An organic photoelectric material and its application

Abstract

The present application relates to the technical field of organic optoelectronic devices, and specifically discloses an organic optoelectronic material and its application. The organic optoelectronic material comprises a group having the following general formula: wherein R1 and R3 are the same or different in each case, and R1 and R3 are hydrogen, deuterium, fluorine, chlorine, bromine, iodine, alkylamine, cyano, alkoxy, ester alkyl, carbonyl alkyl, silane, borane, phosphoalkyl, thioalkyl, a straight-chain alkyl group having 1 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, or a branched or cyclic alkyl group having 3 to 20 carbon atoms; the present application utilizes a benzene ring to construct a large conjugated system, introduces at least two heteroatoms into the main molecular structure so that the molecule is in an electron-deficient state, and the obtained organic optoelectronic material is used as a matrix material of a light-emitting layer, has a higher triplet energy level and a higher glass transition temperature, and enhances the luminous efficiency and life of the device.

Description

Technical Field

[0001] The present application relates to the technical field of organic optoelectronic devices, and more specifically, to an organic optoelectronic material and its application. Background Art

[0002] Organic light-emitting diode (OLED) is a new high-performance display technology with the characteristics of high color gamut, low energy consumption, wide viewing angle, easy bending, self-luminescence, etc. It is considered to be the mainstream technology for the next generation of display. Due to its broad application prospects in the field of information display, OLED has received widespread attention from academia and industry. In recent years, various display technology powers have continued to increase their investment in OLED display technology. In OLED, high-quality presentation of the three primary colors of red, green, and blue is a necessary condition for full-color OLED display technology, and it is also its main feature. At present, in the field of OLED display technology, compared with achieving high-performance red and green light emission, blue OLED with high luminous efficiency and good device stability is more difficult to achieve, which is mainly due to the unsatisfactory performance of blue organic light-emitting materials. On the one hand, blue light emission requires materials with a wider band gap than red and green light materials, which makes its synthesis and purification difficult; on the other hand, the blue light material has a poor match with other auxiliary materials (such as hole injection layer materials, etc.) in the device, resulting in poor luminous efficiency and stability; especially in OLEDs that exhibit triplet luminescence (phosphorescence), efficiency, operating voltage and life span still need to be improved. In addition, other materials used in OLEDs, such as matrix materials or charge transport materials, are also particularly important in OLEDs. Therefore, improvements to these materials can also lead to improved OLED performance. Based on the above statements, optimizing organic blue light molecules from the perspective of material design and synthesis is of great significance to the realization of full-color OLED display technology. Summary of the invention

[0003] In order to solve the defects of the prior art, the present application provides an organic photoelectric material and its application.

[0004] On the one hand, the present application provides an organic optoelectronic material, which adopts the following technical solution:

[0005] An organic photoelectric material, wherein the organic photoelectric material has the following general formula:

[0006]

[0007] In the general formula: R1 and R3 are the same or different in each case, and R1 and R3 are hydrogen, deuterium, fluorine, chlorine, bromine, iodine, alkylamine, cyano, alkoxy, ester alkyl, carbonyl alkyl, silanyl, borane, phosphine, thioalkyl, straight-chain alkyl groups having 1 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, branched or cyclic alkyl groups having 3 to 20 carbon atoms; the alkyl, alkenyl or alkynyl groups in each case can be substituted by one or more;

[0008] R2 is selected from at least one of a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted condensed aryl group, a substituted or unsubstituted condensed heteroaryl group, a substituted or unsubstituted carbazolyl group and its derivative groups, a substituted or unsubstituted diphenylamine group and its derivative groups, a substituted or unsubstituted triphenylamine group and its derivative groups, and an acridinium group and its derivative groups;

[0009] M and N are identical or different in each case, and M and N are selected from O, Se, S, N-R4, Si-(R5)2, C-(R6)2, B-(R7), S=O, P=O;

[0010] The R4-R7 is selected from at least one of substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted condensed aryl, substituted or unsubstituted condensed heteroaryl, substituted or unsubstituted carbazolyl and its derivatives, substituted or unsubstituted diphenylamine and its derivatives, substituted or unsubstituted triphenylamine and its derivatives, and acridinium and its derivatives.

[0011] Preferably, the hydrogen atoms in R1-R7 can be fully deuterated, partially deuterated or undeuterated.

[0012] Preferably, M and N are different, M is S or Se; N is O or N-R4.

[0013] Preferably, the organic photoelectric material has the following general formula:

[0014]

[0015] Preferably, R1 and R3 are the same and are selected from the following structures:

[0016]

[0017] Preferably, the R2 is selected from the following structures:

[0018]

[0019] Preferably, the R4 is selected from the following structures:

[0020]

[0021] Preferably, the organic photoelectric material is selected from any one of the compounds represented by the following structural formulas:

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028] In a second aspect, the present application provides an application of an organic optoelectronic material, using the following technical solution:

[0029] An application of an organic photoelectric material, wherein the organic photoelectric material is applied to an organic electroluminescent device.

[0030] Preferably, the organic electroluminescent device comprises a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode; wherein the one or more organic material layers contain the above-mentioned organic photoelectric material.

[0031] Preferably, the organic material layer further includes a transparent substrate layer, an ITO anode layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking / electron transport layer, an electron injection layer and a cathode reflective electrode layer; and the transparent substrate layer, the ITO anode layer, the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking / electron transport layer, the electron injection layer and the cathode reflective electrode layer are stacked in sequence from bottom to top.

[0032] Preferably, the organic optoelectronic material is used as a host material of a phosphorescent emitter, a fluorescent emitter or a thermally activated delayed fluorescent emitter in a light-emitting layer.

[0033] Preferably, the organic optoelectronic material is used in an electron transport layer.

[0034] Preferably, the organic optoelectronic material is used in a hole blocking layer.

[0035] In summary, this application has the following beneficial effects:

[0036] The organic photoelectric material of the present application utilizes benzene rings to construct a large conjugated system, and introduces at least two heteroatoms into the main molecular structure so that the molecule is in an electron-deficient state. The obtained organic photoelectric material serves as a matrix material for a light-emitting layer, and has a higher triplet energy level and a higher glass transition temperature. In addition, the combination of an electron donor (donor, D) and an electron acceptor (acceptor, A) in the organic photoelectric material molecule can effectively improve the balanced migration of carriers and enhance the luminous efficiency and life of the device.

[0037] The organic optoelectronic material of the present application is suitable for use in OLEDs, especially as a matrix material for phosphorescent emitters or as an electron transport material, and can significantly improve the comprehensive performance of OLEDs, such as efficiency, operating voltage and lifespan. DETAILED DESCRIPTION

[0038] The present application is further described in detail below with reference to the embodiments.

[0039] Embodiments 1-5 provide an organic optoelectronic material.

[0040] Example 1

[0041] Synthesis of an organic photoelectric material SO-1:

[0042]

[0043] Synthesis of SO-1-M1: 1-Chloro-3-(3-chlorophenoxy)benzene (11.95 g, 50 mmol) was added to a glass reaction bottle under a nitrogen atmosphere, and dried THF (100 ml) was added, cooled to -75 ° C, and nitrogen was used to replace three times to remove the air in the reaction bottle. Subsequently, n-butyl lithium (2.5 mol / l tetrahydrofuran solution, 40 ml, 100 mmol, drop rate 5 ml / min) was added dropwise, and the temperature was controlled at -52 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for another 6 h, and then liquid bromine (2.7 ml, 54.6 mmol, added in 3 times, drop rate 0.9 ml / min) was added in batches, and the temperature was controlled at -65 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for 1 h, then warmed to 10 ° C and stirred for 1 h. Then cool to 0°C and inject saturated Na2SO3 solution (30ml) into the reaction bottle to quench the reaction. After stirring for 0.5h, the mixture was extracted with ethyl acetate (100ml) and saturated NaCl aqueous solution (100ml each time, extracted 3 times). The organic phase was dried over Na2SO4, and the organic solvent (ethyl acetate) was removed on a rotary evaporator. 2-propanol was added and refluxed for 1h, and ethyl acetate (100ml) and saturated NaCl aqueous solution (100ml each time, extracted 3 times) were used to extract again. The organic phase was distilled under reduced pressure to obtain SO-1-M1. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M1 were as follows: 1 H NMR (400MHz, CDCl3) δ7.53 (s, 1H), 7.47 (s, 1H), 7.32-7.30 (s, 2H), 7.27 (s, 1H), 7.14 (s, 1H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C12H6BrClO, 281.53, found: 281.34. Elemental Analysis: C, 51.20; H, 2.15; Br, 28.38; Cl, ​​12.59; O, 5.68.

[0044] Synthesis of SO-1-M2: SO-1-M1 (14 g, 49.8 mmol), Pd(dppf)C l2(0.143g, 0.2mmol), dry tetrahydrofuran (100ml) were put into the reaction bottle, nitrogen was used for three times to remove the air in the reaction bottle, and trimethyl (thiophene-2-yl) stannane (12.22g, 49.5mmol) was added and the reaction mixture was stirred under reflux for 12h. After the reaction was completed, ethyl acetate (100ml) and water (100ml each time, extracted 3 times) were used for extraction and treatment, the organic phase was washed with water and saturated NaCl solution and dried over Na2SO4, and the solvent was removed on a rotary evaporator. The obtained crude product was recrystallized using methanol (80ml), filtered and dried to obtain SO-1-M2. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M2 were as follows: 1 HNMR (400MHz, CDCl3) δ7.82 (s, 1H), 7.70-7.69 (s, 2H), 7.57 (m, 1H), 7.47 (s, 1H), 7.40 (s, 1H), 7.32 (s, 1H), 7.14-7.13 (dd, 2H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C16H9ClOS, 284.76, found: 284.54. Elemental Analysis: C, 67.49; H, 3.19; Cl, ​​12.45; O, 5.62; S, 11.26.

[0045] Synthesis of SO-1-M3: SO-1-M2 (14.05 g, 50 mmol) and K2CO3 (20.73 g, 150 mmol) were added to the reaction bottle, and then N, N-dimethylformamide (200 ml) was added. After nitrogen was used for three times, nitrogen protection was continued. Subsequently, Pd(OAc)2 (223 mg, 0.99 mmol) and 1,3-bis(2,6-diisopropylphenyl)-3H-imidazole-1-chloride (0.845 g, 1.99 mmol) were added, and the reaction mixture was stirred at 130 ° C for 20 h. After cooling, the mixture was poured into ethanol / water (1:1, 400 ml), stirred for another 30 min, and then filtered, and the upper filter cake was washed with water and ethanol. Then, SO-1-M3 was obtained by recrystallization and filtration using petroleum ether and drying. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M3 were as follows: 1 HNMR (400MHz, CDCl3) δ8.17 (s, 1H), 8.11 (s, 1H), 7.88 (s, 2H), 7.68-7.66 (s, 2H), 7.63 (s, 2H). HRMS(ESI,Positive)(m / z):[M] +Calcd for: C16H8OS, 248.30, found: 248.21. Elemental Analysis: C, 77.40; H, 3.25; O, 6.44; S, 12.91.

[0046] Synthesis of SO-1-M4: SO-1-M3 (12.41 g, 50 mmol) was added to a glass reaction bottle under an argon atmosphere, and dried THF (120 ml) was added and cooled to -75 °C. Nitrogen was used to replace three times to remove the air in the reaction bottle. Subsequently, lithium diisopropylamide (2.5 mol / l tetrahydrofuran solution, 25 ml, 50 mmol, drop rate 5 ml / min) was added dropwise, and the temperature was controlled at -45 °C during the addition. After the addition was completed, trimethyltin chloride (10 ml, 50 mmol, added in 3 times, drop rate 2 ml / min) was added dropwise in batches, and the temperature was controlled at -62 °C during the addition. After the addition was completed, the mixture was stirred at room temperature for 12 h, and then a saturated Na2SO3 solution (60 ml, drop rate 10 ml / min) was added dropwise to quench the reaction. After stirring for 0.5 h, the mixture was extracted with petroleum ether (100 ml) and a saturated NaCl aqueous solution (100 ml each time, extracted 3 times), and the organic phase was dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain SO-1-M4. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M4 were as follows: 1 H NMR (400MHz, CDCl3) δ 8.17 (s, 1H), 8.11 (s, 1H), 7.88 (s, 2H), 7.63 (dd, 2H), 7.59 (s, 1H), 0.27 (m, 12H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C19H16OSSn, 411.99, found: 411.49. Elemental Analysis: C, 55.51; H, 3.92; O, 3.89; S, 7.80; Sn, 28.88.

[0047] Synthesis of SO-1-M5: Add bromobenzene (8.6 g, 55 mmol) to a glass reaction bottle, add dried 1,4-dioxane (160 ml), then add SO-1-M4 (20.60 g, 50 mmol), and then use nitrogen to replace three times to remove the air in the reaction bottle, add Pd(OAc)2 (0.56 g, 2.5 mmol), reflux for 6 hours, and after the reaction, use petroleum ether (100 ml) and saturated NaCl aqueous solution (100 ml each time, 3 times of extraction) to extract, the organic phase is dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) is removed on a rotary evaporator, and recrystallized with acetone, filtered and dried to obtain SO-1-M5. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M5 are as follows: 1 H NMR (400MHz, CDCl3) δ8.17 (s, 1H), 8.11 (s, 1H), 7.88 (s, 2H), 7.82 (s, 2H), 7.63 (dd, 2H), 7.59 (s, 1H), 7.48 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C22H12OS, 324.40, found: 324.31. Elemental Analysis: C, 81.46; H, 3.73; O, 4.93; S, 9.88.

[0048] Synthesis of SO-1-M6: SO-1-M5 (32.4 g, 100 mmol) was added to a glass reaction bottle, and then anhydrous acetonitrile and dichloromethane (200 ml, v / v = 1:1) were added, followed by 1,3,5-tribromo-1,3,5-thiazinane-2,4,6-trione (76.65 g, 210 mmol), stirred at 50 ° C for 12 h, and then the reaction solution was poured into ice water, filtered, and the filter cake was washed with acetone 3 times and dried to obtain SO-1-M6. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1-M6 were as follows: 1 H NMR (400MHz, CDCl3) δ8.29 (s, 2H), 8.05 (s, 2H), 7.82 (m, 2H), 7.59 (s, 1H), 7.48 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C22H10Br2OS, 482.19, found: 482.07. Elemental Analysis: C, 54.80; H, 2.09; Br, 33.14; O, 3.32; S, 6.65.

[0049] Synthesis of SO-1: SO-1-M6 (12 g, 25 mmol) and potassium carbonate (20.73 g, 150 mmol) were added to a glass reaction bottle, and then toluene (100 ml) was added and stirred evenly. Then N-phenyl-3-carbazole boronic acid (15.78 g, 55 mmol), tetrakis(triphenylphosphine) palladium (1.4 g, 1.25 mmol), and tetrabutylammonium chloride (0.69 g, 0.25 mmol) were added, and the reaction was refluxed for 18 h. After the reaction, the mixture was extracted with ethyl acetate (100 ml) and saturated NaCl aqueous solution (100 ml each time, 3 times), and the organic phase was dried over Na2SO4. The solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain a crude product of SO-1. The crude product was purified by column chromatography, and ethyl acetate, dichloromethane, and petroleum ether were used as eluents (volume ratio 1:1:6). The eluent containing SO-1 was collected, and the eluent was dried under reduced pressure to obtain SO-1. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-1 are as follows: 1 HNMR (400MHz, CDCl3) δ8.46 (s, 2H), 8.30 (d, 2H), 8.22 (s, 2H), 8.19 (d, 2H), 8.13 (dd, 2H), 7.8 9(s, 2H), 7.82(d, 2H), 7.62(m, 4H), 7.59(s, 1H), 7.58(m, 4H), 7.50-7.48(m, 9H), 7.20(m, 2H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C58H34N2OS,806.98, found:806.77. Elemental Analysis: C, 86.33; H, 4.25; N, 3.47; O, 1.98; S, 3.97.

[0050] Example 2

[0051] Synthesis of an organic photoelectric material SO-3:

[0052]

[0053] Compared with the synthesis of SO-1, the operations in step 1 to step 6 remain unchanged, and only the operation in step 7 is changed. The specific steps of step 7 are as follows:

[0054] Synthesis of SO-3: SO-1-M6 (12g, 25mmol) and potassium carbonate (20.73g, 150mmol) were added to a glass reaction bottle, and N, N-dimethylformamide (120ml) was added and stirred evenly. Then phenoxazine (10.06g, 55mmol) and cuprous iodide (1.4g, 1.25mmol) were added, and the reaction was refluxed for 18h. After the reaction, the mixture was extracted with ethyl acetate (100ml) and saturated NaCl aqueous solution (100ml each time, extracted 3 times), and the organic phase was dried over Na2SO4. The solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain a crude SO-3 product. The crude product was purified by column chromatography, and ethyl acetate, dichloromethane, and petroleum ether were used as eluents (volume ratio 1:1:6). The eluent containing SO-3 was collected, and the decompression was dried and dried to obtain SO-3. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-3 were as follows: 1 H NMR (400MHz, CDCl3) δ7.90 (s, 2H), 7.82 (s, 2H), 7.66 (s, 2H), 7.59 (s, 1H), 7.48 (m, 3H), 7.14 (dd, 4H), 7.01 (m, 8H), 6.96 (m, 4H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C46H26N2O3S, 686.79, found: 686.66. Elemental Analysis: C, 80.45; H, 3.82; N, 4.08; O, 6.99; S, 4.67.

[0055] Example 3

[0056] Synthesis of an organic photoelectric material SO-10:

[0057]

[0058] Compared with the synthesis of SO-1, the operations in step 1-step 4 remain unchanged, and only the operations in step 5-step 7 are changed. The specific steps of step 5-step 7 are as follows:

[0059] Synthesis of SO-10-M5: Add bromocyclohexane (8.6 g, 55 mmol) to a glass reaction bottle, add dried 1,4-dioxane (160 ml), then add SO-1-M4 (20.60 g, 50 mmol), and then use nitrogen to replace three times to remove the air in the reaction bottle, add Pd(OAc)2 (0.56 g, 2.5 mmol), reflux for 6 hours, and after the reaction, use petroleum ether (100 ml) and saturated NaCl aqueous solution (100 ml each time, 3 times of extraction) to extract, the organic phase is dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) is removed on a rotary evaporator, and recrystallized with acetone, filtered and dried to obtain SO-10-M5. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-10-M5 are as follows: 1 H NMR (400MHz, CDCl3) δ8.17 (d, 1H), 8.11 (d, 2H), 7.88 (dd, 2H), 7.63 (m, 2H), 7 .40 (s, 1H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C22H18OS, 330.45, found: 330.45. Elemental Analysis: C, 79.97; H, 5.49; O, 4.84; S, 9.70.

[0060] Synthesis of SO-10-M6: SO-10-M5 (32.4 g, 100 mmol) was added to a glass reaction bottle, and then anhydrous acetonitrile and dichloromethane (200 ml, v / v = 1:1) were added, followed by 1,3,5-tribromo-1,3,5-thiazinane-2,4,6-trione (76.65 g, 210 mmol), stirred at 50 ° C for 12 h, and then the reaction solution was poured into ice water, filtered, and the filter cake was washed with acetone 3 times and dried to obtain SO-10-M6. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-10-M6 were as follows: 1 H NMR (400MHz, CDCl3) δ 8.29 (d, 2H), 8.05 (s, 2H), 7.40 (s, 1H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H). HRMS(ESI,Positive)(m / z):[M] +Calcd for:C22H16Br2OS, 488.24, found: 488.03. Elemental Analysis: C, 54.12; H, 3.30; Br, 32.73; O, 3.28; S, 6.57.

[0061] Synthesis of SO-10: Add SO-10-M6 (12 g, 25 mmol) and potassium carbonate (20.73 g, 150 mmol) into a glass reaction bottle, and then add toluene (100 ml) and stir evenly. Then, 1-phenyl-1H-benzimidazolylboronic acid (15.78 g, 55 mmol), tetrakis(triphenylphosphine)palladium (1.4 g, 1.25 mmol), and tetrabutylammonium chloride (0.69 g, 0.25 mmol) were added, and the reaction was refluxed for 18 h. After the reaction, the mixture was extracted with ethyl acetate (100 ml) and saturated NaCl aqueous solution (100 ml each time, extracted 3 times), and the organic phase was dried over Na2SO4. The solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain a crude product of SO-10. The crude product was purified by column chromatography, and ethyl acetate, dichloromethane, and petroleum ether were used as eluents (volume ratio 1:1:6). The eluent containing SO-10 was collected, and the product was dried after decompression and spin-drying to obtain SO-10. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SO-10 were as follows: 1 H NMR (400MHz, CDCl3) δ8.56 (d, 2H), 8.46 (s, 2H), 8.22 (s, 2H), 7.81 (d, 2H), 7.62 (d, 2H), 7.53 (m, 2H), 7.48 (m, 4H), 7.40(s, 1H), 7.38(m, 4H), 7.28(m, 2H), 2.72(m, 1H), 1.76(m, 2H), 1.53-1.51(m, 4H), 1.46-1.43(m, 4H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C48H34N4OS,714.89, found:714.67. Elemental Analysis: C, 80.65; H, 4.79; N, 7.84; O, 2.24; S, 4.48.

[0062] Example 4

[0063] Synthesis of an organic photoelectric material SN-34:

[0064]

[0065] Synthesis of SN-34-M1: 3-Chloro-N-(3-chlorophenyl)-N-aniline (11.95 g, 50 mmol) was added to a glass reaction bottle under a nitrogen atmosphere, and dried THF (100 ml) was added, cooled to -75 ° C, and nitrogen was used to replace three times to remove the air in the reaction bottle. Subsequently, n-butyl lithium (2.5 mol / l tetrahydrofuran solution, 40 ml, 100 mmol, drop rate 5 ml / min) was added dropwise, and the temperature was controlled at -52 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for another 6 h, and then liquid bromine (2.7 ml, 54.6 mmol, added in 3 times, drop rate 0.9 ml / min) was added in batches, and the temperature was controlled at -65 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for 1 h, and then the temperature was raised to 10 ° C and stirred for 1 h. Then cool to 0°C and inject saturated Na2SO3 solution (30ml) into the reaction bottle to quench the reaction. After stirring for 0.5h, the mixture was extracted with ethyl acetate (100ml) and saturated NaCl aqueous solution (100ml each time, extracted 3 times), the organic phase was dried over Na2SO4, the organic solvent (ethyl acetate) was removed on a rotary evaporator, and 2-propanol was added to reflux for 1h, and ethyl acetate (100ml) and saturated NaCl aqueous solution (100ml each time, extracted 3 times) were used to extract again, and the organic phase was distilled under reduced pressure to obtain SN-34-M1. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M1 are as follows: 1 H NMR (400MHz, CDCl3) δ7.82 (d, 1H), 7.62 (m, 2H), 7.58 (dd, 1H), 7.52-7.50 (m, 3H), 7.34 (d, 1H), 7.27-7.26 (m, 2H), 7.01 (s, 1H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C18H11BrClN, 356.65, found: 356.25. Elemental Analysis: C, 60.62; H, 3.11; Br, 22.40; Cl, ​​9.94; N, 3.93.

[0066] Synthesis of SN-34-M2: SN-34-M1 (14 g, 49.8 mmol), Pd(dppf)C l2(0.143g, 0.2mmol), dry tetrahydrofuran (100ml) were put into the reaction bottle, nitrogen was used for three times to remove the air in the reaction bottle, and trimethyl (thiophene-2-yl) tin ane (12.22g, 49.5mmol) was added and the reaction mixture was stirred under reflux for 12h. After the reaction was completed, ethyl acetate (100ml) and water (100ml each time, 3 extractions) were used for extraction and treatment, the organic phase was washed with water and saturated NaCl solution and dried over Na2SO4, and the solvent was removed on a rotary evaporator. The crude product was recrystallized using methanol (80ml), filtered and dried to obtain SN-34-M2. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M2 were as follows: 1 H NMR (400MHz, CDCl3) δ8.22 (d, 1H), 8.04 (d, 1H), 7.58 (dd, 1H), 7.70 (d, 1H), 7.62 (m, 2H), 7.58 (m, 1H), 7.52-7.50 (m, 3H), 7.46 (d, 1H), 7.40 (d, 1H), 7.31 (m, 1H), 7.13 (d, 1H), 7.01 (d, 1H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C22H14ClNS, 359.87, found: 359.80. Elemental Analysis: C, 73.43; H, 3.92; Cl, ​​9.85; N, 3.89; S, 8.91.

[0067] Synthesis of SN-34-M3: SN-34-M2 (14.05 g, 50 mmol) and K2CO3 (20.73 g, 150 mmol) were added to the reaction bottle, and then N, N-dimethylformamide (200 ml) was added. After nitrogen was replaced three times, nitrogen protection was continued. Subsequently, Pd(OAc)2 (223 mg, 0.99 mmol) and 1,3-bis(2,6-diisopropylphenyl)-3H-imidazole-1-chloride (0.845 g, 1.99 mmol) were added, and the reaction mixture was stirred at 130 ° C for 20 h. After cooling, the mixture was poured into ethanol / water (1:1, 400 ml), stirred for another 30 min, and then filtered. The upper filter cake was washed with water and ethanol. After recrystallization with petroleum ether, filtration was performed and dried to obtain SN-34-M3. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M3 are as follows: 1HNMR (400MHz, CDCl3) δ 8.17 (d, 1H), 8.11 (d, 1H), 7.88 (dd, 2H), 7.78-7.76 (dd, 2H), 7.63-7.62 (m, 4H), 7.58 (m, 1H), 7.50 (dd, 2H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C22H13NS, 323.41, found: 323.30. Elemental Analysis: C, 81.70; H, 4.05; N, 4.33; S, 9.91.

[0068] Synthesis of SN-34-M4: SN-34-M3 (12.41 g, 50 mmol) was added to a glass reaction bottle under an argon atmosphere, and dried THF (120 ml) was added and cooled to -75 °C. Nitrogen was used to replace three times to remove the air in the reaction bottle. Subsequently, lithium diisopropylamide (2.5 mol / l tetrahydrofuran solution, 25 ml, 50 mmol, drop rate 5 ml / min) was added dropwise, and the temperature was controlled at -45 °C during the addition. After the addition was completed, trimethyltin chloride (10 ml, 50 mmol was added in 3 times, drop rate 2 ml / min) was added dropwise in batches, and the temperature was controlled at -65 °C during the addition. After the addition was completed, the mixture was stirred at room temperature for 12 hours, and then a saturated Na2SO3 solution (60 ml, drop rate 10 ml / min) was added dropwise to quench the reaction. After stirring for 0.5 hours, the mixture was extracted with petroleum ether (100 ml) and saturated NaCl aqueous solution (100 ml each time, 3 extractions), and the organic phase was dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain SN-34-M4. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M4 were as follows: 1 H NMR (400MHz, CDCl3) δ 8.17 (d, 1H), 8.11 (d, 1H), 7.88 (dd, 2H), 7.63-7.62 (m, 4H), 7.59-7.58 (m, 2H), 7.50 (dd, 2H), 0.27 (s, 9H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C25H21NSSn, 486.22, found: 486.04. Elemental Analysis: C, 61.76; H, 4.35; N, 2.88; S, 6.59; Sn, 24.41.

[0069] Synthesis of SN-34-M5: Add bromobenzene (8.6 g, 55 mmol) to a glass reaction bottle, add dried 1,4-dioxane (160 ml), then add SN-34-M4 (20.60 g, 50 mmol), and then use nitrogen to replace three times to remove the air in the reaction bottle, add Pd(OAc)2 (0.56 g, 2.5 mmol), reflux for 6 hours, and extract with petroleum ether (100 ml) and saturated NaCl aqueous solution (100 ml each time, 3 times) after the reaction. The organic phase is dried with Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) is removed on a rotary evaporator. Recrystallize with acetone, filter and dry to obtain SN-34-M5. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M5 are as follows: 1 H NMR (400MHz, CDCl3) δ8.17 (d, 1H), 8.11 (d, 1H), 7.88 (dd, 2H), 7.63-7.62 (m, 4H), 7.58 (m, 2H) , 7.50 (dd, 1H), 7.14 (d, 1H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C28H23NS, 405.56, found: 405.34. Elemental Analysis: C, 82.92; H, 5.72; N, 3.45; S, 7.91.

[0070] Synthesis of SN-34-M6: SN-34-M5 (32.4 g, 100 mmol) was added to a glass reaction bottle, and then anhydrous acetonitrile and dichloromethane (200 ml, v / v = 1:1) were added, followed by 1,3,5-tribromo-1,3,5-thiazinane-2,4,6-trione (76.65 g, 210 mmol), stirred at 50 ° C for 12 h, and then the reaction solution was poured into ice water, filtered, and the filter cake was washed 3 times with acetone and dried to obtain SN-34-M6. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34-M6 were as follows: 1 H NMR (400MHz, CDCl3) δ8.29 (d, 2H), 8.05 (d, 2H), 7.62 (m, 2H), 7.58 (m, 2H), 7.50 (dd , 2H), 7.40 (s, 1H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H). HRMS(ESI,Positive)(m / z):[M] +Calcd for:C28H21Br2NS, 563.35, found: 563.28. Elemental Analysis: C, 59.70; H, 3.76; Br, 28.37; N, 2.49; S, 5.69.

[0071] Synthesis of SN-34: SN-34-M6 (12 g, 25 mmol) and potassium carbonate (20.73 g, 150 mmol) were added to a glass reaction bottle, and toluene (100 ml) was added and stirred evenly. Then, N-phenyl-3-carbazole boronic acid (15.78 g, 55 mmol), tetrakis(triphenylphosphine)palladium (1.4 g, 1.25 mmol), and tetrabutylammonium chloride (0.69 g, 0.25 mmol) were added, and the reaction was refluxed for 18 h. After the reaction, the mixture was extracted with ethyl acetate (100 ml) and saturated NaCl aqueous solution (100 ml each time, extracted 3 times), and the organic phase was dried over Na2SO4. The solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain SN-34 crude product. The crude product was purified by column chromatography, with ethyl acetate, dichloromethane, and petroleum ether as eluents (volume ratio 1:1:6), and the eluent containing SN-34 was collected, and SN-34 was obtained after decompression and drying. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SN-34 are as follows: 1 H NMR (400MHz, CDCl3) δ 8.56 (m, 2H), 8.46 (s, 2H), 8.22 (s, 2H), 7.81 (dd, 2H), 7.62 (m, 4H), 7.58 (dd, 1H), 7.53 (dd, 2H), 7.50 ( dd, 2H), 7.48 (m, 4H), 7.40 (S, 1H), 7.38 (m, 4H), 7.28 (m, 2H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C54H39N5S,790.00,found:789.87. Elemental Analysis: C, 82.10; H, 4.98; N, 8.87; S, 4.06.

[0072] Example 5

[0073] Synthesis of an organic photoelectric material SeN-9:

[0074]

[0075] Synthesis of SeN-9-M1: 3-Chloro-N-(3-chlorophenyl)-N-(4-(5-ethylthienyl))aniline (42.40 g, 100 mmol) was added to a glass reaction bottle under a nitrogen atmosphere, and 1,4-dioxane (200 ml) was added after drying, and the temperature was cooled to -75 ° C. The air in the reaction bottle was removed by nitrogen extraction three times. Subsequently, n-butyl lithium (2.5 mol / l n-hexane solution, 80 ml, 200 mmol, drop rate 5 ml / min) was added dropwise, and the temperature was controlled at -52 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for another 6 h, and then liquid bromine (2.7 ml, 54.6 mmol, added in 3 times, drop rate 0.9 ml / min) was added in batches, and the temperature was controlled at -65 ° C during the addition. After the addition was completed, the mixture was stirred at -75 ° C for 1 h, and then the temperature was raised to 10 ° C and stirred for 1 h. Then cool to 0°C and inject saturated Na2SO3 solution (60ml) into the reaction bottle to quench the reaction. After stirring for 0.5h, the mixture was extracted with ethyl acetate (150ml) and saturated NaCl aqueous solution (200ml each time, extracted 3 times). The organic phase was dried over Na2SO4, and the solvent (ethyl acetate and 1,4-dioxane) was removed on a rotary evaporator. Then petroleum ether was added and refluxed for 1h. After cooling, it was filtered and dried to obtain SeN-9-M1. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M1 were as follows: 1 H NMR (400MHz, CDCl3) δ7.92-7.91 (m, 4H), 7.82 (d, 1H), 7.52 (d, 1H), 7.34 (dd, 1H), 7 .31 (d, 1H), 7.27-7.26 (dd, 2H), 7.01 (d, 1H), 6.8 (s, 1H), 2.87 (m, 2H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C24H17BrClNS, 466.82, found: 466.55. Elemental Analysis: C, 61.75; H, 3.67; Br, 17.12; Cl, ​​7.59; N, 3.00; S, 6.87.

[0076] Synthesis of SeN-9-M2: SeN-9-M1 (23.34 g, 50 mmol), Pd(dppf)C l2(0.143g, 0.2mmol), dry cyclohexane (140ml) were put into the reaction bottle, nitrogen was used for 3 times, the air in the reaction bottle was removed, and trimethyl (selenophen-2-yl) tin ane (14.69g, 49.5mmol) was added and the reaction mixture was stirred under reflux for 20h. After the reaction was completed, ethyl acetate (100ml) and water (100ml each time, 3 times of extraction) were used for extraction and treatment, the organic phase was washed with water and saturated NaCl solution and dried over Na2SO4, and the solvent was removed on a rotary evaporator. The crude product was recrystallized using methanol (80ml), filtered and dried to obtain SeN-9-M2. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M2 were as follows: 1 HNMR (400MHz, CDCl3) δ7.92-7.91 (m, 4H), 7.82 (d, 1H), 7.70 (d, 1H), 7.48-7.46 (dd, 2H), 7 .31 (m, 2H), 7.28 (dd, 1H), 7.12 (d, 1H), 7.01 (d, 1H), 6.8 (d, 2H), 2.87 (m, 2H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C28H20ClNSSe, 516.96, found: 516.75. Elemental Analysis: C, 65.06; H, 3.90; Cl, ​​6.86; N, 2.71; S, 6.20; Se, 15.28.

[0077] Synthesis of SeN-9-M3: SeN-9-M2 (12.92 g, 25 mmol) and K2CO3 (10.36 g, 75 mmol) were added to the reaction bottle, and then dimethylacetamide (200 ml) was added. After nitrogen was used for three times, nitrogen was continued to be filled. Subsequently, Pd(OAc)2 (112 mg, 0.50 mmol) and 1,3-bis(2,6-diisopropylphenyl)-3H-imidazole-1-chloride (0.43 g, 1 mmol) were added, and the reaction mixture was stirred at 140 ° C for 30 h. After cooling, the mixture was poured into acetonitrile / water (1:1, 500 ml), stirred for another 30 min, and then filtered, and the upper filter cake was washed with water and ethanol. Subsequently, SeN-9-M3 was obtained by recrystallization with methanol and filtration, and then dried. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M3 are as follows: 1H NMR (400MHz, CDCl3) δ 8.11 (d, 2H), 7.92-7.91 (m, 4H), 7.71 (d, 2H), 7.63 (m, 2H), 7.31 (m, 1H), 7.19 (d, 1H), 6.7 (d, 2H), 2.87 (m, 2H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for:C28H19NSSe, 481.04, found: 480.92. Elemental Analysis: C, 69.99; H, 3.99; N, 2.92; S, 6.67; Se, 16.44.

[0078] Synthesis of SeN-9-M4: SeN-9-M3 (12.2 g, 25 mmol) was added to a glass reaction bottle under a nitrogen atmosphere, and dried toluene (150 ml) was added and cooled to -75 °C. Nitrogen was used for three times to remove the air in the reaction bottle. Subsequently, lithium diisopropylamide (12.5 ml of 2.5 mol / l tetrahydrofuran solution, 25 mmol) was added dropwise, and the temperature was controlled at -52 °C during the addition. After the addition was completed, tributyltin chloride (8.12 g, 25 mmol, added in 3 times, the drop rate was 2 ml / min), and the temperature was controlled at -65 °C during the addition. After the addition was completed, the mixture was stirred at room temperature for 8 h, and then a saturated Na2SO3 solution (60 ml, drop rate 10 ml / min) was added dropwise to quench the reaction. After stirring for 0.5 h, the mixture was extracted with dichloromethane (100 ml) and a saturated NaCl aqueous solution (100 ml each time, extracted 3 times), and the organic phase was dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain SeN-9-M4. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M4 were as follows: 1 H NMR (400MHz, CDCl3) δ8.11 (d, 2H), 7.92-7.91 (m, 4H), 7.71 (d, 2H), 7.63 (m, 2H), 7.31 (m, 2H) , 6.8 (s, 1H), 2.87 (m, 2H), 1.63-1.58 (m, 12H) 1.33-1.29 (m, 13H), 0.92 (m, 3H), 0.88 (m, 6H). HRMS(ESI,Positive)(m / z):[M] +Calcd for:C42H49NSSeSn,799.18, found:799.02. Elemental Analysis: C, 63.25; H, 6.19; N, 1.76; S, 4.02; Se, 9.90; Sn, 14.88.

[0079] Synthesis of SeN-9-M5: Add iodocyclohexane (2.39 g, 11.36 mmol) to a glass reaction bottle, add dried tetrahydrofuran (80 ml), then add SeN-9-M4 (12.39 g, 12.5 mmol), and then use nitrogen to replace three times to remove the air in the reaction bottle, add Pd(OAc)2 (0.1 g, 0.1 mmol), reflux reaction for 2 hours, and after the reaction, use petroleum ether (100 ml) and saturated NaCl aqueous solution (100 ml each time, extraction 3 times) to extract, the organic phase is dried over Na2SO4, and the solvent (petroleum ether and tetrahydrofuran) is removed on a rotary evaporator, and methanol is used for recrystallization, and SeN-9-M5 is obtained by suction filtration and drying. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M5 are as follows: 1 H NMR (400MHz, CDCl3) δ8.11 (d, 2H), 7.92-7.91 (m, 4H), 7.71 (d, 2H), 7.63 (m, 2H), 7.31 (m, 2H), 6.8 ( s, 1H), 2.87 (m, 2H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C34H29NSSe, 562.64, found: 562.54. Elemental Analysis: C, 72.58; H, 5.20; N, 2.49; S, 5.70; Se, 14.04.

[0080] Synthesis of SeN-9-M6: SeN-9-M5 (28.2 g, 50 mmol) was added to a glass reaction bottle, and then anhydrous acetonitrile and dichloromethane (160 ml, v / v = 1:1) were added, followed by 1,3,5-tribromo-1,3,5-thiazinane-2,4,6-trione (40.15 g, 110 mmol), and stirred at 50 ° C for 12 h, and then the reaction solution was poured into ice water, filtered, and the filter cake was washed with acetone 3 times and dried to obtain SeN-9-M6. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9-M6 were as follows: 1H NMR (400MHz, CDCl3) δ8.12 (s, 2H), 7.92-7.91 (m, 4H), 7.88 (s, 2H), 7.31 (d, 1H), 6.89 (s, 1H), 6.80 (s, 1H), 2.87 (m, 2H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] + Calcd for: C34H27Br2NSSe, 720.44, found: 720.05. Elemental Analysis: C, 56.68; H, 3.78; Br, 22.18; N, 1.94; S, 4.45; Se, 10.96.

[0081] Synthesis of SeN-9: Add SeN-9-M6 (18 g, 25 mmol) and potassium carbonate (20.73 g, 150 mmol) into a glass reaction bottle, and then add toluene (100 ml) and stir evenly. Then, 1-phenyl-1H-benzimidazolylboronic acid (13.1 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.7 g, 0.75 mmol), and tetrabutylammonium chloride (0.4 g, 0.1 mmol) were added, and the reaction was refluxed for 18 h. After the reaction, the mixture was extracted with ethyl acetate (100 ml) and saturated NaCl aqueous solution (100 ml each time, extracted 3 times), and the organic phase was dried over Na2SO4. The solvent (petroleum ether and tetrahydrofuran) was removed on a rotary evaporator to obtain a crude SeN-9 product. The crude product was purified by column chromatography, with ethyl acetate, dichloromethane, and petroleum ether as eluents (volume ratio 1:1:6), and the eluent containing SeN-9 was collected, and the SeN-9 was obtained after decompression and drying. After testing, the nuclear magnetic resonance hydrogen spectrum and high-resolution mass spectrum of SeN-9 were as follows: 1 H NMR (400MHz, CDCl3) δ8.56 (d, 2H), 8.29 (s, 2H), 8.19 (d, 1H), 8.05 (s, 2H), 7.98 (s, 1H), 7.81 (d, 2H), 7.53 (m, 2H), 7.48-7.45 (m, 5H), 7.40 (d, 1H), 7.38 (m, 4H), 7.28 (m, 2H), 6.98 (s, 1H), 2.87 (m, 2H), 2.72 (m, 1H), 1.76 (m, 2H), 1.53-1.51 (m, 4H), 1.46-1.43 (m, 4H), 1.30 (m, 3H). HRMS(ESI,Positive)(m / z):[M] +Calcd for:C58H43N5SSe,921.05, found:920.87. Elemental Analysis: C, 75.64; H, 4.71; N, 7.60; S, 3.48; Se, 8.57.

[0082] The synthesis methods of the compounds for which no detailed preparation methods are given are similar to those of the compounds in the above examples and will not be described in detail here.

[0083] Application Examples

[0084] In order to verify whether the properties of the organic photoelectric materials prepared in Examples 1-5 of the present application meet the requirements of organic electroluminescent devices, the applicant used the organic photoelectric materials prepared in Examples 1-5 of the present application as the main materials of the light-emitting layer, and prepared organic electroluminescent devices 1-5 and tested the corresponding performances.

[0085] The organic electroluminescent device comprises a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode. The hole injection layer is disposed on the first electrode; the hole transport layer is disposed on the hole injection layer; the light-emitting layer is disposed on the hole transport layer, the electron transport layer is disposed on the light-emitting layer, the electron injection layer is disposed on the electron transport layer, and the second electrode is disposed on the electron injection layer.

[0086] The first electrode is an anode, and the material used is indium tin oxide.

[0087] The material used for the hole injection layer is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene.

[0088] The material used for the hole transport layer is N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,4'-diamine.

[0089] The materials used for the light-emitting layer include a host material and a guest material (weight ratio of 90:10), wherein the host material is the organic optoelectronic material prepared in Examples 1-5 of the present application and 1,3-dicarbazole-9-ylbenzene (weight ratio of 1:4), and the guest material is 9,9-dimethyl-10-phenylacridine.

[0090] The material used for the electron transport layer is 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene.

[0091] The material used for the electron injection layer is lithium fluoride.

[0092] The second electrode 6 is a cathode, and the material used is aluminum.

[0093] The method for preparing an organic electroluminescent device comprises the following steps:

[0094] The anode substrate with an ITO film with a thickness of 100 nm was cleaned with distilled water, acetone, and isopropanol ultrasonically and placed in an oven for drying. The surface was treated with UV for 30 minutes and then moved to a vacuum deposition chamber. -6 Pa, start evaporating each layer of film, and evaporate 60nm thick 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene to form a hole injection layer. Evaporate 60nm thick N,N'-diphenyl-N,N'-di(1-naphthyl)-1,1'-biphenyl-4,4'-diamine to form a hole transport layer. On the hole transport layer, evaporate the main material and the guest material with a weight ratio of 90:10 at the same time, wherein the main material is the organic optoelectronic material of this application and 1,3-dicarbazole-9-ylbenzene (weight ratio 1:4), and the guest material is 9,9-dimethyl-10-phenylacridine, forming a 30nm thick light-emitting layer. Then evaporate 1,3,5-tri(1-phenyl-1H-benzimidazole-2-yl)benzene on the light-emitting layer to form a 20nm thick electron transport layer. An electron injection layer with a thickness of 1 nm and aluminum with a thickness of 100 nm are sequentially evaporated on the electron transport layer as the electron injection layer and the cathode, thereby manufacturing an organic electroluminescent device.

[0095] Application comparison

[0096] Comparative organic electroluminescent device 1-2 is prepared in the same manner as organic electroluminescent device 1, except that the organic photoelectric material in the main material is different. The organic photoelectric material of comparative device 1 has the following structural formula: The organic photoelectric material of comparative device 2 has the following structural formula:

[0097] Performance Testing

[0098] The current of the organic electroluminescent device prepared according to the application example at different voltages was tested using a Keithley 2365A digital nanovoltmeter, and then the current was divided by the luminescent area to obtain the current density of the organic electroluminescent device at different voltages; the brightness and radiant energy flux density of the organic electroluminescent device prepared according to the application example at different voltages were tested using a Konicaminolta CS-2000 spectroradiometer. According to the current density and brightness of the organic electroluminescent device at different voltages, the current density (0.1 mA / cm 2 ) and the time LT95 required for the brightness to drop to 95% of the initial brightness, the results are shown in Table 1 below.

[0099] Table 1:

[0100]

[0101]

[0102] It can be seen from the data shown in Table 1 above that the organic photoelectric materials prepared in Examples 1-5 are used in the manufacture of organic electroluminescent devices, which can significantly improve the luminous efficiency of the organic electroluminescent devices and extend their practical life.

[0103] This specific embodiment is merely an explanation of the present application and is not a limitation of the present application. After reading this specification, those skilled in the art may make modifications to the present embodiment without any creative contribution as needed, but such modifications are protected by the patent law as long as they are within the scope of the claims of the present application.

Claims

1. An organic photoelectric material, characterized in that: The organic photoelectric material has the following general formula: ； In the general formula: M is S or Se; N is O or N-R4; The R1 and R3 are the same and are selected from the following structures: ； The R2 is selected from the following structures: ； The R4 is selected from the following structures: 。 2. A use of the organic optoelectronic material as claimed in claim 1, characterized in that: The organic photoelectric material is applied in the field of organic photoelectricity.

3. The use of an organic photoelectric material according to claim 2, characterized in that: The organic photoelectric material is applied to an organic electroluminescent device.

4. The use of an organic photoelectric material according to claim 3, characterized in that: The organic optoelectronic material is used as a host material for a phosphorescent light emitter, a fluorescent light emitter or a light emitter exhibiting thermally activated delayed fluorescence in a light-emitting layer; and / or in an electron transport layer; and / or in a hole blocking layer.

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