Organic electroluminescent compound and application thereof

Abstract

The invention relates to the technical field of display, in particular to an organic electroluminescent compound and application thereof. The organic electroluminescent compound provided by the invention has a structure shown as follows: # imgabs0 #, so that an organic electroluminescent device containing the organic electroluminescent compound has relatively low driving voltage, relatively high luminous efficiency and relatively long service life.

Description

Technical Field

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

[0002] Organic electroluminescent devices such as organic electroluminescent diodes (OLEDs) convert electrical energy into light by applying power to organic electroluminescent materials, and generally include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc., and the materials used in the organic layer are generally divided into hole injection materials, hole transport materials, hole auxiliary materials, luminescent auxiliary materials, electron blocking materials, luminescent materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. according to their functions. In an organic electroluminescent device, the luminescence mechanism is: under the drive of an external electric field, electrons and holes are injected into the organic electron transport layer and the hole transport layer by the cathode and the anode, respectively, and excitons are compounded in the organic luminescent layer, and the excitons radiatively transition back to the ground state and emit light.

[0003] At present, the existing organic electroluminescent materials have poor structural stability, poor matching between the HOMO and LUMO energy levels of the existing organic electroluminescent materials and the adjacent energy levels, and unbalanced carrier mobility. As a result, the organic electroluminescent devices containing the organic electroluminescent materials have high driving voltage, low luminous efficiency and short life, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0004] The purpose of the present invention is to overcome the problems of poor structural stability of existing organic electroluminescent materials, poor matching between HOMO and LUMO energy levels and adjacent energy levels, and unbalanced carrier mobility, which result in high driving voltage, low luminous efficiency and short life of organic electroluminescent devices containing the organic electroluminescent materials, and further provide an organic electroluminescent compound and its application.

[0005] Definitions of substituent terms in this invention:

[0006] As used herein, the term "halogen" may include fluorine, chlorine, bromine or iodine.

[0007] As used in the present invention, the term "C1-C30 alkyl" refers to a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 30 carbon atoms, examples of which include but are not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl.

[0008] As used in the present invention, the term "C3-C30 cycloalkyl" refers to a group derived from a monocyclic hydrocarbon or a polycyclic hydrocarbon having 1 to 30 ring main chain carbon atoms, and the cycloalkane may include cyclopropyl, cyclobutyl, adamantyl, and the like.

[0009] In the present invention, aryl and arylene groups include monocyclic, polycyclic or condensed-ring aromatic groups, the rings may be interrupted by short non-aromatic units, and may contain spiro structures. Aryl groups include but are not limited to phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc., and arylene groups include but are not limited to phenylene, biphenylene, terphenylene, naphthyl, phenanthryl, anthracenyl, fluorenyl, spirobifluorenyl, etc.

[0010] In the present invention, heteroaryl and heteroarylide include monocyclic, polycyclic or condensed ring heteroaryl, and the rings may be interrupted by short non-aromatic units, and the heteroatoms include nitrogen, oxygen and sulfur. Heteroaryl includes, but is not limited to, furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzo thiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, and derivatives thereof; heteroarylene includes but is not limited to furanyl, phenylene thio, pyrroleyl yl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, benzofuranyl, benzothiophenylene, isobenzofuranyl, dibenzofuranyl, dibenzothiophenylene, benzimidazolyl, oxazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, acridinyl, and derivatives thereof.

[0011] As used in the present invention, the term "substituted" refers to a hydrogen atom in a compound being replaced by another substituent. The position is not limited to a specific position, as long as the hydrogen at the position can be replaced by a substituent. When two or more substituents are present, the two or more substituents may be the same or different.

[0012] As used herein, unless otherwise specified, hydrogen atoms include protium, deuterium and tritium.

[0013] In the present invention, the range of the number of carbon atoms is defined in the definition of the group, and the number of carbon atoms is any integer within the defined range. For example, C6-C30 aromatic group, the number of carbon atoms representing the aromatic group can be any integer within the range of 6-60, such as 6, 8, 10, 13, 15, 17, 20, 22, 25 or 30, etc.

[0014] In the present invention, Indicates a connection key.

[0015] The scheme adopted by the present invention is as follows:

[0016] The present invention provides an organic electroluminescent compound having the structure of the following formula 1:

[0017]

[0018] Among them, X 1 , X 2 Each independently selected from O, S, Se;

[0019] L is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0020] Ar 1 ,Ar 2 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl;

[0021] The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group and substituted C3-C60 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C12 cycloalkyl group, C6-C30 aryl group and C3-C30 heteroaryl group.

[0022] Preferably, L is selected from a linking bond, a substituted or unsubstituted C6-C12 arylene group, a substituted or unsubstituted C3-C12 heteroarylene group;

[0023] Ar 1 ,Ar 2Selected from hydrogen, deuterium, cyano, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl;

[0024] The substituents in the substituted C6-C12 arylene group, substituted C3-C12 heteroarylene group, substituted C6-C25 aryl group and substituted C3-C25 heteroaryl group are each independently selected from one or a combination of at least two of the C1-C6 alkyl group, the C3-C12 cycloalkyl group, the C6-C25 aryl group and the C3-C25 heteroaryl group.

[0025] Preferably, L is selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group;

[0026] Ar 1 ,Ar 2 A group selected from hydrogen, deuterium, halogen, substituted or unsubstituted;

[0027] Wherein the A group is selected from one of the following groups:

[0028] Phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, phenyl, terphenyl, triphenylene, fluoranthene, quaterphenyl, phenylnaphthyl, naphthylphenyl, phenylnaphthyl, binaphthyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, pyrimidinyl, pyrimidinylphenyl, quinolyl, pyrazinyl, phenylpyridinyl, spirobifluorenyl, phenylmethylfluorenyl, dinaphthofuranyl, benzofurano[3,2-b]benzofuranyl, benzo[B]benzo[4,5]thieno[2,3-d]thienyl, benzo[4,5]thieno[3,2-b]benzofuranyl, spiro[fluorene-9,9'-xanthenyl]yl, benzopyridofuranyl, dibenzofuranyl, dibenzothienyl, dibenzoselenophene, and benzonaphthofuranyl;

[0029] The substituents in the substituted phenylene, substituted naphthylene, substituted biphenylene, and substituted A groups are selected from one or a combination of two of C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl, and C3-C12 heteroaryl;

[0030] Preferably, L is selected from a linker, a phenylene group, and a naphthylene group;

[0031] Preferably, Ar 1 ,Ar 2 Selected from phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, yl, terphenyl, quaterphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, phenylnaphthyl, binaphthyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, pyrimidinyl, pyrimidinylphenyl, quinolyl, pyrazinyl, phenylpyridyl, spiro[fluorene-9,9'-xanthenyl]yl, dinaphthofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl.

[0032] Preferably, in Formula 1:

[0033] Denoted as formula 1-a;

[0034] Formula 1-a is selected from one of the following structures:

[0035]

[0036]

[0037]

[0038] Preferably, in Formula 1:

[0039] Denoted as formula 1-f;

[0040] Formula 1-f is selected from one of the following structures:

[0041]

[0042]

[0043]

[0044]

[0045] Preferably, formula 1-a is selected from one of the following structures:

[0046]

[0047] Preferably, the organic electroluminescent compound is selected from one of Compounds 1 to 1914 in the following table:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The present invention also provides an organic electroluminescent material, comprising the organic electroluminescent compound having the structure of Formula 1.

[0072] Preferably, the organic electroluminescent material further comprises an electroluminescent compound having a structure of Formula 2, and the structure of Formula 2 is as follows:

[0073]

[0074] Among them, L 1 is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 8 -Ar 9Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group;

[0075] The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group and substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group and C3-C30 heteroaryl group.

[0076] Preferably, Ar 8 -Ar 9 are each independently selected from hydrogen, deuterium, and substituted or unsubstituted B groups;

[0077] Wherein group B is selected from one of the following groups:

[0078] Phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthiobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, benzocarbazolyl, benzocarbazolyl, dibenzocarbazolyl;

[0079] The substituent in the substituted B group is selected from one or a combination of two of a C1-C6 alkyl group, a C3-C30 cycloalkyl group, a C5-C12 aryl group, and a C3-C12 heteroaryl group;

[0080] Preferably, Ar 8 -Ar 9 each independently selected from phenyl, naphthyl, biphenyl, phenanthryl, anthracenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, phenylnaphthyl, naphthobenzofuranyl, dibenzothienyl, naphthylphenyl, naphththobenzofuranylphenyl;

[0081] Preferably, L 1 A connecting bond, a substituted or unsubstituted C6-C12 arylene group; the substituent of the substituted C6-C12 arylene group is selected from one or a combination of two of a C1-C6 alkyl group, a C3-C30 cycloalkyl group, a C5-C12 aryl group, and a C3-C12 heteroaryl group;

[0082] Preferably, L 1 Select from the connection keys.

[0083] Preferably, the structure of the electroluminescent compound having the structure of Formula 2 is selected from one of the following structures:

[0084]

[0085]

[0086] Among them, Ar 8 ,Ar 9 The definition of is the same as above.

[0087] Preferably, the structure of the electroluminescent compound having the structure of Formula 2 is selected from one of the following structures:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] Preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 1:99-99:1;

[0099] Preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 10:90-90:10;

[0100] More preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 30:70-70:30;

[0101] Further preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 40:60-60:40;

[0102] More preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 50:50.

[0103] The present invention also provides an organic electroluminescent device, which comprises a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises the organic electroluminescent compound or the organic electroluminescent material described above.

[0104] Preferably, the organic layer comprises an electron transport layer, and the electron transport layer comprises the above-mentioned organic electroluminescent compound or the above-mentioned organic electroluminescent material.

[0105] Preferably, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the above-mentioned organic electroluminescent compound or the above-mentioned organic electroluminescent material.

[0106] Optionally, the material of the light-emitting layer includes a host material and a guest material; the host material includes the above-mentioned organic electroluminescent compound.

[0107] In an embodiment of an organic electroluminescent device of the present invention, the organic layer is composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer stacked in sequence, and the organic electroluminescent device also includes a substrate, which is located on the surface of the anode facing away from the cathode.

[0108] In the present invention, the anode preferably comprises a material having a high work function, such as indium tin oxide (ITO) or indium zinc oxide (IZO).

[0109] The hole transport material is a material having high hole mobility, which can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer.

[0110] In the present invention, the light-emitting layer comprises a host material and a dopant, the host comprises a plurality of host materials, the plurality of host materials comprises a first host material and a second host material, the first host material may be composed of a single organic electroluminescent compound having a structure of Formula 1 or at least one compound of the organic electroluminescent compound having a structure of Formula 1, and may further comprise conventional materials in organic electroluminescent materials, the second host material may be composed of an organic electroluminescent compound having a structure of Formula 2 or at least one compound of the organic electroluminescent compound having a structure of Formula 2, and may further comprise conventional materials in organic electroluminescent materials; the mass ratio of the organic electroluminescent compound having a structure of Formula 1 to the organic electroluminescent compound having a structure of Formula 2 is about 1:99 to 99:1, preferably 10:90 to 90:10, more preferably 30:70 to 70:30, even more preferably 40:60 to 60:40, and still more preferably 50:50.

[0111] In the present invention, the light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the various host materials according to the present disclosure, the first host material and the second host material may be contained in one layer, or may be contained in different light emitting layers, respectively.

[0112] The dopant in the organic electroluminescent device of the present invention may be at least one phosphorescent dopant or fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present invention is not particularly limited and may be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), preferably selected from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.

[0113] In the present invention, the hole blocking layer material may be a compound with hole blocking function known in the prior art, for example, phenanthroline derivatives such as bathocuproine (BCP), oxazole derivatives, triazole derivatives, triazine derivatives, etc., but is not limited thereto.

[0114] In the present invention, the electron transport layer can promote electron transport, and compounds with electron transport function known in the prior art can be used, for example, Al complex of 8-hydroxyquinoline; complex containing Alq3; organic free radical compound; hydroxyflavone-metal complex, etc.

[0115] In the present invention, the electron injection layer can promote electron injection, has the ability to transport electrons, and prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer. The electron injection materials used in the present invention include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenyl methane or anthrone, as well as their derivatives, metal complexes or nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0116] In the present invention, the cathode is generally preferably made of a material with a small work function so that electrons can be smoothly injected into the organic material layer, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an alloy thereof.

[0117] The present invention also provides the use of the above-mentioned organic electroluminescent device in optical fiber equipment, lighting equipment, electronic photographic photosensitive body equipment, photoelectric converter, organic solar cell, switch element equipment, organic light-emitting field effect transistor, image sensor or dye laser.

[0118] In the present invention, the synthesis path of the organic electroluminescent compound comprises the following steps:

[0119] 1. Synthesis of intermediate nA

[0120]

[0121] 2. Synthesis of organic electroluminescent compounds

[0122]

[0123] Beneficial effects of the present invention:

[0124] The organic electroluminescent compound provided by the present invention is based on the structure of Formula 1, and further defines the structure of the substituent, so that the energy level matching degree of the organic electroluminescent compound is improved. When the organic electroluminescent material provided by the present invention is used as a hole transport material or a host material of an organic electroluminescent device, it has the characteristic of high carrier mobility, so that the luminous efficiency of the device is improved; the HOMO and LUMO energy levels of the organic electroluminescent compound have a high matching degree with the adjacent energy levels, so that the organic electroluminescent compound obtains higher stability and the carrier mobility is more balanced, and thus the organic electroluminescent device containing the organic electroluminescent compound has lower driving voltage, higher luminous efficiency and longer life.

[0125] Furthermore, the present invention provides an organic electroluminescent material, which also includes an electroluminescent compound with a structure of Formula 2. The electroluminescent compound with a structure of Formula 1 cooperates with the electroluminescent compound with a structure of Formula 2, which is beneficial for matching the HOMO and LUMO energy levels with adjacent energy levels, so that the organic electroluminescent material obtains higher stability and more balanced carrier mobility, thereby making the organic electroluminescent device containing the material have a better lifespan, and also has a lower driving voltage and higher efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0126] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0127] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0128] 1-substrate; 2-anode; 3-hole injection layer; 4-hole transport layer; 5-light-emitting layer; 6-electron transport layer; 7-electron injection layer; 8-cathode. DETAILED DESCRIPTION

[0129] The following examples are provided for a better understanding of the present invention, but are not intended to limit the best mode of implementation, nor to limit the content and protection scope of the present invention. Any product identical or similar to the present invention obtained by anyone under the inspiration of the present invention or by combining the features of the present invention with other prior arts shall fall within the protection scope of the present invention.

[0130] If no specific experimental steps or conditions are specified in the examples, the conventional experimental steps or conditions described in the literature in the field can be used. If no manufacturer is specified for the reagents or instruments used, they are all conventional reagent products that can be obtained commercially.

[0131] The term "organic electroluminescent material" in the present disclosure means a material that can be used in an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (containing a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0132] The term "multiple organic electroluminescent materials" in the present disclosure means one or more organic electroluminescent materials comprising a combination of at least two compounds, which may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained in an organic electroluminescent device before (e.g., before vapor deposition) and a material contained in an organic electroluminescent device after (e.g., after vapor deposition). For example, a plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be included in at least one of the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron blocking layer, a luminescent layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. At least two compounds may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0133] Some intermediate synthesis

[0134] Synthesis of intermediate 1-A:

[0135]

[0136] Synthesis of intermediate 1-A-1: Take a 100 ml three-necked round-bottom flask and put in a stirring bar. Under nitrogen protection, add the raw materials methoxymethyltriphenylphosphine chloride (1.8 mmol), potassium tert-butoxide (2.5 mmol), and tetrahydrofuran (10 mL) in sequence, cool to minus 15°C, stir for 30 minutes, and then slowly add a tetrahydrofuran solution of 1-Aa (i.e., 2-bromobenzofuran-3-carboxaldehyde) dropwise, react at minus 15°C for 30 minutes, then warm to room temperature and react for 2 hours. After the reaction is completed, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate 1-A-1 (yield 80%).

[0137] Synthesis of intermediate 1-A-2: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate 1-A-1 (1 mmol), bis(boronic acid ester) (1.1 mmol), 1,4-dioxane (10 mL), Pd(dppf)Cl2 (0.03 mmol), potassium acetate (2.5 mmol) in sequence, heat to 100 ° C, react for 5 hours, after the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate 1-A-2 (yield 83%).

[0138] Synthesis of intermediate 1-A-3: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate 1-A-2 (1 mmol), 1-Ab (1 mmol), i.e. 7-bromo-1-chlorodibenzo[b, d]furan, Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, heat to 90 ° C and react for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with ethyl acetate, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate 1-A-3 (yield 70%).

[0139] Synthesis of intermediate 1-A: Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add ferric chloride (0.1 mmol), calcium chloride (0.3 mmol), and 1,2-dichloroethane (10 mL) in sequence, heat to 90°C, and then slowly add a 1,2-dichloroethane solution of intermediate 1-A-3 (1 mmol) dropwise, and react at 90°C for 5 hours. After the reaction is completed, cool to room temperature, quench with saturated ammonium chloride aqueous solution, extract with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, use a rotary evaporator to remove the solvent, and separate the crude product by column chromatography (ethyl acetate: n-hexane = 1:50) to obtain intermediate 1-A (yield 46%).

[0140] Synthesis of intermediates 2-A to 54-A:

[0141] The preparation methods of intermediates 2-A to 54-A are as described in the preparation steps of intermediate 1-A, except that 1-Aa is selected from one of the following structures:

[0142]

[0143] 1-Ab is selected from one of the following structures:

[0144]

[0145] The specific structures of intermediates 2-A to 54-A are as follows:

[0146]

[0147]

[0148] Example 1

[0149] This embodiment provides an organic electroluminescent compound 8. The preparation method of the organic electroluminescent compound 8 specifically comprises the following steps:

[0150]

[0151] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate 1-A (1 mmol), 8-B, i.e. N-phenyldibenzo[b,d]furan-2-amine (0.9 mmol), Pd2(dba)3 (0.03 mmol), sodium tert-butoxide (2.5 mmol), and toluene (10 mL) in sequence. Heat to 110 ° C and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain an organic electroluminescent compound 8 (yield 49%).

[0152] Elemental analysis: C34 H 21 NO2 theoretical value: C, 85.87; H, 4.45; N, 2.95; O, 6.73; found value: C, 85.88; H, 4.46; N, 2.93; HRMS (ESI) m / z [M+H]+: theoretical value: 475.16; found value: 476.27.

[0153] Example 2

[0154] This example provides an organic electroluminescent compound 54. The preparation method of the organic electroluminescent compound 54 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 54-B is used to replace 8-B. The organic electroluminescent compound 54 (yield 53%) has the following reaction process:

[0155]

[0156] Elemental analysis: C 44 H 25 NO3 theoretical value: C, 85.84; H, 4.09; N, 2.28; O, 7.80; found value: C, 85.87; H, 4.10; N, 2.24; HRMS (ESI) m / z [M+H]+: theoretical value: 615.18; found value: 616.23.

[0157] Example 3

[0158] This example provides an organic electroluminescent compound 124. The preparation method of the organic electroluminescent compound 124 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 124-B is used instead of 8-B. The organic electroluminescent compound 124 (yield 48%) has the following reaction process:

[0159]

[0160] Elemental analysis: C 49 H 31 NO3 theoretical value: C, 86.32; H, 4.58; N, 2.05; O, 7.04; found value: C, 86.35; H, 4.60; N, 2.00; HRMS (ESI) m / z [M+H]+: theoretical value: 681.23; found value: 682.47.

[0161] Example 4

[0162] This example provides an organic electroluminescent compound 143. The preparation method of the organic electroluminescent compound 143 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 2-A is used instead of 1-A, and 10-B is used instead of 8-B. The organic electroluminescent compound 143 (yield 55%) has the following reaction process:

[0163]

[0164] Elemental analysis: C 40 H 23 NO3 theoretical value: C, 84.94; H, 4.10; N, 2.48; O, 8.49; found value: C, 84.97; H, 4.11; N, 2.44; HRMS (ESI) m / z [M+H]+: theoretical value: 565.17; found value: 566.13.

[0165] Example 5

[0166] This example provides an organic electroluminescent compound 446. The preparation method of the organic electroluminescent compound 446 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 4-A is used instead of 1-A, and 47-B is used instead of 8-B. The organic electroluminescent compound 446 (yield 55%) has the following reaction process:

[0167]

[0168] Elemental analysis: C 44 H 27 NO2 theoretical value: C, 87.83; H, 4.52; N, 2.33; O, 5.32; found value: C, 87.89; H, 4.51; N, 2.28; HRMS (ESI) m / z [M+H]+: theoretical value: 601.20; found value: 602.45.

[0169] Example 6

[0170] This embodiment provides an organic electroluminescent compound 530. The preparation method of the organic electroluminescent compound 530 specifically includes the following steps:

[0171]

[0172] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add intermediate 131-B (1 mmol), 4-A (0.9 mmol), Pd(dppf)Cl2 (0.03 mmol), potassium carbonate (2.5 mmol), 1,4-dioxane / water (10 mL / 2 mL) in sequence, raise the temperature to 90 ° C and react for 5 hours. After the reaction is completed, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product twice by recrystallization from o-dichlorobenzene to obtain organic electroluminescent compound 530 (yield 58%).

[0173] Elemental analysis: C40H 25 NO2 theoretical value: C, 87.09; H, 4.57; N, 2.54; O, 5.80; found value: C, 87.06; H, 4.55; N, 2.59; HRMS (ESI) m / z [M+H]+: theoretical value: 551.19; found value: 552.32.

[0174] Example 7

[0175] This embodiment provides an organic electroluminescent compound 845. The preparation method of the organic electroluminescent compound 845 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 8-A is used instead of 1-A, and 27-B is used instead of 8-B. The organic electroluminescent compound 845 (yield 62%) has the following reaction process:

[0176]

[0177] Elemental analysis: C 46 H 29 NOS theoretical value: C, 85.82; H, 4.54; N, 2.18; O, 2.49; S, 4.98; found value: C, 86.63; H, 6.27; N, 1.65; S, 5.46; HRMS (ESI) m / z [M+H] +: theoretical value: 643.20; found value: 644.22.

[0178] Example 8

[0179] This example provides an organic electroluminescent compound 1017. The preparation method of the organic electroluminescent compound 1017 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 13-A is used instead of 1-A, and 34-B is used instead of 8-B to obtain an organic electroluminescent compound 845 (yield 52%). The reaction of the preparation process is as follows:

[0180]

[0181] Elemental analysis: C 44H 27 NOS theoretical value: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19; found value: C, 85.53; H, 4.48; N, 2.22; S, 5.18; HRMS (ESI) m / z [M+H] +: theoretical value: 617.18; found value: 618.21.

[0182] Example 9

[0183] This example provides an organic electroluminescent compound 1231. The preparation method of the organic electroluminescent compound 1231 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 20-A is used instead of 1-A, and 18-B is used instead of 8-B. The organic electroluminescent compound 1231 (yield 59%) has the following reaction process:

[0184]

[0185] Elemental analysis: C 44 H 27 NS2 theoretical value: C, 83.38; H, 4.29; N, 2.21; S, 10.12; found value: C, 83.39; H, 4.28N, 2.20; S, 10.13; HRMS (ESI) m / z [M+H] +: theoretical value: 633.16; found value: 634.24.

[0186] Example 10

[0187] This example provides an organic electroluminescent compound 1331. The preparation method of the organic electroluminescent compound 1331 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 23-A is used instead of 1-A, and 67-B is used instead of 8-B. The organic electroluminescent compound 1331 (yield 62%) has the following reaction process:

[0188]

[0189] Elemental analysis: C 44 H 25 NOS2 theoretical value: C, 81.58; H, 3.89; N, 2.16; O, 2.47; S, 9.90; found value: C, 81.58; H, 3.91; N, 2.14; S, 9.89; HRMS (ESI) m / z [M+H] +: theoretical value: 647.14; found value: 648.47.

[0190] Embodiment 11

[0191] This example provides an organic electroluminescent compound 1403. The preparation method of the organic electroluminescent compound 1403 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 26-A is used instead of 1-A, and 57-B is used instead of 8-B. The organic electroluminescent compound 1403 (yield 58%) has the following reaction process:

[0192]

[0193] Elemental analysis: C 44 H 25 NO2Se theoretical value: C, 77.87; H, 3.71; N, 2.06; O, 4.71; Se, 11.63; measured value: C, 77.85; H, 3.71; N, 2.04Se, 11.67; HRMS (ESI) m / z [M+H]+: theoretical value: 679.11; measured value: 680.21.

[0194] Example 12

[0195] This example provides an organic electroluminescent compound 1426. The preparation method of the organic electroluminescent compound 1426 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 27-A is used instead of 1-A, and 108-B is used instead of 8-B. The organic electroluminescent compound 1426 (yield 64%) has the following reaction process:

[0196]

[0197] Elemental analysis: C 46 H 27 NO2Se theoretical value: C, 78.40; H, 3.86; N, 1.99; O, 4.54; Se, 11.20; measured value: C, 78.37; H, 3.89; N, 1.92; Se, 11.27; HRMS (ESI) m / z [M+H]+: theoretical value: 705.12; measured value: 706.23.

[0198] Embodiment 13

[0199] This example provides an organic electroluminescent compound 1524. The preparation method of the organic electroluminescent compound 1524 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 33-A is used instead of 1-A, and 9-B is used instead of 8-B. The organic electroluminescent compound 1524 (yield 65%) has the following reaction process:

[0200]

[0201] Elemental analysis: C 40 H23 NO2Se theoretical value: C, 76.43; H, 3.69; N, 2.23; O, 5.09; Se, 12.56; measured value: C, 76.42; H, 3.70; N, 2.20; Se, 12.59; HRMS (ESI) m / z [M+H]+: theoretical value: 629.09; measured value: 630.17.

[0202] Embodiment 14

[0203] This example provides an organic electroluminescent compound 1605. The preparation method of the organic electroluminescent compound 1605 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 37-A is used instead of 1-A, and 103-B is used instead of 8-B. The organic electroluminescent compound 1605 (yield 59%) has the following reaction process:

[0204]

[0205] Elemental analysis: C 46 H 28 Theoretical value of N2SSe: C, 76.76; H, 3.92; N, 3.89; S, 4.45; Se, 10.97; Found value: C, 76.79; H, 3.94; N, 3.82; S, 4.47; Se, 10.95; HRMS (ESI) m / z [M+H]+: Theoretical value: 720.11; Found value: 721.13.

[0206] Embodiment 15

[0207] This example provides an organic electroluminescent compound 1736. The preparation method of the organic electroluminescent compound 1736 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 45-A is used instead of 1-A, and 2-B is used instead of 8-B. The organic electroluminescent compound 1736 (yield 64%) has the following reaction process:

[0208]

[0209] Elemental analysis: C 38 H 23 NSSe theoretical value: C, 75.49; H, 3.83; N, 2.32; S, 5.30; Se, 13.06; found value: C, 75.67; H, 3.91; N, 2.29; S, 5.32; Se, 12.81; HRMS (ESI) m / z [M+H] +: theoretical value: 605.07; found value: 606.83.

[0210] Example 16

[0211] This embodiment provides an organic electroluminescent compound 1760. The preparation method of the organic electroluminescent compound 1760 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 46-A is used instead of 1-A, and 30-B is used instead of 8-B. The organic electroluminescent compound 1760 (yield 68%) has the following reaction process:

[0212]

[0213] Elemental analysis: C 43 H 29 NSSe theoretical value: C, 77.00; H, 4.36; N, 2.09; S, 4.78; Se, 11.77; found value: C, 77.43; H, 4.51; N, 1.74; S, 4.71; Se, 11.62; HRMS (ESI) m / z [M+H] +: theoretical value: 671.12; found value: 672.47.

[0214] Embodiment 17

[0215] This example provides an organic electroluminescent compound 1815. The preparation method of the organic electroluminescent compound 1815 is similar to the preparation method of the organic electroluminescent compound 8 in Example 1, except that 49-A is used instead of 1-A, and 32-B is used instead of 8-B. The organic electroluminescent compound 1815 (yield 61%) has the following reaction process:

[0216]

[0217] Elemental analysis: C 43 H 29 Theoretical value of NSe2: C, 71.97; H, 4.07; N, 1.95; Se, 22.01; Found value: C, 72.43; H, 4.32; N, 1.55; Se, 21.72; HRMS (ESI) m / z [M+H]+: Theoretical value: 719.06; Found value: 720.14.

[0218] Examples 18-26

[0219] The preparation methods of Examples 18-23 and 26 are similar to that of Example 1, and the preparation methods of Examples 24-25 are similar to that of Example 6. Specifically, the intermediates used in Examples 18-26 and the products obtained are shown in Table 1 below.

[0220]

[0221]

[0222] The characterization data of the products prepared in Examples 18-26 are shown in Table 2:

[0223] Table 2

[0224]

[0225] Embodiment 27

[0226] Synthesis of Compound M-17

[0227]

[0228] Take a 50 ml double-necked round-bottom flask and put it into a stirring bar and a reflux tube. After drying, fill it with nitrogen, add compound M17-A (19.8 mmol, CAS: 1884145-03-2), M17-B (20.75 mmol, CAS: 1883265-32-4), tetrakistriphenylphosphine palladium (0.396 mmol), potassium carbonate (39.6 mmol), 35 ml of toluene, 15 ml of ethanol and 15 ml of distilled water, and stir the mixture at 90 ° C for 8 hours. After the reaction is completed, the mixture is added dropwise to methanol, and the obtained solid is filtered, and the obtained solid is purified by column chromatography to obtain compound M-17 (8.5 g, yield: 75%).

[0229] Elemental analysis: C 41 H 25 N3O; theoretical value: C, 85.54; H, 4.38; N, 7.30; O, 2.78; found value: C, 85.52; H, 4.38; N, 7.32; HRMS (ESI) m / z (M+): theoretical value: 575.20; found value: 576.34.

[0230] Embodiment 28-48

[0231] Examples 28-48 provide methods for preparing compounds M-76, M-108, M-145, M-253, M-270, M-288, M-299, M-319, M-326, M-336, M-337, M-378, M-396, M-402, M-413, M-424, M-448, M-455, M-475, M-486, or M-487. The preparation methods of Examples 28-48 are similar to those of Example 27. Specifically, the intermediates used in Examples 28-48 and the products obtained are shown in Table 1 below.

[0232] Table 3

[0233]

[0234]

[0235]

[0236]

[0237] The characterization data of the products prepared in Examples 28-48 are shown in Table 4:

[0238] Table 4

[0239]

[0240]

[0241] Device Examples 1-5 and Device Comparative Example 1

[0242] The organic electroluminescent devices provided in device examples 1-5 and device comparative example 1 are as follows: Figure 1 As shown, it includes an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode 8 which are sequentially stacked on a substrate 1, and its device structure is: substrate + anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / light-emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0243] The materials for manufacturing the organic electroluminescent device are as follows:

[0244]

[0245] The preparation of the organic electroluminescent device comprises the following steps:

[0246] 1) Substrate cleaning:

[0247] The glass substrate coated with transparent ITO is ultrasonically treated in an aqueous cleaning agent (the composition and concentration of the aqueous cleaning agent: ethylene glycol solvent ≤ 10wt%, triethanolamine ≤ 1wt%), then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol (the volume ratio of acetone to ethanol is 1:1), baked in a clean environment until the moisture is completely removed, and then cleaned with ultraviolet light and ozone.

[0248] 2) Preparation of organic layer:

[0249] Transfer the ITO transparent substrate to the evaporation equipment and evacuate to 1×10 -6 Up to 2×10 -4Pa, 10nm hole injection layer (HIL) / 80nm hole transport layer (HTL) / 30nm light emitting layer (EML) / 30nm electron transport layer (ETL) / 1nm electron injection layer (EIL) / 90nm thick cathode (Al) were evaporated on the anode in sequence.

[0250] in:

[0251] The material of the hole injection layer (HIL) is a mixture of HATCN and HT, wherein the mass ratio of HATCN to HT is 3:97; the evaporation is carried out by co-evaporation;

[0252] Hole transport layer (HTL): vacuum evaporation of electron transport material by co-evaporation (specific materials are shown in Table 5);

[0253] Emission layer (EML): vacuum evaporation of luminescent materials by co-evaporation, wherein the luminescent materials include a host material and a guest material, wherein the host material is CBP, the guest material is (piq)2Ir(acac), and the mass ratio of the host material to the guest material is 95:5;

[0254] Electron transport layer (ETL): vacuum evaporation of electron transport material by co-evaporation (the mass ratio of ET and LiQ is 1);

[0255] The material of the electron injection layer (EIL) is LiQ;

[0256] The thickness and material of each layer are shown in Table 5.

[0257] Table 5

[0258]

[0259]

[0260] The embodiments in Table 5 refer to device embodiments, and the comparative examples refer to device comparative examples; taking the HTL layer in Example 1 as an example, "8" refers to compound 8, and the other numbers in the table correspond to the corresponding compounds.

[0261] Device Examples 6-29 and Device Comparative Examples 2 and 3

[0262] Device Examples 6-29 and Device Comparative Examples 2 and 3 adopt the structure of Device Example 1, except that the materials of the hole transport layer (HTL) and the light emitting layer (EML) are different. The thickness and materials of each layer are shown in Table 6.

[0263] Table 6

[0264]

[0265]

[0266]

[0267]

[0268] The embodiments in Table 6 refer to device embodiments, and the comparative examples refer to device comparative examples. Taking the EML layer in Example 6 as an example,

[0269] The “8” in “8:M-17:(piq)2Ir(acac)” refers to compound 8, and the other numbers in the table correspond to the corresponding compounds.

[0270] Test Case

[0271] The organic electroluminescent devices obtained from device examples 1 to 29 and device comparative examples 1 to 3 in the device examples were tested.

[0272] Instruments: The device's current, voltage, brightness, luminous spectrum and other characteristics are tested synchronously using a PR 650 spectrum scanning luminance meter and a Keithley K2400 digital source meter system;

[0273] Test conditions: Photoelectric properties Test conditions: Current density is 10mA / cm 2 .

[0274] Life test: current density is 50mA / cm 2 , record the time (in hours) when the device brightness drops to 95% of the original brightness. The device performance test results are shown in Table 7:

[0275] Table 7

[0276]

[0277]

[0278] The examples in Table 7 refer to device examples, and the comparative examples refer to device comparative examples.

[0279] Obviously, the above embodiments are merely examples for the purpose of clear explanation, and are not intended to limit the implementation methods. For those skilled in the art, other different forms of changes or modifications can be made based on the above description. It is not necessary and impossible to list all the implementation methods here. The obvious changes or modifications derived therefrom are still within the scope of protection of the invention.

Claims

1. An organic electroluminescent compound, characterized in that: It has the structure of Formula 1: Among them, X 1 , X 2 Each independently selected from O, S, Se; L is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 1 ,Ar 2 Selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C60 heteroaryl; The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group and substituted C3-C60 heteroaryl group are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl group, C3-C12 cycloalkyl group, C6-C30 aryl group and C3-C30 heteroaryl group.

2. The organic electroluminescent compound according to claim 1, characterized in that L is selected from a connecting bond, a substituted or unsubstituted C6-C12 arylene group, and a substituted or unsubstituted C3-C12 heteroarylene group; Ar 1 ,Ar 2 Selected from hydrogen, deuterium, cyano, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C25 heteroaryl; The substituents in the substituted C6-C12 arylene group, substituted C3-C12 heteroarylene group, substituted C6-C25 aryl group and substituted C3-C25 heteroaryl group are each independently selected from one or a combination of at least two of the C1-C6 alkyl group, the C3-C12 cycloalkyl group, the C6-C25 aryl group and the C3-C25 heteroaryl group.

3. The organic electroluminescent compound according to claim 1 or 2, characterized in that: L is selected from a linking bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group; Ar 1 ,Ar 2 A group selected from hydrogen, deuterium, halogen, substituted or unsubstituted; Wherein the A group is selected from one of the following groups: Phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, phenyl, terphenyl, triphenylene, fluoranthene, quaterphenyl, phenylnaphthyl, naphthylphenyl, phenylnaphthyl, binaphthyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, pyrimidinyl, pyrimidinylphenyl, quinolyl, pyrazinyl, phenylpyridinyl, spirobifluorenyl, phenylmethylfluorenyl, dinaphthofuranyl, benzofurano[3,2-b]benzofuranyl, benzo[B]benzo[4,5]thieno[2,3-d]thienyl, benzo[4,5]thieno[3,2-b]benzofuranyl, spiro[fluorene-9,9'-xanthenyl]yl, benzopyridofuranyl, dibenzofuranyl, dibenzothienyl, dibenzoselenophene, and benzonaphthofuranyl; The substituents in the substituted phenylene, substituted naphthylene, substituted biphenylene, and substituted A groups are selected from one or a combination of two of C1-C6 alkyl, C3-C30 cycloalkyl, C5-C12 aryl, and C3-C12 heteroaryl; Preferably, L is selected from a linker, a phenylene group, and a naphthylene group; Preferably, Ar 1 ,Ar 2 Selected from phenyl, naphthyl, biphenyl, anthracenyl, phenanthrenyl, yl, terphenyl, quaterphenyl, triphenylene, phenylnaphthyl, naphthylphenyl, phenylnaphthyl, binaphthyl, dimethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, pyrimidinyl, pyrimidinylphenyl, quinolyl, pyrazinyl, phenylpyridyl, spiro[fluorene-9,9'-xanthenyl]yl, dinaphthofuranyl, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl.

4. The organic electroluminescent compound according to any one of claims 1 to 3, characterized in that: In formula 1: Denoted as formula 1-a; Formula 1-a is selected from one of the following structures:

5. The organic electroluminescent compound according to any one of claims 1 to 4, characterized in that: In formula 1: Denoted as formula 1-f; Formula 1-f is selected from one of the following structures:

6. The organic electroluminescent compound according to any one of claims 1 to 5, characterized in that: Formula 1-a is selected from one of the following structures:

7. The organic electroluminescent compound according to any one of claims 1 to 6, characterized in that: The organic electroluminescent compound is selected from one of Compound 1 to Compound 1914 in the following table:

8. An organic electroluminescent material, characterized in that: The invention comprises the organic electroluminescent compound having the structure of formula 1 according to any one of claims 1 to 7.

9. The organic electroluminescent material according to claim 8, characterized in that: The organic electroluminescent material also includes an electroluminescent compound having a structure of Formula 2, and the structure of Formula 2 is as follows: Among them, L 1 is selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 8 -Ar 9 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group and substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl group, C3-C30 cycloalkyl group, C6-C30 aryl group and C3-C30 heteroaryl group.

10. The organic electroluminescent material according to claim 9, characterized in that: Ar 8 -Ar 9 are each independently selected from hydrogen, deuterium, and substituted or unsubstituted B groups; Wherein group B is selected from one of the following groups: Phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, anthracenyl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthiobenzofuranyl, benzothiophenyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, benzocarbazolyl, benzocarbazolyl, dibenzocarbazolyl; The substituent in the substituted B group is selected from one or a combination of two of a C1-C6 alkyl group, a C3-C30 cycloalkyl group, a C5-C12 aryl group, and a C3-C12 heteroaryl group; Preferably, Ar 8 -Ar 9 each independently selected from phenyl, naphthyl, biphenyl, phenanthryl, anthracenyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, phenylnaphthyl, naphthobenzofuranyl, dibenzothienyl, naphthylphenyl, naphththobenzofuranylphenyl; Preferably, L 1 A connecting bond, a substituted or unsubstituted C6-C12 arylene group; the substituent of the substituted C6-C12 arylene group is selected from one or a combination of two of a C1-C6 alkyl group, a C3-C30 cycloalkyl group, a C5-C12 aryl group, and a C3-C12 heteroaryl group; Preferably, L 1 Select from the connection keys.

11. The organic electroluminescent material according to claim 9 or 10, characterized in that: The structure of the electroluminescent compound having the structure of Formula 2 is selected from one of the following structures: Among them, Ar 8 ,Ar 9 The definition is the same as that of claim 10.

12. The organic electroluminescent material according to claims 9-11, characterized in that: The structure of the electroluminescent compound having the structure of Formula 2 is selected from one of the following structures:

13. The organic electroluminescent material according to claims 8 to 12, characterized in that: The mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 1:99-99:1; Preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 10:90-90:10; More preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 30:70-70:30; Further preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 40:60-60:40; More preferably, the mass ratio of the organic electroluminescent compound having the structure of Formula 1 to the organic electroluminescent compound having the structure of Formula 2 is 50:

50.

14. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises a cathode, an anode and an organic layer located between the cathode and the anode, wherein the organic layer comprises the organic electroluminescent compound according to any one of claims 1 to 7 or the organic electroluminescent material according to any one of claims 8 to 13.

15. The organic electroluminescent device according to claim 14, characterized in that: The organic layer comprises an electron transport layer, and the electron transport layer comprises the organic electroluminescent compound according to any one of claims 1 to 7 or the organic electroluminescent material according to any one of claims 8 to 13.

16. The organic electroluminescent device according to claim 14 or 15, characterized in that: The organic layer comprises a light-emitting layer, and the light-emitting layer comprises the organic electroluminescent compound according to any one of claims 1 to 7 or the organic electroluminescent material according to any one of claims 8 to 13.

17. Use of the organic electroluminescent device according to any one of claims 14 to 16 in optical fiber equipment, lighting equipment, electrophotographic photoreceptor equipment, photoelectric converters, organic solar cells, switching element equipment, organic light-emitting field effect transistors, image sensors or dye lasers.

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