A compound, preparation method and application thereof

Abstract

The present invention provides a compound, a preparation method thereof, and an application thereof. The structural formula of the compound is shown in Formula I, and most of them are triazine structures, which are functional groups with strong electron-withdrawing ability and can effectively improve the electron mobility of electron transport materials. The compound can be used to prepare organic electroluminescent devices, improve the problem of electron-hole imbalance inside organic electroluminescent devices, improve the luminous efficiency and the electron mobility of electron transport materials, and the planar molecular structure can prevent the π-conjugated system of the core structure from being continued, ensuring a high triplet energy level (ET) and a wide band gap, thereby further improving the luminous efficiency, improving the degree of energy level matching of each layer of the device, reducing the driving voltage, and extending the device life.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, and in particular to a compound, a preparation method and application thereof. Background Art

[0002] With the rapid development of information technology, new performance goals and requirements for information display systems have emerged. Displays with high brightness, high resolution, wide viewing angles, and low energy consumption have become a research hotspot. Organic electroluminescent (OLED) display technology can meet these needs while also offering a wide operating temperature range and flexible display capabilities. Therefore, following cathode ray tube (CRT) displays, liquid crystal displays (LCD), and plasma flat panel displays (PDP), OLED has become the new favorite of the new generation of flat panel displays. It is also hailed as a flat-panel display technology with fantastic display features.

[0003] In order to improve the efficiency and stability of organic electroluminescent elements, the organic material layer generally includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron transport layer (ETL) and an electron injection layer (EIL). In the above-mentioned organic light-emitting element, when a voltage is applied between the anode and the cathode, holes from the anode and electrons from the cathode are injected into the organic material layer, and the generated excitons generate light with a specific wavelength when they migrate to the ground state. Among them, the electron transport layer is a key component in the organic electroluminescent element. The structure of the electron transport material used generally contains nitrogen-containing heterocycles such as pyridine, pyrimidine, oxadiazole, triazole, imidazole and electron-withdrawing groups such as phosphorus oxide with electron transport properties. Its electron mobility, energy band structure and the local electric field, carrier and Joule heat distribution near it will directly affect the aging rate of organic materials and devices, thereby affecting the life of the device.

[0004] In order to meet the needs of market applications, the luminous efficiency, driving voltage and life of organic electroluminescent elements need to be improved. Summary of the Invention

[0005] In view of this, the object of the present invention is to provide a compound, a preparation method and application thereof. The electron transport material has high electron mobility, can reduce driving voltage, extend device life, and improve luminous efficiency.

[0006] In order to achieve the above purpose, the present invention adopts the following technical solutions:

[0007] In a first aspect, the present invention provides a compound, the structural formula of which is shown in Formula I below:

[0008]

[0009] wherein R1, R2 or R3 are each independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphate, phosphoryl, silicon, borane, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C2~C 30 Alkynyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 20 heteroaryl, substituted or unsubstituted C3-C25 heteroarylamine, substituted or unsubstituted C6-C 60 Arylamine, substituted or unsubstituted C1~C 30 Alkoxy or substituted or unsubstituted C6~C 60 aryloxy;

[0010] The heteroatoms in the heterocycloalkyl, heteroaryl or heteroarylamine group are selected from any one or more of O, N or S;

[0011] X and Y are each independently preferably selected from C-R4R5, -N-R6, -O- or -S-;

[0012] R4 and R5 are each independently preferably selected from H, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl;

[0013] R6 is preferably selected from substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl;

[0014] The heteroatoms in the heteroaryl group are selected from any one or more of O, N or S;

[0015] or

[0016] X and R2 or X and R1 or Y and R3 or Y and ring B form a C3~C 30 a substituted or unsubstituted ring or heterocycle;

[0017] The heteroatom of the heterocyclic ring is selected from any one or more of O, N or S;

[0018] m and n are each independently selected from 0 or 1, and m and n are not 0 at the same time;

[0019] L1 and L2 are each independently preferably selected from a connecting bond, a substituted or unsubstituted C6 to C 30 arylene or substituted or unsubstituted C3~C 20 Heteroarylene;

[0020] The heteroatoms in the heteroarylene group are selected from any one or more of O, N or S;

[0021] Ring B is preferably selected from substituted or unsubstituted C3 to C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 20 Heteroaryl, substituted or unsubstituted C3~C 25 Heteroarylamine or substituted or unsubstituted C6~C 60 arylamine groups;

[0022] The heteroatoms in the heterocycloalkyl, heteroaryl or heteroarylamine group are selected from any one or more of O, N or S;

[0023] Ar1, Ar2, Ar3 or Ar4 are each independently preferably selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 20 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or substituted or unsubstituted C6~C 60 arylamine groups;

[0024] The heteroatoms in the heterocycloalkyl group, heteroaryl group or heteroarylamine group are selected from any one or more of O, N or S.

[0025] In the present invention, the R1, R2 or R3 are each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C3~C 10 Heterocycloalkyl, substituted or unsubstituted C6~C 20 aryl, substituted or unsubstituted C3~C 10 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or substituted or unsubstituted C6~C20 arylamine groups;

[0026] The heteroatoms in the heterocycloalkyl group, heteroaryl group or heteroarylamine group are selected from any one or more of O, N or S.

[0027] In the present invention, the L1 and L2 are each independently more preferably selected from a connecting bond, a substituted or unsubstituted C6 to C 20 arylene or substituted or unsubstituted C3~C 18 Heteroarylene;

[0028] The heteroatom in the heteroarylene group is selected from any one or more of O, N or S.

[0029] Ring B is more preferably selected from substituted or unsubstituted C6 to C 30 aryl or substituted or unsubstituted C3~C 20 heteroaryl;

[0030] The heteroatoms in the heteroaryl group are selected from any one or more of O, N or S.

[0031] In the present invention, Ar1, Ar2, Ar3 or Ar4 are each independently more preferably selected from substituted or unsubstituted C6 to C 20 aryl, substituted or unsubstituted C3~C 15 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or unsubstituted C6~C 30 arylamine groups;

[0032] The heteroatom in the heteroaryl group or heteroarylamine group is selected from any one or more of O, N or S.

[0033] In the present invention, the compound is further preferably selected from any one of the following formulas (ET-1) to (ET-100):

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] In a second aspect, the present invention provides a method for preparing the compound, comprising the following steps:

[0040] (1) The raw material A shown in Formula 1 and the raw material Q shown in Formula 2 undergo a catalytic reaction to obtain the intermediate 1 shown in Formula 3;

[0041] (2) Intermediate 1 undergoes a cyclization reaction to obtain intermediate 2 shown in formula 4;

[0042] (3) intermediate 2 reacts with the raw material M shown in formula 5 or formula 6 to obtain intermediate 3 shown in formula 7 or formula 8, respectively;

[0043] (4) intermediate 3 reacts with the raw material E represented by formula 9 or formula 10 to obtain the target compound;

[0044]

[0045] In the present invention, the catalyst for the catalytic reaction in step (1) preferably includes tetrakis(triphenylphosphine palladium) and potassium carbonate, the solvent for the catalytic reaction in step (1) preferably includes toluene, ethanol and water, and more preferably includes a mixed solution of toluene:ethanol:water = 2:1:1 (volume ratio), the temperature of the catalytic reaction in step (1) is preferably 80-100°C, more preferably 85-95°C, and the time is preferably 10-12h, more preferably 10-11h.

[0046] In the present invention, the catalyst for the catalytic reaction in step (2) preferably includes potassium carbonate, the solvent for the catalytic reaction in step (2) preferably includes dimethyl sulfoxide, the temperature for the catalytic reaction in step (1) is preferably 150 to 180° C., more preferably 160 to 170° C., and the time is preferably 20 to 28 hours, more preferably 24 to 28 hours.

[0047] It should be noted that in the present invention, when intermediate 2 is catalytically reacted with the raw material M shown in Formula 5 (L2 represents a non-connecting bond) to obtain intermediate 3 shown in Formula 7, the catalyst for the catalytic reaction preferably includes palladium acetate, cesium carbonate and 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl, the solvent for the catalytic reaction preferably includes ethylene glycol dimethyl ether and water, more preferably includes a mixed solution of ethylene glycol dimethyl ether: water = 2: 1 (volume ratio), and the time for the catalytic reaction is preferably 4 to 8 hours. In the present invention, when intermediate 2 is catalytically reacted with the raw material M shown in Formula 6 (L2 represents a connecting bond) to obtain intermediate 3 shown in Formula 8, the catalyst for the catalytic reaction preferably includes tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine and sodium tert-butoxide, the solvent for the catalytic reaction preferably includes toluene, and the time for the catalytic reaction is preferably 4 to 8 hours.

[0048] In the present invention, when intermediate 3 is catalytically reacted with raw material E (L1 represents a non-connecting bond) shown in formula 9 to obtain the target compound, the catalyst of the catalytic reaction preferably includes palladium acetate, cesium carbonate and 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl, the solvent of the catalytic reaction preferably includes ethylene glycol dimethyl ether and water, more preferably includes a mixed solution of ethylene glycol dimethyl ether: water = 2: 1 (volume ratio), and the time of the catalytic reaction is preferably 4 to 8 hours. In the present invention, when intermediate 3 is catalytically reacted with raw material E (L1 represents a connecting bond) shown in formula 10 to obtain the target compound, the catalyst of the catalytic reaction preferably includes tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine and sodium tert-butoxide, the solvent of the catalytic reaction preferably includes toluene, and the time of the catalytic reaction is preferably 4 to 8 hours.

[0049] In a third aspect, the present invention provides use of the compound or the compound prepared according to the preparation method in the preparation of an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.

[0050] In a fourth aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode;

[0051] The organic layer comprises the compound according to claim 1 or the compound prepared according to the preparation method.

[0052] Preferably, the organic layer includes any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer or a capping layer.

[0053] Preferably, the electron transport layer includes any one or more of an electron buffer layer, a hole blocking layer, an electron transport base layer or an electron injection base layer.

[0054] Compared with the prior art, the present invention has the following beneficial effects:

[0055] The compounds provided by the present invention are mostly triazine structures, which are functional groups with strong electron-withdrawing ability and can effectively improve the electron mobility of electron transport materials. These compounds can be used to prepare organic electroluminescent devices, improve the problem of electron-hole imbalance within organic electroluminescent devices, and improve the luminous efficiency and the electron mobility of electron transport materials. The planar molecular structure can prevent the continuation of the π-conjugated system of the core structure, ensuring a high triplet energy level (ET) and a wide band gap, thereby further improving the luminous efficiency, improving the degree of energy level matching between device layers, reducing the driving voltage, and extending the device life. DETAILED DESCRIPTION

[0056] The following will clearly and completely describe the technical solutions of the present invention in conjunction with the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0057] The present invention provides a compound, the structural formula of which is shown in the following formula I:

[0058]

[0059] wherein R1, R2 or R3 are each independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphate, phosphoryl, silicon, borane, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C2~C 30

[0060] Preferably, the organic layer includes any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer or a capping layer.

[0061] Preferably, the electron transport layer includes any one or more of an electron buffer layer, a hole blocking layer, an electron transport base layer or an electron injection base layer.

[0062] Compared with the prior art, the present invention has the following beneficial effects:

[0063] The compounds provided by the present invention are mostly triazine structures, which are functional groups with strong electron-withdrawing ability and can effectively improve the electron mobility of electron transport materials. These compounds can be used to prepare organic electroluminescent devices, improve the problem of electron-hole imbalance within organic electroluminescent devices, and improve the luminous efficiency and the electron mobility of electron transport materials. The planar molecular structure can prevent the continuation of the π-conjugated system of the core structure, ensuring a high triplet energy level (ET) and a wide band gap, thereby further improving the luminous efficiency, improving the degree of energy level matching between device layers, reducing the driving voltage, and extending the device life. DETAILED DESCRIPTION

[0065] The following will clearly and completely describe the technical solutions of the present invention in conjunction with the embodiments of the present invention. Obviously, the embodiments described are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.

[0066] The present invention provides a compound, the structural formula of which is shown in the following formula I:

[0067]

[0068] wherein R1, R2 or R3 are each independently selected from hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, amino, sulfonic acid, sulfonyl, phosphate, phosphoryl, silicon, borane, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C2~C 30 Alkenyl, substituted or unsubstituted C2~C 30 Alkynyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 20 Heteroaryl, substituted or unsubstituted C3~C 25 Heteroarylamine, substituted or unsubstituted C6~C 60 Arylamine, substituted or unsubstituted C1~C 30 Alkoxy or substituted or unsubstituted C6~C 60 aryloxy;

[0069] The heteroatoms in the heterocycloalkyl, heteroaryl or heteroarylamine group are selected from any one or more of O, N or S;

[0070] X and Y are each independently preferably selected from C-R4R5, -N-R6, -O- or -S-;

[0071] R4 and R5 are each independently preferably selected from H, substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl;

[0072] R6 is preferably selected from substituted or unsubstituted C1-C 30 Alkyl, substituted or unsubstituted C6~C 30 aryl or substituted or unsubstituted C3~C 30 heteroaryl;

[0073] The heteroatoms in the heteroaryl group are selected from any one or more of O, N or S;

[0074] or

[0075] X and R2 or X and R1 or Y and R3 or Y and ring B form a C3~C 30a substituted or unsubstituted ring or heterocycle;

[0076] The heteroatom of the heterocyclic ring is selected from any one or more of O, N or S;

[0077] m and n are each independently preferably selected from 0 or 1, and m and n are not 0 at the same time;

[0078] L1 and L2 are each independently preferably selected from a connecting bond, a substituted or unsubstituted C6 to C 30 arylene or substituted or unsubstituted C3~C 20 Heteroarylene;

[0079] The heteroatoms in the heteroarylene group are selected from any one or more of O, N or S;

[0080] Ring B is preferably selected from substituted or unsubstituted C3 to C 30 Cycloalkyl, substituted or unsubstituted C3~C 30 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 20 heteroaryl, substituted or unsubstituted C3-C25 heteroarylamine or substituted or unsubstituted C6-C 60 arylamine groups;

[0081] The heteroatoms in the heterocycloalkyl, heteroaryl or heteroarylamine group are selected from any one or more of O, N or S;

[0082] Ar1, Ar2, Ar3 or Ar4 are each independently preferably selected from substituted or unsubstituted C1 to C 30 Alkyl, substituted or unsubstituted C3~C 30 Cycloalkyl, substituted or unsubstituted C3~C 20 Heterocycloalkyl, substituted or unsubstituted C6~C 30 aryl, substituted or unsubstituted C3~C 30 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or substituted or unsubstituted C6~C 60 arylamine groups;

[0083] The heteroatoms in the heterocycloalkyl group, heteroaryl group or heteroarylamine group are selected from any one or more of O, N or S.

[0084] In the present invention, the R1, R2 or R3 are further independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C3~C 10Heterocycloalkyl, substituted or unsubstituted C6~C 20 aryl, substituted or unsubstituted C3~C 10 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or substituted or unsubstituted C6~C 20 arylamine groups;

[0085] The heteroatoms in the heterocycloalkyl group, heteroaryl group or heteroarylamine group are selected from any one or more of O, N or S.

[0086] In the present invention, L1 and L2 are further independently selected from connecting bonds, substituted or unsubstituted C6 to C 20 arylene or substituted or unsubstituted C3~C 18 Heteroarylene;

[0087] The heteroatom in the heteroarylene group is selected from any one or more of O, N or S.

[0088] Ring B is further independently preferably selected from substituted or unsubstituted C6 to C 30 aryl or substituted or unsubstituted C3~C 20 heteroaryl;

[0089] In the present invention, the heteroatom in the heteroaryl group is selected from any one or more of O, N or S.

[0090] In the present invention, Ar1, Ar2, Ar3 or Ar4 are further independently preferably selected from substituted or unsubstituted C6 to C 20 aryl, substituted or unsubstituted C3~C 15 Heteroaryl, substituted or unsubstituted C3~C 15 Heteroarylamine or unsubstituted C6~C 30 arylamine groups;

[0091] The heteroatom in the heteroaryl group or heteroarylamine group is selected from any one or more of O, N or S.

[0092] In the present invention, the structural formula of the compound is more preferably any one of formulas (ET-1) to (ET-100). The specific chemical formula is as described in the above invention content and will not be repeated here.

[0093] The present invention also provides a method for preparing the compound, comprising the following steps:

[0094] (1) The raw material A shown in Formula 1 and the raw material Q shown in Formula 2 undergo a catalytic reaction to obtain the intermediate 1 shown in Formula 3;

[0095] (2) Intermediate 1 undergoes a cyclization reaction to obtain intermediate 2 shown in formula 4;

[0096] (3) intermediate 2 reacts with the raw material M shown in formula 5 or formula 6 to obtain intermediate 3 shown in formula 7 or formula 8, respectively;

[0097] (4) intermediate 3 reacts with the raw material E represented by formula 9 or formula 10 to obtain the target compound;

[0098]

[0099] In the present invention, the catalyst for the catalytic reaction in step (1) preferably includes tetrakis(triphenylphosphine palladium) and potassium carbonate, the solvent for the catalytic reaction in step (1) preferably includes toluene, ethanol and water, and more preferably includes a mixed solution of toluene:ethanol:water = 2:1:1 (volume ratio), the temperature of the catalytic reaction in step (1) is preferably 80-100°C, more preferably 85-95°C, and the time is preferably 10-12h, more preferably 10-11h.

[0100] In the present invention, the catalyst for the catalytic reaction in step (2) preferably includes potassium carbonate, the solvent for the catalytic reaction in step (2) preferably includes dimethyl sulfoxide, the temperature for the catalytic reaction in step (1) is preferably 150 to 180° C., more preferably 160 to 170° C., and the time is preferably 20 to 28 hours, more preferably 24 to 28 hours.

[0101] It should be noted that in the present invention, when intermediate 2 is catalytically reacted with the raw material M shown in Formula 5 (L2 represents a non-connecting bond) to obtain intermediate 3 shown in Formula 7, the catalyst for the catalytic reaction preferably includes palladium acetate, cesium carbonate and 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl, the solvent for the catalytic reaction preferably includes ethylene glycol dimethyl ether and water, more preferably includes a mixed solution of ethylene glycol dimethyl ether: water = 2: 1 (volume ratio), and the time for the catalytic reaction is preferably 4 to 8 hours. In the present invention, when intermediate 2 is catalytically reacted with the raw material M shown in Formula 6 (L2 represents a connecting bond) to obtain intermediate 3 shown in Formula 8, the catalyst for the catalytic reaction preferably includes tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine and sodium tert-butoxide, the solvent for the catalytic reaction preferably includes toluene, and the time for the catalytic reaction is preferably 4 to 8 hours.

[0102] In the present invention, when intermediate 3 is catalytically reacted with raw material E (L1 represents a non-connecting bond) shown in formula 9 to obtain the target compound, the catalyst of the catalytic reaction preferably includes palladium acetate, cesium carbonate and 2-dicyclohexylphosphine-2', 4', 6'-triisopropylbiphenyl, the solvent of the catalytic reaction preferably includes ethylene glycol dimethyl ether and water, more preferably includes a mixed solution of ethylene glycol dimethyl ether: water = 2: 1 (volume ratio), and the time of the catalytic reaction is preferably 4 to 8 hours. In the present invention, when intermediate 3 is catalytically reacted with raw material E (L1 represents a connecting bond) shown in formula 10 to obtain the target compound, the catalyst of the catalytic reaction preferably includes tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine and sodium tert-butoxide, the solvent of the catalytic reaction preferably includes toluene, and the time of the catalytic reaction is preferably 4 to 8 hours.

[0103] More specifically, in the present invention, when L1 and L2 represent non-connecting bonds, the preparation method of the compound is preferably as follows:

[0104] (1) Under nitrogen protection, raw material A (1.1 eq) and raw material Q (1.0 eq) were added to a three-necked reaction flask, and tetrakis(triphenylphosphine palladium) (0.01 eq) and potassium carbonate (2.0 eq) were added respectively. Then, a mixed solution of toluene, ethanol and water (toluene: ethanol: water = 2:1:1 by volume) was added, and the temperature was raised to 90°C and refluxed overnight. After the reaction was completed, the reaction solution was cooled to 40-50°C, the water layer was separated, and the organic layer was dried with anhydrous sodium sulfate. The organic layer was spin-dried to obtain a solid organic matter, and a small amount of dichloromethane was used to completely dissolve the solid organic matter. Then, the solid organic matter was slowly added dropwise to a petroleum ether solution and stirred evenly. A precipitate was precipitated, and the solid was filtered off, washed with anhydrous ethanol and petroleum ether in sequence, and dried to obtain intermediate 1;

[0105] (2) Under nitrogen protection, intermediate 1 (1.0 eq) was added to a reaction flask, followed by potassium carbonate (1.1 eq) and dimethyl sulfoxide (DMSO) as solvent, and the temperature was raised to 160°C for 24 h. The reaction solution was cooled to room temperature, water was added and stirred, and then ethyl acetate was added to extract the reaction solution. The obtained extract was washed once with water, dried over anhydrous magnesium sulfate, and dried to obtain an oil. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain intermediate 2;

[0106] (3) Under nitrogen protection, intermediate 2 (1.0 eq) and raw material M (1.1 eq) were added to a reaction flask, and then Pd(oAc)2 (0.05 eq), cesium carbonate (2.0 eq), and ligand X-PHOS (0.11 eq) were added respectively, and a mixed solution of ethylene glycol dimethyl ether: water = 2:1 by volume was added, and the temperature was raised and refluxed for 16 hours. After the reaction was completed, the reaction solution was cooled to 40-50°C, the water layer was separated, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was spin-dried to obtain a black substance. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume), and the product was collected to obtain intermediate 3;

[0107] (4) Under nitrogen protection, intermediate 3 (1.0 eq) and raw material E (1.1 eq) were added to a reaction flask, and then Pd(oAc)2 (0.05 eq), cesium carbonate (2.0 eq), and ligand X-PHOS (0.11 eq) were added respectively, and a mixed solution of ethylene glycol dimethyl ether: water = 2:1 by volume was added, and the temperature was raised and refluxed for 16 hours. After the reaction was completed, the reaction solution was cooled to 40-50°C, the water layer was separated, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was spin-dried to obtain a black substance. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain the target compound;

[0108] The specific synthesis route is shown in the following reaction formula (the specific interpretations of ring B, X, Y, R1 to R3, L1, L2 and Ar1 to Ar4 in the formula are as described above):

[0109]

[0110] In the present invention, when L1 and L2 represent a connecting bond, the preparation method of the compound is preferably as follows:

[0111] (1) Under nitrogen protection, raw material A (1.1 eq) and raw material Q (1.0 eq) were added to a three-necked reaction flask, and tetrakis(triphenylphosphine palladium) (0.01 eq) and potassium carbonate (2.0 eq) were added respectively. Then, a mixed solution of toluene, ethanol and water (toluene: ethanol: water = 2:1:1 by volume) was added, and the temperature was raised to 90°C and refluxed overnight. After the reaction was completed, the reaction solution was cooled to 40-50°C, the water layer was separated, and the organic layer was dried with anhydrous sodium sulfate. The organic layer was spin-dried to obtain a solid organic matter, and a small amount of dichloromethane was used to completely dissolve the solid organic matter. Then, the solid organic matter was slowly added dropwise to a petroleum ether solution and stirred evenly. A precipitate was precipitated, and the solid was filtered off, washed with anhydrous ethanol and petroleum ether in sequence, and dried to obtain intermediate 1;

[0112] (2) Under nitrogen protection, intermediate 1 (1.0 eq) was added to a reaction flask, followed by potassium carbonate (1.1 eq) and dimethyl sulfoxide (DMSO) as solvent, and the temperature was raised to 160°C for 24 h. The reaction solution was cooled to room temperature, water was added and stirred, and then ethyl acetate was added to extract the reaction solution. The obtained extract was washed once with water, dried over anhydrous magnesium sulfate, and dried to obtain an oil. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain intermediate 2;

[0113] (3) Under nitrogen protection, intermediate 2 (1.0 eq) and raw material M (1.1 eq) were added to a reaction flask, and tris(dibenzylideneacetone)dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq) and sodium tert-butoxide (2.0 eq) were added respectively, stirred evenly, heated to reflux, and reacted for 5 h; after the reaction was completed, the temperature was slightly lowered, and diatomaceous earth was used for filtration to remove salt and catalyst. After the filtrate was cooled to room temperature, it was washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator; a small amount of dichloromethane was used to completely dissolve the solid organic matter, and then it was slowly added dropwise to the petroleum ether solution, stirred evenly, and a precipitate was precipitated. The solid was filtered and washed with anhydrous ethanol and petroleum ether in turn, and dried to obtain intermediate 3;

[0114] (4) Under nitrogen protection, the intermediate 3 (1.0 eq) and the raw material E (1.1 eq) were dissolved in a toluene solution, tris(dibenzylideneacetone)dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq) and sodium tert-butoxide (2.0 eq) were added, stirred evenly, heated to reflux, and reacted for 5 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered using diatomaceous earth to remove salt and catalyst. The filtrate was cooled to room temperature and washed three times with water. The organic phase was retained, and the aqueous phase was then extracted with ethyl acetate. After the organic phases were combined, they were dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain the target compound.

[0115] The specific synthesis route is shown in the following reaction formula (wherein ring B, X, Y, R1 to R3 and Ar l ~Ar4 (specific meaning as described above);

[0116]

[0117] More specifically, in the present invention, when X is O or S in the chemical formula of raw material A, raw material A is preferably prepared by the following preparation method:

[0118] (1) Under nitrogen protection, a (1 eq) was added to a three-necked flask, followed by Pd(pph3)4 (0.1 eq), CuI (2 eq), Et3N (2 eq), and 200 mL of DMF. Finally, b (2 eq) was added and the temperature was raised to 80°C for 48 h. After cooling to room temperature, the insoluble matter was removed and the reaction solution was poured into 1000 mL of water. A solid precipitated, which was filtered and dried. Pure product c was isolated by silica gel column using a mixture of petroleum ether and ethyl acetate (volume ratio, petroleum ether:ethyl acetate = 10:1).

[0119] (2) Dissolve c (1 eq) in 200 mL of dichloromethane and gradually add NBS (1.1 eq) at room temperature for approximately 10 min. The reaction is continued for 16 h. The insoluble matter is removed by filtration, and the filtrate is dried to obtain a solid. Add 200 mL of petroleum ether, 50 mL of methanol, and 100 mL of water, stir for 24 h, and filter to obtain a solid d.

[0120] (3) Under nitrogen protection, d (1 eq) was added to a reaction flask, and PdCl2(dppf) (0.03 eq), potassium acetate (2 eq) and 1,4-dioxane 200 mL were added respectively. The temperature was raised to 90°C and the reaction was carried out for 6 h. The mixture was cooled to room temperature, filtered to remove insoluble matter, and the filtrate was dried to obtain a black oil. A mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:4 by volume) was separated on a silica gel column to obtain the target product, raw material A;

[0121] The specific synthesis route is shown in the following reaction formula (the specific interpretations of R1 and R2 in the formula are as described above):

[0122]

[0123] More specifically, in the present invention, when X is C in the chemical formula of raw material A, raw material A is preferably prepared by the following preparation method:

[0124] (1) Dissolve A1 (1 eq) in 100 mL of dichloromethane for later use. Then add TiCl4 (6 eq) to 80 mL of dichloromethane and stir. Cool to -50°C under nitrogen and keep for 30 min. Inject dimethylzinc (6 eq). The solution changes from colorless to orange-brown and stir at -50°C for 1 h. Add the dichloromethane solution of a1 dropwise and react at -50°C for 2 h. Warm to -10°C and add cold saturated ammonium chloride solution and stir for 30 min. Let stand and separate. Wash the organic layer with brine, dry over anhydrous sodium sulfate, and concentrate to obtain an oil. Purify by column with a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:10 by volume) to obtain a colorless oil B1.

[0125] (2) Dissolve B1 (1 eq) in 200 mL of anhydrous ethanol, add DDQ (1.1 eq) and 3 g of palladium-carbon catalyst, and heat and reflux for 4 h. Cool, filter, remove the catalyst, and concentrate to obtain product C1.

[0126] (3) Compound C1 (1 eq) was dissolved in 100 mL of dichloromethane, and NBS (1 eq) was added portionwise. The mixture was allowed to react at room temperature for 24 h. Insoluble matter was removed by filtration, and the mixture was concentrated and methanol was added to precipitate a solid. The filter cake was then rinsed with water and methanol and dried to obtain compound D1.

[0127] (4) Compound D1 (1 eq) and raw material E1 (1.1 eq) were added to a reaction flask, followed by tetrakistriphenylphosphine palladium (0.01 eq) and potassium carbonate (2 eq). 400 mL of a mixture of toluene, ethanol, and water (toluene:ethanol:water = 2:1:1 by volume) was added, and the temperature was raised to 90°C for 16 h. The mixture was cooled, separated, and the toluene layer was washed once with water, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance. The oily substance was then passed through a silica gel column and eluted with a mixture of dichloromethane and petroleum ether (dichloromethane:petroleum ether = 1:4 by volume) to obtain a white solid F1.

[0128] (5) Dissolve 0.077 mol of compound F1 in 100 mL of DMF, add 0.093 mol of NBS in portions, and heat to 100°C for 24 h. Pour the reaction solution into 300 mL of cold water and stir until a large amount of solid precipitates. Filter to obtain a dark product, which is then passed through a silica gel column and washed with a mixture of dichloromethane and petroleum ether (1:4 by volume) to obtain a white solid, G1.

[0129] (6) Add G1 (1 eq) to a reaction flask, add PdCl2 (dppf, 0.03 eq), potassium acetate (2 eq) and 1,4-dioxane 200 mL respectively, and heat to 90°C under nitrogen for 6 h. Cool to room temperature, filter, remove insoluble matter, and spin-dry the filtrate to obtain a black oil. Use a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:4 by volume) to pass through a silica gel column to separate the target product, raw material A;

[0130] The specific synthesis route is as follows (the specific definitions of R1 and R2 in the formula are as described above):

[0131]

[0132] More specifically, in the present invention, when X is N in the chemical formula of raw material A, raw material A is preferably prepared by the following preparation method:

[0133] (1) Dissolve A2 (1 eq) in 200 mL of dichloromethane and gradually add NBS (1 eq) at room temperature for approximately 10 min. The reaction is continued for 16 h. Filter to remove insoluble matter, spin dry the filtrate to obtain a solid, add 300 mL of petroleum ether, 50 mL of methanol, and 100 mL of water, stir for 24 h, and filter to obtain solid B2.

[0134] (2) B2 (1 eq), raw material M2 (1.1 eq), Pd(pph3)4 (0.01 eq), and potassium carbonate (2 eq) were added to a reaction flask in sequence. Under nitrogen protection, 400 mL of a mixed solution of toluene, ethanol, and water (toluene: ethanol: water = 2:1:1 by volume) was added, and the temperature was raised to 90°C for 18 h. Post-processing process: Cooling and separation, drying over anhydrous magnesium sulfate, and the toluene layer was spin-dried to obtain a black oily substance, which was passed through a silica gel column and eluted with a mixture of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:2 by volume) to collect the target product D2;

[0135] (3) Dried D2 (1 eq) was added to 100 mL of DMF and a few drops of acetic acid were added. NBS (1.1 eq) was then added in portions and the temperature was raised to 100°C for overnight reaction. After the reaction was complete, the temperature was lowered and the reaction solution was poured into 500 mL of water. A large amount of solid precipitated, which was filtered and dried to obtain E2.

[0136] (4) E2 (1 eq) was added to a reaction flask, and PdCl2 (dppf, 0.03 eq), potassium acetate (2 eq) and 1,4-dioxane 200 mL were added respectively. The temperature was raised to 90°C under nitrogen protection and the reaction was carried out for 6 h. Post-treatment process: Cool to room temperature, filter, remove insoluble matter, and spin-dry the filtrate to obtain a black oil. Pass through a silica gel column and separate using a mixture of dichloromethane and petroleum ether (by volume ratio, dichloromethane: petroleum ether = 1:4) to obtain the target product, raw material A;

[0137] The specific synthesis route is as follows (the specific definitions of R1 and R2 in the formula are as described above):

[0138]

[0139] The present invention also provides a use of the compound or the compound prepared according to the preparation method in preparing an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.

[0140] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode.

[0141] The organic layer includes any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer or a capping layer.

[0142] The electron transport layer includes any one or more of an electron buffer layer, a hole blocking layer, an electron transport base layer or an electron injection base layer.

[0143] The present invention has no particular limitation on the preparation method of the organic electroluminescent device. Preferably, a metal, a conductive oxide, or an alloy thereof is evaporated on a substrate to form an anode by thin film evaporation, electron beam evaporation, or physical vapor deposition, and then an organic layer and a evaporated cathode are formed thereon to obtain the organic electroluminescent device.

[0144] To further illustrate the present invention, the following examples are provided for detailed description. The sources of the experimental raw materials used in the following examples of the present invention are not particularly limited and can be purchased from the market or prepared according to conventional preparation methods well known to those skilled in the art.

[0145] Preparation Example 1

[0146] This preparation example provides a raw material A, and the synthesis route is as follows:

[0147]

[0148] The specific steps are as follows:

[0149] (1) Dissolve the raw material A1 (100 mmol) in 100 mL of dichloromethane for later use. Then, under nitrogen protection, add TiCl4 (600 mmol) to 80 mL of dichloromethane and stir. After cooling to -50°C and maintaining for 30 minutes, add dimethylzinc (600 mmol), and the solution changes from colorless to orange-brown. Stir at -50°C for 1 hour. Then add the dichloromethane solution of A1 dropwise and react at -50°C for 2 hours. Then heat to -10°C and add cold saturated ammonium chloride solution and stir for 30 minutes. Let stand and separate. Wash the organic layer with brine, dry over anhydrous sodium sulfate, and concentrate to obtain an oil. Use a mixed solution of dichloromethane and petroleum ether (by volume ratio, dichloromethane: petroleum ether = 1:10) to purify the remaining substance by column chromatography to obtain A2 (19.49 g, yield: 98.1%, MW: 198.69);

[0150] (2) Compound A2 (95 mmol) was dissolved in 200 mL of anhydrous ethanol, and DDQ (105 mmol) and palladium-carbon catalyst (3 g) were added, respectively. The mixture was heated and refluxed for 4 h. The reaction was then cooled, filtered, and the catalyst removed. The mixture was concentrated to afford product A3 (17.7 g, yield: 94.9%, MW: 196.65).

[0151] (3) Compound A3 (90 mmol) was dissolved in 100 mL of dichloromethane, and NBS (90 mmol) was added portionwise. The mixture was allowed to react at room temperature for 24 h. Insoluble matter was removed by filtration, and the mixture was concentrated and methanol was added to precipitate a solid. The filter cake was then rinsed with water and methanol and dried to obtain compound A4 (23.6 g, yield: 95.0%, MW: 275.50).

[0152] (4) Compound A4 (80 mmol) and raw material A5 (80 mmol) were added to a reaction flask, and tetrakistriphenylphosphine palladium (0.8 mmol) and potassium carbonate (160 mmol) were added. Then, 400 mL of a mixture of toluene, ethanol, and water (toluene: ethanol: water = 2:1:1 by volume) was added. The temperature was raised to 90°C and the reaction was continued for 16 h. The temperature was lowered to 40-50°C, the liquids were separated, the toluene layer was washed once with water, dried over anhydrous sodium sulfate, and concentrated to obtain an oil. A mixture of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:4 by volume) was passed through a silica gel column to obtain a white solid A6 (14.9 g, yield: 94.8%, MW: 196.61);

[0153] (5) Compound A6 (77 mmol) was dissolved in 100 mL of DMF, and NBS (0.093 mol) was added portionwise. The temperature was raised to 100°C and the reaction was allowed to proceed for 24 h. The reaction solution was poured into 300 mL of cold water and stirred. A large amount of solid precipitated, which was filtered to obtain a dark product. A mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:4 by volume) was passed through a silica gel column to obtain a white solid A7 (19.2 g, yield: 90.8%, MW: 275.59).

[0154] (6) Under nitrogen protection, compound A7 (60 mmol) was added to a reaction flask, and PdCl2(dppf) 1.8 mmol, potassium acetate 120 mmol, and 1,4-dioxane 200 mL were added, respectively. The temperature was raised to 90°C and the reaction was carried out for 6 h. The mixture was then cooled to room temperature, filtered, and the insoluble matter was removed. The filtrate was then dried to obtain a black oil. A mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 1:4 by volume) was passed through a silica gel column to obtain the target product, starting material A (17.6 g, yield: 90.8%, MW: 322.58).

[0155] The target product raw material A is used for the synthesis of electron transport materials in the following examples.

[0156] Example 1

[0157] This embodiment provides an electron transport material, whose chemical formula is shown as ET-3 above, and the synthesis route is as follows:

[0158]

[0159] The specific steps are:

[0160] (1) Under nitrogen protection, raw material A (55 mmol) and raw material Q (50 mmol) were added to a three-necked reaction flask, and tetrakis(triphenylphosphine palladium) (0.50 mmol) and potassium carbonate (100 mmol) were added respectively. Then, 120.00 mL of a mixed solution of toluene, ethanol and water (toluene: ethanol: water = 2: 1: 1 by volume) was added, and the mixture was heated to 90° C. and refluxed overnight. After the reaction was completed, the reaction solution was cooled to 40-50° C., the water layer was separated, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was spin-dried to obtain a solid organic matter, which was completely dissolved in dichloromethane and then slowly added dropwise to a petroleum ether solution. The mixture was stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, which was washed with anhydrous ethanol and petroleum ether in sequence and dried to obtain intermediate 1 (13.8 g, yield: 76.0%, MW: 364.80);

[0161] (2) Under nitrogen protection, intermediate 1 (30 mmol) was added to a reaction flask, followed by potassium carbonate (33 mmol) and DMSO (80.00 ml). The temperature was raised to 160°C and the reaction was allowed to proceed for 24 h. The reaction solution was cooled to room temperature, stirred with water, and extracted with ethyl acetate. The extract was washed once with water, dried over anhydrous magnesium sulfate, and dried to obtain an oily substance. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain intermediate 2 (6.8 g, yield: 66.5%, MW: 344.78).

[0162] (3) Under nitrogen protection, intermediate 2 (15 mmol) and raw material M (16.5 mmol) were dissolved in 90.00 mL of toluene solution, tris(dibenzylideneacetone)dipalladium (0.15 mmol), tri-tert-butylphosphine (0.75 mmol) and sodium tert-butoxide (30 mmol) were added, stirred evenly, heated to reflux, and reacted for 5 h; after the reaction was completed, the temperature was slightly lowered, and the mixture was filtered using diatomaceous earth to remove salt and catalyst. After the filtrate was cooled to room temperature, it was washed three times with water, the organic phase was retained, and the aqueous phase was then extracted with ethyl acetate; after the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (by volume ratio, dichloromethane: petroleum ether = 10:4) to obtain compound ET-3 (5.4 g, yield: 51.9%, Mw: 693.77).

[0163] The obtained compound ET-3 was tested and analyzed, and the results were as follows:

[0164] HPLC purity: >99%;

[0165] Mass spectrometry test: calculated value: 693.89, tested value: 693.93;

[0166] Elemental analysis:

[0167] Calculated values: C, 88.28; H, 5.67; N, 6.06;

[0168] Found: C, 88.39; H, 5.73; N, 6.15.

[0169] Example 2

[0170] This embodiment provides an electron transport material, whose chemical formula is shown as ET-75 above, and the synthesis route is as follows:

[0171]

[0172] The specific steps are:

[0173] (1) Under nitrogen protection, raw material A (55 mmol) and raw material Q (50 mmol) were added to a three-necked reaction flask, and tetrakis(triphenylphosphine palladium) (0.50 mmol) and potassium carbonate (100 mmol) were added respectively. Then, 120.00 mL of a mixed solution of toluene, ethanol and water (toluene: ethanol: water = 2: 1: 1 by volume) was added, and the mixture was heated to 90° C. and refluxed overnight. After the reaction was completed, the reaction solution was cooled to 40-50° C., the water layer was separated, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was spin-dried to obtain a solid organic matter, which was completely dissolved in dichloromethane and then slowly added dropwise to a petroleum ether solution. The mixture was stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, which was washed with anhydrous ethanol and petroleum ether in sequence and dried to obtain intermediate 1 (13.4 g, yield: 73.8%, MW: 364.91);

[0174] (2) Under nitrogen protection, intermediate 1 (30 mmol) was added to a reaction flask, followed by potassium carbonate (33 mmol) and DMSO (80.00 mL). The temperature was raised to 160°C and the reaction was continued for 24 h. The reaction solution was cooled to room temperature, stirred with water, and extracted with ethyl acetate. The extract was washed with water once, dried over anhydrous magnesium sulfate, and dried to obtain an oil. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain intermediate 2 (7.2 g, yield: 69.5%, MW: 344.83).

[0175] (3) Under nitrogen protection, intermediate 2 (15 mmol) and raw material M (16.5 mmol) were added to a reaction flask, and then Pd(oAc)2 (0.75 mmol), cesium carbonate (30 mmol), and ligand X-PHOS (1.20 mmol) were added respectively. A mixed solution of 100.00 mL of ethylene glycol dimethyl ether and water (ethylene glycol dimethyl ether: water = 2:1 by volume) was added, and the temperature was raised to reflux for 16 h. After the reaction was completed, the reaction solution was cooled to 40-50°C, the water layer was separated, and the organic layer was dried over anhydrous sodium sulfate. The organic layer was spin-dried to obtain a black substance. The remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (dichloromethane: petroleum ether = 10:4 by volume) to obtain compound ET-75 (5.2 g, yield: 50.2%, Mw: 693.77).

[0176] The obtained compound ET-3 was tested and analyzed, and the results were as follows:

[0177] HPLC purity: >99.5%;

[0178] Mass spectrometry test: calculated value: 693.89, tested value: 693.71;

[0179] Elemental analysis:

[0180] Calculated values: C, 88.28; H, 5.67; N, 6.06;

[0181] Found: C, 88.35; H, 5.71; N, 6.12.

[0182] It should be noted that the synthesis methods of the electron transport materials in the other embodiments are similar to those in Examples 1-2 and will not be described in detail herein. The present invention further selects ET-5, ET-8, ET-12, ET-15, ET-18, ET-21, ET-23, ET-26, ET-29, ET-33, ET-38, ET-41, ET-45, ET-49, ET-53, ET-56, ET-59, ET-61, ET-62, ET-66, ET-68, ET-70, ET-72, ET-74, ET-77, ET-80, ET-83 and ET-92 in the Summary of the Invention as the electron transport materials in Examples 3-30, and their corresponding mass spectrometry test values, purities and yields are shown in Table 1 below:

[0183] Table 1

[0184]

[0185]

[0186] Application Example 1

[0187] The electron transport material obtained in Example 1 was used to prepare an organic electroluminescent device. The preparation method was as follows:

[0188] a. ITO anode: Wash the ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 150nm in distilled water twice, ultrasonically wash for 30 minutes, then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes, and then transfer it to a spin dryer for drying. Finally, bake it in a vacuum oven at 220℃ for 2 hours. After baking, cool it down and it can be used. Use this substrate as the anode and use an evaporation machine to carry out the evaporation device process, and evaporate other functional layers on it in sequence;

[0189] b. HIL (hole injection layer): The hole injection layer materials P-dopant and HT were vacuum evaporated at a deposition rate of 98:2. The deposition rate ratio of HT to P-dopant was 98:2, and the thickness was 10 nm. The chemical formulas of P-dopant and HT are as follows:

[0190]

[0191] c. HTL (hole transport layer): At a deposition rate of 100 nm, 120 nm of HT was vacuum-deposited on the hole injection layer as a hole transport layer.

[0192] d. Prime (luminous auxiliary layer): At a deposition rate of , 10 nm of prime was vacuum-deposited on the hole transport layer as a light-emitting auxiliary layer. The chemical formula of the prime is as follows:

[0193]

[0194] e. EML (light-emitting layer): Then on the above-mentioned light-emitting auxiliary layer, The host material (Host) and the dopant material (Dopant) are vacuum-deposited at a deposition rate of 25 nm as the light-emitting layer, wherein the deposition rate ratio of the Host to the Dopant is 97:3. The chemical formulas of the Host and the Dopant are as follows:

[0195]

[0196] f. HB (hole blocking layer): The evaporation rate is 5.0 nm, and HB is vacuum-deposited as a hole blocking layer. The chemical formula of HB is as follows:

[0197]

[0198] g. ETL (Electron Transport Layer): The ET-3 and Liq compounds were vacuum-deposited at a deposition rate of 35 nm to form an electron transport layer. The deposition rate ratio of the ET-3 and Liq compounds was 50:50. The chemical formula of ET-3 is as described in the Summary of the Invention and will not be repeated here. The chemical formula of Liq is as follows:

[0199]

[0200] h. EIL (electron injection layer): The evaporation rate is 1.0 nm, and a Yb film layer is evaporated to form an electron injection layer;

[0201] i. Cathode: 18 nm of magnesium and silver were evaporated at a deposition rate ratio of 1:9 to obtain an OLED device;

[0202] j. Light extraction layer: At a deposition rate of , CPL with a thickness of 70 nm was vacuum-deposited on the cathode as a light extraction layer, wherein the chemical formula of CPL is;

[0203]

[0204] k. Package the substrate after vapor deposition. First, use the glue coating equipment to coat the cleaned cover with UV glue, then move the coated cover to the pressing section, place the vapor deposited substrate on the upper end of the cover, and finally bond the substrate and cover together using the bonding equipment, while completing the UV glue curing process.

[0205] The structure of the prepared organic electroluminescent device is:

[0206] ITO / Ag / ITO / HT: P-dopant (10nm, 2%) / HT (120nm) / prime (10nm) / Host: Dopant (25nm, 3%) / HB (5nm) / ET: Liq (35nm, 50%) / Yb (1nm) / Mg: Ag (18nm, 1:9) / CPL (70nm).

[0207] Application Example 2-30

[0208] This application example 2-30 provides 29 organic electroluminescent devices. The only difference from application example 1 is that the compound ET-3 used in the organic electroluminescent device is replaced by the compound prepared in Example 2-30 and evaporated into the electron transport layer in the organic electroluminescent device. The remaining parameters and steps are consistent with application example 1.

[0209] Comparative Application Examples 1-2

[0210] This comparative application example provides two organic electroluminescent devices. The only difference from Application Example 1 is that the compound ET-3 used in the organic electroluminescent device is replaced by comparative compound A and comparative compound B, respectively, which are evaporated into the electron transport layer of the organic electroluminescent device. The remaining parameters and steps are consistent with those of Application Example 1.

[0211] The chemical formulas of comparative compound A and comparative compound B are shown below:

[0212]

[0213] The driving voltage, luminous efficiency, BI value and lifespan of the organic electroluminescent devices obtained in the above application examples 1-30 and comparative application examples 1-2 were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below:

[0214] Table 2

[0215]

[0216]

[0217] As can be seen from the data in the above table, the organic electroluminescent device prepared using the electron transport layer material provided by the present invention as the electron transport layer has a lower driving voltage than the organic electroluminescent device prepared using comparative compound A or comparative compound B as the electron transport layer, and the luminous efficiency and life of the device are significantly improved.

[0218] The above description of the disclosed embodiments will enable one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be readily apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention is not limited to the embodiments shown herein but is to be construed in the widest manner consistent with the principles and novel features disclosed herein.

Claims

1. A compound, characterized in that The structural formula of the compound is selected from any one of the following formulae:

2. Use of the compound according to claim 1 in the preparation of an organic electroluminescent device, an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.

3. An organic electroluminescent device, characterized in that: comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode; The organic layer includes the compound of claim 1 .

4. The organic electroluminescent device according to claim 3, characterized in that: The organic layer includes any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer or a capping layer.

5. The organic electroluminescent device according to claim 4, characterized in that: The electron transport layer includes any one or more of an electron buffer layer, a hole blocking layer, an electron transport base layer or an electron injection base layer.

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