Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. The nitrogen-containing heterocyclic compound provided by the invention has relatively good hole blocking capability and relatively high electron mobility, and is applied to the organic electroluminescent device as an electron transport layer material or a hole blocking layer material, so that the transport balance of electrons and holes in the device is increased, the holes can be effectively blocked in a luminous layer, and the luminous efficiency of the organic electroluminescent device is improved. Part of holes are prevented from being compounded with electrons outside the light-emitting layer, the compounding probability of the electrons and the holes in the light-emitting layer is improved, the light-emitting efficiency of the device is effectively improved, the service life of the device is effectively prolonged, and good application effects and industrialization prospects are achieved.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof. BACKGROUND

[0002] Organic Light-Emitting Diode (OLED) is also called organic electroluminescent diode, which is widely used in display and lighting and many other fields due to its fast response, wide viewing angle, light weight, wide temperature range, low energy consumption, high definition, strong flexibility and full-color panel display.

[0003] The organic electroluminescent device can be divided into single-layer device, double-layer device and multi-layer device according to the structure, and the multi-layer device is composed of anode, cathode and organic layer, and the organic layer includes hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer and cover layer. Organic electroluminescence refers to the phenomenon that when the organic optoelectronic material is driven by current or electric field, the electrons and holes are injected and transported from the cathode and anode into the organic layer, and the two are recombined in the light emitting layer to generate excitons. The excitons transfer energy to the organic light emitting molecules, making them jump from the ground state to the excited state. The excited state molecules are unstable, and when the excited molecules return to the ground state, the energy is released in the form of light, resulting in the phenomenon of light emission.

[0004] High-quality organic electroluminescent devices need to meet the characteristics of high luminous efficiency and long service life. However, the development of organic electroluminescent materials is not perfect at present, and there are still many problems in preparing high-quality organic electroluminescent devices. For the electron transport layer material, on the one hand, due to the high hole mobility of the hole transport layer material, the hole mobility of the electron transport layer material is higher than that of the hole transport layer material, which leads to the imbalance of the transmission of holes and electrons, and the high-efficiency recombination in the light emitting layer. On the other hand, in the light emitting layer, part of the holes do not recombine with the electrons to form excitons, but pass through the light emitting layer and recombine with the electrons at the interface between the electron transport layer and the light emitting layer or in the electron transport layer. In order to avoid this situation, a material with hole blocking ability is often introduced to block the holes in the light emitting layer, so that the electrons and holes can recombine in the light emitting layer to form excitons and emit light, thereby improving the luminous efficiency of the device. Therefore, it is crucial to design an organic electroluminescent material with high electron transport efficiency and hole blocking ability, which can reduce energy consumption, improve the luminous efficiency of the device and prolong the service life of the device. SUMMARY

[0005] In order to solve the problem of low performance of the organic electroluminescent device in the prior art, the present application provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof.

[0006] The present application provides a nitrogen-containing heterocyclic compound having the following formula I-1 or formula I-2,

[0007]

[0008] In formula I-1, the x, v are the same as or different from each other, selected from C(R2) or N atom, and at least one of the v is selected from N atom, when x or v is bonded with other groups, the x or v is selected from C atom;

[0009] The A is selected from the group shown in formula II-2;

[0010]

[0011] In formula I-2, the z is the same as or different from each other, selected from C(R5) or N atom, and at least one of the z is selected from N atom, when z is bonded with other groups, the z is selected from C atom;

[0012] The E is selected from the group shown in formula II-1;

[0013] The B, C, D, F, H, G are the same as or different from each other, selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, and at least one of the B, C and D in formula I-1 is selected from the group shown in formula III, and at least one of the H and G in formula I-2 is selected from the group shown in formula III;

[0014] The a is the same as or different from each other, selected from CH or N atom, when a is bonded with other groups, the a is selected from C atom;

[0015] The R a , R b are the same as or different from each other, selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; or the R a , R b between them can be connected to form a substituted or unsubstituted ring; or any one of R a , R b may be directly bonded with L1;

[0016] said R m , R n are the same or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or any two of said R m , R n may be connected to each other to form a substituted or unsubstituted ring; or any one of said R m , R n may be directly bonded to L1;

[0017] said R are the same or different from each other, and are selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl;

[0018] said R1, R2, R5, R6 are the same or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, when there are two or more R2, R5, the two or more R2, R5 are the same or different from each other, or adjacent two R2, R5 can be connected to each other to form a substituted or unsubstituted ring;

[0019] said m is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when there are two or more R1, the two or more R1 are the same or different from each other, or adjacent two R1 can be connected to each other to form a substituted or unsubstituted ring;

[0020] said n is selected from 0, 1, 2 or 3, when there are two or more R6, the two or more R6 are the same or different from each other, or adjacent two R6 can be connected to each other to form a substituted or unsubstituted ring;

[0021] said L1-L4 are the same or different from each other, and are selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroarylene, and combinations thereof.

[0022] The present application also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is positioned between the anode and the cathode or outside of either of the anode and the cathode, and the organic layer comprises any one or more of the nitrogen-containing heterocyclic compounds.

[0023] Beneficial effects: The nitrogen-containing heterocyclic compounds provided by the present application, when applied to an organic electroluminescent device, can effectively improve the electron mobility of the electron transport layer material, increase the transport balance of electrons and holes in the device, effectively block holes in the light-emitting layer as a hole blocking layer material, avoid the recombination of part of the holes outside the light-emitting layer with electrons, improve the recombination probability of electrons and holes in the light-emitting layer, and thus significantly improve the light-emitting efficiency and service life of the device. DETAILED DESCRIPTION

[0024] The technical solutions of specific embodiments of the present application will be described below in a clear and complete manner. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative labor fall within the protection scope of the present application.

[0025] In the compounds of the present application, any atom not designated as a particular isotope includes any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0026] In the present specification, “*” means the moiety connected to another substituent.

[0027] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any one of the corresponding optional sites of the ring. For example, may mean may mean may mean and so on.

[0028] In the present specification, when a substituent or a connecting site is through a bond between two or more rings, it means that it can be connected to any one of the two or more rings, and specifically can be connected to any one of the corresponding optional sites of the ring. For example, may mean or may mean and so on.

[0029] Examples of the halogen atom described in the present application can include fluorine, chlorine, bromine, or iodine.

[0030] The alkyl group according to the present application means a monovalent group obtained by removing one hydrogen atom from an alkane molecule, which can be a straight-chain alkyl group or a branched alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples can include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and the like, but are not limited thereto.

[0031] The alkenyl group according to the present application means a monovalent group obtained by removing one hydrogen atom from an alkene molecule, which can be a straight-chain alkenyl group or a branched alkenyl group, preferably having 2 to 25 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 6 carbon atoms. The alkenyl group can be substituted or unsubstituted. Specific examples can include ethenyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylethenyl-1-yl, phenethyl, and the like, but are not limited thereto.

[0032] The cycloalkyl group according to the present application means a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like, but is not limited thereto.

[0033] The "substituted or unsubstituted silyl group" according to the present application means a —Si(R k )3 group, wherein each R k is the same or different selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C30 alicyclic and C6 to C60 aromatic fused ring group, and a substituted or unsubstituted C3 to C30 alicyclic and C2 to C60 heteroaromatic fused ring group. Preferably, each R kthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R k the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl group" means a silyl group substituted with a substituted or unsubstituted C3-C25 alkyl group or aryl group, which is preferably substituted with 3 alkyl groups, 3 aryl groups. Examples of the "substituted or unsubstituted silyl group", in particular, the "substituted or unsubstituted C3-C25 silyl group" can include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, and the like, but are not limited thereto.

[0034] The aryl group according to the present application means a monovalent group obtained by removing one hydrogen atom from the aromatic ring carbon of an aromatic compound molecule, and can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, a phenyl group, and the like, but is not limited thereto. The polycyclic aryl group means an aryl group having two or more independent aromatic rings in the molecule, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but is not limited thereto. The fused ring aryl group means an aryl group having two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a fluoranthenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a benzofluorenyl group, a 9,9'-spirobifluorenyl group, and the like, but is not limited thereto.

[0035] ​The heteroaryl group according to the present application refers to the group of radicals obtained by replacing one or more of the ring carbon atoms in an aryl group with a heteroatom, including but not limited to O, S, N, Si or P atom, preferably having 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, most preferably 2 to 12 carbon atoms. The connecting site of the heteroaryl group can be located on the ring carbon atom or on the ring heteroatom, and the heteroaryl group can be monocyclic, polycyclic or fused ring heteroaryl group. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, bipyrimidyl, phenylpyridyl, phenylpyrimidyl, etc., but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolyl, quinoxalyl, benzoquinazolyl, benzoquinoxalyl, phenanthrolinyl, naphthylidinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzothienyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, spirofluorene xanthene, spirofluorene thioxanthene, etc., but is not limited thereto.

[0036] The aliphatic ring according to the present application refers to the cyclic hydrocarbon having aliphatic property, containing closed carbon ring in the molecule, preferably having 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, further preferably 3 to 12 carbon atoms, more preferably 3 to 7 carbon atoms. It can form a single ring hydrocarbon or a polycyclic hydrocarbon, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple single ring hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure.

[0037] The fused ring of the aromatic ring and the aliphatic ring according to the present application refers to a ring in which one or more aromatic rings and one or more aliphatic rings are fused to each other by sharing two adjacent carbon atoms, the aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and the aliphatic ring preferably has 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused ring of the aromatic ring and the aliphatic ring can be substituted or unsubstituted. Examples include benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropanyl, naphthocyclobutanyl, naphthocyclopentanyl, naphthocyclohexanyl, naphthocyclopentenyl, naphthocyclohexenyl, and the like, but are not limited thereto.

[0038] The arylene group according to the present application refers to a general term for a divalent group obtained by removing two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and can be a monocyclic arylene group, a polycyclic arylene group, or a fused ring arylene group, preferably has 6 to 30 carbon atoms, more preferably has 6 to 22 carbon atoms, more preferably has 6 to 18 carbon atoms, and most preferably has 6 to 12 carbon atoms. As the monocyclic arylene group, phenylene and the like can be used, but are not limited thereto. The arylene group can be substituted or unsubstituted. As the polycyclic arylene group, biphenylene, terphenylene, quaterphenylene, and the like can be used, but are not limited thereto. As the fused ring arylene group, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, fluorenylene, spirofluorenylene, triphenylenylene, perylenylene, fluoranthenylene, and the like can be used, but are not limited thereto.

[0039] ​The heteroarylene group according to the present application refers to a general term of divalent group obtained by removing two hydrogen atoms from the core carbon of the aromatic heterocycle composed of carbon and heteroatom, and the heteroatom can be one or more of N, O, S, Si, P, and can be monocyclic heteroarylene, polycyclic heteroarylene or fused ring heteroarylene, preferably having 2 to 30 carbon atoms, more preferably having 2 to 22 carbon atoms, still more preferably having 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms, and the heteroarylene group can be substituted or unsubstituted. Examples can include pyridylene, pyrimidylene, pyrazylene, pyridazylene, triazylene, thiophenylene, pyrrolylene, furanylene, pyranylene, oxazolyiene, thiazolyiene, imidazolyiene, benzoxazolyiene, benzothiazolyiene, benzimidazolyiene, carbazolyiene, benzocarbazolyiene, azidylene, xanthylene, thianthrene, phenazinylene, phenothiazinylene, phenoxazinylene, indolyiene, quinolyiene, isoquinolyiene, benzothiophenylene, benzofuranylene, dibenzofuranylene, dibenzothiophenylene, quinoxalyiene, quinazolyiene, naphtholyiene, purinylene, phenanthrolinylene, and the like, but are not limited thereto.

[0040] The divalent aromatic ring and aliphatic ring fused ring group according to the present application refers to a divalent group having two linking positions on the aromatic ring and aliphatic ring fused ring group. They can be applicable to the above description of the aromatic ring and aliphatic ring fused ring group except that they are divalent groups, respectively.

[0041] The "unsubstituted" in the "substituted or unsubstituted" according to the present application means that the hydrogen atom on the group is not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When a plurality of hydrogens are substituted by a plurality of substituents, the plurality of substituents can be the same or different.

[0042] The substituents described in the "substituted or unsubstituted" of this invention may be the same as or different from each other, and are selected from any one of deuterium, cyano, nitro, trifluoromethyl, halogen atom, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, preferably deuterium, cyano, halogen atom, trifluoromethyl The compounds include C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C3-C25 silyl groups, C6-C30 aryl groups, and C2-C30 heteroaryl groups. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracene, phenanthrene, pyrene, and triphenylene. yl, peryl, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, carbazole, 9-phenylcarbazole, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, pyridine Phosphoryl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, oxazolyl, thiazolyl, imidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, phenothiazinyl, phenothiazinyl, acridineyl, etc., but not limited to these.

[0043] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0044]

[0045] In the present specification, a ring formed by linking can be an aromatic ring or a non-aromatic ring, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a fused ring, and the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, and the like, but is not limited thereto.

[0046] In the present application, "at least one" means one, two, three, four, five, six, or more.

[0047] The present application provides a nitrogen-containing heterocyclic compound having a structure represented by Formula I-1 or Formula I-2,

[0048]

[0049] In Formula I-1, x and v are the same as or different from each other, and are selected from a C(R2) or N atom, and at least one of v is selected from an N atom, and when x or v is bonded to another group, x or v is selected from a C atom;

[0050] A is selected from a group represented by Formula II-2;

[0051]

[0052] In Formula I-2, z is the same as or different from each other, and is selected from a C(R5) or N atom, and at least one of z is selected from an N atom, and when z is bonded to another group, z is selected from a C atom;

[0053] E is selected from a group represented by Formula II-1;

[0054] B, C, D, F, H, and G are the same as or different from each other, and are selected from any one of a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C25 silyl group, a substituted or unsubstituted condensed ring group of a C6-C30 aromatic ring and a C3-C30 aliphatic ring, and a substituted or unsubstituted C2-C30 heteroaryl group, and at least one of B, C, and D in Formula I-1 is selected from a group represented by Formula III, and at least one of H and G in Formula I-2 is selected from a group represented by Formula III;

[0055] a is the same as or different from each other, and is selected from a CH or N atom, and when a is bonded to another group, a is selected from a C atom;

[0056] R a , R bThey may be identical or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl; or the R a R b They can connect to each other to form substituted or unsubstituted rings; or R a R b Either of them can be directly bonded to L1;

[0057] The R m R n They may be identical or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R m R n They can connect to each other to form substituted or unsubstituted rings; or R m R n Either of them can be directly bonded to L1;

[0058] The Rs may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1 to C25 alkyl, substituted or unsubstituted C3 to C25 cycloalkyl;

[0059] The R1, R2, R5, and R6 may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, and substituted or unsubstituted C2-C30 heteroaryl. When there are two or more R2 and R5, the two or more R2 and R5 may be the same as or different from each other, or two adjacent R2 and R5 may be connected to each other to form substituted or unsubstituted rings.

[0060] said m is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when there are two or more R1, the two or more R1 are the same or different from each other, or adjacent two R1 can be connected to each other to form a substituted or unsubstituted ring;

[0061] said n is selected from 0, 1, 2 or 3, when there are two or more R6, the two or more R6 are the same or different from each other, or adjacent two R6 can be connected to each other to form a substituted or unsubstituted ring;

[0062] said L1-L4 are the same or different from each other, selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, a substituted or unsubstituted C2-C30 heteroarylene and a combination thereof.

[0063] Preferably, in formula I-1, one, two or three of said v are selected from N atoms; one, two or three of said x are selected from N atoms.

[0064] Preferably, in formula I-2, one, two or three of said z are selected from N atoms.

[0065] Preferably, said formula I-1 is selected from the following structures:

[0066]

[0067] Preferably, said formula I-2 is selected from the following structures:

[0068]

[0069] Preferably, at least one of said B, C and D is selected from the group represented by formula III, which means that at least one, at least two or at least three of B, C and D are selected from the group represented by formula III.

[0070] Preferably, said B, C or D is selected from the group represented by formula III.

[0071] Preferably, said B and C, or said C and D are selected from the group represented by formula III.

[0072] Preferably, said B, C and D are selected from the group represented by formula III.

[0073] Preferably, at least one of said H and G is selected from the group represented by formula III, which means that at least one or at least two of H and G are selected from the group represented by formula III.

[0074] Preferably, said H or G is selected from the group represented by formula III.

[0075] Preferably, said H and G are selected from the group represented by formula III.

[0076] Preferably, said formula II-1 is selected from any one of the following groups:

[0077]

[0078] said a are identical to or different from each other and are selected from CH or N atoms, said a are selected from C atoms when a is bonded to other groups;

[0079] said Y is selected from O, S, C(R x R y ), N(R z ) or any one of the following groups;

[0080] said ring A is selected from a substituted or unsubstituted C3-C10aliphatic ring;

[0081] said R m , R n are identical to or different from each other and are selected from hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12alkyl, C3-C12cycloalkyl: cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, adamantanyl, norbornanyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl or benzothiophenyl;

[0082] said a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0083] said R x , R y are identical to or different from each other and are selected from hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C3-C25silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C6-C30aromatic and C3-C30aliphatic fused ring group, substituted or unsubstituted C2-C30heteroaryl or any one of the following groups: x y ​may be connected to each other to form a substituted or unsubstituted ring;

[0084] said R z selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C25 alkyl group, a substituted or unsubstituted C2-C25 alkenyl group, a substituted or unsubstituted C3-C25 cycloalkyl group, a substituted or unsubstituted C3-C25 silyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, a substituted or unsubstituted C2-C30 heteroaryl group, or said R z may be directly bonded to L1;

[0085] said L m selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, a substituted or unsubstituted C2-C30 heteroarylene group, and a combination thereof.

[0086] Preferably, in each of the groups of Formula II-1, at most 2 or at most 1 of the 4 a of each ring is selected from N atom.

[0087] More preferably, in each of the groups of Formula II-1, at most 2 or at most 1 of the 4 a of each ring is selected from N atom.

[0088] Preferably, said Formula II-1 is selected from any one of the following groups:

[0089]

[0090]

[0091]

[0092] R1is selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12alkyl, C3-C12cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, or benzothiophenyl;

[0093] b1is selected from 0, 1, 2, 3, 4, 5, 6, or 7, b2is selected from 0, 1, 2, 3, 4, 5, or 6, b3is selected from 0, 1, 2, 3, 4, or 5, b4is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, b5is selected from 0, 1, 2, 3, or 4, b6is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, b7is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, b8is selected from 0, 1, 2, or 3, b9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, b 10 b1is selected from 0, 1, 2, 3, 4, 5, 6, or 7, b2is selected from 0, 1, 2, 3, 4, 5, or 6, b3is selected from 0, 1, 2, 3, 4, or 5, b4is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, b5is selected from 0, 1, 2, 3, or 4, b6is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, b7is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, b8is selected from 0, 1, 2, or 3, b9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, b 11 b1is selected from 0, 1, 2, 3, 4, 5, 6, or 7, b2is selected from 0, 1, 2, 3, 4, 5, or 6, b3is selected from 0, 1, 2, 3, 4, or 5, b4is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, b5is selected from 0, 1, 2, 3, or 4, b6is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, b7is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, b8is selected from 0, 1, 2, or 3, b9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, b

[0094] Preferably, formula II-2 is selected from formula II-1 or any one of the following groups:

[0095]

[0096] a is selected from CH or N atom, and when a is bonded with other groups, a is selected from C atom;

[0097] R1is selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, or benzothiophenyl;

[0098] f1is selected from 0, 1, 2, 3, 4, 5, 6, or 7, f2is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, f3is selected from 0, 1, 2, 3, or 4, f4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, f5is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, f6is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and f7is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0099] Preferably, in each of the groups of formula II-2, at most 2 or at most 1 of the 4 a of each ring is selected from N atom.

[0100] More preferably, in each of the groups of formula II-2, at most 2 or at most 1 of the 4 a of each ring is selected from N atom.

[0101] Preferably, the group of formula III is selected from any one of the following groups:

[0102]

[0103] Preferably, L1-L4are the same or different from each other, selected from a single bond or any one of the following groups and combinations thereof:

[0104]

[0105] y, t1are the same or different from each other, selected from C(R3) or N atom, and when y is bonded to other groups, y is selected from C atom;

[0106] t2is selected from O, S, N(Rc ) among any one of the following:

[0107] said R c is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0108] said R3is selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, when there are two or more R3, the two or more R3are the same or different from each other, or adjacent two R3may be connected to each other to form a substituted or unsubstituted ring;

[0109] said c1is selected from 0 or 1.

[0110] Preferably, said L1-L4are the same or different from each other, selected from a single bond or any one of the following groups:

[0111]

[0112] said R3are the same or different from each other, selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidene, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, or benzothiophenyl;

[0113] d1 is selected from 0, 1, 2, 3, or 4, d2 is selected from 0, 1, 2, or 3, d3 is selected from 0, 1, or 2, d4 is selected from 0, 1, 2, 3, 4, 5, or 6, d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, d6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, and d7 is selected from 0 or 1.

[0114] Preferably, when B, C, D, H, G are selected from Formula III, L2, L3, L4 connected thereto are not single bond.

[0115] Preferably, B, C, D, F, H, G are the same or different from each other, selected from any one of Formula II-2, Formula III, or the following group:

[0116]

[0117]

[0118] t3 is selected from any one of O, S, N(R d );

[0119] R d is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0120] R4 is the same or different from each other, selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or the following group substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidene, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, or benzothiophenyl;

[0121] said e1 is selected from 0, 1, 2, 3, 4, or 5, said e2 is selected from 0, 1, 2, 3, or 4, said e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, said e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, said e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, said e6 is selected from 0, 1, 2, or 3, said e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, said e8 is selected from 0, 1, 2, 3, 4, 5, or 6, said e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said e 10 said e1 is selected from 0, 1, 2, 3, 4, or 5, said e2 is selected from 0, 1, 2, 3, or 4, said e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, said e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, said e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, said e6 is selected from 0, 1, 2, or 3, said e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, said e8 is selected from 0, 1, 2, 3, 4, 5, or 6, said e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said e 11 said e1 is selected from 0, 1, 2, 3, 4, or 5, said e2 is selected from 0, 1, 2, 3, or 4, said e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, said e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, said e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, said e6 is selected from 0, 1, 2, or 3, said e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, said e8 is selected from 0, 1, 2, 3, 4, 5, or 6, said e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said e

[0122] Preferably, one or two of B, C, D are selected from

[0123] Preferably, one or two of F, G, H are selected from

[0124] Preferably, R2, R5, R6 are the same or different, selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthridinyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl, or benzothiophenyl.

[0125] Preferably, the nitrogen-containing heterocyclic compound is selected from any one of the following structures:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] The above lists some specific structural forms of the nitrogen-containing heterocyclic compound according to the present application, but the present application is not limited to the listed chemical structures, and any structure based on the structure shown in Chemical Formula I-1 or Chemical Formula I-2, with the substituents being groups as defined above, should be included.

[0167] The present application also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside any one of the anode and the cathode, and the organic layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0168] Preferably, the organic layer according to the present application is located between the anode and the cathode, and comprises at least one of a hole transport region, a light-emitting layer, and an electron transport region, wherein at least one of the hole transport region, the light-emitting layer, and the electron transport region comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0169] Preferably, the hole transport region according to the present application comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0170] Preferably, the hole transport layer according to the present application comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0171] Preferably, the organic layer is located between the anode and the cathode, the organic layer comprises two or more light-emitting portions and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, and the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0172] Preferably, the charge generation layer is composed of an N-type charge generation layer located adjacent to the first light-emitting portion and a P-type charge generation layer located adjacent to the second light-emitting portion, the organic layer comprises the N-type charge generation layer, and the N-type charge generation layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0173] Preferably, the light-emitting layer according to the present application comprises a host material and a dopant material.

[0174] Preferably, the electron transport region according to the present application comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer, and at least one of the electron injection layer, the electron transport layer, and the hole blocking layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0175] Preferably, the electron injection layer according to the present application comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0176] Preferably, the electron transport layer according to the present application comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0177] Preferably, the hole blocking layer according to the present application comprises any one or more of the nitrogen-containing heterocyclic compounds according to the present application.

[0178] Preferably, the organic layer according to the present application is located outside any one of the anode and the cathode, and the organic layer comprises a capping layer.

[0179] The material of each layer of the organic electroluminescent device according to the present application is not particularly limited, and a substance known in the art can be used. The following describes each organic functional layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device, respectively:

[0180] The organic electroluminescent device according to the present application is generally formed on a substrate. The substrate described above can be changed only when an electrode is formed and an organic layer is formed, for example, a substrate of glass, plastic, a polymer film, silicon, or the like.

[0181] The anode material according to the present application preferably uses a material having a high function function to improve the hole injection efficiency. The anode material usable in the present application is selected from the group consisting of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single layer structure or a multi-layer structure including two or more layers, for example, the anode can have a single layer structure of Al or a three layer structure of ITO / Ag / ITO, but is not limited thereto.

[0182] The hole injection layer according to the present application preferably uses a material having a good ability to accept holes. Specific examples of the hole injection layer material usable in the present application can include silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, and the like metal oxides, phthalocyanine compounds, benzidine compounds, phenazine compounds, and the like, but are not limited thereto.

[0183] The hole transport layer material according to the present application preferably has a material having a high hole mobility. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, diphenylamine derivatives, fluorene derivatives, stilbene derivatives, hexacene hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, and the like, but is not limited thereto.

[0184] The light emitting layer material according to the present application includes a host material and a dopant material, and the light emitting layer host material needs to have a bipolar charge transport property and a suitable energy level, and is selected from the group consisting of 4,4'-bis(9-carbazole)diphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)di-9H-carbazole (mCP), 4,4',4"-tris(9-carbazole-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (a-AND), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"' -tetraphenyl]-4,4"-diamine (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), and the like. In addition to the above materials and combinations thereof, the light emitting layer host material can also include other known materials suitable for a light emitting layer, and the like, but is not limited thereto.

[0185] The light emitting layer dopant material of the present application is classified into blue light emitting material, green light emitting material and red light emitting material. The light emitting layer dopant material can be a simple fluorescent material or phosphorescent material, or a combination of fluorescent and phosphorescent material, selected from 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)picolato iridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)anilino]anthracene (TPA), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), etc., but not limited thereto.

[0186] The charge generation layer material of the present application includes n-type charge generation material and p-type charge generation material.

[0187] The n-type charge generation material according to the present application can be selected from one of the following materials or a combination thereof: tris-(8-hydroxyquinolinate) aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-olate) aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), etc., but is not limited thereto. In addition, an auxiliary n-type charge generation material can also be included. For example, the auxiliary n-type charge generation material can be an alkali metal such as Li, Cs, K, Rb, Na, or Fr, etc., but is not limited thereto, or an alkaline earth metal such as Be, Mg, Ca, Sr, Ba, or Ra, etc., a nitrogen-containing heterocyclic compound according to the present application, but is not limited thereto.

[0188] The p-type charge generating material according to the present application can include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalen-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalen-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc., but is not limited thereto.

[0189] The hole blocking layer material according to the present application, which is generally preferred to be a material capable of effectively blocking the hole transport and causing the exciton to be recombined in the light emitting layer rather than in the electron transport layer, can be selected from any one or several of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazaphenanthrene derivatives, azabenzene derivatives, anthrone derivatives, etc., the nitrogen-containing heterocyclic compound according to the present application, but is not limited thereto.

[0190] The electron transport layer material according to the present application is preferably a material having a high electron mobility. It can be selected from any one or several of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), tris(8-hydroxyquinoline)aluminum (III) (Alq3), 8-hydroxyquinoline-lithium (Liq), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum (III) (BAlq), and 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., the nitrogen-containing heterocyclic compound according to the present application, but is not limited thereto.

[0191] The electron injection layer material of the present application, preferably with a small difference in potential barrier with the adjacent organic layer material, specific examples can include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, 8-hydroxyquinoline cesium, 8-hydroxyquinoline aluminum), organic metal salts (metal acetate, metal benzoate or metal stearate), molybdenum trioxide, metal aluminum, etc., the nitrogen-containing heterocyclic compound of the present application, but not limited to this.

[0192] The cathode material of the present application, preferably using a material with a low work function that can promote electron injection into the organic layer to reduce the electron injection barrier. It can be selected from any one or several of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, including their compounds or their mixtures (for example, a mixture of Ag and Mg), but not limited to this.

[0193] The cover layer of the present application is provided on the outside of any one of the anode and the cathode, and preferably uses a material that can improve the internal light coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, double carbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, double amine derivatives, porphyrin derivatives, phthalocyanine derivatives, etc., but not limited to this.

[0194] The thickness of each organic layer of the organic electroluminescent device of the present application is not particularly limited, and the thickness commonly used in the art can be used.

[0195] The organic electroluminescent device of the present application can use any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer printing, electrostatic spraying, slot coating, and dip coating.

[0196] The organic electroluminescent device of the present application can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0197] The organic electroluminescent device of the present application can be widely used in panel display, lighting sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lights, etc.

[0198] The present application provides a preparation method of the compound represented by formula I, which is prepared by a carbon-carbon coupling reaction well known in the art, but the preparation method of the present application is not limited to this, and the structure of formula I can be prepared by the following reaction route:

[0199] Preparation of raw material a, raw material b, and raw material c:

[0200]

[0201] Preparation of Formula I-1 or Formula I-2:

[0202]

[0203] wherein, X a are the same or different from each other, and are selected from any one of Cl, Br, I; the definitions of A, B, C, D, E, F, G, H, L1-L4, x, v, z are the same as above.

[0204] The above substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of the substituents can be changed according to techniques known in the art.

[0205] The present application will be explained in more detail by the following examples, but the present application is not intended to be limited by the examples. Based on the description, one of ordinary skill in the art will be able to implement the present application and prepare other compounds and devices according to the present application within the entire scope disclosed without exerting creative effort.

[0206] Preparation and characterization of compounds

[0207] Explanation of raw materials, reagents, and characterization equipment:

[0208] The raw materials and reagents used in the following examples are not particularly limited in the present application, and can be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and reagents used in the present application are reagent grade.

[0209] Mass spectrometry was performed using a Waters G2-Si quadrupole time-of-flight high-resolution mass spectrometer in the United Kingdom, with chloroform as the solvent;

[0210] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar, Germany, with a sample mass of 5-10 mg;

[0211] Synthesis Example 1: Synthesis of raw material b-98

[0212]

[0213] Preparation of raw material b-98:

[0214] Into a reaction flask was placed m-98 (44.14 g, 120 mmol), d-2 (30.47 g, 120 mmol), KOAc (23.55 g, 240 mmol), then 550 mL of DMF solution was added, after nitrogen was replaced for air for 3 times, Pd(dppf)Cl2(0.88 g, 1.20 mmol) was added, the reaction was heated and stirred for 8 h, after the reaction was completed, the reaction was cooled to room temperature, distilled water was added, extracted with ethyl acetate (600 mL x 3 times), the organic phase was separated, the organic phase was dried over anhydrous magnesium sulfate, the obtained solid was recrystallized and purified with n-hexane: ethyl acetate = 9: 1 (v / v) to obtain intermediate b-98 (49.61 g, yield 90%), HPLC purity ≧ 99.83%, mass spectrum m / z: 459.2129 (theoretical value: 459.2118).

[0215] The starting materials were replaced accordingly, and the preparation method of intermediate b-98 in synthesis example 1 was followed to prepare intermediate b / c, and the starting materials were as shown in the following table:

[0216]

[0217]

[0218] Synthesis Example 2: Synthesis of compound 53

[0219]

[0220] Preparation of intermediate I-53:

[0221] Under nitrogen protection, g-53 (31.73 g, 100 mmol), a-53 (19.41 g, 100 mmol), KOAc (19.63 g, 200.00 mmol) were added into 650 ml of tetrahydrofuran and 160 ml of distilled water, Pd(dppf)Cl2(0.73 g, 1.00 mmol) was added under stirring, the mixture solution of the above reaction was heated to reflux for 4.0 h, after the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, separated by standing, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by reduced pressure distillation, crystallized by cooling, filtered, the obtained solid was recrystallized with ethyl acetate to obtain intermediate I-53 (27.18 g, 80%), HPLC purity ≧ 99.83%. Mass spectrum m / z: 337.9881 (theoretical value: 337.9893).

[0222] Preparation of intermediate II-53:

[0223] Under nitrogen protection, I-53 (20.38 g, 60.00 mmol), b-53 (26.12 g, 60.00 mmol), KOAc (9.18 g, 100 mmol) were added into 400 ml tetrahydrofuran and 100 ml distilled water, Pd(OAc)2(0.13 g, 0.60 mmol) was added under stirring, the mixed solution of the above reaction was heated to reflux for 3.0 h, after the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, separated by standing, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by reduced pressure distillation, crystallized by cooling, the obtained solid was recrystallized with ethyl acetate to obtain intermediate II-53 (24.89 g, 73%), HPLC purity≧99.87%. Mass spectrum m / z: 567.1887 (theoretical value: 567.1898).

[0224] Preparation of compound 53:

[0225] Under nitrogen protection, II-53 (11.36 g, 20.00 mmol), c-53 (7.05 g, 22.00 mmol), K2CO3(5.53 g, 40.00 mmol) were added into 240 ml tetrahydrofuran and 60 ml distilled water, Pd(PPh3)4(0.23 g, 0.20 mmol) was added under stirring, the mixed solution of the above reaction was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, separated by standing, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by reduced pressure distillation, crystallized by cooling, filtered, the obtained solid was recrystallized with toluene to obtain compound 53 (10.16 g, 70%), HPLC purity≧99.95%. Mass spectrum m / z: 725.3243 (theoretical value: 725.3226). Theoretical elemental content (%) 51 H 43 N3Si: C, 84.37; H, 5.97; N, 5.79. Found elemental content (%): C, 84.40; H, 5.95; N, 5.82.

[0226] Synthesis example 3: synthesis of compound 74

[0227]

[0228] According to the same preparation method of synthesis example 2, g-53 was replaced by equimolar g-74, b-53 was replaced by equimolar b-74, c-53 was replaced by equimolar c-74 to obtain compound 74 (12.25 g), HPLC solid purity≧99.92. Mass spectrum m / z: 913.3473 (theoretical value: 913.3488). Theoretical elemental content (%) 65 H47 N3OSi: C, 85.40; H, 5.18; N, 4.60. Found (%,): C, 85.37; H, 5.21; N, 4.57.

[0229] Synthesis Example 4: Synthesis of compound 98

[0230]

[0231] Following the same preparation method as in synthesis example 2, g-53 was replaced with equimolar of g-98, b-53 was replaced with equimolar of b-98, c-53 was replaced with equimolar of c-98, compound 98 (9.84 g) was obtained with solid purity > 99.90 by HPLC. Mass m / z: 756.3651 (theoretical value: 756.3666). Theoretical elemental content (%) C 53 H 36 N3OSi: C, 83.10; H, 5.66; N, 5.49. Found (%,): C, 83.07; H, 5.63; N, 5.52.

[0232] Synthesis Example 5: Synthesis of compound 104

[0233]

[0234] Following the same preparation method as in synthesis example 2, b-53 was replaced with equimolar of b-104, c-53 was replaced with equimolar of c-104, compound 104 (9.65 g) was obtained with solid purity > 99.91 by HPLC. Mass m / z: 765.3187 (theoretical value: 765.3175). Theoretical elemental content (%) C 53 H 43 N3OSi: C, 83.10; H, 5.66; N, 5.49. Found (%,): C, 83.07; H, 5.63; N, 5.52.

[0235] Synthesis Example 6: Synthesis of compound 111

[0236]

[0237] Following the same preparation method as in synthesis example 2, b-53 was replaced with equimolar of b-111, c-53 was replaced with equimolar of c-111, compound 111 (11.30 g) was obtained with solid purity > 99.94 by HPLC. Mass m / z: 773.3213 (theoretical value: 773.3226). Theoretical elemental content (%) C 55 H 43N3Si: C, 85.34; H, 5.60; N, 5.43. Found (mass %): C, 85.31; H, 5.57; N, 5.47.

[0238] Synthesis Example 7: Synthesis of compound 118

[0239]

[0240] Following the same preparation method as in synthesis example 2, a-53 was replaced with an equivalent molar of a-118, b-53 was replaced with an equivalent molar of b-118, and c-53 was replaced with an equivalent molar of c-118 to obtain compound 118 (10.97 g) with a solid purity > 99.93 by HPLC. Mass m / z: 944.4291 (theoretical value: 944.4274). Theoretical elemental content (%) C 67 H 56 N4Si: C, 85.13; H, 5.97; N, 5.93. Found (mass %): C, 85.17; H, 5.95; N, 5.89.

[0241] Synthesis Example 8: Synthesis of compound 155

[0242]

[0243] Following the same preparation method as in synthesis example 2, b-53 was replaced with an equivalent molar of b-155, and c-53 was replaced with an equivalent molar of c-111 to obtain compound 155 (11.68) with a solid purity > 99.96 by HPLC. Mass m / z: 845.3633 (theoretical value: 845.3622). Theoretical elemental content (%) C 58 H 51 N3Si2: C, 82.32; H, 6.07; N, 4.97. Found (mass %): C, 82.30; H, 6.10; N, 4.93.

[0244] Synthesis Example 9: Synthesis of compound 202

[0245]

[0246] Following the same preparation method as in synthesis example 2, b-53 was replaced with an equivalent molar of b-202, and c-53 was replaced with an equivalent molar of c-111 to obtain compound 202 (11.22 g) with a solid purity > 99.93 by HPLC. Mass m / z: 778.3556 (theoretical value: 778.3540). Theoretical elemental content (%) C 55 H 38D5N3Si: C, 84.79; H, 6.21; N, 5.39. Found (mass %): C, 84.81; H, 6.18; N, 5.43.

[0247] Synthesis Example 10: Synthesis of compound 230

[0248]

[0249] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-230, a-53 was replaced with an equivalent molar of a-230, b-53 was replaced with an equivalent molar of b-111, and c-1 was replaced with an equivalent molar of c-111 to obtain compound 230 (12.24 g) with a solid purity of > 99.97% as determined by HPLC. Mass m / z: 849.3548 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H 47 N3Si: C, 86.18; H, 5.57; N, 4.94. Found (mass %): C, 86.22; H, 5.60; N, 4.91.

[0250] Synthesis Example 11: Synthesis of compound 244

[0251]

[0252] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-244, b-53 was replaced with an equivalent molar of b-111, and c-53 was replaced with an equivalent molar of c-244 to obtain compound 244 (12.29 g) with a solid purity of > 99.93% as determined by HPLC. Mass m / z: 829.3838 (theoretical value: 829.3852). Theoretical elemental content (%) C 59 H 51 N3Si: C, 85.36; H, 6.19; N, 5.06. Found (mass %): C, 85.32; H, 6.21; N, 5.11.

[0253] Synthesis Example 12: Synthesis of compound 317

[0254]

[0255] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-317, and c-53 was replaced with an equivalent molar of c-111 to obtain compound 317 (12.41 g) with a solid purity of > 99.95% as determined by HPLC. Mass m / z: 849.3550 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H47 N3Si: C, 86.18; H, 5.57; N, 4.94. Found (mass %): C, 86.20; H, 5.61; N, 4.90.

[0256] Synthesis Example 13: Synthesis of compound 352

[0257]

[0258] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-317, c-53 was replaced with an equivalent molar of c-352, to obtain compound 352 (11.63 g) with solid purity > 99.93 by HPLC. Mass m / z: 854.3870 (theoretical value: 854.3853). Theoretical elemental content (%) C 61 H 42 N3Si: C, 86.18; H, 5.57; N, 4.94. Found (mass %): C, 86.20; H, 5.61; N, 4.90.

[0259] Synthesis Example 14: Synthesis of compound 369

[0260]

[0261] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-317, c-53 was replaced with an equivalent molar of c-369, to obtain compound 369 (12.44 g) with solid purity > 99.98 by HPLC. Mass m / z: 863.3680 (theoretical value: 863.3696). Theoretical elemental content (%) C 62 H 49 N3Si: C, 86.18; H, 5.57; N, 4.94. Found (mass %): C, 86.20; H, 5.61; N, 4.90.

[0262] Synthesis Example 15: Synthesis of compound 473

[0263]

[0264] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-244, b-53 was replaced with an equivalent molar of b-317, c-53 was replaced with an equivalent molar of c-111, to obtain compound 473 (12.07 g) with solid purity > 99.93 by HPLC. Mass m / z: 849.3552 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H 47N3Si: C, 85.57; H, 6.50; N, 4.75. Found: C, 85.60; H, 6.48; N, 4.78.

[0265] Synthesis Example 16: Synthesis of compound 646

[0266]

[0267] Following the same preparation method as in synthesis example 2, b-53 was replaced with equimolar of b-111, c-53 was replaced with equimolar of c-646, compound 646 (12.20 g) was obtained with solid purity > 99.92 by HPLC. Mass m / z: 883.4337 (theoretical value: 883.4322). Theoretical elemental content (%) C 63 H 57 N3Si: C, 85.57; H, 6.50; N, 4.75. Found: C, 85.60; H, 6.48; N, 4.78.

[0268] Synthesis Example 17: Synthesis of compound 719

[0269]

[0270] Following the same preparation method as in synthesis example 2, b-53 was replaced with equimolar of b-719, c-53 was replaced with equimolar of c-719, compound 719 (12.11 g) was obtained with solid purity > 99.96 by HPLC. Mass m / z: 852.3681 (theoretical value: 852.3697). Theoretical elemental content (%) C 61 H 40 N3Si: C, 85.57; H, 6.50; N, 4.75. Found: C, 85.60; H, 6.48; N, 4.78.

[0271] Synthesis Example 18: Synthesis of compound 743

[0272]

[0273] Following the same preparation method as in synthesis example 2, b-53 was replaced with equimolar of b-743, c-53 was replaced with equimolar of c-743, compound 743 (11.60 g) was obtained with solid purity > 99.91 by HPLC. Mass m / z: 852.3678 (theoretical value: 852.3697). Theoretical elemental content (%) C 61 H 40D5N3Si: C, 86.39; H, 5.35; N, 4.95. Found: C, 86.42; H, 5.36; N, 4.92.

[0274] Synthesis Example 19: Synthesis of compound 748

[0275]

[0276] Following the same preparation method as in synthesis example 2, replace g-53 with equimolar of g-230, b-53 with equimolar of b-317, c-53 with equimolar of c-719, to obtain compound 748 (11.70 g) with solid purity > 99.95% by HPLC. Mass m / z: 847.3371 (theoretical value: 847.3383). Theoretical elemental content (%) C 61 H 45 N3Si: C, 86.39; H, 5.35; N, 4.95. Found: C, 86.42; H, 5.36; N, 4.92.

[0277] Synthesis Example 20: Synthesis of compound 801

[0278]

[0279] Following the same preparation method as in synthesis example 2, replace b-53 with equimolar of b-801, c-53 with equimolar of c-801, to obtain compound 801 (11.73 g) with solid purity > 99.90% by HPLC. Mass m / z: 849.3551 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H 47 N3Si: C, 86.39; H, 5.35; N, 4.95. Found: C, 86.42; H, 5.36; N, 4.92.

[0280] Synthesis Example 21: Synthesis of compound 843

[0281]

[0282] Following the same preparation method as in synthesis example 2, replace a-53 with equimolar of a-843, b-53 with equimolar of b-843, c-53 with equimolar of c-843, to obtain compound 843 (12.89 g) with solid purity > 99.93% by HPLC. Mass m / z: 960.4850 (theoretical value: 960.4839). Theoretical elemental content (%) C 70 H 64N2Si: C, 84.47; H, 5.20; N, 3.28. Found: C, 84.50; H, 5.18; N, 3.31.

[0283] Synthesis Example 22: Synthesis of compound 892

[0284]

[0285] Following the same preparation method as in synthesis example 2, replace b-53 with equimolar of b-892, c-53 with equimolar of c-892, to obtain compound 892 (11.60 g) with solid purity > 99.90 by HPLC. Mass spectrum m / z: 852.2980 (calcd 852.2994). Theoretical elemental content (%) C 60 H 44 N2Si: C, 84.47; H, 5.20; N, 3.28. Found: C, 84.50; H, 5.18; N, 3.31.

[0286] Synthesis Example 23: Synthesis of compound 933

[0287]

[0288] Following the same preparation method as in synthesis example 2, replace g-53 with equimolar of g-74, a-53 with equimolar of a-933, b-53 with equimolar of b-155, c-53 with equimolar of c-933, to obtain compound 933 (11.03 g) with solid purity > 99.94 by HPLC. Mass spectrum m / z: 787.3370 (calcd 787.3383). Theoretical elemental content (%) C 56 H 45 N3Si: C, 85.35; H, 5.76; N, 5.33. Found: C, 85.34; H, 5.78; N, 5.29.

[0289] Synthesis Example 24: Synthesis of compound 936

[0290]

[0291] Following the same preparation method as in synthesis example 2, replace g-53 with equimolar of g-230, a-53 with equimolar of a-933, b-53 with equimolar of b-936, c-53 with equimolar of c-936, to obtain compound 936 (11.47 g) with solid purity > 99.92 by HPLC. Mass spectrum m / z: 842.3521 (calcd 842.3513). Theoretical elemental content (%) C59 H 50 N2Si2: C, 84.04; H, 5.98; N, 3.32. Found (%,): C, 84.07; H, 5.95; N, 3.29.

[0292] Synthesis Example 25: Synthesis of compound 939

[0293]

[0294] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with equimolar of g-939, b-53 was replaced with equimolar of b-939, and c-53 was replaced with equimolar of c-939 to obtain compound 939 (11.08 g) with solid purity > 99.90 by HPLC. Mass spectrum m / z: 826.3730 (theoretical value: 826.3743). Theoretical elemental content (%) C 60 H 50 N2Si: C, 87.12; H, 6.09; N, 3.39. Found elemental content (%) C, 87.08; H, 6.12; N, 3.41.

[0295] Synthesis Example 26: Synthesis of compound 965

[0296]

[0297] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with equimolar of b-317, and c-53 was replaced with equimolar of c-965 to obtain compound 965 (10.96 g) with solid purity > 99.97 by HPLC. Mass spectrum m / z: 817.3870 (theoretical value: 817.3852). Theoretical elemental content (%) C 58 H 51 N3Si: C, 85.15; H, 6.28; N, 5.14. Found elemental content (%) C, 85.17; H, 6.30; N, 5.17.

[0298] Synthesis Example 27: Synthesis of compound 982

[0299]

[0300] Following the same preparation method as in Synthesis Example 2, replace g-53 with equimolar of g-74, b-53 with equimolar of b-994, and c-53 with equimolar of c-994 to obtain compound 994 (10.56 g) with solid purity > 99.93 by HPLC. Mass m / z: 775.4179 (calcd 775.4167). Theoretical elemental content (%) C 60 H 52 N4Si: C, 84.07; H, 6.11; N, 6.54. Found elemental content (%) C, 84.10; H, 6.09; N, 6.51.

[0301] Synthesis Example 28: Synthesis of compound 994

[0302]

[0303] Following the same preparation method as in Synthesis Example 2, replace g-53 with equimolar of g-74, b-53 with equimolar of b-994, and c-53 with equimolar of c-994 to obtain compound 994 (10.56 g) with solid purity > 99.93 by HPLC. Mass m / z: 775.4179 (calcd 775.4167). Theoretical elemental content (%) C 54 H 37 D 10 N3Si: C, 83.57; H, 7.40; N, 5.41. Found elemental content (%) C, 83.60; H, 7.38; N, 5.39.

[0304] Synthesis Example 29: Synthesis of compound 1027

[0305]

[0306] Following the same preparation method as in Synthesis Example 2, replace g-53 with equimolar of g-74, b-53 with equimolar of b-994, and c-53 with equimolar of c-994 to obtain compound 994 (10.56 g) with solid purity > 99.93 by HPLC. Mass m / z: 775.4179 (calcd 775.4167). Theoretical elemental content (%) C 58 H 49 N3Si2: C, 82.52; H, 5.85; N, 4.98. Found elemental content (%) C, 82.49; H, 5.87; N, 4.99.

[0307] Synthesis Example 30: Synthesis of compound 1067

[0308]

[0309] Following the same preparation procedure as in Synthesis Example 2, replacing g-53 with equimolar of g-230, a-53 with equimolar of a-933, b-53 with equimolar of b-155, c-53 with equimolar of c-1067, compound 1067 (10.87 g) was obtained with solid purity > 99.96% by HPLC. Mass m / z: 787.3030 (calcd 787.3019). Anal. Calcd for C 55 H 41 N3OSi: C, 83.83; H, 5.24; N, 5.33. Found: C, 83.79; H, 5.26; N, 5.30.

[0310] Synthesis Example 31: Synthesis of compound 1080

[0311]

[0312] Following the same preparation procedure as in Synthesis Example 2, replacing g-53 with equimolar of g-244, a-53 with equimolar of a-1080, b-53 with equimolar of b-1080, c-53 with equimolar of c-1080, compound 1080 (12.95 g) was obtained with solid purity > 99.90% by HPLC. Mass m / z: 980.3929 (calcd 980.3910). Anal. Calcd for C 69 H 52 N4OSi: C, 84.46; H, 5.34; N, 5.71. Found: C, 84.43; H, 5.36; N, 5.69.

[0313] Synthesis Example 32: Synthesis of compound 1081

[0314]

[0315] Following the same preparation procedure as in Synthesis Example 2, replacing a-53 with equimolar of a-933, b-53 with equimolar of b-155, c-53 with equimolar of c-111, compound 1081 (11.15 g) was obtained with solid purity > 99.94% by HPLC. Mass m / z: 773.3241 (calcd 773.3226). Anal. Calcd for C 55 H 43 N3Si: C, 85.34; H, 5.60; N, 5.43. Found: C, 88.36; H, 5.58; N, 5.41.

[0316] Synthesis Example 33: Synthesis of compound 1236

[0317]

[0318] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-230, a-53 was replaced with an equivalent molar of a-933, b-53 was replaced with an equivalent molar of b-155, and c-53 was replaced with an equivalent molar of c-1236 to obtain compound 1236 (11.62 g) with a solid purity > 99.92 by HPLC. Mass spectrum m / z: 853.3781 (calcd 853.3790). Theoretical elemental content (%) C 61 H 43 D4N3Si: C, 85.78; H, 6.02; N, 4.92. Found elemental content (%) C, 85.80; H, 6.04; N, 4.89.

[0319] Synthesis Example 34: Synthesis of compound 1244

[0320]

[0321] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-230, a-53 was replaced with an equivalent molar of a-933, b-53 was replaced with an equivalent molar of b-155, and c-53 was replaced with an equivalent molar of c-719 to obtain compound 1244 (10.81 g) with a solid purity > 99.98 by HPLC. Mass spectrum m / z: 771.3055 (calcd 771.3070). Theoretical elemental content (%) C 55 H 41 N3Si: C, 85.57; H, 5.35; N, 5.44. Found elemental content (%) C, 85.61; H, 5.33; N, 5.42.

[0322] Synthesis Example 35: Synthesis of compound 1253

[0323]

[0324] Following the same preparation method as in Synthesis Example 2, a-53 was replaced with an equivalent molar of a-1253, b-53 was replaced with an equivalent molar of b-155, and c-53 was replaced with an equivalent molar of c-1253 to obtain compound 1253 (12.21 g) with a solid purity > 99.93 by HPLC. Mass spectrum m / z: 847.3372 (calcd 847.3383). Theoretical elemental content (%) C 61 H 45N3Si: C, 85.34; H, 5.60; N, 5.43. Found (wt%): C, 85.31; H, 5.58; N, 5.47.

[0325] Synthesis Example 36: Synthesis of compound 1262

[0326]

[0327] Following the same preparation method as in Synthesis Example 2, a-53 was replaced with an equivalent molar of a-1262, b-53 was replaced with an equivalent molar of b-155, and c-53 was replaced with an equivalent molar of c-1262 to give compound 1262 (11.08 g) with solid purity > 99.95% by HPLC. Mass spectrum m / z: 826.3558 (theoretical value: 826.3540). Theoretical elemental content (%) C 59 H 38 N3Si: C, 85.34; H, 5.60; N, 5.43. Found (wt%): C, 85.31; H, 5.58; N, 5.47.

[0328] Synthesis Example 37: Synthesis of compound 1324

[0329]

[0330] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-1324, and c-53 was replaced with an equivalent molar of c-1324 to give compound 1324 (11.15 g) with solid purity > 99.92% by HPLC. Mass spectrum m / z: 773.3240 (theoretical value: 773.3226). Theoretical elemental content (%) C 55 H 43 N3Si: 85.34; H, 5.60; N, 5.43. Found (wt%): 85.31; H, 5.58; N, 5.47.

[0331] Synthesis Example 38: Synthesis of compound 1330

[0332]

[0333] Following the same preparation method as in Synthesis Example 2, a-53 was replaced with an equivalent molar of a-1330, b-53 was replaced with an equivalent molar of b-1330, and c-53 was replaced with an equivalent molar of c-1330 to give compound 1330 (13.38 g) with solid purity > 99.91% by HPLC. Mass spectrum m / z: 997.4238 (theoretical value: 997.4248). Theoretical elemental content (%) C 70 H 59N3Si2: C, 84.21 ; H, 5.96; N, 4.21. Found ( % ) : C, 84.19; H, 5.98; N, 4.18.

[0334] Synthesis Example 39: Synthesis of compound 1331

[0335]

[0336] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-1331, c-53 was replaced with an equivalent molar of c-1331, to give compound 1331 (11.89 g) with solid purity > 99.93 by HPLC. Mass spectrum m / z: 849.3528 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H 47 N3Si: C, 86.18; H, 5.57; N, 4.94. Found elemental content (%) : C, 86.22; H, 5.60; N, 4.90.

[0337] Synthesis Example 40: Synthesis of compound 1363

[0338]

[0339] Following the same preparation method as in Synthesis Example 2, b-53 was replaced with an equivalent molar of b-1363, c-53 was replaced with an equivalent molar of c-1324, to give compound 1363 (11.73 g) with solid purity > 99.92 by HPLC. Mass spectrum m / z: 849.3527 (theoretical value: 849.3539). Theoretical elemental content (%) C 61 H 47 N3Si: C, 86.18; H, 5.57; N, 4.94. Found elemental content (%) : C, 86.22; H, 5.60; N, 4.90.

[0340] Synthesis Example 41: Synthesis of compound 1369

[0341]

[0342] Following the same preparation method as in Synthesis Example 2, g-53 was replaced with an equivalent molar of g-244, b-53 was replaced with an equivalent molar of b-1324, c-53 was replaced with an equivalent molar of c-1324, to give compound 1369 (10.84 g) with solid purity > 99.96 by HPLC. Mass spectrum m / z: 773.3239 (theoretical value: 773.3226). Theoretical elemental content (%) C 55 H 43N3Si: C, 86.88; H, 5.55; N, 4.54. Found (%): C, 86.90; H, 5.57; N, 4.51.

[0343] Synthesis Example 42: Synthesis of compound 1375

[0344]

[0345] According to the same preparation method of synthesis example 2, g-53 is replaced by equimolar g-1375, a-53 is replaced by equimolar a-1375, b-53 is replaced by equimolar b-1375, c-53 is replaced by equimolar c-1324, compound 1375 (12.60 g) is obtained, and the solid purity is ≧99.92% detected by HPLC. Mass spectrum m / z: 925.3837 (theoretical value: 925.3852). Theoretical elemental content (%) C 67 H 51 N3Si: C, 86.88; H, 5.55; N, 4.54. Found (%): C, 86.90; H, 5.57; N, 4.51.

[0346] Synthesis Example 43: Synthesis of compound 1390

[0347]

[0348] According to the same preparation method of synthesis example 2, g-53 is replaced by equimolar g-1390, a-53 is replaced by equimolar a-1390, b-53 is replaced by equimolar b-155, c-53 is replaced by equimolar c-1390, compound 1390 (10.79 g) is obtained, and the solid purity is ≧99.90% detected by HPLC. Mass spectrum m / z: 898.3475 (theoretical value: 898.3492). Theoretical elemental content (%) C 64 H 46 N4Si: C, 85.49; H, 5.16; N, 6.23. Found (%): C, 85.49; H, 5.16; N, 6.23.

[0349] [Device Example 1]

[0350] First, the ITO / Ag / ITO substrate is cleaned with ultrasonic cleaning in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, isopropyl alcohol, acetone, methanol and other solvents are used for ultrasonic cleaning in turn, each time for 10 minutes. After cleaning, it is dried at 120°C.

[0351] An organic electroluminescence device was produced by sequentially depositing a hole injection layer HI-1 (60 nm); a hole transport layer HT-1 (110 nm); a light emitting layer RH-1:RH-2:RD = 49:49:2 (mass ratio, 35 nm); an electron transport layer compound 53:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1.0 nm); a cathode Mg:Ag = 1:9 (mass ratio, 11 nm); and a cover layer CP-1 (80 nm) on a cleaned ITO / Ag / ITO substrate by vacuum deposition.

[0352]

[0353] [Device Example 2-42]

[0354] An organic electroluminescence device was produced by replacing compound 53 in Device Example 1 with compound 53, compound 74, compound 98, compound 104, compound 111, compound 118, compound 155, compound 202, compound 230, compound 244, compound 317, compound 352, compound 369, compound 473, compound 646, compound 719, compound 743, compound 748, compound 801, compound 843, compound 892, compound 933, compound 936, compound 939, compound 965, compound 982, compound 994, compound 1027, compound 1067, compound 1080, compound 1081, compound 1236, compound 1244, compound 1253, compound 1262, compound 1324, compound 1330, compound 1331, compound 1363, compound 1369, compound 1375, or compound 1390 as an electron transport layer material, respectively, and otherwise in the same manner as in Device Example 1.

[0355] [Comparative Device Examples 1-5]

[0356] An organic electroluminescence device was produced by replacing compound 53 in Device Example 1 with comparative compound 1, comparative compound 2, comparative compound 3, comparative compound 4, or comparative compound 5 as an electron transport layer material, respectively, and otherwise in the same manner as in Device Example 1.

[0357] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter produced by Keithley Corporation, USA, and a PR788 spectral scanning luminance meter by Photo Research Corporation, USA was used to test the luminous efficiency of the organic electroluminescence device. The lifetime test was performed using an M6000 OLED lifetime test system by McScience Corporation. The test environment was an atmospheric environment, and the temperature was room temperature.

[0358] The luminescent characteristics of the organic electroluminescent devices of device embodiments 1-42 and comparative examples 1-5 of the present application are shown in Table 1 below.

[0359]

[0360]

[0361] From the data in Table 1, it can be seen that the nitrogen-containing heterocyclic compound of Formula I of the present application applied to the organic electroluminescent device as the electron transport layer material has good electron transport capacity, can balance the transport of carriers, increase the recombination probability of excitons in the light-emitting layer, and effectively improve the luminous efficiency and service life of the device.

[0362] [Device embodiment 43]

[0363] First, the ITO / Ag / ITO substrate was ultrasonically cleaned in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, isopropyl alcohol, acetone, methanol and other solvents were used for ultrasonic cleaning, each time for 10 minutes. After cleaning, the substrate was dried at 120°C.

[0364] A vacuum evaporation method was used to evaporate the hole injection layer HI-1 (60 nm), the hole transport layer HT-1 (100 nm), the light-emitting layer GH-1:GH-2:GD = 46:46:8 (mass ratio, 40 nm), the hole blocking layer compound 53 (10 nm), the electron transport layer ET:Liq = 1:1 (mass ratio, 30 nm), the electron injection layer LiF (0.8 nm), the cathode Mg:Ag = 1:9 (mass ratio, 12 nm), and the cover layer CP-1 (80 nm) on the cleaned ITO / Ag / ITO substrate in sequence, thereby preparing an organic electroluminescent device.

[0365]

[0366] [Device embodiments 44-84]

[0367] An organic electroluminescence device is produced in the same manner as in Device Example 43, except that Compound 53 in Device Example 43 is replaced with Compound 53, Compound 74, Compound 98, Compound 104, Compound 111, Compound 118, Compound 155, Compound 202, Compound 230, Compound 244, Compound 317, Compound 352, Compound 369, Compound 473, Compound 646, Compound 719, Compound 743, Compound 748, Compound 801, Compound 843, Compound 892, Compound 933, Compound 936, Compound 939, Compound 965, Compound 982, Compound 994, Compound 1027, Compound 1067, Compound 1080, Compound 1081, Compound 1236, Compound 1244, Compound 1253, Compound 1262, Compound 1324, Compound 1330, Compound 1331, Compound 1363, Compound 1369, Compound 1375, or Compound 1390, respectively, as the electron transport layer material.

[0368] [Comparative Device Examples 6 to 10]

[0369] An organic electroluminescence device is produced in the same manner as in Device Example 43, except that Compound 53 in Device Example 43 is replaced with Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, or Comparative Compound 5, respectively, as the hole blocking layer material.

[0370] The results of the luminescence characteristics test of the organic electroluminescence devices obtained in Device Examples 43 to 84 and Comparative Examples 6 to 10 of the present application are shown in Table 2 below.

[0371]

[0372]

[0373] As can be seen from the data in Table 2, the nitrogen-containing heterocyclic compound represented by Formula I of the present application, when used as the hole blocking layer material in the organic electroluminescence device, has good electron transport ability, and can effectively block holes in the light-emitting layer, avoid the recombination of holes and electrons outside the light-emitting layer, increase the recombination probability of excitons in the light-emitting layer, and effectively improve the luminous efficiency and service life of the device.

[0374] It should be noted that the present application is described in particular with individual embodiments, but those skilled in the art can make various forms or details of improvements to the present application without departing from the principles of the present application, and these improvements also fall within the scope of protection of the present application.

Claims

1. A nitrogen-containing heterocyclic compound, characterized by, The nitrogen-containing heterocyclic compound has a structure as shown below, In formula I-1, the x, v are the same as or different from each other, selected from C(R2) or N atom, and at least one of the v is selected from N atom, when the x or v is bonded with other groups, the x or v is selected from C atom; The A is selected from the group shown in formula II-2; In formula I-2, the z is the same as or different from each other, selected from C(R5) or N atom, and at least one of the z is selected from N atom, when the z is bonded with other groups, the z is selected from C atom; The E is selected from the group shown in formula II-1; The B, C, D, F, H, G are the same as or different from each other, selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, and at least one of the B, C and D in formula I-1 is selected from the group shown in formula III, and at least one of the H and G in formula I-2 is selected from the group shown in formula III; The a is the same as or different from each other, selected from CH or N atom, when the a is bonded with other groups, the a is selected from C atom; said R a , R b are the same or different from each other, and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or any one of said R a , R b may be connected to each other to form a substituted or unsubstituted ring; or any one of R a , R b may be directly bonded to L1; said R m , R n are the same or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C2 to C25 alkenyl, substituted or unsubstituted C3 to C25 cycloalkyl, substituted or unsubstituted C3 to C25 silyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted fused ring group of C6 to C30 aromatic ring and C3 to C30 aliphatic ring, substituted or unsubstituted C2 to C30 heteroaryl; or any one of said R m , R n may be linked to each other to form a substituted or unsubstituted ring; or any one of R m , R n may be directly bonded to L1; The R is the same as or different from each other, selected from any one of hydrogen, deuterium, fluorine, trifluoromethyl, cyano, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C25 cycloalkyl; The R1, R2, R5, R6 are the same as or different from each other, selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, when there are two or more R2, R5, the two or more R2, R5 are the same as or different from each other, or adjacent two R2, R5 can be connected to each other to form a substituted or unsubstituted ring; The m is selected from 0, 1, 2, 3, 4, 5, 6 or 7, when there are two or more R1, the two or more R1 are the same as or different from each other, or adjacent two R1 can be connected to each other to form a substituted or unsubstituted ring; The n is selected from 0, 1, 2 or 3, when there are two or more R6, the two or more R6 are the same as or different from each other, or adjacent two R6 can be connected to each other to form a substituted or unsubstituted ring; The L1-L4 are the same as or different from each other, selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroarylene, and combinations thereof.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized by The formula II-1 is selected from any one of the groups shown below; the a are the same or different from each other, selected from CH or N atom, when a is bonded with other groups, the a is selected from C atom; said Y is selected from O, S, C(R x R y ), N(R z ) any one of them; the ring A is selected from substituted or unsubstituted C3-C10 aliphatic ring; said R m , R n are the same or different from each other and are selected from the group consisting of hydrogen, deuterium, cyano, nitro, halogen or any one of the following groups which are unsubstituted or substituted by one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, adamantanyl, norbornanyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidyl, pyrazyl, pyridazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl or benzothiophenyl; the a1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the a2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said R x , R y , each other same or different, is selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C6-C30 aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl, or said R x , R y may be connected to each other to form a substituted or unsubstituted ring; The R z Selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, or said R z It can be directly bonded to L1; The L m is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused ring group, a substituted or unsubstituted C2-C30 heteroarylene, and a combination thereof.

3. The nitrogen-containing heterocyclic compound according to claim 1, wherein the formula II-2 is selected from formula II-1 or any one of the following groups: the a are the same or different from each other, selected from CH or N atom, when a is bonded with other groups, the a is selected from C atom; the R1 are the same or different from each other, selected from hydrogen, deuterium, cyano, nitro, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidene, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl or benzothiophenyl; the f1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the f2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the f3 is selected from 0, 1, 2, 3 or 4, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

4. The nitrogen-containing heterocyclic compound according to claim 1, wherein said group of formula III is selected from any one of the following groups:

5. The nitrogen-containing heterocyclic compound according to claim 1, wherein the L1-L4 are the same or different from each other, selected from single bond or any one of the following groups and combinations thereof: the y, t1 are the same or different from each other, selected from C(R3) or N atom, when y is bonded with other groups, the y is selected from C atom; said t2is selected from any one of O, S, N(R c ) ; R is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C3-C25silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C6-C30aromatic ring fused with C3-C30aliphatic ring, substituted or unsubstituted C2-C30heteroaryl; c R is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C3-C25silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C6-C30aromatic ring fused with C3-C30aliphatic ring, substituted or unsubstituted C2-C30heteroaryl; the R3 is selected from hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, when there are two or more R3, the two or more R3 are the same or different from each other, or adjacent two R3 can be connected to each other to form a substituted or unsubstituted ring; the R1 are the same or different from each other, selected from hydrogen, deuterium, cyano, nitro, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidene, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl or benzothiophenyl; the f1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the f2 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the f3 is selected from 0, 1, 2, 3 or 4, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, the f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the f6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, the f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12. the L1-L4 are the same or different from each other, selected from single bond or any one of the following groups and combinations thereof: the y, t1 are the same or different from each other, selected from C(R3) or N atom, when y is bonded with other groups, the y is selected from C atom; the R3 is selected from hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl, when there are two or more R3, the two or more R3 are the same or different from each other, or adjacent two R3 can be connected to each other to form a substituted or unsubstituted ring; said c1 is selected from 0 or 1.

6. The nitrogen-containing heterocyclic compound according to claim 1, wherein said B, C, D, F, H, G are the same or different from each other, selected from any one of Formula II-2, Formula III or the following groups: said t3is selected from any one of O, S, N(R d ) ; R is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C3-C25silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C6-C30aromatic ring fused with C3-C30aliphatic ring, substituted or unsubstituted C2-C30heteroaryl; d R is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C25alkyl, substituted or unsubstituted C2-C25alkenyl, substituted or unsubstituted C3-C25cycloalkyl, substituted or unsubstituted C3-C25silyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C6-C30aromatic ring fused with C3-C30aliphatic ring, substituted or unsubstituted C2-C30heteroaryl; said R4 are the same or different from each other, selected from hydrogen, deuterium, cyano, trifluoromethyl, nitro, halogen or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, adamantyl, norbornanyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, trimethylsilyl, triphenylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, benzocyclopropanoyl, benzocyclobutanoyl, benzocyclopentanoyl, benzocyclohexanoyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, carbazolyl, benzoxazolyl, benzothiazolyl, benzofuranyl or benzothiophenyl; said el is selected from 0, 1, 2, 3, 4, or 5, said e2 is selected from 0, 1, 2, 3, or 4, said e3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, said e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, said e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, said e6 is selected from 0, 1, 2, or 3, said e7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, said e8 is selected from 0, 1, 2, 3, 4, 5, or 6, said e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, said e 10 is selected from 0, 1, or 2, said e 11 is selected from 0 or 1.

7. The nitrogen-containing heterocyclic compound according to claim 1, wherein said nitrogen-containing heterocyclic compound is selected from any one of the following structures:

8. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being located between the anode and the cathode or outside of either of the anode and the cathode, characterized in that, said organic layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1-7.

9. An organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, and comprises a hole transport region, a light emitting layer, and an electron transport region located between the light emitting layer and the cathode, characterized in that said electron transport region comprises any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1-7.

10. An organic electroluminescent device according to claim 9, wherein the electron transport region comprises at least one of an electron injection layer, an electron transport layer and a hole blocking layer, characterized in that at least one of said electron injection layer, electron transport layer and hole blocking layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1-7.

Images