluxed at a temperature higher than the boiling point of the solvent 4, and then the intermediate A-8 is added to react to obtain a second compound; The route of the above reaction is as follows:

9. The method for preparing an organic semiconductor material according to claim 8, characterized in that: The solvent 1 is tetrahydrofuran, n-hexane, diethyl ether or toluene, and the solvent 4 is tetrahydrofuran or diethyl ether.

10. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and a light-emitting layer arranged between the cathode and the anode, wherein the light-emitting layer is prepared from a host material and a guest material, and the host material is the organic semiconductor material according to claim 1; In the light-emitting layer, the mass fraction of the guest material is 5%-15%, the mass fraction of the first compound is 45%-70%, and the mass fraction of the second compound is 25%-40%.

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