Organic semiconductor material containing eight-membered aza fused ring as well as preparation method and application of organic semiconductor material

Abstract

The invention discloses an organic semiconductor material containing an eight-membered aza fused ring as well as a preparation method and application of the organic semiconductor material. The structural formula of the organic semiconductor material containing the eight-membered aza fused ring is as shown in formula (I)-formula (IX). The organic semiconductor material containing the eight-membered aza fused ring can be used as a light-emitting material in an organic light-emitting diode, and has the characteristics of high-efficiency dark blue light emission and narrow half-peak width, so that an organic electroluminescent device with excellent photoelectric performance is obtained, and the application of organic electroluminescence in the field of ultra-high-definition display is finally realized.

Description

Technical Field

[0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to an organic semiconductor material containing an eight-membered nitrogen-fused ring, and a preparation method and application thereof. Background Art

[0002] With the continuous advancement of display technology, especially the increasing demand for ultra-high definition, wide color gamut and high resolution, higher requirements are placed on the color performance of display devices such as OLED. In application scenarios that have extremely high requirements for display effects, such as augmented reality, virtual reality, and wearable display devices, OLED screens need to have better color purity and display performance, so it is urgent to develop new high-performance organic semiconductor materials with narrow-band emission characteristics.

[0003] However, unlike the "narrow line" characteristics presented by atomic spectra, due to the relative vibration energy between atoms and the vibration and rotation energy of the molecule as a whole, its spectrum mostly presents "band" characteristics. Therefore, it is difficult to achieve ideal color purity and ideal display effects with traditional molecular design strategies. In recent years, through innovative molecular design and structural regulation, researchers have tried to narrow the emission bandwidth and improve color purity through multiple resonance effects and modification methods, but still face problems such as a single luminescent skeleton structure and few modifiable sites. Therefore, designing and developing new organic semiconductor materials with narrow-band emission and high color purity has become an important topic for the further development of OLED technology. Summary of the invention

[0004] In view of the deficiencies in the prior art, the purpose of the present invention is to provide an organic semiconductor material containing an eight-membered nitrogen-fused ring; the organic semiconductor material containing an eight-membered nitrogen-fused ring provided by the present invention has narrow-band emission characteristics and high color purity. The luminescent skeleton of the material adopts a unique eight-membered nitrogen-fused ring structure, which not only has high rigidity, but also has multiple modifiable sites, which is convenient for fine regulation of the molecular structure to optimize its optical properties. By rationally designing the structure of the eight-membered ring, the material can achieve a narrow spectral bandwidth, thereby effectively improving the color purity and display performance of OLED devices. Based on the fact that this type of organic semiconductor material has high solid-state luminescence efficiency, narrow-band emission and adjustable color performance, it can meet the needs of high-color purity OLED display devices, and provide important technical support for future high-end display technologies.

[0005] Another object of the present invention is to provide a method for preparing the above-mentioned organic semiconductor material containing eight-membered nitrogen-fused ring. The preparation method of the present invention has simple process, readily available raw materials and high yield.

[0006] Another object of the present invention is to provide an application of the above-mentioned organic semiconductor material containing an eight-membered nitrogen-fused ring in the field of organic electroluminescence, especially in the preparation of a light-emitting layer of an organic light-emitting diode.

[0007] The purpose of the present invention is achieved by at least one of the following technical solutions.

[0008] The present invention provides an organic semiconductor material containing an eight-membered nitrogen-fused ring, the structural formula of which is as follows:

[0009] wherein Z is independently C-R1 or N, and R1 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an aldehyde group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2~C60 heterocycloalkyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C1-C40 heteroalkoxy group, a substituted or unsubstituted C6~C60 aryl group, a substituted or unsubstituted C2~C60 hetero Aryl, substituted or unsubstituted C6~C60 aryloxy, substituted or unsubstituted C2~C60 heteroaryloxy, substituted or unsubstituted C1-C40 alkylamine, substituted or unsubstituted C1-C40 heteroalkylamine, substituted or unsubstituted C6~C60 arylamine, substituted or unsubstituted C2~C60 heteroarylamine, substituted or unsubstituted B1-B20 boryl, substituted or unsubstituted Si1-Si20 silyl, substituted or unsubstituted C6~C60 aromatic silicon, adjacent R1 are connected to form a ring or not; Substituted C1-C20 alkyl, substituted C1-C20 heteroalkyl, substituted C3-C60 cycloalkyl, substituted C2~C60 heterocycloalkyl, substituted C1-C40 alkoxy, substituted C1-C40 heteroalkoxy, substituted C6~C60 aryl, substituted C2~C60 heteroaryl, substituted C6~C60 aryloxy, substituted C2~C60 heteroaryloxy, substituted C1-C40 alkylamino, substituted C1-C40 heteroalkylamino, substituted C6~C6 The substituents in the substituted C2-C60 aromatic amine group, the substituted B1-B20 boryl group, the substituted Si1-Si20 silyl group, and the substituted C6-C60 aromatic silicon group are each independently selected from one or more of a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an aldehyde group, a C2-C10 acyl group, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aromatic group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C2-C30 heteroaryl group, and an amino group; V is carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; W is carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; X is a single bond, carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; Y is a single bond, carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; R2, R3, R4, R5, R6 and R7 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an aldehyde group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6~C60 aryl group, a substituted or unsubstituted C1-C40 alkylamino group, a substituted or unsubstituted C6~C60 arylamino group, a substituted or unsubstituted C2~C60 heteroarylamino group, a substituted or unsubstituted C2~C60 heterocycloalkyl group, R2 and R3 are connected to form a ring or are not connected, and R5 and R6 are connected to form a ring or are not connected; The substituents in the substituted C1-C20 alkyl, substituted C2-C40 alkenyl, substituted C1-C40 alkoxy, substituted C3-C60 cycloalkyl, substituted C6~C60 aryl, substituted C1-C40 alkylamino, substituted C6~C60 arylamino, substituted C2~C60 heteroarylamino, and substituted C2~C60 heterocycloalkyl are each independently selected from one or more of a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an aldehyde group, a C2-C10 acyl group, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C2-C30 heteroaryl group, and an amino group; When the adjacent Z of V, W, X, and Y is C-R1, R2, R3, R4, R5, R6, or R7 and R1 are connected to form a ring or are not connected.

[0010] In the present invention, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the substitution position is not limited as long as it is a position where a hydrogen atom is substituted, i.e., a position where a substituent can be substituted; "substituted" means replacement by one, two or more substituents, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0011] In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is preferably 1 to 20 (1, 3, 5, 10, 20, etc.). Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-di-methylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0012] In the present invention, the alkenyl group may be linear or branched, and the number of carbon atoms is preferably 2 to 40 (2, 4, 6, 10, 20, 30, 40, etc.). Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, etc., but are not limited thereto.

[0013] In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is preferably 1 to 40 (1, 3, 5, 10, 20, 30, 40, etc.). Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but are not limited thereto.

[0014] The alkyl groups, alkoxy groups and other substituents containing an alkyl moiety described in the present invention include both linear and branched forms.

[0015] In the present invention, the cycloalkyl group preferably has 3 to 60 carbon atoms, and according to one embodiment, the carbon number of the cycloalkyl group is 3 to 40. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0016] In the present invention, the alkylamine group preferably has 1 to 40 (1, 3, 5, 10, 20, 30, 40, etc.) carbon atoms, and specific examples of the alkylamine group may include methylamine group, dimethylamine group, ethylamine group, diethylamine group, etc., but are not limited thereto.

[0017] In the present invention, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl in the arylamine group can be a monocyclic aryl or a polycyclic aryl. The arylamine group comprising two or more aryl groups can include a monocyclic aryl, a polycyclic aryl, or both a monocyclic aryl and a polycyclic aryl. The specific examples of arylamine groups can include aniline, naphthylamine, benzidine, anthraceneamine, 3-methyl-aniline, 4-methyl-naphthylamine, 2-methyl-benzidine, 9-methyl-anthrylamine, diphenylamine, phenylnaphthylamine, dimethylphenylamine, phenylmethylphenylamine, carbazole, triphenylamine, etc., but are not limited thereto.

[0018] In the present invention, the example of heteroarylamine can include substituted or unsubstituted monoheteroarylamine, substituted or unsubstituted diheteroarylamine or substituted or unsubstituted triheteroarylamine. The heteroaryl in the heteroarylamine can be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine comprising two or more heterocyclic groups can include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or both a monocyclic heterocyclic group and a polycyclic heterocyclic group.

[0019] In the present invention, the aryl group preferably has 6 to 60 carbon atoms (6, 10, 20, 30, 40, 50, 60, etc.), and may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, examples thereof may include phenyl, biphenyl, terphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups may include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, triphenyl, fluorenyl, etc., but are not limited thereto.

[0020] In the present invention, "adjacent" groups may refer to any one or a combination of the following two situations: (1) structurally adjacent, where the substituents are respectively connected to two atoms that are directly bonded, such as ortho-substituents on a benzene ring; (2) spatially adjacent, where the substituents are closest in the three-dimensional spatial configuration, such as, but not limited to, V, W, X, and Y connected to form a ring; In the present invention, the "ring" in the substituted or unsubstituted ring formed by adjacent groups bonding to each other means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0021] In the present invention, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of aromatic and aliphatic groups, and may be selected from examples of the cycloalkyl group or aryl group except for non-monovalent cycloalkyl group or aryl group.

[0022] In the present invention, the description about the aryl group can be applied to the aromatic ring, except that the aromatic ring is monovalent.

[0023] In the present invention, the heterocycle contains one or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, S, and Se. The heterocycle may be a monocyclic or polycyclic aromatic ring, an aliphatic ring, or an aromatic and aliphatic fused ring, and may be selected from examples of heteroaryl groups, excluding non-monovalent heteroaryl groups.

[0024] Preferably, the structural formula of the organic semiconductor material containing an eight-membered nitrogen-fused ring is as follows:

[0025]

[0026]

[0027]

[0028] .

[0030] The above-mentioned organic semiconductor material containing eight-membered nitrogen-fused ring is prepared by the following method: The substituents can be bonded using methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0031] The present invention provides a method for preparing the above-mentioned organic semiconductor material containing an eight-membered nitrogen-fused ring. The preparation method of the compound represented by formula (I) comprises the following steps: (1) Compound 1 and compound 2 undergo carbon-carbon coupling reaction to obtain compound 3;

[0032] (2) Compound 3 and compound 4 undergo nucleophilic substitution reaction to construct an eight-membered ring to obtain compound 5;

[0033] (3) Compound 5 is subjected to a nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain a compound represented by formula (I);

[0034] The preparation method of the compound represented by formula (II) comprises the following steps: (4) subjecting the secondary amine site of the compound represented by formula (I) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (II);

[0035] The preparation method of the compound represented by formula (III) comprises the following steps: (5) The secondary amine site of compound 7 undergoes nucleophilic substitution reaction with compound 8 to obtain compound 9;

[0036] (6) Compound 9 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (III);

[0037] The preparation method of the compound represented by formula (IV) comprises the following steps: (7) The secondary amine site of compound 10 undergoes a nucleophilic substitution reaction with compound 11 to obtain compound 12;

[0038] (8) Compound 12 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (IV);

[0039] The preparation method of the compound represented by formula (V) comprises the following steps: (9) Compound 13 and compound 14 undergo carbon-carbon coupling reaction to obtain compound 15;

[0040] (10) Compound 15 and compound 16 undergo nucleophilic substitution reaction to construct an eight-membered ring to obtain compound 17;

[0041] (11) Compound 17 was subjected to nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain compound 18;

[0042] (12) Compound 18 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (V);

[0043] The preparation method of the compound represented by formula (VI) comprises the following steps: (13) The secondary amine site of compound 19 undergoes nucleophilic substitution reaction with compound 20 to obtain compound 21;

[0044] (14) Compound 21 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (VI); .

[0045] The preparation method of the compound represented by formula (VII) comprises the following steps: (15) Compound 22 and compound 23 were reacted by carbon-carbon coupling reaction to obtain compound 24;

[0046] (16) Compound 24 reacts with compound 25 via nucleophilic substitution to give compound 26;

[0047] (17) Compound 26 was subjected to nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain compound 27;

[0048] (18) Compound 27 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (VII);

[0049] The preparation method of the compound represented by formula (VIII) comprises the following steps: (19) subjecting the secondary amine site of the compound represented by formula (VII) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (VIII);

[0050] The preparation method of the compound represented by formula (IX) comprises the following steps: (20) subjecting the secondary amine site of the compound represented by formula (V) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (IX);

[0051] Preferably, the temperature of the carbon-carbon coupling reaction in step (1) is 100-110° C. and the time is 8-12 h; Preferably, the temperature of the nucleophilic substitution reaction in step (2) is 140-150° C. and the time is 4-8 hours; Preferably, the temperature of the nitro ring-bonding reaction in step (3) is 150-180° C. and the time is 4-8 hours.

[0052] Preferably, the temperature of the Buchwald-Hartwig coupling reaction in step (4) is 120-140° C., and the time is 4-8 h.

[0053] Preferably, the temperature of the nucleophilic substitution reaction in step (5) is 140-150° C. and the time is 4-8 hours; Preferably, the temperature of the cyclization reaction in step (6) is -40 to 210°C and the time is 24 to 48 hours; Preferably, the temperature of the nucleophilic substitution reaction in step (7) is 140-150° C. and the time is 4-8 h; Preferably, the temperature of the cyclization reaction in step (8) is -40 to 210° C., and the time is 24 to 48 hours.

[0054] Preferably, the temperature of the carbon-carbon coupling reaction in step (9) is 100-110° C. and the time is 8-12 h.

[0055] Preferably, the temperature of the nucleophilic substitution reaction in step (10) is 140-150° C. and the time is 4-8 hours; Preferably, the temperature of the nitro ring-bonding reaction in step (11) is 150-180° C. and the time is 4-8 hours; Preferably, the temperature of the cyclization reaction in step (12) is -40 to 210° C., and the time is 24 to 48 hours.

[0056] Preferably, the temperature of the nucleophilic substitution reaction in step (13) is 140-150° C. and the time is 4-8 h; Preferably, the temperature of the cyclization reaction in step (14) is -40 to 210° C., and the time is 24 to 48 hours.

[0057] Preferably, the temperature of the carbon-carbon coupling reaction in step (15) is 100-110° C. and the time is 8-12 h; Preferably, the temperature of the nucleophilic substitution reaction in step (16) is 140-150° C. and the time is 4-8 h; Preferably, the temperature of the nitro ring-bonding reaction in step (17) is 150-180° C. and the time is 4-8 hours.

[0058] Preferably, the temperature of the cyclization reaction in step (18) is -40 to 210° C., and the time is 24 to 48 hours.

[0059] Preferably, the temperature of the Buchwald-Hartwig coupling reaction in step (19) is 120-140° C., and the time is 4-8 h.

[0060] Preferably, the temperature of the Buchwald-Hartwig coupling reaction in step (20) is 120-140° C., and the time is 4-8 h.

[0061] Preferably, the molar ratio of compound 1 to compound 2 in step (1) is 1:2 to 1:2.5.

[0062] Preferably, the molar ratio of compound 3 to compound 4 in step (2) is 1:1.5 to 1:2; Preferably, the molar ratio of the compound represented by formula (I) in step (4) to compound 6 is 1:2 to 1:2.5.

[0063] Preferably, in step (5), the molar ratio of compound 7 to compound 8 is 1:1.5 to 1:2;.

[0064] Preferably, in step (7), the molar ratio of compound 10 to compound 11 is 1:1.5 to 1:2;.

[0065] Preferably, in step (9), the molar ratio of compound 13 to compound 14 is 1:2 to 1:2.5.

[0066] Preferably, in step (10), the molar ratio of compound 15 to compound 16 is 1:1.5 to 1:2; Preferably, in step (13), the molar ratio of compound 19 to compound 20 is 1:1.5 to 1:2.

[0067] Preferably, in step (15), the molar ratio of compound 22 to compound 23 is 1:2 to 1:2.5.

[0068] Preferably, in step (16), the molar ratio of compound 24 to compound 25 is 1:1.5 to 1:2; Preferably, the molar ratio of the compound represented by formula (VII) in step (19) to compound 6 is 1:2 to 1:2.5.

[0069] Preferably, the molar ratio of the compound represented by formula (V) in step (20) to compound 6 is 1:2 to 1:2.5.

[0070] The present invention provides an application of the above-mentioned organic semiconductor material containing an eight-membered nitrogen-fused ring in the preparation of an organic electroluminescent device.

[0071] Preferably, an organic semiconductor material containing an eight-membered nitrogen-fused ring is used as the light-emitting material.

[0072] The present invention selects an eight-membered nitrogen-fused ring as the core building block, which is a luminescent unit with multiple resonance effects and an excellent rigid skeleton structure, which can effectively reduce the coupling effect between electrons and vibrations, thereby achieving spectrum narrowing. At the same time, thanks to its simple preparation method, the synthetic raw materials of the building block have rich substrate expansion, thereby achieving the diversification of modifiable sites.

[0073] In addition, more importantly, the present invention discovered for the first time that the new core building block has a main peak in the luminescence spectrum of its original skeleton in the deep blue light range, which indicates that it can be used as an excellent donor to realize the construction of full-spectrum organic semiconductor materials. In addition, this type of material has thermally activated delayed fluorescence characteristics and can achieve efficient exciton utilization efficiency during electroluminescence. Therefore, based on this type of material, high-efficiency, high-color purity organic electroluminescent devices can be prepared. Moreover, the synthesis method of this type of material is efficient, and the thermal stability and electrochemical stability are excellent, so that this type of material can be synthesized and purified on a large scale, and has broad application prospects in the field of organic electroluminescence.

[0074] Compared with the prior art, the present invention has the following advantages and beneficial effects: (1) The organic semiconductor material containing an eight-membered nitrogen-fused ring of the present invention has a narrowed spectrum, high solid-state luminescence efficiency, and high exciton utilization efficiency, and can be used to prepare an organic electroluminescent device with high efficiency and high color purity.

[0075] (2) The synthesis method of the organic semiconductor material containing an eight-membered nitrogen-fused ring of the present invention is simple, the raw materials are easily available, the yield is high, and the obtained material has a stable structure.

[0076] (3) The organic semiconductor material containing an eight-membered nitrogen-fused ring of the present invention is used for the light-emitting layer of an organic light-emitting diode, has excellent overall performance, and can be widely used in the field of organic electroluminescence. BRIEF DESCRIPTION OF THE DRAWINGS

[0077] Figure 1a The UV absorption spectrum and fluorescence emission spectrum of the 8NN compound in Example 4 in toluene solution.

[0078] Figure 1b The UV absorption spectrum and fluorescence emission spectrum of the 8NNP compound in Example 4 in toluene solution.

[0079] Figure 1c The UV absorption spectrum and fluorescence emission spectrum of the 8NNB compound in Example 4 in toluene solution.

[0080] Figure 1d This is the fluorescence emission spectrum of the NDCZ compound in comparative example 1 in toluene solution.

[0081] Figure 2a This is the electroluminescence spectrum of the doped OLEDs device prepared with the 8NNP compound in Example 5.

[0082] Figure 2b This is a curve chart showing the variation of efficiency with brightness of the doped OLEDs device prepared using the 8NNP compound in Example 5.

[0083] Figure 2c This is the JVL curve of the doped OLEDs device prepared with the 8NNP compound in Example 5.

[0084] Figure 3a This is the electroluminescence spectrum of the doped OLEDs device prepared with the 8NNB compound in Example 5.

[0085] Figure 3b This is a curve chart showing the variation of efficiency with brightness of the doped OLEDs device prepared with the 8NNB compound in Example 5.

[0086] Figure 3c This is the JVL curve of the doped OLEDs device prepared with the 8NNB compound in Example 5. DETAILED DESCRIPTION

[0087] The specific implementation of the present invention is further described below in conjunction with examples, but the implementation and protection of the present invention are not limited thereto. It should be noted that if there are processes that are not particularly described in detail below, they can be implemented or understood by those skilled in the art with reference to the prior art. If the manufacturer of the reagents or instruments used is not indicated, they are deemed to be conventional products that can be purchased commercially.

[0088] Example 1: Preparation of organic semiconductor material containing eight-membered nitrogen-condensed ring (8NN): The structural formula of 8NN is as follows:

[0089] Reaction equation (I):

[0090] (1) First, take a three-necked flask, weigh 2.19 g (10 mmol) of 2-bromo-3-fluoronitrobenzene, 2.1 g (15 mmol) of 2-fluorophenylboric acid, 577.5 mg (0.5 mmol) of tetrakistriphenylphosphine palladium, and 11.04 g (80 mmol) of potassium carbonate, and place them in the three-necked flask. Then, install the reaction device, seal it, and evacuate the air. After evacuating the air for 10 minutes, introduce nitrogen into the device. Repeat this operation three times to remove all the air in the device. During the evacuation process, take a flask, use a syringe to extract 80 mL of N,N-dimethylformamide and 20 mL of deionized water, place them in the flask, and pass nitrogen to deoxygenate for 20 minutes. After the oxygen is completely removed, use a syringe to inject the solvent (80 mL of N,N-dimethylformamide and 20 mL of deionized water) that has been deionized into the three-necked flask. Heat the mixture to 150 °C under the protection of a nitrogen flow, with a rotor speed of 400 rpm, and stir for 24 hours. After the reaction, the reaction system was subjected to rotary evaporation to remove the solvent, and then extracted with dichloromethane and deionized water. After receiving the organic phase, the crude product was pulverized and separated and purified by column chromatography. The solution obtained by chromatography was subjected to rotary evaporation and suction filtration to obtain a yellow powder of N2F (2.10 g). 1 HNMR (400 MHz, CD2Cl2) δ 7.86 (d, J = 8.2 Hz, 1H), 7.58 (td, J = 8.3, 5.5 Hz, 1H),7.53 – 7.42 (m, 2H), 7.29 (ddt, J = 8.5, 7.6, 4.0 Hz, 2H), 7.24 – 7.16 (m, 1H). (2) First, take a three-necked flask, weigh about 2.35 g (10 mmol) of the intermediate product N2F, 3.84 g (15 mmol) of indole[2,3-a]carbazole, and 5.76 g (30 mmol) of cesium carbonate and place them in the three-necked flask. Then install the reaction device, seal and evacuate. After evacuating for 10 minutes, introduce nitrogen into the device. Repeat this operation three times to remove all the air in the device. During the evacuation process, take a flask, place N,N-dimethylformamide in the flask, and pass nitrogen to deoxygenate. After the oxygen is completely removed, use a syringe to inject 50 mL of solvent (N,N-dimethylformamide) that has been completely evacuated into the three-necked flask, and stir for 20 minutes under the protection of nitrogen flow. Then heat the mixture to 150 °C, with the rotor speed at 400 rpm, and stir for 24 hours. After the reaction, the reaction system was subjected to rotary evaporation to remove the solvent, and then extracted with dichloromethane and deionized water. After receiving the organic phase, the crude product was pulverized and separated and purified by column chromatography. The solution obtained by chromatography was subjected to rotary evaporation and suction filtration to obtain a brown powder of NDCZ (3.22 g). 1 H NMR (500 MHz, CD2Cl2) δ 8.14 (dd, J = 9.7, 3.7 Hz, 2H), 8.03 –7.94 (m, 2H), 7.79 (dd, J = 8.0, 1.1 Hz, 1H), 7.68 (d, J = 8.1 Hz, 1H), 7.54 (d, J = 8.1 Hz, 1H), 7.51 – 7.31 (m, 8H), 7.27 (dd, J = 8.3, 1.1 Hz, 1H), 7.03 (dd, J =7.8, 1.4 Hz, 1H). (3) First, prepare a flask, place o-dichlorobenzene in the flask, pass nitrogen to deoxygenate, and draw 80 mL of o-dichlorobenzene with a syringe. At the same time, prepare a double-necked flask, weigh 4.52 g (10 mmol) of NDCZ and 7.86 g (30 mmol) of triphenylphosphine, place them in it, install the reaction device, seal and evacuate. After evacuating for 10 minutes, pass nitrogen into the device, and repeat the operation three times to remove all the air in the device. After the oxygen is completely removed, use a syringe to inject the solvent (o-dichlorobenzene) that has been depleted of air into the double-necked flask, then raise the temperature to 180 °C under a nitrogen atmosphere, rotate the rotor at 400 rpm, and stir for 24 hours. After the reaction is completed, dilute the mixture with dichloromethane and wash it with water three times. Then, dry the diluted solution with MgSO4 for 15 minutes. After drying, remove the remaining solvent by rotary evaporation. The crude product was then pulverized and purified by silica gel column chromatography. The solution obtained by chromatography was rotary evaporated and filtered to obtain the target product 8NN (1.50 g) as a light yellow solid. 1 H NMR (400 MHz, CD2Cl2) δ 8.62 (s, 1H), 8.21 (d, J = 5.6 Hz, 2H), 8.18 (dd, J = 6.2, 2.7 Hz, 2H),7.59 – 7.54 (m, 2H), 7.52 – 7.40 (m, 6H), 7.35 – 7.28 (m, 4H). Example 2: Preparation of organic semiconductor material containing eight-membered nitrogen-condensed ring (8NNP): The structural formula of 8NNP is as follows:

[0091] Reaction equation (II):

[0092] (1) The product 8NN of Example 1 was synthesized into the final product 8NNP by using the Ullmann reaction.

[0093] First, take a three-necked flask, weigh about 4.19 g (10 mmol) of the intermediate product 8NN, 190.45 mg (1 mmol) of cuprous iodide, 115 mg (1 mmol) of L-proline, and 2.76 g (20 mmol) of potassium carbonate and place them in the three-necked flask, then install the reaction device, seal and evacuate. After evacuating for 10 minutes, introduce nitrogen into the device, and repeat this operation three times to remove all the air in the device. During the evacuation process, take a flask, place dimethyl sulfoxide in the flask, and pass nitrogen to deoxygenate. After the oxygen is completely removed, use a syringe to inject 50 mL of solvent (dimethyl sulfoxide) that has been completely evacuated into the three-necked flask, stir for 2-3 minutes under the protection of nitrogen flow, and then add 7.80 g (50 mmol) of bromobenzene. Then heat the mixture to 195 ° C, the rotor speed is 400 rpm, and stir for 12 hours. After the reaction, the reaction system was subjected to rotary evaporation to remove the solvent, and then extracted with dichloromethane and deionized water. After receiving the organic phase, the crude product was pulverized and separated and purified by column chromatography. The solution obtained by chromatography was subjected to rotary evaporation and suction filtration to obtain a white powder (4.55 g). 8NNP was obtained as a white solid with a yield of 92%. 1 H NMR (400MHz, THF) δ 8.23 ​​(d, J = 6.8 Hz, 2H), 8.21 (dd, J = 5.9, 3.0 Hz, 2H), 7.75 (dt, J =15.2, 7.7 Hz, 4H), 7.60 (t, J = 7.2 Hz, 1H), 7.55 (dd, J = 5.8, 3.3 Hz, 2H), 7.47(t, J = 6.8 Hz, 4H), 7.35 – 7.31 (m, 2H), 7.28 (dd, J = 6.0, 3.0 Hz, 4H). Example 3: Preparation of organic semiconductor material containing eight-membered nitrogen-condensed ring (8NNB): The structural formula of 8NNB is as follows:

[0094] Reaction equation (III):

[0095] (1) A mixture of compound 8NN (4.19 g, 10 mmol) and cesium carbonate (3.86 g, 20 mmol) was placed in a 100 mL round-bottom flask under nitrogen. Then, 25 mL of N,N-dimethylformamide (DMF) was injected into the flask, and the mixture was stirred at room temperature for 30 min. Then, o-bromofluorobenzene (8.75 g, 50 mmol) was injected into the reaction flask, and the mixture was stirred at 150 °C for 24 h under a nitrogen atmosphere. When the reaction was cooled to room temperature, the mixture was poured into an aqueous solution and extracted several times with dichloromethane. The extract was dried over anhydrous MgSO4 and evaporated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (petroleum ether / DCM, 4:1). 8NNPBr was obtained as a white solid with a yield of 62%. 1 H NMR (500 MHz, CD2Cl2)δ 8.26 – 8.18 (m, 4H), 7.98 (dd, J = 8.1, 1.2 Hz, 1H), 7.72 – 7.46 (m, 9H),7.37 – 7.30 (m, 4H), 7.09 – 6.93 (m, 2H).

[0096] (2) Under nitrogen protection, 8NNPBr (1.72 g, 3 mmol) and 50 ml of ultra-dry tert-butylbenzene were added to a 125 ml three-necked round-bottom flask. The solution was cooled to -40 °C, and then a solution of n-butyllithium (2.2 ml, 2.50 M, 5.5 mmol) in n-hexane was added, and the mixture was stirred at 60 °C for 2 h. After adding BBr3 (1.38 g, 5.5 mmol) at 0 °C, the temperature was raised to 150 °C and the reaction mixture was stirred for 12 h. Then the temperature was lowered to 0 °C, N,N-diisopropylethylamine (1.15 ml, 6.6 mmol) was added, and the reaction mixture was heated at 150 °C for 4 h. After cooling to 0 °C, trimethylmagnesium bromide (11 ml, 1.0 M, 11 mmol) dissolved in tetrahydrofuran was added, and the reaction mixture was stirred at room temperature for 12 h. The solvent was removed under reduced pressure, and the crude product was dissolved in dichloromethane and washed with water and brine. The organic layer was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The product was purified using silica gel flash chromatography (10:1 petroleum ether: CH2Cl2 as eluent) to give 1.18 g of 8NNB as a yellow solid (yield 63%). 1 H NMR (400 MHz, CD2Cl2) δ 8.86 (d, J = 8.5 Hz, 1H), 8.62 – 8.47 (m, 1H), 8.32 – 8.10 (m, 4H), 8.08 – 7.87 (m, 3H), 7.70 (dd,J = 21.0, 6.1 Hz, 3H), 7.60– 7.48 (m, 2H), 7.46 – 7.23 (m, 5H), 7.00 (d, J = 34.1 Hz, 2H), 2.41 (s, 3H), 2.21 (s, 3H), 1.98 (s, 3H). Example 4: Testing of UV absorption and fluorescence emission spectra of organic semiconductor materials containing eight-membered nitrogen-fused rings Weigh 2.08 mg of 8NN compound and dissolve it in 5 mL of HPLC grade toluene (TOL) to make a concentration of 10 -3 mol / L test sample. Take 30μL of 8NN test sample and add it to a 5mL centrifuge tube, then add 2970μL of pure HPLC grade TOL, stir evenly with an oscillator and transfer to a quartz cuvette. At the same time, take another 3 mL of pure HPLC grade TOL and place it in a quartz cuvette as a blank control group, followed by the determination of the UV absorption spectrum. Then take out the quartz cuvette of the experimental group and put it into the fluorescence spectrometer; test at the corresponding maximum excitation wavelength. Finally, the UV absorption spectrum and fluorescence emission spectrum of compound 8NN are obtained by processing the above data.

[0097] The testing methods for the UV absorption and fluorescence emission spectra of 8NNP and 8NNB compounds are the same as above.

[0098] The UV absorption spectra and fluorescence emission spectra of 8NN, 8NNP and 8NNB compounds correspond to Figure 1a , Figure 1b and Figure 1c .

[0099] from Figure 1a It can be seen that the ultraviolet absorption spectrum of the 8NN compound shows an obvious absorption peak caused by the short-range charge transfer state above 380 nm (the maximum absorption peak is at 398 nm); its emission spectrum in dilute toluene solution has obvious narrow emission properties, with its main peak at 408 nm and a half-peak width of 19 nm. The value of its spectrum in CIE 1931 color coordinates is (0.165, 0.011), which is extremely low CIE y The value reflects the extremely high purity of deep blue light. In addition, the fluorescence quantum efficiency of the single molecule state in the molecular solution is 27.3%.

[0100] from Figure 1bIt can be seen that the ultraviolet absorption spectrum of the 8NNP compound shows an obvious absorption peak caused by the short-range charge transfer state above 390nm (the maximum absorption peak is at 402nm); at the same time, it has obvious deep blue light emission properties, with the main peak located at 411nm and a narrow half-peak width of 17nm in toluene solution. The luminescence efficiency of 8NNP in toluene solution is 33.6%. Compared with the emission spectrum of the 8NN compound, the peak position of 8NNP is close to its performance, indicating that the introduction of the rotor structure of the peripheral benzene ring has little effect on the electronic structure of the molecular core skeleton, which retains the luminescence properties of the skeleton itself. More importantly, the half-peak width of the emission spectrum of 8NNP in toluene solution is significantly narrowed to 17nm, and the value of its spectrum in the CIE 1931 color coordinates is (0.163, 0.014), which also reflects the extremely high deep blue light color purity characteristics.

[0101] The molecule 8NNB is further cyclized by 8NNP to construct an organic semiconductor material with pure blue light emission and narrow band characteristics.

[0102] from Figure 1c It can be seen that the ultraviolet absorption spectrum of the 8NNB compound shows an obvious absorption peak caused by the short-range charge transfer state above 420nm. Compared with 8NNP and 8NN, the short-range absorption maximum peak of 8NNB in ​​dilute toluene solution is further red-shifted to 440nm. At the same time, the introduction of boron atoms enhances the delocalization of the electron cloud, so that the peak of the emission spectrum is also red-shifted to the positive blue light range, with a peak of 461nm; its half-peak width also realizes the narrow-band emission characteristics, which is 31 nm. The value of its spectrum in the CIE 1931 color coordinates is (0.131, 0.102), reflecting the high blue light color purity characteristics. In order to reduce the damage of harmful blue light to the human eye, the blue light pixel points of display technology usually require the main peak of the blue light material to be around 460nm. The main peak of 8NNB formed after cyclization meets the actual needs of display technology, and also reflects that the eight-membered nitrogen-containing fused ring structure has good modifiability and can effectively realize the regulation of light color. The luminescence efficiency of 8NNB in ​​toluene solution is 50.6%.

[0103] Based on the above, it is strongly proved that the multi-resonance skeleton containing the eight-membered nitrogen-fused ring structure can achieve narrow-band emission characteristics, thereby obtaining organic semiconductor materials with high color purity and achieving high color purity organic semiconductor device performance.

[0104] Comparative Example 1: Testing of the fluorescence emission spectrum of the comparative molecule NDCZ compound The test method is the same as in Example 4. The data is processed to obtain the fluorescence emission spectrum of the NDCZ compound, corresponding to Figure 1d The NDCZ compound is an intermediate before the 8NN compound is fused.

[0105] from Figure 1d It can be seen that compared with the 8NN compound, the main emission peak of the precursor compound NDCZ in toluene solution is 388 nm, which is the ultraviolet emission band. At the same time, it has a wide half-peak width of 40 nm. In particular, an obvious shoulder peak is shown at 475 nm in the spectrum, which greatly reduces its color purity. The above results strongly prove that the 8NN-type eight-membered nitrogen heterocyclic fused aromatic structure can achieve good narrow emission characteristics with the support of three pyrrole-type N atoms, further proving the advantages of this type of structure in realizing high-color-purity organic semiconductor light-emitting materials.

[0106] Example 5: OLED device performance of organic semiconductor materials containing eight-membered nitrogen-fused rings The doped device was prepared using the organic semiconductor materials 8NNP and 8NNB containing eight-membered nitrogen-fused rings prepared in Examples 2 and 3 (the wavelengths of deep blue light in single-molecule solution state were 411 nm and 461 nm, and the half-peak widths were 17 nm and 31 nm, respectively) as light-emitting materials.

[0107] (1) Doped device structure of 8NNP compound: ITO / HATCN (5 nm) / TAPC (50 nm) / TCTA (5 nm) / mcp (5 nm) / PPF: 3 wt% 8NNP (20 nm) / PPF (5 nm) / TmPyPB (30 nm) / LiF (1 nm) / Al (120 nm).

[0108] Among them, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4''-tri(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tri(3-pyridin-3-phenyl)benzene (TmPyPB) and LiF are used as hole injection layer, hole transport layer, exciton blocking layer, electron transport layer and electron injection layer respectively; 9,9'-(1,3-phenyl)di-9H-carbazole (mcp) and 2,8-bis(diphenylphosphoryl)dibenzo[B,D]furan (PPF) are used as electron blocking layer and hole blocking layer respectively. The device performance is tested and characterized, and the results are shown in Figure 2a , Figure 2b and Figure 2c .

[0109] Figure 2aThis is the electroluminescence spectrum of the doped OLEDs device prepared with 8NNP compound. As can be seen from the figure, the doped device based on 8NNP still retains the characteristics of photoluminescence in the single molecule state during the electroluminescence process, with a main peak of 418nm and a half-peak width of 18nm; the CIE color coordinates are (0.164, 0.023), showing excellent deep blue light color purity.

[0110] Figure 2b The efficiency of the doped OLEDs device prepared by the 8NNP compound changes with the brightness. It can be seen from the figure that the maximum external quantum efficiency of the doped device based on 8NNP is 2.52%.

[0111] Figure 2c The JVL curve of the doped OLEDs device prepared by 8NNP compound. It can be seen from the figure that the maximum brightness and start-up voltage of the doped device based on 8NNP are 264 cd / m 2 , 3.4 V.

[0112] (2) Doped device structure of 8NNB compound: ITO / HATCN (5 nm) / TAPC (50 nm) / TCTA (5 nm) / mcp (5 nm) / PPF: 3 wt% 8NNB (20 nm) / PPF (5 nm) / TmPyPB (30 nm) / LiF (1 nm) / Al (120 nm).

[0113] Among them, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HATCN), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4''-tri(carbazole-9-yl)triphenylamine (TCTA), 1,3,5-tri(3-pyridine-3-phenyl)benzene (TmPyPB) and LiF are used as hole injection layer, hole transport layer, exciton blocking layer, electron transport layer and electron injection layer respectively; 9,9'-(1,3-phenyl)di-9H-carbazole (mcp) and 2,8-bis(diphenylphosphoryl)dibenzo[B,D]furan (PPF) are used as electron blocking layer and hole blocking layer respectively. The device performance is tested and characterized, and the results are shown in Figure 3a , Figure 3b and Figure 3c .

[0114] Figure 3aThis is the electroluminescence spectrum of the doped OLEDs device prepared with 8NNB compound. As can be seen from the figure, the half-peak width of the doped device based on 8NNB during the electroluminescence process is further widened to 48nm, and its main peak is 476nm, CIE coordinates (0.131, 0.238). Although the boronized structure is susceptible to the external polar field effect after doping, resulting in an increase in peak width, the main peak is located in the positive blue light emission range and still reflects the characteristics of narrow-band emission.

[0115] Figure 3b The efficiency of the doped OLEDs device prepared by the 8NNB compound changes with the brightness. It can be seen from the figure that the maximum external quantum efficiency of the doped device based on 8NNB has increased significantly to 20.01%.

[0116] Figure 3c The JVL curve of the doped OLEDs device prepared by 8NNB compound. It can be seen from the figure that compared with 8NNP, the brightness of the doped device based on 8NNB is higher, with a value of 4718 cd / m 2 , the start-up voltage is 3.4V.

[0117] The above data show that the present invention is based on an eight-membered nitrogen-fused ring skeleton with multiple resonance characteristics, which exhibits excellent narrow-band emission characteristics in the photoluminescence process, and obtains an organic semiconductor light-emitting device with high color purity in the electroluminescence process. In particular, thanks to its simple preparation method, the synthetic raw materials of the building block have rich substrate expansion, thereby achieving the diversification of modifiable sites, which shows that it can be used as an excellent donor to achieve the construction of full-spectrum organic semiconductor materials. In addition, this type of material has the characteristics of thermally activated delayed fluorescence, breaking through the 25% exciton utilization limit of traditional fluorescent materials in the electroluminescence process, thereby obtaining a further improvement in the exciton utilization rate. This type of material has the characteristics of high solid-state luminescence efficiency, high electrically excited exciton utilization rate and narrow-band emission, and can prepare organic electroluminescent devices with high efficiency and high color purity.

[0118] Therefore, organic electroluminescent devices made of this type of organic semiconductor materials have broad application prospects in the field of ultra-high-definition displays.

[0119] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Changes, substitutions, modifications, etc. made by those skilled in the art without departing from the spirit of the present invention should fall within the protection scope of the present invention.

Claims

1. An organic semiconductor material containing an eight-membered nitrogen-fused ring, characterized in that: The structural formula is as follows: wherein Z is independently C-R1 or N, and R1 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an aldehyde group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 heteroalkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2~C60 heterocycloalkyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C1-C40 heteroalkoxy group, a substituted or unsubstituted C6~C60 aryl group, a substituted or unsubstituted C2~C60 hetero Aryl, substituted or unsubstituted C6~C60 aryloxy, substituted or unsubstituted C2~C60 heteroaryloxy, substituted or unsubstituted C1-C40 alkylamine, substituted or unsubstituted C1-C40 heteroalkylamine, substituted or unsubstituted C6~C60 arylamine, substituted or unsubstituted C2~C60 heteroarylamine, substituted or unsubstituted B1-B20 boryl, substituted or unsubstituted Si1-Si20 silyl, substituted or unsubstituted C6~C60 aromatic silicon, adjacent R1 are connected to form a ring or not; Substituted C1-C20 alkyl, substituted C1-C20 heteroalkyl, substituted C3-C60 cycloalkyl, substituted C2~C60 heterocycloalkyl, substituted C1-C40 alkoxy, substituted C1-C40 heteroalkoxy, substituted C6~C60 aryl, substituted C2~C60 heteroaryl, substituted C6~C60 aryloxy, substituted C2~C60 heteroaryloxy, substituted C1-C40 alkylamino, substituted C1-C40 heteroalkylamino, substituted C6~C6 The substituents in the substituted C2-C60 aromatic amine group, the substituted B1-B20 boryl group, the substituted Si1-Si20 silyl group, and the substituted C6-C60 aromatic silicon group are each independently selected from one or more of a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an aldehyde group, a C2-C10 acyl group, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aromatic group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C2-C30 heteroaryl group, and an amino group; V is carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; W is carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; X is a single bond, carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; Y is a single bond, carbon-R2R3, nitrogen-R4, silicon-R5R6, boron-R7, oxygen, sulfur or selenium; R2, R3, R4, R5, R6 and R7 are each independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an aldehyde group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C1-C40 alkoxy group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6~C60 aryl group, a substituted or unsubstituted C1-C40 alkylamino group, a substituted or unsubstituted C6~C60 arylamino group, a substituted or unsubstituted C2~C60 heteroarylamino group, a substituted or unsubstituted C2~C60 heterocycloalkyl group, R2 and R3 are connected to form a ring or are not connected, and R5 and R6 are connected to form a ring or are not connected; The substituents in the substituted C1-C20 alkyl, substituted C2-C40 alkenyl, substituted C1-C40 alkoxy, substituted C3-C60 cycloalkyl, substituted C6~C60 aryl, substituted C1-C40 alkylamino, substituted C6~C60 arylamino, substituted C2~C60 heteroarylamino, and substituted C2~C60 heterocycloalkyl are each independently selected from one or more of a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an aldehyde group, a C2-C10 acyl group, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C10 alkoxy group, a C6-C30 aryl group, a C6-C30 aryloxy group, a C2-C30 heteroaryl group, and an amino group; When the adjacent Z of V, W, X, or Y is C-R1, R2, R3, R4, R5, R6, or R7 and the adjacent R1 may be connected to form a ring or may not be connected.

2. The organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 1, characterized in that: The structural formula is as follows: 。 3. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to any one of claims 1 to 2, characterized in that: The preparation method of the compound represented by formula (I) comprises the following steps: (1) Compound 1 and compound 2 undergo carbon-carbon coupling reaction to obtain compound 3; (2) Compound 3 and compound 4 undergo nucleophilic substitution reaction to construct an eight-membered ring to obtain compound 5; (3) Compound 5 is subjected to a nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain a compound represented by formula (I); The preparation method of the compound represented by formula (II) comprises the following steps: (4) subjecting the secondary amine site of the compound represented by formula (I) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (II); The preparation method of the compound represented by formula (III) comprises the following steps: (5) The secondary amine site of compound 7 undergoes nucleophilic substitution reaction with compound 8 to obtain compound 9; (6) Compound 9 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (III); The preparation method of the compound represented by formula (IV) comprises the following steps: (7) The secondary amine site of compound 10 undergoes a nucleophilic substitution reaction with compound 11 to obtain compound 12; (8) Compound 12 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (IV); The preparation method of the compound represented by formula (V) comprises the following steps: (9) Compound 13 and compound 14 undergo carbon-carbon coupling reaction to obtain compound 15; (10) Compound 15 and compound 16 undergo nucleophilic substitution reaction to construct an eight-membered ring to obtain compound 17; (11) Compound 17 was subjected to nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain compound 18; (12) Compound 18 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (V); The preparation method of the compound represented by formula (VI) comprises the following steps: (13) The secondary amine site of compound 19 undergoes nucleophilic substitution reaction with compound 20 to obtain compound 21; (14) Compound 21 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (VI); ； The preparation method of the compound represented by formula (VII) comprises the following steps: (15) Compound 22 and compound 23 were reacted by carbon-carbon coupling reaction to obtain compound 24; (16) Compound 24 reacts with compound 25 via nucleophilic substitution to give compound 26; (17) Compound 26 was subjected to nitro ring-bonding reaction under the catalysis of triphenylphosphine to obtain compound 27; (18) Compound 27 is subjected to a cyclization reaction with a boron source, chlorosilanes, ammonia, ethers, sulfur or selenium, or directly forms a CC bond through a Scholl oxidation coupling reaction to obtain a compound represented by formula (VII); The preparation method of the compound represented by formula (VIII) comprises the following steps: (19) subjecting the secondary amine site of the compound represented by formula (VII) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (VIII); The preparation method of the compound represented by formula (IX) comprises the following steps: (20) subjecting the secondary amine site of the compound represented by formula (V) to a Buchwald-Hartwig coupling reaction with compound 6 to obtain a compound represented by formula (IX); 。 4. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the carbon-carbon coupling reaction in step (1) is 100-110° C. and the time is 8-12 h; The temperature of the nucleophilic substitution reaction in step (2) is 140-150° C. and the time is 4-8 hours; The temperature of the nitro ring-bonding reaction in step (3) is 150-180°C and the time is 4-8 hours; The temperature of the Buchwald-Hartwig coupling reaction in step (4) is 120-140° C. and the time is 4-8 hours.

5. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the nucleophilic substitution reaction in step (5) is 140-150° C. and the time is 4-8 hours; The temperature of the cyclization reaction in step (6) is -40 to 210°C and the time is 24 to 48 hours; The temperature of the nucleophilic substitution reaction in step (7) is 140-150° C. and the time is 4-8 hours; The temperature of the cyclization reaction in step (8) is -40 to 210°C and the time is 24 to 48 hours.

6. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the carbon-carbon coupling reaction in step (9) is 100-110° C. and the time is 8-12 h; The temperature of the nucleophilic substitution reaction in step (10) is 140-150° C. and the time is 4-8 hours; The temperature of the nitro ring-bonding reaction in step (11) is 150-180° C. and the time is 4-8 hours; The temperature of the cyclization reaction in step (12) is -40 to 210°C and the time is 24 to 48 hours.

7. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the nucleophilic substitution reaction in step (13) is 140-150° C. and the time is 4-8 hours; The temperature of the cyclization reaction in step (14) is -40 to 210°C and the time is 24 to 48 hours.

8. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the carbon-carbon coupling reaction in step (15) is 100-110° C. and the time is 8-12 h; The temperature of the nucleophilic substitution reaction in step (16) is 140-150° C. and the time is 4-8 hours; The temperature of the nitro ring-bonding reaction in step (17) is 150-180° C. and the time is 4-8 hours; The temperature of the cyclization reaction in step (18) is -40 to 210°C and the time is 24 to 48 hours.

9. The method for preparing an organic semiconductor material containing an eight-membered nitrogen-fused ring according to claim 3, characterized in that: The temperature of the Buchwald-Hartwig coupling reaction in step (19) is 120-140° C. and the time is 4-8 h; The temperature of the Buchwald-Hartwig coupling reaction in step (20) is 120-140° C. and the time is 4-8 hours.

10. Use of the organic semiconductor material containing an eight-membered nitrogen-fused ring according to any one of claims 1 to 2 in the preparation of an organic electroluminescent device.

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