Nitrogen-containing heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. The compound provided by the invention has relatively high electron mobility, and the combination efficiency of holes and electrons can be improved; when the material is used as a host material, the triplet state energy level of the material is well matched with that of a guest material, and the luminous efficiency of an organic electroluminescent device can be improved; when the material is used as a hole blocking layer material, holes can be effectively prevented from migrating to one side of an electron transmission layer, electron injection transmission barriers are reduced, driving voltage is reduced, local voltage is prevented from being too high, and the service life of a device is prolonged.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to a nitrogen-containing heterocyclic compound and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED), also known as organic light-emitting diode, has many advantages such as high luminous efficiency, high color contrast, fast response speed, light texture, low power consumption, etc., making it the most promising new display technology.

[0003] The structure of traditional organic electroluminescent devices is mostly sandwich-shaped, mainly including anode, cathode, hole injection layer, hole transport layer, hole blocking layer, light-emitting layer, electron blocking layer, electron transport layer, electron injection layer and cover layer. Under the action of an external electric field, electrons enter the electron transport layer from the cathode and holes enter the hole transport layer from the anode. The two recombine in the light-emitting layer to generate excitons, which radiatively transition back to the ground state and emit light.

[0004] In order to make organic electroluminescent devices have high luminous efficiency and long service life, the key lies in the good performance and mutually matching energy levels of the organic functional layer materials of the device. For example, the triplet energy level of the host material needs to be higher than the triplet energy level of the guest material to prevent the energy backflow from the guest material to the host material and confine the triplet excitons to the guest molecules. However, organic electroluminescent materials are still facing many problems, such as the mismatch of triplet energy levels of host and guest materials. Therefore, in order to break through the bottlenecks of OLED in driving voltage, luminous efficiency, service life, etc., it is urgent to develop more efficient host materials. Summary of the invention

[0005] In order to solve the problems of high driving voltage, low luminous efficiency and short service life of organic electroluminescent devices, the present invention provides a nitrogen-containing heterocyclic compound and an organic electroluminescent device comprising the heterocyclic compound, which can significantly improve the above problems, so that the organic electroluminescent device has a low driving voltage, high luminous efficiency and a long service life.

[0006] Specifically, the present invention provides a nitrogen-containing heterocyclic compound having a structure represented by Formula I:

[0007]

[0008] Said Y is selected from O or S;

[0009] The z is independently selected from CH or N;

[0010] The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0011] The q is selected from 0, 1, 2, 3, 4 or 5;

[0012] The ring A is selected from any one of the following groups:

[0013]

[0014] The T is independently selected from CH or N;

[0015] The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0016] The t1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2 or 3; the t4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t5 is selected from 0, 1, 2, 3 or 4; the t6 is selected from 0, 1, 2, 3, 4 or 5;

[0017] The x is independently selected from C(R3) or N, and at least one x is a N atom;

[0018] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0019] The Ar1 is selected from any one of the following groups:

[0020]

[0021] The G is independently selected from CH or N;

[0022] The s0 is selected from 1, 2 or 3;

[0023] The ring W is selected from a substituted or unsubstituted C3-C30 alicyclic ring;

[0024] The G1 is selected from O, S or N (Rk);

[0025] The M is selected from O or S;

[0026] The Rd is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C12 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring;

[0027] The Rk and Rg are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0028] The m0 is selected from 0, 1, 2, 3, 4 or 5; the m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m3 is selected from 0, 1, 2, 3 or 4; the m4 is selected from 0, 1, 2 or 3.

[0029] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0030] The condition is that when ring A is When , L1 is not a single bond;

[0031] The L2 and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0032] The present invention provides an organic electroluminescent device, comprising an anode, a cathode and an organic functional layer located between the anode and the cathode or located outside at least one of the electrodes, wherein the organic functional layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0033] The present invention also provides a stacked organic electroluminescent device, comprising an anode, a cathode, a first light-emitting unit, a second light-emitting unit and a charge generating layer, wherein the first light-emitting unit, the second light-emitting unit and the charge generating layer are located between the anode and the cathode, the charge generating layer is located between the first light-emitting unit and the second light-emitting unit, and the charge generating layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0034] Beneficial effects:

[0035] The nitrogen-containing heterocyclic compound provided by the present invention has a high electron mobility and can effectively improve the combination efficiency of holes and electrons; when used as a host material, it has a good match with the triplet energy level of the guest material and can improve the luminous efficiency of the organic electroluminescent device; when used as a hole blocking layer material, it can effectively block the migration of holes to the electron transport layer side, reduce the electron injection and transport barrier, reduce the driving voltage, avoid excessive local voltage, and extend the service life of the device.

[0036] In summary, the nitrogen-containing heterocyclic compounds provided by the present invention are a class of OLED materials with excellent performance. DETAILED DESCRIPTION

[0037] The following will be clearly and completely described in conjunction with the technical solutions of the specific embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0038] In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes the atom in both its natural isotopic abundance and unnatural abundance.

[0039] The halogen mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0040] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing a hydrogen atom in an alkane molecule, which 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 not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0041] The silyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from a silane molecule, and can be represented by the group described by -Si(Ry)(Ry)(Ry), wherein Ry is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, alkenyl, alkoxy, and cycloalkyl groups described above, preferably having 1 to 30 carbon atoms, preferably 1 to 25 carbon atoms, more preferably 1 to 22 carbon atoms, and most preferably 1 to 18 carbon atoms. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethyl-tert-butylsilyl, diethylmethylsilyl, tricyclopropylsilyl, tricyclobutylsilyl, triphenylsilyl, etc., but are not limited thereto.

[0042] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a 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 above-mentioned cycloalkyl group is preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane.

[0043] The aryl group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group, or a condensed aryl group, preferably having 6 to 30 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 having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited thereto; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, such as naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluoranthenyl, fluorenyl, benzofluorenyl, spirofluorenyl, spirobifluorenyl, etc., but not limited thereto.

[0044] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, preferably having 2 to 30 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 attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrrolyl, furanyl, thienyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the condensed-ring heteroaryl group may include spirofluorene oxanthracene, spirofluorene thioxanthracene, acridinyl, 9,10-dihydroacridinyl, naphthyridinyl, indolyl, phenoxazinyl , phenothiazinyl, phenoxathiyl, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazoline, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, o-phenanthroline, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, benzothiazolyl, dibenzothienyl, benzodibenzothienyl, benzoxazolyl, dibenzoxazolyl, benzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl and the like, but are not limited thereto.

[0045] The fused cyclic group of an alicyclic ring and an aromatic ring of the present invention refers to a monovalent group formed by removing a hydrogen atom from an alicyclic ring and an aromatic ring after the alicyclic ring and the aromatic ring are fused together. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, such as benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but is not limited thereto.

[0046] The fused ring group of an alicyclic ring and a heteroaromatic ring described in the present invention refers to a monovalent group formed by condensing an alicyclic ring and a heteroaromatic ring together and removing a hydrogen atom. It preferably has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, such as pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, carbazocyclopropyl, carbazocyclobutyl, carbazocyclopentyl, carbazocyclohexyl, carbazocycloheptyl, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, and the like, but is not limited thereto.

[0047] The arylene group of the present invention refers to an aryl group having two binding positions, i.e., a divalent group. The above description of the aryl group can be applied to it, except that the arylene group is a divalent group.

[0048] The heteroarylene group in the present invention means a heteroaryl group having two binding positions, i.e., a divalent group. The above description of the heteroaryl group can be applied to it, except that the heteroarylene group is a divalent group.

[0049] The "substitution" described in the present 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 the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0050] The term "substituted or unsubstituted" as used herein means not substituted or substituted by one or more substituents selected from the group consisting of a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkylboryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylamine group, a substituted or unsubstituted C6-C60 The arylboryl or silyl group is preferably a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C6-C30 aryl group, a C2-C30 heteroaryl group, or a silyl group. When substituted by multiple substituents, the multiple substituents are 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: a deuterium atom, a tritium atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, a trifluoromethyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a deuterated tert-butyl group, a cycloalkyl ... Propanyl, methyl substituted cyclopropanyl, ethyl substituted cyclopropanyl, deuterated cyclopropanyl, cyclobutanyl, methyl substituted cyclobutanyl, ethyl substituted cyclobutanyl, deuterated cyclobutanyl, cyclopentanyl, methyl substituted cyclopentanyl, ethyl substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl substituted cyclohexanyl, ethyl substituted cyclohexanyl, n-propyl substituted cyclohexanyl, n-butyl substituted cyclohexanyl, cyclohexane substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptyl, adamantyl, methyl substituted adamantyl, ethyl substituted adamantyl, deuterated adamantyl, norbornanyl, methyl substituted norbornanyl, ethyl Substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl, when substituted with multiple substituents, the multiple substituents are the same or different.

[0051] In the present invention, when the position of a substituent on an aromatic ring is not fixed, it means that it can be connected to any of the corresponding optional positions of the aromatic ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0052] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.

[0053] In the present invention, "adjacent groups are connected to form a substituted or unsubstituted ring" means that adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring or aliphatic heterocyclic ring. The "adjacent groups" refer to two substituents on two directly connected atoms, a substituent arranged to be closest to the corresponding substituent in space, and another substituent on the atom with the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered to be "adjacent" to each other. The aliphatic ring and the aliphatic heterocycle may be saturated rings or unsaturated rings, and the specific rings formed by connection may be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, spiro rings or condensed rings; the number of carbon atoms in the ring of the aromatic ring formed is preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms; the number of carbon atoms in the ring of the heteroaromatic ring formed is preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms; the number of carbon atoms in the ring of the aliphatic ring formed is preferably 3 to 30 carbon atoms, particularly preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms; the number of carbon atoms in the ring of the aliphatic heterocycle formed is preferably 3 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, more preferably 2 to 12 carbon atoms, and most preferably 2 to 7 carbon atoms. Furthermore, the ring formed by the connection may be the following: for example, benzene, naphthalene, indene, cyclopentane, cyclopentaneacene, cyclohexane, cyclohexaneacene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but it is not limited thereto.

[0054]

[0055] The present invention provides a nitrogen-containing heterocyclic compound having a structure represented by Formula I:

[0056]

[0057] Said Y is selected from O or S;

[0058] The z is independently selected from CH or N;

[0059] The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0060] The q is selected from 0, 1, 2, 3, 4 or 5;

[0061] The ring A is selected from any one of the following groups:

[0062]

[0063] The T is independently selected from CH or N;

[0064] The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0065] The t1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2 or 3; the t4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t5 is selected from 0, 1, 2, 3 or 4; the t6 is selected from 0, 1, 2, 3, 4 or 5;

[0066] The x is independently selected from C(R3) or N, and at least one x is a N atom;

[0067] The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0068] The Ar1 is selected from any one of the following groups:

[0069]

[0070] The G is independently selected from CH or N;

[0071] The s0 is selected from 1, 2 or 3;

[0072] The ring W is selected from a substituted or unsubstituted C3-C30 alicyclic ring;

[0073] The G1 is selected from O, S or N (Rk);

[0074] The M is selected from O or S;

[0075] The Rd is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C12 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring;

[0076] The Rk and Rg are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring;

[0077] The m0 is selected from 0, 1, 2, 3, 4 or 5; the m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m3 is selected from 0, 1, 2, 3 or 4; the m4 is selected from 0, 1, 2 or 3.

[0078] The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group;

[0079] The condition is that when ring A is When , L1 is not a single bond;

[0080] The L2 and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0081] Preferably, the nitrogen-containing heterocyclic compound has any one of the structures represented by Formula II-1 to Formula II-7:

[0082]

[0083] The definitions of Ar1, ring A, L1, L2, L3, R1, R3, Y, z, and q are the same as those in Formula I;

[0084] The h1 is selected from 0, 1 or 2.

[0085] Preferably, the nitrogen-containing heterocyclic compound has any one of the structures represented by Formula III-1 to Formula III-7:

[0086]

[0087] Preferably, the Any one selected from the following groups:

[0088]

[0089] The R1 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl;

[0090] The q0 is selected from 0, 1, 2, 3, 4 or 5; the q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2 or 3; and the q3 is selected from 0, 1 or 2.

[0091] Preferably, the ring A is selected from any one of the following groups:

[0092]

[0093]

[0094] The R2 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, dibenzofuranyl, dibenzothienyl, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring;

[0095] In the “substituted or unsubstituted”, the substituent is selected from deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, deuterated phenyl, methylphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0096] The t1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2 or 3; the t4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t5 is selected from 0, 1, 2, 3 or 4; the t6 is selected from 0, 1, 2, 3, 4 or 5; the t7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t8 is selected from 0, 1 or 2.

[0097] Preferably, Ar1 is selected from any one of the following groups:

[0098]

[0099]

[0100]

[0101] The Rd is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring;

[0102] The Rg is selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl;

[0103] In the “substituted or unsubstituted”, the substituent is selected from deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, deuterated phenyl, methylphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0104] wherein a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a7 is selected from 0, 1, 2, 3, 4, 5 or 6; and a8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0105] Preferably, L1 is selected from a single bond or any one of the following groups:

[0106]

[0107] The R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent R4 are connected to each other to form a substituted or unsubstituted ring;

[0108] The Rp and Rq are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or adjacent Rp and Rq are connected to form a substituted or unsubstituted spiro ring;

[0109] The r1 is selected from 0, 1, 2, 3 or 4, the r2 is selected from 0, 1, 2 or 3, and the r3 is selected from 0, 1 or 2.

[0110] More preferably, L1 is selected from a single bond or any one of the following groups:

[0111]

[0112] Preferably, L2 and L3 are independently selected from a single bond or any one of the following groups:

[0113]

[0114]

[0115] The Rn is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent Rn are connected to each other to form a substituted or unsubstituted ring;

[0116] The Rw and Rz are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or adjacent Rw and Rz are connected to form a substituted or unsubstituted spiro ring;

[0117] The b1 is selected from 0, 1, 2, 3 or 4, the b2 is selected from 0, 1, 2 or 3, and the b3 is selected from 0, 1 or 2.

[0118] More preferably, L2 and L3 are independently selected from a single bond or any one of the following groups:

[0119]

[0120] Most preferably, the nitrogen-containing heterocyclic compound is selected from one of the following compounds:

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] The above lists only some specific structural forms of the nitrogen-containing heterocyclic compounds represented by Formula I, but the present invention is not limited to these chemical structures listed, and all those based on Formula I and with substituents as defined in the present invention should be included.

[0142] The nitrogen-containing heterocyclic compound represented by formula I of the present invention can be prepared by one of the following synthetic routes:

[0143]

[0144] The main reaction type involved in the present invention is Suzuki coupling reaction. The raw materials in the synthesis route provided by the present invention can be commercially available products, and can also be prepared by preparation methods known in the art.

[0145] The Xe is selected from I, Br or Cl; the Xf is selected from I, Br or Cl; the Xg is selected from I, Br or Cl; and the Xh is selected from I, Br or Cl.

[0146] Alternatively, the order of the above reactions may be changed to obtain the nitrogen-containing heterocyclic compound represented by formula I of the present invention.

[0147] The above reaction routes all adopt the reaction types commonly used in organic synthesis, and the reaction conditions (for example, the selection of types such as reaction solvent, catalyst, ligand, base, dosage, and the order and method of addition) are not particularly limited. The above preparation method raw materials are easy to obtain, the preparation process is simple, and the yield is excellent. The compound shown in the formula I provided by the present invention can also be synthesized using the conventional reaction types in other organic syntheses, without particular restrictions, and the above is only an example of a synthetic route.

[0148] The present invention provides an organic electroluminescent device, comprising an anode, a cathode and an organic functional layer, wherein the organic functional layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0149] Preferably, the organic functional layer may be one or more, and the organic functional layer is located between the anode and the cathode or outside at least one of the anode and the cathode. As the organic functional layer comprising the aforementioned compound, an anode-side organic functional layer (hole transport layer, hole injection layer, luminescence auxiliary layer, etc.) disposed between the anode and the light-emitting layer, a light-emitting layer, a cathode-side organic functional layer (electron transport layer, hole blocking layer, electron injection layer, etc.) disposed between the cathode and the light-emitting layer, and an organic functional layer (light extraction layer, light efficiency improvement layer, sealing layer, etc.) disposed outside the cathode can be cited, but it is not limited thereto.

[0150] Preferably, the organic functional layer is located between the anode and the cathode, and the organic functional layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0151] Preferably, the organic functional layer is located between the anode and the cathode, the organic functional layer includes a hole transport region, a light-emitting layer and an electron transport region, the light-emitting layer is located between the hole transport region and the electron transport region, and the electron transport region or the light-emitting layer contains any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0152] More preferably, the electron transport region comprises an electron injection layer, an electron transport layer, and a hole blocking layer, and at least one of the electron transport layer and the hole blocking layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0153] Preferably, the organic functional layer comprises an electron transport layer, and the electron transport layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0154] Preferably, the organic functional layer comprises a hole blocking layer, and the hole blocking layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0155] Preferably, the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0156] More preferably, the light-emitting layer comprises a guest material and a host material, and the host material is selected from any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0157] The present invention also provides a stacked organic electroluminescent device, comprising an anode, a cathode, a first light-emitting unit, a second light-emitting unit and a charge generating layer, wherein the first light-emitting unit, the second light-emitting unit and the charge generating layer are located between the anode and the cathode, the charge generating layer is located between the first light-emitting unit and the second light-emitting unit, and the charge generating layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0158] Preferably, the charge generation layer comprises a P-type charge generation layer and an N-type charge generation layer, and the N-type charge generation layer comprises any one or more of the nitrogen-containing heterocyclic compounds described in the present invention.

[0159] The present invention has no particular limitation on the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The organic functional layers of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are introduced below:

[0160] The anode of the present invention needs to have a higher work function in order to improve the hole injection efficiency. The anode material can be selected from the following materials, metal oxides, combinations of metals and oxides, metals or their alloys, etc. Specific examples may include indium tin oxide (ITO), indium zinc oxide (IZO), aluminum (Al), titanium (Ti), gold (Au), platinum (Pt), copper (Cu), silver (Ag), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but are not limited thereto.

[0161] The cathode of the present invention needs to have a lower work function in order to improve the electron injection efficiency. The cathode material can be selected from the following materials, metals or their alloys, etc. Specific examples may include aluminum (Al), silver (Ag), calcium (Ca), indium (In), magnesium: silver (Mg: Ag), etc., but are not limited thereto.

[0162] The hole injection layer material of the present invention needs to have good hole injection ability and have a more suitable HOMO energy level, which can effectively reduce the interface barrier between the anode and the hole transport layer and improve the hole injection ability. The hole injection layer material can be selected from the following materials, aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organics, polymers, etc. Specific examples may include copper phthalocyanine (CuPC), 4,4',4"-tri(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(4-vinyltriphenylamine) (PVTPA), etc., but are not limited thereto.

[0163] The hole transport layer material of the present invention needs to have a high hole mobility to facilitate hole injection. The hole transport layer material can be selected from the following materials: aromatic amine derivatives, carbazole derivatives, fluorene derivatives, polymers, and the like. Specific examples may include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), etc., but are not limited thereto.

[0164] The electron blocking layer material of the present invention needs to have good hole transport ability and electron blocking ability, and can effectively transport holes and limit the escape of electrons to the interface of the light-emitting layer. The electron blocking layer material can be selected from the following materials, aromatic amine derivatives, carbazole derivatives, etc., preferably at least one of the nitrogen-containing heterocyclic compounds described in the present invention. Specific examples may include N, N-di([1, 1'-biphenyl]-4-yl)-(9H-carbazole-9-yl)-[1, 1'-biphenyl]-4-amine, N-(4'-(9H-carbazole-9-yl)-[1, 1'-biphenyl]-4-N-([1, 1'-biphenyl]-4-yl)-9, 9-dimethyl-9H-fluorene-2-amine, etc., but are not limited thereto.

[0165] The light-emitting layer material of the present invention generally contains a guest (doping) material and a host material. The guest material can be a simple fluorescent material, a phosphorescent material or a TADF material, or a combination of fluorescent and phosphorescent materials. The host material of the light-emitting layer not only needs to have bipolar charge transfer properties, but also needs to have an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. This type of material can include carbazole derivatives, distyryl aryl derivatives, isopropylbenzene derivatives, triarylamine derivatives, anthracene derivatives and pyrene derivatives, preferably at least one of the nitrogen-containing heterocyclic compounds of the present invention. Specific examples may include 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), 9-(5-(3-(9H-carbazol-9-yl)phenyl)pyridine-3- The invention also includes the following: 1,3-bis(N-carbazolyl)benzene (MCP), tris(6-fluoro-8-hydroxyquinoline)aluminum (6FAlq3), tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), bis(8-hydroxyquinoline)zinc (Znq2), but are not limited thereto. The nitrogen-containing heterocyclic compound of the present invention is preferred.

[0166] The guest material may be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but not limited thereto. Specific examples may include bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium (Ir(npy)2acac), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetonate)iridium (Ir(bzq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 9-(9-phenylcarbazole-3-yl)-10-(naphthalene-1-yl) (PCAN), 1,4-bis(4-(9H-carbazole-9-yl)phenylvinyl)benzene (BCzSB), but not limited thereto.

[0167] The hole blocking layer of the present invention needs to have good electron transport ability and hole blocking ability, which can effectively transport electrons and limit the escape of holes to the interface of the light-emitting layer. The hole blocking layer material can be selected from the following materials, metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azabenzene derivatives, etc., preferably at least one of the nitrogen-containing heterocyclic compounds described in the present invention. Specific examples may include 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]bipyridine (TmPyPB), etc., but are not limited thereto. The nitrogen-containing heterocyclic compound described in the present invention is preferred.

[0168] The electron transport material of the present invention needs to have a high electron mobility for electron injection. The electron transport layer material can be selected from the following materials: quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azabenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, etc., preferably at least one of the nitrogen-containing heterocyclic compounds described in the present invention. Specific examples may include 8-hydroxyquinoline aluminum (Alq3), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 1,3,5-tri(4-pyridin-3-ylphenyl)benzene (TpPyPB), 1,3,5-tri(4-pyridinylquinoline-2-yl)benzene (TPyQB), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), etc., but are not limited thereto. The nitrogen-containing heterocyclic compound of the present invention is preferred.

[0169] The electron injection material of the present invention needs to have good electron injection ability and have a more suitable LUMO energy level, so as to reduce the interface barrier between the cathode and the electron transport layer and improve the electron injection ability. The electron injection layer material includes but is not limited to the following materials, metals, alkali metals, alkaline earth metals, metal compounds, metal oxides, metal halides, alkaline earth metal compounds, alkaline earth metal oxides, alkaline earth metal halides, alkali metal compounds, alkali metal oxides, alkali metal halides, etc. Specific examples may include lithium (Li), strontium (Sr), ytterbium (Yb), lithium fluoride (LiF), sodium fluoride (NaF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline lithium (Liq), tris (8-hydroxyquinoline) aluminum (Alq3), cesium carbonate (Cs2CO3), rubidium acetate (CH3COORb), lithium oxide (Li2O), barium oxide (BaO), etc., but are not limited thereto.

[0170] The charge generation layer (CGL layer) of the present invention needs to have good electron-withdrawing ability, film stability and electron tolerance, which is conducive to improving the charge generation efficiency and the stability of the device. The CGL layer material includes but is not limited to the following materials, alkali metals, alkaline earth metals, lanthanide metals, nitrogen-containing benzene derivatives, silicon-containing heterocyclic compounds, etc. Specific examples may include alkali metals such as Li, Na, K, Rb, Cs, Fr, etc.; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, Ra, etc.; Group 15 metals such as Bi (bismuth), Sb (antimony), etc.; lanthanide metals such as lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), 2,9-di(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF), tetrathiafulvalene (TTF), etc., but are not limited thereto. The nitrogen-containing heterocyclic compound described in the present invention is preferred.

[0171] There is no particular limitation on the method for preparing the thin films in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, etc. may be used, but are not limited thereto.

[0172] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, VR, and car taillights.

[0173] The technical scheme and technical effects of the present invention are further illustrated below with reference to embodiments and comparative examples.

[0174] The mass spectra of the compounds of the present invention were determined using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, with chloroform as the solvent;

[0175] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar of Germany, with a sample mass of 5 to 10 mg.

[0176] Synthesis Example 1: Preparation of Compound 6

[0177]

[0178] Synthesis of intermediate B-6

[0179] Under nitrogen protection, A-6 (29.29 g, 120.00 mmol), a-6 (22.13 g, 120.00 mmol), potassium acetate (23.55 g, 240.00 mmol), tetrakis(triphenylphosphine)palladium (2.77 g, 2.4 mmol), 800 mL toluene, 200 mL ethanol, and 200 mL water were added to the reaction bottle, and the mixture was stirred under reflux for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol (5:1) to obtain intermediate B-6 (23.95 g, yield 75%); HPLC detected the solid purity ≧99.87%. Mass spectrum m / z: 264.9821 (theoretical value: 264.9810).

[0180] Synthesis of intermediate C-6

[0181] Under nitrogen protection, add B-6 (21.29 g, 80.00 mmol), b-6 (22.41 g, 80.00 mmol), potassium carbonate (22.11 g, 160.00 mmol), tetrakis(triphenylphosphine)palladium (1.85 g, 1.60 mmol), 500 mL toluene, 150 mL ethanol, 150 mL water into the reaction bottle, stir under reflux for 4.5 hours, after the reaction, cool the reaction mixture to room temperature, filter, wash with distilled water, and then recrystallize the obtained solid with toluene to obtain intermediate C-6 (22.42 g, yield 73%); HPLC detected the solid purity ≧99.87%. Mass spectrum m / z: 383.0841 (theoretical value: 383.0825).

[0182] Synthesis of intermediate D-6

[0183] Under nitrogen protection, C-6 (19.19 g, 50 mmol), diboronic acid pinacol ester (12.70 g, 50 mmol), potassium phosphate (26.53 g, 125 mmol) and 400 mL of N,N-dimethylformamide solution were added to the reaction bottle. After nitrogen replaced the air 3 times, DPPF palladium dichloride (0.73 g, 1 mmol) was added, and the reaction was stirred for 4.5 hours under heating. After the reaction, the reactant was cooled to room temperature, distilled water was added, and it was extracted with dichloromethane (180 mL×3 times). The organic phase was separated, and the organic phase was dried over anhydrous magnesium sulfate, the solvent was concentrated by rotary evaporation, the temperature was reduced and crystallization was carried out, and the solid was recrystallized from toluene / ethanol (10:1) to obtain D-6 (19.01 g, yield 80%), HPLC purity ≧99.82%, mass spectrum m / z: (measured value: 475.2080; theoretical value: 475.2067).

[0184] Synthesis of compound 6

[0185] Under nitrogen protection, D-6 (16.64 g, 35 mmol), c-6 (10.18 g, 35 mmol), potassium carbonate (9.67 g, 70 mmol), 200 mL toluene, 100 mL ethanol, and 100 mL water were added to the reaction bottle. After nitrogen replaced the air three times, tetrakis(triphenylphosphine)palladium (0.40 g, 0.35 mmol) was added, and the mixture was stirred and refluxed for 5 hours. After the reaction was completed, the reactants were cooled to room temperature, filtered, and the filter cake was rinsed with ethanol. The filter cake was recrystallized from toluene to obtain compound 6 (14.16 g, yield 67%), HPLC purity ≧99.96%, mass spectrum m / z: (measured value: 603.2079; theoretical value: 603.2059). Theoretical element content (%) C 41 H 25 N5O: C, 81.57; H, 4.17; N, 11.60. Measured element content (%): C, 81.59; H, 4.15; N, 11.64.

[0186] Synthesis Example 2: Preparation of Compound 7

[0187]

[0188] According to the same preparation method as compound 6 in Synthesis Example 1, c-6 was replaced by an equal molar amount of c-7, and the other steps were the same to obtain compound 7 (14.95 g,). The solid purity was ≥99.93% by HPLC. Mass spectrum m / z: (measured value: 601.2170; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.88; H, 4.54; N, 6.95.

[0189] Synthesis Example 3: Preparation of Compound 21

[0190]

[0191] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-21 and c-21, respectively, and the other steps were the same to obtain compound 21 (14.32 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 601.2140; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.80; H, 4.55; N, 6.95.

[0192] Synthesis Example 4: Preparation of Compound 23

[0193]

[0194] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-23 and c-23, and the other steps were the same to obtain compound 23 (14.53 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 601.2170; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.87; H, 4.56; N, 6.95.

[0195] Synthesis Example 5: Preparation of Compound 25

[0196]

[0197] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were equimolar to A-25 and c-7 respectively, and the other steps were the same to obtain compound 25 (16.13 g). The solid purity was ≥99.98% by HPLC. Mass spectrum m / z: (measured value: 677.2450; theoretical value: 677.2467). Theoretical element content (%) C 49 H 31 N3O: C, 86.83; H, 4.61; N, 6.20. Measured element content (%): C, 86.88; H, 4.65; N, 6.23.

[0198] Synthesis Example 6: Preparation of Compound 47

[0199]

[0200] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-47 and c-47, respectively, and the other steps were the same to obtain compound 47 (13.64 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 581.2450; theoretical value: 581.2467). Theoretical element content (%) C 41 H 31 N3O: C, 84.65; H, 5.37; N, 7.22. Measured element content (%): C, 84.60; H, 5.32; N, 7.20.

[0201] Synthesis Example 7: Preparation of Compound 49

[0202]

[0203] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, b-6, c-6 were replaced by equimolar A-49, b-46, c-49, respectively, and the other steps were the same to obtain compound 49 (14.95 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 601.2172; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.80; H, 4.56; N, 6.94.

[0204] Synthesis Example 8: Preparation of Compound 50

[0205]

[0206] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-46 and c-50, respectively, and the other steps were the same to obtain compound 50 (12.51 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 525.1830; theoretical value: 525.1841). Theoretical element content (%) C 37 H 23 N3O: C, 84.55; H, 4.41; N, 7.99. Measured element content (%): C, 84.50; H, 4.44; N, 7.95.

[0207] Synthesis Example 9: Preparation of Compound 64

[0208]

[0209] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-64 and c-64, respectively, and the other steps were the same to obtain compound 64 (12.65 g). The solid purity was ≥99.91% by HPLC. Mass spectrum m / z: (measured value: 539.1618; theoretical value: 539.1634). Theoretical element content (%) C 37 H 21 N3O2: C, 82.36; H, 3.92; N, 7.79. Measured element content (%): C, 82.31; H, 3.90; N, 7.76.

[0210] Synthesis Example 10: Preparation of Compound 68

[0211]

[0212] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-68 and c-68 respectively, and the other steps were the same to obtain compound 68 (14.70 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 617.2200; theoretical value: 617.2216). Theoretical element content (%) C 42 H 27 N5O: C, 81.67; H, 4.41; N, 11.34. Measured element content (%): C, 81.64; H, 4.43; N, 11.30.

[0213] Synthesis Example 11: Preparation of Compound 71

[0214]

[0215] According to the same preparation method as compound 6 in Synthesis Example 1, c-6 was replaced by an equal molar amount of c-71, and the other steps were the same to obtain compound 71 (14.16 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 603.2040; theoretical value: 603.2059). Theoretical element content (%) C 41 H 25 N5O: C, 81.57; H, 4.17; N, 11.60. Measured element content (%): C, 81.52; H, 4.12; N, 11.63.

[0216] Synthesis Example 12: Preparation of Compound 95

[0217]

[0218] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-95 and c-95 respectively, and the other steps were the same to obtain compound 95 (12.40 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 528.1680; theoretical value: 528.1699). Theoretical element content (%) C 34 H 20 N6O: C, 77.26; H, 3.81; N, 15.90. Measured element content (%): C, 77.24; H, 3.85; N, 15.92.

[0219] Synthesis Example 13: Preparation of Compound 107

[0220]

[0221] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-46 and c-107, respectively, and the other steps were the same to obtain compound 107 (13.14 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 577.1920; theoretical value: 577.1903). Theoretical element content (%) C 39 H 23 N5O: C, 81.09; H, 4.01; N, 12.12. Measured element content (%): C, 81.04; H, 4.04; N, 12.16.

[0222] Synthesis Example 14: Preparation of Compound 117

[0223]

[0224] Synthesis of Intermediate C-117

[0225] Under nitrogen protection, A-25 (51.23 g, 160.00 mmol), a-6 (14.75 g, 80.00 mmol), potassium acetate (15.70 g, 160.00 mmol), tetrakis(triphenylphosphine)palladium (0.92 g, 0.8 mmol), 500 mL toluene, 150 mL ethanol, and 150 mL water were added to the reaction bottle, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol (10:1) to obtain intermediate C-117 (27.60 g, yield 69%); HPLC detected the solid purity ≧99.81%. Mass spectrum m / z: 499.1070 (theoretical value: 499.1088).

[0226] Synthesis of intermediate D-117

[0227] Under nitrogen protection, C-117 (24.50 g, 50 mmol), diboronic acid pinacol ester (12.70 g, 50 mmol), potassium phosphate (21.23 g, 100 mmol) and 400 mL of N,N-dimethylformamide solution were added to the reaction bottle. After nitrogen replaced the air 3 times, DPPF palladium dichloride (0.73 g, 1 mmol) was added, and the mixture was heated and stirred for 4 hours. After the reaction, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (150 mL×3 times). The organic phase was separated, and the organic phase was dried over anhydrous magnesium sulfate, the solvent was concentrated by rotary evaporation, the temperature was reduced and crystallization was carried out, and the solid was recrystallized from toluene to obtain D-117 (23.36 g, yield 79%), HPLC purity ≧99.86%, mass spectrum m / z: (measured value: 591.2310; theoretical value: 591.2329).

[0228] Synthesis of compound 117

[0229] Under nitrogen protection, D-117 (20.70 g, 35 mmol), c-117 (7.51 g, 35 mmol), potassium carbonate (9.67 g, 70 mmol), 200 mL toluene, 100 mL ethanol, and 100 mL water were added to the reaction bottle. After nitrogen replaced the air three times, tetrakis(triphenylphosphine)palladium (0.40 g, 0.35 mmol) was added, and the mixture was stirred and refluxed for 4.5 hours. After the reaction was completed, the reactants were cooled to room temperature, filtered, and the filter cake was rinsed with ethanol. The filter cake was recrystallized with toluene / ethanol (5:1) to obtain compound 117 (15.32 g, yield 68%), HPLC purity ≧99.93%, mass spectrum m / z: (measured value: 643.2000; theoretical value: 643.2008). Theoretical element content (%) C 43 H 25 N5O2: C, 80.23; H, 3.91; N, 10.88. Measured element content (%): C, 80.28; H, 3.94; N, 10.84.

[0230] Synthesis Example 15: Preparation of Compound 119

[0231]

[0232] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-119 and c-119, respectively, and the other steps were the same to obtain compound 119 (12.21 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 528.1681; theoretical value: 528.1699). Theoretical element content (%) C 34 H 20N6O: C, 77.26; H, 3.81; N, 15.90. Measured element content (%): C, 77.23; H, 3.86; N, 15.94.

[0233] Synthesis Example 16: Preparation of Compound 126

[0234]

[0235] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-49 and c-126 respectively, and the other steps were the same to obtain compound 126 (14.83 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 651.2300; theoretical value: 651.2311). Theoretical element content (%) C 47 H 29 N3O: C, 86.61; H, 4.49; N, 6.45. Measured element content (%): C, 86.64; H, 4.45; N, 6.40.

[0236] Synthesis Example 17: Preparation of Compound 138

[0237]

[0238] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-138 and c-138 respectively, and the other steps were the same to obtain compound 138 (15.06 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 651.2326; theoretical value: 651.2311). Theoretical element content (%) C 47 H 29 N3O: C, 86.61; H, 4.49; N, 6.45. Measured element content (%): C, 86.64; H, 4.45; N, 6.41.

[0239] Synthesis Example 18: Preparation of Compound 142

[0240]

[0241] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, b-6, c-6 were replaced by equimolar A-142, b-46, c-138 respectively, and the other steps were the same to obtain compound 142 (13.50 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 575.1983; theoretical value: 575.1998). Theoretical element content (%) C 41 H 25N3O: C, 85.54; H, 4.38; N, 7.30. Measured element content (%): C, 85.51; H, 4.34; N, 7.32.

[0242] Synthesis Example 19: Preparation of Compound 161

[0243]

[0244] According to the same preparation method as compound 6 in Synthesis Example 1, c-6 was replaced by an equal molar amount of c-161, and the other steps were the same to obtain compound 161 (14.89 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: (measured value: 625.2170; theoretical value: 625.2154). Theoretical element content (%) C 45 H 27 N3O: C, 86.38; H, 4.35; N, 6.72. Measured element content (%): C, 86.35; H, 4.39; N, 6.77.

[0245] Synthesis Example 20: Preparation of Compound 197

[0246]

[0247] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-197 and c-197, and the other steps were the same to obtain compound 197 (15.28 g). The solid purity was ≥99.94% by HPLC. Mass spectrum m / z: (measured value: 651.2322; theoretical value: 651.2311). Theoretical element content (%) C 47 H 29 N3O: C, 86.61; H, 4.49; N, 6.45. Measured element content (%): C, 86.64; H, 4.46; N, 6.40.

[0248] Synthesis Example 21: Preparation of Compound 208

[0249]

[0250] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-46 and c-197, respectively, and the other steps were the same to obtain compound 208 (13.90 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 601.2172; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.81; H, 4.50; N, 6.94.

[0251] Synthesis Example 22: Preparation of Compound 227

[0252]

[0253] According to the same preparation method as compound 6 in Synthesis Example 1, c-6 was replaced with an equal molar amount of c-227, and the other steps were the same to obtain compound 227 (14.24 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 625.2174; theoretical value: 625.2154). Theoretical element content (%) C 45 H 27 N3O: C, 86.38; H, 4.35; N, 6.72. Measured element content (%): C, 86.34; H, 4.37; N, 6.75.

[0254] Synthesis Example 23: Preparation of Compound 236

[0255]

[0256] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-236 and c-236, and the other steps were the same to obtain compound 236 (13.97 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: (measured value: 595.2091; theoretical value: 595.2080). Theoretical element content (%) C 40 H 29 N3OSi: C, 80.64; H, 4.91; N, 7.05. Measured element content (%): C, 80.69; H, 4.93; N, 7.07.

[0257] Synthesis Example 24: Preparation of Compound 266

[0258]

[0259] According to the same preparation method as compound 6 in Synthesis Example 1, a-6, b-6, c-6 were replaced by equimolar a-266, b-266, c-7, and other steps were the same to obtain compound 266 (13.25 g). The solid purity was ≥99.93% by HPLC. Mass spectrum m / z: (measured value: 573.2080; theoretical value: 573.2093). Theoretical element content (%) C 43 H 27NO: C, 90.03; H, 4.74; N, 2.44. Measured element content (%): C, 90.00; H, 4.70; N, 2.40.

[0260] Synthesis Example 25: Preparation of Compound 275

[0261]

[0262] According to the same preparation method as compound 6 in Synthesis Example 1, a-6 and c-6 were replaced by equimolar a-275 and c-275, respectively, and the other steps were the same to obtain compound 275 (15.87 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 676.2532; theoretical value: 676.2515). Theoretical element content (%) C 50 H 32 N2O: C, 88.73; H, 4.77; N, 4.14. Measured element content (%): C, 88.70; H, 4.74; N, 4.10.

[0263] Synthesis Example 26: Preparation of Compound 288

[0264]

[0265] According to the same preparation method as compound 6 in Synthesis Example 1, a-6 and c-6 were replaced by equimolar a-266 and c-288 respectively, and the other steps were the same to obtain compound 288 (14.11 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 601.2136; theoretical value: 601.2154). Theoretical element content (%) C 43 H 27 N3O: C, 85.83; H, 4.52; N, 6.98. Measured element content (%): C, 85.88; H, 4.54; N, 6.96.

[0266] Synthesis Example 27: Preparation of Compound 313

[0267]

[0268] According to the same preparation method as compound 6 in Synthesis Example 1, a-6, b-6, c-6 were replaced by equimolar a-275, b-46, c-71, respectively, and the other steps were the same to obtain compound 313 (12.53 g). The solid purity was ≥99.97% by HPLC. Mass spectrum m / z: (measured value: 526.1780; theoretical value: 526.1794). Theoretical element content (%) C 36 H 22N4O: C, 82.11; H, 4.21; N, 10.64. Measured element content (%): C, 82.09; H, 4.24; N, 10.60.

[0269] Synthesis Example 28: Preparation of Compound 326

[0270]

[0271] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, a-6, c-6 were replaced by equimolar A-326, a-266, c-126, respectively, and the other steps were the same to obtain compound 326 (16.77 g). The solid purity was ≥99.92% by HPLC. Mass spectrum m / z: (measured value: 725.2710; theoretical value: 725.2719). Theoretical element content (%) C 55 H 35 NO: C, 91.01; H, 4.86; N, 1.93. Measured element content (%): C, 91.03; H, 4.88; N, 1.90.

[0272] Synthesis Example 29: Preparation of Compound 380

[0273]

[0274] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, b-6, c-6 were replaced by equimolar A-380, b-380, c-380, respectively, and the other steps were the same to obtain compound 380 (14.63 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 623.2180; theoretical value: 623.2192). Theoretical element content (%) C 42 H 21 D5N4S: C, 80.87; H, 5.01; N, 8.98. Measured element content (%): C, 80.83; H, 5.04; N, 8.93.

[0275] Synthesis Example 30: Preparation of Compound 387

[0276]

[0277] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-380 and c-21 respectively, and the other steps were the same to obtain compound 387 (14.70 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 617.1916; theoretical value 617.1926). Theoretical element content (%) C 43 H27 N3S: C, 83.60; H, 4.41; N, 6.80. Measured element content (%): C, 83.63; H, 4.45; N, 6.84.

[0278] Synthesis Example 31: Preparation of Compound 401

[0279]

[0280] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, b-6, c-6 were replaced by equimolar A-401, b-46, c-47, respectively, and the other steps were the same to obtain compound 401 (12.89 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 541.1623; theoretical value: 541.1613). Theoretical element content (%) C 37 H 23 N3S: C, 82.04; H, 4.28; N, 7.76. Measured element content (%): C, 82.09; H, 4.24; N, 7.73.

[0281] Synthesis Example 32: Preparation of Compound 414

[0282]

[0283] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-414 and c-71 respectively, and the other steps were the same to obtain compound 414 (14.53 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 619.1821; theoretical value: 619.1831). Theoretical element content (%) C 41 H 25 N5S: C, 79.46; H, 4.07; N, 11.30. Measured element content (%): C, 79.49; H, 4.05; N, 11.34.

[0284] Synthesis Example 33: Preparation of Compound 439

[0285]

[0286] According to the same preparation method as compound 117 in Synthesis Example 14, A-25 and c-117 were replaced by equimolar A-380 and c-71 respectively, and the other steps were the same to obtain compound 439 (13.85 g). The solid purity detected by HPLC was ≥99.90%. Mass spectrum m / z: (measured value: 599.1221; theoretical value: 599.1238). Theoretical element content (%) C 37H 21 N5S2: C, 74.10; H, 3.53; N, 11.68. Measured element content (%): C, 74.14; H, 3.56; N, 11.66.

[0287] Synthesis Example 34: Preparation of Compound 455

[0288]

[0289] According to the same preparation method as compound 6 in Synthesis Example 1, A-6, b-6, c-6 were replaced by equimolar A-380, b-46, c-138, respectively, and the other steps were the same to obtain compound 455 (11.91 g). The solid purity was ≥99.90% by HPLC. Mass spectrum m / z: (measured value: 515.1440; theoretical value: 515.1456). Theoretical element content (%) C 35 H 21 N3S: C, 81.53; H, 4.11; N, 8.15. Measured element content (%): C, 81.50; H, 4.15; N, 8.10.

[0290] Synthesis Example 35: Preparation of Compound 489

[0291]

[0292] According to the same preparation method as compound 6 in Synthesis Example 1, A-6 and c-6 were replaced by equimolar A-380 and c-489 respectively, and the other steps were the same to obtain compound 489 (16.27 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 693.2225; theoretical value: 693.2239). Theoretical element content (%) C 49 H 31 N3S: C, 84.82; H, 4.50; N, 6.06. Measured element content (%): C, 84.80; H, 4.54; N, 6.02.

[0293] Synthesis Example 36: Preparation of Compound 579

[0294]

[0295] According to the same preparation method as compound 6 in Synthesis Example 1, a-6, b-6, c-6 were replaced by equimolar a-579, b-266, c-71, respectively, and the other steps were the same to obtain compound 579 (13.50 g). The solid purity was ≥99.97% by HPLC. Mass spectrum m / z: (measured value: 575.1986; theoretical value: 575.1998). Theoretical element content (%) C41 H 25 N3O: C, 85.54; H, 4.38; N, 7.30. Measured element content (%): C, 85.50; H, 4.35; N, 7.33.

[0296] Synthesis Example 37: Preparation of Compound 616

[0297]

[0298] According to the same preparation method as compound 6 in Synthesis Example 1, b-6 and c-6 were replaced by equimolar amounts of b-616 and c-616, respectively, and the other steps were the same to obtain compound 616 (14.45 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 625.2168; theoretical value: 625.2154). Theoretical element content (%) C 45 H 27 N3O: C, 86.38; H, 4.35; N, 6.72. Measured element content (%): C, 86.36; H, 4.37; N, 6.76.

[0299] Device Embodiment

[0300] The organic materials in the device preparation examples are all purified by sublimation, and the purity is above 99.99%. The ITO glass substrate and ITO / Ag / ITO glass substrate used in the device preparation examples are purchased from the market.

[0301] The following are other compounds used in the device preparation examples except the nitrogen-containing heterocyclic compound described in the present invention:

[0302]

[0303] The test software, computer, K2400 digital source meter of Keithley Company and PR788 spectrum scanning luminance meter of PhotoResearch Company were combined into a combined IVL test system. The device prepared by the present invention was tested at a current density of 10 mA / cm at atmospheric pressure and room temperature. 2 The luminous efficiency and driving voltage at the time of the test were 10 mA / cm2. The life of the device prepared by the present invention was tested using the M6000 OLED life test system of McScience Company at atmospheric pressure and room temperature (brightness decayed to 95% of the initial brightness). The current density during the test was 10 mA / cm2. 2 .

[0304] Device Example 1: Preparation of Green Organic Electroluminescent Device

[0305] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0306] The following layers are deposited layer by layer on the above ITO / Ag / ITO glass substrate: a. HT-1 and P-1 (mass ratio is 97:3) as hole injection layer, and the evaporated film thickness is 60nm. b. HT-1 is used as hole transport layer, and the evaporated film thickness is 55nm. c. EB-1 is used as electron blocking layer, and the evaporated film thickness is 10nm. d. GH-1 is used as the first host material, GH-2 is used as the second host material, and GD-1 is used as the guest material (mass ratio is 47:47:6), and the light-emitting layer thickness is 30nm. e. Compound 6 and Liq (mass ratio is 1:1) are used as electron transport layer, and the evaporated film thickness is 35nm. f. LiF layer is used as electron injection layer, and the evaporated film thickness is 1nm. g. The mass ratio of Mg and Ag is 1:9, and the evaporated film thickness is 15nm. h. CP-1 is used as covering layer, and the evaporated film thickness is 65nm.

[0307] Device Example 2 to Device Example 37: Preparation of Green Organic Electroluminescent Device

[0308] Compound 7, compound 21, compound 23, compound 25, compound 47, compound 49, compound 50, compound 64, compound 68, compound 71, compound 95, compound 107, compound 117, compound 119, compound 126, compound 138, compound 142, compound 161, compound 197, compound 208, compound 227, compound 236, compound 266, compound 275, compound 288, compound 313, compound 326, compound 380, compound 387, compound 401, compound 414, compound 439, compound 455, compound 489, compound 579, and compound 616 of the present invention are used to replace compound 6 in device embodiment 1 as an electron transport layer, and the rest of the preparation process is exactly the same to prepare an organic electroluminescent device.

[0309] Comparative Device Examples 1 to 4:

[0310] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and Comparative Compound 4 were used to replace Compound 6 in Device Example 1 as the electron transport layer, and the rest of the preparation process was exactly the same to prepare an organic electroluminescent device.

[0311] Table 1: Test data of luminescent characteristics of organic electroluminescent devices prepared in device examples 1 to 37 and comparative device examples 1 to 4

[0312]

[0313]

[0314] According to the results in Table 1, the nitrogen-containing heterocyclic compound of the present invention has a high electron mobility, which can improve the combination efficiency of holes and electrons, thereby improving the luminous efficiency of the organic electroluminescent device.

[0315] Device Example 38: Preparation of Green Organic Electroluminescent Device

[0316] First, ITO / Ag / ITO was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0317] The following layers are deposited layer by layer on the above ITO / Ag / ITO: a. HT-1 and P-1 (mass ratio of 97:3) are used as hole injection layer, and the evaporated film thickness is 60nm. b. HT-1 is used as hole transport layer, and the evaporated film thickness is 50nm. c. EB-1 is used as electron blocking layer, and the evaporated film thickness is 15nm. d. GH-1 is used as the first host material, GH-2 is used as the second host material, and GD-1 is used as the guest material (mass ratio of 47:47:6), and the film thickness of the light-emitting layer is 25nm. e. Compound 6 is used as a hole blocking layer, and the evaporated film thickness is 10nm. f. ET-1 and Liq (mass ratio of 1:1) are used as electron transport layer, and the evaporated film thickness is 40nm. g. LiF layer is used as electron injection layer, and the evaporated film thickness is 1nm. h. The mass ratio of Mg and Ag is 1:9, and the evaporated film thickness is 15nm. i. CP-1 is used as the cover layer, and the thickness of the evaporated film is 65nm.

[0318] Device Examples 39 to 74: Preparation of Green Organic Electroluminescent Devices

[0319] Compound 7, compound 21, compound 23, compound 25, compound 47, compound 49, compound 50, compound 64, compound 68, compound 71, compound 95, compound 107, compound 117, compound 119, compound 126, compound 138, compound 142, compound 161, compound 197, compound 208, compound 227, compound 236, compound 266, compound 275, compound 288, compound 313, compound 326, compound 380, compound 387, compound 401, compound 414, compound 439, compound 455, compound 489, compound 579, and compound 616 of the present invention are used to replace compound 6 in device embodiment 38 as a hole blocking layer, and the rest of the preparation process is exactly the same to prepare an organic electroluminescent device.

[0320] Comparative device embodiments 5 to 8:

[0321] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and Comparative Compound 4 were used to replace Compound 6 in Device Example 38 as the hole blocking layer, and the rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0322] Table 2: Test data of luminescent characteristics of the organic electroluminescent devices prepared in device examples 38 to 74 and comparative device examples 5 to 8

[0323]

[0324]

[0325] According to the results in Table 2, the nitrogen-containing heterocyclic compound of the present invention can effectively block the migration of holes to the electron transport layer, reduce the electron injection and transport barrier, reduce the driving voltage, and extend the service life of the device.

[0326] Device Example 75: Preparation of Green Organic Electroluminescent Device

[0327] First, ITO / Ag / ITO was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0328] The following layers are deposited layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a. HT-2 and P-1 (mass ratio is 97:3) as hole injection layer, and the evaporated film thickness is 60nm. b. HT-2 is used as hole transport layer, and the evaporated film thickness is 50nm. c. EB-1 is used as electron blocking layer, and the evaporated film thickness is 10nm. d. Compound 6 is used as the first host material, GH-2 is used as the second host material, GD-1 is used as the guest material (mass ratio is 47:47:6), and the light-emitting layer thickness is 30nm. e. ET-1 and Liq (mass ratio is 1:1) are used as electron transport layer, and the evaporated film thickness is 45nm. f. LiF layer is used as electron injection layer, and the evaporated film thickness is 1nm. g. The mass ratio of Mg and Ag is 1:9, and the evaporated film thickness is 15nm. h. CP-1 is used as covering layer, and the evaporated film thickness is 65nm.

[0329] Device Examples 76 to 111: Preparation of Green Organic Electroluminescent Devices

[0330] Compound 7, compound 21, compound 23, compound 25, compound 47, compound 49, compound 50, compound 64, compound 68, compound 71, compound 95, compound 107, compound 117, compound 119, compound 126, compound 138, compound 142, compound 161, compound 197, compound 208, compound 227, compound 236, compound 266, compound 275, compound 288, compound 313, compound 326, compound 380, compound 387, compound 401, compound 414, compound 439, compound 455, compound 489, compound 579, and compound 616 of the present invention are used as the main material to replace compound 6 in device embodiment 75, and the rest of the preparation process is exactly the same to prepare an organic electroluminescent device.

[0331] Comparative device embodiments 9 to 12:

[0332] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 and Comparative Compound 4 were used to replace Compound 6 in Device Example 75 as the first main material, and the rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0333] Table 3: Test data of luminescent characteristics of the organic electroluminescent devices prepared in device examples 75 to 111 and comparative device examples 9 to 12

[0334]

[0335]

[0336] According to the results in Table 3, when the nitrogen-containing heterocyclic compound of the present invention is used as the first host material, it has a good match with the triplet energy level of the guest material and can effectively improve the luminescence efficiency of the device.

[0337] Device Example 112: Preparation of Green Organic Electroluminescent Device

[0338] First, ITO / Ag / ITO was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0339] The following layers are deposited layer by layer on the above ITO / Ag / ITO: a. HT-1 and P-1 (mass ratio is 97:3) as hole injection layer, the evaporated film thickness is 10nm. b. HT-1 as hole transport layer, the evaporated film thickness is 100nm. c. EB-1 as electron blocking layer, the evaporated film thickness is 10nm. d. GH-1 as the first host material, GH-2 as the second host material, GD-1 as the guest material (mass ratio is 47:47:6), the light-emitting layer thickness is 20nm. e. ET-1 and Liq (mass ratio is 1:1) as electron transport layer, the evaporated film thickness is 20nm. f. Evaporated N-type charge generation layer (n-CGL layer), its structure is Yb: compound 6 (the doping ratio of Yb is 5% by mass), the film thickness is 15nm. g. HT-1 and TCNQ (mass ratio of 9:1) are evaporated to form a P-type charge generation layer with a film thickness of 10nm. h. HT-1 is further vacuum deposited to form a hole transport layer with an evaporation thickness of 100nm. i. EB-1 is used as an electron blocking layer with an evaporation thickness of 10nm. j. GH-1 is used as the first host material, GH-2 is used as the second host material, and GD-1 is used as the guest material (mass ratio of 47:47:6), and the film thickness of the light-emitting layer is 20nm. k. HB-1 is used as a hole blocking layer with an evaporation thickness of 5nm. l. ET-1 and Liq (mass ratio of 1:1) are used as electron transport layers with an evaporation thickness of 20nm. m. LiF layer is used as an electron injection layer with an evaporation thickness of 1nm. n. The mass ratio of Mg and Ag is 1:9, and the evaporation thickness is 15nm. o. CP-1 is used as a capping layer with a thickness of 65nm.

[0340] Device Examples 113 to 148: Preparation of Blue Organic Electroluminescent Devices

[0341] Compound 7, compound 21, compound 23, compound 25, compound 47, compound 49, compound 50, compound 64, compound 68, compound 71, compound 95, compound 107, compound 117, compound 119, compound 126, compound 138, compound 142, compound 161, compound 197, compound 208, compound 227, compound 236, compound 266, compound 275, compound 288, compound 313, compound 326, compound 380, compound 387, compound 401, compound 414, compound 439, compound 455, compound 489, compound 579, and compound 616 of the present invention are used to replace compound 6 in device embodiment 112 as the CGL layer, and the rest of the production process is exactly the same to prepare an organic electroluminescent device.

[0342] Comparative device embodiment 13:

[0343] An organic electroluminescent device was prepared by using Compound 6 in Example 112 as the n-CGL layer instead of CGL-1 and following the same other manufacturing processes.

[0344] Table 4: Test data of luminescence characteristics of the organic electroluminescent devices prepared in device examples 112 to 148 and comparative device example 13

[0345]

[0346]

[0347] According to the results in Table 4, when the compound of the present invention is used as a CGL material in a stacked device, the device voltage decreases, and the device efficiency and device life are improved compared to the comparative material, which further demonstrates that the compound of the present invention has good technical effects when used as a CGL material in a stacked OLED device.

[0348] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A nitrogen-containing heterocyclic compound, characterized in that The nitrogen-containing heterocyclic compound has a structure represented by Formula I: Said Y is selected from O or S; The z is independently selected from CH or N; The R1 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring; The q is selected from 0, 1, 2, 3, 4 or 5; The ring A is selected from any one of the following groups: The T is independently selected from CH or N; The R2 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring; The t1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2 or 3; the t4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t5 is selected from 0, 1, 2, 3 or 4; the t6 is selected from 0, 1, 2, 3, 4 or 5; The x is independently selected from C(R3) or N, and at least one x is a N atom; The R3 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring; The Ar1 is selected from any one of the following groups: The G is independently selected from CH or N; The s0 is selected from 1, 2 or 3; The ring W is selected from a substituted or unsubstituted C3-C30 alicyclic ring; The G1 is selected from O, S or N (Rk); The M is selected from O or S; The Rd is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C12 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring; The Rk and Rg are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring; The m0 is selected from 0, 1, 2, 3, 4 or 5; the m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m3 is selected from 0, 1, 2, 3 or 4; the m4 is selected from 0, 1, 2 or 3. The L1 is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group; The condition is that when ring A is When , L1 is not a single bond; The L2 and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, and a substituted or unsubstituted C2-C30 heteroarylene group.

2. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The nitrogen-containing heterocyclic compound is selected from any one of the structures represented by the following formula II-1 to formula II-7: The definitions of Ar1, ring A, L1, L2, L3, R1, R3, Y, z, and q are the same as those in Formula I; The h1 is selected from 0, 1 or 2.

3. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that Said Any one selected from the following groups: The R1 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothiophenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl; The q0 is selected from 0, 1, 2, 3, 4 or 5; the q1 is selected from 0, 1, 2, 3 or 4; the q2 is selected from 0, 1, 2 or 3; and the q3 is selected from 0, 1 or 2.

4. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The ring A is selected from any one of the following groups: The R2 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, dibenzofuranyl, dibenzothienyl, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring; In the "substituted or unsubstituted" mentioned above, the substituent is selected from deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, deuterated phenyl, methylphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl; when there are two or more substituents, the two or more substituents are the same or different from each other; The t1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2 or 3; the t4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t5 is selected from 0, 1, 2, 3 or 4; the t6 is selected from 0, 1, 2, 3, 4 or 5; the t7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t8 is selected from 0, 1 or 2.

5. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups: The Rd is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl, or two adjacent Rd are connected to each other to form a substituted or unsubstituted ring; The Rg is selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl; In the "substituted or unsubstituted" mentioned above, the substituent is selected from deuterium, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, phenyl, biphenyl, deuterated phenyl, methylphenyl, naphthyl, pyridyl, pyrimidyl, benzofuranyl, benzothienyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, dibenzofuranyl, dibenzothienyl; when there are two or more substituents, the two or more substituents are the same or different from each other; wherein a1 is selected from 0, 1, 2, 3, 4 or 5; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1, 2 or 3; a4 is selected from 0, 1 or 2; a5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a7 is selected from 0, 1, 2, 3, 4, 5 or 6; and a8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

6. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The L1 is selected from a single bond or any one of the following groups: The R4 is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent R4 are connected to each other to form a substituted or unsubstituted ring; The Rp and Rq are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or adjacent Rp and Rq are connected to form a substituted or unsubstituted spiro ring; The r1 is selected from 0, 1, 2, 3 or 4, the r2 is selected from 0, 1, 2 or 3, and the r3 is selected from 0, 1 or 2.

7. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The L2 and L3 are independently selected from a single bond or any one of the following groups: The Rn is independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or two adjacent Rn are connected to each other to form a substituted or unsubstituted ring; The Rw and Rz are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring, or adjacent Rw and Rz are connected to form a substituted or unsubstituted spiro ring; The b1 is selected from 0, 1, 2, 3 or 4, the b2 is selected from 0, 1, 2 or 3, and the b3 is selected from 0, 1 or 2.

8. The nitrogen-containing heterocyclic compound according to claim 1, characterized in that The nitrogen-containing heterocyclic compound is selected from any one of the following compounds:

9. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer located between the anode and the cathode or located outside at least one of the anode and the cathode, characterized in that: The organic functional layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 8.

10. A stacked organic electroluminescent device, comprising an anode, a cathode, a first light-emitting unit, a second light-emitting unit and a charge generation layer, wherein the first light-emitting unit, the second light-emitting unit and the charge generation layer are located between the anode and the cathode, and the charge generation layer is located between the first light-emitting unit and the second light-emitting unit, characterized in that: The charge generation layer comprises any one or more of the nitrogen-containing heterocyclic compounds according to any one of claims 1 to 8.

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