Carbazole-containing compound and organic electroluminescent device thereof

Abstract

The invention provides a carbazole-containing compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The carbazole-containing compound provided by the invention has a relatively high hole transport rate, when the carbazole-containing compound is applied to a hole transport region of an organic electroluminescent device, the luminous efficiency and the service life of the device are improved, and the carbazole-containing compound has a proper HOMO energy level, so that the distribution of electrons and holes in a luminous layer is more balanced, and the luminous efficiency of the device is improved. When the compound is applied to the light-emitting layer, the light-emitting efficiency of a device can be effectively improved, and the service life of the device can be effectively prolonged. Meanwhile, when the compound is applied to a covering layer of an organic electroluminescent device, the luminous efficiency of the device is further improved, and the service life of the device is further prolonged. 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] This invention relates to the field of organic electroluminescent materials technology, specifically to a carbazole-containing compound and its organic electroluminescent device. Background Technology

[0002] With the rapid development of semiconductor lighting technology, organic light-emitting diodes (OLEDs) have been widely used in display, lighting, backlighting and other fields due to their significant advantages such as low energy consumption, long lifespan, fast response speed, good color purity, high definition and good flexibility. They are considered by the industry to be one of the most promising display and lighting technologies.

[0003] OLEDs employ a typical sandwich structure, consisting mainly of an anode, a cathode, and an organic functional layer situated between the two electrodes (or additionally placed on the outer side). This organic functional layer typically encompasses core functional layers such as the hole transport layer (HTL), electron transport layer (ETL), emissive layer (EML), hole injection layer (HIL), electron injection layer (EIL), hole blocking layer (HBL), electron blocking layer (EBL), and capping layer (CPL). These layers work synergistically to significantly improve the device's luminous efficiency, extend its lifespan, and enhance operational stability. The light-emitting mechanism of this type of device is as follows: During the operation of the device, when a specific voltage is applied between the anode and the cathode, holes are injected from the anode into the organic functional layer, and electrons are injected from the cathode. Subsequently, these injected charge carriers (holes and electrons) recombine in the light-emitting layer and form excitons. The excitons further transfer energy to the light-emitting molecules, causing the light-emitting molecules to transition from the ground state to the excited state. The light-emitting molecules in the excited state release energy through the radiation deactivation process and radiate visible light in the form of photons, thereby realizing the electroluminescence function.

[0004] Despite significant advancements in OLED technology, numerous technical bottlenecks remain to be addressed in its industrial applications. In the structural design of OLED devices, the performance of the hole transport layer, emissive layer, and capping layer directly determines the device's luminous efficiency, stability, and lifespan, making them key factors influencing the core competitiveness of OLED products. Therefore, designing higher-performance hole transport layer, emissive layer, and capping layer materials is crucial and has become a current research focus. Summary of the Invention

[0005] The purpose of this invention is to provide a carbazole-containing compound and an organic electroluminescent device thereof. When the carbazole-containing compound provided by this invention is applied to an organic electroluminescent device, the luminous efficiency and lifespan of the organic electroluminescent device can be improved, thus solving the problems of low luminous efficiency and short lifespan of existing organic electroluminescent devices.

[0006] Specifically, it has the general formula shown in Equation 1-1 or Equation 1-2,

[0007]

[0008] The Ar1 is selected from the group shown in Formula 2;

[0009] The x atoms that are the same or different are selected from C(R1) or N atoms, and the x atoms at the bonding site are selected from C;

[0010] The R1s, whether identical or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C36 aryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C6-C30 heteroaryl, or the R1s may serve as a linking site bonded to L1, or two adjacent R1s may bond to each other to form a substituted or unsubstituted ring.

[0011] The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following;

[0012] The R a R b R c R d R f R g The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond to each other to form substituted or unsubstituted rings, or the R a R b Rc R d R f R g Any one of them can be used as a connection site to bond with L1;

[0013] The R h Selected from one of hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl groups, or the R group. h It serves as a connection site and bonds to L1;

[0014] The z atoms are selected from C(R0) or N atoms, and the z atoms at the bonding sites are selected from C.

[0015] The same or different R0s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or two adjacent R0s are bonded to each other to form a substituted or unsubstituted ring;

[0016] The Ar2 is selected from any one of the following groups or combinations thereof:

[0017]

[0018] The t atoms are selected from CH or N atoms, and the t atoms at the bonding sites are selected from C atoms;

[0019] The T1 is selected from O atoms, S atoms, C (R3R4) or N (R5) in the same or different ways;

[0020] The T2 is independently selected from O atoms, S atoms, or N(R6);

[0021] T3 and T4 are independently selected from O atoms or S atoms;

[0022] The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0023] The ring B is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups.

[0024] The R 222The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group;

[0025] The R2s, whether identical or different, are selected from one of the following: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s bonded together to form a substituted or unsubstituted ring.

[0026] R3 and R4 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or R3 and R4 may be interconnected to form substituted or unsubstituted rings;

[0027] R5 and R6 are independently selected from any one of hydrogen, deuterium, 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 combinations thereof;

[0028] The b1 is selected from 1, 2, 3, 4, or 5; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b2 is selected from 0, 1, 2, 3, or 4; the b3 is selected from 0, 1, or 2; the b4 is selected from 0, 1, 2, or 3; the b 14 Selected from 0, 1, 2, 3, 4, or 5; b 15 Choose from 1, 2, 3, or 4;

[0029] The Ar3 is selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, and R. 777 Substituted phenyl, R 777 Substituted biphenyl, R 777The group consisting of any one of the following: substituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C7-C30 fused aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C2-C30 heteroaryl, or any one of the groups shown in Formula 2.

[0030] The R 777 The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group;

[0031] The Ar4 is selected from any one of the groups shown below or the group shown in Formula 2.

[0032]

[0033]

[0034] The q atoms are selected from CH or N atoms, and the q atoms at the bonding sites are selected from C.

[0035] The M1 is selected from O atoms, S atoms, C(R) atoms, or different atoms. 30 R 40 ) or N(R 50 );

[0036] The M2 is independently selected from O atoms, S atoms, or N(R) atoms. 60 );

[0037] M3 and M4 are independently selected from O atoms or S atoms;

[0038] The ring M is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0039] The ring N is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups;

[0040] The R P The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0041] The R 30 R 40Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or the R 30 and R 40 They can connect with each other to form substituted or unsubstituted rings;

[0042] The R 50 R 60 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof;

[0043] The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n4 is selected from 0, 1, 2, 3, or 4; the n5 is selected from 0, 1, or 2; the n6 is selected from 0, 1, 2, or 3; and the n7 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0044] L1, L2, L3, and L4 are 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 cycloalcohol, and substituted or unsubstituted C2-C30 heteroarylene.

[0045] 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.

[0046] Beneficial Effects: The carbazole-containing compounds provided by this invention possess high hole transport rates. When applied to the hole transport region of organic light-emitting devices (OLEDs), the luminous efficiency and lifespan of the OLEDs are improved. Furthermore, they exhibit appropriate HOMO energy levels, resulting in a more balanced distribution of electrons and holes in the emissive layer and enhancing exciton recombination efficiency. Therefore, when applied to the emissive layer of OLEDs, they effectively improve the luminous efficiency and lifespan of the devices. Simultaneously, when applied to the capping layer of OLEDs, they further improve the luminous efficiency and lifespan of the OLEDs. The compound preparation method of this invention is simple, and the raw materials are readily available. It can be widely applied in fields such as organic thin-film transistors and panel displays, demonstrating good application effects and industrialization prospects. Detailed Implementation

[0047] 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.

[0048] 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.

[0049] Examples of halogens described in this invention may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0050] In this invention, "C1-C15" in "substituted or unsubstituted C1-C15 alkyl groups" refers to the number of carbon atoms in the unsubstituted alkyl group, excluding the number of carbon atoms in the substituents. Similarly, "C6-C30" in "substituted or unsubstituted C6-C30 aryl groups" refers to the number of carbon atoms in the unsubstituted aryl group, excluding the number of carbon atoms in the substituents. And so on.

[0051] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has 1 to 15 carbon atoms, preferably 1 to 10. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0052] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0053] The alkenyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an olefin molecule, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. Examples may include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, etc., but are not limited thereto.

[0054] The alkoxy group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkoxy hydrocarbon molecule, preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Examples may include methoxy, ethoxy, propoxy, butoxy, etc., but are not limited thereto.

[0055] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, phenanthrene, triphenylene, anthracene, pyrene, fluorenyl, spirodifluorenyl, spiroanthracenefluorenyl, benzo[a]fluorenyl, benzo[a]spirodifluorenyl, etc.

[0056] The alicyclic group described in this invention refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a 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-like structure, such as adamantane, norbornane, camphene, etc., but are not limited thereto.

[0057] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Examples of fused alicyclic and aromatic ring groups may include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 18, and even more preferably 6 to 12.

[0058] The heteroaryl group described in this invention refers to a monovalent group in which at least one aromatic carbon atom is replaced by a heteroatom. The heteroaryl group has a carbon number of C2 to C30, preferably C2 to C15, and even more preferably C2 to C10. The heteroatom includes, but is not limited to, the atoms listed below: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, the groups listed below: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, carbazoleyl, etc., but are not limited thereto.

[0059] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom in an aromatic hydrocarbon molecule. The arylene group has a carbon number of C6 to C30, preferably C6 to C20, and even more preferably C6 to C10. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene groups include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, perylene, pyrene, indene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, etc.

[0060] The fused alicyclic and aromatic rings described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Examples of fused alicyclic and aromatic rings may include, but are not limited to, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, and naphthocyclopentane. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 18.

[0061] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C20, and even 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, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl groups include, but are not limited to, the following groups: pyridylene, pyrimidinylene, quinolineylene, isoquinolineylene, furanylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thiophenylene, benzothiophenylene, dibenzothiophenylene, benzodibenzothiophenylene, etc.

[0062] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: halogen atom, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 alicyclic group, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocyclic alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, preferably halogen atom, cyano, nitro The alkyl group, C1-C12 alkyl group, C3-C12 alicyclic group, C3-C12 heterocyclic alkyl group, C6-C30 aryl group, and C3-C30 heteroaryl group, when substituted by multiple substituents, are either the same or different from each other; preferably, this means unsubstituted or substituted by one or more substituents selected from the group consisting of: fluorine atom, cyano, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, cyclobutane, methyl-substituted Cyclobutyl, ethyl-substituted cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, tetrahydropyridine The following groups are used: pyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazoyl, dibenzofuranyl, and dibenzothiopheneyl. When substituted with multiple substituents, the multiple substituents may be the same or different from each other.

[0063] In this invention, when the bond containing the substituent or linking site extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.

[0064] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring.

[0065] For example, Can represent Can represent Can represent And so on.

[0066] In this invention, "adjacent groups can connect with each other to form substituted or unsubstituted rings" refers to the formation of substituted or unsubstituted hydrocarbon rings or substituted or unsubstituted heterocycles by the combination of adjacent groups and optional aromatization. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Examples are shown below:

[0067]

[0068]

[0069] In this invention, 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 the two. 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, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0070] This invention provides a carbazole-containing compound having the general formula shown in Formula 1-1 or Formula 1-2.

[0071]

[0072] The Ar1 is selected from the group shown in Formula 2;

[0073] The x atoms that are the same or different are selected from C(R1) or N atoms, and the x atoms at the bonding site are selected from C;

[0074] The R1s, whether identical or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C36 aryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C6-C30 heteroaryl, or the R1s may serve as a linking site bonded to L1, or two adjacent R1s may bond to each other to form a substituted or unsubstituted ring.

[0075] The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following;

[0076] The R a R b R c R d R f R g The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond to each other to form substituted or unsubstituted rings, or the R a R b R c R d R f R g Any one of them can be used as a connection site to bond with L1;

[0077] The R hSelected from one of hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl groups, or the R group. h It serves as a connection site and bonds to L1;

[0078] The z atoms are selected from C(R0) or N atoms, and the z atoms at the bonding sites are selected from C.

[0079] The same or different R0s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or two adjacent R0s are bonded to each other to form a substituted or unsubstituted ring;

[0080] The Ar2 is selected from any one of the following groups or combinations thereof:

[0081]

[0082] The t atoms are selected from CH or N atoms, and the t atoms at the bonding sites are selected from C atoms;

[0083] The T1 is selected from O atoms, S atoms, C (R3R4) or N (R5) in the same or different ways;

[0084] The T2 is independently selected from O atoms, S atoms, or N(R6);

[0085] T3 and T4 are independently selected from O atoms or S atoms;

[0086] The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0087] The ring B is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups.

[0088] The R 222 The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group;

[0089] The R2s, whether identical or different, are selected from one of the following: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s bonded together to form a substituted or unsubstituted ring.

[0090] R3 and R4 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or R3 and R4 may be interconnected to form substituted or unsubstituted rings;

[0091] R5 and R6 are independently selected from any one of hydrogen, deuterium, 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 combinations thereof;

[0092] The b1 is selected from 1, 2, 3, 4, or 5; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b2 is selected from 0, 1, 2, 3, or 4; the b3 is selected from 0, 1, or 2; the b4 is selected from 0, 1, 2, or 3; the b 14 Selected from 0, 1, 2, 3, 4, or 5; b 15 Choose from 1, 2, 3, or 4;

[0093] The Ar3 is selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, and R. 777 Substituted phenyl, R 777 Substituted biphenyl, R 777 The group consisting of any one of the following: substituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C7-C30 fused aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C2-C30 heteroaryl, or any one of the groups shown in Formula 2.

[0094] The R 777The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group;

[0095] The Ar4 is selected from any one of the groups shown below or the group shown in Formula 2.

[0096]

[0097] The q atoms are selected from CH or N atoms, and the q atoms at the bonding sites are selected from C.

[0098] The M1 is selected from O atoms, S atoms, C(R) atoms, or different atoms. 30 R 40 ) or N(R 50 );

[0099] The M2 is independently selected from O atoms, S atoms, or N(R) atoms. 60 );

[0100] M3 and M4 are independently selected from O atoms or S atoms;

[0101] The ring M is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0102] The ring N is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups;

[0103] The R P The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl;

[0104] The R 30 R 40 Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or the R 30 and R 40 They can connect with each other to form substituted or unsubstituted rings;

[0105] The R50 R 60 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof;

[0106] The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n4 is selected from 0, 1, 2, 3, or 4; the n5 is selected from 0, 1, or 2; the n6 is selected from 0, 1, 2, or 3; and the n7 is selected from 0, 1, 2, 3, 4, 5, or 6.

[0107] L1, L2, L3, and L4 are 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 cycloalcohol, and substituted or unsubstituted C2-C30 heteroarylene.

[0108] Preferably, the Ar1 is selected from any one of the following structures:

[0109]

[0110] The x atoms that are the same or different are selected from C(R1) or N atoms, and the x atoms at the bonding site are selected from C;

[0111] R1 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl Anthracene, phenanthrene, triphenylene, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, indolyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R1s are connected to each other to form substituted or unsubstituted rings;

[0112] The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a Rb ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following;

[0113] The R a R b R c R d R f R g The same or different from the following groups selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene. The following are some of the following: phenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond with each other to form substituted or unsubstituted rings;

[0114] The R h Selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene The substituents are any one or more of the following: yl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzimidazolyl, benzothiazolyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other.

[0115] Preferably, the Ar1 is selected from any one of the following structures:

[0116]

[0117] R1 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indole, furfural. Any one or more of the following: uryl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilane, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0118] The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following;

[0119] The R a R b R c R d R f R gThe same or different from the following groups selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene. The following are some of the following: phenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond with each other to form substituted or unsubstituted rings;

[0120] The R h Selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene The substituents are any one or more of the following: yl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzimidazolyl, benzothiazolyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents may be the same as or different from each other;

[0121] The a is selected from 0, 1, 2, 3 or 4; the a1 is selected from 0, 1, 2 or 3; the a2 is selected from 0, 1 or 2; the a3 is selected from 0, 1, 2, 3, 4, 5 or 6; the a4 is selected from 0, 1, 2, 3, 4 or 5.

[0122] Preferably, the Ar2 is selected from any one of the following groups:

[0123]

[0124]

[0125]

[0126] The R2, R 22 The following groups, selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene. The following are any one or more of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R2s are connected to each other to form a substituted or unsubstituted ring;

[0127] R5 and R6 are selected, either identically or differently, from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, silyl, where, when substituted by multiple substituents, the multiple substituents are identical or different from each other;

[0128] The b1 is independently selected from 1, 2, 3, 4, or 5; the b2 is independently selected from 0, 1, 2, 3, or 4; the b3 is independently selected from 0, 1, or 2; the b4 is independently selected from 0, 1, 2, or 3; the b5 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 6; the b7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b 10Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the b 12 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the b 13 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; the b 14 Selected from 0, 1, 2, 3, 4, or 5; b 15 Choose independently from 1, 2, 3 or 4.

[0129] Preferably, the Ar3 is selected from any one of the following groups: deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, or combinations thereof:

[0130]

[0131] The E1 is selected from O atoms, S atoms, C (R8R9) or N (R 10 );

[0132] The E2 is independently selected from O atoms, S atoms, or N(R) atoms. 11 );

[0133] E3 and E4 are independently selected from O atoms or S atoms;

[0134] The ring D is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0135] The P is selected from N or CH; the P at the bonding site is selected from C;

[0136] The R7s are selected from any of the following groups, whether identical or different: deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or adjacent R7s may be interconnected to form substituted or unsubstituted rings.

[0137] The R 777The following groups, selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and any one or more of these groups, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other;

[0138] R8 and R9 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or R8 and R9 may be interconnected to form substituted or unsubstituted rings;

[0139] The R 10 R 11 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof;

[0140] The d1 is selected from 1, 2, 3, 4, or 5; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, or 2; the d4 is selected from 0, 1, 2, or 3; the d 14 Selected from 0, 1, 2, 3, 4, or 5; the d 15 Choose from 1, 2, 3, or 4.

[0141] More preferably, the Ar3 is selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, any one of the following groups or combinations thereof:

[0142]

[0143]

[0144]

[0145] The R7, R 77 The following groups, selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridine The following are any one or more of the following: pyridinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphtholinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R7s are connected to each other to form substituted or unsubstituted rings;

[0146] The R 10 R 11The following groups, selected from hydrogen, deuterium, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, and silyl, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other;

[0147] The d1 is independently selected from 0, 1, 2, 3, 4, or 5; the d2 is independently selected from 0, 1, 2, 3, or 4; the d3 is independently selected from 0, 1, or 2; the d4 is independently selected from 0, 1, 2, or 3; the d5 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d6 is independently selected from 0, 1, 2, 3, 4, 5, or 6; the d7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the d8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the d9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the d 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the d 12 Select independently from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12.

[0148] Preferably, Ar2 is selected from pentadeuterated phenyl or pentafluorophenyl. Preferably, Ar3 is selected from pentadeuterated phenyl or pentafluorophenyl.

[0149] Preferably, Ar2 is the same as Ar3.

[0150] Preferably, the Ar4 is selected from any one of the following groups or the groups shown in Formula 2:

[0151]

[0152] The R p R ppThe following groups, selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, di... The substituents are any one or more of the following: hydronaphthyl, anthraceneyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other;

[0153] The R 50 R 60 The following groups, selected from hydrogen, deuterium, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzothiazolyl, carbazole, and silyl, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other;

[0154] The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n4 is selected from 0, 1, 2, 3, or 4; the n5 is selected from 0, 1, or 2; the n6 is selected from 0, 1, 2, or 3; the n7 is selected from 0, 1, 2, 3, 4, 5, or 6; the n8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the n9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the n 11 Select independently from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0155] Preferably, L1, L2, L3, and L4 are independently selected from single bonds or any combination of the following groups:

[0156]

[0157] The i that are the same or different are selected from C(R) 16 ) or N, the R 16 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 16 They can connect with each other to form substituted or unsubstituted rings;

[0158] The Q3 is independently selected from O atoms, S atoms, C(R) atoms, and S atoms. 17 R 18 ) or N(R 19 );

[0159] The Q4 is independently selected from O atoms, S atoms, or N(R) atoms. 20 );

[0160] The ring F is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0161] The R 17 R 18 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 17 and R 18 They can connect with each other to form substituted or unsubstituted rings;

[0162] The R 19 R 20 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C18 heteroaryl, and substituted or unsubstituted silyl.

[0163] More preferably, L1, L2, L3, and L4 are independently selected from single bonds or any combination of the following groups:

[0164]

[0165] The R9, R 99 R 10 R 11 The following groups, independently selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, Triphenylene, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, silyl, when substituted with multiple substituents, the multiple substituents may be the same or different from each other, or the two adjacent R9s may be interconnected to form a substituted or unsubstituted ring, or the R... 10 and R 11 These groups can connect to each other to form substituted or unsubstituted rings; the substituents in "substituted or unsubstituted" are selected from: deuterium, cyano, halogen, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, Biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other;

[0166] The R 12 R 13The following groups are independently selected from hydrogen, deuterium, 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.

[0167] h1 is independently selected from 0, 1, 2, 3 or 4; h2 is independently selected from 0, 1, 2 or 3; h3 is independently selected from 0, 1 or 2; h4 is selected from 0, 1, 2, 3, 4, 5 or 6; h5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0168] Most preferably, the carbazole-containing compound represented by Formula 1-1 or Formula 1-2 is selected from any one of the following chemical structures:

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] The above lists some specific chemical structures of carbazole-containing compounds of structural formula 1-1 or formula 1-2 of the present invention. However, the present invention is not limited to these listed chemical structures. All compounds based on carbazole-containing compounds of structural formula 1-1 or formula 1-2 with substituents as defined above should be included.

[0215] Furthermore, 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 a carbazole-containing compound as shown in Formula 1-1 or Formula 1-2 of the present invention.

[0216] Preferably, the organic layer is located between the anode and the cathode or on the outside of one or more electrodes of the anode and the cathode. The organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer. At least one of the hole transport region, the light-emitting layer, and the capping layer contains a carbazole-containing compound as shown in Formula 1-1 or Formula 1-2 of the present invention.

[0217] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, wherein at least one of the hole transport regions contains a carbazole-containing compound as shown in Formula 1-1 or Formula 1-2 of the present invention.

[0218] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, wherein the light-emitting layer contains a carbazole-containing compound as shown in Formula 1-1 or Formula 1-2 of the present invention.

[0219] Preferably, the organic layer is located outside one or more of the electrodes, the anode and the cathode, and the organic layer includes a capping layer containing a carbazole-containing compound as shown in Formula 1-1 or Formula 1-2 of the present invention.

[0220] Preferably, the capping layer is located outside the cathode, and the capping layer contains at least one or more of the carbazole-containing compounds described in this invention.

[0221] Preferably, the covering layer may comprise one or more layers; specifically, the covering layer comprises at least one of a first covering layer, a second covering layer, and a third covering layer, wherein at least one of the first covering layer, the second covering layer, or the third covering layer comprises any one or more of the carbazole-containing compounds described in this invention.

[0222] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, quartz, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0223] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below:

[0224] The anode of this invention preferably uses a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically above 4.0 eV). The anode can be a reflective anode, such as a reflective film formed from silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed from indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific choice depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode is required; if the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode is required.

[0225] The hole injection material described in this invention is preferably a material capable of reducing the interfacial barrier between the anode and the hole transport layer, including at least one of metal oxides, materials with hole transport characteristics, and p-type dopants. Examples of substances with high hole-injection potential include 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (DPA3B), and 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9- Aromatic amine compounds such as phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1), as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarboxylonitrile (HAT-CN), polymers such as poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD), are included, but are not limited to these. The carbazole-containing compounds described in this invention are preferred.

[0226] The hole transport material of this invention is preferably a material capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer, and possesses high hole mobility and good stability. The hole transport material of this invention 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 a hole injection layer, and can be a single-layer structure or a multi-layer structure. For example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc., can be used as the hole transport layer material. Specific examples may 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'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), etc., but not limited thereto. Preferably, the carbazole-containing compounds described in this invention are preferred.

[0227] The preferred electron blocking layer material of this invention has a triplet (T1) energy level higher than the T1 energy level of the host material in the emissive layer, thus blocking energy loss from the emissive layer material. The HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the host material in the emissive layer, facilitating hole injection from the positive electrode into the emissive layer. Simultaneously, the electron blocking layer material is required to have high hole mobility to facilitate hole transport and reduce the power consumption of the device. The LUMO energy level of the electron blocking layer material is higher than the LUMO energy level of the host material in the emissive layer, serving as an electron blocker; that is, the electron blocking layer material is required to have a wide bandgap (Eg). Electron blocking layer materials meeting the above conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. Examples include, but are not limited to, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine; dibenzofuran derivatives, such as N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc. Carbazole-containing compounds as described in this invention are preferred.

[0228] 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.

[0229] 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 N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), 4-(10-phenyl-9-anthrayl)triphenylamine, etc. 4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviation: PCPAPA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-9H-carbazole-3-amine) -2-Anthracene)-N,N',N'-Triphenyl-1,4-Phenylenediamine (abbreviated as: 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-Triphenyl-1,4-Phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracene-2-amine ( Examples of carbazole-containing compounds include, but are not limited to, N,N,9-triphenylanthracene-9-amine (abbreviated as DPhAPhA), N,N,N',N'-tetra(4-methylphenyl)-tetraphenyl-5,11-diamine (abbreviated as p-mPhTD), and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD). The carbazole-containing compounds described in this invention are preferred.

[0230] As the guest material of the luminescent layer in this invention, it may include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as 4,4'-bis(4-(9H-carbazole-9-yl)styryl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenyltetraphenyl (Rubrene), coumarin 545T (C-525T)tris(2-phenyl-3-methylpyridine)iridium (Ir(3mppy) 3), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium(III)(Ir(npy)2acac), tri(2-phenylpyridine)iridium(III)(Ir(ppy)3), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac), etc., but not limited to these.

[0231] The hole-blocking layer material described in this invention needs to have good hole-blocking ability in order to block holes within the light-emitting layer. Materials such as imidazole derivatives, phenanthroline derivatives, metal complexes, and triazine derivatives are examples. Specific examples may include, but are not limited to, 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphth-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), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc.

[0232] The electron transport layer material described in this invention can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials typically contain metal complexes and / or nitrogen-containing heterocyclic derivatives. The metal complexes may be selected from, for example, LiQ, Alq3, etc. The nitrogen-containing heterocyclic derivatives may be aromatic rings with a nitrogen-containing six-membered or five-membered ring skeleton, fused aromatic ring compounds with a nitrogen-containing six-membered or five-membered ring skeleton, etc. Specific examples include, but are not limited to, those mentioned above. BPhen, 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzi[d]imidazolium, 2-(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but not limited to these.

[0233] The electron injection layer material described in this invention is preferably a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. Examples include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances with high electron injection capacity. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, cesium 8-hydroxyquinoline, and tris(8-hydroxyquinoline)aluminum. Furthermore, a mixture of multiple of these compounds can also be used.

[0234] The cathode described in this invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, 3.8 eV or less). Examples include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), as well as rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. However, this is not an exclusive limitation.

[0235] The anode and cathode described in this invention can each be formed as a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the types of materials forming the anode and cathode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a side-emitting type.

[0236] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, heterocyclic compounds, etc. Specific examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (abbreviated CBP), and carbazole-containing compounds shown in Formula 1-1 or Formula 1-2 of this invention, but are not limited thereto. Preferably, the carbazole-containing compounds described in this invention are preferred.

[0237] The n-type charge-generating material described in this invention can be selected from one of the following materials or combinations thereof: tri-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-phenololine)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-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-(naphthyl-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]-alternating-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), etc., but not limited to these. In addition, auxiliary N-type charge-generating materials may 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, but not limited to these, or an alkaline earth metal, such as Be, Mg, Ca, Sr, Ba or Ra, but not limited to these.

[0238] The p-type charge-generating material of this invention may comprise one of the following materials or combinations thereof: 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-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-hexaazatriphenylhexacarbonitrile (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-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, etc., but not limited to these.

[0239] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., can be used, but are not limited to these. There are no particular limitations on the film thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5nm to 10μm, more preferably 10nm to 0.2μm.

[0240] The organic electroluminescent device of the present invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, televisions, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, lighting equipment, etc.

[0241] Synthesis Examples

[0242] Raw materials and reagents: This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well-known to those skilled in the art. All raw materials and reagents used in this invention are of reagent purity.

[0243] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0244] There are no particular limitations on the preparation method of the carbazole-containing compounds of structural formula 1-1 or formula 1-2 of the present invention, and conventional methods 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-containing compounds of structural formula 1-1 or formula 1-2 of the present invention can be prepared by the synthetic route shown below.

[0245] Synthetic route 1, and When selected from different groups:

[0246]

[0247] Synthesis Route 2: and When selected from the same group:

[0248]

[0249] Synthesis Route 3:

[0250]

[0251] X1, X2, and X3 are independently selected from any one of I, Br, and Cl;

[0252] The above-mentioned substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0253] Preparation and characterization of compounds

[0254] Description of raw materials, reagents, and characterization equipment:

[0255] The present invention does not impose any particular restrictions on the source of raw materials and reagents used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0256] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0257] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0258] Synthesis Example 1: Preparation of Intermediate a-58

[0259]

[0260] Under nitrogen protection, starting materials m-68 (29.38 g, 80.00 mmol), n-68 (16.07 g, 80.00 mmol), K2CO3 (16.59 g, 120.00 mmol), and 400 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. After purging the air with nitrogen three times, Pd(PPh3)4 (0.92 g, 0.80 mmol) was added. The mixture was stirred and heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling. The crystals were then filtered and recrystallized from toluene to obtain intermediate a-68 (25.05 g, yield 79%) with an HPLC purity ≥99.88%. Mass spectrometry m / z: 395.0324 (theoretical value: 395.0310).

[0261] Other intermediates required for the present invention were synthesized using the above-described synthesis method. The relevant raw materials are shown in Table 1.

[0262] Table 1:

[0263]

[0264] Synthesis Example 2: Preparation of Compound 47

[0265]

[0266] Preparation of intermediate A-47

[0267] Under nitrogen protection, a-47 (22.49 g, 80.00 mmol), pinacol diborate (20.52 g, 80.80 mmol), and KOAc (15.70 g, 160.00 mmol) dissolved in 450 mL of 1,4-dioxane were added to a reaction flask with stirring. Pd(PPh3)4 (1.85 g, 1.60 mmol) was then added, and the mixture was heated under reflux for 5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the resulting solid using toluene / ethanol at a ratio of 9:1 to give intermediate A-47 (20.48 g, yield 78%); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 328.1647 (theoretical value: 328.1635).

[0268] Preparation of intermediate B-47

[0269] Under nitrogen protection, A-47 (19.69 g, 60.00 mmol), b-47 (14.77 g, 60.00 mmol), and K₂CO₃ (16.59 g, 120.00 mmol) were dissolved in 300 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at an 8:1 ratio to give intermediate B-47 (16.76 g, 76% yield); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 367.1372 (theoretical value: 367.1361).

[0270] Preparation of compound 47

[0271] Under nitrogen protection, B-47 (14.70 g, 40.00 mmol), c-47 (15.85 g, 40.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) dissolved in 180 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.37 g, 0.40 mmol) and X-Phos (0.38 g, 0.80 mmol) were then added. The mixture of the above reactants was heated under reflux for 6.5 h. After the reaction was complete, the mixture 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. Recrystallization from toluene yielded compound 47 (20.21 g, 74% yield). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 682.2422 (theoretical value: 682.2409). Theoretical elemental content C 52 H 30 N2: C, 91.47; H, 4.43; N, 4.10; (%) Measured element content (%): C, 91.45; H, 4.47; N, 4.05.

[0272] Synthesis Example 3: Preparation of Compound 56

[0273]

[0274] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-56, b-47 with an equimolar amount of b-56, and c-47 with an equimolar amount of c-56, yielding compound 56 (19.41 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 672.2330 (theoretical value: 672.2348). Theoretical elemental content (%) C 46 H 32N4S: C, 82.11; H, 4.79; N, 8.33. Measured elemental content (%): C, 82.15; H, 4.82; N, 8.30.

[0275] Synthesis Example 4: Preparation of Compound 68

[0276]

[0277] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-68, and c-47 was replaced with an equimolar amount of c-68 to obtain compound 68 (20.24 g). HPLC analysis showed that the solid purity was ≥99.95%. Mass spectrometry m / z: 676.2247 (theoretical value: 676.2263). Theoretical elemental content (%) C 48 H 28 N4O: C, 85.19; H, 4.17; N, 8.28. Measured elemental content (%): C, 85.22; H, 4.15; N, 8.30.

[0278] Synthesis Example 5: Preparation of Compound 76

[0279]

[0280] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-76, and c-47 was replaced with an equimolar amount of c-56, yielding compound 76 (20.17 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 690.2145 (theoretical value: 690.2130). Theoretical elemental content (%) C 50 H 30 N2S: C, 86.93; H, 4.38; N, 4.05. Measured elemental content (%): C, 86.90; H, 4.36; N, 4.09.

[0281] Synthesis Example 6: Preparation of Compound 78

[0282]

[0283] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-78, and b-47 was replaced with an equimolar amount of b-78 to obtain compound 78 (25.85 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 872.2671 (theoretical value: 872.2681). Theoretical elemental content (%) C 62 H 40 N₂SSi: C, 85.29; H, 4.62; N, 3.21. Measured elemental content (%): C, 85.27; H, 4.65; N, 3.23.

[0284] Synthesis Example 7: Preparation of Compound 85

[0285]

[0286] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-85, b-47 was replaced with an equimolar amount of b-85, and c-47 was replaced with an equimolar amount of c-56, yielding compound 85 (20.73 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 740.2296 (theoretical value: 740.2286). Theoretical elemental content (%) C 54 H 32 N2S: C, 87.54; H, 4.35; N, 3.78. Measured elemental content (%): C, 87.50; H, 4.38; N, 3.76.

[0287] Synthesis Example 8: Preparation of Compound 120

[0288]

[0289] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-120, and c-47 was replaced with an equimolar amount of c-56, yielding compound 120 (20.72 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 698.2368 (theoretical value: 698.2358). Theoretical elemental content (%) C 52 H 30 N₂O: C, 89.37; H, 4.33; N, 4.01. Measured elemental content (%): C, 89.40; H, 4.32; N, 4.03.

[0290] Synthesis Example 9: Preparation of Compound 203

[0291]

[0292] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-203, and c-47 was replaced with an equimolar amount of c-68, yielding compound 203 (20.21 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 664.1986 (theoretical value: 664.1973). Theoretical elemental content (%) C 48 H 28 N₂S: C, 86.72; H, 4.25; N, 4.21. Measured elemental content (%): C, 86.74; H, 4.20; N, 4.26.

[0293] Synthesis Example 10: Preparation of Compound 212

[0294]

[0295] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-212, and c-47 was replaced with an equimolar amount of c-212 to obtain compound 212 (23.87 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 764.2268 (theoretical value: 764.2286). Theoretical elemental content (%) C 56 H 32 N2S: C, 87.93; H, 4.22; N, 3.66. Measured elemental content (%): C, 87.95; H, 4.18; N, 3.69.

[0296] Synthesis Example 11: Preparation of Compound 259

[0297]

[0298] Preparation of intermediate A-259

[0299] Under nitrogen protection, a-259 (31.15 g, 110.00 mmol), pinacol diborate (28.44 g, 112.00 mmol), and KOAc (21.59 g, 220.00 mmol) dissolved in 420 mL of 1,4-dioxane were added to a reaction flask with stirring. Pd(PPh3)4 (2.54 g, 2.20 mmol) was then added, and the mixture was heated under reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 6:1 to give intermediate A-259 (28.70 g, yield 79%); HPLC purity ≥ 99.77%. Mass spectrometry m / z: 330.1780 (theoretical value: 330.1791).

[0300] Preparation of intermediate B-259

[0301] Under nitrogen protection, A-259 (23.12 g, 70 mmol), b-259 (19.64 g, 70.00 mmol), and K₂CO₃ (19.35 g, 140.00 mmol) were dissolved in 350 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (1.02 g, 1.40 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at an 8:1 ratio to give intermediate B-259 (21.77 g, 77% yield); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 403.1146 (theoretical value: 403.1128).

[0302] Preparation of intermediate C-259

[0303] Under argon protection, B-259 (20.20 g, 50.00 mmol), C-259 (12.66 g, 50.00 mmol), K₂CO₃ (10.37 g, 75.00 mmol), and 420 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with argon, Pd(PPh₃)₄ (0.58 g, 0.50 mmol) was added. The mixture was stirred and heated under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the toluene layer was separated and dried with anhydrous magnesium sulfate. The solvent was concentrated by rotary evaporation after filtration, and crystals were precipitated by cooling and filtration. The crystals were then recrystallized from toluene / methanol at a ratio of 10:1 to obtain intermediate C-259 (21.63 g, yield 75%) with an HPLC purity ≥99.89%. Mass spectrometry m / z: 576.2628 (theoretical value: 576.2614).

[0304] Preparation of compound 259

[0305] Under nitrogen protection, C-56 (9.61 g, 30.00 mmol), C-259 (17.30 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 135 mL of toluene were added to a reaction flask. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.29 g, 0.60 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 6.5 h. After the reaction was complete, the mixture 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. Recrystallization from toluene gave compound 259 (17.63 g, 72% yield). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 815.3360 (theoretical value: 815.3349). Theoretical elemental content (%) C 62 H 33 D5N2: C, 91.26; H, 5.31; N, 3.43. Measured elemental content (%): C, 91.28; H, 5.35; N, 3.39.

[0306] Synthesis Example 12: Preparation of Compound 296

[0307]

[0308] According to the preparation method in Synthesis Example 11, a-259 was replaced with an equimolar amount of a-296, and c-259 was replaced with an equimolar amount of c-296 to obtain compound 296 (17.73 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 686.2738 (theoretical value: 686.2722). Theoretical elemental content (%) C 52 H 34 N2: C, 90.93; H, 4.99; N, 4.08. Measured elemental content (%): C, 90.95; H, 4.96; N, 4.07.

[0309] Synthesis Example 13: Preparation of Compound 319

[0310]

[0311] According to the preparation method in Synthesis Example 11, a-259 was replaced with an equimolar amount of a-319, and c-259 was replaced with an equimolar amount of c-319 to obtain compound 319 (20.59 g). HPLC analysis showed that the solid purity was ≥99.96%. Mass spectrometry m / z: 902.3526 (theoretical value: 902.3513). Theoretical elemental content (%) C 64 H 50N₂Si₂: C, 85.10; H, 5.58; N, 3.10. Measured elemental content (%): C, 85.08; H, 5.56; N, 3.12.

[0312] Synthesis Example 14: Preparation of Compound 329

[0313]

[0314] Preparation of intermediate A-329

[0315] Under nitrogen protection, a-329 (30.72 g, 100.00 mmol), pinacol diborate (36.02 g, 101.67 mmol), and KOAc (19.63 g, 200.00 mmol) dissolved in 375 mL of 1,4-dioxane were added to a reaction flask with stirring. Pd(PPh3)4 (2.31 g, 2.00 mmol) was then added, and the mixture was heated to reflux for 6 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 6:1 to give intermediate A-329 (27.99 g, yield 79%); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 354.1779 (theoretical value: 354.1791).

[0316] Preparation of intermediate B-329

[0317] Under nitrogen protection, A-329 (28.34 g, 80 mmol), b-329 (13.00 g, 40.00 mmol), and K₂CO₃ (16.59 g, 120.00 mmol) were dissolved in 300 mL of toluene / ethanol / water (2:1:1). Pd(dppf)Cl₂ (0.88 g, 1.20 mmol) was added with stirring, and the mixture was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol (8:1) to give intermediate B-329 (18.84 g, yield 76%); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 619.2319 (theoretical value: 619.2300). Preparation of compound 329

[0318] Under nitrogen protection, C-329 (12.01 g, 30.00 mmol), B-329 (18.58 g, 30.00 mmol), and sodium tert-butoxide (4.32 g, 45.00 mmol) dissolved in 225 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.27 g, 0.30 mmol) and X-Phos (0.41 g, 0.86 mmol) were then added. The mixture of the above reactants was heated under reflux for 6.5 h. After the reaction was complete, the mixture 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. Recrystallization from toluene yielded compound 329 (21.13 g, 75% yield). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 938.3583 (theoretical value: 938.3599). Theoretical elemental content (%) C 72 H 38 D4N2: C, 92.08; H, 4.94; N, 2.98. Measured elemental content (%): C, 92.04; H, 4.96; N, 2.99.

[0319] Synthesis Example 15: Preparation of Compound 334

[0320]

[0321] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-334, and c-329 was replaced with an equimolar amount of c-56, yielding compound 334 (20.10 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 858.3050 (theoretical value: 858.3035). Theoretical elemental content (%) C 66 H 38 N2: C, 92.28; H, 4.46; N, 3.26. Measured elemental content (%): C, 92.29; H, 4.45; N, 3.29.

[0322] Synthetic Example 16: Preparation of Compound 455

[0323]

[0324] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-455, and c-329 was replaced with an equimolar amount of c-47, yielding compound 455 (16.53 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 724.2947 (theoretical value: 724.2935). Theoretical elemental content (%) C 52 H 20 D 10N2O2: C, 86.16; H, 5.56; N, 3.86. Measured elemental content (%): C, 86.14; H, 5.57; N, 3.89.

[0325] Synthesis Example 17: Preparation of Compound 478

[0326]

[0327] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-478, and c-329 was replaced with an equimolar amount of c-478 to obtain compound 478 (21.56 g, yield 77%). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 932.3741 (theoretical value: 932.3731). Theoretical elemental content (%) C 64 H 52 N4Si2: C, 82.36; H, 5.62; N, 6.00. Measured elemental content (%): C, 82.35; H, 5.58; N, 6.04.

[0328] Synthesis Example 18: Preparation of Compound 483

[0329]

[0330] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-483, and c-329 was replaced with an equimolar amount of c-56, yielding compound 483 (21.00 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 668.2230 (theoretical value: 668.2212). Theoretical elemental content (%) C 46 H 28 N4O2: C, 82.62; H, 4.22; N, 8.38. Measured elemental content (%): C, 82.61; H, 4.25; N, 8.36.

[0331] Synthesis Example 19: Preparation of Compound 512

[0332]

[0333] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-512, and c-329 was replaced with an equimolar amount of c-56, yielding compound 512 (18.86 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 716.2231 (theoretical value: 716.2212). Theoretical elemental content (%) C 50 H 28N4O2: C, 83.78; H, 3.94; N, 7.82. Measured elemental content (%): C, 83.80; H, 3.92; N, 7.85.

[0334] Synthesis Example 20: Preparation of Compound 550

[0335]

[0336] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-550, and c-329 was replaced with an equimolar amount of c-550 to obtain compound 550 (17.10 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 749.1718 (theoretical value: 749.1708). Theoretical elemental content (%) C 49 H 27 N5S2: C, 78.48; H, 3.63; N, 9.34. Measured elemental content (%): C, 78.49; H, 3.66; N, 9.30.

[0337] Synthesis Example 21: Preparation of Compound 600

[0338]

[0339] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-600, b-329 was replaced with an equimolar amount of b-600, and c-329 was replaced with an equimolar amount of c-56, yielding compound 600 (19.01 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 844.2985 (theoretical value: 844.2997). Theoretical elemental content (%) C 62 H 28 D6N2O2: C, 88.13; H, 4.77; N, 3.32. Measured elemental content (%): C, 88.11; H, 4.79; N, 3.29.

[0340] Synthesis Example 22: Preparation of Compound 629

[0341]

[0342] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-629, and c-329 was replaced with an equimolar amount of c-629 to obtain compound 629 (20.36 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 920.2330 (theoretical value: 920.2320). Theoretical elemental content (%) C 66 H 36N2S2: C, 86.06; H, 3.94; N, 3.04. Measured elemental content (%): C, 86.09; H, 3.90; N, 3.06.

[0343] Synthesis Example 23: Preparation of Compound 661

[0344]

[0345] Preparation of intermediate A-661

[0346] Under nitrogen protection, a-661 (19.55 g, 90 mmol), b-329 (14.63 g, 45.00 mmol), and sodium tert-butoxide (12.97 g, 135.00 mmol) dissolved in 450 mL of toluene were added to a reaction flask. Pd(OAc)₂ (0.30 g, 1.35 mmol) and BINAP (0.84 g, 1.35 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5.5 h. After the reaction was complete, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the obtained solid using toluene / ethanol at an 8:1 ratio to give intermediate A-661 (20.98 g, yield 78%); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 597.2224 (theoretical value: 597.2205).

[0347] Preparation of compound 661

[0348] Under nitrogen protection, C-56 (11.57 g, 40.00 mmol), A-661 (23.91 g, 40.00 mmol), and sodium tert-butoxide (5.77 g, 60.00 mmol) dissolved in 180 mL of toluene were added to a reaction flask with stirring. Pd₂(dba)₃ (0.37 g, 0.40 mmol) and X-Phos (0.38 g, 0.80 mmol) were then added. The mixture of the above reactants was heated under reflux for 6.5 h. After the reaction was complete, the mixture 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. Recrystallization from toluene yielded compound 661 (25.42 g, 76% yield). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 836.2954 (theoretical value: 836.2940). Theoretical elemental content (%) C 62 H 36 N4: C, 88.97; H, 4.34; N, 6.69. Measured elemental content (%): C, 88.98; H, 4.36; N, 6.72.

[0349] Synthesis Example 24: Preparation of Compound 793

[0350]

[0351] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-793, c-329 was replaced with an equimolar amount of c-793, and c-56 was replaced with an equimolar amount of c-783, yielding compound 793 (19.43 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 840.3355 (theoretical value: 840.3348). Theoretical elemental content (%) C 56 H 25 D 10 F5N2: C, 79.98; H, 5.39; N, 3.33. Measured elemental content (%): C, 79.96; H, 5.42; N, 3.34.

[0352] Synthesis Example 25: Preparation of Compound 811

[0353]

[0354] According to the preparation method in Synthesis Example 11, a-259 was replaced with an equimolar amount of a-811, and c-259 was replaced with an equimolar amount of c-811 to obtain compound 811 (16.67 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 830.3130 (theoretical value: 830.3117). Theoretical elemental content (%) C 61 H 42 N₂Si: C, 88.16; H, 5.09; N, 3.37. Measured elemental content (%): C, 88.14; H, 5.11; N, 3.39.

[0355] Synthesis Example 26: Preparation of Compound 833

[0356]

[0357] According to the preparation method in Synthesis Example 14, a-329 was replaced with an equimolar amount of a-833, and c-329 was replaced with an equimolar amount of c-56, yielding compound 833 (18.47 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 820.3454 (theoretical value: 820.3442). Theoretical elemental content (%) C 60 H 28 D8N4: C, 87.78; H, 5.40; N, 6.82. Measured elemental content (%): C, 87.77; H, 5.38; N, 6.84.

[0358] Synthesis Example 27: Preparation of Compound 850

[0359]

[0360] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-850, c-329 was replaced with an equimolar amount of c-850, and c-56 was replaced with an equimolar amount of d-850, yielding compound 850 (22.50 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 932.4137 (theoretical value: 932.4130). Theoretical elemental content (%) C 71 H 52 N2: C, 91.38; H, 5.62; N, 3.00. Measured elemental content (%): C, 91.40; H, 5.60; N, 3.04.

[0361] Synthesis Example 28: Preparation of Compound 861

[0362]

[0363] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-861, c-329 was replaced with an equimolar amount of c-861, and d-56 was replaced with an equimolar amount of d-861, yielding compound 861 (15.99 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 786.3958 (theoretical value: 786.3974). Theoretical elemental content (%) C 59 H 50 N2: C, 90.04; H, 6.40; N, 3.56. Measured elemental content (%): C, 90.06; H, 6.38; N, 3.54.

[0364] Synthesis Example 29: Preparation of Compound 910

[0365]

[0366] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-910, and c-329 was replaced with an equimolar amount of c-910 to obtain compound 910 (17.62 g). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 772.2530 (theoretical value: 772.2515). Theoretical elemental content (%) C 58 H 32 N₂O: C, 90.13; H, 4.17; N, 3.62. Measured elemental content (%): C, 90.15; H, 4.20; N, 3.64.

[0367] Synthesis Example 30: Preparation of Compound 923

[0368]

[0369] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-923, and c-329 was replaced with an equimolar amount of c-923 to obtain compound 923 (18.05 g). HPLC analysis showed that the solid purity was ≥99.99%. Mass spectrometry m / z: 801.2881 (theoretical value: 801.2892). Theoretical elemental content (%) C 58 H 35 N5: C, 86.87; H, 4.40; N, 8.73. Measured elemental content (%): C, 86.84; H, 4.38; N, 8.70.

[0370] Synthesis Example 31: Preparation of Compound 930

[0371]

[0372] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-930, c-329 was replaced with an equimolar amount of c-930, and c-56 was replaced with an equimolar amount of d-930, yielding compound 930 (19.31 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 824.3180 (theoretical value: 824.3191). Theoretical elemental content (%) C 63 H 40 N2: C, 91.72; H, 4.89; N, 3.40. Measured elemental content (%): C, 91.71; H, 4.91; N, 3.41.

[0373] Synthesis Example 32: Preparation of Compound 997

[0374]

[0375] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-997, c-329 was replaced with an equimolar amount of c-997, and c-56 was replaced with an equimolar amount of d-997, yielding compound 997 (21.25 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 931.3042 (theoretical value: 931.3021). Theoretical elemental content (%) C 68 H 41 N3S: C, 87.62; H, 4.43; N, 4.51. Measured elemental content (%): C, 87.64; H, 4.45; N, 4.48.

[0376] Synthesis Example 33: Preparation of Compound 997

[0377]

[0378] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-1020, c-329 was replaced with an equimolar amount of c-1020, and c-56 was replaced with an equimolar amount of d-1020, yielding compound 1020 (22.62 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1004.5085 (theoretical value: 1004.5070). Theoretical elemental content (%) C 76 H 64 N2: C, 90.80; H, 6.42; N, 2.79. Measured elemental content (%): C, 90.83; H, 6.39; N, 2.80.

[0379] Synthesis Example 34: Preparation of Compound 1052

[0380]

[0381] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-1052, c-329 was replaced with an equimolar amount of c-1052, and c-56 was replaced with an equimolar amount of d-1052, yielding compound 1052 (16.12 g). HPLC analysis showed a solid purity ≥ 99.98%. Mass spectrometry m / z: 687.2426 (theoretical value: 687.2423). Theoretical elemental content (%) C 49 H 29 N5: C, 85.57; H, 4.25; N, 10.18. Measured element content (%): C, 85.60; H, 4.23; N, 10.15.

[0382] Synthesis Example 35: Preparation of Compound 1153

[0383]

[0384] According to the preparation method in Synthesis Example 11, a-329 was replaced with an equimolar amount of a-1153, c-329 was replaced with an equimolar amount of c-1153, and c-56 was replaced with an equimolar amount of d-1153, yielding compound 1153 (15.60 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 707.2745 (theoretical value: 707.2733). Theoretical elemental content (%) C 50 H 25 D5N4O: C, 84.84; H, 4.98; N, 7.92. Measured elemental content (%): C, 84.80; H, 4.94; N, 7.96.

[0385] Synthesis Example 36: Preparation of Compound 1256

[0386]

[0387] According to the preparation method in Synthesis Example 2, a-47 was replaced with an equimolar amount of a-1256, and c-47 was replaced with an equimolar amount of c-1256 to obtain compound 1256 (23.68 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 767.2670 (theoretical value: 767.2685). Theoretical elemental content (%) C 54 H 33 N5O: C, 84.46; H, 4.33; N, 9.12. Measured elemental content (%): C, 84.42; H, 4.35; N, 9.16.

[0388] Device Examples

[0389] In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0390] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was ambient air at room temperature.

[0391] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s, while the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0392] Example 1: Fabrication of Organic Electroluminescent Device 1

[0393] An ITO / Ag / ITO anode is used on a glass substrate. A hole injection layer is formed by vacuum evaporating 20 nm of HT-1:HI-1 (mixed in a mass ratio of 97%:3%) on the anode. A hole transport layer is formed by vacuum evaporating 120 nm of compound 47 on the hole injection layer. A light-emitting layer is formed by vacuum evaporating 35 nm of RH-1:RH-2:RD-1 (mixed in a mass ratio of 48%:48%:4%) on the hole transport layer. An electron transport layer is formed by vacuum evaporating 20 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) on the light-emitting layer. A hole blocking layer is formed by vacuum evaporating 5 nm of HB-1 on the electron transport layer. An electron injection layer is formed by vacuum evaporating 1.0 nm of LiF on the hole blocking layer. A cathode is formed by vacuum evaporating 10 nm of Mg and Ag (mass ratio of 1:9) on the electron injection layer. A capping layer is formed by vacuum evaporating 80 nm of compound CP-1 on the cathode.

[0394] Examples 2-35: Fabrication of Organic Electroluminescent Devices 2-35

[0395] Replacing compound 47 in the hole transport layer of Example 1 with compounds 56, 68, 76, 78, 85, 120, 203, 212, 259, 296, 319, 329, 334, 455, 478, 483, 512, 550, 600, 629, 661, 793, 833, 850, 811, 861, 910, 923, 930, 997, 1020, 1052, 1153, and 1256 respectively, while keeping other steps the same, organic electroluminescent devices 2-35 are obtained.

[0396] Comparative Examples 1-2: Fabrication of Comparative Organic Electroluminescent Devices 1-2

[0397] By replacing compound 47 in the hole transport layer of Example 1 with R-1 and R-2 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1-2 were obtained.

[0398]

[0399] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 35 and Comparative Examples 1 to 2 of this invention are shown in Table 1.

[0400] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0401]

[0402]

[0403] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0404] As can be seen from the results in Table 1, when the carbazole-containing compound described in this invention is applied to the hole transport layer of an organic electroluminescent device, the luminous efficiency and lifespan of the device are greatly improved.

[0405] Example 36: Fabrication of Organic Electroluminescent Device 36

[0406] An ITO / Ag / ITO anode is formed on a glass substrate. A hole injection layer is formed by vacuum evaporating 20 nm of HT-1:HI-1 (mixed at a mass ratio of 97%:3%) on the anode. A hole transport layer is formed by vacuum evaporating 120 nm of HT-1 on the hole injection layer. A light-emitting layer is formed by vacuum evaporating 35 nm of compound 47:GH-1:GD-1 (mixed at a mass ratio of 46%:46%:4%) on the hole transport layer. A hole blocking layer is formed by vacuum evaporating 5 nm of HB-1 on the light-emitting layer. An electron transport layer is formed by vacuum evaporating 25 nm of ET-1:LiQ (mixed at a mass ratio of 1:1) on the hole blocking layer. An electron injection layer is formed by vacuum evaporating 1.0 nm of LiF on the electron transport layer. A cathode is formed by vacuum evaporating 10 nm of Mg and Ag (mass ratio of 1:9) on the electron injection layer. An 80 nm CP-1 capping layer is formed on the cathode.

[0407] Examples 36-70: Fabrication of Organic Electroluminescent Devices 36-70

[0408] In Example 26, compound 47 in the luminescent layer was replaced with compounds 56, 68, 76, 78, 85, 120, 203, 212, 259, 296, 319, 329, 334, 455, 478, 483, 512, 550, 600, 629, 661, 793, 833, 850, 811, 861, 910, 923, 930, 997, 1020, 1052, 1153, and 1256, respectively. All other steps remained the same, resulting in organic electroluminescent devices 36–70.

[0409] Comparative Examples 3-4: Fabrication of Comparative Organic Electroluminescent Devices 3-4

[0410] By replacing compound 47 in the light-emitting layer of Example 36 with R-3 and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 3-4 were obtained.

[0411]

[0412] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 36-70 and Comparative Examples 3-4 of this invention are shown in Table 2.

[0413] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0414]

[0415]

[0416] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0417] As can be seen from the results in Table 2, compared with Comparative Examples 3-4, when the carbazole-containing compound of the present invention is applied to the light-emitting layer of an organic electroluminescent device, the luminous efficiency and lifespan of the device are greatly improved. The compound of the present invention is a high-performance light-emitting layer material.

[0418] Example 71: Fabrication of Organic Electroluminescent Device 71

[0419] An ITO / Ag / ITO layer is used as the anode on a glass substrate. A hole injection layer is formed by vacuum evaporating 25 nm of HT-1:HI-1 (mixed at a mass ratio of 97%:3%) on the anode. A hole transport layer is formed by vacuum evaporating 115 nm of HT-1 on the hole injection layer. A light-emitting layer is formed by vacuum evaporating 35 nm of BH-1:BD-1 (mixed at a mass ratio of 97%:3%) on the hole transport layer. A hole blocking layer is formed by vacuum evaporating 5 nm of HB-2 on the light-emitting layer. An electron transport layer is formed by vacuum evaporating 30 nm of ET-1:LiQ (mixed at a mass ratio of 1:1) on the hole blocking layer. An electron injection layer is formed by vacuum evaporating 1.0 nm of LiF on the electron transport layer. A cathode is formed by vacuum evaporating 10 nm of Mg and Ag (mass ratio of 1:9) on the electron injection layer. An 80 nm layer of compound 47 is formed on the cathode.

[0420] Examples 72-105: Fabrication of Organic Electroluminescent Devices 72-105

[0421] Replacing compound 47 in the capping layer of Example 71 with compounds 56, 68, 76, 78, 85, 120, 203, 212, 259, 296, 319, 329, 334, 455, 478, 483, 512, 550, 600, 629, 661, 793, 833, 850, 811, 861, 910, 923, 930, 997, 1020, 1052, 1153, and 1256, respectively, while following the same other steps, organic electroluminescent devices 72-105 are obtained.

[0422] Comparative Examples 5-6: Fabrication of Comparative Organic Electroluminescent Devices 5-6

[0423] By replacing compound 47 in the capping layer of Example 71 with R-5 and R-6 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 5-6 were obtained.

[0424]

[0425] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 71-105 and Comparative Examples 5-6 of this invention are shown in Table 3.

[0426] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0427]

[0428]

[0429] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0430] As can be seen from the results in Table 3, when the star-shaped triamine compounds described in this invention are applied to the capping layer of organic electroluminescent devices, the luminous efficiency and lifespan of the devices are greatly improved.

[0431] In summary, the carbazole-containing compounds provided by this invention are a class of high-performance OLED materials with excellent application prospects.

[0432] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A carbazole-containing compound, characterized in that, Having the general formula shown in Equation 1-1 or Equation 1-2, The Ar1 is selected from the group shown in Formula 2; The x atoms that are the same or different are selected from C(R1) or N atoms, and the x atoms at the bonding site are selected from C; The R1s, whether identical or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C36 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C6-C30 heteroaryl, or the R1s may serve as a linking site bonded to L1, or two adjacent R1s may bond to each other to form a substituted or unsubstituted ring. The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following; The R a R b R c R d R f R g The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond together to form substituted or unsubstituted rings, or the R a R b R c R d R f R g Any one of them can be used as a connection site to bond with L1; The R h Selected from one of hydrogen, deuterium, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl groups, or the R group. h It serves as a connection site and bonds to L1; The z atoms are selected from C(R0) or N atoms, and the z atoms at the bonding sites are selected from C. The same or different R0s are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 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, or two adjacent R0s are bonded to each other to form a substituted or unsubstituted ring; The Ar2 is selected from any one of the following groups or combinations thereof: The t atoms are selected from CH or N atoms, and the t atoms at the bonding sites are selected from C atoms; The T1 is selected from O atoms, S atoms, C (R3R4) or N (R5) in the same or different ways; The T2 is independently selected from O atoms, S atoms, or N(R6); T3 and T4 are independently selected from O atoms or S atoms; The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups; The ring B is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups. The R 222 The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group; The R2s, whether identical or different, are selected from one of the following: deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R2s bonded together to form a substituted or unsubstituted ring. R3 and R4 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or R3 and R4 may be interconnected to form substituted or unsubstituted rings; R5 and R6 are independently selected from any one of hydrogen, deuterium, 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 combinations thereof; The b1 is selected from 1, 2, 3, 4, or 5; the b5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b2 is selected from 0, 1, 2, 3, or 4; the b3 is selected from 0, 1, or 2; the b4 is selected from 0, 1, 2, or 3; the b 14 Selected from 0, 1, 2, 3, 4, or 5; b 15 Choose from 1, 2, 3, or 4; The Ar3 is selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl groups, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 alicyclic groups, and R. 777 Substituted phenyl, R 777 Substituted biphenyl, R 777 The group consisting of any one of the following: substituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted C7-C30 fused aryl, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused cycloalcohol, substituted or unsubstituted C2-C30 heteroaryl, or any one of the groups shown in Formula 2. The R 777 The same or different are selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted C1 to C20 alkyl group, and substituted or unsubstituted C3 to C20 alicyclic group; The Ar4 is selected from any one of the groups shown below or the group shown in Formula 2. The q atoms are selected from CH or N atoms, and the q atoms at the bonding sites are selected from C. The M1 is selected from O atoms, S atoms, C(R) atoms, or different atoms. 30 R 40 ) or N(R 50 ); The M2 is independently selected from O atoms, S atoms, or N(R) atoms. 60 ); M3 and M4 are independently selected from O atoms or S atoms; The ring M is selected from substituted or unsubstituted C3-C15 alicyclic groups; The ring N is selected from any one of substituted or unsubstituted C9-C30 fused aryl groups and substituted or unsubstituted C3-C30 fused heteroaryl groups; The R P The same or different from one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused polycyclic group, substituted or unsubstituted C2-C30 heteroaryl; The R 30 R 40 Independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or the R 30 and R 40 They can connect with each other to form substituted or unsubstituted rings; The R 50 R 60 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n4 is selected from 0, 1, 2, 3, or 4; the n5 is selected from 0, 1, or 2; the n6 is selected from 0, 1, 2, or 3; and the n7 is selected from 0, 1, 2, 3, 4, 5, or 6. L1, L2, L3, and L4 are 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 cycloalcohol, and substituted or unsubstituted C2-C30 heteroarylene.

2. The carbazole-containing compound according to claim 1, characterized in that, The Ar1 is selected from any of the following structures: The x atoms that are the same or different are selected from C(R1) or N atoms, and the x atoms at the bonding site are selected from C; R1 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl Anthracene, phenanthrene, triphenylene, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, indolyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R1s are connected to each other to form substituted or unsubstituted rings; The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following; The R a R b R c R d R f R g The same or different from the following groups selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene. The following are some of the following: phenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond with each other to form substituted or unsubstituted rings; The R h Selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene The substituents are any one or more of the following: yl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzimidazolyl, benzothiazolyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other.

3. The carbazole-containing compound according to claim 1, characterized in that, The Ar1 is selected from any of the following structures: R1 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, indole, furfural. Any one or more of the following: uryl, thiophenyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilane, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring; The Y is selected from single bonds, O atoms, S atoms, Se atoms, C(R) atoms, O atoms, S ... a R b ), Si(R) c R d ), Ge(R) f R g ), N(R h Any one of the following; The R a R b R c R d R f R g The same or different from the following groups selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene. The following are some of the following: phenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or R a and R b They bond together to form substituted or unsubstituted rings, or R c and R d They bond together to form substituted or unsubstituted rings, or R f and R g They bond with each other to form substituted or unsubstituted rings; The R h Selected from hydrogen, deuterium, and the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, adamantane, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene The substituents are any one or more of the following: yl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzimidazolyl, benzothiazolyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents may be the same as or different from each other; The a is selected from 0, 1, 2, 3 or 4; the a1 is selected from 0, 1, 2 or 3; the a2 is selected from 0, 1 or 2; the a3 is selected from 0, 1, 2, 3, 4, 5 or 6; the a4 is selected from 0, 1, 2, 3, 4 or 5.

4. The carbazole-containing compound according to claim 1, characterized in that, The Ar2 group is selected from any one of the following groups: The R2, R 22 The following groups, selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene. The following are any one or more of pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other, or the two adjacent R2s are connected to each other to form a substituted or unsubstituted ring; R5 and R6 are selected, either identically or differently, from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazole, silyl, where, when substituted by multiple substituents, the multiple substituents are identical or different from each other; The b1 is independently selected from 1, 2, 3, 4, or 5; the b2 is independently selected from 0, 1, 2, 3, or 4; the b3 is independently selected from 0, 1, or 2; the b4 is independently selected from 0, 1, 2, or 3; the b5 is independently selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 6; the b7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the b 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; the b 12 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the b 13 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15; the b 14 Selected from 0, 1, 2, 3, 4, or 5; b 15 Choose independently from 1, 2, 3 or 4.

5. The carbazole-containing compound according to claim 1, characterized in that, The Ar3 is selected from any one of the following groups: deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic, or combinations thereof: The E1 is selected from O atoms, S atoms, C (R8R9) or N (R 10 ); The E2 is independently selected from O atoms, S atoms, or N(R) atoms. 11 ); E3 and E4 are independently selected from O atoms or S atoms; The ring D is selected from substituted or unsubstituted C3-C15 alicyclic groups; The P is selected from N or CH; the P at the bonding site is selected from C; The R7s are selected from any of the following groups, whether identical or different: deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or adjacent R7s may be interconnected to form substituted or unsubstituted rings. The R 777 The following groups, selected from deuterium, halogen, cyano, nitro, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopentenyl, cyclohexenyl, cycloheptenyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, and any one or more of these groups, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other; R8 and R9 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; or R8 and R9 may be interconnected to form substituted or unsubstituted rings; The R 10 R 11 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, or combinations thereof; The d1 is selected from 1, 2, 3, 4, or 5; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the d9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the d2 is selected from 0, 1, 2, 3, or 4; the d3 is selected from 0, 1, or 2; the d4 is selected from 0, 1, 2, or 3; the d 14 Selected from 0, 1, 2, 3, 4, or 5; the d 15 Choose from 1, 2, 3, or 4.

6. The carbazole-containing compound according to claim 1, characterized in that, The Ar4 is selected from any of the following groups or the groups shown in Formula 2: The R p R pp The following groups, selected from deuterium, cyano, halogen, nitro, substituted or unsubstituted, may be the same or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, di... The substituents are any one or more of the following: hydronaphthyl, anthraceneyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, indolyl, furanyl, thienyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, benzooxazolyl, benzothiazolyl, carbazoleyl, and silyl, wherein, when substituted with multiple substituents, the multiple substituents are the same or different from each other; The R 50 R 60 The following groups, selected from hydrogen, deuterium, substituted or unsubstituted, may be identical or different: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, indolyl, furanyl, thiophene, benzoxazolyl, benzothiazolyl, carbazole, and silyl, wherein, when substituted by multiple substituents, the multiple substituents may be identical or different from each other; The n1 is selected from 0, 1, 2, 3, 4, or 5; the n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n4 is selected from 0, 1, 2, 3, or 4; the n5 is selected from 0, 1, or 2; the n6 is selected from 0, 1, 2, or 3; the n7 is selected from 0, 1, 2, 3, 4, 5, or 6; the n8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the n9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the n 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the n 11 Select independently from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

7. The carbazole-containing compound according to claim 1, characterized in that, The L1, L2, L3, and L4 are independently selected from any one of the following groups or combinations thereof: The i that are the same or different are selected from C(R) 16 ) or N, the R 16 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 16 They can connect with each other to form substituted or unsubstituted rings; The Q3 is independently selected from O atoms, S atoms, C(R) atoms, and S atoms. 17 R 18 ) or N(R 19 ); The Q4 is independently selected from O atoms, S atoms, or N(R) atoms. 20 ); The ring F is selected from substituted or unsubstituted C3-C15 alicyclic groups; The R 17 R 18 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 17 and R 18 They can connect with each other to form substituted or unsubstituted rings; The R 19 R 20 It is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C18 heteroaryl, and substituted or unsubstituted silyl.

8. The carbazole-containing compound according to claim 1, characterized in that, The carbazole-containing compounds represented by Formula 1-1 or Formula 1-2 are selected from any of the following chemical structures:

9. 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, characterized in that, The organic layer contains a carbazole-containing compound as described in any one of claims 1 to 8.

10. The organic electroluminescent device according to claim 9, characterized in that, The organic layer is located between the anode and the cathode or on the outside of one or more electrodes, the organic layer comprising at least one of a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, characterized in that at least one of the hole transport region, the light-emitting layer, and the capping layer contains a carbazole-containing compound as described in any one of claims 1 to 8.

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