Organic light-emitting device

Abstract

The invention provides an organic electroluminescent device, and belongs to the technical field of organic electroluminescence. According to the organic light-emitting device provided by the invention, specific structures are introduced into the hole transmission region and the electron transmission region, and the interaction of the hole transmission region and the electron transmission region can prevent holes / electrons from moving to adjacent organic matter layers, so that the light-emitting efficiency of the organic light-emitting device is greatly improved, and the service life of the device is further prolonged. The organic light-emitting device has a good application effect and a good industrialization prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescence, in particular to an organic electroluminescence device. BACKGROUND

[0002] Organic Light-Emitting Diode (OLED) refers to a device in which organic optoelectronic material emits light under the action of current or electric field, which can directly convert electric energy into light energy. Since OLED has the advantages of full-spectrum color, high brightness, high efficiency, flexible display, fast response speed and the like, it has been widely applied in display and lighting fields.

[0003] OLED generally comprises an anode, a cathode and an organic layer between or outside the two electrodes. The organic layer is usually formed by a multilayer structure composed of different materials, such as a hole transport region, a light-emitting layer, an electron transport region, a cover layer, etc., wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, etc., and the electron transport region includes an electron injection layer, an electron transport layer, a hole blocking layer, etc. Such a multilayer structure can further improve the light-emitting efficiency and stability of the device.

[0004] With the gradual increase in the size of the display, the light-emitting efficiency and service life of the OLED device are facing severe challenges. At present, the organic electroluminescence device still has poor performance in use, for example, there are problems such as too low light-emitting efficiency or too short service life, which affect the use field of OLED. Therefore, it is still necessary to further study this field to improve the performance of the organic electroluminescence device. SUMMARY

[0005] In order to solve the problems of too low light-emitting efficiency and too short service life of the organic electroluminescence device, the present application provides an organic electroluminescence device, which comprises an anode, a hole transport region, a light-emitting layer, an electron transport region and a cathode, wherein the hole transport region comprises a structure represented by formula 1, and the electron transport region comprises a structure represented by formula 2,

[0006]

[0007] In formula 1,

[0008] Ar1-Ar4 are the same or different and are selected from any one of the following structures,

[0009]

[0010] The ring A is selected from a substituted or unsubstituted C3-C12 alicyclic ring or a substituted or unsubstituted C2-C12 aliphatic heterocyclic ring.

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

[0012] The Ra and Rb are the same or different from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C2-C12 heterocycloalkyl groups, substituted or unsubstituted C3-C12 cycloalkenyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic fused cycloyl groups, substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaromatic fused cycloyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C12 alkoxy groups, or Ra and Rb form substituted or unsubstituted spirocyclic groups;

[0013] The R6 is the same as or different from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C1-C12 alkoxy.

[0014] The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R6, the two or more R6 are the same or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted alicyclic ring, or a substituted or unsubstituted alicyclic heterocyclic ring;

[0015] The L0 is selected from any one or a combination of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaromatic rings.

[0016] In Equation 2,

[0017] The R1 and R2 are the same or different and are selected from any one of the following: C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocyclic alkyl, C3-C12 cycloalkenyl, C6-C30 aryl, C3-C12 alicyclic and C6-C30 aromatic fused cycloyl, silyl, and C1-C12 alkoxy; or R1 and R2 are connected to each other to form substituted or unsubstituted rings;

[0018] R1, R2may be substituted by one or more substituents selected from any one of deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic, substituted or unsubstituted silyl group; when two or more substituents are present, the two or more substituents are the same as or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted ring;

[0019] z is the same or different, selected from CH or N, z bonded to L1is selected from C atom;

[0020] R3, R4are the same or different, selected from any one of hydrogen, deuterium, cyano, halogen, methyl, trifluoromethyl, C3-C12cycloalkyl, C2-C12heterocycloalkyl, C3-C12cycloalkenyl, C6-C30aryl, C2-C30heteroaryl, fused ring group of C3-C12alicyclic and C6-C30aromatic, fused ring group of C3-C12alicyclic and C2-C30heteroaromatic, substituted or unsubstituted silyl group;

[0021] R3, R4may be substituted by one or more substituents selected from any one of deuterium, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic, substituted or unsubstituted silyl group; when two or more substituents are present, the two or more substituents are the same as or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted ring;

[0022] a, b are the same or different, selected from 0, 1, 2, 3 or 4; when two or more R3, R4are present, the two or more R3, R4are the same as or different from each other, or adjacent two R3, R4are connected to each other to form a substituted or unsubstituted ring;

[0023] L1is selected from any one of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, and substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group;

[0024] L2is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, and substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group;

[0025] X is selected from O, S or N(Rc);

[0026] Rcis selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group, substituted or unsubstituted silyl, and substituted or unsubstituted C1-C12 alkoxy;

[0027] x is the same or different and is selected from C(R7) or N;

[0028] R7is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, and substituted or unsubstituted silyl; when there are two or more R7, the two or more R7are the same as or different from each other, or adjacent two R7are connected to each other to form a substituted or unsubstituted ring;

[0029] R5 is selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted fused ring group of C3-C12 alicyclic and C2-C30 heteroaromatic ring, and substituted or unsubstituted silyl group.

[0030] Advantages of the present application:

[0031] The organic electroluminescent device provided by the present application introduces structure 1 in the hole transport region and structure 2 in the electron transport region, and the combination of the two can avoid the movement of holes / electrons to the adjacent organic layer, effectively limits the holes / electrons in the light-emitting layer, not only can improve the recombination probability of excitons, but also can move the exciton recombination region to the center of the light-emitting layer, the interaction of the two greatly improves the luminous efficiency of the organic electroluminescent device, and prolongs the service life of the device. DETAILED DESCRIPTION

[0032] In order to make the objects, technical solutions and advantages of the embodiments of the present application clearer, the technical solutions of the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are part of the embodiments of the present application, rather than all the embodiments. And in the case of no conflict, the embodiments in the present application and the features in the embodiments can be combined with each other. Based on the described embodiments of the present application, all other embodiments obtained by those of ordinary skill in the art without creative labor belong to the scope of protection of the present application.

[0033] Unless otherwise defined, technical terms or scientific terms used in the present application shall be understood as the usual meaning understood by those of ordinary skill in the art to which the present application belongs. The "including" or "containing" and similar words used in the present application mean that the devices or objects before the words cover the devices or objects listed after the words and their equivalents, and do not exclude other devices or objects. The "connection" or "connection" and similar words are not limited to physical or mechanical connection, but can include electrical connection, whether direct or indirect. "In", "out", "up", "down" and the like are only used to indicate relative positional relationship, when the absolute position of the described object changes, the relative positional relationship may also change accordingly.

[0034] In the compounds of the present application, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0035] In the present specification, “*-” means a moiety connected to another substituent.

[0036] In the present specification, when a substituent or a bonding site is indicated to be on a bond that extends through two or more rings, it is indicated that it can be connected to any one of the two or more rings, specifically, to any one of the corresponding optional sites of the rings. For example, may be represented by may be represented by and so on.

[0037] In the present specification, when the position of a substituent on a ring is not fixed, it is indicated that it can be connected to any one of the corresponding optional sites of the ring.

[0038] For example, may be represented by may be represented by may be represented by and so on.

[0039] The halogen according to the present application means fluorine, chlorine, bromine, iodine;

[0040] The alkyl according to the present application means a monovalent group in which one hydrogen atom of an alkane molecule is removed, and can be a straight-chain alkyl group or a branched-chain alkyl group, preferably has 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 10 carbon atoms, and particularly preferably 1 to 6 carbon atoms, and examples can include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a hexyl group, and the like, but are not limited thereto.

[0041] The cycloalkyl according to the present application means a monovalent group in which one hydrogen atom of a cycloalkane molecule is removed, and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, and preferably 3 to 7 carbon atoms, and examples can include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, and the like, but are not limited thereto.

[0042] The heterocycloalkyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a heterocycloalkane molecule, and the heteroatom can be one or more of N, O, S, Si, and P. Preferably, it has 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, preferably 3 to 5 carbon atoms, and examples can include azetidinyl, tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothiophenyl, piperidinyl, azepanyl, homopiperidinyl, morpholinyl, thiomorpholinyl, dioxanyl, and the like, but are not limited thereto.

[0043] The cycloalkenyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a cycloalkene molecule, and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, and examples can include cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like, but are not limited thereto.

[0044] The aryl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from the aromatic nucleus of an aromatic hydrocarbon molecule, and can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, and preferably has 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, most preferably 6 to 12 carbon atoms, and examples can include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, anthryl, phenanthryl, pyrenyl, triphenylenyl, perylenyl, and the like, but are not limited thereto.

[0045] The fused ring group of the aliphatic ring and the aromatic ring according to the present application refers to a general term for a monovalent group obtained by removing one hydrogen atom from the aliphatic ring and the aromatic ring after being fused together. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, most preferably 7 to 13 carbon atoms, and examples can include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like, but are not limited thereto.

[0046] The heteroaryl group according to the present application refers to a group of removing one hydrogen atom from the core atom of the aromatic heterocycle composed of carbon and heteroatom. The heteroatom can be one or more of N, O, S, Si, P, and can be a monocyclic heteroaryl group or a fused ring heteroaryl group, preferably having 1 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 16 carbon atoms, particularly preferably 3 to 12 carbon atoms, most preferably 3 to 8 carbon atoms, and examples can include pyrrolyl, pyridyl, pyrimidyl, triazinyl, thienyl, furanyl, indolyl, quinolyl, isoquinolyl, oxazolyl, thiazolyl, imidazolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, pyridyloxazolyl, pyridylthiazolyl, pyridylimidazolyl, pyrimidyloxazolyl, pyrimidylthiazolyl, pyrimidylimidazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenoxazinyl, quinoxalyl, quinazolyl, quinolyloxazolyl, quinolylthiazolyl, quinolyylimidazolyl, purinyl, 2-purinyl, N-imidazolyl, etc., but is not limited thereto.

[0047] The fused ring group of the alicyclic and heteroaromatic ring according to the present application refers to a group of removing one hydrogen atom from the alicyclic and heteroaromatic ring fused together. Preferably, it has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, most preferably 5 to 12 carbon atoms, and examples can include pyridinocyclopropyl, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinobenzocycloheptyl, pyrimidinocyclopropyl, pyrimidinocyclobutyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, pyrimidinobenzocycloheptyl, dibenzofuranylcyclopropyl, dibenzofuranylcyclobutyl, dibenzofuranylcyclopentyl, dibenzofuranylcyclohexyl, dibenzofuranylcycloheptyl, dibenzothienylcyclopropyl, dibenzothienylcyclobutyl, dibenzothienylcyclopentyl, dibenzothienylcyclohexyl, dibenzothienylcycloheptyl, carbazolocyclopropyl, carbazolocyclobutyl, carbazolocyclopentyl, carbazolocyclohexyl, carbazolocycloheptyl, etc., but is not limited thereto.

[0048] The "substituted or unsubstituted silyl group" according to the present application refers to a —Si(R k )3 group, wherein each R k is the same or different selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted fused ring group of C3-C30 alicyclic and C6-C60 aromatic ring, and substituted or unsubstituted fused ring group of C3-C30 alicyclic and C2-C60 heteroaromatic ring. Preferably, each R kthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 30, preferably 6 to 18, more preferably 6 to 14, and most preferably 6 to 12. Preferably, each R k the same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.

[0049] The alkoxy group according to the present application refers to a monovalent group in which one hydrogen atom is removed from an alkoxy hydrocarbon molecule, and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, and examples can include methoxy, ethoxy, propoxy, butoxy, pentoxy, etc., but are not limited thereto.

[0050] The alicyclic group according to the present application refers to an alicyclic hydrocarbon molecule, which can be a cycloalkane, a cycloalkene, a cycloalkyne, etc., and preferably has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, and examples can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto.

[0051] The aliphatic heterocyclic group according to the present application refers to an aliphatic heterocyclic hydrocarbon molecule, and the heteroatom can be one or more of N, O, S, Si, P. Preferably, it has 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, preferably 3 to 12 carbon atoms, preferably 3 to 7 carbon atoms, and examples can include azetidine, tetrahydropyrrole, tetrahydrofuran, tetrahydrothiophene, piperidine, azepane, homopiperidine, morpholine, thiomorpholine, dioxane, etc., but are not limited thereto.

[0052] The arylene group described in this invention refers to an aryl group with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they can be described in the same way as the aryl group described above.

[0053] The fused ring groups of aromatic and alicyclic compounds described in this invention refer to fused ring groups of aromatic and alicyclic compounds with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they are subject to the above description of fused ring groups of aromatic and alicyclic compounds.

[0054] The heteroaryl group described in this invention refers to a heteroaryl group with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they can be described as heteroaryl groups as described above.

[0055] The fused ring groups of heteroaromatic and alicyclic rings described in this invention refer to fused ring groups of heteroaromatic and alicyclic rings with two bonding sites, i.e., divalent groups. Apart from being divalent groups, they are subject to the above description of fused ring groups of heteroaromatic and alicyclic rings.

[0056] The term "substitution" as used in this invention refers to the replacement of hydrogen atoms in a compound group with other atoms or groups, and the substitution position is not limited.

[0057] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: protium, deuterium, tritium, cyano, halogen atom, amino, nitro, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C30 alicyclic, substituted or unsubstituted C1-C25 heterocyclic alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C1-C25 heterocyclic alkanes and C6-C30 aromatic ring fused cycloyl groups, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring fused cycloyl groups, substituted or unsubstituted silyl, substituted or unsubstituted The substituted C6-C30 arylamine group, substituted or unsubstituted C6-C30 aryloxy group, preferably protium, deuterium, tritium, halogen atom, cyano, C1-C12 alkyl, C3-C18 alicyclic, C6-C25 aryl, C2-C25 heteroaryl, and specific examples may include protium, deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl Cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, tolyl, mesitylelel, pentadeuterated phenyl, biphenyl, naphthyl, anthracene, phenanthrene, benzophenanthrene, pyrene, phenylenetriene carbazolyl, 9-phenylcarbazolyl, spirobifluorenyl, carbazolinoindolyl, pyrrolyl, furanyl, thienyl, indolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, pyridyloxazolyl, pyridylthiazolyl, pyridylimidazolyl, pyrimidinyloxazolyl, pyrimidylthiazolyl, pyrimidylimidazolyl, quinolyl, isoquinolyl, quinolyloxazolyl, quinolythiazolyl, quinolyimidazolyl, phenothiazyl, phenoxazyl, acridyl, and the like, but are not limited thereto. Alternatively, when the substituent is two or more, adjacent substituents can be bonded to form a ring; when the substituent is two or more, the plurality of substituents can be the same as or different from each other.

[0058] The connection to form a substituted or unsubstituted ring according to the present application means that two groups are connected to each other by a chemical bond and optionally aromatized. Examples are as follows:

[0059]

[0060] In the present application, the ring formed by the connection can be a five-membered ring or a six-membered ring or a fused ring, and examples can include benzene, pyridine, pyrimidine, naphthalene, fluorene, cyclopentene, cyclohexene, cyclopentane, cyclohexane, cyclohexanobenzene, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0061] The following describes embodiments of the organic electroluminescent device according to the present application, but the embodiments of the present application can be modified into other forms, and the scope of the present application is not limited by the embodiments described below.

[0062] The organic electroluminescent device according to the present application includes an anode, a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region is located between the anode and the light-emitting layer, the electron transport region is located between the light-emitting layer and the cathode, the hole transport region includes a structure represented by Formula 1, and the electron transport region includes a structure represented by Formula 2.

[0063] Hereinafter, the configuration of the organic electroluminescent device having the hole transport region and the electron transport region will be described in more detail.

[0064] The thickness of each organic layer of the organic electroluminescent device according to the present application is not particularly limited, and a thickness commonly used in the art can be used.

[0065] Anode

[0066] In the organic electroluminescent device according to the present application, the anode preferably uses a high work function material (work function of more than 4.0 eV) capable of promoting hole injection into other functional layers, and specific examples of the anode material usable in the present application can include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as indium tin oxide-silver-indium tin oxide (ITO-Ag-ITO); conductive polymers such as poly(3-methylthiophene), polypyrrole, polyaniline, poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), and the like, but are not limited thereto.

[0067] Organic layer

[0068] In the organic electroluminescent device according to the present application, the organic layer can be used without limitation by the conventional configuration used as the organic layer of the organic electroluminescent device, and can include one or more selected from the group consisting of a hole transport region, a light emitting layer, and an electron transport region.

[0069] Hole transport region

[0070] In the organic electroluminescent device according to the present application, the hole transport region included therein functions to move holes injected from the anode to the light emitting layer.

[0071] The hole transport region includes a structure represented by Formula 1,

[0072]

[0073] Ar1 to Ar4 are the same or different and are selected from any one of the structures represented by the following formulae,

[0074]

[0075] The ring A is selected from a substituted or unsubstituted C3 to C12 alicyclic ring or a substituted or unsubstituted C2 to C12 aliphatic heterocyclic ring.

[0076] d is selected from 1, 2, 3, 4, or 5.

[0077] Ra, Rbare the same or different and selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy, or Ra, Rb form a substituted or unsubstituted spiro ring;

[0078] R6is the same or different and selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy;

[0079] c1is selected from 0, 1, 2, 3, 4 or 5; c2is selected from 0, 1, 2, 3 or 4; c3is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; c5is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R6, the two or more R6are the same or different from each other, or two adjacent R6are connected to each other to form a substituted or unsubstituted alicyclo ring, a substituted or unsubstituted alicyclohetero ring;

[0080] L0is selected from any one of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroaryl, or a combination thereof;

[0081] Preferably, Ar1-Ar4are the same or different and selected from any one of the following structures,

[0082]

[0083]

[0084]

[0085] R6is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, furanyl, thienyl, benzofuranyl, benzothienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0086] R6may be substituted with one or more substituents selected from the group consisting of deuterium, cyano, halogen, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, furanyl, thienyl, benzofuranyl, benzothienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0087] c1is selected from 0, 1, 2, 3, 4, or 5; c2is selected from 0, 1, 2, 3, or 4; c3is selected from 0, 1, 2, 3, 4, 5, 6, or 7; c4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; c5is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; c6is selected from 0, 1, 2, or 3; c7is selected from 0, 1, or 2; c8is selected from 0, 1, 2, 3, 4, 5, or 6; c9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10;

[0088] d1is independently selected from 1, 2, 3, or 4.

[0089] Preferably, L0is selected from any one of the following structures,

[0090]

[0091]

[0092] Rd1, Rd2, Re1, Re2, Rf1, Rf2are the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy;

[0093] R8is selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy;

[0094] e1is selected from 0, 1, 2, 3 or 4; e2is selected from 0, 1, 2, 3, 4, 5 or 6; e3is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; e4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; e5is selected from 0, 1, 2 or 3; e6is selected from 0, 1 or 2; e7is selected from 0, 1, 2, 3, 4 or 5; e8is selected from 0, 1, 2, 3, 4, 5, 6 or 7; e9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; e 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; when there are two or more R8, the two or more R8are the same or different from each other, or two adjacent R8are connected to each other to form a substituted or unsubstituted ring. Preferably, the formula 1 is selected from any one of the following structures,

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] The hole transport region can be at least one of an electron blocking layer, a hole injection layer, or a hole transport layer, at least one of which comprises a structure represented by Formula 1.

[0121] The hole transport region can be a hole transport layer comprising a structure represented by Formula 1.

[0122] Preferably, the hole transport layer has a thickness of 30 nm to 200 nm, more preferably 60 nm to 150 nm.

[0123] The hole transport region can have an electron blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer and a hole injection layer, a hole transport layer and a hole injection layer, an electron blocking layer and a hole transport layer, or a structure having an electron blocking layer, a hole transport layer and a hole injection layer, with reference to the light emitting layer. Preferably, the hole transport region comprises an electron blocking layer, a hole transport layer and a hole injection layer.

[0124] The hole injection layer according to the present application preferably uses a material having a good hole accepting ability. Specific examples of the hole injection layer material that can be used in the present application can include silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide and other metal oxides, phthalocyanine compounds, benzidine compounds, phenazine compounds and other materials such as copper phthalocyanine (CuPc), titanium phthalocyanine oxide, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD), diquinoxalino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), and the like, but are not limited thereto.

[0125] The hole transport layer according to the present application preferably uses a material having a good hole transport property. Specific examples of the hole transport layer material that can be used in the present application can include diphenylamine compounds, triphenylamine compounds, fluorene compounds, carbazole compounds and other materials such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthalen-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)benzenamine (TAPC), and the like, but are not limited thereto. Preferably, the hole transport layer according to the present application is selected from the structure represented by Formula 1.

[0126] The electron blocking layer according to the present application preferably uses a material having a good electron blocking property. Specific examples of the electron blocking layer material that can be used in the present application can include diphenylamine-based compounds, triphenylamine-based compounds, fluorene-based compounds, triarylamine-based compounds, and carbazole-based compounds, and the like, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthalen-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (a-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), and the like, but are not limited thereto. Preferably, the electron blocking layer according to the present application is selected from the structures represented by Formula 1

[0127] Light emitting layer

[0128] In the organic electroluminescent device according to the present application, the light-emitting layer is a layer in which holes and electrons meet to form excitons, and the color of light emitted from the organic electroluminescent device can be changed depending on the substance constituting the light-emitting layer. The light-emitting layer includes a host material and a dopant material, and the mixing ratio thereof can be appropriately adjusted within a range known in the art. The light-emitting layer can include 70 to 99.9 parts by weight of the host material and 0.1 to 30 parts by weight of the dopant material, based on the total weight of the light-emitting layer. Preferably, in the case where the light-emitting layer is blue fluorescent, green fluorescent, or red fluorescent, the light-emitting layer can include 80 to 99.9 parts by weight of the host material and 0.1 to 20 parts by weight of the dopant material. Preferably, in the case where the light-emitting layer is blue fluorescent, green fluorescent, or red phosphorescent, the light-emitting layer can include 70 to 99 parts by weight of the host material and 1 to 30 parts by weight of the dopant material. The host material included in the light-emitting layer according to the present application can be a host material known in the art, and can be an alkali metal complex compound, an alkaline earth metal complex compound, or a condensed aromatic ring derivative, etc. Specific examples of the host material that can be used in the present application can include one or a combination of one or more of an aluminum complex compound, a beryllium complex compound, an anthracene derivative, a pyrene derivative, a triphenylene derivative, a carbazole derivative, a dibenzofuran derivative, a dibenzothiophene derivative, such as 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazolyl)-2,2'-biphenyl (CPB), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (a-ADN), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"'-quaterphenyl]-4,4"-diamine (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (TBADN), 2,7-bis[9,9-di(4-methylphenyl)-2- fluorenyl]-9,9-di(4-methylphenyl)fluorene (TDAF), 2-methyl-9,10-bis(2-naphthyl)anthracene (MADN), 9,9',10,10'-tetraphenyl-2,2'-bisanthracene (TPBA), 10,10'-di(4-biphenylyl)-9,9'-bianthracene (BANE), 4,4'-di[10-(1-naphthyl)9-anthryl]biphenyl (BUBH-3), 1-(7-(9,9'-anthryl)-9,9-dimethyl-9H-2-fluorenyl)pyrene (BAnFPye), 9,10-diphenylanthracene (ADP), 2-methyl-9,10-di(1-naphthyl)anthracene (MAD-1N), 4,4'-bis(9-carbazolyl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(9-carbazolyl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetrakis(9-carbazolyl)-9,9-spirobifluorene (Spiro-CBP), 9,9-bis[4-(9-carbazolyl)-phenyl]fluorene (FL-2CBP), 2,6-bis(3-(9H-9-carbazolyl)phenyl)pyridine (26DCzPPy), 3,5-di(9H-9-carbazolyl)biphenyl (Ph-MCP), 3-(3-(9H-9-carbazolyl)phenyl)benzofuran[2,3-b]pyridine (PCz-BFP), 2,6-di(9H-9-carbazolyl)pyridine (PYD-2Cz), 3-(4-(9H-9-carbazolyl)phenyl)-9-(4,6-diphenyl-1,3,5-2-triazinyl)-9H-carbazole (CPCBPTz), 4,6-bis(3-(9H-9-carbazolyl)phenyl)pyrimidine (46DCzPPM), 9-(3,5-di(2-triphenyl-yl)phenyl)-9H-carbazole (DTP-mCP), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), and the like, but are not limited thereto. The dopant material contained in the light-emitting layer according to the present application can be a dopant material known in the art, which can be a red dopant material, a green dopant material, and a blue dopant material. The red dopant material can be one or a combination of more than one of octaethylporphyrin platinum (II) (PtOEP), tris(2-phenylisoquinoline)iridium (Ir(piq)3), bis(2-(2'-benzothienyl)-pyridine-N,C3')(acetylacetonate)iridium) (Btp2Ir(acac)); the green dopant material can be one or a combination of more than one of tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)(acetylacetonate)iridium (III) (Ir(ppy)2(acac)), tris(2-(4-methylphenyl)phenylpyridine)iridium (Ir(mppy)3), 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7,-tetrahydro-1H,5H,11H-[1]benzopyranophan[6,7,8-ij]-quinolizine-11-one (C545T); and the blue dopant material can be one or a combination of more than one of bis[3,5-difluoro-2-(2-pyridyl)phenyl(pyridinecarbonyl)iridium (III) (F2Irpic), 4,4'-bis(2,2'-diphenylvinyl-1-yl)biphenyl (DPVBi), 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0129] The light-emitting layer according to the present application can be a single layer composed of one kind of substance, a single layer composed of a plurality of kinds of substances different from each other, or a plurality of layers composed of different substances from each other. In the case where the light-emitting layer is a plurality of layers, the organic electroluminescent device can emit light of a plurality of colors.

[0130] The organic electroluminescent device according to the present application can have a plurality of light-emitting layer stacks each of which includes at least one light-emitting layer. The plurality of light-emitting layers included in the light-emitting layer stack can be light-emitting layers each of which emits light of a color different from each other or light-emitting layers each of which emits light of the same color. That is, the emission color can be changed depending on the substance constituting the light-emitting layer. For example, the plurality of light-emitting layer stacks can include a substance which emits light of blue, green, red, yellow, white, or the like, and can be formed using a phosphorescent or fluorescent substance. At this time, the colors emitted from the respective light-emitting layers can be in a complementary color relationship. In addition to this, the colors can be selected in accordance with the combination of colors from which white light can be emitted.

[0131] Electron transport region

[0132] In the organic electroluminescent device according to the present application, the electron transport region functions to move the electrons injected from the cathode to the light-emitting layer.

[0133] The electron transport region according to the present application includes a structure represented by Formula 2,

[0134]

[0135] R1and R2are the same or different and selected from any one of C1to C12alkyl, C3to C12cycloalkyl, C2to C12heterocycloalkyl, C3to C12cycloalkenyl, C6to C30aryl, C3to C12alicyclic and C6to C30aromatic fused ring group, silyl group, C1to C12alkoxy; or R1and R2are connected to each other to form a substituted or unsubstituted ring;

[0136] R1 and R2 can be replaced by one or more substituents, wherein the substituents are selected from any one of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloyl group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, fused cycloyl group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl rings, and substituted or unsubstituted silyl; when two or more substituents are present, the two or more substituents are the same as or different from each other, or two adjacent substituents are connected to each other to form substituted or unsubstituted alicyclic or substituted or unsubstituted alicyclic heterocyclic rings;

[0137] The z atoms that are the same or different are selected from CH or N, and the z atoms that are bonded to L1 are selected from C atoms;

[0138] The same or different R3 and R4 are selected from any one of hydrogen, deuterium, cyano, halogen, methyl, trifluoromethyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C30 aryl, C2-C30 heteroaryl, fused cycloyl group of C3-C12 alicyclic and C6-C30 aromatic rings, fused cycloyl group of C3-C12 alicyclic and C2-C30 heteroaryl rings, substituted or unsubstituted silyl groups;

[0139] R3 and R4 can be replaced by one or more substituents selected from deuterium, halogens, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C2-C12 heterocycloalkyl groups, substituted or unsubstituted C3-C12 cycloalkenyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloyl groups of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, fused cycloyl groups of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaromatic rings, and substituted or unsubstituted silyl groups; when two or more substituents are present, the two or more substituents are the same as or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted ring;

[0140] The same or different a and b are selected from 0, 1, 2, 3 or 4; when there are two or more R3 and R4, the two or more R3 and R4 are the same or different from each other, or two adjacent R3 and R4 are connected to each other to form a substituted or unsubstituted ring;

[0141] L1is selected from any one of substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, and substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group;

[0142] L2is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, and substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group;

[0143] X is selected from O, S or N(Rc);

[0144] Rcis selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heterocyclo fused ring group, substituted or unsubstituted silyl, and substituted or unsubstituted C1-C12 alkoxy;

[0145] x is the same or different and is selected from C(R7) or N;

[0146] R7is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, and substituted or unsubstituted silyl; when there are two or more R7, the two or more R7are the same as or different from each other, or adjacent two R7are connected to each other to form a substituted or unsubstituted ring;

[0147] R5is selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic, substituted or unsubstituted silyl group.

[0148] Preferably, the R1, R2are the same or different and are selected from any one of C1-C12alkyl, C3-C12cycloalkyl, C2-C12heterocycloalkyl, C3-C12cycloalkenyl, C6-C30aryl, C3-C12alicyclic and C6-C30aromatic fused ring group, silyl group, C1-C12alkoxy group. is selected from any one of the following structures,

[0149]

[0150] z is the same or different and is selected from CH or N, z bonded to L1is selected from C;

[0151] R1, R2are the same or different and are selected from any one of C1-C12alkyl, C3-C12cycloalkyl, C2-C12heterocycloalkyl, C3-C12cycloalkenyl, C6-C30aryl, C3-C12alicyclic and C6-C30aromatic fused ring group, silyl group, C1-C12alkoxy group.

[0152] R1, R2may be substituted by one or more substituents selected from any one of deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic, substituted or unsubstituted silyl group; when there are two or more substituents, the two or more substituents are the same or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted aliphatic ring, a substituted or unsubstituted aliphatic heterocyclic ring.

[0153] R2’ is selected from any one of single bond, substituted or unsubstituted C3-C12cycloalkylene, substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene, substituted or unsubstituted C3-C12alicyclic and C6-C30aromatic fused ring group, substituted or unsubstituted C3-C12alicyclic and C2-C30heteroaromatic fused ring group, or a combination thereof.

[0154] R3, R4, which are the same or different, are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroaryl, substituted or unsubstituted silyl group;

[0155] R9, which are the same or different, are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroaryl, substituted or unsubstituted silyl group;

[0156] b is selected from 0, 1, 2, 3 or 4; when two or more R3s exist, the two or more R3s are the same or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0157] a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; when two or more R4s exist, the two or more R4s are the same or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0158] f1 is selected from 0, 1, 2, 3 or 4; f2 is selected from 0, 1, 2, 3, 4, 5 or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; f6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when two or more R9s exist, the two or more R9s are the same or different from each other, or two adjacent R9s are connected to each other to form a substituted or unsubstituted ring;

[0159] Rg, Rh, Ri are independently selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl group.

[0160] Preferably, in each six-membered ring containing z, at most 2 or at most 1 z is selected from N.

[0161] Preferably, in each structure, at most 2 or at most 1 z is selected from N.

[0162] Preferably, R1, R2 are independently selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, benzo-cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0163] R1, R2 can be substituted with one or more substituents selected from any one or combination of deuterium, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclic and C6-C30 aromatic, fused ring group of C3-C12 alicyclic and C2-C30 heteroaromatic, substituted or unsubstituted silyl group; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0164] Preferably, at least one of R1, R2 is C1-C12 alkyl-substituted C6-C30 aryl;

[0165] Preferably, at least one of R1, R2 is C1-C12 alkyl-substituted phenyl;

[0166] R2' is selected from any one or combination of single bond, benzo-cyclopropylene, benzo-cyclobutylene, benzo-cyclopentylene, benzo-cyclohexylene, benzo-cycloheptylene, benzo-cyclopentenylene, benzo-cyclohexenylene, phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, triphenylene, fluorenylene, carbazolylene, furanylene, thienylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, pyridylene, pyrimidinylene, triazinylene, quinolinylene, isoquinolinylene, quinazolinylene, quinoxalinylene, phenanthrolinylene, benzoxazolylene, benzothiazolylene.

[0167] R2' can be substituted with one or more substituents selected from any one of or a combination of deuterium, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, fused ring group of C3-C12 alicyclo and C2-C30 heterocyclo, substituted or unsubstituted silyl group, and the like; when there are two or more substituents, the two or more substituents are the same as or different from each other;

[0168] R3, R4 are the same or different and selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, diphenylene furan, diphenylene thiophene, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, and the like;

[0169] R9 is the same or different and selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, t-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, diphenylene furan, diphenylene thiophene, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, and the like;

[0170] R3, R4, R9may be substituted by one or more substituents selected from any one of deuterium, halogen, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, benzo- cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same as or different from each other;

[0171] b is selected from 0, 1, 2, 3 or 4; when there are two or more R3, the two or more R3are the same as or different from each other, or two adjacent R3are connected to each other to form a substituted or unsubstituted ring;

[0172] a1is selected from 0, 1, 2 or 3; a2is selected from 0, 1, 2, 3 or 4; when there are two or more R4, the two or more R4are the same as or different from each other, or two adjacent R4are connected to each other to form a substituted or unsubstituted ring;

[0173] f1is selected from 0, 1, 2, 3 or 4; f2is selected from 0, 1, 2, 3, 4, 5 or 6; f3is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; f4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; f5is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; f6is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R9, the two or more R9are the same as or different from each other, or two adjacent R9are connected to each other to form a substituted or unsubstituted ring;

[0174] Rg, Rh, and Ri are the same or different and are selected from any one of the following: methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0175] Rg, Rh, and Ri can be substituted with one or more substituents selected from any one or a combination of deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl group, and the like; when there are two or more substituents, the two or more substituents are the same or different from each other.

[0176] Preferably, L1is selected from any one of the following structures,

[0177]

[0178] y is the same or different and is selected from CH or N;

[0179] R 10 the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C12 alkoxy, and the like;

[0180] said h1 is the same or different selected from 0, 1, 2, 3, or 4; said h2 is the same or different selected from 0, 1, 2, or 3; said h3 is the same or different selected from 0, 1, or 2; said h4 is the same or different selected from 0, 1, 2, 3, 4, 5, or 6; said h5 is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8;

[0181] said Rj, Rk, Rm is the same or different selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy.

[0182] Preferably, in each six-membered ring containing y, at most 2 or at most 1 y is selected from N.

[0183] Preferably, at most 2 or at most 1 y in each structure is selected from N.

[0184] Preferably, said L2 is selected from a single bond or any one of the following structures,

[0185]

[0186]

[0187] said Rp, Rq, Rn is the same or different selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl;

[0188] said R 11 is the same or different selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy;

[0189] said g1 is selected from 0, 1, 2, 3, or 4; said g2 is selected from 0, 1, 2, 3, 4, 5, or 6; said g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said g5 is selected from 0, 1, 2, or 3; said g6 is selected from 0, 1, or 2; said g7 is selected from 0, 1, 2, 3, 4, or 5; said g8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said g9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said g 10 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; when there are two or more R 11 groups, two or more R 11 groups are the same or different from each other, or two adjacent R 11 groups are connected to each other to form a substituted or unsubstituted ring.

[0190] Preferably, said is selected from any one of the following structures,

[0191]

[0192]

[0193] said X is selected from O, S, or N(Rc);

[0194] said Rc is selected from any one of methyl, ethyl, isopropyl, tert-butyl, benzo- cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo- cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri- tert-butylsilyl, triphenylsilyl, deuterated phenyl, methylphenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, furanyl, thienyl, benzo-furanyl, benzo-thienyl, dibenzo-furanyl, dibenzo-thienyl, carbazolyl, fluorenyl, benzo-oxazolyl, benzo-thiazolyl;

[0195] R5is selected from any one of methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0196] R5may be substituted with one or more substituents selected from any one or combination of deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl group; when there are two or more substituents, the two or more substituents are the same or different from each other;

[0197] R7is selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0198] R7may be substituted with one or more substituents selected from any one of deuterium, cyano, halogen, trifluoromethyl;

[0199] n1is selected from 0, 1, 2, 3 or 4; n2is selected from 0, 1, 2 or 3; n3is selected from 0, 1 or 2; n4is selected from 0, 1, 2, 3, 4, 5 or 6; n5is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; n6is selected from 0, 1, 2, 3, 4 or 5; n7is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0200] Preferably, formula 2 is selected from any one of the following structures,

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226] The electron transport region comprises at least one of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one of the hole blocking layer, the electron injection layer, and the electron transport layer comprises a structure represented by Formula 2.

[0227] The electron transport region comprises at least one of a hole blocking layer and an electron transport layer, and at least one of the hole blocking layer and the electron transport layer comprises a structure represented by Formula 2.

[0228] The electron transport region comprises a hole blocking layer, and the hole blocking layer comprises a structure represented by Formula 2.

[0229] Preferably, the thickness of the electron transport layer is 5-80 nm, and preferably 10-50 nm.

[0230] Preferably, the thickness of the hole blocking layer is 1-100 nm, and preferably 5-45 nm.

[0231] The electron transport region can have a structure of a hole blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron injection layer, an electron transport layer and an electron injection layer, a hole blocking layer and an electron transport layer, or a hole blocking layer, an electron transport layer, and an electron injection layer, with reference to the light-emitting layer. Preferably, the electron transport region comprises a hole blocking layer, an electron transport layer, and an electron injection layer.

[0232] In the organic electroluminescent device of the present application, the hole blocking layer preferably uses a material having good hole blocking performance, and specific examples of the hole blocking layer material that can be used in the present application can include imidazole-based, triazole-based, phenanthroline derivatives, quinoline-based materials, such as 2,9-(dimethyl)-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)diphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 8-hydroxyquinoline-lithium (LiQ), and the like, but are not limited thereto. Preferably, the hole blocking layer is selected from a structure represented by Formula 2.

[0233] In the organic electroluminescent device according to the present application, the electron transport layer preferably uses a material having a strong electron-accepting ability and a low HOMO and LUMO energy level, and specific examples of the material that can be used in the electron transport layer according to the present application can include imidazole derivatives, triazole derivatives, phenanthroline derivatives, quinoline derivatives, and the like, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)diphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(diphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 8-hydroxyquinoline-lithium (LiQ), and the like, but are not limited thereto. Preferably, the electron transport layer is selected from the group consisting of the structures represented by Formula 2.

[0234] In the organic electroluminescent device according to the present application, the electron injection layer preferably uses a material having a small difference in potential barrier from the adjacent organic transport material, while having an effect of injecting electrons from the cathode, and specific examples of the material that can be used in the electron injection layer according to the present application can include alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF2), metal oxides (such as Al2O3, MoO3), and the like, but are not limited thereto.

[0235] Cathode

[0236] In the organic electroluminescent device according to the present application, the cathode preferably uses a low work function material capable of promoting the injection of electrons into the organic layer, and specific examples of the material that can be used in the cathode according to the present application can include metals such as aluminum, magnesium, silver, indium, tin, titanium, and the like, and alloys thereof; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, and the like, but are not limited thereto.

[0237] The organic electroluminescent device according to the present application can further include a capping layer, and the capping layer according to the present application preferably uses a material capable of improving light coupling, and specific examples of the material that can be used in the capping layer according to the present application can include arylamine derivatives, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, and the like, but are not limited thereto.

[0238] The organic electroluminescent device according to the present application can further include a substrate, and the substrate according to the present application can be preferably made of a material which does not change when electrodes and other functional layers are formed, and specific examples of the substrate material which can be used in the present application can include glass, quartz, plastic, a polymer film, silicon, etc., but are not limited thereto. The substrate can be retained in a light emitting device or an electronic device using the organic electroluminescent device according to the present application, or can not be retained in a final product but can only function as a support in a manufacturing process of the organic electroluminescent device.

[0239] However, the structure of the organic electroluminescent device according to the present application is not limited thereto. The organic electroluminescent device according to the present application can be selected and combined according to the requirements of device parameters and the characteristics of materials, and some organic layers can be added or omitted, and organic layers having the same function can be made into a stacked structure of two or more layers.

[0240] The light emitting type of the organic electroluminescent device according to the present application can be a top emission device or a bottom emission device, and the difference between the two is that the light emitting direction of the device is through the substrate or in a direction away from the substrate. For the bottom emission device, the light emitting direction of the device is through the substrate, and for the top emission device, the light emitting direction of the device is in a direction away from the substrate.

[0241] The structure of the organic electroluminescent device according to the present application can be a normal structure or an inverted structure, and the difference between the two is that the order of making the organic layers is different, and specifically, the normal structure is to form a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, a hole transport layer, a hole injection layer, and an anode in order on a substrate, and the inverted structure is to form an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode in order on a substrate.

[0242] The organic electroluminescent device according to the present application can use any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer printing method, an electro-spraying method, a slot coating method, and a dip coating method.

[0243] The organic electroluminescent device according to the present application can be widely used in the fields of panel display, lighting sources, flexible OLED, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lights, etc.

[0244] The present application is explained more in detail by the following examples, but it is not intended to limit the present application thereby. Based on this description, a person of ordinary skill in the art will be able to implement the present application and prepare other compounds and devices according to the present application within the entire scope disclosed without any creative effort.

[0245] The present application also provides a preparation method of the compound represented by Formula 1 or Formula 2, but the preparation method of the present application is not limited thereto. The core structure of the compound of Formula 1 or Formula 2 can be prepared by the following reaction route, the substituents can be bonded by methods known in the art, and the types and positions of the substituents or the number of the substituents can be changed according to techniques known in the art.

[0246] Preparation of Formula 1:

[0247]

[0248] Preparation of Formula 2:

[0249]

[0250] Xa is the same or different and is selected from I, Br, Cl;

[0251] Explanation of raw materials, reagents, and characterization equipment:

[0252] The present application does not have special limitations on the raw materials and reagents used in the following examples, which can be commercially available products or prepared by methods known to those skilled in the art. The raw materials and reagents used in the present application are reagent pure.

[0253] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the UK with chloroform as the solvent;

[0254] Elemental analysis uses a Vario EL cube organic elemental analyzer from Elementar, Germany, with a sample mass of 5-10 mg;

[0255] Synthesis Example 1: Preparation of Intermediate A-1-14

[0256]

[0257] Under nitrogen protection, a-1-14 (12.12 g, 100.00 mmol), b-1-14 (25.11 g, 100.00 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) were added to 500 ml of toluene, Pd(dppf)Cl2 (0.73 g, 1.00 mmol) was added with stirring, and the mixture was heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by reduced pressure distillation. Crystallization was performed by cooling, suction filtration was performed, and the obtained solid was recrystallized with ethyl acetate to obtain intermediate A-1-14 (23.89 g, 82%), with an HPLC purity of ≧99.89%. Mass spectrometry m / z: 291.1437 (theoretical value: 291.1423).

[0258] Synthesis Example 2: Preparation of intermediate A-1-116

[0259]

[0260] The a-1-14, b-1-14 in Synthesis Example 1 were replaced by equal molar amount of a-1-116, b-1-116, and other steps were the same to obtain intermediate A-1-116 (33.83 g) with solid purity of 99.85% detected by HPLC. Mass spectrum m / z: 417.2463 (theoretical value: 417.2457).

[0261] Synthesis Example 3: Preparation of intermediate A-1-313

[0262]

[0263] The a-1-14, b-1-14 in Synthesis Example 1 were replaced by equal molar amount of a-1-116, b-1-313, and other steps were the same to obtain intermediate A-1-313 (22.54 g) with solid purity of 99.83% detected by HPLC. Mass spectrum m / z: 285.1161 (theoretical value: 285.1154).

[0264] Synthesis Example 4: Preparation of intermediate A-1-354

[0265]

[0266] The a-1-14, b-1-14 in Synthesis Example 1 were replaced by equal molar amount of a-1-354, b-354, and other steps were the same to obtain intermediate A-1-354 (30.20 g) with solid purity of 99.82% detected by HPLC. Mass spectrum m / z: 377.1248 (theoretical value: 377.1238).

[0267] Synthesis Example 5: Preparation of intermediate A-1-638

[0268]

[0269] The a-1-14, b-1-14 in Synthesis Example 1 were replaced by equal molar amount of a-1-638, b-638, and other steps were the same to obtain intermediate A-1-638 (29.99 g) with solid purity of 99.74% detected by HPLC. Mass spectrum m / z: 384.1635 (theoretical value: 384.1626).

[0270] Synthesis Example 6: Preparation of compound 1-14

[0271]

[0272] Under nitrogen protection, intermediate A-1-14 (14.57 g, 50.00 mmol), raw material B-1-14 (7.80 g, 25.00 mmol), sodium tert-butoxide (7.21 g, 75.00 mmol) were added into 180 ml of toluene, and Pd2(dba)3 (0.23 g, 0.25 mmol), BINAP (0.31 g, 0.50 mmol) were added under stirring, and the mixture solution was heated to reflux for 4.5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. Crystallization was performed by cooling, suction filtration was performed, and the obtained solid was recrystallized with toluene to obtain compound 1-14 (14.48 g, yield 79%), HPLC purity ≧ 99.95%. Mass spectrum m / z: 732.3309 (theoretical value: 732.3316). Theoretical elemental content (%) C 52 H 42 F2N2: C, 85.22; H, 5.78; N, 3.82. Measured elemental content (%): C, 85.21; H, 5.74; N, 3.87.

[0273]

[0274] According to the preparation method of synthesis example 6, replace the equal moles of A-1-14 with equal moles of A-1-23 to obtain compound 1-23 (14.12 g), HPLC purity ≧ 99.90%. Mass spectrum m / z: 752.4137 (theoretical value: 752.4130). Theoretical elemental content (%) C 56 H 52 N2: C, 89.32; H, 6.96; N, 3.72. Measured elemental content (%): C, 89.36; H, 6.94; N, 3.70.

[0275] Synthesis example 8: preparation of compound 1-37

[0276]

[0277] According to the preparation method of synthesis example 6, replace the equal moles of A-1-14 with equal moles of A-1-37 to obtain compound 1-37 (13.16 g), HPLC purity ≧ 99.92%. Mass spectrum m / z: 720.3512 (theoretical value: 720.3504). Theoretical elemental content (%) C 54 H 44N2: C, 89.96; H, 6.15; N, 3.89. Found: C, 89.97; H, 6.16; N, 3.87.

[0278] Synthesis Example 9: Preparation of compound 1-44

[0279]

[0280] According to the preparation method of Synthesis Example 6, replace equal moles of A-1-14 with equal moles of A-1-44 to obtain compound 1-44 (14.84 g) with HPLC purity of ≧99.95%. Mass spectrum m / z: 780.4450 (theoretical value: 780.4443). Theoretical elemental content (%) C 58 H 56 N2: C, 89.96; H, 6.15; N, 3.89. Found: C, 89.97; H, 6.16; N, 3.87.

[0281] Synthesis Example 10: Preparation of compound 1-92

[0282]

[0283] Preparation of intermediate C-1-92:

[0284] Under nitrogen protection, intermediate A-1-92 (16.07 g, 50.00 mmol), B-1-92 (13.38 g, 50.00 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol) were added into 275 ml of toluene, Pd(OAc)2(0.14 g, 0.60 mmol), P(t-Bu)3(2.40 mL of 0.5M toluene solution, 1.20 mmol) were added with stirring, and the mixture solution of the above reactants was heated to reflux for 4 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by reduced pressure distillation, and then crystallized by cooling. The obtained solid was recrystallized with toluene / ethanol = 6 / 2 to obtain intermediate C-1-92 (21.59 g, 85%) with HPLC purity of ≧99.90%. Mass spectrum m / z: 507.1769 (theoretical value: 507.1754).

[0285] Preparation of compound 1-92:

[0286] Under nitrogen protection, intermediate C-1-92 (12.70 g, 25.00 mmol), D-1-92 (6.58 g, 25.00 mmol), sodium tert-butoxide (4.81 g, 50.00 mmol) were added into 180 ml of toluene, Pd2(dba)3 (0.46 g, 0.50 mmol) and BINAP (0.62 g, 1.00 mmol) were added under stirring, the mixture was heated to reflux for 5.5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, separated, the organic layer was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated by distillation under reduced pressure, crystallized by cooling, filtered, and the obtained solid was recrystallized with toluene to obtain compound 1-92 (14.33 g, yield 78%), HPLC purity≧99.91%. Mass spectrum m / z: 734.3652 (theoretical value: 734.3661). Theoretical elemental content (%) C 55 H 46 N2: C, 89.88; H, 6.31; N, 3.81. Actual elemental content (%) : C, 89.85; H, 6.32; N, 3.83.

[0287] Synthesis Example 11: Preparation of compound 1-94

[0288]

[0289] According to the preparation method of synthesis example 6, replace equal moles of A-1-14, B-1-14 with equal moles of A-1-94, B-1-94 to obtain compound 1-94 (18.12 g), HPLC purity≧99.93%. Mass spectrum m / z: 928.3662 (theoretical value: 928.3669). Theoretical elemental content (%) C 66 H 52 N2Si2: C, 85.30; H, 5.64; N, 3.01. Actual elemental content (%) : C, 85.33; H, 5.60; N, 3.02.

[0290] Synthesis Example 12: Preparation of compound 1-110

[0291]

[0292] According to the preparation method of synthesis example 10, replace equal moles of A-1-92, D-1-92 with equal moles of A-1-110, D-1-110 to obtain compound 1-110 (14.08 g), HPLC purity≧99.90%. Mass spectrum m / z: 712.3282 (theoretical value: 712.3274). Theoretical elemental content (%) C 51 H 44 N2Si C, 85.91 ; H, 6.22; N, 3.93. Found (%): C, 85.97; H, 6.19; N, 3.90.

[0293] Synthesis Example 13: Preparation of compound 1-116

[0294]

[0295] According to the preparation method of synthesis example 6, replace equal moles of A-1-14 with equal moles of A-1-116 to obtain compound 1-116 (18.97 g) with HPLC purity ≧ 99.94%. Mass spectrum m / z: 984.5390 (theoretical value: 984.5383). Theoretical elemental content (%) C 74 H 68 N2: C, 90.20; H, 6.96; N, 2.84. Found (%): C, 90.26; H, 6.93; N, 2.81.

[0296] Synthesis Example 14: Preparation of compound 1-209

[0297]

[0298] According to the preparation method of synthesis example 6, replace equal moles of A-1-14 with equal moles of A-1-209, and replace equal moles of B-1-14 with equal moles of B-1-209 to obtain compound 1-209 (17.35 g) with HPLC purity ≧ 99.91%. Mass spectrum m / z: 924.4452 (theoretical value: 924.4443). Theoretical elemental content (%) C 70 H 56 N2: C, 90.87; H, 6.10; N, 3.03. Found (%): C, 90.81; H, 6.13; N, 3.06.

[0299] Synthesis Example 15: Preparation of compound 1-239

[0300]

[0301] According to the preparation method of synthesis example 6, replace equal moles of A-1-14, B-1-14 with equal moles of A-1-239, B-1-239 to obtain compound 1-239 (12.97 g) with HPLC purity ≧ 99.93%. Mass spectrum m / z: 682.2994 (theoretical value: 682.2984). Theoretical elemental content (%) C 50 H 38N2O: C, 87.95; H, 5.61; N, 4.10. Found: C, 87.90; H, 5.63; N, 4.13.

[0302] Synthesis Example 16: Preparation of compound 1-313

[0303]

[0304] According to the preparation method of synthesis example 10, replace equal moles of A-1-92, D-1-92 with equal moles of A-1-313, D-1-110 to obtain compound 1-313 (12.10 g) with HPLC purity ≧ 99.96%. Mass spectrum m / z: 604.2525 (theoretical value: 604.2515). Theoretical elemental content (%) C 44 H 32 N2O: C, 87.39; H, 5.33; N, 4.63. Found: C, 87.44; H, 5.30; N, 4.61.

[0305] Synthesis Example 17: Preparation of compound 1-354

[0306]

[0307] According to the preparation method of synthesis example 6, replace equal moles of A-1-14 with equal moles of A-1-354 to obtain compound 1-354 (16.75 g) with HPLC purity ≧ 99.95%. Mass spectrum m / z: 904.2954 (theoretical value: 904.2946). Theoretical elemental content (%) C 64 H 44 N2S2: C, 84.92; H, 4.90; N, 3.09. Found: C, 84.95; H, 4.89; N, 3.07.

[0308] Synthesis Example 18: Preparation of compound 1-392

[0309]

[0310] Preparation of compound 1-392:

[0311] According to the preparation method of synthesis example 10, replace equal moles of A-1-92, D-1-92 with equal moles of A-1-392, D-1-392 to obtain compound 1-392 (12.42 g) with HPLC purity ≧ 99.90%. Mass spectrum m / z: 628.2890 (theoretical value: 628.2878). Theoretical elemental content (%) C 47 H 36N2: C, 89.77; H, 5.77; N, 4.46. Found (mass %): C, 89.84; H, 5.74; N, 4.42.

[0312] Synthesis Example 19: Preparation of compound 1-453

[0313]

[0314] According to the preparation method of synthesis example 6, replace equal moles of A-1-14, B-1-14 with equal moles of A-1-453, B-1-453 to obtain compound 1-453 (13.26 g) with HPLC purity ≧ 99.91%. Mass spectrum m / z: 688.2889 (theoretical value: 688.2878). Theoretical elemental content (%) C 52 H 36 N2: C, 90.67; H, 5.27; N, 4.07. Found elemental content (%) C, 90.68; H, 5.28; N, 4.05.

[0315] Synthesis Example 20: Preparation of compound 1-494

[0316]

[0317] According to the preparation method of synthesis example 6, replace equal moles of A-1-14, B-1-14 with equal moles of A-1-494, B-1-209 to obtain compound 1-494 (14.77 g) with HPLC purity ≧ 99.95%. Mass spectrum m / z: 808.3679 (theoretical value: 808.3669). Theoretical elemental content (%) C 56 H 52 N2Si2: C, 83.12; H, 6.48; N, 3.46. Found elemental content (%) C, 83.15; H, 6.46; N, 3.45.

[0318] Synthesis Example 21: Preparation of compound 1-638

[0319]

[0320] According to the preparation method of synthesis example 6, replace equal moles of A-1-14 with equal moles of A-1-638 to obtain compound 1-638 (16.77 g) with HPLC purity ≧ 99.93%. Mass spectrum m / z: 918.3729 (theoretical value: 918.3722). Theoretical elemental content (%) C 68 H 46N4: C, 88.86; H, 5.04; N, 6.10. Found (mass %): C, 88.90; H, 5.02; N, 6.08.

[0321] Synthesis Example 22: Preparation of compound 1-675

[0322]

[0323] According to the preparation method of synthesis example 10, replace equal moles of A-1-92, D-1-92 with equal moles of A-1-675, D-1-675 to obtain compound 1-675 (12.63 g) with HPLC purity ≧ 99.96%. Mass spectrum m / z: 664.2870 (theoretical value: 664.2878). Theoretical elemental content (%) C 50 H 36 N2: C, 90.33; H, 5.46; N, 4.21 Found (mass %): C, 90.38; H, 5.44; N, 4.18.

[0324] Synthesis Example 23: Preparation of compound 1-707

[0325]

[0326] According to the preparation method of synthesis example 10, replace equal moles of A-1-92, D-1-92 with equal moles of A-1-707, D-1-675 to obtain compound 1-707 (14.34 g) with HPLC purity ≧ 99.94%. Mass spectrum m / z: 744.2591 (theoretical value: 744.2599). Theoretical elemental content (%) C 54 H 36 N2S: C, 87.06; H, 4.87; N, 3.76 Found (mass %): C, 87.11; H, 4.85; N, 3.73.

[0327] Synthesis Example 24: Preparation of intermediate a-2-116

[0328]

[0329] d-2-116 (71.80 g, 200.00 mmol) was dissolved in 380.00 ml of anhydrous tetrahydrofuran, the temperature of the solution was maintained at -78 °C under nitrogen, n-butyllithium hexane solution (75.00 ml, 2.5 M) was slowly added dropwise, after the addition was completed, it was stirred for 3 hours, then d-2-116 (57.68 g, 200.00 mmol) was dissolved in 250.00 ml of tetrahydrofuran, slowly added dropwise, the reaction solution was maintained at -78 °C, stirred for 2.5 hours, after warming to room temperature, it was stirred overnight. The solvent was removed under reduced pressure, the residue was dissolved in glacial acetic acid (300.00 ml), concentrated hydrochloric acid solution (30.00 ml, 31%) was added, the mixture was reacted under reflux for 7.5 hours and stirred at room temperature overnight. After the reaction was completed, water was added, extracted with dichloromethane, the organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, recrystallized with isopropyl alcohol to obtain intermediate a-2-116 (68.47 g, yield 68%), HPLC purity ≧ 99.89%. Mass spectrum m / z: 502.1293 (theoretical value: 502.1296).

[0330] Synthesis Example 25: Preparation of intermediate a-2-131

[0331]

[0332] According to the preparation method of synthesis example 24, d-2-116 in synthesis example 24 was replaced with an equimolar amount of d-2-131, and other steps were the same to obtain intermediate a-2-131 (61.52 g), the solid purity was 99.91% detected by HPLC. Mass spectrum m / z: 438.0991 (theoretical value: 438.0983). Synthesis Example 26: Preparation of intermediate a-2-172

[0333]

[0334] According to the preparation method of synthesis example 24, d-2-116 and e-2-116 in synthesis example 24 were replaced with an equimolar amount of d-2-172 and e-2-172, and other steps were the same to obtain intermediate a-2-172 (56.77 g), the solid purity was 99.93% detected by HPLC. Mass spectrum m / z: 410.0679 (theoretical value: 410.0670).

[0335] Synthesis Example 27: Preparation of intermediate a-2-242

[0336]

[0337] Following the procedure of Synthesis Example 24, replace d-2-116 in Synthesis Example 24 with an equal molar amount of d-2-242, and follow the same procedure to obtain intermediate a-2-242 (62.10 g) with a solid purity of 99.95% as determined by HPLC. Mass spectrum m / z: 424.0819 (theoretical value: 424.0827). Synthesis Example 28: Preparation of intermediate a-2-298

[0338]

[0339] Following the procedure of Synthesis Example 24, replace d-2-116 in Synthesis Example 24 with an equal molar amount of d-2-298, and follow the same procedure to obtain intermediate a-2-298 (71.21 g) with a solid purity of 99.94% as determined by HPLC. Mass spectrum m / z: 500.1149 (theoretical value: 500.1140). Synthesis Example 29: Preparation of intermediate a-2-331

[0340]

[0341] Following the procedure of Synthesis Example 24, replace d-2-116 in Synthesis Example 24 with an equal molar amount of d-2-331, and follow the same procedure to obtain intermediate a-2-331 (78.23 g) with a solid purity of 99.95% as determined by HPLC. Mass spectrum m / z: 500.1148 (theoretical value: 500.1140). Synthesis Example 30: Preparation of intermediate a-2-503

[0342]

[0343] Following the procedure of Synthesis Example 24, replace d-2-116, e-2-116 in Synthesis Example 24 with an equal molar amount of d-2-172, e-2-503, and follow the same procedure to obtain intermediate a-2-503 (61.25 g) with a solid purity of 99.93% as determined by HPLC. Mass spectrum m / z: 424.0835 (theoretical value: 424.0827).

[0344] Synthesis Example 31: Preparation of intermediate a-2-953

[0345]

[0346] According to the preparation method of synthetic example 24, d-2-116 in synthetic example 24 was replaced by an equal amount of d-2-953, and other steps were the same, to obtain intermediate a-2-953 (77.31 g), with a solid purity of 99.95% detected by HPLC. Mass spectrum m / z: 528.1462 (theoretical value: 528.1453).

[0347]

[0348] According to the preparation method of synthetic example 24, d-2-116, e-2-116 in synthetic example 24 was replaced by an equal amount of d-2-242, e-2-1017, and other steps were the same, to obtain intermediate a-2-1017 (65.66 g), with a solid purity of 99.92% detected by HPLC. Mass spectrum m / z: 425.0771 (theoretical value: 425.0779).

[0349] Synthetic example 33: preparation of compound 2-51

[0350]

[0351] Preparation of intermediate A-2-51: under nitrogen protection, a-2-51 (52.39 g, 150.00 mmol), bis(pinacolato)diboron (38.09 g, 150.00 mmol), K2CO3 (41.46 g, 300.00 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), 900 mL dimethylformamide were added to a reaction bottle, and the reaction was stirred under reflux conditions for 6.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, water was added, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation, then recrystallized with toluene / ethanol=10:3 to obtain intermediate A-2-51 (46.37 g, yield 78%), with a purity of ≧99.91% detected by HPLC. Mass spectrum m / z: 396.2274 (theoretical value: 396.2261).

[0352] Preparation of Intermediate B-2-51 : To a reaction flask was added A-2-51 (39.62 g, 100.00 mmol), b-2-51 (26.76 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), 750 mL of toluene / ethanol / water (3:1:1), stirred under reflux conditions for 5 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, suction filtered, rinsed with ethanol, then the resulting solid was recrystallized with toluene to obtain Intermediate B-2-51 (36.56 g, yield 80%), HPLC purity > 99.93%. Mass spectrum m / z: 456.1639 (theoretical value: 456.1645).

[0353] Preparation of Intermediate C-2-51 : To a reaction flask was added B-2-51 (29.71 g, 65.00 mmol), bis(pinacolato)diboron (16.51 g, 65.00 mmol), KOAc (10.80 g, 110.00 mmol), Pd(dppf)Cl2 (0.48 g, 0.65 mmol), 650 mL of 1,4-dioxane, stirred under reflux conditions for 5 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, water was added thereto, then extracted with ethyl acetate, the organic layer was dried with anhydrous magnesium sulfate, rotary evaporation was performed to remove the solvent, then recrystallized with toluene to obtain Intermediate C-2-51 (29.24 g, yield 82%), HPLC purity > 99.85%. Mass spectrum m / z: 548.2891 (theoretical value: 548.2887).

[0354] Preparation of Compound 2-51 : To a reaction flask was added C-2-51 (21.94 g, 40.00 mmol), c-2-51 (7.92 g, 40.00 mmol), K2CO3 (8.98 g, 65.00 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), P(t-Bu)3 (1.40 mL of 0.50 M toluene solution, 0.70 mmol), 300 mL of tetrahydrofuran, stirred under reflux conditions for 6 hours, after the reaction was completed, the reaction mixture was cooled to room temperature, suction filtered to obtain a filter cake, rinsed with a small amount of toluene, then the resulting filter cake was recrystallized with toluene to obtain Compound 2-51 (17.05 g, yield 79%), HPLC purity > 99.97%. Mass spectrum m / z: 539.2263 (theoretical value: 539.2249). Theoretical elemental content (%) 40 H 29NO: C, 89.02; H, 5.42; N, 2.60. Found (%): C, 89.07; H, 5.43; N, 2.64.

[0355] Synthesis Example 34: Preparation of compound 2-64

[0356]

[0357] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51 with equal moles of a-2-64, b-2-64 respectively, to obtain compound 2-64 (18.21 g), HPLC purity ≧ 99.98%. Mass spectrum m / z: 583.2343 (theoretical value: 583.2331). Theoretical elemental content (%) C 41 H 33 NO: C, 89.02; H, 5.42; N, 2.60. Found (%): C, 89.07; H, 5.43; N, 2.64.

[0358] Synthesis Example 35: Preparation of compound 2-75

[0359]

[0360] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51 with equal moles of a-2-75, b-2-75 respectively, to obtain compound 2-75 (14.72 g), HPLC purity ≧ 99.96%. Mass spectrum m / z: 592.2085 (theoretical value: 592.2093). Theoretical elemental content (%) C 39 H 27 NO: C, 89.02; H, 5.42; N, 2.60. Found (%): C, 89.07; H, 5.43; N, 2.64.

[0361] Synthesis Example 36: Preparation of compound 2-83

[0362]

[0363] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51 with equal moles of a-2-83, b-2-64 respectively, to obtain compound 2-83 (17.27 g), HPLC purity ≧ 99.93%. Mass spectrum m / z: 539.2240 (theoretical value: 539.2249). Theoretical elemental content (%) C 40 H 29Calculated (%) C, 89.02; H, 5.42; N, 2.60. Actual elemental content (%) C, 89.05; H, 5.44; N, 2.55.

[0364] Synthesis Example 37: Preparation of compound 2-116

[0365]

[0366] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51, c-2-51 with equal moles of a-2-116, b-2-64, c-2-131 respectively, to obtain compound 2-131 (17.13g), HPLC purity≧99.92%. Mass spectrum m / z: 629.2727 (theoretical value: 629.2719). Theoretical elemental content (%) C 46 H 35 Calculated (%) C, 89.43; H, 5.71; N, 2.27. Actual elemental content (%) C, 89.44; H, 5.75; N, 2.22.

[0367] Synthesis Example 38: Preparation of compound 2-131

[0368]

[0369] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51, c-2-51 with equal moles of a-2-116, b-2-64, c-2-131 respectively, to obtain compound 2-131 (17.13g), HPLC purity≧99.92%. Mass spectrum m / z: 629.2727 (theoretical value: 629.2719). Theoretical elemental content (%) C 47 H 35 Calculated (%) C, 89.63; H, 5.60; N, 2.22. Actual elemental content (%) C, 89.65; H, 5.63; N, 2.17.

[0370] Synthesis Example 39: Preparation of compound 2-140

[0371]

[0372] According to the preparation method of synthesis example 33, replace equal moles of a-2-51, b-2-51, c-2-51 with equal moles of a-2-116, b-2-64, c-2-131 respectively, to obtain compound 2-131 (17.13g), HPLC purity≧99.92%. Mass spectrum m / z: 629.2727 (theoretical value: 629.2719). Theoretical elemental content (%) C 56 H 41NO: C, 90.41 ; H, 5.56; N, 1.88. Found (%): C, 90.44; H, 5.55; N, 1.90.

[0373] Synthesis Example 40: Preparation of compound 2-172

[0374]

[0375] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-172 to obtain compound 2-172 (18.29 g) with HPLC purity ≧ 99.92%. Mass spectrum m / z: 601.2415 (theoretical value: 601.2406). Theoretical elemental content (%) C 45 H 31 NO: C, 89.82; H, 5.19; N, 2.33. Found (%): C, 89.83; H, 5.22; N, 2.30.

[0376] Synthesis Example 41: Preparation of compound 2-174

[0377]

[0378] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-174 respectively to obtain compound 2-174 (16.87 g) with HPLC purity ≧ 99.97%. Mass spectrum m / z: 585.2085 (theoretical value: 585.2093). Theoretical elemental content (%) C 44 H 27 NO: C, 90.23; H, 4.65; N, 2.39. Found (%): C, 90.25; H, 4.66; N, 2.36.

[0379] Synthesis Example 42: Preparation of compound 2-197

[0380]

[0381] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-197 to obtain compound 2-197 (21.42 g) with HPLC purity ≧ 99.94%. Mass spectrum m / z: 677.2726 (theoretical value: 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Found (%): C, 90.41 ; H, 5.22; N, 2.01.

[0382] Synthetic Example 43: Preparation of Compound 2-236

[0383]

[0384] According to the preparation method of Synthesis Example 33, equimolar amounts of a-2-51 were replaced with equimolar amounts of a-2-75 to obtain compound 2-236 (16.37 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 601.2418 (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, 89.80; H, 5.22; N, 2.32.

[0385] Synthesis Example 44: Preparation of Compound 2-242

[0386]

[0387] According to the preparation method in Synthesis Example 33, equimolar amounts of a-2-51 were replaced with equimolar amounts of a-2-242 to obtain compound 2-242 (17.73 g), with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 615.2577 (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, 5.42; N, 2.23.

[0388] Synthetic Example 45: Preparation of Compounds 2-245

[0389]

[0390] According to the preparation method in Synthesis Example 33, equimolar amounts of a-2-51 were replaced with equimolar amounts of a-2-245 to obtain compound 2-245 (18.23 g), with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 615.2571 (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, 5.42; N, 2.23.

[0391] Synthesis Example 46: Preparation of Compound 2-265

[0392]

[0393] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-140 to obtain compound 2-265 (19.57 g) with HPLC purity > 99.97%. Mass spectrum m / z: 643.2864 (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, 89.53; H, 5.82; N, 2.17.

[0394] Synthesis Example 47: Preparation of compound 2-280

[0395]

[0396] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-280 to obtain compound 2-280 (19.27 g) with HPLC purity > 99.94%. Mass spectrum m / z: 659.2655 (theoretical value: 659.2644). Theoretical elemental content (%) C 47 H 37 NOSi: C, 85.55; H, 5.65; N, 2.12. Measured elemental content (%) : C, 85.59; H, 5.67; N, 2.06.

[0397] Synthesis Example 48: Preparation of compound 2-289

[0398]

[0399] According to the preparation method of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-289 to obtain compound 2-289 (20.79 g) with HPLC purity > 99.91%. Mass spectrum m / z: 721.3361 (theoretical value: 721.3345). Theoretical elemental content (%) C 54 H 43 NO: C, 89.84; H, 6.00; N, 1.94. Measured elemental content (%) : C, 89.80; H, 6.02; N, 1.96.

[0400] Synthesis Example 49: Preparation of compound 2-298

[0401]

[0402] Following the procedure of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-300 to obtain compound 2-300 (19.79 g) with HPLC purity > 99.91 %. Mass spectrum m / z: 677.2712 (calcd 677.2719). Theoretical elemental content (%) C 52 H 37 NO: C, 90.37; H, 5.20; N, 2.07. Found elemental content (%): C, 90.39; H, 5.22; N, 2.03.

[0403] Synthesis Example 50: Preparation of compound 2-300

[0404]

[0405] Following the procedure of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-300 to obtain compound 2-300 (19.79 g) with HPLC purity > 99.91 %. Mass spectrum m / z: 677.2712 (calcd 677.2719). Theoretical elemental content (%) C 51 H 35 NO: C, 90.37; H, 5.20; N, 2.07. Found elemental content (%): C, 90.39; H, 5.22; N, 2.03.

[0406] Synthesis Example 51: Preparation of compound 2-331

[0407]

[0408] Following the procedure of Synthesis Example 33, replace equal moles of a-2-51 with equal moles of a-2-331 to obtain compound 2-331 (20.48 g) with HPLC purity > 99.95 %. Mass spectrum m / z: 691.2862 (calcd 691.2875). Theoretical elemental content (%) C 52 H 37 NO: C, 90.27; H, 5.39; N, 2.02. Found elemental content (%): C, 90.28; H, 5.40; N, 2.00.

[0409] Synthesis Example 52: Preparation of compound 2-405

[0410]

[0411] Following the procedure of the preparation of the synthesis example 33, replacing equal moles of a-2-51, b-2-51 with equal moles of a-2-75, b-2-523, respectively, compound 2-523 (19.40 g) was obtained with HPLC purity > 99.92%. Mass spectrum m / z: 629.2341 (calc. 629.2355). Theoretical elemental content (%) C 49 H 33 NO: C, 90.29; H, 5.10; N, 2.15. Found: C, 90.30; H, 5.12; N, 2.12.

[0412] Synthesis example 53: Preparation of compound 2-470

[0413]

[0414] Following the procedure of the preparation of the synthesis example 33, replacing equal moles of a-2-51, b-2-51 with equal moles of a-2-75, b-2-470, respectively, compound 2-470 (19.05 g) was obtained with HPLC purity > 99.93%. Mass spectrum m / z: 602.2345 (calc. 602.2358). Theoretical elemental content (%) C 44 H 30 N2O: C, 87.68; H, 5.02; N, 4.65. Found: C, 87.66; H, 5.03; N, 4.66.

[0415] Synthesis example 54: Preparation of compound 2-503

[0416]

[0417] Following the procedure of the preparation of the synthesis example 33, replacing equal moles of a-2-51, b-2-51 with equal moles of a-2-503, b-2-503, respectively, compound 2-503 (19.40 g) was obtained with HPLC purity > 99.92%. Mass spectrum m / z: 629.2341 (calc. 629.2355). Theoretical elemental content (%) C 46 H 31 NO2: C, 87.73; H, 4.96; N, 2.22. Found: C, 87.72; H, 4.98; N, 2.21.

[0418] Synthesis example 55: Preparation of compound 2-523

[0419]

[0420] According to the preparation method in Synthesis Example 33, equimolar amounts of a-2-51 and b-2-51 were replaced with equimolar amounts of a-2-523 and b-2-64, respectively, to obtain compound 2-523 (17.16 g), with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 595.2888 (theoretical value: 595.2875). Theoretical elemental content (%) C 44 H 37 NO: C, 88.70; H, 6.26; N, 2.35. Measured elemental content (%): C, 88.68; H, 6.27; N, 2.36.

[0421] Synthetic Example 56: Preparation of Compound 2-833

[0422]

[0423] According to the preparation method of Synthesis Example 33, equimolar amounts of a-2-51 and c-2-51 were replaced with equimolar amounts of a-2-140 and c-2-833, respectively, to obtain compound 2-833 (21.00 g), with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 718.3332 (theoretical value: 718.3348). Theoretical elemental content (%) C 54 H 42 N2: C, 90.21; H, 5.89; N, 3.90. Measured elemental content (%): C, 90.24; H, 5.90; N, 3.86.

[0424] Synthesis Example 57: Preparation of Compound 2-953

[0425]

[0426] According to the preparation method in Synthesis Example 33, equimolar amounts of a-2-51, b-2-51, and c-2-51 were replaced with equimolar amounts of a-2-953, b-2-64, and c-2-953, respectively, to obtain compound 2-953 (17.69 g) with an HPLC purity ≥ 99.91%. Mass spectrometry m / z: 659.2634 (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, 87.39; H, 5.67; N, 2.08.

[0427] Synthesis Example 58: Preparation of Compound 2-987

[0428]

[0429] According to the preparation method of Synthetic Example 33, replace equal moles of a-2-51, b-2-51, c-2-51 with equal moles of a-2-75, b-2-987, c-2-953, respectively, to obtain compound 2-987 (17.91 g) with HPLC purity > 99.95%. Mass spectrum m / z: 621.2440 (theoretical value: 621.2428). Theoretical elemental content (%) C 45 H 27 D4NS: C, 86.92; H, 5.67; N, 2.25. Found elemental content (%) C, 86.93; H, 5.69; N, 2.22. Synthetic Example 59: Preparation of compound 2-994

[0430]

[0431] According to the preparation method of Synthetic Example 33, replace equal moles of a-2-51, c-2-51 with equal moles of a-2-75, c-2-953, respectively, to obtain compound 2-994 (17.30 g) with HPLC purity > 99.97%. Mass spectrum m / z: 617.2160 (theoretical value: 617.2177). Theoretical elemental content (%) C 45 H 31 NS: C, 87.49; H, 5.06; N, 2.27. Found elemental content (%) C, 87.50; H, 5.08; N, 2.24.

[0432] Synthetic Example 60: Preparation of compound 2-1017

[0433]

[0434] According to the preparation method of Synthetic Example 33, replace equal moles of a-2-51, c-2-51 with equal moles of a-2-1017, c-2-953, respectively, to obtain compound 2-1017 (16.69 g) with HPLC purity > 99.96%. Mass spectrum m / z: 632.2297 (theoretical value: 632.2286). Theoretical elemental content (%) C 45 H 32 N2S: C, 85.41; H, 5.10; N, 4.43. Found elemental content (%) C, 85.43; H, 5.11; N, 4.40.

[0435] Synthetic Example 61: Preparation of compound 2-1027

[0436]

[0437] According to the preparation method of Synthetic Example 33, replace equal moles of a-2-51, c-2-51 with equal moles of a-2-245, c-2-1027, respectively, to obtain compound 2-1027 (20.00 g) with HPLC purity > 99.93%. Mass spectrum m / z: 632.2298 (theoretical value: 632.2286). Theoretical elemental content (%) C 45 H 32 N2S: C, 85.41; H, 5.10; N, 4.43. Actual elemental content (%) C, 85.42; H, 5.11; N, 4.41.

[0438] Synthetic Example 62: Preparation of compound 2-1067

[0439]

[0440] According to the preparation method of Synthetic Example 33, replace equal moles of a-2-51, b-2-51, c-2-51 with equal moles of a-2-172, b-2-1067, c-2-953, respectively, to obtain compound 2-1067 (17.11 g) with HPLC purity > 99.94%. Mass spectrum m / z: 619.2070 (theoretical value: 619.2082). Theoretical elemental content (%) C 43 H 29 N3S: C, 83.33; H, 4.72; N, 6.78. Actual elemental content (%) C, 83.32; H, 4.70; N, 6.81.

[0441] [Device Example 1-25]

[0442] The ITO glass substrate was cleaned with 5% glass cleaning solution for 2 times, 20 minutes each time, and then cleaned with deionized water for 2 times, 10 minutes each time. The substrate was cleaned with acetone and isopropyl alcohol for 20 minutes each time by ultrasonic cleaning, and then dried at 120°C. A P-1:HI = 97:3 (mass ratio) was vacuum evaporated on the ITO substrate as a hole injection layer with a thickness of 10 nm; a compound 1-1 of the application was vacuum evaporated on the hole injection layer as a hole transport layer with a thickness of 120 nm; a GH-1:GH2:GD = 47:47:6 (mass ratio) was vacuum evaporated on the hole transport layer as a light-emitting layer with a thickness of 30 nm; a compound 2-987 of the application was vacuum evaporated on the light-emitting layer as a hole blocking layer with a thickness of 15 nm; an ET was vacuum evaporated on the hole blocking layer as an electron transport layer with a thickness of 30 nm; a LiF was vacuum evaporated on the electron transport layer as an electron injection layer with a thickness of 1 nm; and an Al was vacuum evaporated on the electron injection layer as a cathode with a thickness of 70 nm.

[0443]

[0444] Device Examples 2-25: The organic electroluminescent device was produced by using the compound 1-5, 1-14, 1-23, 1-25, 1-37, 1-59, 1-69, 1-71, 1-94, 1-116, 1-121, 1-185, 1-209, 1-220, 1-243, 1-263, 1-313, 1-368, 1-418, 1-494, 1-618, 1-638, 1-707, 1-822 of the present application instead of the compound 1-1 of the present application as the hole transport layer material in Device Example 1, using the compound 2-236, 2-405, 2-289, 2-265, 2-280, 2-64, 2-242, 2-116, 2-331, 2-174, 2-994, 2-75, 2-83, 2-953, 2-1027, 2-197, 2-172, 2-503, 2-51, 2-523, 2-131, 2-833, 2-140, 2-1067 instead of the compound 2-987 of the present application as the hole blocking layer material in Device Example 1, and applying the same procedures as in Device Example 1 except for the above.

[0445] Comparative Examples 1-7: The organic electroluminescent device was produced by using TAPC instead of the compound 1-1 of the present application as the hole transport layer material in Device Example 1, using the compound 2-83, 2-116, 2-140, 2-197, 2-236, 2-265, 2-503 instead of the compound 2-987 of the present application as the hole blocking layer material in Device Example 1, and applying the same procedures as in Device Example 1 except for the above.

[0446] Comparative Example 8: The ITO glass substrate was cleaned by using 5% glass cleaning solution for 2 times, 20 minutes each time, and then cleaned by using deionized water for 2 times, 10 minutes each time. The substrate was cleaned by using acetone and isopropyl alcohol for 20 minutes each time, and then dried at 120°C. The compound 1-5 of the present application was vacuum deposited on the ITO substrate as the hole transport layer, and the thickness of the layer was 120 nm. GH-1: GH2: GD = 47:47:6 (mass ratio) was vacuum deposited on the hole transport layer as the light-emitting layer, and the thickness of the layer was 30 nm. ET was vacuum deposited on the light-emitting layer as the electron transport layer, and the thickness of the layer was 45 nm. LiF was vacuum deposited on the electron transport layer as the electron injection layer, and the thickness of the layer was 1 nm. Al was vacuum deposited on the electron injection layer as the cathode, and the thickness of the layer was 70 nm.

[0447] Comparative Examples 9 to 14: The organic electroluminescent device was prepared by using the compounds 2-25, 2-71, 2-209, 2-263, 2-368, 2-707 of the present application instead of the compound 2-5 of the present application as the hole transport layer material in Comparative Example 8, and by applying the same procedures as in Comparative Example 8.

[0448] The test software, computer, K2400 digital source meter of Keithley Company of USA and PR788 spectral scanning luminance meter of Photo Research Company of USA were combined into an integrated IVL test system, and the luminous efficiency of the device prepared in the present application was tested at an electric current density of 10 mA / cm2at atmospheric pressure and room temperature. 2 The service life (luminance decay to 97% of the initial luminance) of the device prepared in the present application was tested by using the M6000 OLED service life test system of McScience Company at atmospheric pressure and room temperature, and the electric current density was 10 mA / cm2during the test. 2 .

[0449] The test results of the luminous properties of the obtained organic electroluminescent device are shown in Table 1. Table 1 shows the test results of the luminous properties of the organic electroluminescent device prepared by using the compound prepared in the present application and the comparative material.

[0450] Table 1 Test results of the luminous properties of the organic electroluminescent device

[0451]

[0452]

[0453] [Device Examples 26 to 36]

[0454] The ITO glass substrate was cleaned by ultrasonic cleaning with 5% glass cleaning solution for 2 times, 20 minutes each time, and then cleaned by ultrasonic cleaning with deionized water for 2 times, 10 minutes each time. The substrate was cleaned by ultrasonic cleaning with acetone and isopropyl alcohol for 20 minutes each, and then dried at 120°C. The P-1:HI = 97:3 (mass ratio) was vacuum evaporated on the ITO substrate as a hole injection layer, and the thickness was 10 nm. The compound 1-29 of the present application was vacuum evaporated on the hole injection layer as a hole transport layer, and the thickness was 120 nm. The RH-1:RH2:RD = 48:48:4 (mass ratio) was vacuum evaporated on the hole transport layer as a light-emitting layer, and the thickness was 30 nm. The compound 2-470 of the present application was vacuum evaporated on the light-emitting layer as an electron transport layer, and the thickness was 30 nm. LiF was vacuum evaporated on the electron transport layer as an electron injection layer, and the thickness was 1 nm. Al was vacuum evaporated on the electron injection layer as a cathode, and the thickness was 70 nm.

[0455] Device Examples 27 to 36: The compound 1-44, 1-92, 1-110, 1-1-2, 1-239, 1-354, 1-392, 1-453, 1-675, 1-851 of the present application were respectively used instead of the compound 1-29 of the present application in Device Example 26 as a hole transport layer material, and the compound 2-300, 2-298, 2-245, 2-289, 2-994, 2-172, 2-1017, 2-503, 2-140, 2-523 of the present application were respectively used instead of the compound 2-470 of the present application in Device Example 26 as an electron transport layer material, and the same procedure as in Device Example 26 was applied except for the above, to thereby prepare an organic electroluminescent device.

[0456] Comparative Examples 15 to 19: The compound 1-44, 1-110, 1-192, 1-675, 1-851 of the present application were respectively used instead of the compound 1-29 of the present application in Device Example 26 as a hole transport layer material, and Bphen was used instead of the compound 2-470 of the present application in Device Example 26 as an electron transport layer material, and the same procedure as in Device Example 26 was applied except for the above, to thereby prepare an organic electroluminescent device.

[0457] Comparative Examples 20 to 24: TAPC was used instead of the compound 1-29 of the present application in Device Example 26 as a hole transport layer material, and the compound 2-140, 2-245, 2-289, 2-300, 2-523 of the present application were respectively used instead of the compound 2-470 of the present application in Device Example 26 as an electron transport layer material, and the same procedure as in Device Example 26 was applied except for the above, to thereby prepare an organic electroluminescent device.

[0458] The organic electroluminescent device was tested for luminous efficiency by using a combined IVL test system consisting of a test software, a computer, a K2400 digital source meter produced by Keithley Co. in USA, and a PR788 spectral scanning luminance meter produced by Photo Research Co. in USA. The test for lifetime was performed by using an M6000 OLED lifetime test system produced by McScience Co. The test was performed in an atmospheric environment at room temperature.

[0459] The results of the test for the luminous characteristics of the obtained organic electroluminescent device are shown in Table 2. Table 2 shows the results of the test for the luminous characteristics of the organic electroluminescent device prepared by using the compound of the present application and the comparative material.

[0460] Table 2 Test for the luminous characteristics of the organic electroluminescent device

[0461]

[0462]

[0463] It should be noted that the present application has been described in particular detail with reference to certain embodiments thereof. However, it will be understood by those of ordinary skill in the art that various changes in form and details can be made therein without departing from the spirit and scope of the present application. Accordingly, although specific embodiments have been illustrated and described herein, it should be appreciated that the present application is not limited to the details of the above-described embodiments, but can be implemented with various changes and modifications, without departing from the spirit and scope of the present application.

Claims

1. An organic electroluminescent device comprising an anode, a hole-transporting region, a light-emitting layer, an electron-transporting region, a cathode, characterized in that The hole transport region comprises a structure shown in Formula 1, and the electron transport region comprises a structure shown in Formula 2, In Formula 1, The Ar1-Ar4 are the same or different and are selected from any one of the following structures, The ring A is selected from a substituted or unsubstituted C3-C12 alicyclic ring, a substituted or unsubstituted C2-C12 aliphatic heterocyclic ring; The d is selected from 1, 2, 3, 4 or 5; The Ra, Rb are the same or different and are selected from any one of a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C3-C12 cycloalkenyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, a fused ring group of a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C12 alicyclic ring and a C2-C30 heteroaromatic ring, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C12 alkoxy group, or the Ra, Rb form a substituted or unsubstituted spiro ring; The R6 are the same or different and are selected from any one of hydrogen, deuterium, a cyano group, a halogen, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1-C12 alkoxy group; The c1 is selected from 0, 1, 2, 3, 4 or 5; the c2 is selected from 0, 1, 2, 3 or 4; the c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R6, the two or more R6 are the same or different from each other, or two adjacent R6 are connected to each other to form a substituted or unsubstituted alicyclic ring or a substituted or unsubstituted aliphatic heterocyclic ring; The L0 is selected from any one of a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C12 alicyclic ring and a C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C3-C12 alicyclic ring and a C2-C30 heteroaromatic ring fused ring group, or a combination thereof; In Formula 2, The R1, R2 are the same or different and are selected from any one of a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C2-C12 heterocycloalkyl group, a C3-C12 cycloalkenyl group, a C6-C30 aryl group, a C3-C12 alicyclic ring and a C6-C30 aromatic ring fused ring group, a silyl group, a C1-C12 alkoxy group; or the R1, R2 are connected to each other to form a substituted or unsubstituted ring. R1, R2may be substituted by one or more substituents selected from any one of deuterium, cyano, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic rings, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic rings, substituted or unsubstituted silyl group; when two or more substituents exist, the two or more substituents are the same as or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted ring; z is selected from CH or N, and z bonded to L1is selected from C atom; R3, R4are selected from any one of hydrogen, deuterium, cyano, halogen, methyl, trifluoromethyl, C3-C12cycloalkyl, C2-C12heterocycloalkyl, C3-C12cycloalkenyl, C6-C30aryl, C2-C30heteroaryl, fused ring group of C3-C12alicyclic and C6-C30aromatic rings, fused ring group of C3-C12alicyclic and C2-C30heteroaromatic rings, substituted or unsubstituted silyl group, which are the same as or different from each other; R3, R4may be substituted by one or more substituents selected from any one of deuterium, halogen, substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted C3-C12cycloalkyl, substituted or unsubstituted C2-C12heterocycloalkyl, substituted or unsubstituted C3-C12cycloalkenyl, substituted or unsubstituted C6-C30aryl, substituted or unsubstituted C2-C30heteroaryl, substituted or unsubstituted fused ring group of C3-C12alicyclic and C6-C30aromatic rings, substituted or unsubstituted fused ring group of C3-C12alicyclic and C2-C30heteroaromatic rings, substituted or unsubstituted silyl group; when two or more substituents exist, the two or more substituents are the same as or different from each other, or adjacent two substituents are connected to each other to form a substituted or unsubstituted ring; a, b are selected from 0, 1, 2, 3 or 4, which are the same as or different from each other; when two or more R3, R4exist, the two or more R3, R4are the same as or different from each other, or adjacent two R3, R4are connected to each other to form a substituted or unsubstituted ring; L1is selected from any one of substituted or unsubstituted C6-C30arylene, substituted or unsubstituted C2-C30heteroarylene, substituted or unsubstituted C3-C12alicyclic and C6-C30aromatic ring-based fused ring group, substituted or unsubstituted C3-C12alicyclic and C2-C30heteroaromatic ring-based fused ring group; L2is selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C12 alicyclo and C6-C30 aryl fused ring group, and a substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroaryl fused ring group; X is selected from O, S, or N(Rc); Rcis selected from any one of a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C3-C12 cycloalkenyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C12 alicyclo and C6-C30 aryl fused ring group, a substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroaryl fused ring group, a substituted or unsubstituted silyl, and a substituted or unsubstituted C1-C12 alkoxy; x is selected from C(R7) or N, and is the same or different; R7is selected from any one of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C3-C12 cycloalkenyl, and a substituted or unsubstituted silyl; when two or more R7are present, two or more R7are the same or different from each other, or two adjacent R7are connected to each other to form a substituted or unsubstituted ring; R5is selected from any one of hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C12 alkyl, a substituted or unsubstituted C3-C12 cycloalkyl, a substituted or unsubstituted C2-C12 heterocycloalkyl, a substituted or unsubstituted C3-C12 cycloalkenyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted C3-C12 alicyclo and C6-C30 aryl fused ring group, a substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroaryl fused ring group, and a substituted or unsubstituted silyl.

2. An organic electroluminescent device according to claim 1, characterized in that Ar1-Ar4are the same or different and are selected from any one of the following structures, R6is selected from any one of hydrogen, deuterium, cyano, halogen, methyl, ethyl, isopropyl, tert-butyl, benzo-cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, furanyl, thienyl, benzo-furanyl, benzo-thienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, and triphenylsilyl; R6may be substituted by one or more substituents selected from any one of deuterium, cyano, halogen, methyl, ethyl, isopropyl, tert-butyl, benzo-cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, furanyl, thienyl, benzo-furanyl, benzo-thienyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other; c1is selected from 0, 1, 2, 3, 4 or 5; c2is selected from 0, 1, 2, 3 or 4; c3is selected from 0, 1, 2, 3, 4, 5, 6 or 7; c4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; c5is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; c6is selected from 0, 1, 2 or 3; c7is selected from 0, 1 or 2; c8is selected from 0, 1, 2, 3, 4, 5 or 6; c9is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; d1is the same or different and is selected from 1, 2, 3 or 4.

3. An organic electroluminescent device according to claim 1, characterized in that L0is selected from any one of the following structures, Rd1, Rd2, Re1, Re2, Rf1, Rf2are the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy; R8is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, substituted or unsubstituted fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy; said e1 is selected from 0, 1, 2, 3, or 4; said e2 is selected from 0, 1, 2, 3, 4, 5, or 6; said e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said e4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said e5 is selected from 0, 1, 2, or 3; said e6 is selected from 0, 1, or 2; said e7 is selected from 0, 1, 2, 3, 4, or 5; said e8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said e9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said e 10 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; when there are two or more R8, the two or more R8 are the same or different from each other, or two adjacent R8 are connected to each other to form a substituted or unsubstituted ring.

4. An organic electroluminescent device according to claim 1, characterized in that The is selected from any one of the structures shown below, z is the same or different and is selected from CH or N, z bonded with L1is selected from C; R1, R2are the same or different and selected from any one of C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C30 aryl, C3-C12 alicyclo and C6-C30 arycyclo fused ring group, silyl, C1-C12 alkoxy; R1, R2may be substituted by one or more substituents selected from any one of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroarylcyclo fused ring group, substituted or unsubstituted silyl; when there are two or more substituents, the two or more substituents are the same or different from each other, or two adjacent substituents are connected to each other to form a substituted or unsubstituted alicyclo or alicyclohetero ring; R2' is selected from any one of single bond, substituted or unsubstituted C3-C12 cycloalkylene, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroarylcyclo fused ring group, or a combination thereof; R3, R4are the same or different and selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroarylcyclo fused ring group, substituted or unsubstituted silyl; R9is the same or different and selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C12 alicyclo and C6-C30 arycyclo fused ring group, substituted or unsubstituted C3-C12 alicyclo and C2-C30 heteroarylcyclo fused ring group, substituted or unsubstituted silyl; b is selected from 0, 1, 2, 3, or 4; when two or more R3are present, two or more R3are the same as or different from each other, or two adjacent R3are connected to each other to form a substituted or unsubstituted ring; a1 is selected from 0, 1, 2, or 3; a2 is selected from 0, 1, 2, 3, or 4; when two or more R4are present, two or more R4are the same as or different from each other, or two adjacent R4are connected to each other to form a substituted or unsubstituted ring; f1 is selected from 0, 1, 2, 3, or 4; f2 is selected from 0, 1, 2, 3, 4, 5, or 6; f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; f6 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; when two or more R9are present, two or more R9are the same as or different from each other, or two adjacent R9are connected to each other to form a substituted or unsubstituted ring; Rg, Rh, and Ri, which are the same or different, are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, and substituted or unsubstituted silyl.

5. An organic electroluminescent device according to claim 4, characterized in that R1and R2, which are the same or different, are selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, and triphenylsilyl; R1and R2may be substituted with one or more substituents selected from any one or a combination of deuterium, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclic and C6-C30 aromatic, fused ring group of C3-C12 alicyclic and C2-C30 heteroaromatic, and substituted or unsubstituted silyl; when two or more substituents are present, two or more substituents are the same as or different from each other; R1and R2may be substituted with one or more substituents selected from any one or a combination of deuterium, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclic and C6-C30 aromatic, fused ring group of C3-C12 alicyclic and C2-C30 heteroaromatic, and substituted or unsubstituted silyl; when two or more substituents are present, two or more substituents are the same as or different from each other; R2' is selected from any one or combination of a single bond, a benzcyclopropylene group, a benzcyclobutylene group, a benzcyclopentylene group, a benzcyclohexylene group, a benzcycloheptylene group, a benzcyclopentenylene group, a benzcyclohexenylene group, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a terphenylene group, a fluorenylene group, a carbazolylene group, a furanylene group, a thienylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a quinazolinylene group, a quinoxalinylene group, a phenanthrolinylene group, a benzoxazolylene group, a benzothiazolylene group; R2' can be substituted by one or more substituents selected from any one or combination of deuterium, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, a fused ring group of C3-C12 alicyclo and C6-C30 aryl, a fused ring group of C3-C12 alicyclo and C2-C30 heteroaryl, a substituted or unsubstituted silyl group; when two or more substituents are present, the two or more substituents are the same as or different from each other; R3, R4 are the same or different and are selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, terphenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, or a combination thereof; R9is selected from any one of hydrogen, deuterium, halogen, cyano, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridyloxazolyl, pyridylthiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; R3, R4, R9may be substituted by one or more substituents selected from deuterium, halogen, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridyloxazolyl, pyridylthiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; when there are two or more substituents, the two or more substituents are the same or different from each other; b is selected from 0, 1, 2, 3 or 4; when there are two or more R3, the two or more R3are the same or different from each other, or two adjacent R3are connected to each other to form a substituted or unsubstituted ring; a1is selected from 0, 1, 2 or 3; a2is selected from 0, 1, 2, 3 or 4; when there are two or more R4, the two or more R4are the same or different from each other, or two adjacent R4are connected to each other to form a substituted or unsubstituted ring; said f1 is selected from 0, 1, 2, 3 or 4; said f2 is selected from 0, 1, 2, 3, 4, 5 or 6; said f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; said f6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; when there are two or more R9, the two or more R9 are the same as or different from each other, or two adjacent R9 are connected to each other to form a substituted or unsubstituted ring; said Rg, Rh, Ri are the same or different and are selected from any one of methyl, ethyl, isopropyl, tert-butyl, benzo-cyclopropyl, benzo-cyclobutyl, benzo-cyclopentyl, benzo-cyclohexyl, benzo-cycloheptyl, benzo-cyclopentenyl, benzo-cyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; said Rg, Rh, Ri can be substituted by one or more substituents selected from any one or combination of deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring of C3-C12 alicyclic and C6-C30 aromatic, fused ring of C3-C12 alicyclic and C2-C30 heteroaromatic, substituted or unsubstituted silyl; when there are two or more substituents, the two or more substituents are the same as or different from each other.

6. An organic electroluminescent device according to claim 1, characterized in that said L1 is selected from any one of the following structures, said y is the same or different and is selected from CH or N; The R 10 The same or different are selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, and substituted or unsubstituted C1-C12 alkoxy. said h1 is the same or different and is selected from 0, 1, 2, 3 or 4; said h2 is the same or different and is selected from 0, 1, 2 or 3; said h3 is the same or different and is selected from 0, 1 or 2; said h4 is the same or different and is selected from 0, 1, 2, 3, 4, 5 or 6; said h5 is the same or different and is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; Rj, Rk, Rmare the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkoxy.

7. The organic electroluminescent device according to claim 1, wherein L2is selected from a single bond or any one of the following structures, Rp, Rq, Rnare the same or different and are selected from any one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted silyl; The R 11 The same or different are selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C2-C12 heterocycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, and substituted or unsubstituted C1-C12 alkoxy. said g1 is selected from 0, 1, 2, 3, or 4; said g2 is selected from 0, 1, 2, 3, 4, 5, or 6; said g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said g4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said g5 is selected from 0, 1, 2, or 3; said g6 is selected from 0, 1, or 2; said g7 is selected from 0, 1, 2, 3, 4, or 5; said g8 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; said g9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; said g 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; when there are two or more R 11 groups, two or more of R 11 groups are the same or different from each other, or two adjacent R 11 groups are connected to each other to form a substituted or unsubstituted ring.

8. The organic electroluminescent device according to claim 1, wherein The is selected from any one of the structures shown below, X is selected from O, S, or N(Rc); Rcis selected from any one of methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, deuterated phenyl, methylphenyl, deuterated biphenyl, deuterated naphthyl, pyridyl, pyrimidyl, triazinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, fluorenyl, benzoxazolyl, benzothiazolyl; R5is selected from any one of methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, fluorenyl, carbazolyl, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, phenanthrolinyl, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridyloxazolyl, pyridylthiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl. The R5may be substituted with one or more substituents selected from any one or a combination of deuterium, cyano, halogen, trifluoromethyl, C1-C12 alkyl, C3-C12 cycloalkyl, C2-C12 heterocycloalkyl, C3-C12 cycloalkenyl, C6-C18 aryl, C2-C25 heteroaryl, fused ring group of C3-C12 alicyclo and C6-C30 arycyclo, fused ring group of C3-C12 alicyclo and C2-C30 heteroarycyclo, substituted or unsubstituted silyl; when there are two or more substituents, the two or more substituents are the same as or different from each other; The R7is the same or different and is selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, trifluoromethyl, methyl, ethyl, isopropyl, tert-butyl, benzcyclopropyl, benzcyclobutyl, benzcyclopentyl, benzcyclohexyl, benzcycloheptyl, benzcyclopentenyl, benzcyclohexenyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl; The R7may be substituted with one or more substituents selected from any one of deuterium, cyano, halogen, trifluoromethyl; The n1is selected from 0, 1, 2, 3 or 4; the n2is selected from 0, 1, 2 or 3; the n3is selected from 0, 1 or 2; the n4is selected from 0, 1, 2, 3, 4, 5 or 6; the n5is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the n6is selected from 0, 1, 2, 3, 4 or 5; the n7is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

9. An organic electroluminescent device according to claim 1, characterized in that The formula 1 is selected from any one of the following structures, 10. The organic electroluminescent device according to claim 1, wherein The formula 2 is selected from any one of the following structures, The formula 1 is selected from any one of the following structures,

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