Organic compound, application thereof and organic electroluminescent device

Abstract

The invention relates to the field of organic light-emitting devices, and discloses an organic compound, application thereof and an organic light-emitting device, and the organic compound has a structure as shown in a formula (I). When the organic compound is applied to the organic electroluminescent device, the performance of the device can be improved, the driving voltage is reduced, the luminous efficiency is improved, and the service life is prolonged. # imgabs0 #

Description

Technical Field

[0001] The invention relates to the field of organic electroluminescent devices, and in particular to an organic compound and application thereof, and an organic electroluminescent device. Background Art

[0002] The phenomenon of organic electroluminescence was first discovered by Pope et al. in 1963. They found that a single-layer crystal of anthracene could emit a faint blue light when driven by a voltage of more than 100 V. However, the driving voltage was high and the thickness of the single-crystalline anthracene was large, so it did not attract widespread attention.

[0003] It was not until 1987 that Dr. Qingyun Deng and others from Kodak reported that they had prepared a sandwich-type OLED device by vacuum thermal evaporation based on two organic semiconductor materials: 8-hydroxyquinoline aluminum with high fluorescence efficiency and good electron transport properties and aromatic diamine with good hole transport properties. At a driving voltage of less than 10V, the external quantum efficiency reached 1%, making organic electroluminescent materials and devices practical, which has greatly promoted the research on OLED materials and devices.

[0004] With the continuous development of OLED technology, the performance of OLED devices has also been widely concerned. During the research process, it was found that a device with high efficiency, long life and excellent performance requires excellent device materials and matching between the various layers of the device.

[0005] The principle of organic electroluminescence is to use organic matter to convert electrical energy into light energy. Common organic light-emitting elements generally include a structure of anode and cathode and an organic layer therebetween. The materials of the organic layer mainly include hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc.

[0006] At present, OLED or screen still has the defects of high driving voltage and low current efficiency. In order to improve these defects, on the one hand, it is necessary to find new materials with better performance and improve the performance of materials in each functional layer; on the other hand, the device structure and manufacturing process need to be further optimized.

[0007] Among them, electron transport materials play a vital role in the driving voltage and luminous efficiency of the device. In order to obtain high-performance electron transport materials, the material is required to have high electron mobility to improve the luminous efficiency and service life of the device.

[0008] Therefore, it is of great practical significance to develop high-performance electron transport materials to reduce the driving voltage of the device and improve the luminous efficiency of the device. Summary of the invention

[0009] The purpose of the present invention is to overcome the defects of the prior art, such as high driving voltage, low luminous efficiency and short service life.

[0010] In order to achieve the above object, the first aspect of the present invention provides an organic compound having a structure shown in formula (I):

[0011]

[0012] Wherein, in formula (I),

[0013] One of X1 and X2 is N, the other is N or CR 3 ; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group;

[0014] R1 is a substituent formed by the removal of any H atom from phenanthrene;

[0015] R2 is selected from substituted or unsubstituted C 3-8 cycloalkyl, substituted or unsubstituted C with or without A heteroatom 3-30 The A-type heteroatom is selected from at least one of N, O, and S; the substituents optionally present on R2 are each independently selected from halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, C 1-12 At least one of alkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano;

[0016] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

[0017] The second aspect of the present invention provides use of the organic compound described in the first aspect in an organic electroluminescent device.

[0018] The third aspect of the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device contains the organic compound described in the first aspect of the present invention.

[0019] The compounds of the present invention have suitable HOMO and LUMO energy levels, and both HOMO and LUMO energy levels are relatively deep. The deep HOMO energy level can block holes, and the deep LUMO energy level is conducive to the injection of electrons. At the same time, the compounds of the present invention can adjust the LUMO energy level in a small range, so that it has a high matching degree with the LUMO energy level of the light-emitting layer, thereby reducing the driving voltage of the device.

[0020] The compound of the present invention has high electron mobility, that is, strong electron transmission ability. The application of the compound of the present invention in an organic electroluminescent device can improve the luminous efficiency of the device.

[0021] The compound of the invention has a relatively high glass transition temperature, so that the thermal stability of the film is good, thereby increasing the service life of the device.

[0022] The organic compound of the present invention is applied to an organic electroluminescent device, and can improve the performance of the device, reduce the driving voltage, increase the luminous efficiency and prolong the service life. DETAILED DESCRIPTION

[0023] The endpoints and any values ​​of the ranges disclosed in this article 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 each range, the endpoint values ​​of each range and the individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed in this article.

[0024] In the present invention, unless otherwise specified, groups of the same type have similar explanations, and the present invention will not elaborate on them one by one.

[0025] In the absence of a particular description of the substitution position, the substituent of the present invention may be present at any position capable of being substituted in the structure, for example, "optionally present L1 and L2 are each independently selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted A connecting group provided by one or at least two structures of substituted quinoline, substituted or unsubstituted pyrimidine", wherein any two H atoms in benzene that can be removed can leave to become a connecting group, and L1 and L2 can also be a connecting group provided by at least two or at least three structures selected from the above structures. For example, L1 can be a connecting group provided by benzene and dibenzothiophene, and the benzene structure and the dibenzothiophene structure in the group each have an H atom at any site that can leave an H atom and leave, thereby connecting to the parent core structure.

[0026] In the present invention, among "substituted or unsubstituted benzene", the group provided for "phenyl-substituted benzene" as a connecting group is a different concept from the group provided for "biphenyl" as a connecting group. The group provided for "phenyl-substituted benzene" as a connecting group means that H atoms on any two sites on the benzene that can leave H atoms leave, and the benzene structure is connected to the parent core structure as a connecting group, and the benzene structure contains a substituted phenyl; while the group provided for "biphenyl" as a connecting group means that H atoms on each of the two benzene structures in the biphenyl leave at a site that can leave H atoms, so that the biphenyl structure is connected to the parent core structure as a connecting group.

[0027] C 1-12 The alkyl group represents a straight chain alkyl group or a branched chain alkyl group having a total number of carbon atoms of 1 to 12 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12).

[0028] Substituted or unsubstituted C with or without type A heteroatom 3-30 The aromatic group represents that the total number of carbon atoms in the group is 3-30, for example, it can be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, and the group can contain substituents and can also contain Class A heteroatoms, and Class A heteroatoms can be used as ring-forming atoms or as non-ring-forming atoms; including but not limited to benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, etc.

[0029] The aromatic group described in the present invention should be interpreted in a broad sense, and is a monocyclic planar conjugated polyene containing 4n+2 π electrons, or a group provided by the removal of an H atom from any site in a monocyclic planar conjugated polyene containing 4n+2 π electrons. It should be a group with aromaticity or homoaromaticity. Aromaticity should be interpreted in a broad sense, and the definition of homoaromaticity refers to the basic standard of homoaromaticity proposed by RF Childs et al. in 1995.

[0030] As mentioned above, the first aspect of the present invention provides an organic compound having a structure shown in formula (I):

[0031]

[0032] Wherein, in formula (I),

[0033] One of X1 and X2 is N, and the other is N or CH; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group;

[0034] R1 is a substituent formed by the removal of any H atom from phenanthrene;

[0035] R2 is selected from substituted or unsubstituted C 3-8 cycloalkyl, substituted or unsubstituted C with or without A heteroatom 3-30 The A-type heteroatom is selected from at least one of N, O, and S; the substituents optionally present on R2 are each independently selected from halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, C 1-12 At least one of alkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano;

[0036] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

[0037] Preferably, the substituted or unsubstituted C containing or not containing a type A heteroatom 3-30 The aromatic group is selected from at least one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline and substituted or unsubstituted carbazole.

[0038] According to a preferred embodiment, in formula (I),

[0039] One of X1 and X2 is N, the other is N or CR 3 ; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group;

[0040] R1 is a substituent formed by the removal of any H atom from phenanthrene;

[0041] R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, C 1-12 At least one of alkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano;

[0042] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

[0043] According to another preferred embodiment, in formula (I),

[0044] One of X1 and X2 is N, the other is N or CR 3 ; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group;

[0045] R1 is a substituent formed by the removal of any H atom from phenanthrene;

[0046] R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from C 1-12 Alkyl, C 3-8 At least one of cycloalkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl and dibenzothiophenyl;

[0047] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

[0048] According to a particularly preferred embodiment, the structure represented by formula (I) is selected from any one of Compound 1 to Compound 286.

[0049] According to another particularly preferred embodiment, in formula (I),

[0050] X1 and X2 are both N; X3 is CH;

[0051] R1 is a substituent formed by the removal of any H atom from phenanthrene;

[0052] R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from C 1-12 Alkyl, C 3-8 At least one of cycloalkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl and dibenzothiophenyl;

[0053] L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

[0054] More preferably, the structure represented by formula (I) of the present invention is selected from any one of Compound 1 to Compound 91 and Compound 93 to Compound 222.

[0055] The present invention has no particular limitation on the specific method for preparing the aforementioned organic compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention according to the specific structural formula provided by the present invention in combination with the known knowledge in the field of organic synthesis. In addition, several examples are exemplarily listed in the following text of the present invention to illustrate the preparation method of the organic compounds of the present invention. Those skilled in the art can also obtain the specific preparation method of all other organic compounds by replacing the types of raw materials according to the preparation method of the organic compounds in the following text of the present invention. The present invention no longer describes in detail the preparation methods of all organic compounds, and those skilled in the art should not be construed as limiting the present invention.

[0056] As mentioned above, the second aspect of the present invention provides the use of the organic compound described in the first aspect in an organic electroluminescent device.

[0057] As mentioned above, the third aspect of the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device contains the organic compound described in the first aspect of the present invention.

[0058] Preferably, the organic compound is present in the electron transport layer and / or the hole blocking layer of the organic electroluminescent device.

[0059] According to a particularly preferred embodiment, the organic compound is used as the electron transport material in the electron transport layer of the organic electroluminescent device.

[0060] According to a preferred specific embodiment, the organic electroluminescent device of the present invention comprises: a first electrode; a second electrode arranged opposite to the first electrode; and at least one organic material layer arranged between the first electrode and the second electrode, wherein at least one of the organic material layers contains the aforementioned organic compound of the present invention.

[0061] Preferably, the organic material layer of the organic electroluminescent device of the present specification may also form a multilayer structure of two or more organic material layers. The organic electroluminescent device of the present invention may include 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, and may include a charge generation layer disposed between the organic light emitting layers. However, the structure of the organic device is not limited thereto, and may include fewer or more organic layer materials.

[0062] According to a preferred embodiment of the present invention, the organic electroluminescent device of the present invention further comprises a first covering layer and / or a second covering layer, wherein the first covering layer is arranged on the outer surface of the anode, and the second covering layer is arranged on the outer surface of the cathode.

[0063] Preferably, the organic electroluminescent device of the present invention is coated with one or more layers by means of a sublimation method. In this case, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The organic compound provided by the present invention is applied by vapor deposition at an initial pressure of 1.5 Pa.

[0064] The organic electroluminescent device of the invention is preferably coated with one or more layers by an organic vapor deposition method or by means of carrier gas sublimation. -6 The material is applied at a pressure of 100 Pa to 100 Pa. A particular example of this method is an organic vapor deposition printing method, in which the compound provided by the present invention is directly applied through a nozzle and forms a device structure.

[0065] The organic electroluminescent device of the present invention is preferably formed into a single-layer or multi-layer structure by light-induced thermal imaging or thermal transfer.

[0066] The organic electroluminescent device of the present invention preferably prepares the organic compound of the present invention into a solution, and forms a layer or a plurality of layer structures by spin coating or by means of any printing method, such as screen printing, flexographic printing, inkjet printing, lithography, and more preferably inkjet printing. However, when multiple layers are made in this way, damage between layers is likely to occur, that is, when one layer is made, when another layer is made with a solution, the solvent in the solution will destroy the already formed layer, which is not conducive to device production. The organic compound provided by the present invention can be replaced by structural modification, so that the organic compound of the present invention undergoes cross-linking under heating or ultraviolet exposure, thereby maintaining a complete layer without being destroyed. The organic compound of the present invention can also be applied from a solution and fixed in the corresponding layer by subsequent cross-linking in a polymer network.

[0067] Preferably, the organic electroluminescent device according to the invention is produced by applying one or more layers from solution and by applying one or more layers by a sublimation process.

[0068] Preferably, when preparing the organic electroluminescent device of the present invention, the organic compound of the present invention or other compounds are first fully mixed, and then applied in the above manner to form one or more layers. More preferably, in a vacuum sublimation system, at a temperature of less than 10 -3 Pa, preferably less than 10 -6 The compounds are applied by vapor deposition at an initial pressure of 1.3 Pa to form one or more layers.

[0069] The present invention will be described in detail below by way of examples. In the following examples, unless otherwise specified, all the raw materials used are common commercial products. Unless otherwise specified, the room temperature described below means 25±1°C.

[0070] The present invention provides methods for preparing some of the compounds in the following specific structural formulas. The methods for preparing the remaining compounds can be carried out by referring to the methods provided below, which should not be construed as limiting the present invention by those skilled in the art.

[0071] Preparation Example 1

[0072]

[0073] Synthesis of intermediate 16-1: In a 500 ml three-necked flask, under nitrogen protection, add 2-amino-4,6-dichloropyrimidine (50 mmol), phenanthrene-9-ylboric acid (50 mmol), toluene (100 ml), dicyclohexyl (2',4',6'-triisopropyl-(1,1'-biphenyl)-2-yl)phosphonic acid (1.5 mmol), tris(dibenzylideneacetone)dipalladium (0.5 mmol), 100 ml of aqueous solution containing potassium dihydrogen phosphate (75 mmol), start stirring and heat to 90 ° C overnight reaction, after 25 hours, reduce the reaction temperature to 40 ° C, and then reduce to 0 ° C and maintain for 3 hours, filter to obtain a crude product, wash the crude product with water (200 ml), and then wash with ethanol (200 ml) to obtain a gray solid, and separate by silica gel column chromatography to obtain intermediate 16-1 (yield: 84.6%).

[0074] Synthesis of compound 16: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 16-1 and 4-(2,6-diphenylpyrimidin-4-yl)phenylboronic acid to obtain compound 16 (yield: 83.5%).

[0075] Mass spectrum: C40H27N5, theoretical value: 577.23, measured value: 577.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.98 ~ 2.01 (2H, s), 7.45 ~ 7.74 (10H, m), 7.84 ~ 7.86 (1H, s), 7.88 ~ 7.97 (3H, m), 8.15 ~ 8.20 (2H, m), 8.22 ~ 8.24 (1H, m), 8.28 ~ 8.39 (6H, m), 8.82 ~ 8.86 (1H, m), 9.06 ~ 9.10 (1H, m).

[0076] Preparation Example 2

[0077]

[0078] Synthesis of intermediate 32-1: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by 4-(phenanthrene-9-yl)phenylboronic acid to obtain intermediate 32-1 (yield: 82.5%).

[0079] Synthesis of compound 32: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 32-1 and 4-phenylnaphthalene-1-boronic acid to obtain compound 32 (yield: 84.3%).

[0080] Mass spectrum: C40H27N3, theoretical value: 549.22, measured value: 549.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.01 ~ 2.05 (2H, s), 7.22 ~ 7.28 (2H, m), 7.30 ~ 7.50 (5H, m), 7.54 ~ 7.58 (1H, s), 7.59 ~ 7.74 (4H, m), 7.76 ~ 7.82 (3H, m), 7.84 ~ 7.92 (2H, m), 8.15 ~ 8.18 (1H, d), 8.25 ~ 8.33 (3H, m), 8.82 ~ 8.86 (1H, m), 8.92 ~ 8.97 (1H, m), 8.99 ~ 9.10 (2H, m).

[0081] Preparation Example 3

[0082]

[0083] Synthesis of compound 34: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 32-1 and 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid to obtain compound 34 (yield: 81.3%).

[0084] Mass spectrum: C43H29N5, theoretical value: 615.24, measured value: 615.25. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 1.96 ~ 1.99 (2H, s), 7.22 ~ 7.32 (3H, m), 7.35 ~ 7.41 (2H, m), 7.44 ~ 7.57 (3H, m), 7.58 ~ 7.74 (5H, m), 7.79 ~ 7.99 (5H, m), 8.16 ~ 8.19 (1H, d), 8.24 ~ 8.33 (5H, m), 8.54 ~ 8.59 (1H, m), 8.82 ~ 8.86 (1H, m), 9.05 ~ 9.10 (1H, m).

[0085] Preparation Example 4

[0086]

[0087] Synthesis of intermediate 47-1: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by 6-(phenanthrene-9-yl)naphthalene-2-boronic acid to obtain intermediate 47-1 (yield: 80.5%).

[0088] Synthesis of compound 47: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 47-1 and dibenzofuran-4-boronic acid to obtain compound 47 (yield: 79.3%).

[0089] Mass spectrum: C40H25N3O, theoretical value: 563.20, measured value: 563.21. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.02 ~ 2.06 (2H, s), 7.27 ~ 7.45 (4H, m), 7.51 ~ 7.57 (2H, m), 7.59 ~ 7.77 (5H, m), 7.84 ~ 8.02 (6H, m), 8.05 ~ 8.11 (1H, m), 8.21 ~ 8.30 (2H, m), 8.50 ~ 8.54 (1H, m), 8.82 ~ 8.87 (1H, m), 9.06 ~ 9.11 (1H, m).

[0090] Preparation Example 5

[0091]

[0092] Synthesis of intermediate 69-1: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by 2-bromo-8-iododibenzofuran and phenanthrene-9-ylboronic acid to obtain intermediate 69-1 (yield: 81.2%).

[0093] Synthesis of intermediate 69-2: In a 200 ml three-necked flask, under nitrogen protection, intermediate 69-1 (14 mmol), 1,4-dioxane solvent (50 ml), diboron pinacol ester (14 mmol), potassium acetate (35 mmol) and [1,1'-bis(diphenylphosphino)ferrocene] palladium dichloride (0.14 mmol) were added in sequence, and the temperature was raised to reflux for reaction for 3 h. HPLC detected that the reaction of the raw materials was complete. After the reaction solution was cooled to room temperature, the reaction solution was decompressed and dried to obtain a crude product. The crude product was dissolved in toluene solvent, heated and stirred, and the temperature was raised to reflux. It was heated to a silica gel column for decolorization. The filtrate was decompressed and dried to a small amount of solvent. Ethanol (100 ml) was added for slurrying, and recrystallized from toluene / ethanol to obtain intermediate 69-2 (yield: 90.7%).

[0094] Synthesis of intermediate 69-3: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by intermediate 69-2 to obtain intermediate 69-3 (yield: 82.1%).

[0095] Synthesis of compound 69: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 69-3 and biphenyl-4-boronic acid to obtain compound 69 (yield: 79.7%).

[0096] Mass spectrum: C42H27N3O, theoretical value: 589.22, measured value: 589.21. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.94 ~ 1.97 (2H, s), 7.37 ~ 7.53 (3H, m), 7.59 ~ 7.78 (10H, m), 7.82 ~ 7.93 (4H, m), 8.23 ​​~ 8.33 (6H, m), 8.81 ~ 8.87 (1H, m), 9.06 ~ 9.11 (1H, m).

[0097] Preparation Example 6

[0098]

[0099] Synthesis of intermediate 78-1: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by 9-bromophenanthrene and 5-chloropyridine-2-boronic acid to obtain intermediate 78-1 (yield: 82.4%).

[0100] Synthesis of intermediate 78-2: The synthesis method is the same as that of intermediate 69-2, except that intermediate 69-1 is replaced by intermediate 78-1 to obtain intermediate 78-2 (yield: 90.4%).

[0101] Synthesis of intermediate 78-3: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by intermediate 78-2 to obtain intermediate 78-3 (yield: 81.1%).

[0102] Synthesis of compound 78: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 78-3 and biphenyl-4-boronic acid to obtain compound 78 (yield: 78.2%).

[0103] Mass spectrum: C35H24N4, theoretical value: 500.20, measured value: 500.21. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.98 ~ 2.02 (2H, s), 7.37 ~ 7.53 (3H, m), 7.59 ~ 7.78 (6H, m), 7.82 ~ 7.93 (3H, m), 8.16 ~ 8.33 (6H, m), 8.81 ~ 8.87 (2H, m), 9.06 ~ 9.12 (2H, m).

[0104] Preparation Example 7

[0105]

[0106] Synthesis of compound 152: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 32-1 and 4-(dibenzofuran-4-yl)phenylboronic acid to obtain compound 152 (yield: 82.3%).

[0107] Mass spectrum: C42H27N3O, theoretical value: 589.22, measured value: 589.21. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.97 ~ 2.01 (2H, s), 7.22 ~ 7.45 (7H, m), 7.52 ~ 7.57 (1H, m), 7.59 ~ 7.74 (4H, m), 7.84 ~ 7.86 (1H, s), 7.87 ~ 7.93 (1H, m), 7.95 ~ 8.11 (3H, m), 8.16 ~ 8.19 (1H, d), 8.24 ~ 8.33 (5H, m), 8.82 ~ 8.86 (1H, m), 9.05 ~ 9.10 (1H, m).

[0108] Preparation Example 8

[0109]

[0110] Synthesis of intermediate 193-1: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by 3-bromophenanthrene and 1,4-phenyldiboronic acid to obtain intermediate 193-1 (yield: 81.6%).

[0111] Synthesis of compound 193: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by intermediate 193-1 to obtain compound 193 (yield: 77.3%).

[0112] Mass spectrum: C44H29N3, theoretical value: 599.24, measured value: 599.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.95 ~ 1.99 (2H, s), 7.58 ~ 7.77 (8H, m), 7.82 ~ 7.93 (7H, m), 8.27 ~ 8.40 (8H, m), 8.82 ~ 8.88 (2H, m), 9.04 ~ 9.07 (2H, d).

[0113] Preparation Example 9

[0114]

[0115] Synthesis of intermediate 211-1: The synthesis method is the same as that of intermediate 16-1, except that phenylboronic acid is replaced by phenanthrene-4-boric acid to obtain intermediate 211-1 (yield: 81.9%).

[0116] Synthesis of compound 211: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 211-1 and 4-phenylnaphthalene-1-boronic acid to obtain compound 211 (yield: 81.4%).

[0117] Mass spectrum: C34H23N3, theoretical value: 473.19, measured value: 473.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.09 ~ 2.13 (2H, s), 7.30 ~ 7.50 (5H, m), 7.54 ~ 7.82 (7H, m), 7.87 ~ 7.93 (2H, m), 8.06 ~ 8.11 (1H, m), 8.18 ~ 8.27 (2H, m), 8.37 ~ 8.45 (1H, m), 8.93 ~ 9.05 (3H, m).

[0118] Preparation Example 10

[0119]

[0120] Synthesis of compound 243: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by 2-amino-4,6-dichlorotriazine and phenanthrene-9-ylboronic acid to obtain compound 243 (yield: 81.3%).

[0121] Mass spectrum: C31H20N4, theoretical value: 448.17, measured value: 448.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 2.50 ~ 2.53 (2H, s), 7.58 ~ 7.74 (8H, m), 7.87 ~ 7.93 (2H, m), 8.14 ~ 8.20 (2H, m), 8.37 ~ 8.40 (2H, d), 8.81 ~ 8.87 (2H, m), 9.05 ~ 9.11 (2H, m).

[0122] Preparation Example 11

[0123]

[0124] Synthesis of intermediate 265-1: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced with 4,6-dichloropyridine-2-amine and phenanthrene-3-boric acid to obtain intermediate 265-1 (yield: 79.2%).

[0125] Synthesis of compound 265: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 265-1 and 4-(naphthalen-2-yl)phenylboronic acid to obtain compound 265 (yield: 83.1%).

[0126] Mass spectrum: C35H24N2, theoretical value: 472.19, measured value: 472.20. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 0.99 ~ 1.02 (2H, s), 6.91 ~ 6.93 (1H, d), 7.23 ~ 7.27 (4H, s), 7.36 ~ 7.40 (1H, m), 7.54 ~ 7.69 (5H, m), 7.70 ~ 7.76 (2H, m), 7.81 ~ 7.83 (1H, m), 7.88 ~ 7.92 (1H, m), 7.97 ~ 8.11 (3H, m), 8.49 ~ 8.57 (2H, m), 8.83 ~ 8.87 (1H, m), 9.30 ~ 9.32 (1H, d).

[0127] Preparation Example 12

[0128]

[0129] Synthesis of intermediate 283-1: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by 4,6-dichloropyridine-2-amine and 4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenylboronic acid to obtain intermediate 283-1 (yield: 77.9%).

[0130] Synthesis of compound 283: The synthesis method is the same as that of intermediate 16-1, except that 2-amino-4,6-dichloropyrimidine and phenylboronic acid are replaced by intermediate 283-1 and phenanthrene-9-ylboronic acid to obtain compound 283 (yield: 82.3%).

[0131] Mass spectrum: C40H27N5, theoretical value: 577.23, measured value: 577.20. 1H-NMR (400MHz, CDCl3) (ppm) δ = 1.88 ~ 1.91 (2H, s), 6.86 ~ 6.89 (1H, d), 7.46 ~ 7.53 (6H, m), 7.59 ~ 7.74 (4H, m), 7.81 ~ 7.83 (1H, m), 7.87 ~ 7.99 (3H, m), 8.19 ~ 8.22 (1H, d), 8.25 ~ 8.29 (1H, m), 8.31 ~ 8.41 (4H, m), 8.66 ~ 8.72 (2H, m), 8.82 ~ 8.86 (1H, m), 9.05 ~ 9.11 (1H, m).

[0132] When the compound of the present invention is used in the electron transport layer, the structure of the organic electroluminescent device in device examples 1-1 to 1-12 and device comparative examples 1-1 to 1-2 is:

[0133] ITO / HTL:NPD-9(95:5%,10nm) / HTL(60nm) / GH:GD(90:10,30nm) / ETL:Liq(50:50,30nm) / Liq(2nm) / Al(100nm).

[0134] The molecular structure of each functional layer material is as follows:

[0135]

[0136] Device Example 1-1

[0137] 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 an acetone:ethanol mixed solvent (volume ratio 1:1), baked in a clean environment to completely remove water, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam.

[0138] The glass substrate with the anode is placed in a vacuum chamber and evacuated to 1×10 -5 Pa, vacuum evaporating a hole injection layer on the above-mentioned anode layer film, using a multi-source co-evaporation method to adjust the evaporation rate of the compound HTL to 0.1nm / s, the evaporation rate of the compound NPD-9 to 5%, and the total evaporation film thickness to 10nm; then evaporating the compound HTL as a hole transport layer, the evaporation rate is 0.1nm / s, and the thickness is 60nm; evaporating a light-emitting layer on the above-mentioned hole transport layer, the light-emitting layer includes a green light host material and a green light guest material, and using a multi-source co-evaporation method to adjust the green light The main material (GH) evaporation rate is 0.1nm / s, the green light guest material (GD) evaporation rate is set at 10%, and the total evaporation film thickness is 30nm; ETL (compound 16) is vacuum evaporated on the light-emitting layer as an electron transport layer, the evaporation rate is 0.1nm / s, the Liq evaporation rate is set at 50%, and the total evaporation film thickness is 30nm; Liq with a thickness of 2nm is vacuum evaporated on the electron transport layer as an electron injection layer, and an Al layer with a thickness of 100nm is used as the cathode of the device.

[0139] Device Examples 1-2 to 1-12

[0140] Organic light-emitting devices of device examples 1-2 to 1-12 were prepared by a method similar to that of device example 1-1, except that compound 16 in device example 1-1 was replaced by a compound shown in Table 1.

[0141] Device Comparative Examples 1-1 to 1-2

[0142] Organic electroluminescent devices of device comparison examples 1-1 to 1-2 were prepared by a method similar to that of device example 1-1, except that compound 16 in device example 1-1 was replaced by the compounds shown in Table 1.

[0143] At the same brightness of 10000cd / m 2 The driving voltage and current efficiency of the organic electroluminescent devices prepared in device examples 1-1 to 1-12 and device comparative examples 1-1 to 1-2 were measured. The results are shown in Table 1.

[0144] Table 1

[0145] Example Electron transport layer Driving voltage(V) Efficiency (cd / A) Emitting color Example 1-1 Compound 16 4.23 66.3 Green Light Example 1-2 Compound 32 4.05 67.3 Green Light Examples 1-3 Compound 34 4.17 67.0 Green Light Examples 1-4 Compound 47 4.14 67.1 Green Light Examples 1-5 Compound 69 4.19 66.4 Green Light Examples 1-6 Compound 78 4.11 66.9 Green Light Examples 1-7 Compound 152 4.02 67.5 Green Light Examples 1-8 Compound 193 4.22 66.7 Green Light Examples 1-9 Compound 211 4.28 65.7 Green Light Examples 1-10 Compound 243 4.25 65.9 Green Light Embodiment 1-11 Compound 265 4.29 65.4 Green Light Examples 1-12 Compound 283 4.27 66.1 Green Light Comparative Example 1-1 Ref1 4.61 57.2 Green Light Comparative Example 1-2 Ref2 4.52 56.8 Green Light

[0146] It can be seen from the experimental results shown in Table 1 that when the organic compound of the present invention is used as the electron transport material of the organic electroluminescent device, it has a significantly lower driving voltage and a higher luminous efficiency than Comparative Example 1-1 and Comparative Example 1-2.

[0147] The preferred embodiments of the present invention are described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, the technical solution of the present invention can be subjected to a variety of simple modifications, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be regarded as the contents disclosed by the present invention and belong to the protection scope of the present invention.

Claims

1. An organic compound, characterized in that The organic compound has a structure shown in formula (I): Wherein, in formula (I), One of X1 and X2 is N, the other is N or CR 3 ; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group; R1 is a substituent formed by the removal of any H atom from phenanthrene; R2 is selected from substituted or unsubstituted C 3-8 cycloalkyl, substituted or unsubstituted C with or without A heteroatom 3-30 The A-type heteroatom is selected from at least one of N, O, and S; the substituents optionally present on R2 are each independently selected from halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, C 1-12 At least one of alkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted quinazoline, substituted or unsubstituted spirobifluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

2. The organic compound according to claim 1, wherein In formula (I), One of X1 and X2 is N, the other is N or CR 3 ; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group; R1 is a substituent formed by the removal of any H atom from phenanthrene; R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from halogen, C 1-12 Alkyl, C 3-8 Cycloalkyl, C 1-12 At least one of alkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

3. The organic compound according to claim 2, wherein In formula (I), One of X1 and X2 is N, and the other is N or CH; X3 is N or CR 3 ; R 3 H, C 1-6 An alkyl or phenyl group; R1 is a substituent formed by the removal of any H atom from phenanthrene; R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from C 1-12 Alkyl, C 3-8 at least one of cycloalkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group.

4. The organic compound according to any one of claims 1 to 3, wherein The compound represented by formula (I) is selected from any one of the following structures:

5. The organic compound according to any one of claims 1 to 3, wherein In formula (I), X1 and X2 are both N; X3 is CH; R1 is a substituent formed by the removal of any H atom from phenanthrene; R2 is substituted or unsubstituted C 3-8 R2 is substituted or unsubstituted cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted furanyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted carbazole; the substituents optionally present on R2 are each independently selected from C 1-12 Alkyl, C 3-8 at least one of cycloalkyl, phenyl, biphenyl, pyridyl, naphthyl, dimethylfluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, amino, and cyano; L1 and L2 are each independently present or absent, and the optional L1 and L2 are each independently selected from a connecting group provided by one structure or at least two structures selected from substituted or unsubstituted benzene, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorene, substituted or unsubstituted carbazole, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted pyridine, substituted or unsubstituted quinoline, and substituted or unsubstituted pyrimidine; the optional substituents in L1 and L2 are selected from C 1-6 At least one of an alkyl group, a phenyl group, a cyano group, and a pyridyl group; Preferably, The compound represented by formula (I) is selected from any one of the following structures:

6. Use of the organic compound according to any one of claims 1 to 5 in an organic electroluminescent device.

7. An organic electroluminescent device, characterized in that: The organic electroluminescent device contains the organic compound according to any one of claims 1 to 5.

8. The organic electroluminescent device according to claim 7, wherein: The organic compound is present in the electron transport layer and / or the hole blocking layer of the organic electroluminescent device.

9. The organic electroluminescent device according to claim 8, wherein: The organic compound is used as an electron transport material in the electron transport layer of the organic electroluminescent device.

10. The organic electroluminescent device according to claim 8, wherein: The organic electroluminescent device is provided with a first electrode, a second electrode and an organic material layer located between the first electrode and the second electrode; the organic material layer includes a hole injection layer, a first hole transport layer, a first light-emitting layer and a first electron transport layer.

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