Compound containing carbazole fused ring and organic electroluminescent device thereof

Abstract

The invention provides a carbazole ring-containing compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The carbazole ring-containing compound provided by the invention has relatively high glass transition temperature and molecular thermal stability, and has a proper HOMO energy level, so that the distribution of electrons and holes in a luminescent layer is more balanced, and the recombination efficiency of excitons in the luminescent layer is improved; when the compound is applied to a light-emitting layer of an organic light-emitting device, the light-emitting efficiency and the service life of the device can be effectively improved. Meanwhile, the preparation method of the compound is simple, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has good application effects and industrialization prospects.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a compound containing a carbazole ring and an organic electroluminescent device thereof. BACKGROUND

[0002] Organic Light-Emitting Diode (OLED) is a kind of organic semiconductor material-based light-emitting device, which is driven by electric field to make carriers recombine in the light-emitting layer, form excitons and release energy to emit light. Compared with traditional liquid crystal display, OLED has self-luminescent characteristics, and does not need additional backlight source, so it has higher contrast, wider viewing angle and faster response speed.

[0003] An organic electroluminescent device is usually composed of an anode, a cathode and an organic layer therebetween. In most cases, in order to improve the efficiency and stability of the organic electroluminescent device, the structure of the organic layer is designed as a multilayer structure composed of different materials, such as hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, light-emitting auxiliary layer, cover layer, etc. When working, the application of voltage makes holes and electrons meet in the light-emitting layer to form singlet excitons (accounting for 25%) and triplet excitons (accounting for 75%). Traditional fluorescent materials only utilize singlet light, and the theoretical efficiency upper limit is 25%; while phosphorescent materials (such as Ir, Pt complexes) and thermally activated delayed fluorescence (TADF) materials can realize triplet light emission, and the efficiency is broken through to 100%.

[0004] After decades of development, OLED technology has basically met people's daily needs in various performance aspects, but the brightness, luminous efficiency and service life of the device still need to be further improved. The light-emitting layer, as an important part of OLED, usually contains a host material and a dopant material. The host material can efficiently transfer energy to the dopant material, thereby improving the luminous efficiency of the device. By controlling the structure and composition of the light-emitting layer material, the light-emitting color of the device can be directly affected and the luminous efficiency of the device can be improved. Therefore, it is crucial to design a light-emitting layer material with better performance, which has become the current research focus. SUMMARY

[0005] The purpose of the present application is to provide a compound containing a carbazole ring and an organic electroluminescent device thereof. When the compound containing a carbazole ring provided by the present application is applied to the light-emitting layer of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device can be improved, solving the problems of low luminous efficiency and short service life of the organic electroluminescent device in the prior art.

[0006] Specifically, the present application provides a compound containing a carbazole ring, which has a general formula shown in structural formula 1,

[0007]

[0008] wherein one of Y1, Y2is selected from a single bond, and the other is selected from an O atom, an S atom, or C(R1R2);

[0009] v is the same or different selected from C(R3) or an N atom, and v at the bonding site is selected from C;

[0010] Ar1is selected from a group represented by Formula 1-a;

[0011] Y3is selected from an O atom, an S atom, C(R4R5), or N(R6);

[0012] z is the same or different selected from C(R7) or an N atom, and z at the bonding site is selected from C;

[0013] R1, R2, R4, R5are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or are connected to each other between R1and R2, between R4and R5to form a substituted or unsubstituted ring;

[0014] R6is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0015] R3, R7are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or are connected to each other between two adjacent R3, between two R7to form a substituted or unsubstituted ring;

[0016] provided that at least one group represented by Formula 1-b is contained in Formula 1;

[0017] x is the same or different selected from C(R8) or an N atom, and x at the bonding site is selected from C;

[0018] The R8 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R8s are connected to each other to form a substituted or unsubstituted ring;

[0019] The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0020] The L1, L a It is independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused cycloalkanes, and substituted or unsubstituted C2-C30 heteroarylene.

[0021] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the carbazole-containing compound described in the present invention.

[0022] Beneficial effects: The carbazole-containing compound provided by this invention has a high glass transition temperature and molecular thermal stability, and possesses an appropriate HOMO energy level, resulting in a more balanced distribution of electrons and holes in the emissive layer and improving the exciton recombination efficiency in the emissive layer. When applied to the emissive layer of organic electroluminescent devices, it can effectively improve the luminous efficiency and lifespan of the device. Furthermore, the preparation method of the compound of this invention is simple, the raw materials are readily available, and it can be widely used in fields such as organic thin-film transistors and panel displays, demonstrating good application effects and industrialization prospects. Detailed Implementation

[0023] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0024] In the compounds of this invention, any atom not specified as a particular isotope contains any stable isotope of that atom, and contains atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0025] Examples of the halogen according to the present application can include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0026] The "C1 to C15" in the "substituted or unsubstituted C1 to C15 alkyl" according to the present application refers to the number of carbon atoms in the "alkyl" not including the number of carbon atoms in the substituent. The "C6 to C30" in the "substituted or unsubstituted C6 to C30 aryl" according to the present application refers to the number of carbon atoms in the "aryl" not including the number of carbon atoms in the substituent. The same applies to the following.

[0027] The alkyl according to the present application refers to a monovalent group in which one hydrogen atom is removed from an alkane molecule. The number of carbon atoms in the alkyl is C1 to C15, preferably C1 to C10. Examples of the alkyl include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, and the like.

[0028] The chain alkyl having more than three carbon atoms according to the present application includes isomers thereof, for example, propyl includes n-propyl, isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, t-butyl. The same applies to the following.

[0029] The alkenyl according to the present application refers to a monovalent group in which one hydrogen atom is removed from an alkene molecule, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and examples can include, but are not limited to, ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, and the like.

[0030] The alkoxy according to the present application refers to a monovalent group in which one hydrogen atom is removed from an alkoxy molecule, preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms, and examples can include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, and the like.

[0031] The aryl according to the present application refers to a monovalent group in which one hydrogen atom is removed from the aromatic nucleus of an aromatic hydrocarbon molecule. The aryl includes monocyclic aryl, polycyclic aryl, and fused ring aryl. The number of carbon atoms in the aryl is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and further preferably C6 to C12. Examples of the aryl include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, naphthyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, phenanthryl, triphenylenyl, anthryl, pyrenyl, fluorenyl, spirobifluorenyl, spiroanthrafluorenyl, benzofluorenyl, benzospirobifluorenyl, and the like.

[0032] The alicyclic group according to the present application refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which can be completely unsaturated or partially unsaturated. For example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but not limited thereto. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure, such as adamantane, norbornane, camphane, etc., but not limited thereto.

[0033] The fused ring group of the alicyclic ring and the aromatic ring according to the present application refers to the total of the one-valent group after the alicyclic ring and the aromatic ring are fused together and one hydrogen atom is removed. Examples of the fused ring group of the alicyclic ring and the aromatic ring can include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutene, benzocycloheptane, benzocycloheptene, etc., but not limited thereto. The number of carbon atoms of the alicyclic ring is C3 to C15, preferably C3 to C10. The number of carbon atoms of the aromatic ring is C6 to C30, preferably C6 to C18, and more preferably C6 to C12.

[0034] The heteroaryl group according to the present application refers to a one-valent group in which at least one aromatic core carbon atom in the aryl group is substituted with a heteroatom. The number of carbon atoms of the heteroaryl group is C2 to C30, preferably C2 to C15, and more preferably C2 to C10. The heteroatom includes, but is not limited to, the following atoms, O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl groups and fused ring heteroaryl groups. Examples of the heteroaryl group include, but are not limited to, the following groups, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, furanyl, benzofuranyl, dibenzofuranyl, benzdibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzdibenzothienyl, carbazolyl, etc., but not limited thereto.

[0035] 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, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkenyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C3 to C30 alicyclic ring and C6 to C60 aromatic ring fused ring group, and a substituted or unsubstituted C3 to C30 alicyclic ring and C2 to C60 heteroaromatic ring fused ring group. 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. 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 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. 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 biphenyl, substituted or unsubstituted naphthyl. The "alkylsilyl group" means at least one substituent R k is an alkyl group, and the preferred alkylsilyl group specifically includes trimethylsilyl, triethylsilyl, triisopropylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, but not limited thereto; the "arylsilyl group" means at least one substituent R k is an aryl group, and the preferred arylsilyl group specifically includes triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and the like, but not limited thereto.

[0036] The arylene group according to the present application means a divalent group in which two hydrogen atoms are removed from the aromatic ring carbon of an aromatic hydrocarbon molecule. The number of carbon atoms of the arylene group is C6-C30, preferably C6-C20, and more preferably C6-C10. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a fused ring arylene group, or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups, phenylene, biphenylene, terphenylene, naphthylene, anthrylene, phenanthrylene, triphenylylene, pyrenylene, pyrenthrylene, indenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, spirobifluorenylene, benzosprio-bifluorenylene, and the like.

[0037] The alicyclic and aromatic sub-fused ring group according to the present application refers to a total of divalent groups after removing two hydrogen atoms from the alicyclic and aromatic fused together. Examples of the alicyclic and aromatic sub-fused ring group can include, but are not limited to, sub-indenyl, indenyl, sub-tetrahydronaphthyl, sub-dihydronaphthyl, sub-benzocyclopropanyl, sub-benzocyclobutanyl, sub-benzocyclobutenyl, sub-naphthocyclopentanyl, etc. The number of carbon atoms of the alicyclic group is C3 to C15, preferably C3 to C10. The number of carbon atoms of the aromatic group is C6 to C30, preferably C6 to C18.

[0038] The sub-heteroaryl group according to the present application refers to a divalent group in which at least one carbon atom in the aryl group is replaced by a heteroatom. The number of carbon atoms of the sub-heteroaryl group is C2 to C30, preferably C2 to C20, and more preferably C2 to C10. The heteroatom includes, but is not limited to, O, S, N, Si, B, P, etc. The sub-heteroaryl group includes a monocyclic sub-heteroaryl group, a polycyclic sub-heteroaryl group, a fused ring sub-heteroaryl group, or a combination thereof. Examples of the sub-heteroaryl group include, but are not limited to, sub-pyridyl, sub-pyrimidyl, sub-quinolyl, sub-isoquinolyl, sub-furyl, sub-benzofuryl, sub-dibenzofuryl, sub-benzodibenzofuryl, sub-thiophenyl, sub-benzothiophenyl, sub-dibenzothiophenyl, sub-benzodibenzothiophenyl, etc.

[0039] The "substituted or unsubstituted" in the present application means unsubstituted or substituted with one or more substituents selected from the group consisting of a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 alicyclic group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C6 to C60 aryloxy group, a substituted or unsubstituted C2 to C60 heteroaryl group, preferably a halogen atom, a cyano group, a nitro group, a C1 to C12 alkyl group, a C3 to C12 alicyclic group, a C3 to C12 heterocycloalkyl group, a C6 to C30 aryl group, a C3 to C30 heteroaryl group, and in the case of being substituted with a plurality of substituents, the plurality of substituents are the same as or different from each other; preferably, means unsubstituted or substituted with one or more substituents selected from the group consisting of a fluorine atom, a cyano group, a methyl group, a trifluoromethyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a t-butyl group, a cyclopropane group, a methyl-substituted cyclopropane group, an ethyl-substituted cyclopropane group, a cyclobutane group, a methyl-substituted cyclobutane group, an ethyl-substituted cyclobutane group, a cyclopentane group, a methyl-substituted cyclopentane group, an ethyl-substituted cyclopentane group, a cyclohexane group, a methyl-substituted cyclohexane group, an ethyl-substituted cyclohexane group, an n-propyl-substituted cyclohexane group, an n-butyl-substituted cyclohexane group, a cyclohexane-substituted cyclohexane group, a cycloheptane group, a cyclopentene group, a methyl-substituted cyclopentene group, an ethyl-substituted cyclopentene group, a cyclohexene group, a cycloheptene group, an adamantane group, a methyl-substituted adamantane group, an ethyl-substituted adamantane group, a norbornane group, a methyl-substituted norbornane group, an ethyl-substituted norbornane group, a tetrahydropyrrole group, a piperidine group, a morpholine group, a thiomorpholine group, a methyl-substituted piperazine group, an ethyl-substituted piperazine group, a phenyl-substituted piperazine group, a naphthyl-substituted piperazine group, a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a spiro-cyclopentyl-fluorenyl group, a spiro-cyclohexyl-fluorenyl group, a spiro-adamantyl-fluorenyl group, a spiro-cyclopentenyl-fluorenyl group, a spiro-cyclohexenyl-fluorenyl group, an N-phenylcarbazole group, a dibenzofuranyl group, a dibenzothiophenyl group, and in the case of being substituted with a plurality of substituents, the plurality of substituents are the same as or different from each other.

[0040] In the present application, "*-" means a moiety connected to another substituent. "*-" can be connected to any optional position of the connected group / fragment.

[0041] In the present application, when a substituent or a connecting site is indicated to be through two or more rings, it means that it can be connected to any one of the two or more rings, specifically, to any one of the corresponding optional positions of the rings. For example, may be represented as may be represented as and so on.

[0042] In the present application, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring. For example, may mean may mean may mean

[0043] and so on.

[0044] In the present application, "two adjacent groups can be connected to each other to form a substituted or unsubstituted ring" means that the adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be a single ring or a polycyclic group. In addition, the ring formed by the combination of the adjacent groups can be connected to another ring to form a spiro structure. As an example, the following is shown:

[0045]

[0046] In the present application, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of both, and the ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, for example, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanobenzene, cyclohexene, cyclohexane, cyclohexanobenzene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0047] The present application provides a compound containing a carbazole ring, having a general formula shown in Structural Formula 1,

[0048]

[0049] wherein one of Y1, Y2 is selected from a single bond, and the other is selected from an O atom, an S atom, or C(R1R2);

[0050] v is the same or different and is selected from C(R3) or an N atom, and v at the bonding site is selected from C;

[0051] Ar1 is selected from a group shown in Formula 1-a;

[0052] Y3 is selected from an O atom, an S atom, C(R4R5), or N(R6);

[0053] z is the same or different selected from C(R7) or N atom, z at the bonding site is selected from C;

[0054] R1, R2, R4, R5are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R1and R2, R4and R5are connected to each other to form a substituted or unsubstituted ring;

[0055] R6is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0056] R3, R7are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R3and R3, R7and R7are connected to each other to form a substituted or unsubstituted ring;

[0057] provided that at least one group represented by formula 1-b is contained in formula 1;

[0058] x is the same or different selected from C(R8) or N atom, x at the bonding site is selected from C;

[0059] R8is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R8and R8are connected to each other to form a substituted or unsubstituted ring;

[0060] ring A is selected from substituted or unsubstituted C3-C15 alicyclyl;

[0061] L1, La independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aryl fused ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0062] Preferably, the Ar1contains a group represented by Formula 1-b.

[0063] Preferably, the L1contains a group represented by Formula 1-b.

[0064] Preferably, the Ar1contains a group represented by Formula 1-b. Preferably, the L1contains a group represented by Formula 1-b.

[0065] Preferably, the Formula 1 is selected from any one of the following structural formulas:

[0066]

[0067] The definitions of the Ar1, L1, v, R1, R2are the same as those in Formula 1.

[0068] Preferably, in each of the structural formulas of Formula 1, Formula 1-1 to Formula 1-18, at most 3, or at most 2, or at most 1 v is selected from an N atom.

[0069] Preferably, the R3is selected from any one or more of hydrogen, deuterium, a cyano group, a halogen, a nitro group, a group represented by Formula 1-b, and a substituted or unsubstituted group selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, an adamantane group, a norbornane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolyl group, a quinoxalyl group, a naphthrydinyl group, an indolyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a carbazolyl group, a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a tri-tert-butylsilyl group, a tert-butyldimethylsilyl group, a vinyl dimethylsilyl group, a propyl dimethylsilyl group, a triphenylsilyl group, a diphenylmethylsilyl group, a phenyl dimethylsilyl group, in the case of being substituted with a plurality of substituents, the plurality of substituents being the same as or different from each other, or the adjacent two R3are connected to each other to form a substituted or unsubstituted benzene ring, a naphthalene ring, an anthracene ring, a pyridine ring, a pyrimidine ring, a cyclopentane ring, a cyclohexane ring.

[0070] Preferably, 1 or 2 of R8are selected from a group represented by Formula 1-b.

[0071] Preferably, said Ar1is selected from any one of the following structures:

[0072]

[0073]

[0074]

[0075] said R7is the same or different selected from hydrogen, deuterium, cyano, halogen, nitro, a group represented by 1-b, a substituted or unsubstituted group of any one or more of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, in case of being substituted with multiple substituents, the multiple substituents are the same or different from each other; or said adjacent two R7s are connected to each other to form a substituted or unsubstituted group of any one of phenyl ring, naphthyl ring, anthracene ring, pyridyl ring, pyrimidinyl ring, cyclopentane ring, cyclohexane ring;

[0076] R4, R5are the same or different selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, a group represented by 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, in case of being substituted with a plurality of substituents, the plurality of substituents are the same as or different from each other, or R4and R5are connected to each other to form a substituted or unsubstituted ring;

[0077] R6is selected from the group consisting of hydrogen, deuterium, a group represented by 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, in case of being substituted with a plurality of substituents, the plurality of substituents are the same as or different from each other;

[0078] b is selected from 0, 1, 2, 3, or 4; b1is selected from 0, 1, 2, or 3; b2is selected from 0, 1, or 2; b3is selected from 0, 1, 2, 3, 4, 5, or 6; b4is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0079] Preferably, R1and R2, or R4and R5, are connected to each other to form any one of the following rings:

[0080]

[0081] R1and R2, or R4and R5, are connected to each other to form any one of the following rings: 20 identically or differently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, 1-b, and any one or more of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, wherein the plurality of substituents, if present, are identical or different from each other, or the two adjacent R 20 may be connected to each other to form a substituted or unsubstituted benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring;

[0082] R1and R2, or R4and R5, are connected to each other to form any one of the following rings: 21any one or more of hydrogen, deuterium, a group represented by formula 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclooctane group, adamantane group, norbornane group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, triphenylene group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolyl group, quinoxalyl group, naphthrydinyl group, indolyl group, furanyl group, thienyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, carbazolyl group, trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, tri-t-butylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylmethylsilyl group, phenyldimethylsilyl group, in the case where a plurality of substituents are present, the plurality of substituents are identical to or different from each other;

[0083] the R 22 , the R 23 are selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, a group represented by formula 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclooctane group, adamantane group, norbornane group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group, triphenylene group, pyridyl group, pyrimidinyl group, pyridazinyl group, pyrazinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolyl group, quinoxalyl group, naphthrydinyl group, indolyl group, furanyl group, thienyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, carbazolyl group, trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, tri-t-butylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylmethylsilyl group, phenyldimethylsilyl group, in the case where a plurality of substituents are present, the plurality of substituents are identical to or different from each other, or the R 22 and the R 23 are mutually linked to form a substituted or unsubstituted ring;

[0084] said p1 is independently selected from 0, 1, 2, 3, or 4; said p2 is independently selected from 0, 1, 2, 3, 4, 5, or 6; said p3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said p4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said p5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.

[0085] Preferably, 1 or 2 of R7 is selected from the group consisting of Formula 1-b.

[0086] Preferably, in Formula 1-b is selected from any one of the following structures:

[0087]

[0088]

[0089] said R8, R9 are the same or different selected from hydrogen, deuterium, halogen, cyano, nitro, any one or more of the following groups: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyl dimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, or the adjacent two R8 can be connected to each other to form a substituted or unsubstituted ring;

[0090] The n is independently selected from 0, 1, 2, or 3; the n1 is independently selected from 0, 1, or 2; the n2 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the n3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the n4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the n5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the n6 is independently selected from 0, 1, 2, 3, or 4; the n7 is independently selected from 0, 1, 2, 3, 4, or 5; and the n8 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7.

[0091] Preferably, L1, L a Independently selected from any one of a single bond or a group as shown below, or a combination thereof:

[0092]

[0093] The t that is the same or different is selected from C(R) 10 ) or N, the R 10 The same or different from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl; or the two adjacent R 10 They can connect with each other to form substituted or unsubstituted rings;

[0094] The T1 is independently selected from O atoms, S atoms, C(R) atoms, and S atoms. 11 R 12 ) or N(R 13 );

[0095] The T2 is independently selected from O atoms, S atoms, or N(R) atoms. 14 );

[0096] The ring B is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0097] The R 11 R 12 Independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, or said R 11and R 12 may be mutually connected to form a substituted or unsubstituted ring;

[0098] said R 13 , R 14 are independently selected from any one of hydrogen, deuterium, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C12 alicyclic group, a substituted or unsubstituted C6-C18 aryl group, a substituted or unsubstituted condensed ring group of C3-C15 alicyclic and C6-C30 aryl, a substituted or unsubstituted C2-C18 heteroaryl group, and a substituted or unsubstituted silyl group.

[0099] More preferably, said L1, L a are independently selected from any one of a single bond, or the following groups or combinations thereof:

[0100]

[0101]

[0102] said R 10 , R 15 are independently selected from any one of hydrogen, deuterium, a cyano group, a halogen, a nitro group, a group represented by Formula 1-b, a substituted or unsubstituted group of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidyl, pyridazyl, pyrazyl, triazyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthylidene, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, or a plurality of substituents are the same as or different from each other in case of being substituted with a plurality of substituents, or the adjacent two R 10 may be mutually connected to form a substituted or unsubstituted ring.

[0103] said R 14independently selected from the group consisting of hydrogen, deuterium, a group represented by 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothiophenyl, indolyl, and any combination thereof;

[0104] said d1 is independently selected from 0, 1, 2, 3, or 4; said d2 is independently selected from 0, 1, 2, or 3; said d3 is independently selected from 0, 1, or 2; said d4 is selected from 0, 1, 2, 3, 4, 5, or 6; said d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; said d6 is selected from 0, 1, 2, 3, 4, or 5; said d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; said d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14.

[0105] Preferably, 1 or 2 of R 10 are selected from a group represented by 1-b.

[0106] Further preferably, said L1, L a are independently selected from any one of a single bond or a group represented by the following or a combination thereof:

[0107]

[0108]

[0109] Preferably, the carbazole ring-containing compound represented by Formula 1 satisfies at least one of the following conditions:

[0110] i. 1 or 2 of R3 are a group represented by Formula 1-b;

[0111] ii. 1 or 2 of R7 are a group represented by Formula 1-b;

[0112] iii. 1 or 2 of R 10 are a group represented by Formula 1-b.

[0113] Preferably, the carbazole ring-containing compound represented by Formula 1 contains 1, 2, 3, or more groups represented by Formula 1-b. Most preferably, the carbazole ring-containing compound represented by Formula 1 is selected from any one of the following chemical structures:

[0114] Preferably, the carbazole ring-containing compound represented by Formula 1 contains 1, 2, 3, or more groups represented by Formula 1-b. Most preferably, the carbazole ring-containing compound represented by Formula 1 is selected from any one of the following chemical structures:

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162] The above lists some specific chemical structures of the carbazol ring-containing compounds of the present application of Structural Formula 1, but the present application is not limited to these chemical structures listed, and any carbazol ring-containing compounds based on Structural Formula 1, with substituents as defined above, should be included.

[0163] Further, the present application also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being located between the anode and the cathode or outside one or more of the electrodes, the organic layer containing the compound represented by Formula 1 of the present application.

[0164] Preferably, the organic layer is located between the anode and the cathode, the organic layer comprising at least one of a hole transport region, a light emitting layer, and an electron transport region, the light emitting layer being located between the hole transport region and the electron transport region, the light emitting layer containing the compound represented by Formula 1 of the present application.

[0165] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprising at least one of a hole transport region, a light emitting layer, and an electron transport region, the light emitting layer being located between the hole transport region and the electron transport region, the light emitting layer containing a host material and a dopant material, the host material containing the compound represented by Formula 1 of the present application.

[0166] Preferably, the organic layer is located on the side of the cathode facing away from the anode, the organic layer containing a capping layer, the capping layer containing the compound represented by Formula 1 of the present application.

[0167] Preferably, the organic electroluminescent device of the present application is a single-layer organic electroluminescent device or a stacked-layer organic electroluminescent device, the single-layer organic electroluminescent device being an organic electroluminescent device containing one light emitting unit, the stacked-layer organic electroluminescent device being an organic electroluminescent device in which N (N≥2) independent light emitting units are connected in series by a charge generation layer.

[0168] Preferably, the organic electroluminescent device of the present application is a single-layer organic electroluminescent device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0169] Preferably, the organic electroluminescent device of the present application is a stacked-layer organic electroluminescent device in which a first light emitting unit emitting light of a first color, an Nth light emitting unit emitting light of an Nth color, and a charge generation layer uniformly controlling charges between the first light emitting unit and the Nth light emitting unit are formed between an anode and a cathode, the light emitting units adjacent to each other being separated by an n-type charge generation layer and a p-type charge generation layer.

[0170] The organic electroluminescent device of the present application is generally formed on a substrate. The above-mentioned substrate can be any substrate as long as it does not change when electrodes are formed and organic layers are formed, for example, a substrate of glass, quartz, plastic, a polymer film, silicon, or the like. When the substrate is not transparent, the electrode opposite to it is preferably transparent or semi-transparent.

[0171] The material of each layer of the organic electroluminescent device according to the present application is not particularly limited, and a substance known in the art can be used. The organic layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are described below, respectively.

[0172] The anode according to the present application preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, etc. having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single layer structure or a multilayer structure including two or more layers, for example, the anode can have a single layer structure of ITO or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0173] The hole injection material according to the present application is preferably a material capable of lowering the interface barrier between the anode and the hole transport layer. Examples of such materials include polycyanide conjugated organic compounds, fulvene compounds, phthalocyanine metal complexes, compounds containing a carbazole ring, polymers, and the like. Specific examples can include metalloporphyrin, oligothiophene, arylamine-based organic materials, hexacyno-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto. In addition, another compound capable of p-doping can also be included.

[0174] The hole transport material according to the present application is preferably a material capable of receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer, and a material having high hole mobility and good stability. The hole transport material according to the present application is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of the hole injection layer, and can be a single layer structure or a multi-layer structure. As the hole transport layer material, for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, a polymer, or the like can be used. Specific examples can include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-di(9-carbazolyl) biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), 1,1-bis(4-(N,N'-di(p-tolyl)amino)phenyl)cyclohexane (TAPC), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylbenzenamine (DCDPA), and the like, but is not limited thereto.

[0175] The electron blocking layer according to the present application is preferably a material having a triplet (T1) energy level higher than that of the host material in the light-emitting layer, and capable of controlling and preventing electron transfer. For example, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; a spirofluorene derivative such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine; a dibenzofuran derivative such as N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and the like, but is not limited thereto.

[0176] The light-emitting layer described in this invention may contain only the guest material, or it may be in the form of the guest material being dispersed in the host material, wherein the host material may be composed of one or more materials.

[0177] As the host material for the light-emitting layer of this invention, a substance with a higher LUMO than the guest material and a lower HOMO than the guest material is preferably used, such as pyrene derivatives, styrene amine derivatives, etc. Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, tetraphenyl derivatives, etc., specifically, examples include 9-(3-(9H-carbazole-9-yl)phenyl)-9H-carbazole-3-nitrile (mCP-CN), 4,4'-bis(9-carbazole)biphenyl (CBP), 3,3'-bis(N-carbazole)-1,1'-biphenyl (mCBP), 1,3-dicarbazole-9-ylphenyl (mCP), di[2-((oxo)diphenylphosphino)phenyl]ether (DPEPO), 1,3,5-tris[(3-pyridine) 2,8-Di(9H-carbazole-9-yl)dibenzothiophene (DCzDBT), 3',5'-Di(carbazole-9-yl)-[1,1'-biphenyl]-3,5-dionitrile (DCzTPA), 4'-(9H-carbazole-9-yl)biphenyl-3,5-dionitrile (pCzB-2CN), 9-(9-phenyl-9H-carbazole-6-yl)-9H-carbazole (CCP), 9-(4-(9H-carbazole-9-yl)phenyl)-9H-3,9'-bicarbazole, 9,9'-bicarbazole -Diphenyl-9H,9'H-3,3'-Bicarbazole (BCzPh), 1,3,5-Tris(carbazole-9-yl)phenyl (TCP), Tris(4-carbazole-9-ylphenyl)amine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 2,7-bis(carbazole-9-yl)-9,9-dimethylfluorene (DMFL-CBP), 2,2',7,7'-tetra(carbazole-9-yl)-9,9-spirofluorene (spiro-CBP), N-(9,10-diphenyl-2-anthrayl)-N Compounds containing a carbazole ring as shown in Formula 1 of the present invention are included, but are not limited thereto. Compounds containing a carbazole ring as shown in Formula 1 of the present invention are preferred.

[0178] As the light emitting layer guest material of the present application, aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc. can be included, for example, 4,4'-bis(4-(9H-carbazol-9-yl)styryl)biphenyl (BSB4), 4,4'-di[4-(diphenylamino)styryl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenyltetracene (Rubrene), Coumarin 545T (C-525T) tris(2-phenyl-3-methyl-pyridine)iridium (Ir(3mppy)3), bis(2-(naphthalen-2-yl)pyridine)(acetylacetonate)iridium(III) (Ir(npy)2acac), tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (FIracac), etc., but are not limited thereto.

[0179] The hole blocking layer material according to the present application needs to have a good hole blocking ability in order to block holes in the light emitting layer. As such materials, imidazole derivatives, phenanthroline derivatives, metal complexes, triazine derivatives, etc. can be included. Specific examples can include 1,3,5-tri(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluoren-2-yl)4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine, etc., but are not limited thereto.

[0180] The electron transport layer material described in the present application can be a single layer structure or a multi-layer structure, which can include one or more electron transport materials, which can typically include metal complexes or / and nitrogen-containing heterocyclic derivatives, specific examples of which include tris-(8-hydroxyquinoline) aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1, O8)-(1,1'-biphenyl-4-hydroxy) aluminum (BAlq), lithium quinolate (Liq), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalen-2-yl) 4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl) 1,3,5-triazine (TmPPPyTz), poly[(9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium) propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] dibromide (PFNBr), tris(phenylquinoxaline) (TPQ), diphenyl-4-triphenylsilyl-phenyl phosphine oxide (TSPO1), 2-[4-(9,10-di-2-naphthalen-2-yl-2-anthracen-2-yl)phenyl] 1-phenyl-1H-benzimidazole (ZADN), and combinations thereof, but are not limited thereto.

[0181] The electron injection layer material described in the present application is preferably a material capable of reducing the interface barrier between the cathode and the electron transport layer. Examples include metals, alkali metals, alkaline earth metals, halides of alkali metals, halides of alkaline earth metals, oxides of alkali metals, oxides of alkaline earth metals, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances having high electron injection properties. Examples can include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline) aluminum, and the like. In addition, a plurality of these compounds can be used in combination.

[0182] The cathode according to the present application preferably uses a metal, an alloy, a conductive compound, and a mixture thereof, etc. having a small work function (specifically, a work function of 3.8 eV or less). The material for the cathode according to the present application can include a metal or an alloy thereof, a multilayer structure material, etc., for example, silver (Ag), aluminum (Al), magnesium (Mg), tin (Sn), magnesium silver (Mg:Ag), calcium / magnesium (Ca / Mg), etc. However, the present application is not limited thereto.

[0183] The anode and the cathode according to the present application can each be formed as a transmissive conductive material, a semi-transmissive and semi-reflective conductive material, or a reflective conductive material. Depending on the kind of the material forming the anode and the cathode, the organic electroluminescent device can be a top emission type, a bottom emission type, or a dual emission type.

[0184] The cover layer according to the present application can be a single layer structure composed of a single substance, or a single layer structure or a multilayer structure composed of different substances. The cover layer material can use an organic or inorganic substance having an appropriate refractive index, for example, a metal halide, an oxide, a nitride, an oxynitride, a sulfide, a selenide, an aromatic compound, a heteroaromatic compound, a heterocyclic compound, etc., and specific examples can include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris(8-hydroxyquinoline)aluminum (III) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-bis(9-carbazol) biphenyl (CBP), a compound containing a carbazole ring according to the present application, etc., but the present application is not limited thereto. The compound containing a carbazole ring according to the present application is preferred.

[0185] The n-type charge generation material according to the present application can be selected from one of the following materials or a combination thereof: tris-(8-hydroxyquinolinate) aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinate-N1,O8)-(1,1'-biphenyl-4-olate) aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-(N,N-dimethyl)-N-ethylammonium-propyl)-2,7-fluorene]-alt-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), etc., but is not limited thereto. In addition, an auxiliary n-type charge generation material can also be included. For example, the auxiliary n-type charge generation material can be an alkali metal such as Li, Cs, K, Rb, Na, or Fr, etc., but is not limited thereto, or an alkaline earth metal such as Be, Mg, Ca, Sr, Ba, or Ra, etc., but is not limited thereto.

[0186] The p-type charge generation material according to the present application can include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazoyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene) polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, a carbazole ring-containing compound represented by Formula 1 of the present application, and the like, but is not limited thereto.

[0187] The method for preparing each layer thin film of the organic electroluminescent device according to the present application is not particularly limited, and can employ a vacuum evaporation method, a sputtering method, a spin coating method, a spray coating method, a screen printing method, a laser transfer method, and the like, but is not limited thereto. The film thickness of each layer is not particularly limited, and in general, if the film thickness is too thin, defects such as pinholes are easily generated, and on the contrary, if the film thickness is too thick, a high driving voltage is required and the efficiency is deteriorated, and thus it is generally 5 nm to 10 μm, and more preferably 10 nm to 0.2 μm.

[0188] The organic electroluminescent device according to the present application is mainly applied to the field of information display technology, and is widely used in various information displays in the field of information display, such as tablet computers, televisions, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable devices, lighting devices, and the like.

[0189] Synthetic Examples

[0190] Raw materials and reagents: The raw materials or reagents used in the following synthetic examples according to the present application are not particularly limited, and can be commercially available products or prepared by a preparation method well known to those skilled in the art. The raw materials and reagents used in the present application are all reagent grade.

[0191] Instrument: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube type organic elemental analyzer (Elementar, Germany).

[0192] The preparation method of the carbazole ring-containing compound of structural formula 1 of the present application is not particularly limited, and a conventional method well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc., for example, the carbazole ring-containing compound of structural formula 1 of the present application can be prepared by using the synthetic route shown below.

[0193] 1. When the group shown in formula 1-b is contained in Ar1:

[0194] ① When L1is selected from a single bond:

[0195]

[0196] ② When L1is not selected from a single bond:

[0197]

[0198]

[0199] 2. When the group shown in formula 1-b is contained in L1:

[0200]

[0201] 3. When the group shown in formula 1-b is contained in

[0202]

[0203] X1, X2, X3are independently selected from any one of I, Br, and Cl;

[0204] The above substituent can be bonded by a method known in the art, and the type and position of the substituent or the number of the substituent can be changed according to the technique known in the art.

[0205] Preparation and characterization of compounds

[0206] Explanation of raw materials, reagents, and characterization equipment:

[0207] The raw materials and reagents used in the following examples of the present application are not particularly limited, and can be commercially available products or prepared by a method well known to those skilled in the art.

[0208] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the United Kingdom, and chloroform is used as the solvent;

[0209] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany, and the sample mass is 5-10 mg. ​

[0210] Synthesis Example 1: Preparation of Intermediate a-812

[0211]

[0212] To a reaction flask was added a-812 (35.45 g, 140.00 mmol), bis(pinacolato)diboron (35.91 g, 141.40 mmol), KOAc (27.48 g, 280.00 mmol) dissolved in 700 mL of 1,4-dioxane, Pd(PPh3)4(3.24 g, 2.80 mmol) was added with stirring, and the mixture was heated to reflux for 5.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and the resulting solid was recrystallized from toluene / ethanol = 8:1 to obtain intermediate a-812 (32.37 g, yield 77%); HPLC purity ≧ 99.88%. Mass spectrum m / z: 300.2250 (theoretical value: 300.2261).

[0213] Other intermediates required for the present application were synthesized according to the above synthesis method, and the relevant starting materials are shown in Table 1:

[0214] Table 1:

[0215]

[0216] Synthesis Example 2: Preparation of Compound 4

[0217]

[0218] Preparation of Intermediate A-4

[0219] To a reaction flask was added a-4 (17.01 g, 105.00 mmol), b-4 (29.56 g, 105.00 mmol), K2CO3(29.02 g, 210.00 mmol) dissolved in 600 mL of toluene / ethanol / water (2:1:1), Pd(dppf)Cl2(1.54 g, 2.10 mmol) was added with stirring, and the mixture was heated to reflux for 4.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and the resulting solid was recrystallized from toluene / ethanol = 8:1 to obtain intermediate A-4 (26.78 g, yield 80%); HPLC purity ≧ 99.89%. Mass spectrum m / z: 318.0801 (theoretical value: 318.0811).

[0220] Preparation of Intermediate B-4

[0221] To a reaction flask was added A-4 (25.50 g, 80.00 mmol), bis(pinacolato)diboron (20.52 g, 80.80 mmol), KOAc (15.70 g, 160.00 mmol) dissolved in 450 ml of 1,4-dioxane, Pd(PPh3)4 (1.85 g, 1.60 mmol) was added under stirring and the mixture was heated to reflux for 5 h. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water and the solid obtained was recrystallized with toluene / ethanol = 9:1 to obtain intermediate B-4 (25.60 g, yield 78 %); HPLC purity > 99.84 %. Mass m / z: 410.2061 (theoretical value: 410.2053).

[0222] Preparation of intermediate C-4

[0223] To a reaction flask was added B-4 (24.62 g, 60 mmol), e-4 (11.49 g, 60.00 mmol), K2CO3 (16.59 g, 120.00 mmol) dissolved in 300 ml of toluene / ethanol / water (2:1:1), Pd(dppf)Cl2 (0.88 g, 1.20 mmol) was added under stirring and the mixture was heated to reflux for 5.5 h. After completion of the reaction, the reaction mixture was cooled to room temperature, filtered, washed with distilled water and the solid obtained was recrystallized with toluene / ethanol = 8:1 to obtain intermediate C-4 (17.77 g, yield 75 %); HPLC purity > 99.88 %. Mass m / z: 394.1138 (theoretical value: 394.1124).

[0224] Preparation of compound 4

[0225] To a reaction flask was added c-4 (10.29 g, 40.00 mmol), C-4 (15.80 g, 40.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol) dissolved in 180 ml of toluene, Pd2(dba)3 (0.37 g, 0.40 mmol), X-Phos (0.38 g, 0.80 mmol) was added under stirring and the mixture was heated to reflux for 6.5 h. After completion of the reaction, it was cooled to room temperature, water was added and extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. Recrystallization was carried out with toluene to obtain compound 4 (17.73 g, yield 72 %). HPLC solid purity > 99.95 %. Mass m / z: 615.2188 (theoretical value: 615.2198). Theoretical elemental content (%) C 45 H 29NO2: C, 87.78; H, 4.75; N, 2.27. Found: C, 87.74; H, 4.77; N, 2.30.

[0226] Synthesis Example 3: Preparation of compound 26

[0227]

[0228] According to the preparation method of synthesis example 2, b-4 was replaced by equimolar b-26, c-4 was replaced by equimolar c-26, and e-4 was replaced by equimolar e-26 to obtain compound 26 (14.66 g) with an HPLC solid purity of > 99.93%. Mass spectrum m / z: 615.2175 (theoretical value: 615.2198). Theoretical elemental content (%) C 45 H 29 NO2: C, 87.78; H, 4.75; N, 2.27. Found: C, 87.74; H, 4.77; N, 2.30.

[0229] Synthesis Example 4: Preparation of compound 37

[0230]

[0231] Preparation of intermediate A-37

[0232] Under nitrogen protection, a-26 (10.53 g, 65 mmol), b-4 (18.30 g, 65 mmol), K2CO3 (17.97 g, 130.00 mmol) were dissolved in 350 ml of toluene / ethanol / water (2:1:1), and Pd(dppf)Cl2 (0.95 g, 1.3 mmol) was added under stirring. The mixture solution was heated to reflux for 4 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 8:1 to obtain intermediate A-37 (16.58 g, yield 80%); HPLC purity > 99.89%. Mass spectrum m / z: 318.0824 (theoretical value: 318.0811).

[0233] Preparation of compound 37

[0234] To a reaction flask was added c-37 (16.08 g, 45.00 mmol), A-37 (14.35 g, 45.00 mmol), sodium tert-butoxide (6.49 g, 67.50 mmol) dissolved in 200 mL of toluene under nitrogen, and Pd2(dba)3(0.41 g, 0.45 mmol), X-Phos (0.43 g, 0.90 mmol) was added with stirring. The mixture was heated to reflux for 5.5 h. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The compound 37 (18.21 g, 75% yield) was obtained by recrystallization from toluene. The solid purity was > 99.97% by HPLC. Mass spectrum m / z: 539.1893 (calcd: 539.1885). Theoretical elemental content (%) C 39 H 29 NO2: C, 86.80; H, 4.67; N, 2.60. Found elemental content (%): C, 86.78; H, 4.73; N, 2.54.

[0235] Synthesis Example 5: Preparation of compound 49

[0236]

[0237] According to the preparation method of synthesis example 2, c-4 was replaced with an equal molar amount of c-49, and e-4 was replaced with an equal molar amount of e-49, to obtain compound 49 (20.62 g), which had a solid purity of > 99.93% by HPLC. Mass spectrum m / z: 715.2521 (calcd: 715.2511). Theoretical elemental content (%) C 53 H 33 NO2: C, 88.93; H, 4.65; N, 1.96. Found elemental content (%): C, 88.95; H, 4.68; N, 1.92.

[0238] Synthesis Example 6: Preparation of compound 60

[0239]

[0240] According to the preparation method of synthesis example 4, a-26 was replaced with an equal molar amount of a-60, and c-37 was replaced with an equal molar amount of c-26, to obtain compound 60 (21.06 g), which had a solid purity of > 99.93% by HPLC. Mass spectrum m / z: 615.2182 (calcd: 615.2198). Theoretical elemental content (%) C 45 H 29NO2: C, 87.78; H, 4.75; N, 2.27. Found (mass %): C, 87.76; H, 4.74; N, 2.30.

[0241] Synthesis Example 7: Preparation of compound 77

[0242]

[0243] According to the preparation method of synthesis example 2, replace e-4 with equimolar e-77 to obtain compound 77 (17.49 g), with solid purity of > 99.94% detected by HPLC. Mass spectrum m / z: 671.2812 (theoretical value: 671.2824). Theoretical elemental content (%) C 49 H 37 NO2: C, 87.60; H, 5.55; N, 2.08. Found (mass %): C, 87.58; H, 5.52; N, 2.10.

[0244] Synthesis Example 8: Preparation of compound 80

[0245]

[0246]

[0247] According to the preparation method of synthesis example 2, replace b-4 with equimolar b-80 and c-4 with equimolar c-80 to obtain compound 80 (19.47 g), with solid purity of > 99.94% detected by HPLC. Mass spectrum m / z: 657.2677 (theoretical value: 657.2668). Theoretical elemental content (%) C 48 H 35 NO2: C, 87.64; H, 5.36; N, 2.13. Found (mass %): C, 87.60; H, 5.40; N, 2.09.

[0248] Synthesis Example 9: Preparation of compound 133

[0249]

[0250] According to the preparation method of synthesis example 2, replace e-4 with equimolar e-133 and c-4 with equimolar c-133 to obtain compound 133 (19.17 g), with solid purity of > 99.91% detected by HPLC. Mass spectrum m / z: 665.2341 (theoretical value: 665.2355). Theoretical elemental content (%) C 49 H 31NO2: C, 88.40; H, 4.69; N, 2.10. Found (mass %): C, 88.38; H, 4.72; N, 2.14.

[0251] Synthesis Example 10: Preparation of compound 302

[0252]

[0253] According to the preparation method of synthesis example 2, a-4 was replaced with equimolar a-26, b-4 was replaced with equimolar b-302, e-4 was replaced with equimolar e-302, and c-4 was replaced with equimolar c-302 to obtain compound 302 (29.20 g) with an HPLC solid purity of ≧99.91%. Mass spectrum m / z: 708.2221 (theoretical value: 708.2235). Theoretical elemental content (%) C 50 H 32 N2OS: C, 84.72; H, 4.55; N, 3.95. Found (mass %): C, 84.76; H, 4.52; N, 3.96.

[0254] Synthesis Example 11: Preparation of compound 380

[0255]

[0256]

[0257] Preparation of intermediate A-380

[0258] Under nitrogen protection, a-4 (16.20 g, 100.00 mmol), e-380 (31.73 g, 100.00 mmol), K2CO3 (27.64 g, 200.00 mmol) were dissolved in 550 ml of toluene / ethanol / water (2:1:1), and Pd(dppf)Cl2 (1.46 g, 2.00 mmol) was added under stirring. The mixture solution was heated to reflux for 3.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 9:1 to obtain intermediate A-380 (23.07 g, yield 75%); HPLC purity ≧99.89%. Mass spectrum m / z: 305.9818 (theoretical value: 305.9811).

[0259] Preparation of intermediate B-380

[0260] To a reaction flask was added A-380 (21.53 g, 70.00 mmol), b-380 (15.97 g, 70.00 mmol), K2CO3 (19.35 g, 140.00 mmol) dissolved in 400 mL of toluene / ethanol / water (2:1:1), Pd(dppf)Cl2 (1.02 g, 1.40 mmol) was added under stirring and the mixture was heated to reflux for 5.5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water and the resulting solid was recrystallized with toluene / ethanol = 8:1 to obtain intermediate B-380 (20.56 g, yield 72%); HPLC purity > 99.73%. Mass spectrum m / z: 410.0879 (theoretical value: 410.0896).

[0261] Preparation of compound 380

[0262] To a reaction flask was added c-4 (10.29 g, 45.00 mmol), B-380 (15.80 g, 45.00 mmol), sodium tert-butoxide (5.77 g, 67.50 mmol) dissolved in 180 mL of toluene, Pd2(dba)3 (0.37 g, 0.45 mmol), X-Phos (0.38 g, 0.90 mmol) was added under stirring and the mixture was heated to reflux for 6.5 h. After the reaction was completed, it was cooled to room temperature, water was added and extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. Recrystallization was performed with toluene to obtain compound 380 (19.90 g, 70%). HPLC solid purity > 99.98%. Mass spectrum m / z: 631.1983 (theoretical value: 631.1970). Theoretical elemental content (%) C 45 H 29 NOS: C, 85.55; H, 4.63; N, 2.22, Found elemental content (%): C, 85.52; H, 4.68; N, 2.20.

[0263] Synthesis example 12: Preparation of compound 393

[0264]

[0265] According to the preparation method of synthesis example 11, b-380 was replaced with an equimolar amount of b-393 to obtain compound 393 (19.95 g) with HPLC solid purity > 99.94%. Mass spectrum m / z: 638.2425 (theoretical value: 638.2409). Theoretical elemental content (%) C 45 H 22D7NOS: C, 84.61; H, 5.68; N, 2.19. Found (%): C, 84.63; H, 5.66; N, 2.20.

[0266] Synthesis Example 13: Preparation of compound 485

[0267]

[0268] According to the preparation method of synthesis example 11, a-4 was replaced with equimolar a-26, e-380 was replaced with equimolar e-485, and c-4 was replaced with equimolar c-485 to obtain compound 485 (21.02 g) with a solid purity of > 99.96% by HPLC. Mass spectrum m / z: 634.2146 (theoretical value: 634.2158). Theoretical elemental content (%) C 45 H 26 D3NOS: C, 85.14; H, 5.08; N, 2.21. Found (%): C, 85.11; H, 5.10; N, 2.22.

[0269] Synthesis Example 14: Preparation of compound 488

[0270]

[0271] Preparation of intermediate A-488

[0272] Under nitrogen protection, a-26 (12.15 g, 75.00 mmol), e-488 (25.21 g, 75.00 mmol), K2CO3 (20.73 g, 150.00 mmol) were dissolved in 550 ml of toluene / ethanol / water (2:1:1), and Pd(dppf)Cl2 (1.1 g, 1.50 mmol) was added under stirring. The mixture solution of the above reactants was heated to reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, suction filtered, washed with distilled water, and then the obtained solid was recrystallized with toluene / ethanol = 9:1 to obtain intermediate A-488 (22.41 g, yield 80%); HPLC purity > 99.91%. Mass spectrum m / z: 373.1479 (theoretical value: 373.1467).

[0273] Preparation of compound 488

[0274] To a reaction flask was added c-488 (16.21 g, 55.00 mmol), A-488 (20.54 g, 55.00 mmol), sodium tert-butoxide (7.93 g, 82.5 mmol) dissolved in 250 mL of toluene under nitrogen, and Pd2(dba)3(0.50 g, 0.55 mmol), X-Phos (0.52 g, 1.10 mmol) was added with stirring. The mixture was heated to reflux for 6 h. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The compound 380 (24.32 g, 70%) was obtained by recrystallization from toluene. The solid purity was > 99.93% by HPLC. Mass spectrum m / z: 631.1981 (calcd: 631.1970). Theoretical elemental content (%) C 45 H 29 NOS: C, 85.55; H, 4.63; N, 2.22. Found elemental content (%) C, 85.51; H, 4.60; N, 2.25.

[0275] Synthesis Example 15: Preparation of compound 511

[0276]

[0277] According to the preparation method of synthesis example 2, b-4 was replaced with an equimolar amount of b-511, and e-4 was replaced with an equimolar amount of e-511 to obtain compound 511 (19.99 g). The solid purity was > 99.90% by HPLC. Mass spectrum m / z: 713.3101 (calcd: 713.3114). Theoretical elemental content (%) C 51 H 43 NOSi: C, 85.79; H, 6.07; N, 1.96. Found elemental content (%) C, 85.81; H, 6.04; N, 1.97.

[0278] Synthesis Example 16: Preparation of compound 601

[0279]

[0280] According to the preparation method of synthesis example 11, a-4 was replaced with an equimolar amount of a-26, and b-380 was replaced with an equimolar amount of b-601 to obtain compound 601 (26.08 g). The solid purity was > 99.97% by HPLC. Mass spectrum m / z: 793.3357 (calcd: 793.3345). Theoretical elemental content (%) C 60 H 43NO: C, 90.76; H, 5.46; N, 1.76. Found (%): C, 90.77; H, 5.50; N, 1.74.

[0281] Synthesis Example 17: Preparation of compound 717

[0282]

[0283] According to the preparation method of synthesis example 2, replace a-4 with equimolar a-26, c-4 with equimolar c-717, to obtain compound 717 (18.45 g), solid purity > 99.94% detected by HPLC. Mass spectrum m / z: 631.1986 (theoretical value: 631.1970). Theoretical elemental content (%) C 45 H 29 NOS: C, 85.55; H, 4.63; N, 2.22. Found (%): C, 85.58; H, 4.60; N, 2.17.

[0284] Synthesis Example 18: Preparation of compound 737

[0285]

[0286]

[0287] According to the preparation method of synthesis example 2, replace a-4 with equimolar a-26, b-4 with equimolar b-26, c-4 with equimolar c-717, e-4 with equimolar e-26, to obtain compound 737 (17.94 g), solid purity > 99.98% detected by HPLC. Mass spectrum m / z: 631.1957 (theoretical value: 631.1970). Theoretical elemental content (%) C 45 H 29 NOS: C, 85.55; H, 4.63; N, 2.22. Found (%): C, 85.58; H, 4.60; N, 2.17.

[0288] Synthesis Example 19: Preparation of compound 773

[0289]

[0290] According to the preparation method of synthesis example 2, replace b-4 with equimolar b-773, c-4 with equimolar c-717, e-4 with equimolar e-773, to obtain compound 773 (20.95 g), solid purity > 99.97% detected by HPLC. Mass spectrum m / z: 707.2299 (theoretical value: 707.2283). Theoretical elemental content (%) C51 H 33 NOS: C, 86.53; H, 4.70; N, 1.98. Found (%): C, 85.56; H, 4.68; N, 1.94.

[0291] Synthesis Example 20: Preparation of compound 786

[0292]

[0293] According to the preparation method of synthesis example 2, replace a-4 with equimolar a-786, c-4 with equimolar c-717, and e-4 with equimolar e-786 to obtain compound 786 (20.85 g) with solid purity > 99.97% detected by HPLC. Mass spectrum m / z: 685.2455 (theoretical value: 685.2439). Theoretical elemental content (%) C 49 H 35 NOS: C, 85.81; H, 5.14; N, 2.04. Found (%): C, 85.79; H, 5.17; N, 2.09.

[0294] Synthesis Example 21: Preparation of compound 787

[0295]

[0296] According to the preparation method of synthesis example 2, replace a-4 with equimolar a-787, c-4 with equimolar c-717, and e-4 with equimolar e-787 to obtain compound 787 (20.26 g) with solid purity > 99.94% detected by HPLC. Mass spectrum m / z: 657.1779 (theoretical value: 657.1762). Theoretical elemental content (%) C 46 H 27 NOS: C, 83.99; H, 4.14; N, 2.13. Found (%): C, 83.95; H, 4.16; N, 2.16.

[0297] Synthesis Example 22: Preparation of compound 800

[0298]

[0299] According to the preparation method of synthesis example 2, replace c-4 with equimolar c-717, and e-4 with equimolar e-800 to obtain compound 800 (17.04 g) with solid purity > 99.97% detected by HPLC. Mass spectrum m / z: 635.2235 (theoretical value: 635.2221). Theoretical elemental content (%) C 45 H 25D4NOS: C, 85.01; H, 5.23; N, 2.20. Found (%): C, 85.05; H, 5.25; N, 2.17.

[0300] Synthesis Example 24: Preparation of Compound 812

[0301]

[0302] According to the preparation method of Synthesis Example 2, b-4 was replaced with an equivalent mole of b-801, and c-4 was replaced with an equivalent mole of c-717 to obtain Compound 801 (16.58 g) with a solid purity of > 99.96% detected by HPLC. Mass spectrum m / z: 637.2358 (theoretical value: 637.2346). Theoretical elemental content (%) C 45 H 25 D4NOS: C, 85.01; H, 5.23; N, 2.20. Found (%): C, 85.05; H, 5.25; N, 2.17.

[0303] Synthesis Example 24: Preparation of Compound 812

[0304]

[0305] According to the preparation method of Synthesis Example 2, a-4 was replaced with an equivalent mole of a-812, and c-4 was replaced with an equivalent mole of c-717 to obtain Compound 812 (20.36 g) with a solid purity of > 99.95% detected by HPLC. Mass spectrum m / z: 687.2585 (theoretical value: 687.2596). Theoretical elemental content (%) C 49 H 37 NOS: C, 85.56; H, 5.42; N, 2.04. Found (%): C, 85.61; H, 5.45; N, 2.00.

[0306] Synthesis Example 25: Preparation of Compound 837

[0307]

[0308] According to the preparation method of Synthesis Example 2, a-4 was replaced with an equivalent mole of a-837, and c-4 was replaced with an equivalent mole of c-837 to obtain Compound 837 (20.67 g) with a solid purity of > 99.96% detected by HPLC. Mass spectrum m / z: 707.2299 (theoretical value: 707.2283). Theoretical elemental content (%) C 51 H 33 NOS: C, 86.53; H, 4.70; N, 1.98. Found (%): C, 85.58; H, 4.69; N, 1.94.

[0309] Synthesis Example 26: Preparation of compound 846

[0310]

[0311] According to the preparation method of synthesis example 2, replace a-4 with an equal mole of a-26, replace c-4 with an equal mole of c-717, and replace e-4 with an equal mole of e-846 to obtain compound 846 (21.80 g) with a solid purity of > 99.91% as detected by HPLC. Mass spectrum m / z: 707.2270 (theoretical value: 707.2283). Theoretical elemental content (%) C 51 H 33 NOS: C, 86.53; H, 4.70; N, 1.98. Actual elemental content (%) C, 85.59; H, 4.68; N, 1.94.

[0312] Synthesis Example 27: Preparation of compound 854

[0313]

[0314] According to the preparation method of synthesis example 2, replace c-4 with an equal mole of c-717, and replace e-4 with an equal mole of e-854 to obtain compound 854 (21.14 g) with a solid purity of > 99.96% as detected by HPLC. Mass spectrum m / z: 765.3076 (theoretical value: 765.3065). Theoretical elemental content (%) C 55 H 43 NOS: C, 86.24; H, 5.66; N, 1.83. Actual elemental content (%) C, 86.29; H, 5.62; N, 1.81.

[0315] Synthesis Example 28: Preparation of compound 859

[0316]

[0317] According to the preparation method of synthesis example 2, replace c-4 with an equal mole of c-717, and replace e-4 with an equal mole of e-859 to obtain compound 859 (21.39 g) with a solid purity of > 99.95% as detected by HPLC. Mass spectrum m / z: 763.2921 (theoretical value: 763.2909). Theoretical elemental content (%) C 55 H 41 NOS: C, 86.47; H, 5.41; N, 1.83. Actual elemental content (%) C, 86.50; H, 5.37; N, 1.80.

[0318] Synthesis Example 29: Preparation of compound 880

[0319]

[0320] According to the preparation method of Synthetic Example 2, replace a-4 with equimolar a-880, and replace c-4 with equimolar c-717 to obtain compound 880 (17.89 g) with solid purity > 99.94% detected by HPLC. Mass spectrum m / z: 629.1830 (theoretical value: 629.1813). Theoretical elemental content (%) C 45 H 27 NOS: C, 85.82; H, 4.32; N, 2.22. Actual elemental content (%) : C, 86.79; H, 4.35; N, 2.24.

[0321] Synthesis Example 30: Preparation of compound 920

[0322]

[0323] According to the preparation method of Synthetic Example 11, replace b-380 with equimolar b-920, and replace c-4 with equimolar c-717 to obtain compound 920 (24.39 g) with solid purity > 99.96% detected by HPLC. Mass spectrum m / z: 703.2378 (theoretical value: 703.2365). Theoretical elemental content (%) C 48 H 37 NOS: C, 85.82; H, 4.32; N, 2.22. Actual elemental content (%) : C, 86.79; H, 4.35; N, 2.24.

[0324] Synthesis Example 31: Preparation of compound 938

[0325]

[0326] According to the preparation method of Synthetic Example 11, replace b-380 with equimolar b-938, and replace c-4 with equimolar c-717 to obtain compound 938 (23.89 g) with solid purity > 99.92% detected by HPLC. Mass spectrum m / z: 707.2297 (theoretical value: 707.2283). Theoretical elemental content (%) C 51 H 33 NOS: C, 85.82; H, 4.32; N, 2.22. Actual elemental content (%) : C, 86.79; H, 4.35; N, 2.24.

[0327] Synthesis Example 32: Preparation of compound 963

[0328]

[0329] According to the preparation method of Synthesis Example 11, replace a-4 with an equal mole of a-26, b-380 with an equal mole of b-963, and c-4 with an equal mole of c-963 to obtain compound 963 (21.86 g) with a solid purity of > 99.98% as determined by HPLC. Mass spectrum m / z: 735.2550 (theoretical value: 735.2534). Theoretical elemental content (%) C 53 H 29 D4NOS: C, 86.50; H, 5.07; N, 1.90. Actual elemental content (%) C, 86.45; H, 5.05; N, 1.93.

[0330] Synthesis Example 33: Preparation of compound 1031

[0331]

[0332] According to the preparation method of Synthesis Example 2, replace a-4 with an equal mole of a-1031 and c-4 with an equal mole of c-1031 to obtain compound 1031 (21.95 g) with a solid purity of > 99.91% as determined by HPLC. Mass spectrum m / z: 870.3735 (theoretical value: 870.3723). Theoretical elemental content (%) C 63 H 46 D3NOS: C, 86.86; H, 6.02; N, 1.61. Actual elemental content (%) C, 86.83; H, 6.04; N, 1.65.

[0333] Synthesis Example 34: Preparation of compound 1073

[0334]

[0335] According to the preparation method of Synthesis Example 11, replace a-4 with an equal mole of a-1073, b-380 with an equal mole of b-1073, c-4 with an equal mole of c-1073, and e-380 with an equal mole of e-1073 to obtain compound 1073 (23.48 g) with a solid purity of > 99.95% as determined by HPLC. Mass spectrum m / z: 704.2333 (theoretical value: 704.2318). Theoretical elemental content (%) C 47 H 36 N2OSSi: C, 80.08; H, 5.15; N, 3.97. Actual elemental content (%) C, 80.12; H, 5.19; N, 3.93.

[0336] Synthesis Example 35: Preparation of compound 1163

[0337]

[0338] According to the preparation method of synthesis example 2, replace c-4 with equimolar of c-717, e-4 with equimolar of e-1163 to obtain compound 1163 (19.39 g), solid purity > 99.96% detected by HPLC. Mass spectrum m / z: 712.2584 (theoretical value: 712.2597). Theoretical elemental content (%) C 51 H 28 D5NOS: C, 85.92; H, 5.37; N, 1.96. Actual elemental content (%) : C, 85.94; H, 5.35; N, 1.99.

[0339] Synthesis example 36: preparation of compound 1213

[0340]

[0341] According to the preparation method of synthesis example 11, replace a-4 with equimolar of a-1213, b-380 with equimolar of b-1213, c-4 with equimolar of c-1213 to obtain compound 1213 (22.61 g), solid purity > 99.96% detected by HPLC. Mass spectrum m / z: 669.1596 (theoretical value: 669.1585). Theoretical elemental content (%) C 47 H 37 NS2: C, 84.27; H, 4.06; N, 2.09. Actual elemental content (%) : C, 84.28; H, 4.03; N, 2.13.

[0342] Synthesis example 37: preparation of compound 1407

[0343]

[0344] According to the preparation method of synthesis example 11, replace a-4 with equimolar of a-26, b-380 with equimolar of b-1407, c-4 with equimolar of c-717 to obtain compound 1407 (21.99 g), solid purity > 99.97% detected by HPLC. Mass spectrum m / z: 697.2819 (theoretical value: 697.2803). Theoretical elemental content (%) C 51 H 39 NS: C, 87.77; H, 5.63; N, 2.01. Actual elemental content (%) : C, 87.73; H, 5.66; N, 2.03.

[0345] Synthesis example 38: preparation of compound 1507

[0346]

[0347] According to the preparation method of synthesis example 11, b-380 was replaced with equimolar b-1507, c-4 was replaced with equimolar c-717, and e-380 was replaced with equimolar e-1507 to obtain compound 1507 (23.22 g) with solid purity > 99.92% detected by HPLC. Mass spectrum m / z: 706.2457 (theoretical value: 706.2443). Theoretical elemental content (%) C 51 H 34 N2S: C, 86.65; H, 4.85; N, 3.96. Actual elemental content (%) : C, 86.61; H, 4.88; N, 3.98.

[0348] Synthesis example 39: preparation of compound 1779

[0349]

[0350] According to the preparation method of synthesis example 11, b-380 was replaced with equimolar b-1779, and c-4 was replaced with equimolar c-1779 to obtain compound 1779 (25.95 g) with solid purity > 99.93% detected by HPLC. Mass spectrum m / z: 789.3387 (theoretical value: 789.3396). Theoretical elemental content (%) C 61 H 43 N: C, 92.74; H, 5.49; N, 1.77. Actual elemental content (%) : C, 92.70; H, 5.50; N, 1.80.

[0351] Synthesis example 40: preparation of compound 1805

[0352]

[0353] According to the preparation method of synthesis example 2, b-4 was replaced with equimolar b-1805, and c-4 was replaced with equimolar c-1805 to obtain compound 1805 (19.39 g) with solid purity > 99.91% detected by HPLC. Mass spectrum m / z: 808.3827 (theoretical value: 808.3817). Theoretical elemental content (%) C 61 H 48 N2: C, 90.56; H, 5.98; N, 3.46. Actual elemental content (%) : C, 90.53; H, 5.96; N, 3.50.

[0354] Device example

[0355] In the present application, the ITO glass substrate is cleaned by 5% glass cleaning solution for 2 times, 20 minutes each time, and then cleaned by deionized water for 2 times, 10 minutes each time. The substrate is cleaned by acetone and isopropyl alcohol for 20 minutes each time, and then dried at 120°C. The organic materials are all sublimed, and the purity is above 99.99%.

[0356] The test software, computer, K2400 digital source meter produced by Keithley Company of USA, and PR788 spectral scanning luminance meter produced by PhotoResearch Company of USA are combined into an integrated IVL test system to test the driving voltage, luminous efficiency, CIE color coordinate, and lifetime of the organic electroluminescent device. The M6000 OLED lifetime test system produced by McScience Company is used to test the lifetime of the device. The test environment is atmospheric environment, and the temperature is room temperature.

[0357] The device is prepared by using a vacuum evaporation system, and is continuously prepared by continuous evaporation under uninterrupted vacuum condition. The materials are placed in different quartz crucible evaporation sources, and the temperature of the evaporation source can be controlled individually. The thermal evaporation rate of the organic material is generally set at 0.1 nm / s, and the evaporation rate of the electrode metal is 0.4-0.6 nm / s. The treated glass substrate is placed into the OLED vacuum film coating machine, and the vacuum degree of the system should be maintained below 5x10 -5 Pa during the thin film preparation process. The organic layer and the metal electrode are evaporated by replacing the mask plate, the evaporation rate is detected by using the SQM160 quartz crystal film thickness detector of Inficon, and the film thickness is detected by using the quartz crystal oscillator.

[0358] Example 1: Preparation of organic electroluminescent device 1

[0359] The ITO / Ag / ITO is used as the anode on the glass substrate; the HT-1:HI-1 (mass ratio 97:3 mixed) is vacuum evaporated on the anode to form a hole injection layer with a thickness of 20 nm; the HT-1 is vacuum evaporated on the hole injection layer to form a hole transport layer with a thickness of 120 nm; the compound 4:H-1:D-1 (mass ratio 46:46:4 mixed) is vacuum evaporated on the hole transport layer to form a light-emitting layer with a thickness of 35 nm; the HB-1 is vacuum evaporated on the light-emitting layer to form a hole blocking layer with a thickness of 5 nm; the ET-1:LiQ (mass ratio 1:1 mixed) is vacuum evaporated on the hole blocking layer to form an electron transport layer with a thickness of 25 nm; the LiF is vacuum evaporated on the electron transport layer to form an electron injection layer with a thickness of 1.0 nm; the Mg and Ag (mass ratio 1:9) are vacuum evaporated on the electron injection layer to form a cathode with a thickness of 10 nm; and the CP-1 is evaporated on the cathode to form a cover layer with a thickness of 80 nm.

[0360] Examples 2-30: Preparation of organic electroluminescent devices 2-30

[0361] The compound 4 in the light-emitting layer of Example 1 is replaced by compound 26, compound 37, compound 60, compound 77, compound 80, compound 133, compound 380, compound 393, compound 485, compound 488, compound 717, compound 737, compound 773, compound 786, compound 787, compound 800, compound 801, compound 812, compound 837, compound 846, compound 854, compound 859, compound 880, compound 920, compound 938, compound 963, compound 1031, compound 1163, compound 1507, respectively, and other steps are the same, to obtain organic electroluminescent devices 2-30.

[0362] Preparation of Comparative Organic Electroluminescent Devices 1-3

[0363] The compound 4 in the light-emitting layer of Example 1 is replaced by R-1, R-2, R-3, respectively, and other steps are the same, to obtain comparative organic electroluminescent devices 1-3.

[0364]

[0365] The luminescent property test results of the organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-3 of the present application are shown in Table 1.

[0366] Table 2 Luminescent property test data of organic electroluminescent devices

[0367]

[0368]

[0369] Note: T95 refers to the time taken for the device brightness to decay to 95% under a current density of 10 mA / cm 2 ; and

[0370] From the results in Table 1, it can be seen that, compared with Comparative Examples 1-3, the luminescent efficiency and service life of the device are greatly improved when the compound containing a carbazole ring of the present application is applied to the light-emitting layer of the organic electroluminescent device, and the compound of the present application is a good light-emitting layer material.

[0371] Example 31: Preparation of Organic Electroluminescent Device 31

[0372] On a glass substrate, ITO / Ag / ITO was used as an anode; 20 nm of HT-1:HI-1 (mass ratio 97:3 mixed) was vacuum evaporated on the anode to form a hole injection layer; 115 nm of HT-1 was vacuum evaporated on the hole injection layer to form a hole transport layer; 5 nm of EB-1 was vacuum evaporated on the hole transport layer to form an electron blocking layer; 35 nm of compound 4:D-2 (mass ratio 76:24 mixed) was vacuum evaporated on the electron blocking layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mass ratio 1:1 mixed) was vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF was vacuum evaporated on the electron transport layer to form an electron injection layer; 10 nm of Mg and Ag (mass ratio 1:9) was vacuum evaporated on the electron injection layer to form a cathode, and 80 nm of CP-1 was evaporated on the cathode to form a cover layer.

[0373] Examples 32-60: Preparation of organic electroluminescent devices 32-60

[0374] Compound 4 in the light-emitting layer of Example 31 was replaced by compound 26, compound 49, compound 60, compound 77, compound 80, compound 302, compound 380, compound 393, compound 485, compound 488, compound 511, compound 601, compound 717, compound 773, compound 800, compound 801, compound 812, compound 837, compound 846, compound 854, compound 859, compound 880, compound 938, compound 1163, compound 1213, compound 1407, compound 1507, compound 1779, compound 1805, respectively, and the other steps were the same to obtain organic electroluminescent devices 32-60.

[0375] Comparative Examples 4-6: Preparation of comparative organic electroluminescent devices 4-6

[0376] Compound 4 in the light-emitting layer of Example 31 was replaced by R-4, R-5, R-2, respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4-6.

[0377]

[0378] The luminescent property test results of the organic electroluminescent devices prepared in Examples 31-60 and Comparative Examples 4-6 of the present application are shown in Table 2.

[0379] Table 2 Luminescent property test data of organic electroluminescent devices

[0380]

[0381]

[0382] Note: T95 refers to the time taken for the device brightness to decay to 95% of the initial value at a current density of 10 mA / cm 2 in the case of a current density of 10 mA / cm

[0383] As can be seen from the results in Table 2, when the compound containing the carbazole ring according to the present application is applied to the light-emitting layer of the organic electroluminescent device, the luminous efficiency and service life of the device are improved compared with Comparative Examples 4 to 6, indicating that the compound according to the present application is a good light-emitting layer material.

[0384] Example 61: Preparation of an organic electroluminescent device 61

[0385] An ITO / Ag / ITO was used as the anode on a glass substrate; a 20 nm thick hole injection layer of HT-1:HI-1 (mass ratio 97:3) was vacuum-deposited on the anode; a 115 nm thick hole transport layer of HT-1 was vacuum-deposited on the hole injection layer; a 5 nm thick electron blocking layer of EB-1 was vacuum-deposited on the hole transport layer; a 35 nm thick light-emitting layer of compound 4:D-2:D-4 (mass ratio 79:20:1) was vacuum-deposited on the electron blocking layer; a 5 nm thick hole blocking layer of HB-1 was vacuum-deposited on the light-emitting layer; a 25 nm thick electron transport layer of ET-2:LiQ (mass ratio 1:1) was vacuum-deposited on the hole blocking layer; a 1.0 nm thick electron injection layer of LiF was vacuum-deposited on the electron transport layer; a 10 nm thick cathode of Mg and Ag (mass ratio 1:9) was vacuum-deposited on the electron injection layer, and a 80 nm thick cover layer of CP-1 was vacuum-deposited on the cathode.

[0386] Examples 62 to 80: Preparation of organic electroluminescent devices 62 to 80

[0387] Compound 4 in the light-emitting layer of Example 61 was replaced by compound 26, compound 60, compound 77, compound 80, compound 380, compound 393, compound 485, compound 717, compound 800, compound 801, compound 812, compound 846, compound 854, compound 859, compound 880, compound 938, compound 1073, compound 1163, and compound 1507, respectively, and the other steps were the same to obtain organic electroluminescent devices 62 to 80.

[0388] Comparative Examples 7 to 8: Preparation of comparative organic electroluminescent devices 7 to 8

[0389] Compound 4 in the light-emitting layer of Example 61 was replaced by R-4 and R-5, respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 7 to 8.

[0390]

[0391] The results of the luminescent property test of the organic electroluminescent devices prepared in Examples 61-80 and Comparative Examples 7-8 are shown in Table 3.

[0392] Table 3 Luminescent property test data of organic electroluminescent devices

[0393]

[0394]

[0395] Note: T95 refers to the time taken for the luminance of the device to decay to 95% at a current density of 10 mA / cm 2 ; and

[0396] From the results in Table 3, it can be seen that, compared with Comparative Examples 7-8, the luminescent efficiency and service life of the device are further improved when the compound containing a carbazole ring according to the present application is applied to the luminescent layer of the organic electroluminescent device, indicating that the compound according to the present application is a luminescent layer material with good performance.

[0397] In summary, the compound containing a carbazole ring according to the present application is an OLED material with excellent performance and has a good application prospect.

[0398] It should be noted that the present application is particularly described with individual embodiments, but those skilled in the art can make various forms or details of improvement to the present application without departing from the principles of the present application, and these improvements also fall within the protection scope of the present application.

Claims

1. A compound containing a carbazole ring, characterized by, having a general formula shown in structural formula 1, wherein one of Y1, Y2 is selected from a single bond, and the other is selected from an O atom, an S atom, or C(R1R2); v is the same or different and is selected from C(R3) or an N atom, and the bonding v is selected from C; Ar1 is selected from a group shown in formula 1-a; Y3 is selected from an O atom, an S atom, C(R4R5), or N(R6); z is the same or different and is selected from C(R7) or an N atom, and the bonding z is selected from C; R1, R2, R4, R5 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R1 and R2 are connected to each other to form a substituted or unsubstituted ring; R6 is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; R3, R7 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring, or two adjacent R7 are connected to each other to form a substituted or unsubstituted ring; provided that at least one group shown in formula 1-b is contained in formula 1; x is the same or different and is selected from C(R8) or an N atom, and the bonding x is selected from C; R8 is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic and C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R8 are connected to each other to form a substituted or unsubstituted ring; ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group; L1, L a is independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aryl ring-based fused ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

2. The compound containing a carbazole ring according to claim 1, characterized by formula 1 is selected from any one of the following structural formulae: Ar1, L1, v, R1, R2 are defined in the same way as in formula 1.

3. The carbazolophan ring-containing compound according to claim 1, characterized by Ar1 is selected from any one of the following structures: R7is selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, a group represented by 1-b, and the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, any one or more of which is substituted with multiple substituents which are the same or different from each other; or adjacent two R7are connected to each other to form a substituted or unsubstituted: benzene ring, naphthalene ring, anthracene ring, pyridine ring, pyrimidine ring, cyclopentane ring, cyclohexane ring; R4and R5are selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, a group represented by 1-b, and the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, any one or more of which is substituted with multiple substituents which are the same or different from each other, or R4and R5are connected to each other to form a substituted or unsubstituted ring; R6is selected from the group consisting of hydrogen, deuterium, a group represented by 1-b, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, in case of being substituted with a plurality of substituents, the plurality of substituents are the same as or different from each other; b is selected from 0, 1, 2, 3, or 4; b1 is selected from 0, 1, 2, or 3; b2 is selected from 0, 1, or 2; b3 is selected from 0, 1, 2, 3, 4, 5, or 6; b4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

4. The carbazole ring-containing compound according to claim 1, wherein in the formula 1-b is selected from any one of the following structures: R8and R9are the same or different, and are selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, a substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, or any one or more of adjacent two R8may be connected to each other to form a substituted or unsubstituted ring. n is independently selected from 0, 1, 2 or 3; n1 is independently selected from 0, 1 or 2; n2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; n3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; n4 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; n5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; n6 is independently selected from 0, 1, 2, 3 or 4; n7 is independently selected from 0, 1, 2, 3, 4 or 5; n8 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7.

5. The carbazole ring-containing compound according to claim 1, wherein said L1, L a is independently selected from a single bond or any one of the following groups or combinations thereof: said t is the same or different and is selected from C(R 10 ) or N, said R 10 is the same or different and is selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclyl and C6-C30 aryl fused ring group, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl group; or said adjacent two R 10 may be connected to each other to form a substituted or unsubstituted ring; said T1is independently selected from an O atom, an S atom, a C(R 11 R 12 ) or N(R 13 ); said T2is independently selected from an O atom, an S atom or N(R 14 ) ; Ring B is selected from substituted or unsubstituted C3-C15 alicyclic group; R 11 , R 12 are independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted condensed ring group of C3-C15 alicyclyl and C6-C30 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl group, or R 11 and R 12 may be connected to each other to form a substituted or unsubstituted ring; R 13 , R 14 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C15 cycloalkyl fused with C6-C30 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl group.

6. The carbazole ring-containing compound according to claim 1, wherein said L1, L a is independently selected from a single bond or any one of the following groups or combinations thereof: said R 10 , R 15 is independently selected from the group consisting of hydrogen, deuterium, cyano, halogen, nitro, a group represented by Formula 1-b, and any one or more of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, i-butyl, t-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornane, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthryl, phenanthryl, triphenylenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, t-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, or the two adjacent R 10 groups are connected to each other to form a substituted or unsubstituted ring. The R 14 The following groups are independently selected from hydrogen, deuterium, the groups shown in 1-b, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiopheneyl, and indoleyl. d1 is independently selected from 0, 1, 2, 3 or 4; d2 is independently selected from 0, 1, 2 or 3; d3 is independently selected from 0, 1 or 2; d4 is selected from 0, 1, 2, 3, 4, 5 or 6; d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; d6 is selected from 0, 1, 2, 3, 4 or 5; d8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

7. The carbazolophan ring-containing compound according to claim 1, wherein The compound containing carbazole and ring represented by Formula 1 is selected from any one of the following chemical structures:

8. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being positioned between the anode and the cathode or outside one or more of the electrodes, characterized in that, The organic layer contains the compound containing carbazole and ring according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that The organic layer is located between an anode and a cathode, and includes at least one of a hole transport region, a light emitting layer, and an electron transport region, the light emitting layer is located between the hole transport region and the electron transport region, and the light emitting layer contains the compound containing carbazole and ring according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between an anode and a cathode, and includes at least one of a hole transport region, a light emitting layer, and an electron transport region, the light emitting layer is located between the hole transport region and the electron transport region, and the light emitting layer contains the compound containing carbazole and ring according to any one of claims 1 to 7.

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