Organic light-emitting device

Abstract

The invention relates to the technical field of display, in particular to an organic light-emitting device. The invention provides an organic light-emitting device, which comprises a cathode and an anode which are oppositely arranged, and a light-emitting layer positioned between the cathode and the anode, and is characterized by further comprising a first organic layer positioned between the anode and the light-emitting layer, a second organic layer positioned between the anode and the light-emitting layer, and a third organic layer positioned between the cathode and the light-emitting layer, a second organic layer between the anode and the light emitting layer; and compounds with specific structures are selected as materials of the first organic layer and the second organic layer. The first organic layer and the second organic layer cooperate with each other, so that the driving voltage of the organic electroluminescent device can be effectively reduced, and the current efficiency of the organic electroluminescent device can be improved.

Description

Technical Field

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

[0002] Organic electroluminescent devices (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 an organic EL 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, and the like. The materials used in the organic layer may be 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, and the like depending on their functions. In an organic EL device, holes from the anode and electrons from the cathode are injected into the luminescent layer by applying a voltage, and excitons with high energy are generated by the recombination of holes and electrons, and light is emitted when the excitons re-transition to the ground state.

[0003] At present, the setting of functional layers and the selection of materials in existing organic electroluminescent devices easily lead to the problem of unbalanced carrier mobility in the device, resulting in high driving voltage and low current efficiency of the organic electroluminescent device, which seriously limits the application of organic electroluminescent devices. Summary of the invention

[0004] The purpose of the present invention is to overcome the problem that the arrangement of functional layers and the selection of materials in existing organic electroluminescent devices easily cause unbalanced carrier mobility in the device, resulting in high driving voltage and low current efficiency of the organic electroluminescent device, which seriously limits the application of the organic electroluminescent device.

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

[0015] The present invention provides an organic electroluminescent device, comprising: the organic electroluminescent device comprises a cathode and an anode arranged opposite to each other, a light-emitting layer located between the cathode and the anode, and further comprising:

[0016] a first organic layer located between the anode and the light-emitting layer;

[0017] a second organic layer located between the anode and the light-emitting layer;

[0018] Wherein, the first layer of material comprises a compound having the following structure:

[0019]

[0020] In formula (1), L 1 -L 3 Each is independently selected from a substituted or unsubstituted non-fused C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group;

[0021] Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, and a substituted or unsubstituted C3-C30 heteroaryl group;

[0022] The second organic layer material comprises a compound having the following structure:

[0023]

[0024] Among them, X 1 -X 14 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium;

[0025] Ar 4 ,Ar 5 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C60 arylamine group, and a substituted or unsubstituted C3-C60 heteroarylamine group;

[0026] The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C60 aromatic amine group and substituted C3-C60 heteroaromatic amine 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, C3-C30 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

[0027] Preferably, in the formula (1), L 1 -L 3 Each is independently selected from a substituted or unsubstituted non-fused C6-C30 arylene group;

[0028] Wherein, the substituent in the substituted non-fused C6-C30 arylene group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine;

[0029] Preferably, Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group;

[0030] Wherein, the substituents in the substituted C6-C60 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine;

[0031] Preferably, L 1 -L 3 Each independently selected from phenylene, biphenylene;

[0032] Ar 1 -Ar 3 Each is independently selected from substituted or unsubstituted C6-C18 aryl, C3-C18 heteroaryl;

[0033] The substituents in the substituted C6-C30 arylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C18 aryl group, and substituted C3-C18 heteroarylamine 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, C3-C30 heteroaryl group, C6-C30 arylamine group, and C3-C30 heteroarylamine.

[0034] Preferably, the formula (1) is selected from one of the following structures of formula 1-1 to formula 1-9:

[0035]

[0036] Among them, Ar 1 -Ar 3 The definition of is the same as above.

[0037] Preferably, in the formula (1), Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted B group; the B group includes: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzomethylcarbazolyl, dibenzocarbazolyl, phenyloxazolyl;

[0038] Wherein, the substituent of the substituted B group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amine, and C3-C30 heteroaromatic amine.

[0039] Preferably, the structure of formula (1) is represented by any one of the following B-1 to B-130:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] Preferably, in the formula (2), X 1 -X 14 All are selected from CR, R is selected from hydrogen or deuterium;

[0047] Preferably, X 1 -X 14 All are selected from CR, wherein R is selected from hydrogen;

[0048] Preferably, X 1 -X 6 Any one of them is selected from N, and the rest are CR;

[0049] Preferably, X 1 -X 6 Any one of them is selected from N, and the rest are CR, X 7 -X 14 Any one of them is selected from N, and the rest are CR;

[0050] Wherein, R exists independently and may be the same or different; R is defined as described above;

[0051] Preferably, Ar 4 -Ar 5 Each is independently selected from substituted or unsubstituted A groups;

[0052] The A group is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzomethylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenylbenzofuranyl, dibenzofuranofuranyl or phenylcarbazobenzofuranyl;

[0053] Wherein, the substituent of the substituted A group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine.

[0054] Preferably, the Ar 4 -Ar 5 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, or a group having the following structure:

[0055]

[0056] Multiple Ar ’ When they exist independently, they can be the same or different;

[0057] Among them, Ar ’each independently selected from a substituted or unsubstituted C group selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl or dibenzophenylcarbazolyl;

[0058] Wherein, the substituent of the substituted C group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine.

[0059] Preferably, the structure of formula (2) is represented by any of the following structures:

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] Preferably, the material of the light-emitting layer includes an organic electroluminescent material composition, and the organic electroluminescent material composition includes compounds having the following structures:

[0077]

[0078] In formula (3),

[0079] Wherein, ring A is a benzene ring;

[0080] Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine, substituted or unsubstituted C3-C30 heteroaryl;

[0081] L 4 Selected from substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C3-C30 heteroarylene groups;

[0082] The substituents in the substituted C6-C60 aryl, substituted C6-C60 arylamine, substituted C3-C60 heteroarylamine, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, and substituted C3-C30 heteroarylene are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0083]

[0084] Among them, X 1’ -X 14’ Each independently selected from N or CR ’ , R ’ is selected from hydrogen, deuterium, and C6-C30 aryl;

[0085] L 5 is independently selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 6 ,Ar 7 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group;

[0086] The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C60 aryl group, substituted C6-C60 aromatic amine group, substituted C3-C60 heteroaromatic amine group and substituted C3-C60 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, C3-C30 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

[0087] Preferably, in the organic electroluminescent material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 1:9-9:1;

[0088] Preferably, in the organic electroluminescent material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 2:8-8:2;

[0089] More preferably, in the organic electroluminescent material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 3:7-7:3;

[0090] Further preferably, in the organic electroluminescent material composition, the mass ratio of the compound having the structure of formula (3) to the compound having the structure of formula (4) is 4:6-6:4.

[0091] Preferably, in the formula (3), Ar is selected from a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted C6-C25 arylamine group, a substituted or unsubstituted C3-C25 heteroarylamine group, or a substituted or unsubstituted C3-C20 heteroaryl group;

[0092] Wherein, the substituents in the substituted C6-C25 aryl, substituted C6-C25 arylamine, substituted C3-C25 heteroarylamine, and substituted C3-C20 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine;

[0093] Preferably, Ar is selected from a substituted or unsubstituted D group, and the D group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthene, yl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl;

[0094] Wherein, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, C3-C30 heteroarylamine;

[0095] Preferably, in the formula (3), Ar is selected from phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino;

[0096] Preferably, in the formula (3), L 5 A substituted or unsubstituted C6-C15 arylene group; wherein the substituents in the substituted C6-C15 arylene group are each independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl;

[0097] Preferably, L 5 Selected from phenylene, biphenylene, naphthylene;

[0098] Preferably, L 5 Selected from phenylene and naphthylene.

[0099] Preferably, the formula (3) has a structure shown in any one of the following E-1 to E-208:

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] Preferably, in the formula (4), X 1’ -X 14’ All selected from CR ’ , R ’ The definitions stated above;

[0109] Preferably, X 1’ -X 6’ Any one of them is selected from N, and the rest are CR ’ , R ’ The definitions above;

[0110] Preferably, X 1’ -X 6’ Any one of them is selected from N, and the rest are CR ’ ;X 7’ -X 14’ Any one of them is selected from N, and the rest are CR ’ , R ’ The definitions stated above;

[0111] Preferably, R ’ is selected from hydrogen, deuterium, phenyl, naphthyl;

[0112] Ar 6 ,Ar 7 Each is independently selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl;

[0113] The substituents in the substituted C6-C18 aryl group and the substituted C3-C18 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0114] Preferably, Ar 6 ,Ar 7 Each is independently selected from a substituted or unsubstituted group E;

[0115] The group E is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenylbenzofuranyl, dibenzofuranofuranyl, phenylcarbazolylbenzofuranyl;

[0116] Wherein, the substituent in the substituted group E is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0117] Preferably, Ar 6 ,Ar 7 each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl;

[0118] Preferably, L 5 Each is independently selected from a connecting bond, a substituted or unsubstituted C6-C18 arylene group; wherein the substituent in the substituted C6-C18 arylene group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine;

[0119] Preferably, L 5 Selected from a connecting bond, a phenylene group.

[0120] Preferably, the formula (4) has a structure shown in any one of the following M-1 to M-723:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] Preferably, the first organic layer is adjacent to the light-emitting layer; the second organic layer is adjacent to the first layer;

[0138] Preferably, the organic electroluminescent device further comprises an anode, a hole injection layer, a hole transport layer, a second organic layer, a first organic layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked in sequence;

[0139] Optionally, the first organic layer is an electron blocking layer;

[0140] Optionally, the second organic layer is a light-emitting auxiliary layer.

[0141] The present invention also provides an organic electroluminescent device, comprising the organic electroluminescent device described above.

[0142] The term "organic electroluminescent material" disclosed in the present invention 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 an organic electroluminescent host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.

[0143] An organic electroluminescent material disclosed in the present invention may include an organic electroluminescent material, or may include a plurality of organic electroluminescent materials, wherein a plurality of organic electroluminescent materials means a material comprising a combination of at least two organic electroluminescent materials, and the material may be included in any layer constituting an organic electroluminescent device. It may mean both a material contained before the organic electroluminescent device (e.g., before vapor deposition) and a material contained after the organic electroluminescent device (e.g., after vapor deposition). For example, a material may be a combination of at least two compositions, and the composition 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. Two compositions in a plurality of organic electroluminescent materials may be included in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.

[0144] The term "organic electroluminescent host material composition" disclosed in the present invention means an organic electroluminescent material comprising a combination of at least two host materials. 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). The composition disclosed in the present invention may be contained in any light-emitting layer constituting an organic electroluminescent device. Two or more compounds of the multiple host materials contained in the composition disclosed in the present invention may be contained in one light-emitting layer, or may be contained in different light-emitting layers, respectively. For example: when two or more host materials are contained in one layer, the layer may be formed by mixed evaporation, or may be formed simultaneously by separate co-evaporation.

[0145] In the material composition, the mass ratio of the first compound to the second compound is 1:9-9:1;

[0146] Preferably, in the material composition, the mass ratio of the first compound to the second compound is 2:8-8:2;

[0147] More preferably, in the material composition, the mass ratio of the first compound to the second compound is 3:7-7:3;

[0148] Further preferably, in the material composition, the mass ratio of the first compound to the second compound is 4:6-6:4.

[0149] An anode and a cathode used in the present disclosure mean electrodes used in an organic light emitting device.

[0150] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0151] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0152] Hole injection layer

[0153] If necessary, the organic light emitting device according to the present disclosure may further include a hole injection layer on the anode.

[0154] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has the effect of injecting holes in the anode and has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and is excellent in the ability to form a thin film. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0155] Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

[0156] Hole transport layer

[0157] If necessary, the organic light-emitting device according to the present disclosure may include a hole transport layer on the anode (or on the hole injection layer if the hole injection layer is present).

[0158] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive injection of holes from the anode or the hole injection layer and transfer the holes to the light emitting layer.

[0159] Specific examples of the hole transport material include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion exist simultaneously, and the like, but are not limited thereto.

[0160] Light-emitting auxiliary layer

[0161] The organic light-emitting device according to the present disclosure includes a light-emitting auxiliary layer on a hole transport layer,

[0162] The light-emitting auxiliary layer improves light-emitting efficiency by enhancing hole injection characteristics and electron blocking characteristics for blocking electrons injected from the cathode to increase the recombination probability of holes and electrons, and by confining excitons generated in the light-emitting layer.

[0163] Electron blocking layer

[0164] If necessary, the organic light emitting device according to the present disclosure includes an electron blocking layer on the light emitting auxiliary layer.

[0165] The electron blocking layer means a layer disposed between the light-emitting auxiliary layer and the light-emitting layer to prevent the electrons injected by the cathode from transferring to the light-emitting auxiliary layer without recombining in the light-emitting layer, which can also be called an electron blocking layer or an electron suppression layer. The electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.

[0166] Luminescent layer

[0167] The light-emitting layer used in the present disclosure is a layer that can emit light in the visible light region by combining holes and electrons transmitted from the anode and the cathode. Generally, the light-emitting layer contains a host material and a dopant material, and in the present disclosure, contains one or more compounds represented by Chemical Formula 3 and one or more compounds represented by Chemical Formula 4 as host materials. For the type of doping material, it can be a fluorescent material or a phosphorescent material. For the amount of doping material, it is preferably 0.1 to 70% by mass, more preferably 0.1 to 30% by mass, further preferably 1 to 30% by mass, further preferably 1 to 20% by mass, and particularly preferably 1 to 10% by mass.

[0168] The fluorescent doping materials that can be used in the present invention may include: fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, etc., but are not limited thereto.

[0169] The phosphorescent doping material of the present invention may include, but is not limited to, heavy metal complexes, phosphorescent rare earth metal complexes, etc. Heavy metal complexes include, for example, iridium complexes, platinum complexes, osmium complexes, etc. Rare earth metal complexes include, for example, terbium complexes, europium complexes, etc., but are not limited to these.

[0170] Hole blocking layer

[0171] If necessary, the organic light emitting device according to the present disclosure may include a hole blocking layer on the light emitting layer.

[0172] The hole blocking layer is a layer disposed between the electron transport layer and the light emitting layer to prevent the holes injected by the anode from being transferred to the electron transport layer without being recombined in the light emitting layer. The hole blocking layer is preferably a material with high ionization energy.

[0173] Electron transport layer

[0174] If necessary, the organic light emitting device according to the present disclosure may include an electron transport layer on the light emitting layer.

[0175] The electron transport layer is a layer that receives electrons from the cathode or the electron injection layer formed on the cathode and transports the electrons to the light-emitting layer and suppresses the transfer of holes from the light-emitting layer, and the electron transport material is appropriately a material that can well receive the injection of electrons from the cathode and transfer the electrons to the light-emitting layer and has a large electron mobility.

[0176] Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used together with any desired cathode material as used according to conventional techniques. In particular, suitable examples of cathode materials are typical materials with a small work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0177] Electron injection layer

[0178] If necessary, the organic light-emitting device according to the present disclosure may further include a

[0179] In the electron transport layer, there is an electron injection layer (on the electron transport layer).

[0180] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and is also excellent in the ability to form a thin film.

[0181] Specific examples of the electron injection layer include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but are not limited thereto.

[0182] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0183] On the other hand, in the present disclosure, the “electron injection and transport layer” is a layer that functions as both an electron injection layer and an electron transport layer, and materials that function as each layer may be used alone or stacked and used in combination, but are not limited thereto.

[0184] In the present invention, the compound represented by formula (3) can be prepared by the following synthetic route, comprising the following steps:

[0185] 1. Synthesis of intermediate En-A: The reaction materials En-1 and En-2 are subjected to Suzuki cross-coupling reaction, and the reaction formula is as follows:

[0186]

[0187] 2. Synthesis of compound En: Intermediates En-A and En-B undergo Buchwald-Hartwig cross-coupling reaction, the reaction formula is as follows:

[0188]

[0189] Beneficial effects of the present invention:

[0190] The organic electroluminescent device provided by the present invention has a first organic layer comprising a compound having a structure of formula (1) and a second organic layer comprising a compound having a structure of formula (2) arranged on one side of the anode and the light-emitting layer. The first organic layer and the second organic layer act synergistically to effectively reduce the driving voltage of the organic electroluminescent device and improve the current efficiency of the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0191] 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.

[0192] Figure 1 A structural diagram of an organic electroluminescent device in an embodiment of the device of the present invention;

[0193] Among them: 1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-luminescence auxiliary layer, 6-electron blocking layer, 7-luminescent layer, 8-electron transport layer, 9-electron injection layer, 10-cathode. DETAILED DESCRIPTION

[0194] 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.

[0195] 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.

[0196] Example 1

[0197] This embodiment provides a method for preparing compound B-1, comprising the following steps:

[0198]

[0199] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 = 3:50) to obtain intermediate A1 (yield 85%).

[0200] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material A1 (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-1 (yield 65%).

[0201] Elemental analysis: C 48 H 33 N; Calculated value: C, 92.42; H, 5.33; N, 2.25; Found: C, 92.41; H, 5.34; N, 2.25; HRMS (ESI) m / z [M+H] + : Theoretical value: 623.80; measured value: 624.83.

[0202] Example 2

[0203] This embodiment provides a method for preparing compound B-2, comprising the following steps:

[0204]

[0205] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A2 (yield 83%).

[0206] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material A2 (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 the crude product is purified by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-2 (yield 61%).

[0207] Elemental analysis: C 52 H 33 NO2; Theoretical value: C, 88.74; H, 4.73; N, 1.99; O, 4.55; Found value: C, 88.71; H, 4.75; N, 1.99; HRMS (ESI) m / z [M+H] + : Theoretical value: 703.84; measured value: 704.89.

[0208] Example 3

[0209] This example provides a method for preparing compound B-4, comprising the following steps:

[0210]

[0211] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A4 (yield 87%).

[0212] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A4 (1.1 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-4 (yield 70%).

[0213] Elemental analysis: C 50 H 33 NS; theoretical value: C, 88.33; H, 4.89; N, 2.06; S, 4.72; found value: C, 88.36; H, 4.88; N, 2.05; S, 4.71; HRMS (ESI) m / z [M+H] + : Theoretical value: 679.88; measured value: 680.82.

[0214] Example 4

[0215] This embodiment provides a method for preparing compound B-7, comprising the following steps:

[0216]

[0217] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 = 3:50) to obtain intermediate A7 (yield 78%).

[0218] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A7 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 the crude product is purified by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-7 (yield 67%).

[0219] Elemental analysis: C 44 H 31 N; Calculated value: C, 92.11; H, 5.45; N, 2.44; Found: C, 92.14; H, 5.44; N, 2.42; HRMS (ESI) m / z [M+H] + : Theoretical value: 573.74; measured value: 574.78.

[0220] Example 5

[0221] This embodiment provides a method for preparing compound B-19, comprising the following steps:

[0222]

[0223] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A19 (yield 86%).

[0224] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A19 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-19 (yield 70%).

[0225] Elemental analysis: C 50 H 33 NO; Calculated: C, 90.47; H, 5.01; N, 2.11; O, 2.41; Found: C, 90.45; H, 5.02; N, 2.09; HRMS (ESI) m / z [M+H] + : Theoretical value: 663.82; measured value: 664.87.

[0226] Example 6

[0227] This embodiment provides a method for preparing compound B-23, comprising the following steps:

[0228]

[0229] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A23 (yield 84%).

[0230] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A23 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-23 (yield 63%).

[0231] Elemental analysis: C 46 H 26 D5NO; theoretical value: C, 89.29; H, 5.86; N, 2.26; O, 2.59; found value: C, 89.26; H, 5.87; N, 2.28; HRMS (ESI) m / z [M+H] + : Theoretical value: 618.79; measured value: 619.72.

[0232] Example 7

[0233] This embodiment provides a method for preparing compound B-26, comprising the following steps:

[0234]

[0235] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 = 3:50) to obtain intermediate A26 (yield 85%).

[0236] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A26 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-26 (yield 67%).

[0237] Elemental analysis: C 59 H 39 N; Calculated value: C, 93.00; H, 5.16; N, 1.84; Found: C, 93.03; H, 5.15; N, 1.82; HRMS (ESI) m / z [M+H] + : Theoretical value: 761.97; measured value: 762.91.

[0238] Example 8

[0239] This embodiment provides a method for preparing compound B-43, comprising the following steps:

[0240]

[0241] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A43 (yield 81%).

[0242] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A43 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-43 (yield 65%).

[0243] Elemental analysis: C 54 H 37 N; Calculated value: C, 92.67; H, 5.33; N, 2.00; Found: C, 92.63; H, 5.35; N, 2.02; HRMS (ESI) m / z [M+H] + : Theoretical value: 699.90; measured value: 700.93.

[0244] Example 9

[0245] This embodiment provides a method for preparing compound B-55, comprising the following steps:

[0246]

[0247] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A55 (yield 82%).

[0248] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A55 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, raise the temperature to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-55 (yield 67%).

[0249] Elemental analysis: C 54 H 37 N; Calculated value: C, 92.67; H, 5.33; N, 2.00; Found: C, 92.63; H, 5.35; N, 2.02; HRMS (ESI) m / z [M+H] + : Theoretical value: 699.90; measured value: 700.93.

[0250] Example 10

[0251] This embodiment provides a method for preparing compound B-79, comprising the following steps:

[0252]

[0253] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A79 (yield 79%).

[0254] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A79 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius 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 by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-79 (yield 63%).

[0255] Elemental analysis: C 54 H 37 N; Calculated value: C, 92.67; H, 5.33; N, 2.00; Found: C, 92.63; H, 5.35; N, 2.02; HRMS (ESI) m / z [M+H] + : Theoretical value: 699.90; measured value: 700.93.

[0256] Embodiment 11

[0257] This embodiment provides a method for preparing compound B-90, comprising the following steps:

[0258]

[0259] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A90 (yield 88%).

[0260] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A90 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-90 (yield 71%).

[0261] Elemental analysis: C 58 H 39 NO; Calculated: C, 90.95; H, 5.13; N, 1.83; O, 2.09; Found: C, 90.91; H, 5.15; N, 1.85; HRMS (ESI) m / z [M+H] + : Theoretical value: 765.96; measured value: 766.91.

[0262] Example 12

[0263] This example provides a method for preparing compound B-103, comprising the following steps:

[0264]

[0265] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material R (1 mmol), raw material S (1.05 mmol), tris(dibenzylideneacetone)palladium (0.03 mmol), Xphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, 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 = 3:50) to obtain intermediate A103 (yield 81%).

[0266] Take a 100 ml three-necked round-bottom flask and put in a stirring bar and a reflux tube. Under nitrogen protection, add raw material B (1 mmol), raw material A103 (1.1 mmol), tri(dibenzylideneacetone)palladium (0.03 mmol), Sphos (0.05 mmol), potassium tert-butoxide (2.5 mmol), toluene (10 mL) in sequence, heat to 110 degrees Celsius and react for 5 hours. After the reaction, cool to room temperature, filter, rinse the filter cake twice with deionized water and twice with ethanol, and then purify the crude product by recrystallization with toluene and tetrahydrofuran twice to obtain compound B-103 (yield 66%).

[0267] Elemental analysis: C 58 H 37 NO2; Theoretical value: C, 89.32; H, 4.78; N, 1.80; O, 4.10; Found: C, 89.35; H, 4.76; N, 1.79; HRMS (ESI) m / z [M+H] + : Theoretical value: 779.94; measured value: 780.96.

[0268] Example 16

[0269] This embodiment provides a method for preparing compound N-534, comprising the following steps:

[0270]

[0271] After nitrogen substitution in a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser, the intermediate N534-B (10 mmol), the intermediate N534-A (11 mmol) and 100 ml of toluene were added in sequence, heated to reflux to separate water for 0.5 h, cooled to 70-80 °C, sodium tert-butoxide (15 mmol), Pd2(dba)3 (0.05 mmol) and s-phos (0.1 mmol) were slowly added, and after the system was stabilized, it was heated to 100-110 °C and reacted for 3 h. Cool to 25-30°C, add 100 ml of water and 100 ml of toluene, stir and separate the liquids, extract the aqueous phase once with 100 ml of toluene, separate the liquids, combine the organic phases, add 7 g of anhydrous sodium sulfate to the organic phase, stir and dry, filter, concentrate the organic phase (-0.08-0.09 MPa, 55-60°C) until no liquid flows out, stir and add 40 ml of n-hexane, filter at room temperature 20-25°C to obtain compound N-534 with a yield of 58%.

[0272] Elemental analysis: C 42 H 29 NO theoretical value: C, 89.49; H, 5.19; N, 2.48; O, 2.84; found value: C, 89.47; H, 5.18; N, 2.51; HRMS (ESI) m / z (M+): theoretical value 563.22, found value 564.21.

[0273] Other compounds having the structure of formula (2) can be prepared by referring to the above preparation method, or by referring to the corresponding preparation method in the patent with publication number CN117720491 A (publication date 2024.03.19).

[0274] Embodiment 17

[0275] This embodiment provides a method for preparing compound E-1, comprising the following steps:

[0276]

[0277] Synthesis of intermediate E1-A

[0278] After nitrogen replacement to a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, raw material 10gE1-1 (36.63mmol), 5.72g E1-2 (36.63mmol), 0.85g tetrakis triphenylphosphine palladium (0.73mmol), 10.11g potassium carbonate (73.27mmol), 70mL toluene, 30mL ethanol, 30mL water were added in sequence. And the mixture was stirred at 65 ° C for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 10.06g of compound E1-A (yield 90%).

[0279] Synthesis of intermediate E1-B

[0280] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 10 g of intermediate E1-A (32.78 mmol), 3.1 g of E1-3 (32.78 mmol), 0.6 g of tris (dibenzylideneacetone) palladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 8.31 g of compound E1-B (yield 82%).

[0281] Synthesis of compound E-1

[0282] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 8.30 g of intermediate E1-B (26.85 mmol), 7.95 g of E1-4 (26.85 mmol), 0.49 g of tris (dibenzylideneacetone) palladium (0.54 mmol), 0.55 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.34 mmol), 5.16 g of sodium tert-butoxide (53.70 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 11.80 g of oxazole organic compound E-1 containing benzonaphthofuran (yield 76%).

[0283] Elemental analysis: C 41 H 26 N2O2; theoretical value: C, 85.10; H, 4.53; N, 4.84; O, 5.53; found value: C, 85.12; H, 4.52; N, 4.83; HRMS (ESI) m / z [M+H] +: theoretical value: 578.20; found value: 579.21.

[0284] Embodiment 18

[0285] This embodiment provides a method for preparing compound E-6, comprising the following steps:

[0286]

[0287] After nitrogen substitution in a three-necked reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate E1-A (32.78 mmol), 10.92 g of E6-3 (32.78 mmol), 0.6 g of tris (dibenzylideneacetone) palladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.3 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux at 110° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 14.41 g of compound E6-B (yield 73%).

[0288] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 10 g of intermediate E6-B (16.60 mmol), 4.91 g of E1-4 (16.60 mmol), 0.30 g of tris (dibenzylideneacetone) palladium (0.33 mmol), 0.34 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (0.83 mmol), 3.19 g of sodium tert-butoxide (33.21 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux at 110 ° C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried and purified by column chromatography to obtain 9.24 g of oxazole organic compound E-6 containing benzonaphthofuran (yield 68%).

[0289] Elemental analysis: C 60 H 38 N2O2; theoretical value: C, 88.00; H, 4.68; N, 3.42; O, 3.91; found value: C, 88.01; H, 4.68; N, 3.41; HRMS (ESI) m / z [M+H] +: theoretical value: 818.29; found value: 819.28.

[0290] Embodiment 19

[0291] This embodiment provides a method for preparing compound E-30, comprising the following steps:

[0292]

[0293] After nitrogen substitution in a three-necked reaction bottle equipped with a mechanical stirrer, a thermometer, and a condenser, 10 g of intermediate E1-A (32.78 mmol), 5.54 g of E30-3 (32.78 mmol), 0.60 g of tris (dibenzylideneacetone) palladium (0.66 mmol), 0.67 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.64 mmol), 6.30 g of sodium tert-butoxide (65.56 mmol), and 100 mL of toluene were added in sequence, and the mixture was stirred under reflux at 110° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 11.49 g of compound E30-B (yield 80%).

[0294] After nitrogen replacement in a three-mouth reaction bottle equipped with mechanical stirring, a thermometer, and a condenser, 10 g of intermediate E30-B (22.82 mmol), 6.75 g of E30-4 (22.82 mmol), 0.42 g of tris (dibenzylideneacetone) palladium (0.46 mmol), 0.47 g of 2-dicyclohexylphosphine-2', 6'-dimethoxybiphenyl (1.14 mmol), 4.39 g of sodium tert-butoxide (45.64 mmol), and 100 mL of toluene were added in sequence, and the mixture was refluxed at 110° C. for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate (EA), and residual moisture was removed by using anhydrous sodium sulfate, the residue was dried, and purified by column chromatography to obtain 10.75 g of oxazole organic compound E-30 containing benzonaphthofuran (yield 72%).

[0295] Elemental analysis: C 47 H 30 N2O2; theoretical value: C, 86.22; H, 4.62; N, 4.28; O, 4.89; found value: C, 86.20; H, 4.63; N, 4.29; HRMS (ESI) m / z [M+H] +: theoretical value: 654.23; found value: 654.24.

[0296] Embodiment 20

[0297] This embodiment provides a method for preparing compound M-17, comprising the following steps:

[0298]

[0299] Take 50 ml of double-necked round-bottom flask and put in a stirrer and a reflux tube, fill with nitrogen after drying, add compound M17-A (19.8mmol, CAS: 1884145-03-2), M17-B (20.75mmol, CAS: 1883265-32-4), tetrakis triphenylphosphine palladium (0.396mmol), potassium carbonate (39.6mmol), 35 ml of toluene, 15 ml of ethanol and 15 ml of distilled water, and stir the mixture at 90 degrees Celsius for 8 hours. After the reaction is complete, the mixture is added dropwise to methanol, and the solid is filtered. The solid is purified by column chromatography to obtain compound M-17 (8.5g, yield: 75%).

[0300] 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.

[0301] Examples 21-24

[0302] Examples 21-24 provide methods for preparing compounds M-76, M-253, M-394 or M-480. The specific preparation methods are as follows:

[0303] Raw materials Mn-B, raw material Mn-A, potassium carbonate and tetrakistriphenylphosphine palladium are added toluene, ethanol and water under nitrogen protection conditions, the temperature is raised to react, and after the reaction is completed, the final product is purified; the amount of substances used and the experimental parameters are the same as those in Example 60.

[0304] The structures and yields of the raw material Mn-B, raw material Mn-A and the product are shown in Table 1. The elemental analysis results of the prepared compound are shown in Table 2; wherein the amount of the substance and the experimental parameters are the same as those in Example 20.

[0305] Table 1

[0306]

[0307] The product characterization data are shown in Table 2:

[0308] Table 2

[0309]

[0310] Device Embodiment

[0311] This embodiment provides an organic electroluminescent device, such as Figure 1As shown, it includes an anode 2, a hole injection layer 3, a hole transport layer 4, a luminescent auxiliary layer 5, an electron blocking layer 6, a luminescent layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 which are sequentially stacked on a substrate 1, and its device structure is: anode (indium tin oxide (ITO) coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL) / luminescent auxiliary layer (Prime) / electron blocking layer (EBL) / luminescent layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / cathode (Al).

[0312] The materials used to manufacture the organic electroluminescent device are as follows:

[0313]

[0314] The preparation of the organic electroluminescent device comprises the following steps:

[0315] 1) Substrate cleaning:

[0316] 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.

[0317] 2) Preparation of organic layer:

[0318] Transfer the ITO transparent substrate to the evaporation equipment and evacuate to 1×10 -6 Up to 2×10 -4 Pa, sequentially deposit hole injection layer (HIL) / hole transport layer (HTL) / luminescent auxiliary layer (Prime) (second organic layer) / electron blocking layer (EBL) (first organic layer) / luminescent layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) / thick cathode (Al) on the anode film;

[0319] in:

[0320] The material of the hole injection layer (HIL) is a mixture of NDP-9 and HT, and the specific mass ratio is shown in Table 3;

[0321] The materials of the hole transport layer (HTL) are shown in Table 3;

[0322] The materials of the light-emitting auxiliary layer (Prime) are shown in Table 3;

[0323] The materials of the electron blocking layer (EBL) are shown in Table 3;

[0324] The light-emitting layer (EML) is vacuum evaporated in a co-evaporation manner. The material of the light-emitting layer includes a host material and a guest material, wherein the guest material is (piq)2Ir(acac). The specific material of the host material and the ratio of the host material to the guest material are shown in Table 3;

[0325] The materials of the electron transport layer (ETL) are shown in Table 3;

[0326] The material of the electron injection layer (EIL) is LiQ;

[0327] The cathode is aluminum;

[0328] Some layers of the organic electroluminescent device and their materials and thicknesses are shown in Table 3:

[0329] Table 3

[0330]

[0331]

[0332]

[0333] The embodiments in the table represent device embodiments, and the comparative examples in the table are device comparative examples.

[0334] Test Case

[0335] The organic electroluminescent devices obtained from device examples 1 to 16 and comparative examples 1 to 3 in the device examples were tested.

[0336] Instruments: The current, voltage, brightness and other characteristics of the device are tested synchronously using a PR 650 spectrum scanning brightness meter and a Keithley K2400 digital source meter system;

[0337] Test conditions: Photoelectric characteristics test conditions: Current density is 10mA / cm2.

[0338] Life test: The current density is 50 mA / cm2, and the time (in hours) when the device brightness drops to 95% of the original brightness is recorded.

[0339] The device performance test results are shown in Table 4:

[0340] Table 4

[0341] project Driving voltage(V) Current efficiency (Cd / A) Lifespan T95(hrs) Example 1 3.02 39.35 367.2 Example 2 3.01 39.38 369.4 Example 3 2.96 39.42 367.1 Example 4 2.96 39.58 379.7 Example 5 2.96 39.80 373.5 Example 6 3.01 39.77 370.7 Example 7 3.03 39.36 365.2 Example 8 3.02 39.58 364.7 Example 9 3.04 39.39 373.2 Example 10 3.00 39.54 369.3 Embodiment 11 2.97 39.21 373.7 Example 12 3.00 39.64 367.5 Example 13 3.00 39.98 375.3 Embodiment 14 3.00 39.68 372.2 Embodiment 15 3.01 39.61 364.5 Example 16 2.96 40.34 387.4 Comparative Example 1 3.14 37.27 355.7 Comparative Example 2 2.86 38.42 368.9 Comparative Example 3 3.25 32.14 361.2

[0342] 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 device, comprising a cathode and an anode arranged opposite to each other, and a light-emitting layer located between the cathode and the anode, characterized in that: Also includes: a first organic layer located between the anode and the light-emitting layer; a second organic layer located between the anode and the light-emitting layer; Wherein, the first layer of material comprises a compound having the following structure: In formula (1), L 1 -L 3 Each is independently selected from a substituted or unsubstituted non-fused C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C3-C60 heteroarylamine group, and a substituted or unsubstituted C3-C30 heteroaryl group; The second organic layer material comprises a compound having the following structure: Among them, X 1 -X 14 Each is independently selected from N or CR, and R is selected from hydrogen or deuterium; Ar 4 ,Ar 5 Each is independently selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, a substituted or unsubstituted C6-C60 arylamine group, and a substituted or unsubstituted C3-C60 heteroarylamine group; The substituents in the substituted C6-C30 arylene group, substituted C3-C30 heteroarylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C60 aromatic amine group and substituted C3-C60 heteroaromatic amine 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, C3-C30 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

2. The organic electroluminescent device according to claim 1, characterized in that: In the formula (1), L 1 -L 3 Each is independently selected from a substituted or unsubstituted non-fused C6-C30 arylene group; Wherein, the substituent in the substituted non-fused C6-C30 arylene group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine; Preferably, Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group; Wherein, the substituents in the substituted C6-C60 aryl group and the substituted C3-C30 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine; Preferably, L 1 -L 3 Each independently selected from phenylene, biphenylene; Ar 1 -Ar 3 Each is independently selected from substituted or unsubstituted C6-C18 aryl, C3-C18 heteroaryl; The substituents in the substituted C6-C30 arylene group, substituted C6-C30 aryl group, substituted C3-C30 heteroaryl group, substituted C6-C18 aryl group, and substituted C3-C18 heteroarylamine 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, C3-C30 heteroaryl group, C6-C30 arylamine group, and C3-C30 heteroarylamine.

3. The organic electroluminescent device according to claim 1 or 2, characterized in that: The formula (1) is selected from one of the following structures: Among them, Ar 1 -Ar 3 The definition is the same as that of claim 1.

4. The organic electroluminescent device according to any one of claims 1 to 3, characterized in that: In the formula (1), Ar 1 -Ar 3 Each is independently selected from a substituted or unsubstituted B group; the B group includes: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzomethylcarbazolyl, dibenzocarbazolyl, phenyloxazolyl; Wherein, the substituent of the substituted B group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 aromatic amine, and C3-C30 heteroaromatic amine.

5. The organic electroluminescent device according to any one of claims 1 to 3, characterized in that: The structure of formula (1) is represented by any one of the following B-1 to B-130:

6. The organic electroluminescent device according to any one of claims 1 to 5, characterized in that: In the formula (2), X 1 -X 14 All are selected from CR, R is selected from hydrogen or deuterium; Preferably, X 1 -X 14 All are selected from CR, wherein R is selected from hydrogen; Preferably, X 1 -X 6 Any one of them is selected from N, and the rest are CR; Preferably, X 1 -X 6 Any one of them is selected from N, and the rest are CR, X 7 -X 14 Any one of them is selected from N, and the rest are CR; Wherein, R exists independently and may be the same or different; R is defined as in claim 1; Preferably, Ar 4 -Ar 5 Each is independently selected from substituted or unsubstituted A groups; The A group is selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzomethylcarbazolyl, dibenzocarbazolyl, biphenylcarbazolyl, phenanthrenylbenzofuranyl, dibenzofuranofuranyl or phenylcarbazobenzofuranyl; Wherein, the substituent of the substituted A group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine.

7. The organic electroluminescent device according to any one of claims 1 to 6, characterized in that: The Ar 4 -Ar 5 Each is independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, or a group having the following structure: Multiple Ar ’ When they exist independently, they can be the same or different; Among them, Ar ’ each independently selected from a substituted or unsubstituted C group selected from: phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl or dibenzophenylcarbazolyl; Wherein, the substituent of the substituted C group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 aromatic amine, and C3-C60 heteroaromatic amine.

8. The organic electroluminescent device according to any one of claims 1 to 7, characterized in that: The structure of formula (2) is represented by any of the following structures:

9. The organic electroluminescent device according to claims 1 to 8, characterized in that: The material of the light-emitting layer includes an organic electroluminescent material composition, and the organic electroluminescent material composition includes compounds having the following structures: In formula (3), Wherein, ring A is a benzene ring; Ar is selected from substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C3-C60 heteroarylamine, substituted or unsubstituted C3-C30 heteroaryl; L 4 Selected from substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C3-C30 heteroarylene groups; The substituents in the substituted C6-C60 aryl, substituted C6-C60 arylamine, substituted C3-C60 heteroarylamine, substituted C3-C30 heteroaryl, substituted C6-C30 arylene, and substituted C3-C30 heteroarylene are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; In formula (4), Among them, X 1’ -X 14’ Each independently selected from N or CR ’ , R ’ is selected from hydrogen, deuterium, and C6-C30 aryl; L 5 is independently selected from a connecting bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C3-C30 heteroarylene group; Ar 6 ,Ar 7 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-C60 aryl group, substituted C6-C60 aromatic amine group, substituted C3-C60 heteroaromatic amine group and substituted C3-C60 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, C3-C30 heteroaromatic group, C6-C60 aromatic amine group and C3-C60 heteroaromatic amine group.

10. The organic electroluminescent device according to claims 1 to 9, characterized in that: In the formula (3), Ar is selected from a substituted or unsubstituted C6-C25 aryl group, a substituted or unsubstituted C6-C25 arylamine group, a substituted or unsubstituted C3-C25 heteroarylamine group, or a substituted or unsubstituted C3-C20 heteroaryl group; Wherein, the substituents in the substituted C6-C25 aryl, substituted C6-C25 arylamine, substituted C3-C25 heteroarylamine, and substituted C3-C20 heteroaryl are each independently selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, and C3-C30 heteroarylamine; Preferably, Ar is selected from a substituted or unsubstituted D group, and the D group is selected from the following groups: phenyl, naphthyl, biphenyl, phenanthryl, fluoranthene, yl, terphenyl, triphenylene, phenalenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylmethylfluorenyl, diphenylfluorenyl, pyridyl, pyridylphenyl, phenylpyridyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, benzonaphthofuranyl, benzonaphthothienyl, spiro[fluorene-9,9'-xanthenyl]yl, phenylmethylfluorenyl, dinaphthofuranyl, dinaphthothienyl, dibenzothienyl, N,N-diphenylanilinoyl; Wherein, the substituent of the substituted D group is selected from one or a combination of at least two of deuterium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C30 arylamine, C3-C30 heteroarylamine; Preferably, in the formula (3), Ar is selected from phenyl, naphthyl, biphenyl, phenanthrenyl, terphenyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, phenanthrenyl, dibenzofuranyl, benzonaphthofuranyl, N,N-diphenylanilino; Preferably, in the formula (3), L 5 A substituted or unsubstituted C6-C15 arylene group; wherein the substituents in the substituted C6-C15 arylene group are each independently selected from one or a combination of at least two of deuterium, halogen, and C1-C62 alkyl; Preferably, L 5 Selected from phenylene, biphenylene, naphthylene; Preferably, L 5 Selected from phenylene and naphthylene.

11. The organic electroluminescent device according to claims 1 to 10, characterized in that: The formula (3) has a structure shown in any one of the following E-1 to E-208:

12. The organic electroluminescent device according to claims 1 to 11, characterized in that: In the formula (4), X 1’ -X 14’ All selected from CR ’ , R ’ The definition is the same as claim 9; Preferably, X 1’ -X 6’ Any one of them is selected from N, and the rest are CR ’ , R ’ The definition is the same as claim 9; Preferably, X 1’ -X 6’ Any one of them is selected from N, and the rest are CR ’ ;X 7’ -X 14’ Any one of them is selected from N, and the rest are CR ’ , R ’ The definition is the same as claim 9; Preferably, R ’ is selected from hydrogen, deuterium, phenyl, naphthyl; Ar 6 ,Ar 7 Each is independently selected from substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl; The substituents in the substituted C6-C18 aryl group and the substituted C3-C18 heteroaryl group are selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, Ar 6 ,Ar 7 Each is independently selected from a substituted or unsubstituted group E; The group E is selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthene, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, benzofuranyl, dibenzofuranyl, naphthobenzofuranyl, dinaphthofuranyl, benzothienyl, dibenzothienyl, naphthobenzothienyl, carbazolyl, phenylcarbazolyl, benzophenylcarbazolyl, dibenzophenylcarbazolyl, biphenylcarbazolyl, phenanthrenylbenzofuranyl, dibenzofuranofuranyl, phenylcarbazolylbenzofuranyl; Wherein, the substituent in the substituted group E is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, Ar 6 ,Ar 7 each independently selected from phenyl, naphthyl, biphenyl, terphenyl, phenanthryl, fluoranthenyl, triphenylene, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirobifluorenyl, benzodimethylfluorenyl, benzodiphenylfluorenyl, benzospirobifluorenyl, dibenzofuranyl, naphthiobenzofuranyl, dibenzothiophenyl, naphthiobenzothiophenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl; Preferably, L 5 Each is independently selected from a connecting bond, a substituted or unsubstituted C6-C18 arylene group; wherein the substituent in the substituted C6-C18 arylene group is selected from one or a combination of two of deuterium, halogen, cyano, C1-C6 alkyl, C3-C30 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, C6-C60 arylamine, and C3-C60 heteroarylamine; Preferably, L 5 Selected from a connecting bond, a phenylene group.

13. The organic electroluminescent device according to claims 1 to 12, characterized in that: The formula (4) has a structure shown in any one of the following M-1 to M-723:

14. The organic electroluminescent device according to claim 1, characterized in that: The first organic layer is adjacent to the light-emitting layer; the second organic layer is adjacent to the first layer; Preferably, the organic electroluminescent device further comprises an anode, a hole injection layer, a hole transport layer, a second organic layer, a first organic layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked in sequence.

15. An organic electroluminescent device, characterized in that: The organic electroluminescent device comprises the organic electroluminescent device according to claims 1 to 14.

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