Organic fused ring compound and organic electroluminescent device prepared from organic fused ring compound

Abstract

The invention belongs to the technical field of materials, and particularly relates to an organic fused ring compound and an organic electroluminescent device prepared from the organic fused ring compound. According to the compound disclosed by the invention, alicyclic rings and spirorings are fused to form a rigid main body structure with a twisted structure, so that the compound has relatively high thermal stability and high solubility. When the compound is applied to an organic light-emitting device, it is possible to obtain an organic light-emitting device having high efficiency, low voltage, and long lifespan characteristics.

Description

Technical Field

[0001] This invention belongs to the field of materials technology, specifically relating to an organic fused-ring compound and the organic electroluminescent device prepared therefrom. Background Technology

[0002] Compared to LCDs, which are the mainstream display devices for flat panel displays, organic light-emitting devices are self-emissive and can be driven at low voltage. They have excellent viewing angles and contrast, do not require backlights, are thinner and lighter, consume less energy, have advantages in power consumption, and have a wide range of color reproduction. They have become the mainstream display solution for small and medium-sized devices as well as high-end devices.

[0003] In organic light-emitting diodes (OLEDs), materials used in the organic layer can be categorized by function into luminescent materials and charge-transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, luminescent materials can be classified by emission color into blue, green, and red materials. However, if a single pure organic material is used as the active material in the luminescent layer, the emission peak is prone to shift towards longer wavelengths due to intermolecular aggregation effects (such as π-π stacking), accompanied by an increased probability of nonradiative transitions, leading to luminescence decay and ultimately deterioration of color purity and a decrease in external quantum efficiency. To address this issue, the current mainstream technology employs a host / dopant co-construction system for the luminescent layer: the host material provides a stable molecular environment and confines excitons, efficiently transferring them to dopant molecules, thereby significantly suppressing redshift, improving color purity, and maximizing the device's luminescence efficiency and lifetime.

[0004] The superior properties of organic light-emitting devices (OLEDs) rely heavily on the chemical stability and photoelectric efficiency of the organic functional layer materials. A stable molecular structure is also crucial for ensuring long device lifespan, while efficient carrier transport / injection capabilities and high fluorescence / phosphorescence quantum yields are key to achieving high brightness and efficiency. However, organic functional layer materials possessing both high stability and high photoelectric performance remain scarce in the industry. Therefore, continuous development of new materials for OLEDs is necessary. Summary of the Invention

[0005] To address the shortcomings of existing technologies, this invention provides an organic fused-ring compound and an organic electroluminescent device prepared therefrom.

[0006] The technical solution provided by this invention is as follows: Organic fused-ring compounds, wherein the compounds have the structural formula shown in Formula 1: Wherein, A is a C5 to C6 aliphatic hydrocarbon ring, and R1 and R2 are independently selected from substituted or unsubstituted C6 to C6 hydrocarbon rings. 12 The aryl group, R1 and R2 are independent, or R1 and R2 are bonded together by single bonds to form a fused ring structure; The substituted C6 to C 12 The aryl group is C6 to C6. 12 One or more H atoms at any position on the aryl group are replaced by R', where R' is... m is selected from 0 or 1, and Ar1 is selected from C6 to C1. 12 The arylene group, R is selected from substituted or unsubstituted C1 to C4 alkyl groups, C6 to C4 alkyl groups. 30 aryl, C6 to C 30 Aromatic amino groups, C6 to C 30 heteroaryl groups; The substituted C6 to C 30 aryl, C6 to C 30 Aromatic amino groups, C6 to C 30 The substituents in the heteroaryl group are one or more of deuterium, cyano, C1-C4 alkyl, and phenyl.

[0007] Specifically, A is selected from cyclopentane or cyclohexane.

[0008] Specifically, R1 and R2, whether the same or different, are selected from substituted or unsubstituted monocyclic aryl groups, or substituted or unsubstituted polycyclic aryl groups formed by two monocyclic aryl groups through single bonds or fusion bonds; The Ar1 is selected from monocyclic aryl groups and polycyclic aryl groups formed by two monocyclic aryl groups linked by a single bond or fusion bond.

[0009] Specifically, R1 and R2 form a fused ring structure through single-bond bonding, which has the following structural formula: , , , , The connection points of R1 and R2 in Equation 1 are given.

[0010] Specifically, Ar1 is selected from phenylene, biphenylene, or naphthylene.

[0011] Specifically, the unsubstituted C6 to C 30 The aryl group is selected from R3 to R7 are each independently selected from H, C1-C4 alkyl or phenyl groups; R3 to R7 are independent of each other and are bonded to the central phenyl group by a single bond, or are fused together by a single bond between any two adjacent substituents in R3 to R7, or are fused together by 1-2 non-adjacent substituents in R3 to R7 with the central phenyl group.

[0012] Specifically, the unsubstituted C6 to C 30 heteroaryl groups selected from or Y2 is selected from N(R) 13), O or S; Y1, Z1-Z3 are each independently selected from CH or N, and Z1-Z3 are not simultaneously C; R8, R 13 Selected from H, C1-C4 alkyl or phenyl groups; R8 is linked by a single bond or fused with Y1 by sharing a pair of chemical bonds; R9, R 10 Selected from the groups shown in Formula 2 or Formula 3.

[0013] Specifically, the unsubstituted C6 to C 30 Aromatic amino groups are selected from R 11 To R 12 Each group is independently selected from the groups shown in Formula 2 or Formula 3.

[0014] * indicates a connection point.

[0015] Preferably, the second formula is selected from... , , , , , ; Preferably, the third formula is selected from: , , , ; Preferably, the fourth formula is selected from: , , , , , , , , ; Preferably, Formula 5 is selected from... , , , , , , , , ,

[0016] Preferably, the organic fused-ring compound is selected from the following structural formulas: .

[0017] Secondly, this application provides an organic electroluminescent device, including a first electrode and a second electrode disposed opposite to each other, wherein an organic layer is disposed between the first electrode and the second electrode, and the organic layer includes the aforementioned organic fused ring compound.

[0018] The organic 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. The organic layer containing an organic fused ring compound is a light-emitting layer, an electron transport layer, or a hole transport layer.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] 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 dopants. It may be a compound of this application.

[0023] 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%.

[0024] The electron transport layer 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.

[0025] 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.

[0026] The cathode material may 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 to these.

[0027] 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.

[0028] 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.

[0029] The compounds of this invention form a rigid host structure with a twisted structure by fusing alicyclic and spirocyclic rings, representing a novel type of core structure with high thermal stability and solubility. When the electron cloud density of the core structure is adjusted by electron-donating or electron-donating groups and applied to organic light-emitting devices, organic light-emitting devices with high efficiency, low voltage, and long lifespan can be obtained. Detailed Implementation

[0030] The principles and features of the present invention are described below. The embodiments given are only for explaining the present invention and are not intended to limit the scope of the present invention.

[0031] 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.

[0032] The core structure of a compound represented by Formula 1 according to an exemplary embodiment of this specification can be prepared as shown in the following reaction. Substituents can be bonded by methods known in the art or purchased from the market, and the type and position of substituents or the number of substituents can be varied according to techniques known in the art.

[0033] A is a C5 to C6 aliphatic hydrocarbon ring, and X1 and X2 are substituents or halogens.

[0034] When X1 and X2 are halogens, intermediate 2 is boronized using a known method and then reacted with a halogenated compound via a Suzuki reaction, or intermediate 2 is coupled with an NH-containing substituent via a Buchwald–Hartwig coupling reaction to obtain the compound of this application.

[0035] Preparation of intermediate 1-a: In a round-bottom flask, 300 mL of toluene, 3a,8b-dimethyl-1,2,3,3a,4,8b-hexahydrocyclopentanoindole (18.73 g, 0.1 mol), o-bromoiodobenzene (31.12 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, and 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 27.04 g of intermediate 1-a, with a yield of 79%.

[0036] Preparation of intermediate 1-b: In a round-bottom flask, 300 mL of toluene, 2,3,4,4A,9,9A-hexahydro-4A,9A-dimethyl-1H-carbazole (20.13 g, 0.5 mol), o-bromoiodobenzene (31.12 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, and 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 28.85 g of intermediate 1-b, with a yield of 81%.

[0037] Example 1: Preparation of Compound 15 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 4,4'-dichlorobenzophenone (15.1 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 15.82 g of intermediate 2-a, with a yield of 62%. In a 250 mL round-bottom flask, intermediate 2-a (10.21 g, 20 mmol), carbazole (7.36 g, 44 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and the liquid was separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 9.56 g of compound 15, with a yield of 70%. The MALDI-TOF-MS mass spectrometry reading was 772.36 ([M+H)). + ).

[0038] Example 2: Preparation of Compound 16 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 4-chloro-4'-methylbenzophenone (13.84 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 14.70 g of intermediate 2-b, with a yield of 60%. In a 250 mL round-bottom flask, intermediate 2-b (9.80 g, 20 mmol), diphenylamine (3.55 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and the liquid was separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 9.20 g of compound 16, with a yield of 74%. The MALDI-TOF-MS mass spectrometry value was 623.34 ([M+H)). + ).

[0039] Example 3: Preparation of Compound 22 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 2-chlorofluorenone (12.88 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 15.40 g of intermediate 2-c, with a yield of 65%. In a 250 mL round-bottom flask, intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol) were added. The mixture was heated to 100 °C for 2 h under nitrogen protection. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the filtrate was collected and concentrated to dryness. Then, 1-bromo-2-phenylnaphthalene (3.45 g, 22 mmol) and potassium carbonate (5... 0.53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 7.06 g of compound 22, with a yield of 55%. MALDI-TOF-MS analysis showed a value of 642.31 ([M+H)). + ).

[0040] Example 4: Preparation of Compound 24 In a 250 mL round-bottom flask, add intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate, and concentrate to dryness. Add 9-(4-bromophenyl)phenanthrene (7.33 g, 22 mmol) and potassium carbonate (5... 0.53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 8.02 g of compound 24, with a yield of 58%. MALDI-TOF-MS analysis showed a value of 692.32 ([M+H)). + ).

[0041] Example 5: Preparation of Compound 27 In a 250 mL round-bottom flask, intermediate 2-C (9.48 g, 20 mmol), 4,4'-dimethyldiphenylamine (4.14 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 9.76 g of compound 27, with a yield of 77%. The MALDI-TOF-MS mass spectrometry value was 635.33 ([M+H)). + ).

[0042] Example 6: Preparation of compound 37 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 3-chlorofluorenone (12.88 g, 60 mmol), and 150 mL tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g acetic acid was added dropwise, followed by 5 g hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 14.92 g of intermediate 2-d, with a yield of 63%. In a 250 mL round-bottom flask, intermediate 2-d (9.48 g, 20 mmol), N-[1,1'-biphenyl]-2-yl-9,9-dimethyl-9H-fluorene-2-amine (7.59 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 10.86 g of compound 37, with a yield of 68%. The MALDI-TOF-MS mass spectrometry value was 799.39 ([M+H)). + ).

[0043] Example 7: Preparation of Compound 42 In a 250 mL round-bottom flask, add intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate, and concentrate to dryness. Add 4-bromo-N,N-diphenyl-1-naphthylamine (8.23 g, 22 mmol) and potassium carbonate (5... 0.53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 7.92 g of compound 42, with a yield of 54%. MALDI-TOF-MS analysis showed a value of 733.35 ([M+H)). +).

[0044] Example 8: Preparation of Compound 50 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 6-chloro-2-phenylfluorenone (17.44 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 15.67 g of intermediate 2-e, with a yield of 57%. In a 250 mL round-bottom flask, intermediate 2-e (11.00 g, 20 mmol), N-phenyl-9,9-dimethylfluorene-2-amine (5.99 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 11.82 g of compound 50, with a yield of 74%. The MALDI-TOF-MS mass spectrometry value was 799.40 ([M+H)). + ).

[0045] Example 9: Preparation of Compound 58 In a 250 mL round-bottom flask, add intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate and concentrate to dryness. Add 4-chloro-2-phenyldibenzofuran (6.13 g, 22 mmol) and potassium carbonate (5 g, 0.2 mmol). 53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 7.09 g of compound 58, with a yield of 52%. MALDI-TOF-MS analysis showed a value of 682.30 ([M+H)). + ).

[0046] Example 10: Preparation of Compound 64 In a 250 mL round-bottom flask, intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diborate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol) were added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filtrate was collected and concentrated to dryness. 9-(4-bromophenyl)-3,6-dimethylcarbazole (7.71 g, 22 mmol) and potassium carbonate were then added. (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 8.08 g of compound 64, with a yield of 57%. MALDI-TOF-MS analysis showed a value of 709.34 ([M+H)). + ).

[0047] Example 11: Preparation of Compound 67 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 7-chloro-4-phenylfluorenone (17.44 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 16.22 g of intermediate 2-f, with a yield of 59%. In a 250 mL round-bottom flask, intermediate 2-f (11.00 g, 20 mmol), 3,6-dimethylcarbazole (4.10 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 11.20 g of compound 67, with a yield of 79%. The MALDI-TOF-MS mass spectrometry value was 709.35 ([M+H)). + ).

[0048] Example 12: Preparation of Compound 73 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 2,7-dichlorofluorenone (14.95 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 15.25 g of intermediate 2-, with a yield of 60%. In a 250 mL round-bottom flask, 2 g (10.17 g, 20 mmol) of intermediate, 8.68 g (44 mmol) of 4,4'-dimethyldiphenylamine, 3.84 g (40 mmol) of sodium tert-butoxide, 0.2 g (0.2 mmol) of tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol) and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 11.78 g of compound 73, with a yield of 71%. The MALDI-TOF-MS mass spectrometry value was 830.41 ([M+H)). + ).

[0049] Example 13: Preparation of Compound 94 In a 250 mL round-bottom flask, intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol) were added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 2 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the filtrate was collected and concentrated to dryness. Then, 4-(3-bromophenyl)-2,6-biphenylpyrimidine (8.52 g, 22 mmol) and carbon were added. Potassium sulfate (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 8.35 g of compound 94, with a yield of 56%. MALDI-TOF-MS analysis showed a value of 746.34 ([M+H)). + ).

[0050] Example 14: Preparation of Compound 95 In a 250 mL round-bottom flask, intermediate 2-C (9.48 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.15 g, 0.2 mmol) were added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filtrate was collected and concentrated to dryness. Then, 2-(3'-bromobiphenyl)-4,6-diphenyl-1,3,5-triazine (10.22 g, 22 mmol) was added. Potassium carbonate (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 9.70 g of compound 95, with a yield of 59%. MALDI-TOF-MS analysis showed a value of 823.39 ([M+H)). + ).

[0051] Example 15: Preparation of Compound 98 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 7-chloro-4-phenylfluorenone (17.44 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 17.05 g of intermediate 2-h, with a yield of 62%. In a 250 mL round-bottom flask, add intermediate 2-h (11.00 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate and concentrate to dryness. Add 4-bromo-2,6-diphenylpyrimidine (6.85 g, 22 mmol) and potassium carbonate. (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 7.60 g of compound 98, with a yield of 51%. MALDI-TOF-MS analysis showed a value of 746.34 ([M+H)). + ).

[0052] Example 16: Preparation of Compound 103 In a 250 mL round-bottom flask, add intermediate 2-g (10.17 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (13.2 g, 52 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate and concentrate to dryness. Add 2-chloro-4,6-diphenyl-1,3,5-triazine (11.78 g, 44 mmol) and carbonate. Potassium (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 8.66 g of compound 103, with a yield of 48%. MALDI-TOF-MS analysis showed a value of 902.38 ([M+H)). + ).

[0053] Example 17: Preparation of Compound 110 In a 250 mL round-bottom flask, add intermediate 2-h (11.00 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate, and concentrate to dryness. Add 2-bromo-1-phenyl-1H-benzimidazole (6.00 g, 22 mmol) and potassium carbonate (5... 0.53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 7.79 g of compound 110, with a yield of 55%. MALDI-TOF-MS analysis showed a value of 708.33 ([M+H)). + ).

[0054] Example 18: Preparation of Compound 132 In a 250 mL round-bottom flask, intermediate 1-a (17.11 g, 50 mmol), 2-chlorofluorenone (12.88 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 13.80 g of intermediate 2-i, with a yield of 60%. In a 250 mL round-bottom flask, add intermediate 2-i (9.20 g, 20 mmol), 100 mL of dioxane, pinacol diboronate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol). Under nitrogen protection, heat to 100 °C and react for 2 h. After the reaction is complete, cool to room temperature, filter, collect the filtrate, concentrate to dryness, and add 4-bromo-2,6-diphenylpyrimidine (6.85 g, 22 mmol) and potassium carbonate (…). 5.53 g (40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 9.21 g of compound 132, with a yield of 57%. MALDI-TOF-MS analysis showed a value of 809.34 ([M+H)). + ).

[0055] Example 19: Preparation of Compound 149 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 3-bromobenzo[a]fluorenone (18.55 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 14.20 g of intermediate 2-j, with a yield of 50%. In a 250 mL round-bottom flask, intermediate 2-f (11.37 g, 20 mmol), N-phenyl-9,9-dimethylfluorene-2-amine (5.99 g, 21 mmol), sodium tert-butoxide (3.84 g, 40 mmol), tris(dibenzylacetone)dipalladium (0.2 g, 0.2 mmol), and 100 mL of toluene were added. The mixture was stirred and heated to 115 °C under nitrogen protection for 16 h. After the reaction was complete, 250 mL of toluene and 500 mL of water were added to the reaction solution. The mixture was cooled to 20 °C, allowed to stand, and separated. The organic phase was filtered, the filtrate was concentrated, and ethanol was added to cool and crystallize. The crystals were filtered and dried to obtain 10.98 g of compound 149, with a yield of 71%. The MALDI-TOF-MS mass spectrometry value was 773.39 ([M+H)).+ ).

[0056] Example 20: Preparation of Compound 149 In a 250 mL round-bottom flask, intermediate 1-b (17.82 g, 50 mmol), 2-bromobenzo[a]fluorenone (18.55 g, 60 mmol), and 150 mL of tetrahydrofuran were added. Under nitrogen protection, the mixture was cooled to -80 °C, and n-butyllithium (3.68 g, 0.06 mol) was slowly added dropwise. The reaction was allowed to proceed for 1 h, the cold bath was removed, and the mixture was allowed to heat naturally for 1 h. 450 mL of dilute hydrochloric acid was added, the mixture was stirred, allowed to stand, and the liquid phase was separated. The organic phase was concentrated, and 200 g of acetic acid was added dropwise, followed by 5 g of hydrochloric acid. The mixture was heated to 90 °C and reacted for 2 h. After the reaction was completed, the mixture was cooled to 25 °C. The crude product was obtained by filtration, washed with ethanol, recrystallized, and dried to obtain 15.05 g of intermediate 2-h, with a yield of 53%. In a 250 mL round-bottom flask, intermediate 2-h (11.37 g, 20 mmol), 100 mL of dioxane, pinacol diborate (6.6 g, 26 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (0.15 g, 0.2 mmol) were added. Under nitrogen protection, the mixture was heated to 100 °C and reacted for 2 h. After the reaction was complete, the mixture was cooled to room temperature, filtered, and the filtrate was collected and concentrated to dryness. Then, 3'-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-4-carboxynitrile (8.1 g, 0.2 mmol) was added. 1 g (22 mmol), potassium carbonate (5.53 g, 40 mmol), dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (0.15 g, 0.2 mmol), 60 mL toluene, 30 mL ethanol, and 30 mL water were added. The mixture was heated to 80 °C for 12 h under nitrogen protection. After the reaction, the reaction solution was separated, cooled to 10-15 °C to crystallize, and filtered to obtain the crude product. The crude product was washed with ethanol and recrystallized to give 9.52 g of compound 132, with a yield of 58%. MALDI-TOF-MS analysis showed a value of 822.35 ([M+H)). + ).

[0057] Material performance testing: The glass transition temperature (Tg) of the compounds synthesized in Synthetic Examples 1 to 12 and 19 was tested using differential thermal analysis. The hole mobility of the compounds obtained in the above synthetic examples was tested using the space charge confinement method. The solubility of the compounds obtained in the above synthetic examples was tested by dissolving them in dichloromethane at room temperature. A + indicates solubility ≥ 20 mg / mL, and a - indicates solubility ≤ 10 mg / mL. For comparison, the physical properties of the compound in Comparative Example D1 were also evaluated in the same way, and the test results are shown in Table 1.

[0058] Table 1 As can be seen from the table above, the compounds provided by this invention have excellent thermal stability, hole mobility and solubility, and can be used as hole transport layers or electron blocking layers in organic electroluminescent devices to improve the luminous efficiency of the devices and extend their service life.

[0059] Fabrication of organic electroluminescent devices: 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. The ITO glass substrate was then 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 mentioned above, 4,4'-bis(9-carbazole)biphenyl (CBP) (as the host material for light emission, 90 wt%) and Ir(ppy)3 (as the guest material for light emission, 10 wt%) are co-vacuum-deposited to form a light emission layer with a thickness of 30 nm. On the above-mentioned light-emitting layer, compound 94 from Example 13 was synthesized by vacuum evaporation to form a 5 nm hole-blocking layer; On the aforementioned hole blocking layer, 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.

[0060] Device Examples 1 to Device Examples 7 Organic electroluminescent devices were prepared using the same method as in Device Example 1, except that the compounds synthesized in Synthesis Examples 14 to 18 and 20 were used to replace compound 94 prepared in Synthesis Example 13.

[0061] Device Comparison Example 1 An organic electroluminescent device was prepared using the same method as in Device Example 1, except that compound D2 was used to replace compound 94 prepared in Synthesis Example 13.

[0062] Device performance testing: The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Device Examples 1-7 and Device Comparative Example 1 of the present invention are shown in Table 2: Table 2 As can be seen from the table above, when the compound provided by the present invention is used as the light-emitting layer of an organic electroluminescent device, the driving voltage of the organic electroluminescent device can be reduced, the luminous efficiency of the device can be improved, and the service life of the device can be extended.

[0063] 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. An organic fused-ring compound, characterized in that, The compound has the structural formula shown in Formula 1: Wherein, A is a C5 to C6 aliphatic hydrocarbon ring, and R1 and R2 are independently selected from substituted or unsubstituted C6 to C6 hydrocarbon rings. 12 The aryl group, R1 and R2 are independent, or R1 and R2 are bonded together by single bonds to form a fused ring structure; The substituted C6 to C 12 The aryl group is C6 to C6. 12 One or more H atoms at any position on the aryl group are replaced by R', where R' is... m is selected from 0 or 1, and Ar1 is selected from C6 to C1. 12 The arylene group, R is selected from substituted or unsubstituted C1 to C4 alkyl groups, C6 to C4 alkyl groups. 30 aryl, C6 to C 30 Aromatic amino groups, C6 to C 30 heteroaryl groups; The substituted C6 to C 30 aryl, C6 to C 30 Aromatic amino groups, C6 to C 30 The substituents in the heteroaryl group are one or more of deuterium, cyano, C1-C4 alkyl, and phenyl.

2. The organic fused-ring compound according to claim 1, characterized in that, The same or different R1 and R2 are selected from substituted or unsubstituted monocyclic aryl groups, or substituted or unsubstituted polycyclic aryl groups formed by two monocyclic aryl groups through single bonds or fusion bonds; Ar1 is selected from monocyclic aryl groups and polycyclic aryl groups formed by two monocyclic aryl groups linked by a single bond or fusion bond.

3. The organic fused-ring compound according to claim 1, characterized in that, The fused ring structure formed by single-bond bonding between R1 and R2 has the following structural formula: , , , , The connection points of R1 and R2 in Equation 1 are given.

4. The organic fused-ring compound according to claim 1, characterized in that, The Ar1 is selected from phenylene, biphenylene, or naphthylene.

5. The organic fused-ring compound according to claim 1, characterized in that: The unsubstituted C6 to C 30 The aryl group is selected from R3 to R7 are each independently selected from H, C1-C4 alkyl or phenyl groups; R3 to R7 are independent of each other and are bonded to the central phenyl group by a single bond, or are fused together by a single bond between any two adjacent substituents in R3 to R7, or are fused together by 1-2 non-adjacent substituents in R3 to R7 with the central phenyl group. The unsubstituted C6 to C 30 heteroaryl groups selected from or Y2 is selected from N(R) 13 ), O or S; Y1, Z1-Z3 are each independently selected from CH or N, and Z1-Z3 are not simultaneously C; R8, R 13 Selected from H, C1-C4 alkyl or phenyl groups; R8 is linked by a single bond or fused with Y1 by sharing a pair of chemical bonds; R9, R 10 Selected from the groups shown in Formula 2 or Formula 3; The unsubstituted C6 to C 30 Aromatic amino groups are selected from R 11 To R 12 Each group is independently selected from the groups shown in Formula 2 or Formula 3; * indicates a connection point.

6. The organic fused-ring compound according to claim 5, characterized in that, The second formula is selected from , , , , , ; Formula 3 is selected from: , , , ; Formula 4 is selected from: , , , , , , , , ; The fifth formula is selected from , , , , , , , , , .

7. The organic fused-ring compound according to claim 1, characterized in that, A is selected from cyclopentane or cyclohexane.

8. The organic fused-ring compound according to claim 7, characterized in that, The organic fused-ring compound is selected from the following structural formulas: 。 9. An organic electroluminescent device, comprising a first electrode and a second electrode disposed opposite to each other, wherein an organic layer is disposed between the first electrode and the second electrode, characterized in that, The organic layer comprises the organic fused-ring compound according to any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, characterized in that, The organic 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. The organic layer containing an organic fused ring compound is a light-emitting layer, an electron transport layer, an electron blocking layer, a hole transport layer, or a hole blocking layer.

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