Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof. The nitrogen-containing heterocyclic compound provided by the invention has very good electron migration ability and proper HOMO energy level and LUMO energy level, can improve the electron transmission efficiency when being applied to an electron transmission region, can also be well matched with an adjacent organic functional layer on the energy level, is beneficial to the generation of excitons in a light-emitting layer, and can improve the light-emitting efficiency of the light-emitting layer. The luminous efficiency, the service life and the driving voltage of the device are improved; the nitrogen-containing heterocyclic compound has good thermal stability and chemical stability, is not easy to decompose and age in a high-temperature and corrosive gas working environment, has good film-forming property, and can further improve the service life and the stability of a device.

Description

Technical Field

[0001] This invention belongs to the field of organic optoelectronic materials technology, specifically relating to a nitrogen-containing heterocyclic compound and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting devices (OLEDs) have advantages such as self-illumination, thin and light shape, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, high color purity, high definition, and flexible display. They are considered by the industry to be one of the most promising display and lighting technologies.

[0003] OLEDs employ a multilayer thin-film structure, including an anode, a cathode, and an emissive layer. The emissive layer is located between the anode and the cathode. It also includes various organic functional layers in the hole transport region between the anode and the emissive layer, and various organic functional layers in the electron transport region between the cathode and the emissive layer. When a voltage is applied, holes injected from the anode and electrons injected from the cathode pass through the various organic functional layers to reach the emissive layer, where they recombine to form excitons. These excitons then release energy as photons through radiative transitions, thus generating visible light. Therefore, OLED devices achieve efficient electroluminescence through the synergistic effect of the various organic functional layers. The organic functional layers in the electron transport region, including the electron injection layer, electron transport layer, and hole blocking layer, play a role in injecting and transporting electrons, and also promote the generation of excitons in the emissive layer. This requires them to have good electron transport capabilities and appropriate HOMO and LUMO energy levels.

[0004] To further improve the performance of OLED devices, such as driving voltage, luminous efficiency, and lifespan, it is still necessary to develop electron transport materials with even better performance. Summary of the Invention

[0005] To solve the above-mentioned technical problems, the present invention provides a nitrogen-containing heterocyclic compound having the structure shown in formula (I):

[0006] Wherein, each time X and Y appear, they are selected from CR or N in the same or different manner, and at least one X is selected from N and at least one Y is selected from N. Each time R appears, it is selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1~C12 alkyl group, substituted or unsubstituted C3~C12 cycloalkyl group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C3~C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3~C12 aliphatic ring and a C6~C30 aromatic ring. R2 and R3 are independently selected from one of the following groups, and R1 and R4 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R2 and R4 are independently selected from one of the following groups, and R1 and R3 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R3 and R4 are independently selected from one of the following groups, and R1 and R2 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group:

[0007] The a mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the k mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, either the same or different. The R mentioned 11 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. 11 They can be connected to form a ring; The R mentioned 12 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group; X1 is selected from O, S or CR 13 R 14 The X2 is selected from O, S or NR. 15 ; The R mentioned 13 R 14 R 15 R 16 It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C3-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; each time the substituent appears, it is selected from one of the following: deuterium atom, tritium atom, halogen atom, substituted or unsubstituted alkyl groups of C1-C30, substituted or unsubstituted cycloalkyl groups of C3-C30, substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; The L1, L2, L3, L4, L 11The substituent is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; each time the substituent appears, it is selected from one of the following, either the same or different: a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroarylene, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0008] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains the nitrogen-containing heterocyclic compound described in the present invention.

[0009] Beneficial effects: The nitrogen-containing heterocyclic compounds provided by this invention have excellent electron mobility and appropriate HOMO and LUMO energy levels. When applied to the electron transport region, they can improve electron transport efficiency and achieve good energy level matching with adjacent organic functional layers, which is beneficial for exciton generation in the light-emitting layer, thereby improving the luminous efficiency, lifespan, and driving voltage of the device. The nitrogen-containing heterocyclic compounds also have good thermal and chemical stability, and are not prone to decomposition and aging in high-temperature and corrosive gas environments. They also have good film-forming properties, which can further improve the lifespan and stability of the device. Detailed Implementation

[0010] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0011] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and comprises atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0012] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0013] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0014] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0015] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0016] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The cycloalkenyl groups described above are preferably cyclopentenyl or cyclohexenyl.

[0017] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0018] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0019] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, imidazole, pyridinyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthiophene, etc., but are not limited thereto; the fused-ring heteroaryl groups include benzothiophene, benzofuranyl, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, etc., but are not limited thereto. The aforementioned heteroaryl groups are preferably benzothiophene, benzofuran, indolyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuran, dibenzothiophene, carbazole, or pyridyl.

[0020] The monovalent group formed by the fusion of an aromatic ring and an aliphatic ring in this invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from an aliphatic ring (cycloalkane, cycloene, cycloyne) fused with an aromatic ring. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. It may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto. The aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms. It may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of monovalent groups formed by the fusion of aliphatic and aromatic rings may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, and naphthocyclohexyl.

[0021] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0022] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0023] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0024] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0025] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, or a monovalent group formed by the fusion of an aromatic ring and an aliphatic ring, preferably deuterium, halogen, amino, cyano, nitro, C1 ~C12 alkyl, C3~C12 cycloalkyl, C3~C12 cycloalkenyl, C3~C12 heterocycloalkyl, C6~C30 aryl, C2~C30 heteroaryl, when substituted by multiple substituents, the multiple substituents may be the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane Cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene The following groups are used: phenanthrene, deuterated phenanthrene, triphenylene, deuterated triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, benzofuranyl, benzothiophene, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzoxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl. When substituted with multiple substituents, the substituents may be the same or different from each other, and two adjacent substituents may be linked together to form a ring.

[0026] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any optional position on the ring.

[0027] Any one of the points. For example, Can represent , , . Can represent , , ; Can represent , , , , , , , , , And so on.

[0028] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , , . Can represent or And so on.

[0029] The linked ring structures described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic rings) refer to groups connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0030] .

[0031] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0032] In this specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0033] The statement that a certain layer is located "above" another layer or electrode in this invention can be interpreted as being directly above another layer or electrode, or it can be that other layer structures exist in between.

[0034] The term "a certain layer" in this invention refers to a layer "between" two layers, two electrodes, or one layer and an electrode. It can be interpreted as the only layer structure between the two, or as one or more layer structures existing between the two.

[0035] This invention provides a nitrogen-containing heterocyclic compound having the structure shown in formula (IA) or (IB):

[0036] Wherein, each time X and Y appear, they are selected from CR or N in the same or different manner, and at least one X is selected from N and at least one Y is selected from N. Each time R appears, it is selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1~C12 alkyl group, substituted or unsubstituted C3~C12 cycloalkyl group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C3~C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3~C12 aliphatic ring and a C6~C30 aromatic ring. R2 and R3 are independently selected from one of the following groups, and R1 and R4 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R2 and R4 are independently selected from one of the following groups, and R1 and R3 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R3 and R4 are independently selected from one of the following groups, and R1 and R2 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group:

[0037] The a mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the k mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, either the same or different. The R mentioned 11 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. 11 They can be connected to form a ring; The R mentioned 12Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group; X1 is selected from O, S or CR 13 R 14 The X2 is selected from O, S or NR. 15 ; The R mentioned 13 R 14 R 15 R 16 It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C3-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; each time the substituent appears, it is selected from one of the following: deuterium atom, tritium atom, halogen atom, substituted or unsubstituted alkyl groups of C1-C30, substituted or unsubstituted cycloalkyl groups of C3-C30, substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; The L1, L2, L3, L4, L 11 The substituent is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; each time the substituent appears, it is selected from one of the following, either the same or different: a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroarylene, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

[0038] Preferably, the substituents in "substituted or unsubstituted" are independently selected from deuterium atoms; fluorine atoms; cyano groups; methyl groups substituted or unsubstituted by one or more of deuterium and fluorine atoms; ethyl groups; n-propyl groups; isopropyl groups substituted or unsubstituted by one or more of deuterium and fluorine atoms; n-butyl groups; sec-butyl groups; isobutyl groups; tert-butyl groups substituted or unsubstituted by one or more of deuterium and fluorine atoms; and groups substituted or unsubstituted by one or more of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, and tert-butyl groups as follows: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl; and groups substituted or unsubstituted by one or more of deuterium, fluorine, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, or isopropyl. The following groups are substituted or unsubstituted from one or more of the following: phenyl, naphthyl, anthracene, phenanthryl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, benzoxazolyl, benzothiazolyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, and benzocycloheptane. When there are multiple substituents, the multiple substituents may be the same or different.

[0039] Preferably, at least one X is selected from N; or at least two X are selected from N; or three X are selected from N.

[0040] Preferably, at least one Y is selected from N; or at least two Y are selected from N; or three Y are selected from N.

[0041] Preferably, the nitrogen-containing heterocyclic compound has a structure shown in one of formulas (II-A) to (II-E):

[0042] Preferably, Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following groups:

[0043] The a mentioned 21Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the k mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, either the same or different. The R mentioned 21 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. 21 They can be connected to form a ring; The R mentioned 22 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group; The X3 is selected from O, S, and CR. 23 R 24 or NR 25 The X4 is selected from O, S or NR. 25 ; The R mentioned 23 R 24 R 25 R 26Independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or the R group described above. 23 With R 24 Connected to form a ring.

[0044] Preferably, one, two, three, or four of the Ar1, Ar2, Ar3, and Ar4 groups can be independently selected from each of the above groups.

[0045] Preferably, 0, 1, 2, 3, or 4 of Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following groups: .

[0046] Preferably, L1, L2, L3, L4, L 11 Independently selected from one of the single-bonded groups, as shown below:

[0047] Wherein, X5 is selected from O or S; The a mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group.

[0048] Preferably, the R, R 21 R 101 Each time it appears, the same or different selections are made from hydrogen atom; deuterium atom; tritium atom; fluorine atom; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterium atom, fluorine atom, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidine The following groups, substituted or unsubstituted, are found in the following groups: phenyl, biphenyl, naphthyl, anthracene, and phenanthryl. One of the following: triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0049] Preferably, the R 11Each time it appears, the same or different selections are made from: hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene; deuterium atom; fluorine atom; cyano; methyl; deuterated methyl The following groups are substituted or unsubstituted: phenyl, biphenyl, naphthyl, anthracene, methyl-substituted phenyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornene, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophene, indolyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzofuranyl, dibenzothiophene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane. One of the following: yl, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0050] Preferably, the R 12 Each time it appears, it is selected from the same or different groups of hydrogen atom; deuterium atom; tritium atom; fluorine atom; cyano; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornenealkyl.

[0051] Preferably, the R 22 R 102 Each time it appears, it is selected from the following, either identically or differently: hydrogen atom; deuterium atom; tritium atom; fluorine atom; methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornene alkyl.

[0052] Preferably, the R 13 R 14 R 15 R16 Independently selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantane; norbornyl; deuterated atom, fluorine atom, cyano, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, iso The following groups, substituted or unsubstituted, are selected from quinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane: phenyl, biphenyl, naphthyl, anthraceneyl, phenanthrene, and triphenylene. One of the following: phenyl, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane.

[0053] Preferably, the R 23 R 24 R 25 R 26Independently selected from methyl; deuterated methyl; trifluoromethyl; ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; isobutyl; sec-butyl; tert-butyl; deuterated tert-butyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; adamantyl; norbornyl; deuterated, fluorine, methyl, deuterated methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, naphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalyl One or more of the following groups, substituted or unsubstituted, are quinazolinyl, benzofuranyl, benzothiopheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane: phenyl, biphenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, fluorenyl, spirodifluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, benzofuranyl, benzothiapheneyl, indolyl, benzoxazolyl, benzothiazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiapheneyl, carbazoleyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, and benzocycloheptane, or the aforementioned R. 23 With R 24 Connected to form a ring.

[0054] Preferably, the nitrogen-containing heterocyclic compound is selected from one of the following compounds: .

[0055] The nitrogen-containing heterocyclic compound represented by formula (I) of this invention can be prepared by the following synthetic route:

[0056] Wherein, X, Y, R1, R2, R3, R4, Ar1, Ar2, Ar3, Ar4, L1, L2, L3, and L4 are all as described in this invention; each time P1 and P2 appear, they are selected from fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms, either the same or different. Each time Q1 and Q2 appear, they are selected from B(OH)2 or different. .

[0057] In the above synthetic route, compound (Y1) reacts with compounds (Y2) and (Y3) via a C-C coupling reaction to obtain the target compound (I). There are no specific restrictions on the reaction order of compounds (Y1) with compounds (Y2) and (Y3); they can react with compound (Y2) first, then with compound (Y3), or with compound (Y3) first, then with compound (Y2), or even react with compounds (Y2) and (Y3) simultaneously.

[0058] The above synthetic route employs reaction types commonly used in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation method utilizes readily available raw materials, has a simple process, and yields excellent results. This invention can also employ other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0059] The present invention also provides an organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains the nitrogen-containing heterocyclic compound described in the present invention.

[0060] Preferably, the electron transport region contains the nitrogen-containing heterocyclic compound described in this invention.

[0061] Preferably, the electron transport region includes an electron transport layer, and the electron transport layer contains the nitrogen-containing heterocyclic compound described in this invention.

[0062] Preferably, the electron transport region includes a hole blocking layer, which contains the nitrogen-containing heterocyclic compound described in this invention.

[0063] Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron transport layer contains the nitrogen-containing heterocyclic compound described in this invention.

[0064] Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron transport layer contains the nitrogen-containing heterocyclic compound described in this invention.

[0065] Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the hole blocking layer contains the nitrogen-containing heterocyclic compound described in this invention.

[0066] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. Preferably, the hole transport region includes a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. Alternatively, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein the hole injection layer is located between the anode and the light-emitting layer, the hole transport layer is located between the hole injection layer and the light-emitting layer, and the light-emitting auxiliary layer is located between the hole transport layer and the light-emitting layer.

[0067] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4''-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1~HT-18, compounds p-1~p-5, but not limited to these.

[0068] .

[0069] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a value of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0070] The light-emitting auxiliary layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1 [-Biphenyl]-4-amine, compounds HT-1 to HT-18 as shown above, but not limited thereto.

[0071] The luminescent layer of this invention comprises a guest material and a host material, and a dual-host material formed from two host materials can be used. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, aromatic amine compounds, etc. Specific examples may include 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 9,10-bis(2-naphthyl)anthracene (ADN), etc., but is not limited to these. The guest material includes, but is not limited to, aromatic amine derivatives, boron compounds, metal complexes, etc. Specific examples may include, but are not limited to, tri(2-phenylpyridine)iridium (Ir(ppy)3), di(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tri(1-phenyl-isoquinoline)iridium (Ir(piq)3), and 2,5,8,11-tetratert-butylperylene (TBPe).

[0072] The light-emitting layer described in this invention may also include a sensitizer.

[0073] The sensitizer described in this invention refers to a material that enables the luminescent material in the light-emitting layer to fully utilize electroexcitons, thereby improving the performance of OLED devices. In organic electroluminescent devices, the sensitizer may perform functions such as exciton trapping, exciton conversion, and exciton transfer. The sensitizers are mainly classified into phosphorescent sensitizers, TADF sensitizers, and excitocomplex sensitizers. Examples of phosphorescent sensitizers include iridium complexes and platinum complexes. TADF sensitizers primarily utilize TADF materials, and excitocomplex sensitizers consist of donor and acceptor materials.

[0074] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. Preferably, the electron transport region includes an electron injection layer and an electron transport layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, and the electron transport layer is located between the electron injection layer and the light-emitting layer. Preferably, the electron transport region includes an electron injection layer, an electron transport layer, and a hole blocking layer, wherein the electron injection layer is located between the cathode and the light-emitting layer, the electron transport layer is located between the electron injection layer and the light-emitting layer, and the hole blocking layer is located between the electron transport layer and the light-emitting layer.

[0075] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0076] The electron transport layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can utilize high electron transport properties such as aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, and polymeric compounds. Examples of electron transport materials for the electron transport layer include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), and the nitrogen-containing heterocyclic compounds described in this invention, but are not limited thereto. Preferably, the electron transport material is selected from the nitrogen-containing heterocyclic compounds described in this invention.

[0077] The hole blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The hole blocking material used in the hole blocking layer requires a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the hole blocking material must be lower than that of the host material of the emissive layer to effectively block holes. Further, the electron mobility of the hole blocking layer material used is 10... -6 cm 2A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, and polymeric compounds. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI), BAlq, and the nitrogen-containing heterocyclic compounds described in this invention, but are not limited thereto. Preferably, the hole-blocking layer material is selected from the nitrogen-containing heterocyclic compounds described in this invention.

[0078] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0079] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0080] The organic electroluminescent device of the present invention may further include a capping layer, wherein the capping layer is located on the side of the cathode opposite to the anode.

[0081] The capping layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, and compounds CP-1 to CP-5, but are not limited thereto.

[0082]

[0083] The aforementioned organic layers, cathode, and anode can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0084] The thickness of each of the aforementioned organic layers is typically between 1 nanometer and 100 micrometers, preferably between 5 nanometers and 1000 nanometers, and more preferably between 5 nanometers and 200 nanometers. The thickness of the anode and cathode is adjusted according to the required transparency.

[0085] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0086] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0087] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent. Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0088] Synthesis Example 1: Synthesis of Intermediate HH

[0089] Synthesis of intermediate HH-326:

[0090] Under nitrogen protection, add AA-326 (29.39 g, 70 mmol) and THF (160 ml), cool to -78°C, add 54 ml (1.57 mol / L) of n-butyllithium / hexane solution, stir for 1 h, then add triisopropyl borate (20.12 g, 107 mmol), stir for 1 h. Return to room temperature, add 75 ml of saturated ammonium chloride aqueous solution and 160 ml of toluene. Rinse the organic layer with distilled water (3... Wash with 150 ml of water, dry with anhydrous magnesium sulfate, filter, and remove the solvent by vacuum distillation to obtain intermediate HH-326 (22.84 g, yield 76%). The purity of the solid was ≥99.77% as determined by HPLC. Mass spectrometry m / z: 429.1638 (theoretical value: 429.1649).

[0091] Following the synthesis steps of intermediate HH-326, by substituting the raw materials accordingly, the intermediates shown in Table 1a can be obtained: Table 1a

[0092] Synthesis Example 2: Synthesis of Compound 6

[0093] Under nitrogen protection, AA-6 (30.48 g, 100 mmol), BB-6 (25.39 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and palladium acetate (0.90 g, 4 mmol) were added to a reaction flask, followed by 1500 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization from toluene / methanol (9:1 v / v) yielded intermediate EE-6 (22.58 g, 73% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 308.0954 (theoretical value: 308.0944).

[0094] Under nitrogen protection, EE-6 (15.46 g, 50 mmol), DD-6 (27.71 g, 100 mmol), potassium carbonate (20.73 g, 150 mmol), and Pd2(dba)3 (0.92 g, 1.00 mmol) were added to a reaction flask, followed by 1000 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 6 (24.95 g, yield 71%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 702.3328 (theoretical value: 702.3316). Theoretical elemental content (%) C 48 H 22 D 10 N6: C, 82.02; H, 6.02; N, 11.96. Measured elemental content (%): C, 82.05; H, 6.01; N, 11.97.

[0095] Synthesis Example 3: Synthesis of Compound 12

[0096] Replacing BB-6 with BB-12, and following the same steps as in Synthesis Example 2, yielded compound 12 (26.01 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 844.3324 (theoretical value: 844.3314). Theoretical elemental content (%) C 60 H 40 N6: C, 85.28; H, 4.77; N, 9.95. Measured elemental content (%): C, 85.26; H, 4.78; N, 9.92.

[0097] Synthesis Example 4: Synthesis of Compound 37

[0098] Under nitrogen protection, AA-37 (35.18 g, 100 mmol), BB-37 (12.19 g, 100 mmol), potassium carbonate (20.73 g, 150 mmol), and palladium acetate (0.45 g, 2 mmol) were added to a reaction flask, followed by 1000 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization from toluene / methanol (9:1 v / v) yielded intermediate CC-37 (23.56 g, 78% yield). HPLC analysis showed a solid purity ≥99.82%. Mass spectrometry m / z: 299.9120 (theoretical value: 299.9108).

[0099] Under nitrogen protection, CC-37 (18.12 g, 60 mmol), DD-37 (9.72 g, 60 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and potassium carbonate (12.44 g, 90 mmol) were added to the reaction flask, followed by 600 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain EE-37 (15.47 g, 76%); HPLC purity ≥99.84%. Mass spectrometry m / z: 338.0616 (theoretical value: 338.0629).

[0100] Under nitrogen protection, EE-37 (13.57 g, 40 mmol), DD-6 (22.17 g, 80 mmol), potassium carbonate (16.59 g, 120 mmol), and Pd2(dba)3 (0.73 g, 0.8 mmol) were added to a reaction flask, followed by 800 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, and extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 37 (21.11 g, 72% yield). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 732.3017 (theoretical value: 732.3001). Theoretical elemental content (%) C 51 H 36 N6: C, 83.58; H, 4.95; N, 11.47. Measured elemental content (%): C, 83.59; H, 4.93; N, 11.46.

[0101] Synthesis Example 5: Synthesis of Compound 69

[0102] Replacing DD-37 with DD-69, and following the same steps as in Synthesis Example 4, yielded compound 69 (22.86 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 782.2783 (theoretical value: 782.2794). Theoretical elemental content (%) C 54 H 34 N6O: C, 82.84; H, 4.38; N, 10.73. Measured elemental content (%): C, 82.83; H, 4.35; N, 10.74.

[0103] Synthesis Example 6: Synthesis of Compound 77

[0104] Replacing DD-37 with DD-77, and following the same steps as in Synthesis Example 4, yielded compound 77 (27.99 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 932.3613 (theoretical value: 932.3627). Theoretical elemental content (%) C 67 H 44 N6: C, 86.24; H, 4.75; N, 9.01. Measured element content (%): C, 86.25; H, 4.73; N, 9.02.

[0105] Synthesis Example 7: Synthesis of Compound 97

[0106] By replacing AA-6 with AA-97 and BB-6 with BB-37, and following the same steps as in Synthesis Example 2, compound 97 (26.67 g) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 692.2671 (theoretical value: 692.2688). Theoretical elemental content (%) C 48 H 32 N6: C, 83.21; H, 4.66; N, 12.13. Measured element content (%): C, 83.22; H, 4.64; N, 12.16.

[0107] Synthesis Example 8: Synthesis of Compound 101

[0108] By replacing AA-6 with AA-97 and BB-6 with BB-101, and following the same steps as in Synthesis Example 2, compound 101 (30.59 g) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 804.3924 (theoretical value: 804.3940). Theoretical elemental content (%) C 56 H 48 N6: C, 83.55; H, 6.01; N, 10.44. Measured elemental content (%): C, 83.53; H, 6.02; N, 10.45.

[0109] Synthesis Example 9: Synthesis of Compound 102

[0110] By replacing AA-37 with AA-102 and DD-37 with BB-12, and following the same steps as in Synthesis Example 4, compound 102 (23.07 g) was obtained. HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 768.3021 (theoretical value: 768.3001). Theoretical elemental content (%) C 54 H 36 N6: C, 84.35; H, 4.72; N, 10.93. Measured element content (%): C, 84.37; H, 4.73; N, 10.94.

[0111] Synthesis Example 10: Synthesis of Compound 126

[0112] By replacing AA-6 with AA-97 and BB-6 with BB-126, and following the same steps as in Synthesis Example 2, compound 126 (33.37 g) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 926.3132 (theoretical value: 926.3118). Theoretical elemental content (%) C 62 H 38 N8O2: C, 80.33; H, 4.13; N, 12.09. Measured elemental content (%): C, 80.34; H, 4.12; N, 12.06.

[0113] Synthesis Example 11: Synthesis of Compound 137

[0114] By replacing AA-37 with AA-102 and DD-37 with DD-137, and following the same steps as in Synthesis Example 4, compound 137 (28.03 g) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 946.3408 (theoretical value: 946.3420). Theoretical elemental content (%) C 67 H 42 N6O: C, 84.97; H, 4.47; N, 8.87. Measured elemental content (%): C, 84.96; H, 4.49; N, 8.86.

[0115] Synthesis Example 12: Synthesis of Compound 150

[0116] By replacing AA-37 with AA-102 and DD-37 with DD-150, and following the same steps as in Synthesis Example 4, compound 150 (22.32 g) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 743.2776 (theoretical value: 743.2797). Theoretical elemental content (%) C 51 H 33 N7: C, 82.35; H, 4.47; N, 13.18. Measured elemental content (%): C, 82.34; H, 4.49; N, 13.16.

[0117] Synthesis Example 13: Synthesis of Compound 156

[0118] Under nitrogen protection, AA-156 (44.32 g, 100 mmol), BB-37 (24.39 g, 200 mmol), potassium carbonate (41.46 g, 300 mmol), and palladium acetate (0.90 g, 4 mmol) were added to a reaction flask, followed by 2000 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization from toluene / methanol (9:1 v / v) yielded intermediate EE-156 (26.12 g, 76% yield). HPLC analysis showed a solid purity ≥99.87%. Mass spectrometry m / z: 341.9819 (theoretical value: 341.9811).

[0119] Under nitrogen protection, EE-156 (20.62 g, 60 mmol), FF-156 (21.19 g, 60 mmol), Pd(PPh3)4 (0.28 g, 0.24 mmol), and potassium carbonate (12.44 g, 90 mmol) were added to the reaction flask, followed by 600 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was refluxed for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, extracted with dichloromethane, and the organic phases were combined. The organic phases were dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to obtain GG-156 (25.74 g, 75%); HPLC purity ≥99.84%. Mass spectrometry m / z: 571.1802 (theoretical value: 571.1815).

[0120] Under nitrogen protection, GG-156 (22.88 g, 40 mmol), DD-6 (11.08 g, 40 mmol), potassium carbonate (8.29 g, 60 mmol), and Pd2(dba)3 (0.37 g, 0.4 mmol) were added to a reaction flask, followed by 400 mL of a toluene / ethanol / water (2:1:1) mixture. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, quenched with water, and extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and recrystallized from toluene to give compound 156 (22.45 g, 73% yield). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 768.3015 (theoretical value: 768.3001). Theoretical elemental content (%) C 54 H 36 N6: C, 84.35; H, 4.72; N, 10.93. Measured elemental content (%): C, 84.32; H, 4.73; N, 10.92.

[0121] Synthesis Example 14: Synthesis of Compound 170

[0122] By replacing BB-6 with BB-37 and DD-6 with FF-170, and following the same steps as in Synthesis Example 2, compound 170 (33.94 g) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 892.3332 (theoretical value: 892.3314). Theoretical elemental content (%) C 64 H 40 N6: C, 86.07; H, 4.51; N, 9.41. Measured elemental content (%): C, 86.06; H, 4.53; N, 9.40.

[0123] Synthesis Example 15: Synthesis of Compound 174

[0124] Replacing DD-37 with DD-174 and DD-6 with FF-174, while following the same steps as in Synthesis Example 4, yielded compound 174 (29.79 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 966.5341 (theoretical value: 966.5349). Theoretical elemental content (%) C 68 H 66 N6: C, 84.43; H, 6.88; N, 8.69. Measured elemental content (%): C, 84.45; H, 6.87; N, 8.66.

[0125] Synthesis Example 16: Synthesis of Compound 188

[0126] Replacing FF-156 with DD-6 and DD-6 with HH-12, while following the same steps as in Synthesis Example 13, yielded compound 188 (24.59 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 808.2962 (theoretical value: 808.2951). Theoretical elemental content (%) C 56 H 36 N6O: C, 83.15; H, 4.49; N, 10.39. Measured elemental content (%): C, 83.16; H, 4.47; N, 10.38.

[0127] Synthesis Example 17: Synthesis of Compound 198

[0128] Replacing FF-156 with DD-6 and DD-6 with HH-198, all other steps were the same as in Synthesis Example 13, yielding compound 198 (23.49 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 782.2781 (theoretical value: 782.2794). Theoretical elemental content (%) C 54 H 34 N6O: C, 82.84; H, 4.38; N, 10.73. Measured elemental content (%): C, 82.85; H, 4.36; N, 10.75.

[0129] Synthesis Example 18: Synthesis of Compound 272

[0130] By replacing AA-6 with AA-97, BB-6 with BB-37, and DD-6 with FF-272, and following the same steps as in Synthesis Example 2, compound 272 (31.27 g) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 844.3332 (theoretical value: 844.3314). Theoretical elemental content (%) C 60 H 40 N6: C, 85.28; H, 4.77; N, 9.95. Measured elemental content (%): C, 85.27; H, 4.76; N, 9.97.

[0131] Synthesis Example 19: Synthesis of Compound 287

[0132] By replacing AA-6 with AA-97, BB-6 with BB-287, and DD-6 with FF-287, and following the same steps as in Synthesis Example 2, compound 287 (29.27 g) was obtained. HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 812.4242 (theoretical value: 812.4257). Theoretical elemental content (%) C 56 H 16 D 20 N6: C, 82.73; H, 6.94; N, 10.34. Measured elemental content (%): C, 82.72; H, 6.96; N, 10.33.

[0133] Synthesis Example 20: Synthesis of Compound 292

[0134] By replacing AA-6 with AA-97, BB-6 with BB-12, and DD-6 with FF-292, and following the same steps as in Synthesis Example 2, compound 292 (28.73 g) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 944.3641 (theoretical value: 944.3627). Theoretical elemental content (%) C 68 H 44 N6: C, 86.42; H, 4.69; N, 8.89. Measured elemental content (%): C, 86.43; H, 4.67; N, 8.88.

[0135] Synthesis Example 21: Synthesis of Compound 318

[0136] By replacing AA-156 with AA-318, FF-156 with DD-6, and DD-6 with HH-318, and following the same steps as in Synthesis Example 13, compound 318 (27.99 g) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 932.3609 (theoretical value: 932.3627). Theoretical elemental content (%) C 67 H 44 N6: C, 86.24; H, 4.75; N, 9.01. Measured element content (%): C, 86.25; H, 4.73; N, 9.00.

[0137] Synthesis Example 22: Synthesis of Compound 326

[0138] By replacing AA-156 with AA-318, BB-37 with BB-326, FF-156 with DD-6, and DD-6 with HH-326, and following the same steps as in Synthesis Example 13, compound 326 (26.09 g) was obtained. HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 846.3237 (theoretical value: 846.3219). Theoretical elemental content (%) C 58 H 38 N8: C, 82.25; H, 4.52; N, 13.23. Measured elemental content (%): C, 82.24; H, 4.53; N, 13.26.

[0139] Synthesis Example 23: Synthesis of Compound 373

[0140] Replacing FF-156 with FF-373 and DD-6 with HH-373, and following the same steps as in Synthesis Example 13, yielded compound 373 (26.33 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 843.3372 (theoretical value: 843.3362). Theoretical elemental content (%) C 61 H 41 N5: C, 86.81; H, 4.90; N, 8.30. Measured elemental content (%): C, 86.83; H, 4.91; N, 8.32.

[0141] Synthesis Example 24: Synthesis of Compound 405

[0142] By replacing AA-156 with AA-318, FF-156 with HH-373, and DD-6 with HH-405, and following the same steps as in Synthesis Example 13, compound 405 (24.32 g) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 799.3660 (theoretical value: 799.3675). Theoretical elemental content (%) C 57 H 45 N5: C, 85.58; H, 5.67; N, 8.75. Measured elemental content (%): C, 85.56; H, 5.66; N, 8.73.

[0143] Synthesis Example 25: Synthesis of Compound 421

[0144] By replacing AA-156 with AA-318, BB-37 with DD-69, FF-156 with DD-6, and DD-6 with HH-373, and following the same steps as in Synthesis Example 13, compound 421 (32.26 g) was obtained. HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 871.2928 (theoretical value: 871.2947). Theoretical elemental content (%) C 61 H 37 N5O2: C, 84.02; H, 4.28; N, 8.03. Measured elemental content (%): C, 84.03; H, 4.27; N, 8.02.

[0145] Synthesis Example 26: Synthesis of Compound 487

[0146] By replacing BB-37 with BB-12, DD-37 with BB-37, and DD-6 with FF-487, and following the same steps as in Synthesis Example 4, compound 487 (24.24 g) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 766.3080 (theoretical value: 766.3096). Theoretical elemental content (%) C 56 H 38 N4: C, 87.70; H, 4.99; N, 7.31. Measured elemental content (%): C, 87.72; H, 4.98; N, 7.32.

[0147] Synthesis Example 27: Synthesis of Compound 489

[0148] By replacing BB-37 with BB-287, DD-37 with BB-37, and DD-6 with HH-373, and following the same steps as in Synthesis Example 4, compound 489 (22.23 g) was obtained. HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 740.2954 (theoretical value: 740.2940). Theoretical elemental content (%) C 54 H 36 N4: C, 87.54; H, 4.90; N, 7.56. Measured elemental content (%): C, 87.55; H, 4.92; N, 7.55.

[0149] Synthesis Example 28: Synthesis of Compound 501

[0150] By replacing AA-156 with AA-318, FF-156 with FF-501, and DD-6 with HH-373, and following the same steps as in Synthesis Example 13, compound 501 (24.95 g) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 842.3421 (theoretical value: 842.3409). Theoretical elemental content (%) C 62 H 42 N4: C, 88.33; H, 5.02; N, 6.65. Measured elemental content (%): C, 88.34; H, 5.04; N, 6.62.

[0151] Synthesis Example 29: Synthesis of Compound 518

[0152] Replacing FF-156 with DD-6 and DD-6 with HH-518, all other steps were the same as in Synthesis Example 13, yielding compound 518 (21.28 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 690.2795 (theoretical value: 690.2783). Theoretical elemental content (%) C 50 H 34 N4: C, 86.93; H, 4.96; N, 8.11. Measured elemental content (%): C, 86.96; H, 4.95; N, 8.12.

[0153] Synthesis Example 30: Synthesis of Compound 570

[0154] By replacing AA-6 with AA-97, BB-6 with BB-37, and DD-6 with FF-570, and following the same steps as in Synthesis Example 2, compound 570 (26.33 g) was obtained. HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 692.2669 (theoretical value: 692.2688). Theoretical elemental content (%) C 48 H 32 N6: C, 83.21; H, 4.66; N, 12.13. Measured element content (%): C, 83.22; H, 4.64; N, 12.16.

[0155] Synthesis Example 31: Synthesis of Compound 585

[0156] By replacing AA-156 with AA-37, FF-156 with DD-585, and DD-6 with HH-585, and following the same steps as in Synthesis Example 4, compound 585 (23.67 g) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 788.3198 (theoretical value: 788.3191). Theoretical elemental content (%) C 60 H 40 N2: C, 91.34; H, 5.11; N, 3.55. Measured elemental content (%): C, 91.32; H, 5.14; N, 3.53.

[0157] Synthesis Example 32: Synthesis of Compound 596

[0158] By replacing AA-156 with AA-318, BB-37 with BB-596, FF-156 with HH-518, and DD-6 with HH-373, and following the same steps as in Synthesis Example 13, compound 596 (25.99 g) was obtained. HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 889.3438 (theoretical value: 889.3457). Theoretical elemental content (%) C 67 H 43 N3: C, 90.41; H, 4.87; N, 4.72. Measured elemental content (%): C, 90.42; H, 4.84; N, 4.73.

[0159] The following are other compounds besides the nitrogen-containing heterocyclic compounds described in this invention used in the device fabrication examples:

[0160] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. The emission spectrum of the device prepared according to this invention was tested at atmospheric pressure and room temperature, as well as at a current density of 10 mA / cm². 2 The luminous efficiency was measured. The lifetime (brightness decay to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Tables 1 and 2.

[0161] Comparative device fabrication example 1: Comparative device 1

[0162] First, the ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0163] The following layers were deposited layer by layer on the ITO glass substrate: a) HT-14 and p-1 (mass ratio 100:1) as hole injection layer with a thickness of 10 nm; b) HT-4 as hole transport layer with a thickness of 40 nm; c) HT-5 as light-emitting auxiliary layer with a thickness of 20 nm; d) HOST-1, HOST-3 and Ir(ppy)2(m-bppy) (mass ratio 48:48:4) as light-emitting layer with a thickness of 30 nm; e) TPBi as hole blocking layer with a thickness of 20 nm; f) ref-1 and Liq (mass ratio 1:1) as electron transport layer with a thickness of 20 nm; g) LiF as electron injection layer with a thickness of 1 nm; h) Al as cathode with a thickness of 150 nm.

[0164] Comparative device fabrication examples 2-4: Comparative devices 2-4

[0165] By sequentially replacing ref-1 in the electron transport layer with ref-2, ref-3, ref-4, and ref-5, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 4 can be obtained.

[0166] Device fabrication examples 1-31: Light-emitting devices 1-31

[0167] By sequentially replacing ref-1 in the electron transport layer with compounds 6, 12, 37, 69, 77, 97, 101, 102, 126, 137, 150, 156, 170, 174, 188, 198, 272, 287, 292, 318, 326, 373, 405, 421, 487, 489, 501, 518, 570, 585, and 596, and following the same steps as in Comparative Device Preparation Example 1, light-emitting devices 1 to 31 can be obtained.

[0168] Table 1

[0169] Comparative device fabrication example 5: Comparative device 5

[0170] First, the ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0171] The following layers were deposited layer by layer on the ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 20 nm; b) HT-8 as a hole transport layer with a thickness of 40 nm; c) HT-13 as a light-emitting auxiliary layer with a thickness of 20 nm; d) HOST-2, HOST-3 and Ir(dpm)(piq)2 (mass ratio 47:47:6) as a light-emitting layer with a thickness of 30 nm; e) ref-1 as a hole blocking layer with a thickness of 10 nm; f) TMPyPB and Liq (mass ratio 1:1) as an electron transport layer with a thickness of 30 nm; g) LiF as an electron injection layer with a thickness of 1 nm; h) Al as a cathode with a thickness of 150 nm.

[0172] Comparative device fabrication examples 6-8: Comparative devices 6-8

[0173] By sequentially replacing ref-1 in the hole blocking layer with ref-2, ref-3, ref-4, and ref-5, and following the same steps as in Comparative Device Preparation Example 6, Comparative Devices 6-8 can be obtained.

[0174] Device fabrication examples 32-62: Light-emitting devices 32-62

[0175] By sequentially replacing ref-1 in the hole blocking layer with compounds 6, 12, 37, 69, 77, 97, 101, 102, 126, 137, 150, 156, 170, 174, 188, 198, 272, 287, 292, 318, 326, 373, 405, 421, 487, 489, 501, 518, 570, 585, and 596, and following the same steps as in Comparative Device Preparation Example 6, light-emitting devices 32-62 can be obtained.

[0176] Table 2

[0177] The device data in Tables 1 and 2 show that the nitrogen-containing heterocyclic compounds provided by this invention, as electron transport layer materials or hole blocking layer materials, can effectively improve the driving voltage, luminous efficiency and lifespan of OLED devices.

[0178] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A nitrogen-containing heterocyclic compound, characterized in that, The nitrogen-containing heterocyclic compound has the structure shown in formula (I): Wherein, each time X and Y appear, they are selected from CR or N in the same or different manner, and at least one X is selected from N and at least one Y is selected from N. Each time R appears, it is selected from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1~C12 alkyl group, substituted or unsubstituted C3~C12 cycloalkyl group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C3~C30 heteroaryl group, or a monovalent group formed by fusion of a substituted or unsubstituted C3~C12 aliphatic ring and a C6~C30 aromatic ring. R2 and R3 are independently selected from one of the following groups, and R1 and R4 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R2 and R4 are independently selected from one of the following groups, and R1 and R3 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group; or, R3 and R4 are independently selected from one of the following groups, and R1 and R2 are independently selected from one of hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, and substituted or unsubstituted C3-C12 cycloalkyl group: The a mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the k mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, either the same or different. The R mentioned 11 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. 11 They can be connected to form a ring; The R mentioned 12 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group; X1 is selected from O, S or CR 13 R 14 The X2 is selected from O, S or NR. 15 ; The R mentioned 13 R 14 R 15 R 16 It is independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; Ar1, Ar2, Ar3, and Ar4 are independently selected from one of the following: substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C3-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; each time the substituent appears, it is selected from one of the following: deuterium atom, tritium atom, halogen atom, substituted or unsubstituted alkyl groups of C1-C30, substituted or unsubstituted cycloalkyl groups of C3-C30, substituted or unsubstituted aryl groups of C6-C30, substituted or unsubstituted heteroaryl groups of C2-C30, and monovalent groups formed by fusion of substituted or unsubstituted aliphatic rings of C3-C12 and aromatic rings of C6-C30; The L1, L2, L3, L4, L 11 The substituent is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a divalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; each time the substituent appears, it is selected from one of the following, either the same or different: a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroarylene, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, At least one X is selected from N; or at least two X are selected from N; or three X are selected from N. At least one Y is selected from N; or at least two Y are selected from N; or three Y are selected from N.

3. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The nitrogen-containing heterocyclic compound has a structure shown in one of formulas (II-A) to (II-E): 。 4. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The Ar1, Ar2, Ar3, and Ar4 groups are independently selected from one of the following groups: The a mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, or 7, either identically or differently; c 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the g mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the h mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the i 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the j mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the k mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13, either the same or different. The R mentioned 21 Each time it appears, it is selected, either identically or differently, from one of the following: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or two adjacent R groups. 21 They can be connected to form a ring; The R mentioned 22 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group; The X3 is selected from O, S, and CR. 23 R 24 or NR 25 The X4 is selected from O, S or NR. 25 ; The R mentioned 23 R 24 R 25 R 26 Independently selected from one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, or a monovalent group formed by fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring, or the R group described above. 23 With R 24 Connected to form a ring.

5. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The L1, L2, L3, L4, L 11 Independently selected from one of the single-bonded groups, as shown below: Wherein, X5 is selected from O or S; The a mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the c mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the d mentioned 101 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 101 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either identically or differently; the f mentioned 101 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the g mentioned 101 Each time it appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different. The R mentioned 101 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a monovalent group formed by the fusion of a substituted or unsubstituted C3-C12 aliphatic ring and a C6-C30 aromatic ring; The R mentioned 102 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C12 alkyl group, or substituted or unsubstituted C3-C12 cycloalkyl group.

6. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that, The nitrogen-containing heterocyclic compound is selected from one of the following compounds: 。 7. An organic electroluminescent device, comprising a cathode, an anode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The organic layer contains a nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The electron transport region contains the nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 8, wherein the electron transport region comprises an electron transport layer, characterized in that, The electron transport layer contains a nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6.

10. The organic electroluminescent device according to claim 8, wherein the electron transport region includes a hole blocking layer, characterized in that, The hole-blocking layer contains the nitrogen-containing heterocyclic compound as described in any one of claims 1 to 6.

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