Heterocyclic compound and organic electroluminescent device thereof

Abstract

The invention provides a heterocyclic compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The heterocyclic compound disclosed by the invention has relatively high electron mobility, energy level matched with an adjacent functional layer, good film-forming property and thermal stability, and can be used as an electron transport material in an organic electroluminescent device, so that the electron transport efficiency in the device can be effectively improved, electrons and holes in the device can be balanced, and the efficiency of the organic electroluminescent device can be improved. The organic light-emitting device is beneficial to electron and hole recombination in the light-emitting layer, the light-emitting efficiency of the organic light-emitting device is improved, the driving voltage of the organic light-emitting device is reduced, and the service life of the organic light-emitting device is prolonged. Meanwhile, the heterocyclic compound provided by the invention is used as a hole blocking material in the organic electroluminescent device, can effectively block diffusion of holes to one side of an electron transport region, and further improves the performance of the organic electroluminescent device. The heterocyclic compound can be applied to the fields of information display, illumination, organic solar cells and the like.

Description

Technical Field

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

[0002] An organic electroluminescent device (OLED), also known as an organic electroluminescent diode, has a light-emitting process in which, under a certain driving voltage, electrons are injected from the cathode and holes are injected from the anode. After reaching the light-emitting layer through the transfer of each functional layer, they recombine into excitons. The excitons transfer energy to the light-emitting material to cause it to jump from the ground state to the excited state. Since the excited molecules are unstable, different colors of light-emitting phenomena are generated through radiative transitions. Due to the many characteristics of organic electroluminescent devices, such as being all-solid-state, thin and light in body, low in energy consumption, high in efficiency, fast in response speed, and capable of flexible display, they have been applied in many fields.

[0003] Organic electroluminescence can be mainly divided into five stages: injection and transport of electrons, injection and transport of holes, formation of excitons, migration of excitons, and electroluminescence process. Among them, the selection of materials for organic functional layers is crucial. Organic functional layers can be mainly divided into a hole transport region, a light-emitting layer, an electron transport region, etc. Materials for the hole transport region mainly include hole injection materials, hole transport materials, and electron blocking materials, etc.; materials for the electron transport region mainly include electron injection materials, electron transport materials, and hole blocking materials, etc. Currently, the electron transport rate of most electron transport materials is much lower than the hole transport rate of hole transport materials, resulting in an imbalance in the transport of electrons and holes in the device, seriously affecting the performance of organic electroluminescent devices; on the other hand, the energy levels of electron transport materials do not match those of adjacent functional layers, leading to problems such as an increase in the electron injection potential energy and the diffusion of holes into the electron transport region, which will also reduce the performance of organic electroluminescent devices.

[0004] Therefore, it is necessary to develop electron transport materials and hole blocking materials with high electron mobility and appropriate energy levels to further improve the performance of organic electroluminescent devices. Summary of the Invention

[0005] In view of the problems existing in the prior art, the present invention provides a heterocyclic compound and an organic electroluminescent device thereof.

[0006] The present invention provides a heterocyclic compound represented by the following formula 1,

[0007]

[0008] wherein, the R a is selected from one or more R wOne of the following substituted groups: aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, a fused ring group of an alicyclic ring having 3 to 20 carbon atoms and an aromatic ring having 6 to 30 carbon atoms, said R w One of the same or different groups selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms;

[0009] Said R b One of the groups selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted fused ring group of an alicyclic ring having 3 to 20 carbon atoms and an aromatic ring having 6 to 30 carbon atoms, and the "substituted or unsubstituted" substituents are selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted fused ring group of an alicyclic ring having 3 to 20 carbon atoms and an aromatic ring having 6 to 30 carbon atoms;

[0010] Said z are the same or different and are selected from CR c or N, and the bonding z is selected from C atoms with respect to L 1 ;

[0011] Said R c are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted fused ring group of an alicyclic ring having 3 to 20 carbon atoms and an aromatic ring having 6 to 30 carbon atoms, or two adjacent Rs c bond to form a substituted or unsubstituted ring;

[0012] Said X is selected from O or S;

[0013] Said R 1 are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted silyl, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms, substituted or unsubstituted fused ring group of an alicyclic ring having 3 to 20 carbon atoms and an aromatic ring having 6 to 30 carbon atoms, or two adjacent Rs 1 bond to form a substituted or unsubstituted ring;

[0014] Said n 1 is selected from 0, 1, 2, 3 or 4;

[0015] Said L 1Selected from a single bond, a substituted or unsubstituted C6-C27 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring fused sub-ring group, or a combination thereof; the substituents in the "substituted or unsubstituted arylene group, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused sub-ring group" are selected from a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring group, or a combination thereof; the substituents in the "substituted or unsubstituted C2-C30 heteroarylene group" are selected from a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group.

[0016] In addition, the present invention also provides an organic electroluminescent device, which contains the heterocyclic compound of the present invention.

[0017] Beneficial effects: In the heterocyclic compound of Formula 1 of the present invention, the 9-position of the fluorene group has a single-sided alkyl / cycloalkyl substitution, which has a high electron mobility, energy levels matching with adjacent functional layers, good film-forming property and thermal stability. When used as an electron transport material in an organic electroluminescent device, it can effectively improve the electron transport efficiency in the device, balance electrons and holes in the device, facilitate the recombination of electrons and holes in the light-emitting layer, improve the light-emitting efficiency of the organic electroluminescent device, reduce the driving voltage of the organic electroluminescent device, and extend the service life of the organic electroluminescent device. At the same time, the heterocyclic compound of Formula 1 of the present invention, when used as a hole blocking material in an organic electroluminescent device, can effectively block the diffusion of holes to the electron transport region side, and further improve the performance of the organic electroluminescent device. Detailed implementation manners

[0018] The following further clarifies the present invention in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the scope of the present invention. After reading the present invention, various equivalent modifications made by those skilled in the art to the present invention fall within the scope claimed in this application.

[0019] In the compounds of the present invention, any atom not specified as a specific isotope includes any stable isotope of that atom, and includes atoms in both their natural and non-natural isotope abundances.

[0020] The halogen described in the present invention includes fluorine, chlorine, bromine and iodine.

[0021] In the present invention, the "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atoms of the "ZZ group" are not replaced by substituents. For example, in the "substituted or unsubstituted aryl group having 6 to 30 carbon atoms", the "unsubstituted aryl group" means that the hydrogen atoms of the "aryl group" are not replaced by substituents. And so on.

[0022] In the present invention, "CXX to CYY" in the "substituted or unsubstituted ZZ group having CXX to CYY carbon atoms" represents the number of carbon atoms in the "ZZ group" without substitution. When the "ZZ group" has substituents, it does not include the carbon atoms of the substituents. For example, in the "substituted or unsubstituted aryl group having 6 to 30 carbon atoms", "6 to 30" represents the number of carbon atoms in the "aryl group" without substitution. When the "aryl group" has substituents, it does not include the carbon atoms of the substituents. In the "substituted or unsubstituted fused ring group of an alicyclic ring having 3 to 30 carbon atoms and an aromatic ring having 6 to 30 carbon atoms", "3 to 30" represents the number of carbon atoms in the "alicyclic ring" without substitution. When the "alicyclic ring" has substituents, it does not include the carbon atoms of the substituents; "6 to 30" represents the number of carbon atoms in the "aromatic ring" without substitution. When the "aromatic ring" has substituents, it does not include the carbon atoms of the substituents. And so on.

[0023] In the present invention, when the position of the substituent on the ring is not fixed, it means that it can be connected to any of the corresponding optional sites of the ring.

[0024] For example, can be represented as can be represented as can be represented as And so on.

[0025] In this specification, when the bond where the substituent or the connection site is located penetrates 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 represented as can be represented as And so on.

[0026] In the present invention, "adjacent two groups bonding to form a ring" means that adjacent groups combine with each other and optionally aromatize to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be monocyclic or polycyclic groups. Examples are as follows:

[0027]

[0028] In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. Examples are as follows:

[0029]

[0030] In the present invention, the ring formed by connection can be a three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, fused ring, spiro ring, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited thereto.

[0031] In the present invention, "substituted" in "substituted or unsubstituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents can be the same or different. The position of the hydrogen replaced by the substituent can be any position. The substituents represented by "substituted" in the above "substituted or unsubstituted" include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C2-C15 heterocyclic group, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C20 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C2-C20 heteroaromatic ring, etc. Preferred are the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphenyl, isocamphenyl, fenchyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylenyl, anthryl, pyrenyl, Groups such as a base, fluoranthenyl, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl, fluorenyl, spirobifluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. In addition, each of the above substituents may be substituted or unsubstituted. Two adjacent substituents may be bonded to form a ring.

[0032] The alkyl group described in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group may be a straight-chain alkyl group or a branched-chain alkyl group. When the number of carbon atoms of the chain alkyl group described in the present invention is three or more, its isomers are included. For example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of the alkyl group include, but are not limited to, the groups described below, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The number of carbon atoms of the alkyl group is C1-C30, preferably C1-C25, preferably C1-C20, preferably C1-C15, and more preferably C1-C10.

[0033] The silyl group described in the present invention refers to a -Si(R k ) 3 group, where each R k is the same or different and is selected from the groups described below: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C6-C60 aromatic ring, substituted or unsubstituted C3-C30 fused ring group of an alicyclic ring and a C2-C60 heteroaromatic ring. Preferably, each R k is the same or different and is selected from the groups described below: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms of the alkyl group is preferably C1-C20, preferably C1-C15, more preferably C1-C10, and most preferably C1-C8. The number of carbon atoms of the cycloalkyl group is preferably C3-C20, preferably C3-C15, more preferably C3-C10, and most preferably C3-C7. Preferably, each R kSame or different and selected from the following groups: hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted pentyl group, substituted or unsubstituted hexyl group, substituted or unsubstituted heptyl group, substituted or unsubstituted octyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted cycloheptyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group. Preferred substituted silyls specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0034] The cycloalkyl group described in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl groups, polycyclic cycloalkyl groups, and bridged cycloalkyl groups. Examples of the cycloalkyl group include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenyl, fenchyl, isocamphenyl, etc., but are not limited thereto. The number of carbon atoms in the cycloalkyl group is C3-C30, preferably C3-C25, preferably C3-C20, preferably C3-C15, and more preferably C3-C10.

[0035] The aryl group described in the present invention refers to the general term for a monovalent group remaining after removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused-ring aryl groups, or combinations thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, triphenylene, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthracenefluorenyl, pyrenyl, -yl, fluoranthenyl, etc., but are not limited thereto. The number of carbon atoms in the aryl group is C6-C30, preferably C6-C25, and more preferably C6-C20.

[0036] The heteroaryl group in the present invention refers to a monovalent group in which at least one carbon atom in the aryl group is replaced by a heteroatom. The heteroatoms are selected from O, S, N, Si, B, P, etc., but are not limited thereto. Examples of the heteroaryl group include, but are not limited to, the groups described below: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothienyl, naphthothienyl, phenanthrothienyl, dibenzothienyl, benzodibenzothienyl, indolyl, naphthylindolyl, carbazolyl, benzocarbazolyl, spirofluoreneoxanthenyl, spirofluoreneanthionyl, spirofluoreneazaxanthenyl, spirofluorenesilanthionyl, benzodioxolyl, benzodithioetheryl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothienyl, dihydroisobenzothienyl, phenoxazinyl, phenothiazinyl, dihydroacridinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc., but are not limited thereto. The number of carbon atoms in the heteroaryl group can be C2-C30, preferably C2-C25, more preferably C3-C20.

[0037] The fused ring group of the alicyclic ring and the aromatic ring in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom after the alicyclic ring and the aromatic ring are fused together. Examples of the fused ring group of the alicyclic ring and the aromatic ring include, but are not limited to, the groups described below: benzocyclopropyl, benzocyclobutyl, benzocyclobutenyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3-C30, preferably C3-C20, preferably C3-C15, more preferably C3-C10, and even more preferably C3-C8. The number of carbon atoms in the aromatic ring is C6-C30, preferably C6-C25, preferably C6-C18, more preferably C6-C12, and even more preferably C6-C10.

[0038] The arylene group in the present invention refers to the general name of the divalent group remaining after removing two hydrogen atoms from the aromatic nucleus carbon of the aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused ring arylene or a combination thereof. Examples of the arylene group include, but are not limited to, the groups described below: phenylene, biphenylene, terphenylenyl, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, spirobifluorenylene, etc., but are not limited thereto. The number of carbon atoms in the arylene group is C6-C30, preferably C6-C25, preferably C6-C20, and more preferably C6-C18.

[0039] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heteroarylene group includes monocyclic heteroarylene, polycyclic heteroarylene, fused-ring heteroarylene or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the groups described below, such as pyridylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, quinazolinylene, naphthyridinylene, etc., but are not limited thereto. The number of carbon atoms in the heteroarylene group is C2-C30, preferably C2-C25, more preferably C2-C20.

[0040] The sub-fused ring group of the alicyclic and aromatic rings described in the present invention refers to the general term of the divalent group remaining after removing two hydrogen atoms after the alicyclic ring and the aromatic ring are fused together. The sub-fused ring of the alicyclic and aromatic rings includes indanylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropylidene, benzocyclobutylidene, benzocycloheptylidene, benzocyclobutenylene, naphthocyclopentylidene, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is 3-30, preferably 3-20, more preferably 3-10. The number of carbon atoms in the aromatic ring is 6-30, preferably 6-25, preferably 6-18, more preferably 6-10.

[0041] The present invention provides a heterocyclic compound represented by the following formula 1,

[0042]

[0043] wherein, the R a is selected from one of the following groups substituted by one or more R w : aryl group of C6-C30, heteroaryl group of C2-C30, fused ring group of alicyclic ring of C3-C20 and aromatic ring of C6-C30, and the R w is the same or different and is selected from one of substituted or unsubstituted alkyl group of C1-C20 and substituted or unsubstituted cycloalkyl group of C3-C20;

[0044] The R b is selected from one of substituted or unsubstituted aryl group of C6-C30, substituted or unsubstituted heteroaryl group of C2-C30, substituted or unsubstituted fused ring group of alicyclic ring of C3-C20 and aromatic ring of C6-C30, and the "substituted or unsubstituted" substituent is selected from deuterium, cyano group, halogen, nitro group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group of C6-C30, substituted or unsubstituted heteroaryl group of C2-C30, substituted or unsubstituted fused ring group of alicyclic ring of C3-C20 and aromatic ring of C6-C30;

[0045] The z is the same or different and is selected from CR c or N, and is combined with L1 The bonding z is selected from a C atom;

[0046] Said R c which are the same or different and are each independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring groups, or two adjacent Rs c bond to form a substituted or unsubstituted ring;

[0047] Said X is selected from O or S;

[0048] Said R 1 which are the same or different and are each independently selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring groups, or two adjacent Rs 1 bond to form a substituted or unsubstituted ring;

[0049] Said n 1 is selected from 0, 1, 2, 3 or 4;

[0050] Said L 1 is selected from a single bond, substituted or unsubstituted C6-C27 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring arylene, or a combination thereof; the substituents in the "substituted or unsubstituted arylene, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring arylene" are selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring groups, or a combination thereof; the substituents in the "substituted or unsubstituted C2-C30 heteroarylene" are selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl.

[0051] Preferably, the heterocyclic compound is selected from one of the following formula 1-1 or formula 1-2,

[0052]

[0053] Preferably, the is selected from one of the groups shown below,

[0054]

[0055]

[0056] The R c are the same or different and are each independently selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group selected from the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or two adjacent Rs c bond to form a substituted or unsubstituted ring;

[0057] The R d are the same or different and are each independently selected from hydrogen, deuterium, cyano, halogen, nitro, or a substituted or unsubstituted group selected from the following: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

[0058] The R w are the same or different and are each independently selected from a substituted or unsubstituted group selected from the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, norbornyl;

[0059] The m1 selected from 0, 1, 2 or 3; said m 2 selected from 0, 1, 2, 3 or 4; said m 3 selected from 0, 1, 2, 3, 4 or 5; said m 4 selected from 0, 1 or 2; said m 5 selected from 0, 1, 2, 3, 4, 5, 6 or 7; said m 6 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said m 7 selected from 0, 1, 2, 3, 4, 5 or 6; said m 8 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said m 9 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12;

[0060] said p 1 selected from 1, 2, 3, 4 or 5; said p 2 selected from 0, 1, 2, 3 or 4; said p 3 selected from 1, 2, 3, 4, 5, 6 or 7; said p 4 selected from 1, 2 or 3; said p 5 selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said p 6 selected from 1, 2, 3 or 4; said p 7 selected from 0, 1, 2, 3, 4 or 5; said p 8 selected from 1, 2, 3, 4, 5 or 6; said p 9 selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said p 10 selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0061] Preferably, said R cThe same or different, selected from hydrogen, deuterium, cyano, halogen, nitro, and one or more of the following groups which are either deuterium-substituted, C1-C8 alkyl-substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or two adjacent Rs c are bonded to form a substituted or unsubstituted benzene ring.

[0062] Preferably, the Rs d are the same or different and are each independently selected from hydrogen, deuterium, cyano, halogen, nitro, and one or more of the following groups which are either deuterium-substituted or unsubstituted: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.

[0063] Preferably, the Rs w are the same or different and are each independently selected from one or more of the following groups which are either deuterium-substituted, C1-C8 alkyl-substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, norbornyl.

[0064] More preferably, the Rs w are the same or different and are each independently selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl.

[0065] Most preferably, the Rs w are the same or different and are each independently selected from methyl, ethyl, isopropyl, tert-butyl.

[0066] Preferably, the is selected from one of the groups shown below,

[0067]

[0068] X is selected from O or S;

[0069] The R 1 are the same or different and are each selected from hydrogen, cyano, halogen, nitro, and one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or two adjacent Rs 1 bond to form a substituted or unsubstituted benzene ring;

[0070] The n 1 is selected from 0, 1, 2, 3, or 4; the n 2 is selected from 0, 1, 2, 3, 4, 5, or 6; the n 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n 4 is selected from 0, 1, or 2; the n 5 is selected from 0, 1, 2, or 3; the n 6 is selected from 0, 1, 2, 3, 4, or 5; the n 7 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n 8 is selected from 0 or 1.

[0071] Preferably, the is selected from one of the groups shown below,

[0072]

[0073] The R 1Same or different and selected from hydrogen, cyano, halogen, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

[0074] Said n 1 Selected from 0, 1, 2, 3 or 4; said n 5 Selected from 0, 1, 2 or 3.

[0075] Preferably, said L 1 Selected from a single bond or one or a combination of the following groups,

[0076]

[0077] Said R 20 Same or different and selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or two adjacent Rs 20 Bond to form a substituted or unsubstituted ring;

[0078] Said R 5 R 6 Same or different and selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 cycloaliphatic and C6-C30 aromatic fused ring group, or adjacent Rs 5 R 6 Bond to form a substituted or unsubstituted ring;

[0079] Said y is same or different and selected from CR 21 Or N, and at least one y is selected from N;

[0080] The R 21 are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent Rs 21 bond to form a substituted or unsubstituted ring;

[0081] The vs are the same or different and are selected from CR 22 or N;

[0082] The R 22 are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent Rs 22 bond to form a substituted or unsubstituted ring;

[0083] The T 1 is selected from O, S or NR 3 , the T 2 is selected from CR 4 or N; the T 3 is selected from O, S or NR 7 ;

[0084] The R 3 , R 7 are the same or different and are selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group;

[0085] The R 4 is selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring group;

[0086] The t 1 is selected from 0, 1, 2, 3 or 4; the t 2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t 4 is selected from 0, 1, 2 or 3.

[0087] Preferably, the L1 One selected from a single bond or the groups shown below,

[0088]

[0089]

[0090] wherein said R 20 is the same as or different from, and is one selected from hydrogen, cyano, halogen, nitro, a substituted or unsubstituted group shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuryl, benzothienyl, dibenzofuryl, dibenzothienyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzoxazolyl, benzothiazolyl, or two adjacent Rs 20 bond to form a substituted or unsubstituted ring;

[0091] wherein said R 21 and R 22 are the same as or different from, and are one selected from hydrogen, cyano, halogen, nitro, a substituted or unsubstituted group shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, or two adjacent Rs 21 or two Rs 22 bond to form a substituted or unsubstituted ring;

[0092] wherein said R 4the same or different and selected from one of the following groups: hydrogen, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

[0093] said R 5 and R 6 the same or different and selected from one of the following groups: hydrogen, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

[0094] said R 7 the same or different and selected from one of the following groups: substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl;

[0095] said t1 is selected from 0, 1, 2, 3 or 4; said t 2 is selected from 0, 1, 2, 3, 4, 5 or 6; said t 3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said t 4 is selected from 0, 1, 2 or 3; said t 5 is selected from 0, 1 or 2; said t 6 is selected from 0 or 1; said t 7 is selected from 0, 1, 2, 3, 4 or 5; said t 8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said t 9 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0096] Preferably, the R 20 , R 4 , R 5 , R 6 , R 7 The "substituted or unsubstituted" substituents are selected from cyano, halogen, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylmethyl One of silyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl and quinoxalinyl.

[0097] Preferably, the R 21 , R 22 the same or different selected from hydrogen, cyano, halogen, nitro, one of the following groups which are substituted or unsubstituted by one or more deuteriums: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, or two adjacent R 21 , two R 22 Bonding to form a substituted or unsubstituted benzene ring.

[0098] Preferably, the Selected from Said Selected from The said Selected from The said Selected from The said Selected from The said Selected from The said Selected from The said Selected from The said Selected from The said Selected from

[0099] Preferably, the heterocyclic compound is selected from any one of the structures shown below,

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The above lists some specific chemical structures of the heterocyclic compounds shown in Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures, and all those based on the structure shown in Formula 1 with substituents being the groups defined as above should be included.

[0121] In addition, the present invention also provides an organic electroluminescent device, and the organic electroluminescent device contains the heterocyclic compound of the present invention.

[0122] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer. The organic layer is located between the anode and the cathode or outside one or more of the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention.

[0123] Preferably, the organic layer is located between the anode and the cathode. The organic layer includes an electron transport region, and the electron transport region contains the heterocyclic compound of the present invention.

[0124] Preferably, the organic layer is located between the anode and the cathode. The organic layer includes an electron transport region, and the electron transport region includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer. At least one of the electron injection layer, the electron transport layer, and the hole blocking layer contains the heterocyclic compound of the present invention.

[0125] Preferably, the organic layer is located between the anode and the cathode. The organic layer includes an electron transport region, and the electron transport region includes an electron transport layer, and the electron transport layer contains the heterocyclic compound of the present invention.

[0126] Preferably, the organic layer is located between the anode and the cathode. The organic layer includes an electron transport region, and the electron transport region includes a hole blocking layer, and the hole blocking layer contains the heterocyclic compound of the present invention.

[0127] Preferably, the organic layer is located between the anode and the cathode. The organic layer includes an electron transport region, and the electron transport region includes an electron transport layer and a hole blocking layer, and the electron transport layer and the hole blocking layer contain the heterocyclic compound of the present invention.

[0128] Preferably, the organic electroluminescent device of the present invention is divided into a single-layer organic electroluminescent device and a stacked organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the stacked organic electroluminescent device is an organic electroluminescent device formed by connecting two or more independent light-emitting units in series through a charge generation layer.

[0129] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device. The single-layer organic electroluminescent device includes an anode, a cathode, and an organic layer. The organic layer is located between the anode and the cathode or outside one or more of the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention.

[0130] Preferably, the organic electroluminescent device of the present invention is a stacked organic electroluminescent device. The stacked organic electroluminescent device includes an anode, a cathode, and an organic layer. The organic layer is located between the anode and the cathode, and the organic layer contains the heterocyclic compound of the present invention.

[0131] The organic electroluminescent device of the present invention may further include a substrate. The substrate of the present invention preferably uses a material that does not change when forming electrodes and other functional layers. Specific examples of the substrate material that can be used in the present invention may include glass, quartz, plastic, polymer film, silicon, etc., but are not limited thereto.

[0132] The present invention does not particularly limit the materials of the thin films of each layer in the organic electroluminescent device, and substances known in the art can be used. The following separately introduces the organic functional layers of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device:

[0133] The anode material of the present invention preferably has a material with a large work function. The anode material may include metals, metal alloys, metal oxides, conductive polymers, etc., but is not limited thereto. Specific examples of the anode material may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 )), zinc oxide (ZnO), gold (Au), copper (Cu), magnesium-silver (Mg-Ag), poly(3-methylthiophene), polyaniline, polypyrrole, etc., but are not limited thereto.

[0134] The hole injection layer described in the present invention preferably uses a material with good hole injection ability. The hole injection layer material may include, but is not limited to, arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, conductive polymers, etc. Specific examples of the hole injection material may include copper phthalocyanine (CuPc), 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), etc., but are not limited to these.

[0135] The hole transport layer described in the present invention preferably uses a material with a high hole mobility. The hole transport material includes, but is not limited to, carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, phthalocyanine compounds, etc. Specific examples of the hole transport material may include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 1,3,5-tris(9-carbazolyl)benzene (TCB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), etc., but are not limited to these.

[0136] The electron blocking layer of the present invention is a material with electron blocking ability. The electron blocking material may include, but is not limited to, arylamine derivatives, carbazole derivatives, spirofluorene derivatives, etc. Specific examples of the electron blocking material may include N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-yl)-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited to these.

[0137] The light-emitting layer described in the present invention comprises a host material and a guest material. The host material includes, but is not limited to, heterocyclic compounds, metal complexes, fused polycyclic aromatic hydrocarbon compounds, aromatic amine compounds, etc. Specific examples may include 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(N-carbazolyl)benzene (MCP), 9,10-di(2-naphthyl)anthracene (ADN), etc., but are not limited to these. The guest material includes, but is not limited to, aromatic amine derivatives, boron complexes, pyrene compounds, metal complexes, etc. Specific examples may include tris(2-phenylpyridine)iridium (Ir(ppy) 3 ), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq) 2 (acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq) 3) such as 2,5,8,11-tetra-tert-butylperylene (TBPe), etc., but not limited thereto.

[0138] The hole blocking layer described in the present invention preferably uses a material with hole blocking ability. Specific examples of the hole blocking layer material may include metal complexes, heteroaromatic compounds, etc., such as bis(2-methyl-8-hydroxyquinoline)(4-phenylphenolato)aluminum(III) (BAlq), 1,3,5-tris(1-phenyl-1H-benzoimidazol-2-yl)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc., but not limited thereto. The heteroaromatic compound described in the present invention is preferred.

[0139] The electron transport layer described in the present invention preferably uses a material with high electron mobility. The electron transport layer material may include oxazole derivatives, thiazole derivatives, quinoline derivatives, triazine derivatives, triazole derivatives, phenanthroline derivatives, metal complexes, etc. Specific examples of the electron transport layer material may include lithium 8-hydroxyquinolate (LiQ), tris(8-hydroxyquinolinato)aluminum(Alq 3 ) bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 2,9-(dimethyl)-4,7-diphenyl-1,10-phenanthroline (BCP), etc., but not limited thereto. The heteroaromatic compound described in the present invention is preferred.

[0140] The electron injection layer described in the present invention preferably uses a material with good electron injection ability. The electron injection layer material includes alkali metals, alkali metal compounds, alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes, etc., but not limited thereto. Specific examples of the electron injection material may include lithium (Li), lithium fluoride (LiF), lithium 8-hydroxyquinolate (LiQ), cesium oxide (Cs 2 O), etc., but not limited thereto.

[0141] The cathode material described in the present invention preferably uses a material with a small work function. The cathode material may include metals, metal oxides, conductive polymers, etc., but not limited thereto. Specific examples of the cathode material may include magnesium (Mg), calcium (Ca), sodium (Na), lithium (Li), aluminum (Al), silver (Ag), tin (Sn), indium (In), titanium (Ti), LiF / Al multilayer structure materials, etc., but not limited thereto.

[0142] The capping layer material described in the present invention preferably uses a material with a light coupling effect. The capping layer material includes metal oxides, metal nitrides, metal fluorides, arylamine derivatives, carbazole derivatives, etc., but not limited thereto. Specific examples of the capping layer material may include tris(8-hydroxyquinolinato)aluminum(Alq3 )), zirconium oxide (ZrO), zinc oxide (ZnO), silicon dioxide (SiO 2 ), cesium fluoride (CsF), lithium fluoride (LiF), etc., but not limited thereto.

[0143] There is no particular limitation on the preparation method of each thin film layer in the organic electroluminescent device of the present invention. Vacuum evaporation method, sputtering method, spin coating method, spraying method, screen printing method, laser transfer printing method, etc. can be used, but not limited thereto.

[0144] The organic electroluminescent device of the present invention is mainly applied to the fields of information display technology, lighting field, and organic solar cells, etc., such as mobile phones, tablet computers, flat panel TVs, various wearable devices, etc.

[0145] The following examples illustrate the present invention in more detail. However, the following examples are only used to illustrate this specification, and the scope of this specification is not limited to these examples.

[0146] Synthesis Example

[0147] Raw materials and reagents: There is no particular limitation on the raw materials or reagents used in the following synthesis examples of the present invention. They can be commercially available products or prepared by methods well-known to those skilled in the art. The raw materials and reagents used in the present invention are all of reagent grade.

[0148] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube type organic elemental analyzer (Elementar, Germany).

[0149] There is no particular limitation on the preparation method of the heterocyclic compound shown in Formula 1 of the present invention. Conventional methods well-known to those skilled in the art can be used. For example, carbon-carbon coupling reaction, etc. The heterocyclic compound shown in Formula 1 of the present invention can be prepared by the following synthesis route.

[0150] Synthesis Route 1:

[0151]

[0152] Synthesis Route 2: When L 1 is selected from a single bond, the synthesis route of the heterocyclic compound shown in Formula 1 is as follows:

[0153]

[0154] The Xn is a halogen, for example, Xn is the same or different and is selected from one of Cl, Br, and I; the R a , R b , R 1 , L 1, X, z, n 1 Same as the above definition.

[0155] Synthesis Example 1: Preparation of Intermediate a-38

[0156]

[0157] Dissolve e-38 (64.62 g, 180.00 mmol) in 320.00 ml of anhydrous tetrahydrofuran. Under nitrogen, maintain the temperature of the solution at -78 °C. Slowly add a hexane solution of n-butyllithium (72.00 ml, 2.5 M) dropwise to the solution. After the addition is complete, stir for 2.5 hours. Then dissolve d-38 (37.85 g, 180.00 mmol) in 220.00 ml of tetrahydrofuran, slowly add it dropwise, maintain the reaction solution at -78 °C, stir for 2 hours, and then stir overnight at room temperature. Remove the solvent under reduced pressure. Dissolve the residue in glacial acetic acid (270.00 ml), add concentrated hydrochloric acid solution (27.00 ml, 31%), react the mixture under reflux for 6 hours, and stir overnight at room temperature. After the reaction is completed, add water, extract with dichloromethane, combine the organic phases, wash with water, dry over anhydrous magnesium sulfate, remove the solvent under reduced pressure, and recrystallize with isopropanol to obtain Intermediate a-38 (53.60 g, yield 70%), HPLC purity ≥ 99.80%. Mass spectrometry m / z: 424.0814 (theoretical value: 424.0827).

[0158] Synthesis Example 2: Preparation of Intermediate a-42

[0159]

[0160] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-42 to obtain Intermediate a-42 (58.79 g), HPLC purity ≥ 99.83%. Mass spectrometry m / z: 486.0961 (theoretical value: 486.0983).

[0161] Synthesis Example 3: Preparation of Intermediate a-72

[0162]

[0163] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-72 to obtain Intermediate a-72 (50.47 g), HPLC purity ≥ 99.76%. Mass spectrometry m / z: 411.0631 (theoretical value: 411.0623).

[0164] Synthesis Example 4: Preparation of Intermediate a-335

[0165]

[0166] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-335 to obtain intermediate a-335 (56.13 g), with HPLC purity ≥ 99.75%. Mass spectrometry m / z: 464.1154 (theoretical value: 464.1140).

[0167] Synthesis Example 5: Preparation of Intermediate a-412

[0168]

[0169] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-412 to obtain intermediate a-412 (55.13 g), with HPLC purity ≥ 99.86%. Mass spectrometry m / z: 424.0817 (theoretical value: 424.0827).

[0170] Synthesis Example 6: Preparation of Intermediate a-522

[0171]

[0172] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-522 to obtain intermediate a-522 (56.15 g), with HPLC purity ≥ 99.80%. Mass spectrometry m / z: 438.0994 (theoretical value: 438.0983).

[0173] Synthesis Example 7: Preparation of Intermediate a-596

[0174]

[0175] According to the same preparation method as in Synthesis Example 1, replace d-38 with an equimolar amount of d-596 to obtain intermediate a-596 (51.71 g), with HPLC purity ≥ 99.81%. Mass spectrometry m / z: 415.0964 (theoretical value: 415.0984).

[0176] Synthesis Example 8: Preparation of Compound 17

[0177]

[0178] Preparation of Intermediate A-17: Under nitrogen protection, add a-17 (45.25 g, 110.00 mmol), bis(pinacolato)diboron (27.93 g, 110.00 mmol), K 2 CO 3 (30.41 g, 220.00 mmol), Pd(PPh 3 ) 4(1.27 g, 1.10 mmol), 750 mL of dimethylformamide, and stirred under reflux for 5.5 hours. After the reaction, the reaction mixture was cooled to room temperature, water was added thereto, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then recrystallized with toluene / ethanol = 10:1 to obtain intermediate A-17 (40.84 g, yield 81%), HPLC purity ≥ 99.76%. Mass spectrometry m / z: 458.2429 (theoretical value: 458.2417).

[0179] Preparation of intermediate B-17: Under nitrogen protection, A-17 (36.67 g, 80.00 mmol), b-17 (21.40 g, 80.00 mmol), K 2 CO 3 (16.58 g, 120.00 mmol), Pd(PPh 3 ) 4 (0.92 g, 0.80 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask and stirred under reflux for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered by suction, rinsed with ethanol, and then the obtained solid was recrystallized with toluene to obtain intermediate B-17 (31.98 g, yield 77%), HPLC purity ≥ 99.72%. Mass spectrometry m / z: 518.1820 (theoretical value: 518.1801).

[0180] Preparation of intermediate C-17: Under nitrogen protection, B-17 (25.95 g, 50.00 mmol), bis(pinacolato)diboron (12.70 g, 50.00 mmol), KOAc (9.81 g, 100.00 mmol), Pd(dppf)Cl 2 (0.37 g, 0.50 mmol), and 500 mL of 1,4-dioxane were added to a reaction flask and stirred under reflux for 4.5 hours. After the reaction, the reaction mixture was cooled to room temperature, water was added thereto, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then recrystallized with toluene to obtain intermediate C-17 (22.90 g, yield 75%), HPLC purity ≥ 99.80%. Mass spectrometry m / z: 610.3052 (theoretical value: 610.3043).

[0181] Preparation of compound 17: Under nitrogen protection, C-17 (18.32 g, 30.00 mmol), c-17 (5.94 g, 30.00 mmol), K 2 CO 3 (6.22 g, 45.00 mmol), Pd2 (dba) 3 (0.27 g, 0.30 mmol), P(t-Bu) 3 (0.12 g, 0.60 mmol), 250 mL of tetrahydrofuran, stirred and reacted under reflux for 6.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered by suction to obtain a filter cake, rinsed with a small amount of toluene, and then the obtained filter cake was recrystallized with toluene to obtain Compound 17 (13.18 g, yield 73%), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 601.2421 (theoretical value: 601.2406). Theoretical elemental content (%) C 45 H 31 NO: C, 89.82; H, 5.19; N, 2.33. Measured elemental content (%): C, 89.79; H, 5.23; N, 2.31.

[0182] Synthesis Example 9: Preparation of Compound 19

[0183]

[0184] According to the same preparation method as in Synthesis Example 8, replacing a-17 with an equimolar amount of a-19, Compound 19 (13.91 g) was obtained, HPLC purity ≥ 99.90%. Mass spectrometry m / z: 643.2856 (theoretical value: 643.2875). Theoretical elemental content (%) C 48 H 37 NO: C, 89.55; H, 5.79; N, 2.18. Measured elemental content (%): C, 89.50; H, 5.81; N, 2.20.

[0185] Synthesis Example 10: Preparation of Compound 24

[0186]

[0187] According to the same preparation method as in Synthesis Example 8, replacing b-17 with an equimolar amount of b-24, Compound 24 (13.00 g) was obtained, HPLC purity ≥ 99.96%. Mass spectrometry m / z: 601.2416 (theoretical value: 601.2406). Theoretical elemental content (%) C 45 H 31 NO: C, 89.82; H, 5.19; N, 2.33. Measured elemental content (%): C, 89.78; H, 5.22; N, 2.35.

[0188] Synthesis Example 11: Preparation of Compound 38

[0189]

[0190] According to the same preparation method as in Synthesis Example 8, replace a-17 with an equimolar amount of a-38 to obtain Compound 38 (13.12 g), HPLC purity ≥ 99.91%. Mass spectrometry m / z: 615.2550 (theoretical value: 615.2562). Theoretical elemental content (%) C 46 H 33 NO: C, 89.73; H, 5.40; N, 2.27. Measured elemental content (%): C, 89.75; H, 5.35; N, 2.30.

[0191] Synthesis Example 12: Preparation of Compound 42

[0192]

[0193] According to the same preparation method as in Synthesis Example 8, replace a-17 with an equimolar amount of a-42 to obtain Compound 42 (13.83 g), HPLC purity ≥ 99.94%. Mass spectrometry m / z: 677.2711 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Measured elemental content (%): C, 90.40; H, 5.15; N, 2.11.

[0194] Synthesis Example 13: Preparation of Compound 60

[0195]

[0196] According to the same preparation method as in Synthesis Example 8, replace a-17 with an equimolar amount of a-60 to obtain Compound 60 (14.03 g), HPLC purity ≥ 99.92%. Mass spectrometry m / z: 677.2736 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Measured elemental content (%): C, 90.41; H, 5.18; N, 2.04.

[0197] Synthesis Example 14: Preparation of Compound 64

[0198]

[0199] According to the same preparation method as in Synthesis Example 8, replace a-17 with an equimolar amount of a-64 to obtain Compound 64 (13.69 g), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 651.2570 (theoretical value: 651.2562). Theoretical elemental content (%) C49 H 33 NO: C, 90.29; H, 5.10; N, 2.15. Measured elemental content (%): C, 90.32; H, 5.07; N, 2.13.

[0200] Synthesis Example 15: Preparation of Compound 72

[0201]

[0202] According to the same preparation method as in Synthesis Example 8, replace a-17 and b-17 with equimolar a-72 and b-72 respectively to obtain Compound 72 (12.84 g), HPLC purity ≥ 99.98%. Mass spectrometry m / z: 602.2341 (theoretical value: 602.2358). Theoretical elemental content (%) C 44 H 30 N 2 O: C, 87.68; H, 5.02; N, 4.65. Measured elemental content (%): C, 87.70; H, 5.05; N, 4.59.

[0203] Synthesis Example 16: Preparation of Compound 89

[0204]

[0205] According to the same preparation method as in Synthesis Example 8, replace a-17 with equimolar a-89 to obtain Compound 89 (13.49 g), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 651.2548 (theoretical value: 651.2562). Theoretical elemental content (%) C 49 H 33 NO: C, 90.29; H, 5.10; N, 2.15. Measured elemental content (%): C, 90.26; H, 5.08; N, 2.20.

[0206] Synthesis Example 17: Preparation of Compound 110

[0207]

[0208] According to the same preparation method as in Synthesis Example 8, replace a-17 and b-17 with equimolar a-19 and b-24 respectively to obtain Compound 110 (13.71 g), HPLC purity ≥ 99.97%. Mass spectrometry m / z: 643.2884 (theoretical value: 643.2875). Theoretical elemental content (%) C 48 H 37 NO: C, 89.55; H, 5.79; N, 2.18. Measured elemental content (%): C, 89.49; H, 5.82; N, 2.20.

[0209] Synthesis Example 18: Preparation of Compound 159

[0210]

[0211] According to the same preparation method as in Synthesis Example 8, replace b-17 with an equimolar amount of b-159 to obtain Compound 159 (13.60 g), HPLC purity ≥ 99.92%. Mass spectrometry m / z: 629.2732 (theoretical value: 629.2719). Theoretical elemental content (%) C 47 H 35 NO: C, 89.63; H, 5.60; N, 2.22. Measured elemental content (%): C, 89.67; H, 5.57; N, 2.20.

[0212] Synthesis Example 19: Preparation of Compound 167

[0213]

[0214] According to the same preparation method as in Synthesis Example 8, replace c-17 with an equimolar amount of c-167 to obtain Compound 167 (13.62 g), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 677.2707 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Measured elemental content (%): C, 90.40; H, 5.15; N, 2.10.

[0215] Synthesis Example 20: Preparation of Compound 225

[0216]

[0217] According to the same preparation method as in Synthesis Example 8, replace a-17 and c-17 with equimolar amounts of a-19 and c-225 respectively to obtain Compound 225 (13.42 g), HPLC purity ≥ 99.97%. Mass spectrometry m / z: 657.3024 (theoretical value: 657.3032). Theoretical elemental content (%) C 49 H 39 NO: C, 89.46; H, 5.98; N, 2.13. Measured elemental content (%): C, 89.50; H, 5.95; N, 2.11.

[0218] Synthesis Example 21: Preparation of Compound 230

[0219]

[0220] According to the same preparation method as in Synthesis Example 8, a-17 and c-17 were respectively replaced with equimolar amounts of a-19 and c-230 to obtain Compound 230 (14.16 g), with HPLC purity ≥ 99.95%. Mass spectrometry m / z: 693.3047 (theoretical value: 693.3032). Theoretical elemental content (%) C 52 H 39 NO: C, 90.01; H, 5.67; N, 2.02. Measured elemental content (%): C, 90.05; H, 5.62; N, 2.04.

[0221] Synthesis Example 22: Preparation of Compound 235

[0222]

[0223] According to the same preparation method as in Synthesis Example 8, b-17 was replaced with an equimolar amount of b-235 to obtain Compound 235 (11.67 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 525.2074 (theoretical value: 525.2093). Theoretical elemental content (%) C 39 H 27 NO: C, 89.11; H, 5.18; N, 2.66. Measured elemental content (%): C, 89.09; H, 5.22; N, 2.63.

[0224] Synthesis Example 23: Preparation of Compound 320

[0225]

[0226] According to the same preparation method as in Synthesis Example 8, a-17, b-17, and c-17 were respectively replaced with equimolar amounts of a-19, b-235, and c-320 to obtain Compound 320 (13.33 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 643.2862 (theoretical value: 643.2875). Theoretical elemental content (%) C 48 H 37 NO: C, 89.55; H, 5.79; N, 2.18. Measured elemental content (%): C, 89.50; H, 5.81; N, 2.21.

[0227] Synthesis Example 24: Preparation of Compound 334

[0228]

[0229] According to the same preparation method as in Synthesis Example 8, replace a-17, b-17, and c-17 with equimolar amounts of a-19, b-235, and c-334 respectively to obtain Compound 334 (13.52 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 643.2885 (theoretical value: 643.2875). Theoretical elemental content (%) C 48 H 37 NO: C, 89.55; H, 5.79; N, 2.18. Measured elemental content (%): C, 89.57; H, 5.82; N, 2.14.

[0230] Synthesis Example 25: Preparation of Compound 335

[0231]

[0232] According to the same preparation method as in Synthesis Example 8, replace a-17, b-17, and c-17 with equimolar amounts of a-335, b-235, and c-335 respectively to obtain Compound 335 (12.97 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 635.3172 (theoretical value: 635.3188). Theoretical elemental content (%) C 47 H 41 NO: C, 88.78; H, 6.50; N, 2.20. Measured elemental content (%): C, 88.82; H, 6.48; N, 2.17.

[0233] Synthesis Example 26: Preparation of Compound 352

[0234]

[0235] According to the same preparation method as in Synthesis Example 8, replace b-17 and c-17 with equimolar amounts of b-235 and c-352 respectively to obtain Compound 352 (13.33 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 625.2424 (theoretical value: 625.2406). Theoretical elemental content (%) C 47 H 31 NO: C, 90.21; H, 4.99; N, 2.24. Measured elemental content (%): C, 90.19; H, 4.95; N, 2.28.

[0236] Synthesis Example 27: Preparation of Compound 363

[0237]

[0238] According to the same preparation method as in Synthesis Example 8, b-17 and c-17 were respectively replaced with equimolar b-363 and c-363 to obtain Compound 363 (13.49 g), with HPLC purity ≥ 99.98%. Mass spectrometry m / z: 651.2570 (theoretical value: 651.2562). Theoretical elemental content (%) C 49 H 33 NO: C, 90.29; H, 5.10; N, 2.15. Measured elemental content (%): C, 90.32; H, 5.06; N, 2.17.

[0239] Synthesis Example 28: Preparation of Compound 373

[0240]

[0241] According to the same preparation method as in Synthesis Example 8, b-17 was replaced with equimolar b-373 to obtain Compound 373 (13.67 g), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 641.2706 (theoretical value: 641.2719). Theoretical elemental content (%) C 48 H 35 NO: C, 89.83; H, 5.50; N, 2.18. Measured elemental content (%): C, 89.85; H, 5.45; N, 2.21.

[0242] Synthesis Example 29: Preparation of Compound 378

[0243]

[0244] According to the same preparation method as in Synthesis Example 8, b-17 was replaced with equimolar b-378 to obtain Compound 378 (14.23 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 677.2738 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Measured elemental content (%): C, 90.35; H, 5.17; N, 2.12.

[0245] Synthesis Example 30: Preparation of Compound 384

[0246]

[0247] According to the same preparation method as in Synthesis Example 8, a-17 and b-17 were respectively replaced with equimolar amounts of a-19 and b-384 to obtain Compound 384 (13.53 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 617.2730 (theoretical value: 617.2719). Theoretical elemental content (%) C 46 H 35 NO: C, 89.43; H, 5.71; N, 2.27. Measured elemental content (%): C, 89.41; H, 5.69; N, 2.30.

[0248] Synthesis Example 31: Preparation of Compound 387

[0249]

[0250] According to the same preparation method as in Synthesis Example 8, b-17 was replaced with an equimolar amount of b-387 to obtain Compound 387 (13.49 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 651.2546 (theoretical value: 651.2562). Theoretical elemental content (%) C 49 H 33 NO: C, 90.29; H, 5.10; N, 2.15. Measured elemental content (%): C, 90.31; H, 5.06; N, 2.18.

[0251] Synthesis Example 32: Preparation of Compound 392

[0252]

[0253] According to the same preparation method as in Synthesis Example 8, b-17 was replaced with an equimolar amount of b-392 to obtain Compound 392 (12.77 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 625.2417 (theoretical value: 625.2406). Theoretical elemental content (%) C 47 H 31 NO: C, 90.21; H, 4.99; N, 2.24. Measured elemental content (%): C, 90.19; H, 4.96; N, 2.28.

[0254] Synthesis Example 33: Preparation of Compound 405

[0255]

[0256] According to the same preparation method as in Synthesis Example 8, replace b-17 with an equimolar amount of b-405 to obtain Compound 405 (12.84 g), HPLC purity ≥ 99.93%. Mass spectrometry m / z: 602.2365 (theoretical value: 602.2358). Theoretical elemental content (%) C 44 H 30 N 2 O: C, 87.68; H, 5.02; N, 4.65. Measured elemental content (%): C, 87.72; H, 5.04; N, 4.59.

[0257] Synthesis Example 34: Preparation of Compound 412

[0258]

[0259] According to the same preparation method as in Synthesis Example 8, replace a-17 and b-17 with equimolar amounts of a-412 and b-412 respectively to obtain Compound 412 (12.95 g), HPLC purity ≥ 99.98%. Mass spectrometry m / z: 616.2501 (theoretical value: 616.2515). Theoretical elemental content (%) C 45 H 32 N 2 O: C, 87.63; H, 5.23; N, 4.54. Measured elemental content (%): C, 87.66; H, 5.19; N, 4.52.

[0260] Synthesis Example 35: Preparation of Compound 418

[0261]

[0262] According to the same preparation method as in Synthesis Example 8, replace a-17 and b-17 with equimolar amounts of a-19 and b-418 respectively to obtain Compound 418 (13.17 g), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 645.2762 (theoretical value: 645.2780). Theoretical elemental content (%) C 46 H 35 N 3 O: C, 85.55; H, 5.46; N, 6.51. Measured elemental content (%): C, 85.53; H, 5.50; N, 6.48.

[0263] Synthesis Example 36: Preparation of Compound 422

[0264]

[0265] According to the same preparation method as in Synthesis Example 8, replace a-17 and b-17 with equimolar amounts of a-422 and b-422 respectively to obtain Compound 422 (12.11 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 576.2215 (theoretical value: 576.2202). Theoretical elemental content (%) C 42 H 28 N 2 O: C, 87.47; H, 4.89; N, 4.86. Measured elemental content (%): C, 87.50; H, 4.92; N, 4.81.

[0266] Synthesis Example 37: Preparation of Compound 475

[0267]

[0268] According to the same preparation method as in Synthesis Example 8, replace a-17 and c-17 with equimolar amounts of a-475 and c-475 respectively to obtain Compound 475 (13.34 g), with HPLC purity ≥ 99.91%. Mass spectrometry m / z: 617.2194 (theoretical value: 617.2177). Theoretical elemental content (%) C 45 H 31 NS: C, 87.49; H, 5.06; N, 2.27. Measured elemental content (%): C, 87.52; H, 5.01; N, 2.30.

[0269] Synthesis Example 38: Preparation of Compound 502

[0270]

[0271] According to the same preparation method as in Synthesis Example 8, replace a-17 and c-17 with equimolar amounts of a-19 and c-475 respectively to obtain Compound 502 (13.66 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 659.2636 (theoretical value: 659.2647). Theoretical elemental content (%) C 48 H 37 NS: C, 87.37; H, 5.65; N, 2.12. Measured elemental content (%): C, 87.35; H, 5.62; N, 2.17.

[0272] Synthesis Example 39: Preparation of Compound 509

[0273]

[0274] According to the same preparation method as in Synthesis Example 8, a-17, b-17, and c-17 were respectively replaced with equimolar amounts of a-19, b-509, and c-475 to obtain Compound 509 (13.86 g), with HPLC purity ≥ 99.93%. Mass spectrometry m / z: 659.2656 (theoretical value: 659.2647). Theoretical elemental content (%) C 48 H 37 NS: C, 87.37; H, 5.65; N, 2.12. Measured elemental content (%): C, 87.40; H, 5.61; N, 2.14.

[0275] Synthesis Example 40: Preparation of Compound 522

[0276]

[0277] According to the same preparation method as in Synthesis Example 8, a-17 and c-17 were respectively replaced with equimolar amounts of a-522 and c-475 to obtain Compound 522 (13.76 g), with HPLC purity ≥ 99.94%. Mass spectrometry m / z: 645.2476 (theoretical value: 645.2490). Theoretical elemental content (%) C 47 H 35 NS: C, 87.40; H, 5.46; N, 2.17. Measured elemental content (%): C, 87.36; H, 5.48; N, 2.20.

[0278] Synthesis Example 41: Preparation of Compound 588

[0279]

[0280] According to the same preparation method as in Synthesis Example 8, a-17, b-17, and c-17 were respectively replaced with equimolar amounts of a-588, b-235, and c-475 to obtain Compound 588 (12.61 g), with HPLC purity ≥ 99.96%. Mass spectrometry m / z: 583.2354 (theoretical value: 583.2334). Theoretical elemental content (%) C 42 H 33 NS: C, 86.41; H, 5.70; N, 2.40. Measured elemental content (%): C, 86.39; H, 5.67; N, 2.44.

[0281] Synthesis Example 42: Preparation of Compound 596

[0282]

[0283] According to the same preparation method as in Synthesis Example 8, a-17, b-17, and c-17 were respectively replaced with equimolar amounts of a-596, b-596, and c-475 to obtain Compound 596 (12.24 g), with HPLC purity ≥ 99.92%. Mass spectrometry m / z: 574.2483 (theoretical value: 574.2491). Theoretical elemental content (%) C 41 H 26 D 5 NS: C, 85.67; H, 6.31; N, 2.44. Measured elemental content (%): C, 85.70; H, 6.29; N, 2.42.

[0284] Synthesis Example 43: Preparation of Compound 689

[0285]

[0286] Preparation of Intermediate A-689: Under nitrogen protection, a-689 (24.37 g, 50.00 mmol), bis(pinacolato)diboron (12.70 g, 50.00 mmol), K 2 CO 3 (13.82 g, 100.00 mmol), Pd(PPh 3 ) 4 (0.58 g, 0.50 mmol), and 340 mL of dimethylformamide were added to a reaction flask, and the mixture was stirred and reacted under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then recrystallized from toluene / ethanol = 10:1 to obtain Intermediate A-689 (20.85 g, yield 78%), with HPLC purity ≥ 99.84%. Mass spectrometry m / z: 534.2748 (theoretical value: 534.2730).

[0287] Preparation of Compound 689: Under nitrogen protection, A-689 (16.04 g, 30.00 mmol), c-475 (6.42 g, 30.00 mmol), K 2 CO 3 (6.22 g, 45.00 mmol), Pd 2 (dba) 3 (0.27 g, 0.30 mmol), and P(t-Bu) 3(0.12 g, 0.60 mmol), 250 mL of tetrahydrofuran, and stirred and reacted under reflux conditions for 6.5 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered by suction to obtain a filter cake, rinsed with a small amount of toluene, and then the obtained filter cake was recrystallized with toluene to obtain Compound 689 (12.19 g, yield 75%), HPLC purity ≥ 99.98%. Mass spectrometry m / z: 541.1853 (theoretical value: 541.1864). Theoretical elemental content (%) C 39 H 27 NS: C, 86.47; H, 5.02; N, 2.59. Measured elemental content (%): C, 86.50; H, 5.04; N, 2.54.

[0288] Synthesis Example 44: Preparation of Compound 700

[0289]

[0290] According to the same preparation method as in Synthesis Example 43, a-689 and c-475 were respectively replaced with equimolar amounts of a-19 and c-700 to obtain Compound 700 (15.00 g), HPLC purity ≥ 99.95%. Mass spectrometry m / z: 684.2760 (theoretical value: 684.2777). Theoretical elemental content (%) C 49 H 36 N 2 O 2 : C, 85.94; H, 5.30; N, 4.09. Measured elemental content (%): C, 85.91; H, 5.28; N, 4.13.

[0291] Synthesis Example 45: Preparation of Compound 721

[0292]

[0293] According to the same preparation method as in Synthesis Example 8, b-17 and c-17 were respectively replaced with equimolar amounts of b-363 and c-700 to obtain Compound 721 (14.66 g), HPLC purity ≥ 99.92%. Mass spectrometry m / z: 718.2610 (theoretical value: 718.2620). Theoretical elemental content (%) C 52 H 34 N 2 O 2 : C, 86.88; H, 4.77; N, 3.90. Measured elemental content (%): C, 86.90; H, 4.80; N, 3.85.

[0294] Synthesis Example 46: Preparation of Compound 813

[0295]

[0296] According to the same preparation method as in Synthesis Example 8, a-17, b-17, and c-17 were respectively replaced with equimolar amounts of a-19, b-235, and c-813 to obtain Compound 813 (14.47 g), with HPLC purity ≥ 99.97%. Mass spectrometry m / z: 719.3195 (theoretical value: 719.3188). Theoretical elemental content (%) C 54 H 41 NO: C, 90.09; H, 5.74; N, 1.95. Measured elemental content (%): C, 90.11; H, 5.69; N, 1.99.

[0297] Device Example

[0298] In the present invention, the ITO glass substrate and the ITO / Ag / ITO glass substrate were ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. They were ultrasonically cleaned with acetone and isopropanol in sequence for 20 minutes and dried at 120 °C. All organic materials were sublimated and had a purity of over 99.99%.

[0299] A combined IVL test system was composed of a test software, a computer, a K2400 digital source meter produced by Keithley Corporation in the United States, and a PR788 spectral scanning luminance meter produced by PhotoResearch Corporation in the United States to test the driving voltage, luminous efficiency, and CIE color coordinates of the organic electroluminescent device. The lifetime was tested using an M6000 OLED lifetime test system from McScience Corporation. The test environment was an atmospheric environment and the temperature was room temperature.

[0300] Example 1: Preparation of Organic Electroluminescent Device 1

[0301] HI-1 and HI-2 were vacuum-evaporated on the ITO anode, and they formed a hole injection layer at a ratio of HI-1:HI-2 = 5:95 (wt%) with a thickness of 10 nm; HT-1 was vacuum-evaporated as a hole transport layer on the hole injection layer with a thickness of 115 nm; RH-1 and RD-1 were vacuum-evaporated at a ratio of 1:1 (wt%) on the hole transport layer, and they formed a light-emitting layer at a ratio of RH-1:RD-1 = 98:2 (wt%) with a thickness of 30 nm; Compound 17 of the present invention and LiQ were vacuum-evaporated on the light-emitting layer, and they formed an electron transport layer at a ratio of Compound 17 of the present invention:LiQ = 1:1 (wt%) with a thickness of 28 nm; LiF was vacuum-evaporated as an electron injection layer on the electron transport layer with a deposition thickness of 1.0 nm; Al was vacuum-evaporated as a cathode on the electron injection layer with a thickness of 112 nm.

[0302] Examples 2 to 39: Preparation of Organic Electroluminescent Devices 2 to 39

[0303] In Example 1, compound 17 in the electron transport layer was replaced with compound 19, compound 24, compound 38, compound 42, compound 60, compound 64, compound 72, compound 89, compound 110, compound 159, compound 167, compound 225, compound 230, compound 235, compound 320, compound 334, compound 335, compound 352, compound 363, compound 373, compound 378, compound 384, compound 387, compound 392, compound 405, compound 412, compound 418, compound 422, compound 475, compound 502, compound 509, compound 522, compound 588, compound 596, compound 689, compound 700, compound 721, compound 813 respectively, and the other steps were the same, obtaining organic electroluminescent devices 2 to 39.

[0304] Comparative Examples 1 to 4: Preparation of Comparative Organic Electroluminescent Devices 1 to 4

[0305] In Example 1, compound 17 in the electron transport layer was replaced with R-1, R-2, R-3, R-4 respectively, and the other steps were the same, obtaining comparative organic electroluminescent devices 1 to 4.

[0306]

[0307] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 1 to 39 and Comparative Examples 1 to 4 of the present invention are shown in Table 1.

[0308] Table 1 Test Data of Luminescence Characteristics of Organic Electroluminescent Devices

[0309]

[0310]

[0311] Note: T95 refers to the time when the device brightness decays to 95% at a current density of 10 mA / cm 2 in this case;

[0312] It can be seen from Table 1 that compared with the comparative organic electroluminescent devices 1 to 4, the organic electroluminescent devices with the heterocyclic compound of Formula 1 of the present invention in the electron transport layer exhibit lower driving voltage, higher luminous efficiency and longer service life, and the performance of the devices is more excellent.

[0313] Example 40: Preparation of Organic Electroluminescent Device 40

[0314] HI-1 and HI-2 were vacuum-evaporated on the ITO anode, and a hole injection layer was formed with a ratio of HI-1:HI-2 = 5:95 (wt%) and a thickness of 12 nm; HT-1 was vacuum-evaporated on the hole injection layer as a hole transport layer with a thickness of 110 nm; EB-1 was vacuum-evaporated on the hole transport layer as an electron blocking layer with a thickness of 25 nm; GH-1:GH-2:GD-1 = 46:46:8 (wt%) was vacuum-evaporated on the electron blocking layer as a light-emitting layer with a thickness of 30 nm; Compound 17 of the present invention was vacuum-evaporated on the light-emitting layer as a hole blocking layer with a thickness of 20 nm; ET-1:LiQ = 1:1 (wt%) was vacuum-evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; LiF was vacuum-evaporated on the electron transport layer as an electron injection layer with an evaporation thickness of 1.0 nm; Al was vacuum-evaporated on the electron injection layer as a cathode with a thickness of 110 nm.

[0315] Examples 41 to 78: Preparation of Organic Electroluminescent Devices 41 to 78

[0316] Compound 17 in the hole blocking layer of Example 40 was replaced with Compound 19, Compound 24, Compound 38, Compound 42, Compound 60, Compound 64, Compound 72, Compound 89, Compound 110, Compound 159, Compound 167, Compound 225, Compound 230, Compound 235, Compound 320, Compound 334, Compound 335, Compound 352, Compound 363, Compound 373, Compound 378, Compound 384, Compound 387, Compound 392, Compound 405, Compound 412, Compound 418, Compound 422, Compound 475, Compound 502, Compound 509, Compound 522, Compound 588, Compound 596, Compound 689, Compound 700, Compound 721, Compound 813 respectively, and other steps were the same, obtaining Organic Electroluminescent Devices 41 to 78.

[0317] Comparative Examples 5 to 6: Preparation of Comparative Organic Electroluminescent Devices 5 to 6

[0318] Compound 17 in the hole blocking layer of Example 40 was replaced with R-5 and R-6 respectively, and other steps were the same, obtaining Comparative Organic Electroluminescent Devices 5 to 6.

[0319]

[0320] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 40 to 78 and Comparative Examples 5 to 6 of the present invention are shown in Table 2.

[0321] Table 2 Test Data of Luminescence Characteristics of Organic Electroluminescent Devices

[0322]

[0323]

[0324] Note: T97 refers to the time when the device brightness decays to 97% at a current density of 10 mA / cm 2 ;

[0325] As can be seen from Table 2, compared with Comparative Organic Electroluminescent Devices 5-6, the organic electroluminescent device containing the heterocyclic compound of Formula 1 of the present invention in the hole blocking layer exhibits a lower driving voltage, a higher luminous efficiency, and a longer service life. The heterocyclic compound of Formula 1 of the present invention is an excellent hole blocking layer material.

[0326] It should be noted that the present invention has been specifically described with individual embodiments. However, without departing from the principle of the present invention, those of ordinary skill in the art can make various improvements in form or details to the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A heterocyclic compound, characterized in that It is represented by the following formula 1: Among them, the R a Selected from one or more R w One of the following groups substituted: a C6-C30 aromatic group, a C2-C30 heteroaromatic group, a C3-C20 alicyclic group and a C6-C30 aromatic ring fused ring group, wherein R w The same or different ones selected from substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups; The R b One selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group, the "substituted or unsubstituted" substituent is selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused ring group; The z is the same or different from CR c or N, and z bonded to L1 is selected from C atoms; The R c the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring, or two adjacent R c Bonding to form a substituted or unsubstituted ring; Said X is selected from O or S; The R1s are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or two adjacent R1s are bonded to form a substituted or unsubstituted ring; The n1 is selected from 0, 1, 2, 3 or 4; The L1 is selected from one or a combination of a single bond, a substituted or unsubstituted C6-C27 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused sub-ring group; the substituent in the "substituted or unsubstituted arylene group, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring fused sub-ring group" is selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl. , a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring or a combination thereof; the substituent in the "substituted or unsubstituted C2-C30 heteroarylene" is selected from cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl.

2. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound is selected from one of the following formula 1-1 or formula 1-2, 3. The heterocyclic compound according to claim 1, characterized in that Said One selected from the following groups, The R c the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R c Bonding to form a substituted or unsubstituted ring; The R d the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The R w The same or different ones are selected from the group consisting of substituted or unsubstituted groups shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, isobutyl, sec-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, norbornyl; m1 is selected from 0, 1, 2 or 3; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2, 3, 4 or 5; m4 is selected from 0, 1 or 2; m5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; m7 is selected from 0, 1, 2, 3, 4, 5 or 6; m8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; Said p1 is selected from 1, 2, 3, 4 or 5; said p2 is selected from 0, 1, 2, 3 or 4; said p3 is selected from 1, 2, 3, 4, 5, 6 or 7; said p4 is selected from 1, 2 or 3; said p5 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said p6 is selected from 1, 2, 3 or 4; said p7 is selected from 0, 1, 2, 3, 4 or 5; said p8 is selected from 1, 2, 3, 4, 5 or 6; said p9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said p 10 Selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

4. The heterocyclic compound according to claim 1, characterized in that Said One selected from the following groups, Said X is selected from O or S; The R1s are the same or different and are selected from hydrogen, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, methyl ... Alkyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, or two adjacent R1 are bonded to form a substituted or unsubstituted benzene ring; The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the n4 is selected from 0, 1 or 2; the n5 is selected from 0, 1, 2 or 3; the n6 is selected from 0, 1, 2, 3, 4 or 5; the n7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n8 is selected from 0 or 1.

5. The heterocyclic compound according to claim 1, characterized in that The L1 is selected from a single bond or one or a combination of the following groups: The R 20 the same or different selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic fused ring or a combination thereof, or two adjacent R 20 Bonding to form a substituted or unsubstituted ring; The R5 and R6 are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 alicyclic ring and C6-C30 aromatic ring fused ring, or adjacent R5 and R6 are bonded to form a substituted or unsubstituted ring; The y is the same or different and is selected from CR 21 or N, and at least one y is selected from N; The R 21 The same or different R is selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent R 21 Bonding to form a substituted or unsubstituted ring; The v is the same or different from CR 22 or N; The R 22 The same or different R is selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, or two adjacent R 22 Bonding to form a substituted or unsubstituted ring; The T1 is selected from O, S or NR3, the T2 is selected from CR4 or N; the T3 is selected from O, S or NR7; The R3 and R7 are the same or different and are selected from a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a fused ring group of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The R4 is selected from one of hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and a fused ring of a substituted or unsubstituted C3-C20 alicyclic ring and a C6-C30 aromatic ring; The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the t4 is selected from 0, 1, 2 or 3.

6. The heterocyclic compound according to claim 1, characterized in that The L1 is selected from a single bond or one of the following groups, The R 20 The same or different selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilane R, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzoxazolyl, benzothiazolyl, or two adjacent R 20 Bonding to form a substituted or unsubstituted ring; The R 21 , R 22 the same or different selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, or two adjacent R 21 , two R 22 Bonding to form a substituted or unsubstituted ring; The R4s are the same or different and are selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted groups as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropyl Silyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The R5 and R6 are the same or different and are selected from hydrogen, cyano, halogen, nitro, or a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, trimethylsilyl, triethylsilyl, triisopropyl methylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The R7 are the same or different and are selected from one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ethyldimethylsilyl, tert-butyldimethylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl, pyrimidinyl, triazine, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl; The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t4 is selected from 0, 1, 2 or 3; the t5 is selected from 0, 1 or 2; the t6 is selected from 0 or 1; the t7 is selected from 0, 1, 2, 3, 4 or 5; the t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the t9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

7. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound is selected from one of the structures shown below:

8. An organic electroluminescent device, characterized in that: The organic electroluminescent device contains the heterocyclic compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the heterocyclic compound according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode, and the organic layer includes an electron transport region, wherein the electron transport region contains the heterocyclic compound according to any one of claims 1 to 7.

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