Nitrogen-containing organic compound and organic light-emitting device

Abstract

The invention belongs to the technical field of materials, and particularly relates to a nitrogen-containing organic compound and an organic light-emitting device. Based on a large conjugate spirofluorene indolo acridine structure, a naphthenic base unit with a branch configuration is introduced, and a mother nucleus structure with a stable three-dimensional skeleton is constructed. According to the design, intermolecular accumulation can be effectively inhibited, and the injection and transmission rate of holes and electrons in the device can be balanced, so that the exciton formation probability and the luminous efficiency are improved.

Description

Technical Field

[0001] This invention belongs to the field of materials technology, specifically relating to a nitrogen-containing organic compound and an organic light-emitting device. Background Technology

[0002] Currently, with the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Organic electroluminescent devices (OLEDs) typically include: a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] The main problems with existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. As displays become larger, the driving voltage also increases, necessitating improvements in both luminous efficiency and current efficiency. Therefore, it is essential to continue developing novel materials to further enhance the performance of OLEDs. Summary of the Invention

[0004] To address the shortcomings of existing technologies, this invention provides a nitrogen-containing organic compound and an organic light-emitting device.

[0005] The technical solution provided by this invention is as follows: To address the aforementioned technical problems, this invention provides a nitrogen-containing organic compound and an organic light-emitting device. It has the structure shown in Equation 1: X is selected from * represents the connection site between X and the parent nucleus of Formula 1; m is a natural number from 0 to 2; L1 is selected from single bonds and arylene groups with 6 to 12 carbon atoms; each R1 is independently selected from cyano, aryl with 6 to 30 substituted or unsubstituted carbon atoms, aryl amino group with 6 to 30 substituted or unsubstituted carbon atoms, and heteroaryl with 6 to 30 substituted or unsubstituted carbon atoms. The substituents of each R1 may be the same or different, and each is independently selected from cyano, alkyl with 1-10 carbon atoms, phenyl, or combinations thereof.

[0006] m is further selected from 0, 1, and 2.

[0007] In this invention, the arylene group L1 refers to the collective term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic hydrocarbon molecule. L1 can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene. Preferably, it has 6 to 14 carbon atoms, and most preferably, it has 6 to 12 carbon atoms. The monocyclic arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene; and the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, etc.

[0008] The L1 is selected from single bonds, phenylene, and polycyclic aryl groups having 2-3 phenyl groups.

[0009] More preferably, L1 is selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

[0010] In this invention, "substitution" means that the hydrogen atom on the compound group is replaced by another atom or group, and the substitution position is arbitrary; "unsubstitution" means that the hydrogen atom on the compound group is not replaced by another atom or group.

[0011] In this application, alkyl groups having 1-10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0012] Specifically, the aryl group with 6-30 carbon atoms is selected from monocyclic or polycyclic aryl groups having a structure of 1-3 benzene rings. In this application, the aryl group with 6-30 carbon atoms can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably having 6 to 22 carbon atoms, even more preferably having 6 to 18 carbon atoms, further preferably having 6 to 14 carbon atoms, and most preferably having 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, spiro-adamantyl-fluorenyl, triphenylene, fluoranthyl, etc., but not limited to this.

[0013] In this application, a heteroaryl group with 6-30 carbon atoms refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with 6-30 carbon atoms with heteroatoms. The heteroatoms include, but are not limited to, O, S, N or P, and preferably have 6 to 18 carbon atoms, and most preferably have 6 to 12 carbon atoms.

[0014] The aromatic amino group with 6-30 carbon atoms is represented by NR2R3, where R2 and R3 are selected from monocyclic or polycyclic aryl groups having 1-3 benzene ring structures, or polycyclic heteroaryl groups having 1-3 benzene ring structures.

[0015] The aryl group having 6-30 carbon atoms is selected from monocyclic aryl, polycyclic aryl, or fused-ring aryl with 2-4 independent aromatic rings.

[0016] The aryl group having 6-30 carbon atoms is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, diphenylfluorenyl, dimethylfluorenyl, and spirofluorenyl.

[0017] Specifically, the heteroaryl group having 6-30 carbon atoms is selected from polycyclic heteroaryl groups having 1-3 benzene rings. The substituted or unsubstituted heteroaryl group having 6-30 carbon atoms is selected from monocyclic aryl groups where at least one carbon atom is substituted by an N atom, or from fused heterocycles formed by the fusion of two monocyclic aromatic hydrocarbons with a saturated monoheterocyclic ring.

[0018] Specifically, the benzene ring structures in the polycyclic aryl group are connected by single bonds, fused together, or bonded to C1-C4 alkyl groups by single bonds.

[0019] Specifically, the polycyclic heteroaryl group is selected from monocyclic aryl groups with 1-3 benzene rings, polycyclic aryl groups, or polycyclic heteroaryl groups formed by meta-substituting a six-membered azine ring group with each other, or polycyclic heteroaryl groups formed by fusion of 1-3 benzene rings with a five-membered heteroaryl ring group at the center.

[0020] Preferably, the polycyclic heteroaryl group with a five-membered heteroaryl ring at its center has 1-2 benzene ring structures selected from: benzofuranyl, benzothiophenyl, benzoindolyl, dibenzofuranyl, dibenzothiophenyl, and carbazoleyl.

[0021] Preferably, the heteroaryl group having 6-30 carbon atoms, whether substituted or unsubstituted, is selected from substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzocarbazole; the substituents include deuterium, cyano, halogen, phenyl, biphenyl, naphthyl, and anthracene.

[0022] Specifically, L1 is a monocyclic or polycyclic aryl group having 1-3 benzene rings.

[0023] Preferably, the monocyclic aryl group having one benzene ring structure is selected from phenyl, and the polycyclic aryl group having two to three benzene ring structures is selected from biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and fluorene.

[0024] The compound represented by Formula 1 is any one of the following formulas 1-1 to 1-170: .

[0025] Secondly, this application provides an organic electroluminescent device, including a cathode, an anode, and an organic material layer disposed between the cathode and the anode, wherein the organic material layer includes the nitrogen-containing organic compound described in this application.

[0026] The organic material layer includes any one, two, or more of the following: a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light-emitting layer, and a light-emitting auxiliary layer.

[0027] Any layer of organic material can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances.

[0028] In one specific embodiment, the organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, all disposed in a single configuration.

[0029] The organic material layer containing nitrogen-containing organic compounds can be a light-emitting layer, an electron transport layer, or a hole transport layer.

[0030] The anode material is preferably a material with a high work function. It can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0031] The hole injection layer can be selected from any one or more of the following structures: metal compounds, porphyrin compounds, oligothiophene, aryl amine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, etc.

[0032] The hole transport layer can be a nitrogen-containing compound of this application, or it can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc.

[0033] The luminescent layer may contain only the guest material, or it may be in the form of the guest material dispersed in the host material, and may contain multiple host materials and multiple dopant materials. It may be a nitrogen-containing compound of this application.

[0034] The optimal doping ratio of the host material and guest material of the light-emitting layer can vary depending on the material used. Typically, the doping ratio of the guest material of the light-emitting layer is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0035] The electron transport layer may be a nitrogen-containing compound of this application, and may be selected from any one or more of the following structures: metal complexes, imidazole derivatives, carbazole derivatives, benzimidazole derivatives, quinoline derivatives, triazoles, phenanthroline derivatives, etc.

[0036] The electron injection layer may be selected from one or more of the following structures: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection capacity.

[0037] The cathode material can be selected from transparent metal oxides (e.g., ITO, IZO, etc.), Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, including their compounds or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0038] When manufacturing organic light-emitting devices, compounds can be used to form organic material layers through solution coating and vacuum deposition. Here, solution application methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0039] Thirdly, the present invention provides an electronic device including the organic electroluminescent device described herein. The electronic device can be a display device, a lighting device, an optical communication device, or other types of electronic devices. For example, it can include a computer screen, a mobile phone screen, a television set, etc., but is not limited thereto.

[0040] This application, based on a highly conjugated spirofluorene-indo-acridine structure, fused a cycloalkyl ring to the spirofluorene structure via covalent bonds. This "welded" a non-conjugated saturated aliphatic ring onto the core spirocarbon structure, constructing a parent core structure with a more stable three-dimensional framework for photoelectric performance. The saturated aliphatic ring of this design does not participate in the π-conjugated system of the molecule, but it can moderately lower the triplet energy level of the entire molecule through its hyperconjugated structure. Furthermore, its configuration, extending outward from the conjugated framework of the molecule, greatly increases the molecule's three-dimensional volume and twist, effectively suppressing intermolecular stacking and more effectively inhibiting concentration quenching and the formation of excitocomplexes. Further modification by introducing electron-donating or electron-deficient functional groups such as carbazole and triazine into the parent core allows for precise control of energy levels and photoelectric performance. When applied to organic electroluminescent devices, it exhibits high brightness, long lifetime, low efficiency roll-off, and excellent operational stability. Attached Figure Description

[0041] Figure 1 This is the NMR spectrum of compound 1-1 prepared in Example 1 of the present invention in deuterated chloroform solvent. Detailed Implementation

[0042] The following detailed description, using examples, aims to illustrate this specification. However, various other variations can be made based on the embodiments described herein, and the scope of this specification should not be construed as limited to the embodiments detailed below. The embodiments described herein are provided to provide a more complete explanation of this specification to those skilled in the art.

[0043] Unless otherwise specified in the examples, the procedures should be performed under standard conditions or conditions recommended by the manufacturer. Reagents or instruments whose manufacturers are not specified are all commercially available products.

[0044] The nitrogen-containing compound according to one embodiment of this specification can be manufactured by the basic synthetic process of routes S1 to S8 described below, but is not limited thereto. That is, intermediate 1 is prepared via routes S1, S2, and S3, and the nitrogen-containing compound can be prepared from intermediate 1 via routes S4, S5, and S6 or via route S7.

[0045] The specific route is as follows: Where X is a halogen, and X may be the same or different at each location; The definitions of L1, R1, and m are the same as those in Equation 1. The catalysts, ligands, bases, and solvents in each reaction system from route S1 to route S7 can all be made from common materials commonly used in existing technologies.

[0046] Example 1: Compound 1-1 S1: In a round-bottom flask, 300 mL of toluene, 7,7,10,10-tetramethyl-7,8,9,10-tetrahydro-5H-benzo[B]carbazole (27.74 g, 0.1 mol), 2-chlorobromobenzene (21.06 g, 0.11 mol), and sodium tert-butoxide (19.22 g, 0.2 mol) were added and stirred. Tris(dibenzylacetone)dipalladium (0.92 g, 1 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.58 g, 2 mmol) were added. Under nitrogen protection, the mixture was heated to 115 °C and reacted for 16 h. After the reaction was completed, 375 mL of toluene and 750 mL of deionized water were added to the reaction vessel, and the mixture was cooled to 20 °C. The mixture was separated, the upper organic phase was collected, magnesium sulfate was added, and the mixture was filtered and concentrated. Ethanol was added to induce crystallization, filtered, and dried to obtain 24.44 g of product, with a yield of 63%.

[0047] S2: In a 250 mL round-bottom flask containing tetrahydrofuran, the above S1 product (19.4 g, 0.05 mol) and 9-fluorenone (9.91 g, 0.055 mol) were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.058 mol) was slowly added dropwise. The reaction was carried out for 1 h, and 450 mL of dilute hydrochloric acid was added. The mixture was stirred, allowed to stand, separated, concentrated, and dried to obtain 18.95 g of product, with a yield of 71%.

[0048] S3: In a round-bottom flask, add the above S2 product (5.34 g, 10 mmol), 45 g acetic acid, and then add 1 g hydrochloric acid dropwise. Heat to 90 °C and react for 2 h. After the reaction is complete, cool to 25 °C. Filter to obtain the crude product, wash the crude product with ethanol, recrystallize, and dry to obtain compound 1-1 (12.69 g; yield: 82%). Mass spectrometry: MALDI-TOF-MS (m / z) = 515.29.

[0049] Nuclear magnetic resonance spectrum as follows Figure 1 As shown.

[0050] Example 2: Compounds 1-7 S2: Step S2 is the same as the synthesis step S2 in Example 1, except that 9-fluorenone in step S2 is replaced with 2-chloro-9-fluorenone (11.81 g, 0.055 mol), yielding 19.89 g of product, with a yield of 70%.

[0051] S3: Step S3 is the same as the synthesis step of S3 in Example 1, except that: the amount of product added in S2 is 19.89g (35mmol), 160g of acetic acid, and then 4g of hydrochloric acid is added dropwise to obtain 15.02g of product, with a yield of 78%.

[0052] S4: In a round-bottom flask, add 150 mL of toluene, 150 mL of tetrahydrofuran, and the above product S3 (11 g, 20 mmol). In an ice bath at -80 °C, add n-butyllithium (1.92 g, 30 mmol) and triisopropyl borate (4.14 g, 22 mmol) dropwise. Raise the temperature to room temperature and react for 3 h. After the reaction is complete, add hydrochloric acid to adjust the pH to 3, separate the solution and concentrate it in tetrahydrofuran, add dilute hydrochloric acid to slurry, separate the solution and dry it, filter and concentrate it, and dry it to obtain 8.5 g of product, with a yield of 76%.

[0053] S5: In a round-bottom flask, add a mixed solution of 200 mL toluene, 90 mL ethanol, and 90 mL water. Add the above S4 product (5.6 g, 0.01 mol), 9-bromo-10-phenylanthracene (3.67 g, 11 mmol), potassium carbonate (2.76 g, 20 mmol), and 0.01 g Pd132 (dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium) to the solution. Under nitrogen protection, heat to 80 °C and react for 1 h. After the reaction is complete, add 90 mL of water, separate the liquid and liquid phases, collect the organic phase, concentrate it, add ethanol, slurry, filter, and vacuum dry to obtain compounds 1-7 (4.99 g; yield: 65%). Mass spectrometry: MALDI-TOF-MS (m / z) = 767.35.

[0054] Example 3: Compounds 1-9 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 3-chloro-9-fluorenone, and 9-bromo-10-phenylanthracene in step S5 is replaced with 9-(3-bromophenyl)phenanthrene (3.67 g, 11 mmol), to obtain compounds 1-9 (5.53 g; yield: 72%), mass spectrometry: MALDI-TOF-MS (m / z) = 767.38.

[0055] Example 4: Compounds 1-12 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 2-chloro-9,9-dimethylfluorene (2.52 g, 11 mmol) to obtain compounds 1-12 (4.74 g; yield: 67%). Mass spectrometry: MALDI-TOF-MS (m / z) = 707.37.

[0056] Example 5: Compounds 1-18 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 1-chloro-9-fluorenone, and 9-bromo-10-phenylanthracene in step S5 is replaced with 9-(3-bromophenyl)-9H-carbazole-3-onitrile (3.82 g, 11 mmol), to obtain compound 1-18 (5.47 g; yield: 70%), mass spectrometry: MALDI-TOF-MS (m / z) = 781.34.

[0057] Example 6: Compounds 1-20 Steps S2-S3 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 2,7-dichloro-9-fluorenone (13.70 g, 0.055 mol), yielding 14.73 g of product, with a yield of 72%.

[0058] S4: In a round-bottom flask, add 150 mL of toluene, 150 mL of tetrahydrofuran, and the above product (11.69 g, 20 mmol). In an ice bath at -80 °C, add n-butyllithium (1.35 g, 21 mmol) and triisopropyl borate (8.28 g, 44 mmol) dropwise. Raise the temperature to room temperature and react for 3 h. After the reaction is complete, add hydrochloric acid to adjust the pH to 3. Separate the solution and concentrate it in tetrahydrofuran. Add dilute hydrochloric acid and stir. Separately dry the solution, filter and concentrate, and dry to obtain 9.17 g of product, yield 76%.

[0059] S5: In a round-bottom flask, add a mixed solution of 100 mL toluene, 45 mL ethanol, and 45 mL water. Add the product obtained in step S4 (6.03 g, 10 mmol), bromobenzene (3.45 g, 22 mmol), potassium carbonate (2.76 g, 20 mmol), and 0.01 g Pd132 (dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium) to the solution. Under nitrogen protection, heat to 80 °C and react for 1 h. After the reaction is complete, add 90 mL of water, separate the liquid and liquid phases, collect the organic phase, concentrate it, add ethanol, slurry, filter, and vacuum dry to obtain compound 1-20 (4.34 g; yield: 65%). Mass spectrometry: MALDI-TOF-MS (m / z) = 667.30.

[0060] Example 7: Compounds 1-27 Steps S2-S3 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 2-chloro-5-phenyl-9-fluorenone (16g, 0.055mol), yielding 17.53g of product, with a yield of 80%.

[0061] S4: Add 250 mL of toluene to a round-bottom flask, then add the above product (12.52 g, 20 mmol), 9H-carbazole (3.68 g, 22 mmol), sodium tert-butoxide (3.84 g, 40 mmol), and tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol). Stir and, under nitrogen protection, heat to 115 °C and react for 16 h. After the reaction is complete, add 250 mL of toluene and 500 mL of water to the reaction solution, cool to 20 °C, allow to stand, separate the liquid and filter the organic phase. Concentrate the filtrate, add ethanol, cool to precipitate crystals, filter, and dry to obtain compound 1-27 (11.05 g; yield: 73%). Mass spectrometry: MALDI-TOF-MS (m / z) = 756.35.

[0062] Example 8: Compounds 1-28 Steps S2-S3 are the same as the synthesis steps in Example 6, except that 2,7-dichloro-9-fluorenone in step S2 is replaced with 3,6-dichloro-9-fluorenone, yielding 13.70g of product with a yield of 67%.

[0063] S4: Add 250 mL of toluene to a round-bottom flask, then add the product obtained in step S3 (11.69 g, 20 mmol), carbazole (7.36 g, 44 mmol), sodium tert-butoxide (3.84 g, 40 mmol), and tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol). Stir and, under nitrogen protection, heat to 115 °C and react for 16 h. After the reaction is complete, add 250 mL of toluene and 500 mL of water to the reaction solution, cool to 20 °C, allow to stand, separate the liquid and filter the organic phase. Concentrate the filtrate, add ethanol, cool to precipitate crystals, filter, and dry to obtain compound 1-28 (11.85 g; yield: 70%). Mass spectrometry: MALDI-TOF-MS (m / z) = 845.38.

[0064] Example 9: Compounds 1-30 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 2-bromo-4,6-diphenyl-1,3,5-triazine (3.43 g, 11 mmol), which yields compound 1-30 (5.68 g; yield: 69%). Mass spectrometry: MALDI-TOF-MS (m / z) = 746.30.

[0065] Example 10: Compounds 1-32 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 2,4-bis([1,1'-biphenyl]-4-yl)-6-bromo-1,3,5-triazine (CAS: 1898263-50-7) (5.12 g, 11 mmol), which yields compound 1-32 (5.66 g; yield: 63%). Mass spectrometry: MALDI-TOF-MS (m / z) = 897.42.

[0066] Example 11: Compounds 1-36 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 3-chloro-9-fluorenone, and 9-bromo-10-phenylanthracene in step S5 is replaced with 2-bromo-4,6-diphenyl-1,3,5-triazine (3.43 g, 11 mmol), to obtain compound 1-36 (4.86 g; yield: 65%), mass spectrometry: MALDI-TOF-MS (m / z) = 746.28.

[0067] Example 12: Compounds 1-62 Steps S1-S5 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 2-chloro-6-phenyl-9-fluorenone (16 g, 0.055 mol), and 9-bromo-10-phenylanthracene in step S5 is replaced with 2-bromo-4,6-diphenyl-1,3,5-triazine (3.43 g, 11 mmol), to obtain compound 1-62 (5.60 g; yield: 68%), mass spectrometry: MALDI-TOF-MS (m / z) = 822.37.

[0068] Example 13: Compounds 1-66 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 2-chloro-9-fluorenone in step S2 is replaced with 7-chloro-9-fluorenone-2-nitrile (13.18 g, 0.055 mol), and 9-bromo-10-phenylanthracene in step S5 is replaced with 2-bromo-4-(2-naphthyl)-6-phenyl-1,3,5-triazine (CAS: 2011776-79-5) (3.98 g, 11 mmol), to obtain compound 1-66 (5.82 g; yield: 71%), mass spectrometry: MALDI-TOF-MS (m / z) = 821.34.

[0069] Example 14: Compounds 1-67 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (CAS: 23449-08-3) (4.27 g, 11 mmol), which yields compound 1-67 (5.44 g; yield: 66%). Mass spectrometry: MALDI-TOF-MS (m / z) = 822.35.

[0070] Example 15: Compounds 1-94 Steps S2-S4 are the same as the synthesis steps in Example 7, except that 2-chloro-5-phenyl-9-fluorenone in step S2 is replaced with 2-chloro-9-fluorenone (11.81 g, 0.055 mol), and 9H-carbazole in step S4 is replaced with p-di-tert-butylaniline (6.19 g, 22 mmol), to obtain compound 1-94 (12.26 g; yield: 77%), mass spectrometry: MALDI-TOF-MS (m / z) = 794.46.

[0071] Example 16: Compound 1-110 Steps S2-S4 are the same as the synthesis steps in Example 7, except that 2-chloro-5-phenyl-9-fluorenone in step S2 is replaced with 2-chloro-9-fluorenone (11.81 g, 0.055 mol), and 9H-carbazole in step S4 is replaced with N-(2-biphenyl)-9,9-dimethylfluoren-2-amine (7.95 g, 22 mmol), to obtain compound 1-110 (12.08 g; yield: 69%), mass spectrometry: MALDI-TOF-MS (m / z) = 874.39.

[0072] Example 17: Compound 1-126 Steps S2-S4 are the same as the synthesis steps in Example 7, except that 2-chloro-5-phenyl-9-fluorenone in step S2 is replaced with 2-chloro-7-phenyl-9-fluorenone, and 9H-carbazole in step S4 is replaced with p-methyldiphenylamine (4.34 g, 22 mmol), to obtain compound 1-126 (11.80 g; yield: 75%), mass spectrometry: MALDI-TOF-MS (m / z) = 786.35.

[0073] Example 18: Compound 1-143 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 4-bromo-N,N-di-p-methylaniline (3.88 g, 11 mmol), which yields compound 1-143 (5.6 g; yield: 71%). Mass spectrometry: MALDI-TOF-MS (m / z) = 786.41.

[0074] Example 19: Compound 1-164 Steps S2-S5 are the same as the synthesis steps in Example 2, except that 9-bromo-10-phenylanthracene in step S5 is replaced with 4-bromo-N,N-diphenyl-1-naphthylamine (CAS: 227314-47-8) (4.12 g, 11 mmol), which yields compound 1-164 (6.0 g; yield: 74%). Mass spectrometry: MALDI-TOF-MS (m / z) = 808.32.

[0075] Example 20: Compound 1-169 Steps S2-S4 are the same as the synthesis steps in Example 8, except that 3,6-dichloro-9-fluorenone in step S2 is replaced with 2,7-dichloro-9-fluorenone, and carbazole is replaced with diphenylamine (7.45 g, 44 mmol), to obtain compound 1-169 (12.24 g; yield: 72%), mass spectrometry: MALDI-TOF-MS (m / z) = 849.40.

[0076] Fabrication of organic electroluminescent devices: Device Example 1: The glass substrate with a 120nm ITO transparent film was ultrasonically cleaned with acetone, isopropanol and deionized water for 10 minutes each, vacuum dried at 105°C for 2 hours, and then UV ozone washed for 15 minutes. After that, the ITO glass substrate was transferred to a vacuum evaporation machine. On the side where the ITO thin film is formed, molybdenum trioxide (MoO3) is vacuum-deposited to form a 10 nm thick hole injection layer. On the hole injection layer described above, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC) is vacuum evaporated to form a hole transport layer with a thickness of 70 nm. On the hole transport layer described above, compound 1-1 (as the light-emitting host material, 90 wt%) and Ir(ppy)3 (as the light-emitting guest material, 10 wt%) prepared in Example 1 were jointly vacuum evaporated to form a light-emitting layer with a thickness of 30 nm. On the aforementioned light-emitting layer, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) is vacuum-deposited to form a 5 nm electron-blocking layer. On the aforementioned electron blocking layer, 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (TmPyPB) is vacuum-deposited to form an electron transport layer with a thickness of 40 nm. On the aforementioned electron transport layer, lithium fluoride (LiF) is vacuum-deposited to form an electron injection layer with a thickness of 1 nm. Finally, aluminum (Al) is vacuum-deposited onto the aforementioned electron injection layer to form a 100 nm cathode.

[0077] Device Examples 2 to 11 Organic electroluminescent devices were prepared using the same method as in Device Example 1, except that compounds 1-1 prepared in Synthesis Example 1 were replaced with compounds synthesized in Synthesis Examples 5 to 14.

[0078] Device Comparison Example 1 The organic electroluminescent device was fabricated using the same method as in Example 1, except that compound D1 was used instead of compound 1-1 in Example 1 when forming the light-emitting layer.

[0079] Performance testing: The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Examples 1-11 and Comparative Example 1 of the present invention are shown in Table 1: Table 1 Performance testing: The electrochemical properties, thermodynamic properties, and hole transport properties of the compounds synthesized in Synthesis Examples 2 to 5, Synthesis Examples 15 to 20 of this invention, as well as compound D2, were tested. The test results are shown in Table 2. Table 2 As can be seen from Table 1 or Table 2 above, when the compounds provided by this invention are used as the hole transport layer or light-emitting layer of organic electroluminescent devices, the driving voltage of organic electroluminescent devices can be effectively reduced, the luminous efficiency of the devices can be improved, and the service life of the devices can be extended.

[0080] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A nitrogen-containing organic compound, characterized in that, It has the structure shown in Equation 1: X is selected from * represents the connection site between X and Formula 1; m is a natural number from 0 to 2; L1 is selected from single bonds or arylene groups with 6 to 12 carbon atoms; each R1 is independently selected from cyano, aryl with 6 to 30 substituted or unsubstituted carbon atoms, aryl amino group with 6 to 30 substituted or unsubstituted carbon atoms, or heteroaryl with 6 to 30 substituted or unsubstituted carbon atoms. The substituents of each R1 may be the same or different, and each is independently selected from cyano, alkyl with 1-10 carbon atoms, phenyl, or a combination thereof.

2. The nitrogen-containing organic compound according to claim 1, characterized in that... : The aryl group having 6-30 carbon atoms is selected from monocyclic or polycyclic aryl groups having 1-3 benzene rings. The aromatic amino group with 6-30 carbon atoms is represented by NR2R3, where R2 and R3 are selected from monocyclic or polycyclic aryl groups having 1-3 benzene ring structures, or polycyclic heteroaryl groups having 1-3 benzene ring structures. The heteroaryl group having 6-30 carbon atoms is selected from polycyclic heteroaryl groups having 1-3 benzene rings.

3. A nitrogen-containing organic compound according to claim 2, characterized in that: The benzene ring structures in the polycyclic aryl group are connected by single bonds, fused together, or bonded to C1-C4 alkyl groups by single bonds; The polycyclic heteroaryl group is selected from monocyclic aryl groups with 1-3 benzene rings, polycyclic aryl groups, or polycyclic heteroaryl groups formed by meta-substitution of a six-membered azine ring group with each other, or polycyclic heteroaryl groups formed by fusion of 1-3 benzene rings with a five-membered heteroaryl ring group at the center.

4. A nitrogen-containing organic compound according to claim 1, characterized in that, The L1 is a monocyclic or polycyclic aryl group having 1-3 benzene rings.

5. A nitrogen-containing organic compound according to any one of claims 2-3, characterized in that, The monocyclic aryl group having one benzene ring structure is selected from phenyl, and the polycyclic aryl group having two to three benzene ring structures is selected from biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and fluorene.

6. A nitrogen-containing organic compound according to claim 3, characterized in that, The polycyclic heteroaryl group with a five-membered heteroaryl ring at its center has 1-2 benzene ring structures, selected from: benzofuranyl, benzothiophenyl, benzoindolyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl.

7. A nitrogen-containing organic compound according to claim 1, characterized in that, The compound represented by Formula 1 is any one of the following formulas 1-1 to 1-170: / 。 8. An organic light-emitting device, comprising a cathode, an anode, and an organic material layer disposed between the cathode and the anode, characterized in that, The organic material layer comprises the nitrogen-containing organic compound as described in any one of claims 1-7.

9. An organic light-emitting device according to claim 8, characterized in that, The organic material layer includes any one, two, or more of the following: a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light-emitting layer, and a light-emitting auxiliary layer.

10. An organic light-emitting device according to claim 9, characterized in that, The organic material layer containing nitrogen-containing organic compounds is a light-emitting layer, an electron transport layer, or a hole transport layer.

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