A boron-containing organic compound and its application

Abstract

The present invention relates to a boron-containing organic compound and its application, belonging to the field of semiconductor technology. The present invention provides a compound having a structure as shown in general formula (1): the compound of the present invention has a narrow half-width. When used as a dopant material in a light-emitting layer material of an OLED light-emitting device, the current efficiency of the device is significantly improved, and the luminous color purity and device life are also greatly improved. The boron-containing organic compound of the present invention is used as a light-emitting layer dopant material to enable the device to have good photoelectric properties.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and in particular to a boron-containing organic compound and application thereof. Background Art

[0002] Traditional fluorescent doping materials, limited by early technology, can only utilize the 25% of singlet excitons formed by electrical excitation to emit light. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lagging behind the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center that enhances intersystem crossing, can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, achieving a device internal quantum efficiency of 100%. However, the high cost of most phosphorescent materials, poor material stability, low color purity, and severe device efficiency roll-off have limited their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are being placed on color rendering standards. In addition to being efficient and stable, luminescent materials also need to have a narrower half-width to improve the color purity of the device's luminescent color. Fluorescent doping materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doping materials have achieved a phased breakthrough, and the half-width of boron-based materials can be reduced to below 30nm. However, research in the green light region, to which the human eye is more sensitive, has mainly focused on phosphorescent doping materials. However, their luminescent peak shape is difficult to narrow through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping materials with narrow half-width.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials with fluorescent doping materials, uses triplet exciton-sensitizing materials as exciton-sensitizing media, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width luminescence. Such materials are used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006 A disclose a TADF material with a difference between the lowest singlet state and the lowest triplet state energy level of less than or equal to 0.2eV as the main body, and a boron-containing material as the doping luminescent layer combination technology; CN 110492005 A and CN 110492009 A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the Invention

[0006] To address the aforementioned issues in the prior art, the present inventors have provided a boron-containing organic compound and its application. The compound has a narrow half-width (FWHM) and can be used as a dopant material in the light-emitting layer of an organic electroluminescent device, thereby improving the device's luminescent color purity and lifetime.

[0007] A boron-containing organic compound, the structure of which is shown in general formula (1):

[0008]

[0009] R1-R 26 Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C3-C10 heterocycloalkyl group, a substituted or unsubstituted C1-C10 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group;

[0010] R1-R 26 Any group in the group can be connected to the adjacent group to form a ring;

[0011] The substituents for the above-mentioned substitutable groups are selected from deuterium, tritium, halogen atoms, cyano groups, C1-C 10 Alkyl, deuterium or tritium substituted C1~C 10 Alkyl, C6~C 30 Aryl, deuterium or tritium substituted C6~C 30 Aryl, C5~C 30 Heteroaryl, deuterium or tritium substituted C2~C 30 Any of heteroaryl groups;

[0012] The heteroatoms in the heteroaryl group are optionally selected from one or more of oxygen, sulfur and nitrogen.

[0013] Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (2) to (9):

[0014]

[0015]

[0016] Among them, R1-R8, R 10 、R 13 、R 16 、R 19 、R 22 、R 25 The definition of is the same as above.

[0017] Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (10) to (13):

[0018]

[0019] Among them, R 10 、R 13 、R 16 、R 19 、R 22 、R 25 The definition of is the same as above.

[0020] Preferably, the structure of the boron-containing organic compound is as shown in any one of the general formulas (14) to (15):

[0021]

[0022] Among them, R9-R 26 The definition of is the same as above.

[0023] Preferably, R1-R 26wherein each independently represents hydrogen, deuterium, tritium, a fluorine atom, a trifluoromethyl group, an adamantyl group, a methyl group, a deuterated methyl group, a trited methyl group, an ethyl group, a deuterated ethyl group, a trited ethyl group, an isopropyl group, a deuterated isopropyl group, a trited isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a trited tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a trited cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a trited cyclohexyl group, a methoxy group, a deuterated methoxy group, a trited methoxy group, an ethoxy group, a deuterated ethoxy group, a trited ethoxy group, an isopropoxy group, a deuterated isopropoxy group, a trited isopropoxy group, or a tert-butyl group. phenyl, deuterated tert-butyloxy, tritiated tert-butyloxy, phenoxy, deuterated phenoxy, tritiated phenoxy, naphthoxy, deuterated naphthoxy, tritiated naphthoxy, anthracenoxy, deuterated anthracenoxy, tritiated anthracenoxy, phenanthrenoxy, deuterated phenanthrenoxy, tritiated phenanthrenoxy, diphenylamino, deuterated diphenylamino, tritiated diphenylamino, methyl-substituted diphenylamino, isopropyl-substituted diphenylamino, tert-butyl-substituted diphenylamino, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, deuterated terphenyl, tritiated terphenyl biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tritiated methyl-substituted phenyl, tritiated ethyl-substituted phenyl, tritiated isopropyl-substituted phenyl, tritiated tert-butyl-substituted phenyl, tritiated methyl-substituted biphenyl, tritiated ethyl-substituted biphenyl, tritiated isopropyl-substituted biphenyl or tritiated tert-butyl-substituted biphenyl.

[0024] Preferably, the substituents for the above-mentioned substitutable groups are selected from one or more of deuterium, tritium, adamantyl, methyl, deuterated methyl, trited methyl, ethyl, deuterated ethyl, trited ethyl, isopropyl, deuterated isopropyl, trited isopropyl, tert-butyl, deuterated tert-butyl, trited tert-butyl, isobutyl, phenyl, deuterated phenyl, trited phenyl, biphenyl, deuterated biphenyl, trited biphenyl, naphthyl, anthracenyl, phenanthrenyl, pyridyl, quinolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, azadimethylfluorenyl, and azadiphenylfluorenyl.

[0025] Preferably, R1-R 26 They are expressed independently as:

[0026] hydrogen atoms, Any one of them.

[0027] Preferably, the specific structural formula of the boron-containing organic compound is any one of the following structures:

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] An organic light-emitting device comprises a cathode, an anode and a functional layer, wherein the functional layer is located between the cathode and the anode, and the functional layer of the organic light-emitting device comprises any one of the above-mentioned boron-containing organic compounds.

[0046] Preferably, the doping material of the light-emitting layer is any of the boron-containing organic compounds described above.

[0047] The light-emitting layer comprises a first host material, a second host material and a doping material. Preferably, at least one of the first host material and the second host material is a TADF material, and the doping material is any of the above-mentioned boron-containing organic compounds.

[0048] The light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material. Preferably, the exciton-sensitizing material is a complex containing a metal element, and the doping material is any of the above-mentioned boron-containing organic compounds.

[0049] Compared with the prior art, the present invention has the following beneficial technical effects:

[0050] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields.

[0051] (2) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as the second host, which can effectively improve the efficiency and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0052] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0053] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.

[0054] Figure 2 For compound 16 1 HNMR spectrum;

[0055] Figure 3 This is the PL spectrum of compound 16 in toluene solution. DETAILED DESCRIPTION

[0056] Synthesis of intermediate B-1:

[0057]

[0058] The raw material A-6 (5 g) was dissolved in acetonitrile (50 mL), and then NBS (6.9 g) was dissolved in acetonitrile (50 mL) and slowly added. The reaction solution was stirred at 0°C for 30 minutes. The reaction solution was directly concentrated. The residue was rinsed with petroleum ether and filtered and concentrated to obtain intermediate c-1 (90%) as a black liquid. LC-MS: Measured value: 214.10 ([M+H] + ), theoretical value: 213.02.

[0059] Intermediate c-1 (5.3 g) was dissolved in NMP (25 mL), and then CuCN (2.4 g) was added. The reaction mixture was stirred at 200°C for 3 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (3 L) and filtered. The filtrate was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. Intermediate c-2 (90%) was obtained as a black liquid. LC-MS: Measured value: 161.10 ([M+H] + ), theoretical value: 160.10.

[0060] Intermediate c-2 (5 g) was dissolved in methanol (20 mL) and ethanol (3 mL), and then an aqueous sodium hydroxide solution (20 mL, 10 mol / L) was added. The reaction solution was stirred at 100°C for 16 h. The reaction solution was concentrated, and the residue was adjusted to pH 7 with concentrated hydrochloric acid and filtered. The filter cake was dissolved in ethyl acetate and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give intermediate c-3 (90%) as a black solid. LC-MS: Measured value: 180.10 ([M+H] + ), theoretical value: 179.09.

[0061] Intermediate c-3 (5 g) was dissolved in methanol (30 mL) and DMF (0.3 mL), and then SOCl2 (2.4 mL) was slowly added. The reaction solution was stirred at 90°C for 16 h. The reaction solution was concentrated, and the residue was adjusted to pH 7 with aqueous potassium carbonate solution, dissolved in ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 30:1) to obtain intermediate c-4 (95%) as a black solid. LC-MS: Measured value: 194.10 ([M+H] + ), theoretical value: 193.11.

[0062] Intermediate c-4 (5.5 g) and sodium hydride (1.9 g) were dissolved in anhydrous tetrahydrofuran (THF) (100 ml) under nitrogen and refluxed for 5 h. After cooling to room temperature, the reaction solution was slowly added dropwise with a large amount of 1 M glacial hydrochloric acid solution, filtered, and washed with dichloromethane to obtain intermediate c-5 (100%) as a yellow solid. LC-MS: Measured value: 323.20 ([M+H] + ), theoretical value: 322.17. Intermediate c-5 (40 g) was dissolved in chloroform (1000 mL), phosphorus pentachloride (80 g) was added in an ice-water bath, nitrogen was protected, the temperature was raised to room temperature, and the reaction was refluxed overnight. Cool, filter, spin dry the solvent, and purify by column chromatography (PE:EA=20:1) to obtain intermediate c-6 (45%) as a yellow solid. LC-MS: Measured value: 359.10 ([M+H] + ), theoretical value: 358.10.

[0063] Intermediate c-6 (21 g) was dissolved in tetrahydrofuran (THF) (300 mL), and zinc powder (38 g) was added. Under nitrogen protection, trifluoroacetic acid (42 mL) was slowly added under ice bath and the mixture was allowed to warm to room temperature for 16 h. Filter, extract with EA, dry and spin dry. The crude product was washed with petroleum ether and ethyl acetate to obtain intermediate B-1 (77%) as a light yellow solid. LC-MS: Measured value: 291.20 ([M+H] + ), theoretical value: 290.18.

[0064] Synthesis of intermediate B-2:

[0065]

[0066] The synthesis method of intermediate B-2 is similar to that of intermediate B-1, except that raw material A-6 is replaced by raw material A-7. Intermediate B-2, LC-MS: Measured value: 319.36 ([M+H] + ), theoretical value: 318.21.

[0067] Synthesis of intermediate B-3:

[0068]

[0069] Raw material A-8 (30 g) was dissolved in acetic acid (200 ml), heated to 60°C and refluxed, A-9 (22.4 g) was added dropwise, and the mixture was refluxed for 8 h. After cooling to room temperature, aqueous NaOH solution (100 mL, 10 mol / L) was added to make the resulting mixture alkaline. The mixture was then extracted with water and ethyl acetate, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane / ethyl acetate = 30:1) to obtain intermediate e-1. LC-MS: Measured value: 228.06 ([M+H] + ), theoretical value: 227.17.

[0070] Intermediate e-1 (34.1 g) was dissolved in toluene (300 ml) under a nitrogen atmosphere and cooled to -10°C. A 1.6 M methyllithium toluene solution (150 ml) was slowly added dropwise and allowed to react at -10°C for 3 hours. Water was slowly added until the solution became unreactive. The mixture was then extracted with water and ethyl acetate, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane / ethyl acetate = 30:1) to obtain Intermediate B-3. LC-MS: Measured value: 244.15 ([M+H] + ), theoretical value: 243.20.

[0071] Synthesis of intermediate B-4:

[0072]

[0073] To a three-necked flask, raw material A-10 (1.6 g), raw material A-11 (1.24 g), 50 mL of toluene, 16 mL of ethanol, potassium carbonate (2.1 g), and Pd(PPh3)4 (0.23 g) were added, and nitrogen was passed through. The reaction was refluxed for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and water was added to quench the reaction. The mixture was extracted three times with ethyl acetate, and the organic phases were combined, then dried over anhydrous sodium sulfate, filtered, and concentrated to obtain a crude product. Intermediate B-4 was obtained by purification through recrystallization (ethyl acetate / petroleum ether). LC-MS: Measured value: 395.34 ([M+H] + ), theoretical value: 394.11.

[0074] Synthesis of intermediate B-5:

[0075]

[0076] The synthesis method of intermediate B-5 is similar to that of intermediate B-4, except that raw material A-11 is replaced by raw material A-12. LC-MS: Measured value: 327.19 ([M+H] + ), theoretical value: 326.05.

[0077] Example 1 Synthesis of Compound 16:

[0078]

[0079] Add raw material A-4 (9.6 g), raw material A-2 (9.85 g), potassium carbonate (6.9 g), and N-methylpyrrolidone (200 ml) to a two-necked flask and stir at 170°C for 10 h under nitrogen. After cooling, extract with ethyl acetate / salt water, dry, and filter through a PE column to obtain intermediate f-1 as a colorless oily liquid. LC-MS: Measured value: 374.26 ([M+H] + ), theoretical value: 373.08.

[0080] Add raw material A-1 (10 g) and cesium carbonate (40 g) to a two-necked flask, add anhydrous DMF (200 ml) under nitrogen protection, stir at room temperature for 30 min, add intermediate f-1 (37.3 g) under nitrogen protection, stir at 140°C under nitrogen protection for 15 h, filter, wash with water, dry, and pass through a PE:EA = 20:1 column to obtain intermediate f-2 as a white solid. LC-MS: Measured value: 913.40 ([M+H] + ), theoretical value: 912.24.

[0081] Intermediate f-2 (45.6 g) was added to a two-necked flask, and tert-butylbenzene (300 ml) was added under nitrogen protection. The temperature was lowered to -40°C, and a 2.5 M n-butyllithium pentane solution (250 ml) was added dropwise. The temperature was raised to 70°C and stirred for 2 h. The temperature was lowered to -40°C, and boron tribromide (12 ml) was added. The temperature was raised to room temperature and stirred for 30 min. The temperature was lowered to 0°C, and N, N-diisopropylethylamine (35 ml) was added. The temperature was raised to 130°C and stirred for 12 h. The mixture was cooled, extracted, and the solvent was removed. The crude product was added with dichloromethane, heated to reflux for 30 min, and filtered while hot to obtain compound 16 in a yield of about 12%.

[0082] The preparation methods of Examples 2-9 are similar to those of Example 1, and the reaction equivalents are the same as those for the preparation of Compound 16 in Example 1. The difference lies in the different raw materials and intermediates used. The structural formulas of the raw materials, intermediates, and products are listed in the following table, and the test results are also listed in Table 1 below.

[0083] Table 1

[0084]

[0085]

[0086]

[0087] In order to perform structural analysis on the compounds prepared in Examples 1 to 9, the molecular weights were measured using LC-MS. The results are shown in Table 2:

[0088] Table 2

[0089]

[0090] Note: FWHM (full width at half maximum) is measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state.

[0091] The H NMR data of the compound prepared above are shown in Table 3;

[0092] Table 3

[0093]

[0094]

[0095] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device examples 1-9 and device comparative examples 1-2. The device manufacturing processes of device examples 2-9 and device comparative examples 1-2 are identical to those of device example 1, and the same substrate materials and electrode materials are used. The film thickness of the electrode materials is also consistent. The only difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Table 4 and Table 6, respectively.

[0096] Device Example 1

[0097] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness 150nm) is washed, that is, washed with a detergent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the transparent ITO surface. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 are evaporated with a thickness of 10nm as the hole injection layer 3 using a vacuum evaporation device, with the mass ratio of HT-1 to HI-1 being 97:3. HT-1 is then evaporated with a thickness of 60nm as the hole transport layer 4. EB-1 is then evaporated with a thickness of 30nm as the electron blocking layer 5. After the above electron blocking material evaporation is completed, the light-emitting layer 6 of the OLED light-emitting device is produced, using CBP as the host material and compound 16 as the dopant material, with the mass ratio of CBP to compound 16 being 97:3, and the light-emitting layer film thickness being 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick layer. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0098] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device examples 10-18 and device comparative examples 2-4. The device manufacturing processes of device examples 11-18 and device comparative examples 2-4 are identical to those of device example 10, and the same substrate materials and electrode materials are used. The film thickness of the electrode materials is also consistent. The only difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 5 and 6, respectively.

[0099] Device Example 10

[0100] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (150 nm thick) is washed sequentially with a detergent (Semiclean M-L20), then washed with pure water, dried, and then subjected to UV-ozone cleaning to remove organic residues from the transparent ITO surface. On the washed ITO anode layer 2, a 10 nm thick layer of HT-1 and HI-1 is deposited using a vacuum evaporation apparatus as the hole injection layer 3. The weight ratio of HT-1 to HI-1 is 97:3. HT-1 is then deposited to a thickness of 60 nm as the hole transport layer 4. EB-1 is then deposited to a thickness of 30 nm as the electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. The structure comprises CBP and DMAC-BP as dual host materials, compound 16 as the dopant, and a weight ratio of CBP, DMAC-BP, and compound 16 of 67:30:3. The light-emitting layer thickness is 30 nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick layer. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0101] The molecular structure formula of the relevant materials is shown below:

[0102]

[0103] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known drive circuit, and the device's current efficiency and lifetime were measured. Examples and comparative examples of devices prepared using the same method are shown in Tables 4 and 5; the test results for the current efficiency and lifetime of the resulting devices are shown in Table 6.

[0104] Table 4

[0105]

[0106] Table 5

[0107]

[0108]

[0109] Table 6

[0110]

[0111]

[0112] Note: Current efficiency and luminescence peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the lifespan test system was an EAS-62C OLED device lifespan tester from Japan System Giken Co., Ltd.; LT95 refers to the time it takes for the device's luminance to decay to 95%; all data are measured at 10 mA / cm 2 Next test.

[0113] It can be seen from the device data results in Table 6 that, compared with device comparison examples 1-4, the current efficiency and device life of the organic light-emitting device of the present invention are greatly improved relative to OLED devices of known materials; when using TADF material as the second main body, the device efficiency is significantly improved compared to that of a single main body.

[0114] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A boron-containing organic compound, characterized in that: The structure of the boron-containing organic compound is shown in general formula (1): R1-R8 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted C1-C10 alkyl group; R9-R 26 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, or a deuterated tert-butyl-substituted biphenyl group; The substituent for the above-mentioned substitutable group may be selected from any one of deuterium, a halogen atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, and an isobutyl group.

2. The boron-containing organic compound according to claim 1, wherein: The structure of the boron-containing organic compound is shown in any one of the general formulas (2) to (9): Among them, R1-R8, R 10 、R 13 、R 16 、R 19 、R 22 、R 25 The definition is the same as that in claim 1.

3. The boron-containing organic compound according to claim 1, wherein: The structure of the boron-containing organic compound is shown in any one of the general formulas (11) to (13): Among them, R 10 、R 13 、R 16 、R 19 、R 22 、R 25 The definition is the same as that in claim 1.

4. The boron-containing organic compound according to claim 1, wherein: The structure of the boron-containing organic compound is shown in general formula (15): Among them, R9-R 26 The definition is the same as that in claim 1.

5. A boron-containing organic compound, characterized in that: The structure of the boron-containing organic compound is shown in general formula (14): Among them, R9-R 26 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, or a deuterated tert-butyl-substituted biphenyl group; The substituent for the above-mentioned substitutable group may be selected from any one of deuterium, a halogen atom, a cyano group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, and an isobutyl group.

6. The boron-containing organic compound according to claim 5, characterized in that: The structure of the boron-containing organic compound is shown in general formula (10): Among them, R 10 、R 13 、R 16 、R 19 、R 22 、R 25 The definition is the same as that in claim 5.

7. The boron-containing organic compound according to claim 1, characterized in that: R1-R8 in the general formula (1) are independently hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl; R9-R 26 Each of the following independently represents hydrogen, deuterium, a fluorine atom, a trifluoromethyl group, an adamantyl group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted Phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl.

8. The boron-containing organic compound according to claim 2, wherein: R1-R8 are independently hydrogen, deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl; R 10 、R 13 、R 16 、R 19 、R 22 、R 25 Each of the following independently represents hydrogen, deuterium, a fluorine atom, a trifluoromethyl group, an adamantyl group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted Phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl.

9. The boron-containing organic compound according to claim 3 or 6, characterized in that: The R 10 、R 13 、R 16 、R 19 、R 22 、R 25 Each of the following independently represents hydrogen, deuterium, a fluorine atom, a trifluoromethyl group, an adamantyl group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted Phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl.

10. The boron-containing organic compound according to claim 4 or 5, characterized in that: The R9-R 26 Each of the following independently represents hydrogen, deuterium, a fluorine atom, a trifluoromethyl group, an adamantyl group, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a cyclohexyl group, a deuterated cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a naphthyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted Phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl.

11. The boron-containing organic compound according to any one of claims 1 to 6, characterized in that: The substituents for the above-mentioned substitutable groups may be selected from one or more of deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, and isobutyl.

12. The boron-containing organic compound according to claim 1, wherein: R1-R8 in the general formula (1) are independently represented by: hydrogen atoms, Any of the following; R9-R 26 They are expressed independently as: hydrogen atoms, Any one of them.

13. A boron-containing organic compound, characterized in that: The specific structural formula of the boron-containing organic compound is any one of the following structures:

14. An organic light-emitting device comprising a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, characterized in that: The functional layer of the organic light-emitting device comprises the boron-containing organic compound according to any one of claims 1 to 13.

15. The organic light-emitting device according to claim 14, wherein the functional layer comprises a light-emitting layer, characterized in that: The doping material of the light-emitting layer is the boron-containing organic compound according to any one of claims 1 to 13.

16. The organic light-emitting device according to claim 15, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, wherein: At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1 to 13.

17. The organic light-emitting device according to claim 15, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a doping material, wherein: The exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing organic compound according to any one of claims 1 to 13.

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