A fused-ring compound and its application, and an organic electroluminescent device.

Abstract

This invention relates to the field of organic electroluminescent devices, and discloses a fused-ring compound and its applications, as well as an organic electroluminescent device. The compound has the structural formula shown in formula (I). When the compound provided by this invention is used as the electron transport layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency. When used as one of the red light host materials in the light-emitting layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent device technology, specifically to a fused ring compound and its application, and an organic electroluminescent device. Background Technology

[0002] Currently, the emissive layer of high-efficiency OLEDs mainly uses organic phosphorescent materials. This is because the radiative transition of triplet excitons in most organic molecules is forbidden, which is not conducive to the light emission of the device. However, the spin-orbit coupling effect of heavy metal atoms makes the radiative transition from the originally spin-forbidden excited triplet state to the ground state locally allowed, effectively utilizing singlet and triplet excitons. Theoretically, the internal quantum efficiency can reach 100%, and the intersystem crossing probability from the singlet excited state to the triplet excited state is increased, resulting in efficient phosphorescence. However, due to the long lifetime of triplet excitons, high-concentration quenching is easily caused. Using host-guest doping can effectively avoid high-concentration quenching, thus requiring the development of high-performance host and guest materials.

[0003] Existing materials used to fabricate red light devices result in high driving voltages and low efficiency, failing to meet the demands of market development. Therefore, providing a high-efficiency, low-driving-voltage red light source material for organic electroluminescent devices has become an urgent problem to be solved. Furthermore, red light, as one of the three primary colors, is crucial for OLED displays. Therefore, developing a high-performance red light source is of great significance.

[0004] As is well known, hole mobility is generally higher than electron mobility, so it is crucial to find an electron transport material with a suitable energy level and high electron mobility.

[0005] Therefore, the development of high-performance electron transport materials is of great significance. Summary of the Invention

[0006] The purpose of this invention is to overcome the problems of high driving voltage and low luminous efficiency in organic electroluminescent devices.

[0007] To achieve the above objectives, a first aspect of the present invention provides a fused ring compound having the structural formula shown in formula (I);

[0008]

[0009] In equation (I),

[0010] Either position A or B is connected to the structure shown in formula (I1) via an L linker group, with or without the presence of such a linker group; the remaining position A or B is connected to C... 6-20 The aryl group is linked, or there is no linking group;

[0011] X21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-12 Alkyl group; R 22 Does not exist, or R 22 Selected from C 6-20 aryl;

[0012] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, C 6-20 The aryl or dibenzoheterocyclic group; or two R groups on at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0013] The L-linking group is composed of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, or C. 6-20 Provided by any one of the aromatic structures.

[0014] A second aspect of the present invention provides the application of the fused-ring compound described in the first aspect in organic electroluminescent devices.

[0015] A third aspect of the present invention provides an organic electroluminescent device containing one or more of the fused-ring compounds described in the first aspect, wherein the fused-ring compounds are present in at least one layer of the electron transport layer, the light-emitting layer, and the hole blocking layer of the organic electroluminescent device.

[0016] When the compound provided by this invention is used as the electron transport layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency.

[0017] When the compound provided by this invention is used as one of the red light host materials in the light-emitting layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency. Detailed Implementation

[0018] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0019] For the structural formulas (I) and (I1) of the present invention, the semi-ring structure or ring structure indicated by the dashed line represents the conjugate structure.

[0020] The C of this invention 6-20 The aryl group refers to an aryl group with a total number of carbon atoms of 6-20, including but not limited to phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, etc. (Regarding C...) 6-12 The aryl group has a similar definition, only the total number of carbon atoms is different.

[0021] The C of this invention 1-12 Alkyl groups refer to alkyl groups with a total number of carbon atoms of 1-12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12), including straight-chain alkyl groups and branched-chain alkyl groups. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, etc. Regarding "C 1-10 Alkyl group, C 1-8 "alkyl" has a similar definition, only the total number of carbon atoms is different.

[0022] The dibenzoheterocyclic group described in this invention refers to a group that optionally contains N, O, or S elements.

[0023] The term "terphenyl" in this invention refers to a structure formed by three phenyl groups linked together. There are no special requirements for the connection method between the three phenyl groups, including but not limited to ortho-terphenyl, meta-terphenyl, and para-terphenyl.

[0024] The term "sequential bridging" as used in this invention refers to a polycyclic structure formed by two or more carbon rings or heterocycles arranged in a specific order with shared ring edges. For example, "the five ring structures in the A1 group are sequentially bridged benzene ring structure, pyrrole structure, benzene ring structure, pyrrole structure, and benzene ring structure" means that a polycyclic structure is formed by connecting the benzene ring structure, pyrrole structure, benzene ring structure, pyrrole structure, and benzene ring structure in the order of benzene ring structure, pyrrole structure, benzene ring structure, and benzene ring structure with shared ring edges, including but not limited to...

[0025] DMSO: Dimethyl sulfoxide

[0026] NBS: N-bromosuccinimide

[0027] DMA: Dimethylacetamide

[0028] KOAc: Potassium acetate

[0029] Pd(OAc)2: Palladium acetate

[0030] Pd2(dba)3: Tris(dibenzylacetone)dipalladium

[0031] Pd(dppf)Cl2: 1,1-bis(diphenylphosphino)ferrocene palladium dichloride

[0032] Pd(PPh3)4: Tetra(triphenylphosphine)palladium

[0033] ITO: Indium Tin Oxide

[0034] As previously described, a first aspect of the present invention provides a fused-ring compound having the structural formula shown in formula (I);

[0035]

[0036] In equation (I),

[0037] Either position A or B is connected to the structure shown in formula (I1) via an L linker group, with or without the presence of such a linker group; the remaining position A or B is connected to C... 6-20 The aryl group is linked, or there is no linking group;

[0038] X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-12 Alkyl group; R 22 Does not exist, or R 22 Selected from C 6-20 aryl;

[0039] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, C 6-20 The aryl or dibenzoheterocyclic group; or two R groups on at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0040] The L-linking group is composed of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, or C. 6-20Provided by any one of the aromatic structures.

[0041] According to a preferred embodiment In equation (I),

[0042] Either position A or B is connected to the structure shown in formula (I1) via an L linker group, with or without the presence of such a linker group; the remaining position A or B is connected to C... 6-12 The aryl group is linked, or there is no linking group;

[0043] X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-10 Alkyl group; R 22 Does not exist, or R 22 Selected from C 6-12 aryl;

[0044] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, C 6-12 aryl, dibenzothiophene, dibenzofuranyl; or two R atoms in at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0045] The L-linking group is composed of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, or C. 6-12 Provided by any one of the aromatic structures.

[0046] According to another preferred embodiment In equation (I),

[0047] Either position A or position B is connected to the structure shown in formula (I1) by an L linking group, which may or may not be present; the remaining position A or position B is connected to a phenyl or naphthyl group, or there is no linking group.

[0048] X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-8 Alkyl group; R 22Does not exist, or R 22 Selected from phenyl, biphenyl, and naphthyl;

[0049] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, phenyl, biphenyl, naphthyl, dibenzothiophene, dibenzofuranyl; or two R atoms from at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0050] The L linking group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, and naphthalene.

[0051] According to a particularly preferred embodiment The compounds with the structure shown in formula (I) are selected from any of the following:

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] Preferably In equation (I),

[0067] Position A is connected to the structure shown in formula (I1) by an L linking group, which may or may not be present; position B is connected to a phenyl or naphthyl group.

[0068] X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-8 Alkyl group; R 22 Does not exist, or R 22 Selected from phenyl, biphenyl, and naphthyl;

[0069] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, phenyl, biphenyl, naphthyl, dibenzothiophene, dibenzofuranyl; or two R atoms from at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0070] The L linking group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, and naphthalene.

[0071] More preferably The compound with the structure shown in formula (I) is selected from any one of the following:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084] Preferably In equation (I),

[0085] Position B is connected to the structure shown in formula (I1) by an L linking group, which may or may not be present, while position A has no linking group.

[0086] X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-8 Alkyl group; R 22 Does not exist, or R 22 Selected from phenyl, biphenyl, and naphthyl;

[0087] X 11 X 12 X 13 X 14 Each is independently selected from N, -C(R) 11 )-;R 11 Selected from H, phenyl, biphenyl, naphthyl, dibenzothiophene, dibenzofuranyl; or two R atoms from at least one of the groups formed by two adjacent C atoms. 11 Together they form a benzene ring structure;

[0088] The L linking group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, and naphthalene.

[0089] More preferably The compound with the structure shown in formula (I) is selected from any one of the following:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] This invention does not impose any particular limitation on the specific methods for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of this invention by combining the specific structural formulas provided by this invention with conventional process routes in the field of organic synthesis. Furthermore, several examples are exemplarily listed below to illustrate the preparation methods of the compounds of this invention. Those skilled in the art can also obtain the specific preparation methods of all other compounds by changing the types of raw materials according to the preparation methods of the compounds described below. This invention will not further describe the preparation methods of all compounds in detail, and this should not be construed as a limitation of the invention.

[0096] As previously stated, a second aspect of the present invention provides the application of the fused-ring compound described in the first aspect in organic electroluminescent devices.

[0097] According to a preferred embodiment, the present invention provides an organic electroluminescent device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the one or more organic material layers contain at least one of the aforementioned compounds of the present invention.

[0098] In this invention, one of the first electrode and the second electrode is an anode, and the other is a cathode.

[0099] According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron injection layer, etc. as organic material layers.

[0100] As previously stated, a third aspect of the present invention provides an organic electroluminescent device containing one or more of the fused-ring compounds described in the first aspect, wherein the fused-ring compounds are present in at least one layer of the electron transport layer, the light-emitting layer, and the hole blocking layer of the organic electroluminescent device.

[0101] Preferably, the fused ring compound is present in the light-emitting layer of the organic electroluminescent device.

[0102] Preferably, the fused ring compound is present in the electron transport layer of the organic electroluminescent device.

[0103] In a preferred embodiment, the compound exists as a red light host material in the light-emitting layer of the organic electroluminescent device.

[0104] The inventors of this invention have discovered that when the compound of this invention is used as the electron transport layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency.

[0105] The inventors of this invention have discovered that when the compound of this invention is used as one of the red light host materials in the light-emitting layer of an organic electroluminescent device, it can significantly reduce the driving voltage of the organic electroluminescent device and improve the luminous efficiency.

[0106] Preferably, the fused-ring compound is present in the light-emitting layer of the organic electroluminescent device, and the light-emitting layer further contains a biscarbazole compound, and the molar ratio of the fused-ring compound to the biscarbazole compound is 1:0.42-1.0;

[0107] The biscarbazole compound contains at least two groups provided by the carbazole compound, and the carbazole compound may or may not contain R. h1 Substituents; R h1 The substituent is selected from at least one of phenyl, biphenyl, naphthyl, dibenzofuranyl, and dibenzothiopheneyl; optionally, an L-type substituent is present between any two adjacent groups provided by the carbazole compound. h Linking group; the L h The linking group is provided by at least one compound selected from benzene, biphenyl, terphenyl, dibenzofuran, and dibenzothiophene; or,

[0108] The biscarbazole compound is an A1 group, which is provided by a fused-ring compound containing five ring structures, wherein the five ring structures in the A1 group are sequentially bridged benzene ring, pyrrole ring, benzene ring, pyrrole ring, and benzene ring; and the A1 group may or may not contain R. h2 Substituents; R h2 The substituent is selected from at least one of phenyl, biphenyl, naphthyl, dibenzofuranyl, and dibenzothiopheneyl.

[0109] More preferably, the biscarbazole compound is selected from any one of the following:

[0110]

[0111]

[0112]

[0113]

[0114] Preferably, the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, which are stacked sequentially.

[0115] More preferably, the organic electroluminescent device includes an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and a capping layer, which are stacked sequentially.

[0116] The organic electroluminescent device of the present invention preferably employs a sublimation method to coat one or more layers. In this case, in a vacuum sublimation system, at a temperature of less than 10... -3 Pa, preferably less than 10 -6 The compound provided by the present invention is applied by vapor deposition at an initial pressure of Pa.

[0117] The organic electroluminescent device of the present invention is preferably coated with one or more layers by organic vapor deposition or by means of carrier gas sublimation. In this case, at 10 -6 The compound is applied under pressures ranging from Pa to 100 Pa. A particular example of this method is the organic vapor deposition printing method, in which the compound provided by the present invention is applied directly through a nozzle to form a device structure.

[0118] The organic electroluminescent device of the present invention preferably involves formulating the compound of the present invention into a solution and forming one or more layers by spin coating or by any printing method, such as screen printing, flexographic printing, inkjet printing, offset printing, and more preferably photoinitiated thermal imaging or inkjet printing. Typically, when fabricating multiple layers using this method, layer-to-layer destruction is likely to occur; that is, when one layer is completed and another layer is fabricated using the solution, the solvent in the solution can destroy the already formed layer, which is detrimental to the fabrication of organic electroluminescent devices. However, the compound provided by the present invention can undergo cross-linking under heating or ultraviolet exposure, thereby maintaining the integrity of the layers without destruction. The compound of the present invention can also be applied from a solution and subsequently cross-linked in a polymer network or immobilized in the corresponding layers.

[0119] The organic electroluminescent device of the present invention can be manufactured as a hybrid system by applying one or more layers through solution and by applying one or more other layers through vapor deposition.

[0120] According to some embodiments of the present invention, the anode material forming the anode is generally preferably a material with a high work function. For example, the anode material used in the present invention is selected from one or more of the following materials: metals, such as vanadium, chromium, copper and gold, or other alloys; metal oxides, such as zinc oxide, indium oxide, indium tin oxide, indium zinc oxide and tin dioxide; combinations of metals and oxides, such as zinc oxide and aluminum, but not limited thereto.

[0121] According to some embodiments of the present invention, the material forming the hole injection layer has the ability to transport holes. Therefore, the material of the hole injection layer has a hole injection effect in the anode, exhibits excellent hole injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and further has excellent thin film forming ability. The HOMO of the hole injection material is preferably between that of the anode material and the HOMO of the surrounding organic material layer.

[0122] According to some embodiments of the present invention, the material forming the hole transport layer is a material capable of receiving holes from the anode or hole injection layer, moving holes to the light-emitting layer, and having a high mobility for holes.

[0123] According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of the following: aromatic amine derivatives (e.g., NPB, SqMA1), hexaazabenzophenanthrene derivatives (e.g., HACTN), indolecarbazole derivatives, conductive polymers (e.g., PEDOT / PSS), phthalocyanine or porphyrin derivatives, dibenzoindofluoreneamine, and spirodifluoreneamine, but are not limited thereto.

[0124] According to some embodiments of the present invention, the hole injection layer and the hole transport layer may, for example, be formed using aromatic amine derivatives of the following general formula:

[0125]

[0126] The groups R1 to R9 in the above general formula are each independently selected from single bonds, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, fluorene, dimethylfluorene, spirodifluorene, carbazole, thiophene, benzo[a]thiophene, dibenzo[a]thiophene, furan, benzo[a]furan, dibenzo[a]furan, indole, indolecarbazole, indolecarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine, or triazine.

[0127] According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited; generally, compounds that meet the first and / or second condition below can be considered for use:

[0128] First: It has a shallower LUMO energy level (smaller absolute value), the purpose of which is to reduce the number of electrons leaving the luminescent layer, thereby increasing the probability of recombination of electrons and holes in the luminescent layer.

[0129] Second: It possesses a large triplet energy, the purpose of which is to reduce the number of excitons leaving the luminescent layer, thereby improving the efficiency of exciton conversion luminescence.

[0130] According to some embodiments of the present invention, the materials forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (e.g., NPB) and spirodifluoreneamine (e.g., SpMA2), wherein some electron blocking materials have structures similar to hole injection materials and hole transport materials.

[0131] According to some embodiments of the present invention, the luminescent material of the luminescent layer is a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes and electrons, and preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0132] According to some embodiments of the present invention, the light-emitting layer contains two host materials and two guest materials.

[0133] According to some embodiments of the present invention, one of the main materials is selected from the compounds described in the present invention.

[0134] According to some embodiments of the present invention, the guest material is preferably a compound that emits light via at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal-to-ligand charge transfer), HLCT (with hybrid CT states), and triplet-triplet annihilation methods.

[0135] According to some embodiments of the present invention, the guest material in the light-emitting layer includes, but is not limited to, perylene derivatives, anthracene derivatives, fluorene derivatives, stilbene aromatic derivatives, aromatic amine derivatives, organosilicon derivatives, organoboron derivatives, carbazole-triazine derivatives, acridine derivatives, ketone derivatives, sulfone derivatives, cyano derivatives, and xanthene derivatives.

[0136] In some preferred embodiments of the present invention, the sulfone derivatives have the following general formula:

[0137]

[0138] The ketone derivatives have the following general formula:

[0139]

[0140] In the general formulas of the above sulfone derivatives and ketone derivatives, R 20 R 21 R 22 and R 23Each group is independently selected from single bonds, hydrogen, deuterium, alkyl, benzene, diphenyl, terphenyl, tetraphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, benzo[a]phenanthrene, pyrene, fluorene, carbazole, thiophene, benzo[a]thiophene, dibenzo[a]thiophene, furan, benzo[a]furan, dibenzo[a]furan, indole, indolecarbazole, indolecarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine, or triazine, and groups represented by their substituted derivatives.

[0141] According to some embodiments of the present invention, the material of the hole blocking layer is preferably a compound having the following first and / or second condition:

[0142] First: It has a deeper HOMO energy level (larger absolute value), the purpose of which is to reduce the number of holes leaving the luminescent layer, thereby increasing the probability of recombination of electrons and holes in the luminescent layer.

[0143] Second: It possesses a large triplet energy, the purpose of which is to reduce the number of excitons leaving the luminescent layer, thereby improving the efficiency of exciton conversion luminescence.

[0144] According to some embodiments of the present invention, the material forming the hole blocking layer includes, for example, a phenanthroline derivative (e.g., Bphen, BCP), a benzo[a]phenanthrene derivative, a benzimidazole derivative, but is not limited thereto.

[0145] According to some embodiments of the present invention, the electron transport layer is selected from the compounds described in the present invention.

[0146] According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film forming ability. Electron injection layer materials include, for example, LiF, CsF, Cs₂CO₃, and LiQ, but are not limited to these.

[0147] According to some embodiments of the present invention, the cathode material is generally preferably a material with a small work function, which allows electrons to be smoothly injected into the organic material layer. The cathode material that can be used in this disclosure is selected from one or more of the following materials: Al, Mg and Ag.

[0148] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available products.

[0149] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, all raw materials used are commercially available products. Unless otherwise specified, room temperature as mentioned below refers to 25±1℃.

[0150] Preparation Example 1: Synthesis of Intermediate A

[0151]

[0152] Synthesis of intermediate A-1: ​​Naphthyl-2-amine (698.4 mmol) was added to a reactor, followed by the addition of dichloromethane (1,000 mL) and stirring. Benzoyl chloride (770 mmol) and pyridine (1,396.7 mmol) were added dropwise to the reactor and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with dichloromethane, water was removed with MgSO4, and intermediate A-1 was obtained by column chromatography (hexane:ethyl acrylate = 4:1 (v / v)) (yield: 97%).

[0153] Synthesis of intermediate A-2: Intermediate A-1 (677.4 mmol), FeCl3 (67.7 mmol), Na2S2O8 (680.0 mmol), pyridine (1,354.8 mmol), under a nitrogen stream, were mixed with DMSO (2100 ml) and stirred at 80 °C for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, dehydrated with MgSO4, and subjected to column chromatography (hexane:ethyl acrylate = 10:1 (v / v)) to give intermediate A-2 (yield: 64%).

[0154] Synthesis of intermediate A-3: Intermediate A-2 (433.6 mmol), NBS (433.6 mmol), and dichloromethane (1000 mL) were added dropwise to a stirred mixture under a nitrogen atmosphere at 0 °C and allowed to stand at room temperature for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and intermediate A-3 was obtained by column chromatography (hexane:ethyl acrylate = 6:1 (v / v)) (yield: 81%).

[0155] Synthesis of intermediate A-4: Intermediate A-3 (250.5 mmol), 2,5-dichlorophenol (300.6 mmol), Pd2(dba)3 (12.5 mmol), 2-bicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (25.1 mmol), Cs2CO3 (626.3 mmol), and xylene (1000 ml) were mixed under a nitrogen atmosphere and stirred at 120 °C for 8 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the resulting organic layer, intermediate A-4 was obtained by column chromatography (hexane:ethyl acrylate = 5:1 (v / v)) (yield: 63%).

[0156] Synthesis of intermediate A-5: Intermediate A-4 (157.8 mmol), Pd(OAc)2 (7.89 mmol), tricyclohexylphosphine fluoroborate (31.5 mmol), K2CO3 (315.7 mmol), and DMA (1000 ml) were mixed and stirred at 170 °C for 3 hours under a nitrogen atmosphere. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. The resulting organic layer was purified by column chromatography (hexane:ethyl acrylate = 4:1 (v / v)) after removing the solvent, yielding intermediate A-5 (yield: 54%).

[0157] Synthesis of Intermediate A: Intermediate A-5 (239.9 mmol) was mixed with pinacol diborate (263.9 mmol), Pd(dppf)Cl2 (12.0 mmol), KOAc (719.7 mmol), and 1,4-dioxane (1000 ml) under a nitrogen atmosphere and stirred at 130 °C for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, then water was removed with MgSO4, and purified by column chromatography (hexane:ethyl acrylate = 8:1 (v / v)) to give intermediate A (yield: 75%).

[0158] Mass spectrometry: C29H24BNO4, theoretical value: 461.18, measured value: 461.20. Elemental analysis: theoretical value: C: 75.50%, H: 5.24%, N: 3.04%, measured value: C: 75.51%, H: 5.25%, N: 3.05%.

[0159] Preparation Example 2: Synthesis of Intermediate B

[0160]

[0161] Synthesis of intermediate B-1: The synthesis method is the same as that of intermediate A-4, except that 2,5-dichlorophenol is replaced with 2,4-dichlorophenol to obtain intermediate B-1 (yield: 59%).

[0162] Synthesis of intermediate B-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate B-1 to obtain intermediate B-2 (yield: 51%).

[0163] Synthesis of intermediate B: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate B-2 to obtain intermediate B (yield: 78%).

[0164] Mass spectrometry: C29H24BNO4, theoretical value: 461.18, measured value: 461.19. Elemental analysis: theoretical value: C: 75.50%, H: 5.24%, N: 3.04%, measured value: C: 75.52%, H: 5.23%, N: 3.03%.

[0165] Preparation Example 3: Synthesis of Intermediate C

[0166]

[0167] Synthesis of intermediate C-1: The synthesis method is the same as that of intermediate A-1, except that benzoyl chloride is replaced with chlorobromocarbonyl to obtain intermediate C-1 (yield: 95%).

[0168] Synthesis of intermediate C-2: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate C-1 to obtain intermediate C-2 (yield: 65%).

[0169] Synthesis of intermediate C-3: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate C-2 to obtain intermediate C-3 (yield: 84%).

[0170] Synthesis of intermediate C-4: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates C-3 and 2-chlorophenol to obtain intermediate C-4 (yield: 66%).

[0171] Synthesis of intermediate C: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate C-4 to obtain intermediate C (yield: 56%).

[0172] Mass spectrometry: C17H8ClNO2, theoretical value: 293.02, measured value: 293.00. Elemental analysis: theoretical value: C: 69.52%, H: 2.75%, N: 4.77%, measured value: C: 69.50%, H: 2.74%, N: 4.75%.

[0173] Preparation Example 4: Synthesis of Intermediate D

[0174]

[0175] Synthesis of intermediate D-1: Intermediate A-1 (663.4 mmol) was added to a reactor, followed by toluene (2000 ml), and the mixture was stirred. Lawson's reagent (364.9 mmol) was added dropwise to the reactor, and the mixture was stirred at 110 °C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, water was removed with MgSO4, and intermediate D-1 was obtained by column chromatography (hexane:ethyl acrylate = 7:1 (v / v)) (yield: 93%).

[0176] Synthesis of intermediate D-2: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate D-1 to obtain intermediate D-2 (yield: 62%).

[0177] Synthesis of intermediate D-3: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate D-2 to obtain intermediate D-3 (yield: 83%).

[0178] Synthesis of intermediate D-4: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates D-3 and 2,4-dichlorophenol to obtain intermediate D-4 (yield: 67%).

[0179] Synthesis of intermediate D-5: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate D-4 to obtain intermediate D-5 (yield: 55%).

[0180] Synthesis of intermediate D: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate D-5 to obtain intermediate D (yield: 80%).

[0181] Mass spectrometry: C29H24BNO3S, theoretical value: 477.16, measured value: 477.20. Elemental analysis: theoretical value: C: 72.96%, H: 5.07%, N: 2.93%, measured value: C: 72.95%, H: 5.05%, N: 2.94%.

[0182] Preparation Example 5: Synthesis of Intermediate E

[0183]

[0184] Synthesis of intermediate E-1: The synthesis method is the same as that of intermediate A-1, except that benzoyl chloride is replaced with phenylbenzoyl chloride to obtain intermediate E-1 (yield: 92%).

[0185] Synthesis of intermediate E-2: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate E-1 to obtain intermediate E-2 (yield: 65%).

[0186] Synthesis of intermediate E-3: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate E-2 to obtain intermediate E-3 (yield: 81%).

[0187] Synthesis of intermediate E-4: The synthesis method is the same as that of intermediate A-4, except that intermediate A-3 is replaced with intermediate E-3 to obtain intermediate E-4 (yield: 63%).

[0188] Synthesis of intermediate E-5: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate E-4 to obtain intermediate E-5 (yield: 53%).

[0189] Synthesis of intermediate E: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate E-5 to obtain intermediate E (yield: 81%).

[0190] Mass spectrometry: C35H29BN2O3, theoretical value: 536.23, measured value: 536.22. Elemental analysis: theoretical value: C: 78.37%, H: 5.45%, N: 5.22%, measured value: C: 78.40%, H: 5.44%, N: 5.20%.

[0191] Preparation Example 6: Synthesis of Intermediate F

[0192]

[0193] Synthesis of intermediate F-1: The synthesis method is the same as that of intermediate A-4, except that 2,5-dichlorophenol is replaced with 2,5-dichlorobenzenethiol to obtain intermediate F-1 (yield: 66%).

[0194] Synthesis of intermediate F-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate F-1 to obtain intermediate F-2 (yield: 54%).

[0195] Synthesis of intermediate F: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate F-2 to obtain intermediate F (yield: 82%).

[0196] Mass spectrometry: C29H24BN2O3S, theoretical value: 477.16, measured value: 477.15. Elemental analysis: theoretical value: C: 72.96%, H: 5.07%, N: 2.93%, measured value: C: 72.95%, H: 5.06%, N: 2.94%.

[0197] Preparation Example 7: Synthesis of Intermediate G

[0198]

[0199] Synthesis of intermediate G-1: The synthesis method is the same as that of intermediate A-4, except that 2,5-dichlorophenol is replaced with 2,4-dichlorobenzenethiol to obtain intermediate G-1 (yield: 67%).

[0200] Synthesis of intermediate G-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate G-1 to obtain intermediate G-2 (yield: 57%).

[0201] Synthesis of intermediate G: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate G-2 to obtain intermediate G (yield: 79%).

[0202] Mass spectrometry: C29H24BN2O3S, theoretical value: 477.16, measured value: 477.17. Elemental analysis: theoretical value: C: 72.96%, H: 5.07%, N: 2.93%, measured value: C: 72.97%, H: 5.04%, N: 2.97%.

[0203] Preparation Example 8: Synthesis of Intermediate H

[0204]

[0205] Synthesis of intermediate H-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates C-3 and 2-chlorobenzyl mercaptan to obtain intermediate H-1 (yield: 64%).

[0206] Synthesis of intermediate H: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate H-1 to obtain intermediate H (yield: 56%).

[0207] Mass spectrometry: C17H8ClNOS, theoretical value: 309.00, measured value: 309.01. Elemental analysis: theoretical value: C: 65.91%, H: 2.60%, N: 4.52%, measured value: C: 65.90%, H: 2.61%, N: 4.50%.

[0208] Preparation Example 9: Synthesis of Intermediate I

[0209]

[0210] Synthesis of intermediate I-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates D-3 and 2,4-dichlorobenzenethiol to obtain intermediate I-1 (yield: 61%).

[0211] Synthesis of intermediate I-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate I-1 to obtain intermediate I-2 (yield: 57%).

[0212] Synthesis of intermediate I: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate I-2 to obtain intermediate I (yield: 80%).

[0213] Mass spectrometry: C29H24BNO2S2, theoretical value: 493.13, measured value: 493.15. Elemental analysis: theoretical value: C: 70.59%, H: 4.90%, N: 2.84%, measured value: C: 70.60%, H: 7.91%, N: 2.83%.

[0214] Preparation Example 10: Synthesis of Intermediate J

[0215]

[0216] Synthesis of intermediate J-1: The synthesis method is the same as that of intermediate A-4, except that intermediate A-3 and 2,5-dichlorophenol are replaced with 5-bromobenzo[b]naphtho[2,1-d]thiophene and N-phenylcarbamoyl chloride to obtain intermediate J-1 (yield: 62%).

[0217] Synthesis of intermediate J: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate J-1 to obtain intermediate J (yield: 54%).

[0218] Mass spectrometry: C23H13ClN2S, theoretical value: 384.05, measured value: 384.02. Elemental analysis: theoretical value: C: 71.77%, H: 3.40%, N: 7.28%, measured value: C: 71.76%, H: 3.41%, N: 7.29%.

[0219] Preparation Example 11: Synthesis of Intermediate K

[0220]

[0221] Synthesis of intermediate K-1: The synthesis method is the same as that of intermediate A-4, except that 2,5-dichlorophenol is replaced with 2,4-dichloro-1-isopropylbenzene to obtain intermediate K-1 (yield: 59%).

[0222] Synthesis of intermediate K-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate K-1 to obtain intermediate K-2 (yield: 51%).

[0223] Synthesis of intermediate K: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate K-2 to obtain intermediate K (yield: 76%).

[0224] Mass spectrometry: C32H30BNO3, theoretical value: 487.23, measured value: 487.22. Elemental analysis: theoretical value: C: 78.86%, H: 6.20%, N: 2.87%, measured value: C: 78.85%, H: 6.21%, N: 2.83%.

[0225] Preparation Example 12: Synthesis of Intermediate L

[0226]

[0227] Synthesis of intermediate L-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates D-3 and 2,4-dichloro-1-isocumene to obtain intermediate L-1 (yield: 60%).

[0228] Synthesis of intermediate L-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate L-1 to obtain intermediate L-2 (yield: 52%).

[0229] Synthesis of intermediate L: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate L-2 to obtain intermediate L (yield: 77%).

[0230] Mass spectrometry: C32H30BNO3S, theoretical value: 503.21, measured value: 503.20. Elemental analysis: theoretical value: C: 76.34%, H: 6.01%, N: 2.78%, measured value: C: 76.35%, H: 6.00%, N: 2.75%.

[0231] Preparation Example 13: Synthesis of Intermediate M

[0232]

[0233] Synthesis of intermediate M-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates E-3 and 2,4-dichloro-1-isopropylbenzene to obtain intermediate M-1 (yield: 61%).

[0234] Synthesis of intermediate M-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate M-1 to obtain intermediate M-2 (yield: 53%).

[0235] Synthesis of intermediate M: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate M-2 to obtain intermediate M (yield: 78%).

[0236] Mass spectrometry: C38H35BN2O2, theoretical value: 562.28, measured value: 562.30. Elemental analysis: theoretical value: C: 81.14%, H: 6.27%, N: 4.98%, measured value: C: 81.15%, H: 6.30%, N: 4.99%.

[0237] Preparation Example 14: Synthesis of Intermediate N

[0238]

[0239] Synthesis of intermediate N-1: The synthesis method is the same as that of intermediate A-1, except that naphth-2-amine is replaced with naphth-1-amine to obtain intermediate N-1 (yield: 93%).

[0240] Synthesis of intermediate N-2: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate N-1 to obtain intermediate N-2 (yield: 66%).

[0241] Synthesis of intermediate N-3: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate N-2 to obtain intermediate N-3 (yield: 82%).

[0242] Synthesis of intermediate N-4: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates N-3 and 2,4-dichlorophenol to obtain intermediate N-4 (yield: 62%).

[0243] Synthesis of intermediate N-5: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate N-4 to obtain intermediate N-5 (yield: 54%).

[0244] Synthesis of intermediate N: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate N-5 to obtain intermediate N (yield: 79%).

[0245] Mass spectrometry: C29H24BNO4, theoretical value: 461.18, measured value: 461.20. Elemental analysis: theoretical value: C: 75.50%, H: 5.24%, N: 3.04%, measured value: C: 75.49%, H: 5.25%, N: 3.05%.

[0246] Preparation Example 15: Synthesis of Intermediate O

[0247]

[0248] Synthesis of intermediate O-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates N-3 and 2,5-dichlorothiophenol to obtain intermediate O-1 (yield: 63%).

[0249] Synthesis of intermediate O-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate O-1 to obtain intermediate O-2 (yield: 55%).

[0250] Synthesis of intermediate O: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate O-2 to obtain intermediate O (yield: 80%).

[0251] Mass spectrometry: C29H24BNO3S, theoretical value: 477.16, measured value: 477.15. Elemental analysis: theoretical value: C: 72.96%, H: 5.07%, N: 2.93%, measured value: C: 72.95%, H: 5.05%, N: 2.91%.

[0252] Preparation Example 16: Synthesis of Intermediate P

[0253]

[0254] Synthesis of intermediate P-1: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates N-3 and 2,4-dichloro-1-isopropylbenzene to obtain intermediate P-1 (yield: 60%).

[0255] Synthesis of intermediate P-2: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate P-1 to obtain intermediate P-2 (yield: 50%).

[0256] Synthesis of intermediate P: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate P-2 to obtain intermediate P (yield: 78%).

[0257] Mass spectrometry: C32H30BNO3, theoretical value: 487.23, measured value: 487.24. Elemental analysis: theoretical value: C: 78.86%, H: 6.20%, N: 2.87%, measured value: C: 78.85%, H: 6.21%, N: 2.88%.

[0258] Preparation Example 17: Synthesis of Intermediate Q

[0259]

[0260] Synthesis of intermediate Q-1: The synthesis method is the same as that of intermediate A-1, except that benzoyl chloride and naphth-2-amine are replaced with chlorobromocarbonyl and naphth-1-amine to obtain intermediate Q-1 (yield: 90%).

[0261] Synthesis of intermediate Q-2: The synthesis method is the same as that of intermediate D-1, except that intermediate A-1 is replaced with intermediate Q-1 to obtain intermediate Q-2 (yield: 91%).

[0262] Synthesis of intermediate Q-3: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate Q-2 to obtain intermediate Q-3 (yield: 61%).

[0263] Synthesis of intermediate Q-4: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate Q-3 to obtain intermediate Q-4 (yield: 82%).

[0264] Synthesis of intermediate Q-5: The synthesis method is the same as that of intermediate A-4, except that intermediates A-3 and 2,5-dichlorophenol are replaced with intermediates Q-4 and 1-chloro-2-isopropylbenzene to obtain intermediate Q-5 (yield: 59%).

[0265] Synthesis of intermediate Q: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate Q-5 to obtain intermediate Q (yield: 52%).

[0266] Mass spectrometry: C20H14ClNS, theoretical value: 335.05, measured value: 335.04. Elemental analysis: theoretical value: C: 71.52%, H: 4.20%, N: 4.17%, measured value: C: 71.52%, H: 4.21%, N: 4.15%.

[0267] Preparation Example 18: Synthesis of Intermediate R

[0268]

[0269] Synthesis of intermediate R-1: The synthesis method is the same as that of intermediate A-1, except that benzoyl chloride and naphth-2-amine are replaced with phenylbenzoyl chloride and naphth-1-amine to obtain intermediate R-1 (yield: 89%).

[0270] Synthesis of intermediate R-2: The synthesis method is the same as that of intermediate A-2, except that intermediate A-1 is replaced with intermediate R-1 to obtain intermediate R-2 (yield: 60%).

[0271] Synthesis of intermediate R-3: The synthesis method is the same as that of intermediate A-3, except that intermediate A-2 is replaced with intermediate R-2 to obtain intermediate R-3 (yield: 81%).

[0272] Synthesis of intermediate R-4: The synthesis method is the same as that of intermediate A-4, except that intermediate A-3 and 2,5-dichlorophenol are replaced with intermediate R-3 and 2,4-dichloro-1-isopropylbenzene to obtain intermediate R-4 (yield: 57%).

[0273] Synthesis of intermediate R-5: The synthesis method is the same as that of intermediate A-5, except that intermediate A-4 is replaced with intermediate R-4 to obtain intermediate R-5 (yield: 53%).

[0274] Synthesis of intermediate R: The synthesis method is the same as that of intermediate A, except that intermediate A-5 is replaced with intermediate R-5 to obtain intermediate R (yield: 77%).

[0275] Mass spectrometry: C38H35BN2O2, theoretical value: 562.28, measured value: 562.30. Elemental analysis: theoretical value: C: 81.14%, H: 6.27%, N: 4.98%, measured value: C: 81.15%, H: 6.30%, N: 4.99%.

[0276] Example 1: Synthesis of Compound 3

[0277]

[0278] Synthesis of Compound 3: Intermediate A (270.4 mmol), 2-bromo-4,6-diphenylpyrimidine (324.5 mmol), Pd(PPh3)4 (13.5 mmol), K2CO3 (540.8 mmol), and 1,4-dioxane / H2O (1000 ml / 200 ml) were mixed under a nitrogen stream and stirred at 120 °C for 4 hours. After the reaction was complete, the mixture was extracted with dichloromethane, MgSO4 was added, and the mixture was filtered. After removing the solvent from the obtained organic layer, Compound 3 was purified by column chromatography (hexane:ethyl acrylate = 6:1 (v / v)) to give Compound 3 (yield: 76%).

[0279] Mass spectrometry: C39H23N3O2, theoretical value: 565.18, measured value: 565.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.59 (9H, m), 7.60~7.69 (3H, m), 7.75~7.80 (1H, m), 7.80~7.88 (2H, m), 7.90~7.97 (4H, m), 8.14~8.24 (4H, m).

[0280] Example 2: Synthesis of Compound 17

[0281]

[0282] Synthesis of compound 17: The synthesis method was the same as that of compound 3, except that 2-bromo-4,6-diphenylpyrimidine was replaced with 2-bromo-4,6-diphenyltriazine to obtain compound 17 (yield: 77%).

[0283] Mass spectrometry: C38H22N4O2, theoretical value: 566.17, measured value: 566.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.40~7.50(8H, m), 7.51~7.56(1H, m), 7.57~7.66(3H, m), 7.72~7.84(3H, m), 8.11~8.18(2H, m), 8.27~8.37(5H, m).

[0284] Example 3: Synthesis of Compound 32

[0285]

[0286] Synthesis of compound 32: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenylpyrimidine were replaced with intermediate B and 2-([1,1'-biphenyl]-4-yl)-4-bromo-6-phenyl-1,3,5-triazine to obtain compound 32 (yield: 77%).

[0287] Mass spectrometry: C44H26N4O2, theoretical value: 642.21, measured value: 642.19. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.22~7.29(4H, m), 7.29~7.57(11H, m), 7.72~7.78(4H, m), 7.80~7.88(2H, m), 7.92~8.01(5H, m).

[0288] Example 4: Synthesis of Compound 42

[0289]

[0290] Synthesis of Intermediate 42-1: 2,4-Bis([1,1'-biphenyl]-4-yl)-6-bromo-1,3,5-triazine (239.9 mmol) was mixed with pinacol diboronate (263.9 mmol), Pd(dppf)Cl2 (12.0 mmol), KOAc (719.7 mmol) and 1,4-dioxane (1000 mL) under a nitrogen atmosphere and stirred at 130 °C for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, then water was removed with MgSO4, and purified by column chromatography (hexane:ethyl acrylate = 8:1 (v / v)) to give intermediate 42-1 (yield: 81%).

[0291] Synthesis of compound 42: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenylpyrimidine are replaced with intermediate C and intermediate 42-1 to obtain compound 42 (yield: 75%).

[0292] Mass spectrometry: C44H26N4O2, theoretical value: 642.21, measured value: 642.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.22~7.29 (4H, m), 7.29~7.57 (11H, m), 7.72~7.78 (4H, m), 7.80~7.88 (2H, m), 7.92~8.01 (5H, m).

[0293] Example 5: Synthesis of Compound 54

[0294]

[0295] Synthesis of compound 54: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate B and 2-bromo-4-phenylquinazoline to obtain compound 54 (yield: 76%).

[0296] Mass spectrometry: C37H21N3O2, theoretical value: 539.16, measured value: 539.15. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.44~7.59(4H, d), 7.60~7.72(7H, m), 7.75~7.88(5H, m), 7.98~8.03(1H, m), 8.11~8.22(3H, m), 8.64~8.66(1H, m).

[0297] Example 6: Synthesis of Compound 90

[0298]

[0299] Synthesis of compound 90: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate G and 2-(biphenyl-3-yl)-4-chloro-6-phenyl-1,3,5-triazine to obtain compound 90 (yield: 75%).

[0300] Mass spectrometry: C44H26N4OS, theoretical value: 658.18, measured value: 658.19. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.37~7.54 (7H, m), 7.57~7.71 (7H, m), 7.72~7.78 (2H, m), 7.81~7.86 (1H, m), 7.97~8.01 (1H, d), 8.13~8.22 (3H, m), 8.32~8.41 (4H, m), 8.96~8.98 (1H, d).

[0301] Example 7: Synthesis of Compound 103

[0302]

[0303] Synthesis of intermediate 103-1: 1-Bromo-4-chlorodibenzofuran (239.9 mmol) was mixed with pinacol diboronate (263.9 mmol), Pd(dppf)Cl2 (12.0 mmol), KOAc (719.7 mmol), and 1,4-dioxane (1000 mL) under a nitrogen atmosphere and stirred at 130 °C for 12 hours. After the reaction was complete, the mixture was extracted with ethyl acetate, water was removed with MgSO4, and the intermediate 103-1 was purified by column chromatography (hexane:ethyl acrylate = 8:1 (v / v)) to obtain intermediate 103-1 (yield: 79%).

[0304] Synthesis of intermediate 103-2: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate 103-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain intermediate 103-2 (yield: 77%).

[0305] Synthesis of intermediate 103-3: The synthesis method is the same as that of intermediate 103-1, except that 1-bromo-4-chlorodibenzofuran is replaced with intermediate 103-2 to obtain intermediate 103-3 (yield: 79%).

[0306] Synthesis of compound 103: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate 103-3 and intermediate H to obtain compound 103 (yield: 69%).

[0307] Mass spectrometry: C44H24N4O2S, theoretical value: 672.16, measured value: 672.18. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.26~7.34 (2H, m), 7.35~7.45 (1H, m), 7.46~7.56 (9H, m), 7.57~7.67 (1H, m), 7.73~7.88 (4H, m), 7.95~8.00 (1H, m), 8.13~8.18 (1H, m), 8.31~8.40 (4H, m), 8.42~8.47 (1H, m).

[0308] Example 8: Synthesis of Compound 117

[0309]

[0310] Synthesis of compound 117: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate F and 2-chloro-3-phenylquinoxaline to obtain compound 117 (yield: 74%).

[0311] Mass spectrometry: C37H21N3OS, theoretical value: 555.14, measured value: 555.15. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.28~7.36 (2H, d), 7.44~7.51 (1H, m), 7.55~7.71 (7H, m), 7.76~7.87 (3H, m), 7.99~8.06 (3H, m), 8.13~8.26 (4H, m), 8.83~8.85 (1H, m).

[0312] Example 9: Synthesis of Compound 123

[0313]

[0314] Synthesis of compound 123: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate K and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 123 (yield: 71%).

[0315] Mass spectrometry: C41H28N4O, theoretical value: 592.23, measured value: 592.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.80~1.84 (6H, s), 7.30~7.38 (1H, m), 7.46~7.54 (6H, m), 7.58~7.69 (4H, m), 7.76~7.80 (1H, m), 7.94~7.99 (1H, d), 8.04~8.08 (1H, m), 8.15~8.21 (2H, m), 8.22~8.26 (1H, m), 8.32~8.40 (4H, m), 8.97~8.99 (1H, d).

[0316] Example 10: Synthesis of Compound 133

[0317]

[0318] Synthesis of compound 133: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate K and 4-chloro-2-phenylquinazoline to obtain compound 133 (yield: 75%).

[0319] Mass spectrometry: C40H27N3O, theoretical value: 565.22, measured value: 565.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.78~1.82 (6H, s), 7.24~7.31 (1H, m), 7.40~7.51 (4H, m), 7.53~7.63 (4H, m), 7.69~7.76 (2H, m), 7.87~7.92 (2H, m), 7.97~8.01 (1H, m), 8.04~8.13 (3H, m), 8.14~8.19 (1H, m), 8.24~8.31 (2H, m), 8.63~8.65 (1H, d).

[0320] Example 11: Synthesis of Compound 147

[0321]

[0322] Synthesis of compound 147: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate D and 2-(biphenyl-3-yl)-4-chloro-6-phenyl-1,3,5-triazine to obtain compound 147 (yield: 73%).

[0323] Mass spectrometry: C44H26N4OS, theoretical value: 658.18, measured value: 658.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.37~7.56 (10H, m), 7.58~7.78 (7H, m), 7.82~7.86 (1H, m), 7.99~8.07 (2H, m), 8.14~8.18 (1H, m), 8.32~8.41 (4H, m), 8.79~8.81 (1H, d).

[0324] Example 12: Synthesis of Compound 168

[0325]

[0326] Synthesis of compound 168: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate I and 2-(4-chloro-1-naphthyl)-4,6-diphenyl-1,3,5-triazine to obtain compound 168 (yield: 80%).

[0327] Mass spectrometry: C48H28N4S2, theoretical value: 724.18, measured value: 724.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.30~7.44 (2H, m), 7.46~7.58 (10H, m), 7.60~7.68 (2H, m), 7.76~7.80 (1H, d), 7.97~8.07 (3H, m), 8.10~8.20 (3H, m), 8.32~8.40 (4H, m), 8.92~8.97 (2H, m), 9.00~9.04 (1H, m).

[0328] Example 13: Synthesis of Compound 178

[0329]

[0330] Synthesis of compound 178: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate L and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 178 (yield: 75%).

[0331] Mass spectrometry: C41H28N4S, theoretical value: 608.20, measured value: 608.21. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.80~1.84 (6H, s), 7.29~7.33 (1H, m), 7.45~7.55 (10H, m), 7.77~7.79 (1H, m), 7.83~7.88 (2H, m), 7.91~7.94 (1H, d), 8.01~8.05 (2H, m), 8.34~8.38 (4H, m), 8.97~8.99 (1H, d).

[0332] Example 14: Synthesis of Compound 181

[0333]

[0334] Synthesis of compound 181: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate E and 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine to obtain compound 181 (yield: 72%).

[0335] Mass spectrometry: C50H31N5O, theoretical value: 717.25, measured value: 717.24. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.22~7.28 (2H, m), 7.35~7.66 (16H, m), 7.68~7.87 (5H, m), 7.93~7.99 (2H, m), 8.32~8.40 (5H, m), 8.48~8.54 (1H, m).

[0336] Example 15: Synthesis of Compound 202

[0337]

[0338] Synthesis of intermediate 202-1: The synthesis method is the same as that of intermediate 103-1, except that 1-bromo-4-chlorodibenzofuran is replaced with 2-(4-bromophenyl)-4-phenylquinazoline to obtain intermediate 202-1 (yield: 78%).

[0339] Synthesis of compound 202: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate J and intermediate 202-1 to obtain compound 202 (yield: 70%).

[0340] Mass spectrometry: C43H26N4S, theoretical value: 630.19, measured value: 630.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.27~7.41(3H, m), 7.44~7.58(5H, m), 7.58~7.73(5H, m), 7.75~7.83(3H, m), 7.84~7.88(1H, m), 7.94~7.98(5H, m), 8.11~8.18(2H, m), 8.43~8.47(1H, m), 8.49~8.53(1H, m).

[0341] Example 16: Synthesis of Compound 210

[0342]

[0343] Synthesis of compound 210: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate M and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 210 (yield: 79%).

[0344] Mass spectrometry: C47H33N5, theoretical value: 667.27, measured value: 667.30. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.81~1.83 (6H, s), 7.27~7.41 (3H, m), 7.44~7.53 (12H, m), 7.59~7.66 (1H, m), 7.76~7.80 (1H, m), 7.82~7.89 (2H, m), 7.91~7.96 (1H, d), 8.24~8.40 (6H, m), 8.95~8.97 (1H, d).

[0345] Example 17: Synthesis of Compound 235

[0346]

[0347] Synthesis of compound 235: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate N and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 235 (yield: 74%).

[0348] Mass spectrometry: C38H22N4O2, theoretical value: 566.17, measured value: 566.20. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.37~7.46 (7H, m), 7.53~7.68 (6H, m), 7.74~7.79 (1H, m), 8.07~8.13 (2H, m), 8.24~8.32 (4H, m), 8.40~8.45 (1H, m), 8.62~8.64 (1H, d).

[0349] Example 18: Synthesis of Compound 275

[0350]

[0351] Synthesis of compound 275: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate O and 2-chloro-4-phenylquinazoline to obtain compound 275 (yield: 76%).

[0352] Mass spectrometry: C37H21N3OS, theoretical value: 555.14, measured value: 555.15. 1H-NMR (400MHz, CDCl3) (ppm) δ=7.43~7.56 (2H, m), 7.58~7.71 (8H, m), 7.72~7.81 (3H, m), 7.93~7.98 (2H, m), 8.08~8.19 (4H, m), 8.46~8.51 (1H, m), 8.56~8.58 (1H, d).

[0353] Example 19: Synthesis of Compound 286

[0354]

[0355] Synthesis of compound 286: The synthesis method was the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine were replaced with intermediate P and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 286 (yield: 76%).

[0356] Mass spectrometry: C41H28N4O, theoretical value: 592.23, measured value: 592.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.80~1.84 (6H, s), 7.32~7.36 (1H, m), 7.44~7.53 (7H, m), 7.60~7.67 (3H, m), 7.77~7.79 (1H, m), 7.89~7.95 (2H, m), 8.05~8.07 (1H, m), 8.16~8.20 (2H, m), 8.34~8.38 (4H, m), 8.86~8.88 (1H, d).

[0357] Example 20: Synthesis of Compound 336

[0358]

[0359] Synthesis of compound 336: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate Q and 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)phenyl)-1,3,5-triazine to obtain compound 336 (yield: 74%).

[0360] Mass spectrometry: C41H28N4S, theoretical value: 608.20, measured value: 608.19. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.80~1.84 (6H, s), 7.27~7.37 (2H, m), 7.43~7.57 (8H, m), 7.69~7.73 (1H, m), 7.81~7.89 (2H, m), 7.94~7.97 (4H, s), 8.21~8.26 (1H, m), 8.32~8.40 (4H, m).

[0361] Example 21: Synthesis of Compound 353

[0362]

[0363] Synthesis of compound 353: The synthesis method is the same as that of compound 3, except that intermediate A and 2-bromo-4,6-diphenyltriazine are replaced with intermediate R and 2-chloro-4,6-diphenyl-1,3,5-triazine to obtain compound 353 (yield: 71%).

[0364] Mass spectrometry: C47H33N5, theoretical value: 667.27, measured value: 667.25. 1H-NMR (400MHz, CDCl3) (ppm) δ=1.80~1.83 (6H, s), 7.29~7.33 (1H, m), 7.36~7.40 (2H, m), 7.45~7.53 (12H, m), 7.60~7.64 (1H, m), 7.76~7.79 (1H, m), 7.83~7.88 (2H, m), 7.91~7.93 (1H, d), 8.26~8.30 (2H, m), 8.33~8.38 (4H, m), 8.48~8.49 (1H, d).

[0365] Device Example 1

[0366] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (volume ratio 1:1), baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0367] The glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -4 Pa, HAT-CN is vacuum-deposited on the above-mentioned anolyte film as a hole injection layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm; then, a hole transport layer NPB is deposited at a deposition rate of 0.1 nm / s and a thickness of 60 nm; TCTA is vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a thickness of 10 nm.

[0368] The light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The light-emitting layer includes two host materials and a guest material. Using a multi-source co-evaporation method, the evaporation rate of host material compound 17 and host material RH-2 is adjusted to 0.1 nm / s, and the evaporation rate of guest material (piq)2Ir(acac) is set to 6% of the evaporation rate of the host material. The total evaporation film thickness is 30 nm.

[0369] A hole blocking layer TPBi is vacuum-deposited on top of the light-emitting layer at a deposition rate of 0.1 nm / s and a thickness of 5 nm. Then, an electron transport layer is deposited by using a multi-source co-evaporation method, adjusting the deposition rates of ET-1 and ET-2 to 0.1 nm / s, with a total film thickness of 30 nm.

[0370] A 1 nm thick LiF layer was vacuum-deposited on the electron transport layer (ETL) as the electron injection layer, and a 150 nm thick Al layer was used as the cathode of the device.

[0371] The molecular structures involved are as follows:

[0372]

[0373]

[0374] Device Examples 2-15

[0375] Organic electroluminescent devices for the device examples shown in Table 1 were prepared using a method similar to that used in Device Example 1, except that compound 17 and host material RH-2 in Device Example 1 were replaced with the compounds and their proportions shown in Table 1, respectively.

[0376] Device Comparison Examples 1-2

[0377] Organic electroluminescent devices for the device comparative examples shown in Table 1 were prepared using a method similar to that used in Device Example 1, except that compound 17 in Device Example 1 was replaced with the following compounds.

[0378]

[0379] Test Example 1

[0380] At a brightness of 2000 cd / m² 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in the device examples and device comparative examples were measured, and the results are shown in Table 1.

[0381] Table 1

[0382] Red light main material Drive voltage (V) Efficiency (cd / A) Device Example 1 Compound 17:RH-2 = 1:1 3.85 9.9 Device Example 2 Compound 54:RH-2 = 1:1 3.82 12.2 Device Example 3 Compound 117:RH-2 = 1:1 3.86 12.1 Device Example 4 Compound 133:RH-2 = 1:1 3.89 12.0 Device Example 5 Compound 178:RH-2 = 1:1 3.90 10.1 Device Example 6 Compound 202:RH-2 = 1:1 4.12 10.7 Device Example 7 Compound 275:RH-2 = 1:1 4.05 11.2 Device Example 8 Compound 54:RH-4 = 1:1 3.94 11.4 Device Example 9 Compound 32:RH-7 = 1:1 4.05 10.9 Device Example 10 Compound 54:RH-27 = 1:1 4.03 11.1 Device Example 11 Compound 54:RH-61 = 1:1 3.91 11.7 Device Example 12 Compound 54:RH-2 = 7:3 3.92 9.8 Device Example 13 Compound 54:RH-4 = 7:3 3.98 10.1 Device Example 14 Compound 275:RH-7 = 6:4 4.07 10.5 Device Example 15 Compound 54:RH-27 = 7:3 4.03 10.4 Device Comparison Example 1 ref-1:RH-2 = 1:1 4.53 8.1 Device Comparison Example 2 ref-2:RH-2 = 1:1 4.57 7.9

[0383] As can be seen from the experimental results shown in Table 1, when the compound of the present invention is used as the red light host material of the organic electroluminescent device, it has a lower driving voltage and higher luminous efficiency compared with the prior art.

[0384] Device Example 16

[0385] The glass plate coated with the ITO transparent conductive layer was ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment until all moisture was removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0386] The glass substrate with the anode was placed in a vacuum chamber and evacuated to a vacuum level of 1×10⁻⁶. -4Pa, HAT-CN is vacuum-deposited on the above-mentioned anodic layer as a hole injection layer at a deposition rate of 0.1 nm / s and a total film thickness of 5 nm; then, a hole transport layer NPB is deposited at a deposition rate of 0.1 nm / s and a thickness of 60 nm; TCTA is vacuum-deposited on the hole transport layer as an electron blocking layer at a deposition rate of 0.1 nm / s and a thickness of 10 nm.

[0387] The light-emitting layer of the device is vacuum-deposited on top of the hole transport layer. The light-emitting layer includes a host material and a guest material. Using a multi-source co-evaporation method, the evaporation rate of the host material BH is adjusted to 0.1 nm / s, and the evaporation rate of the guest material BD is set to 5% of the evaporation rate of the host material BH. The total evaporation film thickness is 30 nm.

[0388] The electron transport layer of the device was vacuum-deposited on top of the light-emitting layer. The deposition rate of compound 3 was 0.1 nm / s, and the total film thickness was 35 nm.

[0389] A 1 nm thick LiF layer was vacuum-deposited on the electron transport layer (ETL) as the electron injection layer, and a 150 nm thick Al layer was used as the cathode of the device.

[0390] The molecular structures involved are as follows:

[0391]

[0392] Device Examples 17-31

[0393] Organic light-emitting devices of the device examples shown in Table 2 were prepared using a method similar to that of device example 16, except that compound 3 in device example 16 was replaced with the corresponding compound in Table 2.

[0394] Device Comparison Examples 3-4

[0395] Organic electroluminescent devices for the device comparison examples shown in Table 2 were prepared using a method similar to that used in Device Example 16, except that compound 3 in Device Example 1 was replaced with ref-1 or ref-2.

[0396] Test Example 2

[0397] At 1000cd / m 2 Under certain brightness conditions, the driving voltage and current efficiency of the organic electroluminescent devices prepared in the device examples and device comparative examples were measured, and the results are shown in Table 2.

[0398] Table 2

[0399] Electron transport materials Drive voltage (V) Efficiency (cd / A) <![CDATA[Brightness (cd / m 2 )]]> Device Example 16 Compound 3 3.85 11.2 1000 Device Example 17 Compound 17 4.01 11.5 1000 Device Example 18 Compound 32 4.19 10.1 1000 Device Example 19 Compound 42 4.21 9.9 1000 Device Example 20 Compound 90 4.11 11.4 1000 Device Example 21 Compound 103 4.23 9.8 1000 Device Example 22 Compound 123 4.14 11.0 1000 Device Example 23 Compound 147 3.82 11.3 1000 Device Example 24 Compound 168 4.13 11.1 1000 Device Example 25 Compound 178 4.15 10.9 1000 Device Example 26 Compound 181 3.80 12.2 1000 Device Example 27 Compound 210 4.14 12.1 1000 Device Example 28 Compound 235 4.09 10.8 1000 Device Example 29 Compound 286 4.17 10.9 1000 Device Example 30 Compound 336 4.29 9.7 1000 Device Example 31 Compound 353 4.18 12.0 1000 Device Comparison Example 3 ref-1 4.48 8.4 1000 Device Comparison Example 4 ref-2 4.50 8.2 1000

[0400] As can be seen from the data in Table 2 above, when the compound of the present invention is used as the electron transport material in the organic electroluminescent device, the organic electroluminescent device of the present invention can achieve a lower driving voltage and significantly improve the luminous efficiency.

[0401] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A fused ring compound, characterized by, The compound has a structural formula shown in formula (I); Formula (I), Formula (II), In formula (I), Any one of the A position and the B position is connected to the structure shown in formula (II) through a L connecting group which is present or absent; the remaining one of the A position and the B position is connected to the aryl of C 6-20 , or no connecting group; X 21 is O, S or -C(R 21 )2-; X 22 , X 23 are each independently selected from O, S, -N(R 22 )-; R 21 is C 1-12 1-10 alkyl; R 22 is absent or R 22 is selected from C 6-20 6-20 aryl; X 11 、X 12 、X 13 、X 14 each independently is selected from N, -C(R 11 )-; R 11 is selected from H, C 6-20 aryl, a biphenyl group, a biheterocyclic group; or two R 11 together form a benzene ring structure; The L linking group is provided by any one of the aromatic structures of diphenylthiophene, diphenylfuran, 9,9-dimethylfluorene, C 6-20 .

2. The compound of claim 1, wherein, In formula (I), Any one of the A position and the B position is connected to the structure shown in formula (II) through a L connecting group which is present or absent; the remaining one of the A position and the B position is connected to the aryl of C 6-12 , or no connecting group; X 21 is O, S or -C(R 21 )2-; X 22 , X 23 each independently is selected from O, S, -N(R 22 )-; R 21 is C 1-10 1-6alkyl; R 22 is absent or R 22 is selected from C 6-12 6alkyl; aryl; heteroaryl; heterocyclyl; X 11 、X 12 、X 13 、X 14 each independently is selected from N, -C(R 11 )-; R 11 is selected from H, C 6-12 aryl, diphenylthiophenyl, diphenylfuranyl; or two R 11 together form a benzene ring structure; The L linking group is provided by any one of the aromatic structures of diphenylthiophene, diphenylfuran, 9,9-dimethylfluorene, C 6-12 .

3. The compound of claim 2, wherein, In formula (I), Any one of the A position and the B position is connected with a structure shown in formula (I1) through a L connecting group which is present or absent; the remaining one of the A position and the B position is connected with a phenyl or naphthyl group, or no connecting group; X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-8 Alkyl group; R 22 Does not exist, or R 22 Selected from phenyl, biphenyl, and naphthyl; X 11 、X 12 、X 13 、X 14 each independently selected from N, -C(R 11 )-; R 11 is selected from H, phenyl, biphenyl, naphthyl, dibenzothiophenyl, dibenzofuranyl; or two R 11 together form a benzene ring structure; The L connecting group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, naphthalene.

4. The compound according to any one of claims 1-3, wherein, The compound of the structure shown in formula (I) is selected from any one of the following: 。 5. The compound according to any one of claims 1-3, wherein, In formula (I), The A position is connected with a structure shown in formula (I1) through a L connecting group which is present or absent, and the B position is connected with a phenyl or naphthyl group; X 21 is O, S or -C(R 21 )2-; X 22 , X 23 are each independently selected from O, S, -N(R 22 )-; R 21 is C 1-8 1-6alkyl; R 22 is absent or R 22 is selected from phenyl, biphenyl, naphthyl; X 11 , X 12 , X 13 , X 14 are each independently selected from N, -C(R 11 )-; R 11 is selected from H, phenyl, biphenyl, naphthyl, dibenzothiophenyl, dibenzofuranyl; or two R 11 together form a benzene ring structure; The L connecting group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, naphthalene.

6. The compound of claim 5, wherein, The compound of the structure shown in formula (I) is selected from any one of the following: 。 7. The compound according to any one of claims 1-3, wherein, In formula (I), The B position is connected with a structure shown in formula (I1) through a L connecting group which is present or absent, and the A position is no connecting group; X 21 For O, S or -C(R) 21 )2-;X 22 X 23 Each is independently selected from O, S, -N(R) 22 )-;R 21 C 1-8 Alkyl group; R 22 Does not exist, or R 22 Selected from phenyl, biphenyl, and naphthyl; X 11 、X 12 、X 13 、X 14 each independently is selected from N, -C(R 11 )-; R 11 is selected from H, phenyl, biphenyl, naphthyl, dibenzothiophenyl, dibenzofuranyl; or two R 11 together form a benzene ring structure; The L connecting group is provided by any one of dibenzothiophene, dibenzofuran, 9,9-dimethylfluorene, benzene, biphenyl, naphthalene.

8. The compound of claim 7, wherein, The compound of the structure shown in formula (I) is selected from any one of the following: 。 9. Use of the fused ring compound according to any one of claims 1 to 8 in an organic electroluminescent device.

10. An organic electroluminescent device comprising one or two or more condensed ring compounds of any one of claims 1 to 8, characterized in that The fused ring compound is present in at least one of the electron transport layer and the light-emitting layer of the organic electroluminescent device.

11. The organic electroluminescent device according to claim 10, wherein The fused ring compound is present in the light-emitting layer of the organic electroluminescent device.

12. The organic electroluminescent device according to claim 10, wherein The fused ring compound is present in the electron transport layer of the organic electroluminescent device.

13. The organic electroluminescent device according to claim 10, wherein The fused ring compound is present in the light-emitting layer of the organic electroluminescent device, and the light-emitting layer further contains a biscarbazole compound, and the molar ratio of the content of the fused ring compound to the content of the biscarbazole compound is 1:0.42-1.0; The double carbazole compound contains at least two groups provided by carbazole compounds, and the carbazole compound contains or does not contain R h1 substituent; R h1 The substituent is selected from at least one of phenyl, biphenyl, naphthyl, dibenzofuranyl, dibenzothiophenyl; optionally, the groups provided by any two adjacent carbazole compounds contain L h linking group; the L h The linking group is provided by at least one compound selected from benzene, biphenyl, terphenyl, dibenzofuran, dibenzothiophene; or, The biscarbazole compound is an A1 group, which is provided by a fused-ring compound containing five ring structures, wherein the five ring structures in the A1 group are sequentially bridged benzene ring, pyrrole ring, benzene ring, pyrrole ring, and benzene ring; and the A1 group may or may not contain R. h2 Substituents; R h2 The substituent is selected from at least one of phenyl, biphenyl, naphthyl, dibenzofuranyl, and dibenzothiopheneyl.

14. The organic electroluminescent device according to claim 13, wherein The biscarbazole compound is selected from any one of the following: 。 15. The organic electroluminescent device according to any one of claims 10 to 14, wherein The organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode which are sequentially stacked.

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