An organic light emitting compound and an organic electroluminescent composition, a light emitting device, a display device
By using organic light-emitting compounds with specific structures and multifunctional layer structures, carrier injection and transport are optimized, solving the problem of insufficient external quantum efficiency in OLED devices and achieving efficient and stable electroluminescence performance.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- JIHUA LAB
- Filing Date
- 2025-12-10
- Publication Date
- 2026-05-19
AI Technical Summary
The external quantum efficiency of existing OLED devices fails to fully match the theoretical potential of internal quantum efficiency, and the improvement in device performance is limited.
Organic light-emitting compounds with specific structures, such as compound 21, containing specific aromatic and substituent groups, are used to construct organic electroluminescent compositions and apply multifunctional layer structures in devices to optimize carrier injection, transport, and recombination processes.
It improves the external quantum efficiency of organic electroluminescent devices, reduces device efficiency roll-off, and enhances brightness and stability.
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Figure CN121293152B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of electroluminescence, and specifically relates to an organic light-emitting compound and an organic electroluminescent composition, a light-emitting device, and a display device. Background Technology
[0002] Organic semiconductor materials have attracted widespread attention in the optoelectronic field due to their highly designable molecular structures, relatively simple fabrication processes, and excellent photoelectric properties. Organic electronic devices based on these materials, such as organic light-emitting diodes (OLEDs), organic photovoltaic cells, and organic field-effect transistors, have gradually achieved commercial applications, especially playing a crucial role in display and lighting technologies. As self-emissive devices, OLEDs rely on the recombination of holes injected from the anode and electrons injected from the cathode in the functional layer under an applied electric field to form excitons, which then emit light through radiative decay. These devices possess advantages such as self-emission, fast response speed, wide viewing angle, high contrast, and flexibility.
[0003] To further improve device performance, modern OLEDs typically employ a multi-functional layer structure, including a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL), to optimize carrier injection, transport, and recombination processes. Although recent improvements in device structure and materials have significantly enhanced luminous efficiency, and the internal quantum efficiency of OLEDs is now close to its theoretical limit, the external quantum efficiency has not yet fully matched the theoretical potential of the internal quantum efficiency. Summary of the Invention
[0004] The present invention aims to improve at least one technical problem in the prior art.
[0005] The first aspect of this invention provides an organic light-emitting compound with the structure shown in Formula I:
[0006] Formula I;
[0007] Wherein, L1 and L2 are independently selected from substituted or unsubstituted aromatic or heteroaromatic groups with 6 to 30 ring atoms, and at least one of L1 and L2 is selected from benzene, naphthalene, dibenzofuran, dibenzothiophene, fluorene or carbazole;
[0008] R1 and R2 are independently selected from H, D, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxy group, nitro group, CF3, Cl, Br, F, a first group with 1 to 20 carbon atoms, a second group with 2 to 20 carbon atoms, a third group with 3 to 20 carbon atoms, a fourth group with 7 to 20 carbon atoms, a fifth group with 5 to 40 ring atoms, or a combination of these groups;
[0009] The first group is a straight-chain alkyl group, an alkoxy group, a thioalkoxy group, or a substituted ketone group;
[0010] The second group is an alkoxycarbonyl group;
[0011] The third group is a cyclic or branched alkyl group, alkoxy group, thioalkoxy group or silyl group;
[0012] The fourth group is an aryloxycarbonyl group;
[0013] The fifth group is an aryloxy group, a heteroaryloxy group, an aromatic cyclic group, a substituted aromatic cyclic group, a heteroaryl cyclic group, or a substituted heteroaryl cyclic group.
[0014] In some preferred embodiments, the structures of the above-mentioned organic light-emitting compounds are as shown in Formula II-1 or Formula II-2:
[0015] .
[0016] In some preferred embodiments, the structures of the above-described organic light-emitting compounds are as shown in any one of Formulas III-1 to III-6:
[0017] .
[0018] In some preferred embodiments, the structure of the above-described organic light-emitting compound is as shown in any one of Formulas IⅤ-1 to IⅤ-16:
[0019]
[0020]
[0021]
[0022] Where Q is O or S.
[0023] In some preferred embodiments, the structures of the above-described organic light-emitting compounds are as shown in any one of compounds 1 to 96:
[0024]
[0025]
[0026]
[0027]
[0028]
[0029]
[0030]
[0031]
[0032]
[0033]
[0034]
[0035]
[0036]
[0037]
[0038]
[0039]
[0040]
[0041]
[0042]
[0043]
[0044]
[0045]
[0046]
[0047]
[0048]
[0049]
[0050]
[0051]
[0052]
[0053]
[0054]
[0055] .
[0056] More preferably, the structure of the aforementioned organic light-emitting compound is compound 21. When the structure is as shown in compound 21, the highest external quantum efficiency of the organic electroluminescent device composed of it can reach 32.8%, 10000 cd / m². 2 The external quantum efficiency of electroluminescence under certain brightness conditions can reach 29.5%, and the device lifetime (T95) can reach 136.5 h.
[0057] A second aspect of the present invention provides an organic electroluminescent composition comprising a host material and a light-emitting guest material, wherein the light-emitting guest material comprises the aforementioned organic light-emitting compound.
[0058] The content of the main material is 90 wt%-98 wt%, and the content of the luminescent guest material is 2 wt%-10 wt%.
[0059] A third aspect of the present invention provides an organic electroluminescent device, comprising an anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer comprising the above-described organic electroluminescent composition.
[0060] More specifically, the aforementioned organic electroluminescent device comprises, in sequence: an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode.
[0061] A fourth aspect of the present invention provides a display device including the organic electroluminescent device described above.
[0062] The beneficial effects of the present invention are as follows: The organic light-emitting compound provided by the present invention has good photoelectric properties and can be used as a light-emitting guest material in organic electroluminescent devices, which makes the device have the characteristics of high external quantum efficiency, small efficiency roll-off, high brightness and good stability. Attached Figure Description
[0063] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device.
[0064] In the attached diagram: 1-Anode; 2-Hole injection layer; 3-Hole transport layer; 4-Electron blocking layer; 5-Light emitting layer; 6-Electron transport layer; 7-Electron injection layer; 8-Cathode. Detailed Implementation
[0065] The following will provide a clear and complete description of the concept, specific structure, and resulting technical effects of this application in conjunction with embodiments and accompanying drawings, so as to fully understand the purpose, solution, and effects of this application. It should be noted that, unless otherwise specified, the embodiments and features described in these embodiments can be combined with each other.
[0066] The molecular structures of some functional layer materials mentioned below are as follows:
[0067]
[0068] The above-mentioned materials HATCN, TAPC, TCTA, TPBi, HOST, LiQ, complex1, and complex2 are all commercially available or synthesized by existing synthetic methods. The synthesis of compounds 1, 21, 25, and 46 is given below.
[0069] Furthermore, in the following description, mass spectrometry data (Mass Spectra: MS) for molecules with a relative molecular weight below 1000 were obtained using a Thermo Fisher ITQ1100 ion trap gas chromatograph-mass spectrometer, while mass spectrometry data for molecules with a relative molecular weight above 1000 were obtained using a Bruker Autoflex Speed matrix-assisted laser desorption / ionization time-of-flight mass spectrometer. Elemental analysis of the final products was performed using an Elemental Analysis Flash EA1112 instrument.
[0070] Example 1
[0071] An organic light-emitting compound, the structure of which is shown in Compound 1, is synthesized as follows:
[0072]
[0073] Raw materials 1a (CAS:19821-80-8), 1b (CAS:918655-03-5), 2a (CAS:22190-35-8) and 2b (CAS:870774-25-7) can be purchased directly.
[0074] Synthesis of intermediate 1c: 1a (1,3-dibromo-2-iodobenzene, 10.85 g, 30 mmol), 1b (4-(naphthalene-2-)phenylboronic acid, 7.44 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The product 1c was separated by silica gel column chromatography, yielding 7.06 g of the target product 1c, with a yield of 54%. MS (ASAP) = 435.95.
[0075] Synthesis of intermediate 1d: 1c (6.57 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After approximately 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another 30 minutes. The temperature was then raised to room temperature, and the reaction was continued for 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for approximately 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to obtain 4.24 g of 1d, with a yield of 71%. MS (ASAP) = 398.07.
[0076] Synthesis of intermediate 2c: 2a (20 g, 94.78 mmol), 2b (23.51 g, 94.78 mmol), and tetraphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 12 g, a yield of 60%. MS (ASAP) = 334.16.
[0077] Synthesis of Compound 1: Intermediate 2c (25.75 g, 77 mmol), intermediate 1d (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 5 g, a yield of 25%. MS (ASAP) = 653.31.
[0078] Example 2
[0079] An organic light-emitting compound, the structure of which is shown in compound 10; its synthetic route is as follows:
[0080]
[0081] The synthesis of intermediates 1c and 1d is the same as in Example 1.
[0082] Raw materials 1a, 1b, 2a, z1 (CAS: 761405-37-2) and z2 (CAS: 90-11-9) can be purchased directly.
[0083] Synthesis of intermediate 2b-1: In a dry two-necked flask, z1 (dibenzo[b,d]thiophene-2,8-diboronic acid, 25.80 g, 94.78 mmol), z2 (1-bromonaphthalene, 19.63 g, 94.78 mmol), and tetraphenylphosphine palladium (2.26 g, 1.96 mmol) were added, followed by 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane. The mixture was evacuated under nitrogen and circulated three times, then stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.36 g, with a yield of 63.5%. MS (ASAP) = 354.09.
[0084] Synthesis of intermediate 2c-1: 2a (20 g, 94.78 mmol), 2b-1 (33.57 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated under nitrogen and circulated three times. The reaction mixture was stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15 g, a yield of 64%. MS (ASAP) = 440.15.
[0085] Synthesis of Compound 10: Intermediate 2c-1 (33.92 g, 77 mmol), intermediate 1d (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 7 g, a yield of 35%. MS (ASAP) = 759.3.
[0086] Example 3
[0087] An organic light-emitting compound, the structure of which is shown in compound 20; its synthetic route is as follows:
[0088]
[0089] The synthesis of intermediate 1c and intermediate 1d is the same as in Example 1.
[0090] Raw materials 1a, 1b, 2a, z2 and z3 (CAS: 1135916-40-3) can be purchased directly.
[0091] Synthesis of intermediate 2b-2: In a dry two-necked flask, z3 ((9-phenyl-9H-carbazole-3,6-diyl)diboronic acid, 31.37 g, 94.78 mmol), z2 (1-bromonaphthalene, 19.63 g, 94.78 mmol), and tetraphenylphosphine palladium (2.26 g, 1.96 mmol) were added, followed by 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane. The mixture was evacuated under nitrogen and circulated three times, then stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.36 g, a yield of 63.5%. MS (ASAP) = 413.16.
[0092] Synthesis of intermediate 2c-2: 2a (20 g, 94.78 mmol), 2b-2 (39.17 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15 g, with a yield of 70%. MS (ASAP) = 499.22.
[0093] Synthesis of Compound 20: Intermediate 2c-2 (38.47 g, 77 mmol), intermediate 1d (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 8 g, a yield of 60%. MS (ASAP) = 818.37.
[0094] Example 4
[0095] An organic light-emitting compound, the structure of which is shown in compound 21; its synthetic route is as follows:
[0096]
[0097] The synthesis of intermediates 1c and 1d is the same as in Example 1.
[0098] Raw materials 1a, 1b, 2a, z4 (CAS: 2697709-54-7) and z5 (CAS: 13922-41-3) can be purchased directly.
[0099] Synthesis of intermediate Z6: Z4 (2-bromo-6-chloro-9-phenyl-9H-carbazole, 33.80 g, 94.78 mmol), Z5 (1-naphthoboric acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.3 g, with a yield of 73.6%.
[0100] Synthesis of intermediate 2b-3: Z6 (15.80 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After about 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. Then, the temperature was raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for about 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give a total of 5.86 g of solid, with a yield of 71.5%. MS (ASAP) = 413.16.
[0101] Synthesis of intermediate 2c-3: 2a (20 g, 94.78 mmol), 2b-3 (39.17 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 16 g, with a yield of 74.5%. MS (ASAP) = 499.22.
[0102] Synthesis of Compound 21: Intermediate 2c-3 (38.47 g, 77 mmol), intermediate 1d (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 10 g, a yield of 64%. MS (ASAP) = 818.37.
[0103] Example 5
[0104] An organic light-emitting compound, the structure of which is shown in compound 25; its synthetic route is as follows:
[0105]
[0106] Raw materials 1a, 2a-1 (CAS: 114744-50-2) and 2b can be purchased directly.
[0107] Synthesis of intermediate 1c-1: 1a (1,3-dibromo-2-iodobenzene, 10.85 g, 30 mmol), 2b (4-(1-naphthyl)phenylboronic acid, 7.44 g, 30 mmol), potassium carbonate (8.28 g, 60 mmol), and tetra(triphenylphosphine)palladium (1.04 g, 0.9 mmol) were weighed and added to a two-necked flask. A mixed solvent of toluene and methanol was added, and the mixture was purged with nitrogen three times. The mixture was heated to 90 °C and stirred overnight. After the reaction solution cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulfate, and the organic solvent was removed by vacuum distillation. The product 1c-1 was separated by silica gel column chromatography, yielding 7.5 g of the target product 1c-1 (60% yield). MS (ASAP) = 435.95.
[0108] Synthesis of intermediate 1d-1: 1c-1 (6.57 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After approximately 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another 30 minutes. The temperature was then raised to room temperature, and the reaction was continued for 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for approximately 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to obtain 5.3 g of 1d-1 in 75% yield. MS (ASAP) = 398.07.
[0109] Synthesis of intermediate 2c-4: 2a-1 (20 g, 94.78 mmol), 2b (23.51 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.5 g, a yield of 65.4%. MS (ASAP) = 334.16.
[0110] Synthesis of Compound 25: Intermediate 2c-4 (25.75 g, 77 mmol), intermediate 1d-1 (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 8.5 g, a yield of 45%. MS (ASAP) = 653.31.
[0111] Example 6
[0112] An organic light-emitting compound, the structure of which is shown in compound 33; its synthetic route is as follows:
[0113]
[0114] The synthesis of intermediates 1c-1 and 1d-1 is the same as in Example 5.
[0115] Raw materials 1a, 2a-2 (CAS:114744-51-3), 2b, z2 and z7 (CAS:1222008-13-0) can be purchased directly.
[0116] Synthesis of intermediate 2b-4: Intermediates Z7 (dibenzo[b,d]furan-2,8-dimethyldiboronic acid, 24.25 g, 94.78 mmol), Z2 (1-bromonaphthidine, 19.63 g, 94.78 mmol), and tetraphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.5 g, a yield of 65.1%. MS (ASAP) = 338.11.
[0117] Synthesis of intermediate 2c-5: 2a-2 (20 g, 94.78 mmol), 2b-4 (32.08 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.2 g, a yield of 65%. MS (ASAP) = 424.17.
[0118] Synthesis of Compound 33: Intermediate 2c-5 (38.47 g, 77 mmol), intermediate 1d-1 (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 7.5 g, a yield of 40%. MS (ASAP) = 743.32.
[0119] Example 7
[0120] An organic light-emitting compound, the structure of which is shown in compound 45; its synthetic route is as follows:
[0121]
[0122] The synthesis of intermediates 1c-1 and 1d-1 was the same as in Example 5, and the synthesis of intermediate 2b-2 was the same as in Example 3.
[0123] Raw materials 1a, 2a-2, 2b, z2 and z3 can be purchased directly.
[0124] Synthesis of intermediate 2c-6: 2a-2 (20 g, 94.78 mmol), 2b-2 (39.17 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated under nitrogen and circulated three times. The reaction mixture was stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.5 g, a yield of 65%. MS (ASAP) = 499.22.
[0125] Synthesis of Compound 45: Intermediate 2c-6 (38.47 g, 77 mmol), intermediate 1d-1 (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 8.5 g, a yield of 49%. MS (ASAP) = 818.37.
[0126] Example 8
[0127] An organic light-emitting compound, the structure of which is shown in compound 46; its synthetic route is as follows:
[0128]
[0129] The synthesis of intermediates 1c-1 and 1d-1 is the same as in Example 5.
[0130] Raw materials 1a, 2a, 2b, z5 and z8 (CAS: 2417535-30-7) can be purchased directly.
[0131] Synthesis of intermediate Z9: Z8 (5-bromo-3-chloro-9-phenyl-9H-carbazole, 33.80 g, 94.78 mmol), Z5 (1-naphthoboric acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.8 g, with a yield of 73.9%.
[0132] Synthesis of intermediate 2b-5: Z9 (6.12 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After about 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. Then, the temperature was raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for about 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give a total of 5.86 g of solid, with a yield of 71.5%. MS (ASAP) = 413.16.
[0133] Synthesis of intermediate 2c-7: 2a (20 g, 94.78 mmol), 2b-5 (39.17 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.8 g, a yield of 67%. MS (ASAP) = 499.22.
[0134] Synthesis of Compound 46: Intermediate 2c-7 (38.47 g, 77 mmol), intermediate 1d-1 (30.75 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 9.2 g, a yield of 51%. MS (ASAP) = 818.37.
[0135] Example 9
[0136] An organic light-emitting compound, the structure of which is shown in compound 55; its synthetic route is as follows:
[0137]
[0138] Raw materials 2a, z5, z10 (CAS: 2356108-20-6) and z12 (CAS: 617707-33-2) can be purchased directly.
[0139] Synthesis of intermediate Z11: In a dry two-necked flask, Z10 (2-bromo-5-chloro-9,9-dimethyl-9H-fluorene, 30.68 g, 94.78 mmol), Z5 (1-naphthoboric acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.8 g, with a yield of 65.6%.
[0140] Synthesis of intermediate 2b-6: Z11 (5.56 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After about 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. Then, the temperature was raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for about 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give a total of 6.32 g of solid, with a yield of 75%. MS (ASAP) = 380.19.
[0141] Synthesis of intermediate 2c-8: 2a (20 g, 94.78 mmol), 2b-6 (36.04 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated under nitrogen and circulated three times. The reaction mixture was stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.6 g, a yield of 64.3%. MS (ASAP) = 467.27.
[0142] Synthesis of intermediate 1e: In a dry two-necked flask, z12 (3,6-dibromodibenzo[b,d]furan, 30.90 g, 94.78 mmol), z5 (1-naphthoboronic acid, 16.30 g, 94.78 mmol), and tetraphenylphosphine palladium (2.26 g, 1.96 mmol) were added, followed by 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.3 g, with a yield of 65.6%.
[0143] Synthesis of Compound 55: Intermediate 2c-8 (36.01 g, 77 mmol), intermediate 1e (28.74 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 9.8 g, a yield of 55.3%. MS (ASAP) = 759.35.
[0144] Example 10
[0145] An organic light-emitting compound, the structure of which is shown in compound 67; its synthetic route is as follows:
[0146]
[0147] The synthesis of intermediates 2b-6 and 2c-8 is the same as in Example 9.
[0148] Raw materials 2a, z5, z10 and z13 (CAS: 1507368-41-3) can be purchased directly.
[0149] Synthesis of intermediate 1e-1: In a dry two-necked flask, z13 (2,6-dibromo-9-phenyl-9H-carbazole, 38.01 g, 94.78 mmol), z5 (1-naphthoboric acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added, followed by 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 13.8 g, with a yield of 64.6%.
[0150] Synthesis of Compound 67: Intermediate 2c-8 (36.01 g, 77 mmol), intermediate 1e-1 (30.88 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 13.6 g, a yield of 60.3%. MS (ASAP) = 818.37.
[0151] Example 11
[0152] An organic light-emitting compound, the structure of which is shown in compound 80; its synthetic route is as follows:
[0153]
[0154] Raw materials 2a, z5, z14 (CAS:32316-92-0), z10 and z15 (CAS:67019-91-4) can be purchased directly.
[0155] Synthesis of intermediate Z16: Z10 (2-bromo-5-chloro-9,9-dimethyl-9H-fluorene, 30.68 g, 94.78 mmol), Z14 (2-naphthoboric acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 14.6 g, with a yield of 64.3%.
[0156] Synthesis of intermediate 2b-7: Z16 (5.32 g, 15 mmol) was dissolved in anhydrous tetrahydrofuran, cooled to -78 °C, and butyllithium (1.6 M, 9.4 mL) was slowly added. After about 0.5 hours, acetone (15 mmol) was added dropwise to the reaction flask, and the reaction was continued at this temperature for another half hour. Then, the temperature was raised to room temperature, and the reaction was continued for another 8 hours. The solvent was removed under reduced pressure, and hydrochloric acid and acetic acid were added. The mixture was refluxed for about 2 hours. The temperature was lowered to room temperature, and deionized water was added. The mixture was then extracted with ethyl acetate. After concentration, the mixture was separated by silica gel column chromatography, and the solvent was removed to give a total of 6.42 g of solid, with a yield of 75.4%. MS (ASAP) = 364.16.
[0157] Synthesis of intermediate 1e-2: Intermediate Z15 (3,7-dibromodibenzo[b,d]furan, 30.90 g, 94.78 mmol), Z5 (1-naphthoboronic acid, 16.30 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.3 g, with a yield of 65.9%.
[0158] Synthesis of intermediate 2c-9: 2a (20 g, 94.78 mmol), 2b-7 (34.52 g, 94.78 mmol), and tetra-triphenylphosphine palladium (2.26 g, 1.96 mmol) were added to a dry two-necked flask. Then, 200 mL of 2M potassium carbonate aqueous solution and 500 mL of 1,4-dioxane were added. The mixture was evacuated and purged with nitrogen three times, and stirred overnight at 80 °C. After the reaction was complete, the reaction solution was cooled to room temperature, 300 mL of water was added, and the mixture was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 10:1). The concentrate yielded 15.3 g, a yield of 65.9%. MS (ASAP) = 451.23.
[0159] Synthesis of Compound 80: Intermediate 2c-9 (34.77 g, 77 mmol), intermediate 1e-2 (28.74 g, 77 mmol), tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol), tri-tert-butylphosphine (0.56 g, 2 mmol), and sodium tert-butoxide (6.73 g, 70 mmol) were accurately weighed and added to a 250 mL two-necked flask. 100 mL of anhydrous toluene was added to dissolve the compounds. After three cycles of purging, the mixture was heated to reflux overnight. After the reaction was complete, the mixture was cooled to room temperature, quenched with a small amount of water, concentrated, and then subjected to silica gel column chromatography (n-hexane:dichloromethane = 3:1). The concentrate yielded 12.3 g, a yield of 60.3%. MS (ASAP) = 743.32.
[0160] Example 12
[0161] A schematic diagram of an organic electroluminescent device is shown below. Figure 1 As shown, it includes, in sequence: anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, electron transport layer, electron injection layer, and cathode.
[0162] The fabrication process of this organic electroluminescent device includes the following steps:
[0163] (1) Substrate treatment: Transparent ITO glass was used as the substrate material for device fabrication. It was first ultrasonically treated with 5% ITO cleaning solution for 30 min, then ultrasonically washed sequentially with distilled water (twice), acetone (twice), and isopropanol (twice). Finally, the ITO glass was stored in isopropanol. Before each use, the surface of the ITO glass was carefully wiped with acetone-soaked cotton balls and isopropanol-soaked cotton balls.
[0164] After rinsing with isopropanol and drying, the device was then treated with plasma for 5 minutes before use. Subsequent fabrication of the device was completed using a combination of spin coating and vacuum evaporation processes.
[0165] (2) Preparation of hole injection layer, hole transport layer and electron blocking layer: Hole injection layer, hole transport layer and electron blocking layer are prepared by vapor deposition process. When the vacuum degree of the vacuum vapor deposition system reaches 5×10 -4 Evaporation begins when the pressure is below Pa. The deposition rate is monitored by a SAINS film thickness gauge. Hole injection layer, hole transport layer and electron blocking layer are sequentially deposited on the surface of ITO electrode using vacuum evaporation process. The deposition rate of hole injection material, hole transport material and electron blocking material is 0.5 Å / s.
[0166] (3) Preparation of the light-emitting layer: The light-emitting layer is prepared by vapor deposition process. When the vacuum degree of the vacuum vapor deposition system reaches 5×10 - 4 Evaporation begins when the pressure is below Pa, and the deposition rate is monitored by a SAINS film thickness gauge. The luminescent layer is deposited on the hole transport layer using a vacuum evaporation process, and the deposition rate of the luminescent layer material is 0.5 Å / s.
[0167] (4) Fabrication of electron transport layer, electron injection layer and metal electrode: The electron transport layer, electron injection layer and metal electrode are fabricated by vapor deposition process. When the vacuum degree of the vacuum deposition system reaches 5×10 -4 Vapor deposition begins when the pressure is below Pa, and the deposition rate is monitored by a SAINS film thickness gauge. An electron transport layer, an electron injection layer, and a metal electrode are sequentially deposited on the luminescent layer using a vacuum evaporation process. The deposition rate of the electron transport layer is 0.5 Å / s, the electron injection layer is 0.1 Å / s, and the metal electrode is 5 Å / s.
[0168] In this structure, ITO glass serves as the transparent substrate, HATCN as the hole injection layer material, TAPC as the hole transport layer material, TCTA as the electron blocking layer material, TPBi as the electron transport layer material, LiQ as the electron injection layer material, and Al as the metal cathode. The organic electroluminescent device structure is [ITO / HATCN (5nm) / TAPC (40 nm) / TCTA (5 nm) / emitting layer (25 nm) / TPBi (40 nm) / LiQ (1 nm) / Al (100 nm)].
[0169] In this process, HOST is used as the host material in the light-emitting layer, and compound 1 of this application is used as the guest material for light emission (with contents of 2 wt%, 8 wt%, and 10 wt%, respectively), ultimately yielding organic electroluminescent devices D1-D3.
[0170] Example 13
[0171] An organic electroluminescent device was prepared using the same method as the device in Example 12, except that compound 21 was used as the luminescent guest material, with contents of 2 wt%, 8 wt%, and 10 wt%, respectively. Organic electroluminescent devices D4-D6 were ultimately obtained.
[0172] Example 14
[0173] An organic electroluminescent device was prepared using the same method as the device in Example 12, except that compound 25 was used as the luminescent guest material, with contents of 2 wt%, 8 wt%, and 10 wt%, respectively. Organic electroluminescent devices D7-D9 were ultimately obtained.
[0174] Example 15
[0175] An organic electroluminescent device was prepared using the same method as the device in Example 12, except that compound 46 was used as the luminescent guest material, with contents of 2 wt%, 8 wt%, and 10 wt%, respectively. Organic electroluminescent devices D10-D12 were ultimately obtained.
[0176] Comparative Example 1
[0177] An organic electroluminescent device is prepared using the same method as the device in Example 12, except that compound complex1 is used as the luminescent guest material, with contents of 2 wt%, 8 wt%, and 10 wt%, respectively. Organic electroluminescent devices C1-C3 are finally obtained.
[0178] Comparative Example 2
[0179] An organic electroluminescent device was prepared using the same method as the device in Example 12, except that compound complex2 was used as the luminescent guest material, with contents of 2 wt%, 8 wt%, and 10 wt%, respectively. Organic electroluminescent devices C4-C6 were ultimately obtained.
[0180] Organic electroluminescent devices D1-D12 prepared in Examples 12-15 and organic electroluminescent devices C1-C6 prepared in Comparative Examples 1-2 were tested. The current, voltage, brightness, and emission spectrum characteristics of the devices were simultaneously tested using a PR655 spectral scanning luminance meter and a Keithley K 2400 digital source meter system. Performance testing was performed after device packaging. The test results are shown in Table 1.
[0181] Table 1
[0182]
[0183] The performance data of the organic electroluminescent devices show that the organic electroluminescent devices prepared using the compounds provided in this application exhibit high efficiency at high brightness and good device stability, indicating that the organic electroluminescent devices of this application have high external quantum efficiency and small device efficiency roll-off.
[0184] The above description is merely a preferred embodiment of this application. This application is not limited to the above-described embodiments. Any embodiment that achieves the technical effect of this application using the same means should fall within the protection scope of this application. Within the protection scope of this application, the technical solutions and / or implementation methods can have various modifications and variations.
Claims
1. An organic light-emitting compound, characterized in that, The structures of the organic light-emitting compounds are shown in any one of compounds 1, 21, 25, and 46: 。 2. An organic electroluminescent composition, characterized in that, It includes a host material and a luminescent guest material, wherein the luminescent guest material includes the organic luminescent compound as described in claim 1.
3. The organic electroluminescent composition according to claim 2, characterized in that, The content of the main material is 90wt%-98wt%, and the content of the luminescent guest material is 2wt%-10wt%.
4. An organic electroluminescent device, characterized in that, It includes an anode and a cathode, and further includes a light-emitting layer between the anode and the cathode, the light-emitting layer comprising the organic electroluminescent composition as described in claim 2 or 3.
5. The organic electroluminescent device according to claim 4, characterized in that, In order, they include: The anode, hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, electron transport layer, electron injection layer, and cathode.
6. A display device, characterized in that, Including the organic electroluminescent device as described in claim 4 or 5.