Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic photoelectric materials. When the heterocyclic compound provided by the invention is used as an electron transport layer material, the heterocyclic compound has relatively high electron mobility, and the combination efficiency of holes and electrons can be improved; when being used as a main body material, the organic electroluminescent material has a relatively high triplet state energy level, so that the organic electroluminescent device has relatively high luminous efficiency; when the material is used as a covering layer material, the service life of a device can be effectively prolonged.

Description

Technical Field

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

[0002] Organic Light-Emitting Diode (OLED), also known as organic light-emitting diode, has the advantages of being lighter, brighter, lower energy consumption, faster response, higher definition, wider viewing angle, better flexibility, and higher luminous efficiency. Based on the above advantages, OLED technology has gradually become a research hotspot in the scientific research and industry circles.

[0003] The structure of traditional organic electroluminescent devices is mostly sandwich-shaped, mainly including anode, cathode, hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), light-emitting layer, hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL) and capping layer (CP). When a certain DC bias is applied to the device, holes are injected from the anode and transferred to the light-emitting layer through the highest occupied molecular orbital (HOMO), while electrons are injected from the cathode and transferred to the light-emitting layer through the lowest unoccupied molecular orbital (LUMO). After the electrons and holes recombine in the light-emitting layer, excitons are generated. When the excitons release energy in the form of light radiation, it is the electroluminescence of the light-emitting device.

[0004] In order to improve the luminous efficiency and service life of organic electroluminescent devices, it is necessary to reasonably design materials and device structures. For example, electron transport materials need to have a high electron mobility; a "covering layer" material with a high refractive index is arranged on the outside of a semi-transparent electrode with a low refractive index to improve the performance of OLED devices. However, the electron mobility of most electron transport materials is not high enough, and the refractive index and glass transition temperature of the covering layer are low. Therefore, how to develop electron transport materials and covering layer materials with better performance has always been a problem that technicians in this field need to solve urgently. Summary of the invention

[0005] The present invention aims to solve the problems of high driving voltage, low luminous efficiency and short service life of organic electroluminescent devices, and provides a 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 heterocyclic compound having a structure represented by Formula I:

[0007]

[0008] The Ar1 and Ar2 are independently selected from Formula 1;

[0009] Said Y is selected from O or S;

[0010] The v is independently selected from CH or N;

[0011] 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0012] The q is selected from 0, 1, 2, 3, 4 or 5;

[0013] Said y is independently selected from C(R2) or N, and when y is N, at most 2 y are N atoms;

[0014] 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-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0015] The x is independently selected from CH or N;

[0016] The n1 is selected from 0, 1 or 2; the n2 is selected from 0, 1 or 2;

[0017] The Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, or the two adjacent Ra and two Rb are connected to each other to form a substituted or unsubstituted C3-C6 ring;

[0018] The f is selected from 0, 1, 2, 3 or 4; the t is selected from 0, 1, 2, 3 or 4;

[0019] The R0 is independently selected from 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-C12 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group or any one of the following groups:

[0020]

[0021] The Gs are independently selected from CH or N, and at least one G is selected from N;

[0022] Said Q is independently selected from CH or N;

[0023] The M is selected from O or S;

[0024] The K is selected from O, S or N(Rf)

[0025] 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-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;

[0026] The Rf is selected from any one of hydrogen, deuterium, cyano, 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0027] The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c5 is selected from 0, 1, 2 or 3;

[0028] When R0 is selected from substituted or unsubstituted C6-C12 aryl, the substituent is selected from 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-C12 aryl, substituted or unsubstituted C2-C12 monocyclic heteroaryl, substituted or unsubstituted C2-C12 polycyclic heteroaryl, substituted or unsubstituted C2-C12 fused heteroaryl containing at least one heteroatom of O, S, Si, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group, or any one of the following groups;

[0029] The u is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0030] The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic group and a C6-C30 aromatic ring condensed ring group;

[0031] The condition is that v, y, x, L1, and L2 contain at least one N atom.

[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 on the side of the cathode away from the anode, characterized in that the organic functional layer contains any one or more of the heterocyclic compounds described in the present invention.

[0033] Beneficial effects:

[0034] When the heterocyclic compound provided by the present invention is used as an electron transport layer material, it has a high electron mobility and can improve the combination efficiency of holes and electrons; when it is used as a main material, it has a high triplet energy level, so that the organic electroluminescent device has a high luminous efficiency; when it is used as a covering layer material, it can effectively improve the service life of the device.

[0035] In summary, the heterocyclic compounds provided by the present invention are a class of OLED materials with excellent performance. DETAILED DESCRIPTION

[0036] 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.

[0037] 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.

[0038] The halogen mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] The sub-fused cyclic group of an alicyclic ring and an aromatic ring of the present invention refers to a divalent group formed by removing two hydrogen atoms after an alicyclic ring and an aromatic ring are fused together. The above description of the fused cyclic group of an alicyclic ring and an aromatic ring can be applied to it, except that the sub-fused cyclic group of an alicyclic ring and an aromatic ring 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 heterocyclic compound having a structure represented by Formula I:

[0056]

[0057] The Ar1 and Ar2 are independently selected from Formula 1;

[0058] Said Y is selected from O or S;

[0059] The v is independently selected from CH or N;

[0060] 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0061] The q is selected from 0, 1, 2, 3, 4 or 5;

[0062] Said y is independently selected from C(R2) or N, and when y is N, at most 2 y are N atoms;

[0063] 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-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0064] The x is independently selected from CH or N;

[0065] The n1 is selected from 0, 1 or 2; the n2 is selected from 0, 1 or 2;

[0066] The Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, or the two adjacent Ra and two Rb are connected to each other to form a substituted or unsubstituted C3-C6 ring;

[0067] The f is selected from 0, 1, 2, 3 or 4; the t is selected from 0, 1, 2, 3 or 4;

[0068] The R0 is independently selected from 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-C12 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group or any one of the following groups:

[0069]

[0070] The Gs are independently selected from CH or N, and at least one G is selected from N;

[0071] Said Q is independently selected from CH or N;

[0072] The M is selected from O or S;

[0073] The K is selected from O, S or N(Rf);

[0074] 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-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;

[0075] The Rf is selected from any one of hydrogen, deuterium, cyano, 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0076] The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c5 is selected from 0, 1, 2 or 3;

[0077] When R0 is selected from substituted or unsubstituted C6-C12 aryl, the substituent is selected from 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-C12 aryl, substituted or unsubstituted C2-C12 monocyclic heteroaryl, substituted or unsubstituted C2-C12 polycyclic heteroaryl, substituted or unsubstituted C2-C12 fused heteroaryl containing at least one heteroatom of O, S, Si, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group, or any one of the following groups;

[0078] The u is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0079] The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic group and a C6-C30 aromatic ring condensed ring group;

[0080] The condition is that v, y, x, L1, and L2 contain at least one N atom.

[0081] Preferably, the heterocyclic compound has any one of the structures represented by Formula II-1 to Formula II-4:

[0082]

[0083]

[0084] The definitions of Ar1, Ar2, L1, L2, R2, Ra, Rb, R0, f, t, n1, n2, and u are the same as those in Formula I;

[0085] The p0 is selected from 0, 1, 2 or 3; the p1 is selected from 0, 1 or 2.

[0086] More preferably, the heterocyclic compound has any one of the structures represented by Formula III-1 to Formula III-5:

[0087]

[0088] Preferably, the formula 1 is selected from any one of the following groups:

[0089]

[0090] The R1 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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;

[0091] 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.

[0092] Preferably, R0 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, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, or any one of the following groups:

[0093]

[0094]

[0095]

[0096] The R3 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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, benzothiophenyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexane, dibenzofuranyl, dibenzothiophenyl;

[0097] The Rf is selected from hydrogen, deuterium, cyano, 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, benzocyclohexyl, dibenzofuranyl, dibenzothiophenyl;

[0098] The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c5 is selected from 0, 1, 2 or 3; the c6 is selected from 0, 1 or 2; the c7 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0099] Preferably, when n1 and n2 are both 0, the is selected from a single bond, when n1 and n2 are not 0 at the same time, the Any one selected from the following groups:

[0100]

[0101]

[0102] The Ra, Rb, and Rc are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, and iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, and triphenylsilyl;

[0103] The f is selected from 0, 1, 2, 3 or 4; the f2 is selected from 0, 1 or 2; the f3 is selected from 0, 1, 2 or 3;

[0104] The t is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1 or 2; the t3 is selected from 0, 1, 2 or 3;

[0105] The r1 is selected from 0, 1 or 2; the r2 is selected from 0, 1, 2, 3 or 4; the r3 is selected from 0, 1, 2, 3, 4, 5 or 6; the r4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0106] Preferably, L1 and L2 are independently selected from a single bond or any one of the following groups:

[0107]

[0108] The z is independently selected from CH or N;

[0109] The s0 is selected from 1, 2 or 3;

[0110] The T is selected from O, S or N(Rg);

[0111] The ring W is selected from a substituted or unsubstituted C3-C30 alicyclic ring;

[0112] 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group;

[0113] 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 ring;

[0114] The Rg is 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;

[0115] The b1 is selected from 0, 1, 2, 3 or 4; the b2 is selected from 0, 1, 2 or 3; the b3 is selected from 0, 1 or 2; and the b4 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0116] Preferably, L1 and L2 are independently selected from a single bond or any one of the following groups:

[0117]

[0118] The Rn is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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;

[0119] Said Rw, Rz are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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;

[0120] 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;

[0121] The b1 is selected from 0, 1, 2, 3 or 4; the b2 is selected from 0, 1, 2 or 3; the b3 is selected from 0, 1 or 2; the b4 is selected from 0, 1, 2, 3, 4, 5 or 6; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0122] More preferably, L1 and L2 are independently selected from a single bond or any one of the following groups:

[0123]

[0124] Preferably, the compound satisfies at least one of the following conditions:

[0125] i. The compound has any one of the structures represented by formula II-2 to formula II-4, formula III-2 to formula III-5

[0126] ii. The formula 1 is selected from any one of the following groups:

[0127]

[0128]

[0129] iii. Any one selected from the following groups:

[0130] iv. The L1 or L2 is selected from any one of the following groups:

[0131]

[0132] Most preferably, the heterocyclic compound is selected from one of the following compounds:

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] The above lists only some specific structural forms of the 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.

[0160] The heterocyclic compound represented by formula I of the present invention can be prepared by one of the following synthetic routes:

[0161]

[0162] 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.

[0163] The Xc, Xd and Xe are independently selected from I, Br or Cl.

[0164] Alternatively, the order of the above reactions may be changed to obtain the heterocyclic compound represented by formula I of the present invention.

[0165] 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 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.

[0166] 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 heterocyclic compounds described in the present invention.

[0167] Preferably, the organic functional layer may be one or more, and the organic functional layer is located between the anode and the cathode or on the side of the cathode away from the anode. As the organic functional layer comprising the aforementioned compound, there can be cited 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 (covering layer, light efficiency improvement layer, sealing layer, etc.) disposed outside the cathode, but not limited thereto.

[0168] 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 heterocyclic compounds described in the present invention.

[0169] 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 electron transport region is located between the light-emitting layer and the cathode, and the electron transport region contains any one or more of the heterocyclic compounds of the present invention.

[0170] 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 heterocyclic compounds described in the present invention.

[0171] Preferably, the organic functional layer comprises an electron transport layer, and the electron transport layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0172] Preferably, the organic functional layer comprises a hole blocking layer, and the hole blocking layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0173] 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 light-emitting layer contains any one or more of the heterocyclic compounds of the present invention.

[0174] 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 heterocyclic compounds described in the present invention.

[0175] Preferably, the organic functional layer is located on a side of the cathode away from the anode, and the organic functional layer comprises any one or more of the heterocyclic compounds of the present invention.

[0176] More preferably, the organic functional layer includes a covering layer, and the covering layer comprises any one or more of the heterocyclic compounds described in the present invention.

[0177] 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 heterocyclic compounds described in the present invention.

[0178] 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 heterocyclic compounds described in the present invention.

[0179] 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:

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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.

[0184] 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 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,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), etc., but are not limited thereto.

[0185] 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 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.

[0186] 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 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 heterocyclic compounds of the present invention are preferably selected from the group consisting of bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), bis(8-hydroxyquinoline)zinc (Znq2), but are not limited thereto.

[0187] 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.

[0188] The hole blocking layer of the present invention needs to have good electron transport ability and hole blocking ability, 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, azobenzene derivatives, etc., preferably at least one of the 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 heterocyclic compound described in the present invention is preferred.

[0189] 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 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 heterocyclic compounds described in the present invention are preferred.

[0190] 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.

[0191] The covering layer material of the present invention needs to have a high refractive index, which is helpful to improve the light efficiency of the organic light-emitting device, especially to improve the external light-emitting efficiency. The covering layer material includes but is not limited to the following materials, metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc., preferably at least one of the nitrogen-containing heterocyclic compounds described in the present invention. Specific examples may include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris (8-hydroxyquinoline) aluminum (III) (Alq3), N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), 4, 4'-di (9-carbazole) biphenyl (simple CBP), etc., but are not limited thereto. The heterocyclic compound described in the present invention is preferred.

[0192] 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, azobenzene 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 heterocyclic compound described in the present invention is preferred.

[0193] 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.

[0194] 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.

[0195] The technical scheme and technical effects of the present invention are further illustrated below with reference to embodiments and comparative examples.

[0196] 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;

[0197] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar of Germany, with a sample mass of 5 to 10 mg.

[0198] Synthesis Example 1: Preparation of Intermediate c-826

[0199]

[0200] Synthesis of intermediate c-826

[0201] Under nitrogen protection, e-826 (22.01 g, 80 mmol), biboronic acid pinacol ester (20.32 g, 80 mmol), potassium acetate (15.70 g, 160 mmol) and 400 mL N, N-dimethylformamide solution were added to the reaction bottle. After nitrogen replaced the air 3 times, DPPF palladium dichloride (0.59 g, 0.8 mmol) was added, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the reactant was cooled to room temperature, distilled water was added, and the mixture was extracted with ethyl acetate (500 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 with toluene / ethanol (5:1) to obtain c-826 (20.88 g, yield 81%), HPLC purity ≧ 99.88%. Mass spectrum m / z: 322.1480 (theoretical value: 322.1489). Theoretical element content (%) C 18 H 19 BN2O3: C, 67.11; H, 5.94; N, 8.70. Measured element content (%): C, 67.14; H, 5.98; N, 8.75.

[0202] According to the above method, the raw material e-828 in the following table was used to replace the raw material e-826 in Synthesis Example 1 to synthesize the intermediate c-828:

[0203]

[0204] According to the above method, the raw material a-830 was synthesized by using the raw material f-830 in the following table instead of the raw material e-826 in Synthesis Example 1:

[0205]

[0206] Synthesis Example 2: Preparation of Compound 2

[0207]

[0208] Synthesis of intermediate A-2

[0209] Under nitrogen protection, a-2 (16.51 g, 50.00 mmol), b-2 (11.34 g, 50.00 mmol), potassium phosphate (21.23 g, 100.00 mmol), tetrakis(triphenylphosphine)palladium (1.16 g, 1 mmol), 200 mL toluene, 150 mL ethanol, and 150 mL water were added to the reaction bottle, and the mixture was stirred under reflux for 3.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered, and washed with distilled water. The solid was then recrystallized from toluene / ethanol (10:1) to obtain intermediate A-2 (12.26 g, yield 70%); HPLC detected the solid purity ≧99.86%. Mass spectrum m / z: 349.0410 (theoretical value: 349.0425).

[0210] Synthesis of compound 2

[0211] Under nitrogen protection, A-2 (10.51 g, 30.00 mmol), c-2 (15.49 g, 60.00 mmol), potassium carbonate (12.44 g, 90.00 mmol), tetrakis(triphenylphosphine)palladium (2.08 g, 1.80 mmol), 150 mL toluene, 50 mL ethanol, and 50 mL water were added to the reaction bottle, and the mixture was stirred under reflux for 5 hours. After the reaction, the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized with toluene to obtain compound 2 (11.04 g, yield 68%); HPLC detected the solid purity to be ≧99.96%. Mass spectrum m / z: 541.2054 (theoretical value: 541.2042). Theoretical element content (%) C 39 H 27NO2: C, 86.48; H, 5.02; N, 2.59. Measured element content (%): C, 86.46; H, 5.00; N, 2.55.

[0212] Synthesis Example 3: Preparation of Compound 10

[0213]

[0214] According to the same preparation method as compound 2 in Synthesis Example 2, c-2 was replaced by an equal molar amount of c-10, and the other steps were the same to obtain compound 10 (10.79 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 513.1738; theoretical value: 513.1729). Theoretical element content (%) C 37 H 23 NO2: C, 86.53; H, 4.51; N, 2.73. Measured element content (%): C, 86.50; H, 4.54; N, 2.77.

[0215] Synthesis Example 4: Preparation of Compound 12

[0216]

[0217] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-12 and c-10 respectively, and the other steps were the same to obtain compound 12 (11.62 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 569.2341; theoretical value: 569.2355). Theoretical element content (%) C 41 H 31 NO2: C, 86.44; H, 5.48; N, 2.46. Measured element content (%): C, 86.40; H, 5.44; N, 2.44.

[0218] Synthesis Example 5: Preparation of Compound 16

[0219]

[0220] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-16, b-16, and c-10, respectively, and the other steps were the same to obtain compound 16 (10.63 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 513.1739; theoretical value: 513.1729). Theoretical element content (%) C 37 H 23NO2: C, 86.53; H, 4.51; N, 2.73. Measured element content (%): C, 86.57; H, 4.56; N, 2.70.

[0221] Synthesis Example 6: Preparation of Compound 38

[0222]

[0223] According to the same preparation method as compound 2 in Synthesis Example 2, c-2 was replaced by an equal molar amount of c-38, and the other steps were the same to obtain compound 38 (13.42 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 667.2270; theoretical value: 667.2260). Theoretical element content (%) C 47 H 29 N3O2: C, 84.54; H, 4.38; N, 6.29. Measured element content (%): C, 84.50; H, 4.33; N, 6.26.

[0224] Synthesis Example 7: Preparation of Compound 44

[0225]

[0226] According to the same preparation method as compound 2 in Synthesis Example 2, c-2 was replaced with an equal molar amount of c-44, and the other steps were the same to obtain compound 44 (13.58 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 665.2340; theoretical value: 665.2355). Theoretical element content (%) C 49 H 31 NO2: C, 88.40; H, 4.69; N, 2.10. Measured element content (%): C, 88.44; H, 4.66; N, 2.12.

[0227] Synthesis Example 8: Preparation of Compound 69

[0228]

[0229] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-69 and c-10 respectively, and the other steps were the same to obtain compound 69 (12.21 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 589.2030; theoretical value: 589.2042). Theoretical element content (%) C 43 H 27NO2: C, 87.58; H, 4.62; N, 2.38. Measured element content (%): C, 87.55; H, 4.64; N, 2.36.

[0230] Synthesis Example 9: Preparation of Compound 76

[0231]

[0232] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-76 and c-10 respectively, and the other steps were the same to obtain compound 76 (12.03 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 589.2058; theoretical value: 589.2042). Theoretical element content (%) C 43 H 27 NO2: C, 87.58; H, 4.62; N, 2.38. Measured element content (%): C, 87.56; H, 4.60; N, 2.34.

[0233] Synthesis Example 10: Preparation of Compound 89

[0234]

[0235] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-69 and c-89, respectively, and the other steps were the same to obtain compound 89 (11.85 g). The solid purity was ≥99.93% by HPLC. Mass spectrum m / z: (measured value: 589.2056; theoretical value: 589.2042). Theoretical element content (%) C 43 H 27 NO2: C, 87.58; H, 4.62; N, 2.38. Measured element content (%): C, 87.55; H, 4.64; N, 2.34.

[0236] Synthesis Example 11: Preparation of Compound 91

[0237]

[0238] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-91 and c-91, respectively, and the other steps were the same to obtain compound 91 (11.68 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 589.2057; theoretical value: 589.2042). Theoretical element content (%) C 43 H 27NO2: C, 87.58; H, 4.62; N, 2.38. Measured element content (%): C, 87.54; H, 4.67; N, 2.36.

[0239] Synthesis Example 12: Preparation of Compound 102

[0240]

[0241] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-91 and c-102 respectively, and the other steps were the same to obtain compound 102 (14.47 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 741.2650; theoretical value: 741.2668). Theoretical element content (%) C 55 H 35 NO2: C, 89.04; H, 4.76; N, 1.89. Measured element content (%): C, 89.08; H, 4.74; N, 1.87.

[0242] Synthesis Example 13: Preparation of Compound 122

[0243]

[0244] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-122 and c-10 respectively, and the other steps were the same to obtain compound 122 (10.34 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: (measured value: 514.1692; theoretical value: 514.1681). Theoretical element content (%) C 36 H 22 N2O2: C, 84.03; H, 4.31; N, 5.44. Measured element content (%): C, 84.06; H, 4.35; N, 5.42.

[0245] Synthesis Example 14: Preparation of Compound 131

[0246]

[0247] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-131 and c-131 respectively, and the other steps were the same to obtain compound 131 (10.38 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 516.1570; theoretical value: 516.1586). Theoretical element content (%) C 34 H 20N4O2: C, 79.06; H, 3.90; N, 10.85. Measured element content (%): C, 79.01; H, 3.94; N, 10.83.

[0248] Synthesis Example 15: Preparation of Compound 159

[0249]

[0250] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-159 and c-10 respectively, and the other steps were the same to obtain compound 159 (10.52 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 515.1620; theoretical value: 515.1634). Theoretical element content (%) C 35 H 21 N3O2: C, 81.54; H, 4.11; N, 8.15. Measured element content (%): C, 81.50; H, 4.13; N, 8.18.

[0251] Synthesis Example 16: Preparation of Compound 166

[0252]

[0253] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-166 and c-10 respectively, and the other steps were the same to obtain compound 166 (14.97 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 744.2518; theoretical value: 744.2525). Theoretical element content (%) C 52 H 32 N4O2: C, 83.85; H, 4.33; N, 7.52. Measured element content (%): C, 83.80; H, 4.36; N, 7.56.

[0254] Synthesis Example 17: Preparation of Compound 183

[0255]

[0256] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-183 and c-44, respectively, and the other steps were the same to obtain compound 183 (13.22 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 667.2270; theoretical value: 667.2260). Theoretical element content (%) C 47 H 29N3O2: C, 84.54; H, 4.38; N, 6.29. Measured element content (%): C, 84.51; H, 4.35; N, 6.27.

[0257] Synthesis Example 18: Preparation of Compound 195

[0258]

[0259] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-195 and c-195, respectively, and the other steps were the same to obtain compound 195 (12.03 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 589.2049; theoretical value: 589.2042). Theoretical element content (%) C 43 H 27 NO2: C, 87.58; H, 4.62; N, 2.38. Measured element content (%): C, 87.56; H, 4.65; N, 2.34.

[0260] Synthesis Example 19: Preparation of Compound 196

[0261]

[0262] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-196 and c-89, respectively, and the other steps were the same to obtain compound 196 (10.48 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 513.1720; theoretical value: 513.1729). Theoretical element content (%) C 37 H 23 NO2: C, 86.53; H, 4.51; N, 2.73. Measured element content (%): C, 86.57; H, 4.53; N, 2.77.

[0263] Synthesis Example 20: Preparation of Compound 216

[0264]

[0265] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-216 and c-10 respectively, and the other steps were the same to obtain compound 216 (12.67 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 639.2180; theoretical value: 639.2198). Theoretical element content (%) C 47 H 29NO2: C, 88.24; H, 4.57; N, 2.19. Measured element content (%): C, 88.20; H, 4.55; N, 2.14.

[0266] Synthesis Example 21: Preparation of Compound 256

[0267]

[0268] According to the same preparation method as compound 2 in Synthesis Example 2, b-2 and c-2 were replaced by equimolar amounts of b-256 and c-10, respectively, and the other steps were the same to obtain compound 256 (10.50 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: (measured value: 514.1692; theoretical value: 514.1681). Theoretical element content (%) C 36 H 22 N2O2: C, 84.03; H, 4.31; N, 5.44. Measured element content (%): C, 84.00; H, 4.35; N, 5.42.

[0269] Synthesis Example 22: Preparation of Compound 317

[0270]

[0271] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-69, b-317, and c-91, respectively, and the other steps were the same to obtain compound 317 (11.87 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 590.1980; theoretical value: 590.1994). Theoretical element content (%) C 42 H 26 N2O2: C, 85.40; H, 4.44; N, 4.74. Measured element content (%): C, 85.43; H, 4.40; N, 4.76.

[0272] Synthesis Example 23: Preparation of Compound 336

[0273]

[0274] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-336, b-317, and c-10, respectively, and the other steps were the same to obtain compound 336 (10.52 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 515.1620; theoretical value: 515.1634). Theoretical element content (%) C 35 H21 N3O2: C, 81.54; H, 4.11; N, 8.15. Measured element content (%): C, 81.53; H, 4.13; N, 8.10.

[0275] Synthesis Example 24: Preparation of Compound 427

[0276]

[0277] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-427, b-427, and c-10, respectively, and the other steps were the same to obtain compound 427 (10.32 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 513.1749; theoretical value: 513.1729). Theoretical element content (%) C 37 H 23 NO2: C, 86.53; H, 4.51; N, 2.73. Measured element content (%): C, 86.57; H, 4.54; N, 2.75.

[0278] Synthesis Example 25: Preparation of Compound 449

[0279]

[0280] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-336, b-427, c-44, respectively, and the other steps were the same to obtain compound 449 (13.58 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 665.2374; theoretical value: 665.2355). Theoretical element content (%) C 49 H 31 NO2: C, 88.40; H, 4.69; N, 2.10. Measured element content (%): C, 88.43; H, 4.65; N, 2.15.

[0281] Synthesis Example 26: Preparation of Compound 463

[0282]

[0283] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-463, b-427, and c-10, respectively, and the other steps were the same to obtain compound 463 (10.65 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 514.1670; theoretical value: 514.1681). Theoretical element content (%) C 36 H 22 N2O2: C, 84.03; H, 4.31; N, 5.44. Measured element content (%): C, 84.06; H, 4.35; N, 5.40.

[0284] Synthesis Example 27: Preparation of Compound 505

[0285]

[0286] According to the same preparation method as compound 2 in Synthesis Example 2, c-2 was replaced with an equal molar amount of c-505, and the other steps were the same to obtain compound 505 (11.46 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 545.1287; theoretical value: 545.1272). Theoretical element content (%) C 37 H 23 NS2: C, 81.44; H, 4.25; N, 2.57. Measured element content (%): C, 81.41; H, 4.20; N, 2.55.

[0287] Synthesis Example 28: Preparation of Compound 535

[0288]

[0289] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-535 and c-505, respectively, and the other steps were the same to obtain compound 535 (12.69 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 621.1570; theoretical value: 621.1585). Theoretical element content (%) C 43 H 27 NS2: C, 83.06; H, 4.38; N, 2.25. Measured element content (%): C, 83.02; H, 4.34; N, 2.20.

[0290] Synthesis Example 29: Preparation of Compound 564

[0291]

[0292] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-122 and c-505 respectively, and the other steps were the same to obtain compound 564 (10.99 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 546.1210; theoretical value: 546.1224). Theoretical element content (%) C 36 H 22 N2S2: C, 79.09; H, 4.06; N, 5.12. Measured element content (%): C, 79.05; H, 4.03; N, 5.10.

[0293] Synthesis Example 30: Preparation of Compound 577

[0294]

[0295] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-122 and c-577 respectively, and the other steps were the same to obtain compound 577 (15.58 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 798.2150; theoretical value 798.2163). Theoretical element content (%) C 56 H 34 N2S2: C, 84.18; H, 4.29; N, 3.51. Measured element content (%): C, 84.16; H, 4.24; N, 3.54.

[0296] Synthesis Example 31: Preparation of Compound 619

[0297]

[0298] According to the same preparation method as compound 2 in Synthesis Example 2, b-2 and c-2 were replaced by equimolar amounts of b-619 and c-10, respectively, and the other steps were the same to obtain compound 619 (10.32 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 513.1740; theoretical value: 513.1729). Theoretical element content (%) C 37 H 23 NO2: C, 86.53; H, 4.51; N, 2.73. Measured element content (%): C, 86.50; H, 4.54; N, 2.77.

[0299] Synthesis Example 32: Preparation of Compound 625

[0300]

[0301] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-195 and c-625, respectively, and the other steps were the same to obtain compound 625 (12.87 g). The solid purity detected by HPLC was ≥99.95%. Mass spectrum m / z: (measured value: 621.1571; theoretical value: 621.1585). Theoretical element content (%) C 43 H 27 NS2: C, 83.06; H, 4.38; N, 2.25. Measured element content (%): C, 83.01; H, 4.34; N, 2.20.

[0302] Synthesis Example 33: Preparation of Compound 686

[0303]

[0304] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-69, b-317, c-505, respectively, and the other steps were the same to obtain compound 686 (12.71 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 622.1530; theoretical value: 622.1537). Theoretical element content (%) C 42 H 26 N2S2: C, 81.00; H, 4.21; N, 4.50. Measured element content (%): C, 81.04; H, 4.25; N, 4.52.

[0305] Synthesis Example 34: Preparation of Compound 729

[0306]

[0307] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-729, b-317, and c-729, respectively, and the other steps were the same to obtain compound 729 (12.44 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 618.1630; theoretical value: 618.1620). Theoretical element content (%) C 39 H 30 N2S2Si: C, 75.69; H, 4.89; N, 4.53. Measured element content (%): C, 75.64; H, 4.86; N, 4.56.

[0308] Synthesis Example 35: Preparation of Compound 749

[0309]

[0310] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-195, b-317, and c-749, respectively, and the other steps were the same to obtain compound 749 (12.52 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 622.1528; theoretical value: 622.1537). Theoretical element content (%) C 42 H 26 N2S2: C, 81.00; H, 4.21; N, 4.50. Measured element content (%): C, 81.02; H, 4.24; N, 4.54.

[0311] Synthesis Example 36: Preparation of Compound 757

[0312]

[0313] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-131, b-427, c-505, respectively, and the other steps were the same to obtain compound 757 (11.30 g). The solid purity detected by HPLC was ≥99.93%. Mass spectrum m / z: (measured value: 545.1260; theoretical value: 545.1272). Theoretical element content (%) C 37 H 23 NS2: C, 81.44; H, 4.25; N, 2.57. Measured element content (%): C, 81.40; H, 4.28; N, 2.55.

[0314] Synthesis Example 37: Preparation of Compound 785

[0315]

[0316] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-122, b-785, c-10, respectively, and the other steps were the same to obtain compound 785 (10.76 g). The solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: (measured value: 527.1899; theoretical value: 527.1885). Theoretical element content (%) C 38 H 25 NO2: C, 86.50; H, 4.78; N, 2.65. Measured element content (%): C, 86.55; H, 4.74; N, 2.67.

[0317] Synthesis Example 38: Preparation of Compound 804

[0318]

[0319] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-804, b-427, c-10, respectively, and the other steps were the same to obtain compound 804 (11.18 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 564.1850; theoretical value: 564.1838). Theoretical element content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured element content (%): C, 85.07; H, 4.26; N, 4.93.

[0320] Synthesis Example 39: Preparation of Compound 823

[0321]

[0322] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-823 and c-10 respectively, and the other steps were the same to obtain compound 823 (10.70 g). The solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: (measured value: 524.2438; theoretical value: 524.2419). Theoretical element content (%) C 37 H 12 D 11 NO2: C, 84.70; H, 6.53; N, 2.67. Measured element content (%): C, 84.73; H, 6.57; N, 2.62.

[0323] Synthesis Example 40: Preparation of Compound 825

[0324]

[0325] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, and c-2 were replaced by equimolar a-825, b-427, and c-825, respectively, and the other steps were the same to obtain compound 825 (10.50 g). The solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: (measured value: 514.1670; theoretical value: 514.1681). Theoretical element content (%) C 36 H 22 N2O2: C, 84.03; H, 4.31; N, 5.44. Measured element content (%): C, 84.06; H, 4.33; N, 5.42.

[0326] Synthesis Example 41: Preparation of Compound 826

[0327]

[0328] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-131, b-427, c-826, respectively, and the other steps were the same to obtain compound 826 (13.48 g). The solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: (measured value: 670.2134; theoretical value: 670.2117). Theoretical element content (%) C 44 H 26 N6O2: C, 78.79; H, 3.91; N, 12.53. Measured element content (%): C, 78.74; H, 3.93; N, 12.57.

[0329] Synthesis Example 42: Preparation of Compound 828

[0330]

[0331] According to the same preparation method as compound 2 in Synthesis Example 2, a-2, b-2, c-2 were replaced by equimolar a-131, b-828, c-828, respectively, and the other steps were the same to obtain compound 828 (13.60 g). The solid purity was ≥99.95% by HPLC. Mass spectrum m / z: (measured value: 676.3030; theoretical value: 676.3045). Theoretical element content (%) C 49 H 20 D 11 NO2: C, 86.95; H, 6.25; N, 2.07. Measured element content (%): C, 86.91; H, 6.29; N, 2.09.

[0332] Synthesis Example 43: Preparation of Compound 829

[0333]

[0334] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-829 and c-10 respectively, and the other steps were the same to obtain compound 829 (11.01 g). The solid purity detected by HPLC was ≥99.94%. Mass spectrum m / z: (measured value: 564.1830; theoretical value: 564.1838). Theoretical element content (%) C 40 H 24 N2O2: C, 85.09; H, 4.28; N, 4.96. Measured element content (%): C, 85.06; H, 4.25; N, 4.92.

[0335] Synthesis Example 44: Preparation of Compound 830

[0336]

[0337] According to the same preparation method as compound 2 in Synthesis Example 2, a-2 and c-2 were replaced by equimolar a-830 and c-10 respectively, and the other steps were the same to obtain compound 830 (10.96 g). The solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: (measured value: 553.2059; theoretical value: 553.2042). Theoretical element content (%) C 40 H 27 NO2: C, 86.78; H, 4.92; N, 2.53. Measured element content (%): C, 86.73; H, 4.97; N, 2.50.

[0338] Device Embodiment

[0339] 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.

[0340] The following are other compounds used in the device preparation examples except the heterocyclic compound described in the present invention:

[0341]

[0342]

[0343] 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 .

[0344] Device Example 1: Preparation of Green Organic Electroluminescent Device

[0345] 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.

[0346] 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 15nm. b. HT-1 is used as hole transport layer, and the evaporated film thickness is 80nm. c. EB-1 is used as electron blocking layer, and the evaporated film thickness is 30nm. 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 35nm. e. Compound 2 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.

[0347] Device Example 2 to Device Example 43: Preparation of Green Organic Electroluminescent Device

[0348] The organic electroluminescent device was prepared by replacing the compound 2 in device embodiment 1 with the compound 10, compound 12, compound 16, compound 38, compound 44, compound 69, compound 76, compound 89, compound 91, compound 102, compound 122, compound 131, compound 159, compound 166, compound 183, compound 195, compound 196, compound 216, compound 256, compound 317, compound 336, compound 427, compound 449, compound 463, compound 505, compound 535, compound 564, compound 577, compound 619, compound 625, compound 686, compound 729, compound 749, compound 757, compound 785, compound 804, compound 823, compound 825, compound 826, compound 828, compound 829 and compound 830 of the present invention as the electron transport layer, and the rest of the preparation process is exactly the same.

[0349] Comparative Device Examples 1 to 7:

[0350] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, Comparative Compound 5, Comparative Compound 6 and Comparative Compound 7 were used to replace Compound 2 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.

[0351] Table 1: Test data of luminescence characteristics of the organic electroluminescent devices prepared in device examples 1 to 43 and comparative device examples 1 to 7

[0352]

[0353]

[0354]

[0355] According to the results in Table 1, the heterocyclic compounds of the present invention have a high electron mobility, which can improve the combination efficiency of holes and electrons, thereby improving the luminous efficiency of organic electroluminescent devices.

[0356] Device Example 44: Preparation of Green Organic Electroluminescent Device

[0357] 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.

[0358] The following layers are deposited layer by layer on the above 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 15nm. b. HT-2 is used as hole transport layer, and the evaporated film thickness is 80nm. c. EB-2 is used as electron blocking layer, and the evaporated film thickness is 35nm. d. Compound 2 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 40nm. e. ET-1 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.

[0359] Device Examples 45 to 86: Preparation of Green Organic Electroluminescent Devices

[0360] Compound 10, compound 12, compound 16, compound 38, compound 44, compound 69, compound 76, compound 89, compound 91, compound 102, compound 122, compound 131, compound 159, compound 166, compound 183, compound 195, compound 196, compound 216, compound 256, compound 317, compound 336, compound 427, compound 449, compound 463, compound 505, compound 535, compound 564, compound 577, compound 619, compound 625, compound 686, compound 729, compound 749, compound 757, compound 785, compound 804, compound 823, compound 825, compound 826, compound 828, compound 829, and compound 830 of the present invention are used to replace compound 2 in device embodiment 44 as the first host material, and the rest of the preparation process is exactly the same to prepare an organic electroluminescent device.

[0361] Comparative device embodiments 8 to 14:

[0362] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, Comparative Compound 5, Comparative Compound 6 and Comparative Compound 7 were used to replace Compound 44 in Device Example 18 as the first host material, and the rest of the preparation process was exactly the same to prepare an organic electroluminescent device.

[0363] Table 2: Test data of luminescent characteristics of organic electroluminescent devices prepared in device examples 44 to 86 and comparative device examples 8 to 14

[0364]

[0365]

[0366]

[0367] According to the results in Table 2, when the heterocyclic compound described in the present invention is used as the first host material, it has a higher triplet energy level and can effectively improve the luminous efficiency of the device.

[0368] Device Example 87: Preparation of Green Organic Electroluminescent Device

[0369] 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.

[0370] The following layers are deposited layer by layer on the above ITO / Ag / ITO glass substrate: a. HT-3 and P-1 (mass ratio is 97:3) as hole injection layer, and the evaporated film thickness is 15nm. b. HT-3 is used as hole transport layer, and the evaporated film thickness is 85nm. c. EB-2 is used as electron blocking layer, and the evaporated film thickness is 35nm. d. GH-1 is used as the first host material, GH-3 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 35nm. e. ET-2 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. Compound 2 is used as a covering layer, and the evaporated film thickness is 65nm.

[0371] Device Examples 88 to 129: Preparation of Green Organic Electroluminescent Devices

[0372] Compound 10, compound 12, compound 16, compound 38, compound 44, compound 69, compound 76, compound 89, compound 91, compound 102, compound 122, compound 131, compound 159, compound 166, compound 183, compound 195, compound 196, compound 216, compound 256, compound 317, compound 336, compound 427, compound 449, compound 463, compound 505, compound 535, compound 564, compound 577, compound 619, compound 625, compound 686, compound 729, compound 749, compound 757, compound 785, compound 804, compound 823, compound 825, compound 826, compound 828, compound 829, and compound 830 of the present invention are used to replace compound 2 in device embodiment 87 as the covering layer material, and the rest of the preparation process is exactly the same to prepare an organic electroluminescent device.

[0373] Comparative device embodiments 15 to 21:

[0374] Comparative Compound 1, Comparative Compound 2, Comparative Compound 3, Comparative Compound 4, Comparative Compound 5, Comparative Compound 6 and Comparative Compound 7 were used to replace Compound 2 in Device Example 87 as the covering layer material, and the rest of the manufacturing process was exactly the same to prepare an organic electroluminescent device.

[0375] Table 3: Test data of luminescent characteristics of organic electroluminescent devices prepared in device examples 87 to 129 and comparative device examples 15 to 21

[0376]

[0377]

[0378]

[0379] According to the results in Table 3, when the heterocyclic compound described in the present invention is used as a covering layer material, the luminous efficiency and service life of an effective organic electroluminescent device can be improved.

[0380] 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 heterocyclic compound, characterized in that The heterocyclic compound has a structure represented by Formula I: The Ar1 and Ar2 are independently selected from Formula 1; Said Y is selected from O or S; The v 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group; The q is selected from 0, 1, 2, 3, 4 or 5; Said y is independently selected from C(R2) or N, and when y is N, at most 2 y are N atoms; 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-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group; The x is independently selected from CH or N; The n1 is selected from 0, 1 or 2; the n2 is selected from 0, 1 or 2; The Ra and Rb are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted silyl, or the two adjacent Ra and two Rb are connected to each other to form a substituted or unsubstituted C3-C6 ring; The f is selected from 0, 1, 2, 3 or 4; the t is selected from 0, 1, 2, 3 or 4; The R0 is independently selected from 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-C12 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group or any one of the following groups: The Gs are independently selected from CH or N, and at least one G is selected from N; Said Q is independently selected from CH or N; The M is selected from O or S; The K is selected from O, S or N(Rf); 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-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; The Rf is selected from any one of hydrogen, deuterium, cyano, 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group; The c0 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c5 is selected from 0, 1, 2 or 3; When R0 is selected from substituted or unsubstituted C6-C12 aryl, the substituent is selected from 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-C12 aryl, substituted or unsubstituted C2-C12 monocyclic heteroaryl, substituted or unsubstituted C2-C12 polycyclic heteroaryl, substituted or unsubstituted C2-C12 fused ring heteroaryl containing at least one heteroatom of O, S, Si, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic ring fused ring group; The u is selected from 0, 1, 2, 3, 4, 5, 6 or 7; The L1 and L2 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic group and a C6-C30 aromatic ring condensed ring group; The condition is that v, y, x, L1, and L2 contain at least one N atom.

2. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound is selected from any one of the structures represented by the following formula II-1 to formula II-4: The definitions of Ar1, Ar2, L1, L2, R2, Ra, Rb, R0, f, t, n1, n2, and u are the same as those in Formula I; The p0 is selected from 0, 1, 2 or 3; the p1 is selected from 0, 1 or 2.

3. The heterocyclic compound according to claim 1, characterized in that The formula 1 is selected from any one of the following groups: The R1 is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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 heterocyclic compound according to claim 1, characterized in that When n1 and n2 are both 0, the is selected from a single bond, when n1 and n2 are not 0 at the same time, the Any one selected from the following groups: The Ra, Rb, and Rc are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, and iodine, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, and triphenylsilyl; The f is selected from 0, 1, 2, 3 or 4; the f2 is selected from 0, 1 or 2; the f3 is selected from 0, 1, 2 or 3; The t is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1 or 2; the t3 is selected from 0, 1, 2 or 3; The r1 is selected from 0, 1 or 2; the r2 is selected from 0, 1, 2, 3 or 4; the r3 is selected from 0, 1, 2, 3, 4, 5 or 6; the r4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

5. The heterocyclic compound according to claim 1, characterized in that The L1 and L2 are independently selected from a single bond or any one of the following groups: The z is independently selected from CH or N; The s0 is selected from 1, 2 or 3; The T is selected from O, S or N(Rg); The ring W is selected from a substituted or unsubstituted C3-C30 alicyclic ring; 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 group, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaromatic fused ring group; 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 ring; The Rg is 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 b1 is selected from 0, 1, 2, 3 or 4; the b2 is selected from 0, 1, 2 or 3; the b3 is selected from 0, 1 or 2; and the b4 is selected from 0, 1, 2, 3, 4, 5 or 6.

6. The heterocyclic compound according to claim 1, characterized in that The L1 and L2 are independently selected from a single bond or any one of the following groups: The Rn is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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; Said Rw, Rz are independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or any one of the following groups which are substituted or unsubstituted: 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 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; The b1 is selected from 0, 1, 2, 3 or 4; the b2 is selected from 0, 1, 2 or 3; the b3 is selected from 0, 1 or 2; the b4 is selected from 0, 1, 2, 3, 4, 5 or 6; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

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

8. An organic electroluminescent device, comprising an anode, a cathode and an organic functional layer located between the anode and the cathode or located on a side of the cathode away from the anode, characterized in that: The organic functional layer comprises any one or more of the heterocyclic compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic functional layer is located between the anode and the cathode, wherein: The organic functional layer comprises an electron transport region, and the electron transport region comprises any one or more of the heterocyclic compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic functional layer is located on a side of the cathode away from the anode, wherein: The organic functional layer comprises a covering layer, and the covering layer comprises any one or more of the heterocyclic compounds according to any one of claims 1 to 7.

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