A compound containing a carbazole group and an organic electroluminescent device thereof

Abstract

The application provides a compound containing a carbazole group and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The compound of chemical formula 1 has a high triplet energy level and a high hole mobility, can be applied to a hole transport region in an organic electroluminescent device, and improves the hole transport efficiency; meanwhile, the compound has good thermal stability.When the compound is applied to a hole transport material of the organic electroluminescent device, the driving voltage of the device can be effectively reduced, the luminous efficiency of the device is improved, the stability of the device is increased, and the service life of the device is prolonged.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a compound containing a carbazole group and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diode (OLED) displays, as a new generation of flat panel displays, possess characteristics such as self-illumination, wide viewing angle, short response time, high luminous efficiency, wide color gamut, low operating voltage, thin panel, flexible size and shape design, and simple fabrication methods, and also have the potential for low cost. They are hailed as the star flat panel display product of the 21st century and are referred to by industry insiders as "dream displays." With the continuous development of organic light-emitting technology, significant human and material resources have been invested in research on materials, device structures, and processes, resulting in substantial progress, and some research results have been successfully commercialized. Therefore, the development of a series of novel organic electroluminescent materials is particularly important.

[0003] OLEDs typically consist of an anode, a cathode, and an organic layer. The organic layer of an OLED can include a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, an electron injection layer, and a capping layer. The hole transport layer, acting as the connecting layer between the anode and the emissive layer, plays two main roles: first, it facilitates the transport of holes injected from the anode to the emissive layer and, to some extent, blocks the diffusion of electrons from the emissive layer to the hole transport layer, thus better confining electrons within the emissive layer and maximizing carrier recombination; second, it simultaneously lowers the energy barrier during hole injection, improving hole injection efficiency and thereby enhancing the device's brightness, efficiency, and lifetime. However, traditionally used hole transport materials, due to their low HOMO values ​​and triplet energy levels, cause charge imbalances within the emissive layer, resulting in unsatisfactory luminous efficiency and hindering their application and development in fields such as OLEDs. Furthermore, the low glass transition temperature of the hole transport layer materials significantly reduces the device's lifetime. Therefore, it is essential to design a hole transport material with good film-forming properties and thermal stability, high HOMO value and triplet energy level, high hole transport rate, and electron blocking capability.

[0004] As far as China's OLED industry is concerned, OLED is still in its early stages and has many shortcomings in terms of driving voltage, luminous efficiency and lifespan. Therefore, more investment is needed in basic research to continuously develop and synthesize more efficient organic electroluminescent materials. Summary of the Invention

[0005] To address the aforementioned problems in the prior art, this invention provides a compound containing a carbazole group, which can effectively reduce the driving voltage of organic light-emitting devices (OLEDs) and improve their luminous efficiency and lifespan. Specifically, the technical solution of this invention is as follows:

[0006] Specifically, the present invention provides a compound containing a carbazole group, wherein the compound containing the carbazole group has the structure of chemical formula 1.

[0007]

[0008] The Ra is selected from Si(R0)3;

[0009] The R0, whether identical or different, is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, and substituted or unsubstituted C6-C30 aryl groups; the m is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0010] The Rb is selected from any one or a combination of deuterium, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted camphene; when there are two or more Rb, the two or more Rb are the same or different from each other; the n is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

[0011] The Ar is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, and substituted or unsubstituted C6-C30 aryl groups;

[0012] The Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups;

[0013] The L0, L1, and L2 are the same or different and are selected from any one of the single-bonded, substituted or unsubstituted C6 to C30 aryl groups;

[0014] The R1 and R2, whether identical or different, are selected from any one or a combination of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, or two adjacent R1s connected to each other to form a substituted or unsubstituted ring, or two adjacent R2s connected to each other to form a substituted or unsubstituted ring; a is selected from 0, 1, 2, 3 or 4; b is selected from 0, 1, 2 or 3.

[0015] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode and an organic layer located between the anode and the cathode, the organic layer comprising a hole transport region, a light-emitting layer and an electron transport region, wherein the hole transport region comprises any one or more of the carbazole-containing compounds described in the present invention.

[0016] Beneficial effects

[0017] This invention provides a carbazole-containing compound that possesses suitable HOMO energy levels and a high triplet energy level, exhibiting high hole transport efficiency. Furthermore, this compound has a high glass transition temperature and decomposition temperature, resulting in good film-forming properties. The carbazole-containing compound provided by this invention can effectively reduce the driving voltage of organic light-emitting diodes (OLEDs), improve the luminous efficiency of OLEDs, and extend their lifespan. Detailed Implementation

[0018] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0019] In this specification, "*" indicates a portion connected to another substituent. "*" can be attached to any optional position of the group / fraction to which it is attached.

[0020] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site 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.

[0021] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0022] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0023] The alkyl group referred to in this invention is a general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.

[0024] The cycloalkyl group described in this invention refers to the collective term for monovalent groups remaining after removing one hydrogen atom from a cyclic alkane molecule, preferably having 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, etc.

[0025] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.

[0026] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.

[0027] The “substituted or unsubstituted silyl group” as described in this invention refers to the -Si(R)3 group, wherein each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted of the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenyl, phenyl, biphenyl, naphthyl.

[0028] The substituents described in the "substituted or unsubstituted" of this invention may be independently selected from deuterium, cyano, nitro, amino, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, but are not limited thereto, or adjacent substituents may be linked to form a ring. Preferred compounds include deuterium, cyano, nitro, amino, halogen, C1-C12 alkyl, C3-C12 cycloalkyl, C1-C30 silyl, and C6-C30 aryl. Specific examples may include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphene, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl. Tert-butyldimethylsilyl, ethyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, trinaphthylsilyl, tolyl, mesitylene, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, perylene, pyrene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, etc., but not limited to these. Alternatively, when there are multiple substituents, the multiple substituents may be the same or different from each other; or adjacent substituents may be linked to form a ring.

[0029] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:

[0030]

[0031] 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 both. 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 seven-membered ring, or a fused ring. Specific examples of aromatic ring systems may include benzene, naphthalene, anthracene, phenanthrene, or pyrene, but are not limited thereto. Specific examples of aliphatic ring systems may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutene, cyclopentene, or cyclohexene, but are not limited thereto. Specific examples of fused ring systems formed by both aromatic and aliphatic rings may include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutene, benzocyclopentene, or benzocyclohexene, but are not limited thereto.

[0032] This invention provides a compound containing a carbazole group, wherein the compound containing the carbazole group has the structure of chemical formula 1.

[0033]

[0034] The Ra is selected from Si(R0)3;

[0035] The R0, whether identical or different, is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, and substituted or unsubstituted C6-C30 aryl groups; the m is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0036] The Rb is selected from any one or a combination of deuterium, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted camphene; when there are two or more Rb, the two or more Rb are the same or different from each other; the n is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

[0037] The Ar is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, and substituted or unsubstituted C6-C30 aryl groups;

[0038] The Ar1 and Ar2 are independently selected from substituted or unsubstituted C6-C30 aryl groups;

[0039] The L0, L1, and L2 are the same or different and are selected from any one of the single-bonded, substituted or unsubstituted C6 to C30 aryl groups;

[0040] The R1 and R2, whether identical or different, are selected from any one or a combination of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, or two adjacent R1s connected to each other to form a substituted or unsubstituted ring, or two adjacent R2s connected to each other to form a substituted or unsubstituted ring; a is selected from 0, 1, 2, 3 or 4; b is selected from 0, 1, 2 or 3.

[0041] Preferably, Ra is selected from any one of the following groups:

[0042]

[0043]

[0044] The R3s, whether identical or different, are selected from any one or a combination thereof, of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl; when two or more R3s are present, the two or more R3s are identical or different from each other, or two adjacent R3s are connected to each other to form a substituted or unsubstituted ring;

[0045] The same or different c1 is selected from 0, 1, 2, 3, 4 or 5; the same or different c2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the same or different c3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the same or different c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the same or different c5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13.

[0046] Preferably, the same or different R3 is selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, butyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, tert-butyldimethylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, etc.

[0047] Preferably, the Rb is selected from deuterium or any of the following groups derived from substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, or substituted or unsubstituted camphenyl groups.

[0048]

[0049]

[0050] The R4 is selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutyl... The alkyl group, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, or any combination thereof; when two or more R4s are present, the two or more R4s are the same as or different from each other, or two adjacent R4s are connected to each other to form a substituted or unsubstituted ring;

[0051] The d is selected from 0, 1, 2, 3, 4 or 5.

[0052] Preferably, the Ar1-(Ra)m is selected from any one of the following groups:

[0053]

[0054] The R5s, whether identical or different, are selected from any one or a combination thereof, of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl; when two or more R5s are present, the two or more R5s are identical or different from each other, or two adjacent R5s are connected to each other to form a substituted or unsubstituted ring;

[0055] The value of e1 is selected from 0, 1, 2, 3, or 4; the value of e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the value of e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the value of e4 is selected from 0, 1, 2, 3, 4, or 5; the value of e5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; and the value of e1 is selected from 0, 1, 2, or 3.

[0056] The m1 is selected from 1, 2, 3, 4 or 5; the m2 is selected from 1, 2, 3, 4, 5, 6 or 7; the m3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the m4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the m5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the m6 is selected from 1, 2 or 3; the m7 is selected from 1, 2, 3 or 4.

[0057] Preferably, R5 is the same as or different from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl alkyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0058] The substituents in "substituted or unsubstituted" are selected from any one or a combination of hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl.

[0059] Preferably, the Ar2-(Rb)n is selected from any one of the following groups:

[0060]

[0061] The R6s, whether identical or different, are selected from any one or a combination thereof, of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl; when two or more R6s are present, the two or more R6s are identical or different from each other, or two adjacent R6s are connected to each other to form a substituted or unsubstituted ring;

[0062] The Rc and Rd are the same or different and are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, or Rc and Rd are connected to each other to form a substituted or unsubstituted spirocycle.

[0063] The same or different f1 is selected from 0, 1, 2, 3 or 4; the same or different f2 is selected from 0, 1, 2, 3, 4, 5 or 6; the same or different f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the same or different f4 is selected from 0, 1, 2 or 3; the same or different f5 is selected from 0, 1, 2, 3, 4 or 5; the same or different f6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0064] The n1 is selected from 1, 2, 3, 4 or 5; the n2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the n3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the n4 is selected from 1, 2, 3, 4, 5, 6 or 7; the n5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and the n6 is selected from 1, 2 or 3.

[0065] Preferably, the R6 groups, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, benzoyl... Borneol, phenyl, biphenyl, naphthyl, phenanthrene, phenylenetriene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc., or two adjacent R6s connected to each other to form substituted or unsubstituted benzene rings, naphthyl rings, or C4-C7 aliphatic rings.

[0066] Preferably, the same or different Rc and Rd are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0067] More preferably, the same or different Rc and Rd are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0068] Preferably, when Rb is selected from deuterium, one or more of R6 are selected from deuterium.

[0069] Preferably, when Rb is selected from deuterium, R6 is selected from deuterium.

[0070] Preferably, one, two, or three of Rb are selected from substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, or substituted or unsubstituted camphenyl.

[0071] Preferably, when Rb is selected from substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, or substituted or unsubstituted camphenyl, m is selected from 1, 2, or 3, more preferably 1.

[0072] More preferably, the Ar2-(Rb)n is selected from any one of the following groups:

[0073]

[0074]

[0075]

[0076]

[0077] Preferably, the Ar is selected from any one of the following groups:

[0078]

[0079] The R7s, whether identical or different, are selected from any one or a combination thereof, of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl; when two or more R7s are present, the two or more R7s are identical or different from each other, or two adjacent R7s are connected to each other to form a substituted or unsubstituted ring;

[0080] The k1 that is the same or different is selected from 0, 1, 2, 3, 4 or 5; the k2 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the k3 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the k4 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the k5 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the k6 that is the same or different is selected from 0, 1, 2, 3 or 4; the k7 that is the same or different is selected from 0, 1, 2 or 3; the k8 that is the same or different is selected from 0, 1 or 2; the k9 that is the same or different is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the k0 that is the same or different is selected from 0, 1, 2, 3, 4, 5 or 6.

[0081] Preferably, the R7 groups, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl alkyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0082] More preferably, the Ar is selected from any one of the following groups:

[0083]

[0084] The same or different p1 is selected from 0, 1, 2, 3, 4 or 5; the same or different p2 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the same or different p3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the same or different p4 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0085] Preferably, L0, L1, and L2, whether the same or different, are selected from single bonds or any of the following groups:

[0086]

[0087] The R8s, whether identical or different, are selected from any one or a combination thereof, of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl; when two or more R8s are present, the two or more R8s are identical or different from each other, or two adjacent R8s are connected to each other to form a substituted or unsubstituted ring;

[0088] The same or different q1 is selected from 0, 1, 2, 3 or 4; the same or different q2 is selected from 0, 1, 2, 3, 4, 5 or 6; the same or different q3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the same or different q4 is selected from 0, 1 or 2; the same or different q5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the same or different q6 is selected from 0, 1, 2, 3, 4 or 5.

[0089] Preferably, the R8 groups, whether identical or different, are selected from hydrogen, deuterium, cyano, halogen, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or substituted or unsubstituted groups of the following: methyl, ethyl, propyl, butyl, cyclopropyl. alkyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0090] Preferably, R1 and R2, whether the same or different, are selected from hydrogen, deuterium, halogen, cyano, methyl, ethyl, propyl, butyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, naphthyl, phenanthrene, phenylenetriene, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirodifluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, etc.

[0091] Most preferably, the carbazole-containing compound is selected from any one of the structures shown below.

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109] The above lists some specific structural forms of compounds containing carbazole groups represented by chemical formula 1 according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula 1, with substituents as defined above, should be included.

[0110] The present invention also provides an organic electroluminescent device comprising at least one of the carbazole-containing compounds described in the present invention.

[0111] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer contains at least one of the carbazole-containing compounds described in this invention.

[0112] Preferably, the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode. The hole transport region contains at least one of the carbazole-containing compounds described in this invention.

[0113] Preferably, the hole transport region comprises a hole injection layer and a hole transport layer, the hole injection layer being located between the anode and the hole transport layer, the hole transport layer being located between the hole injection layer and the light-emitting layer, and the hole transport layer comprising at least one of the carbazole-containing compounds of the present invention.

[0114] Preferably, the organic layer includes a hole transport region, the hole transport region includes a hole transport layer, the hole transport layer includes a hole transport material, and the hole transport material includes at least one of the carbazole-containing compounds of the present invention.

[0115] 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 functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0116] The anode of this invention is preferably made of a material with a high work function. The anode includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited thereto. The hole injection layer material of this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene, etc.

[0117] The hole injection layer material described in this invention may include triphenylamine-containing polyether ketone (TPAPEK), 4-isopropyl-4'-methyldiphenyliodonium tetra(pentafluorophenyl)borate (PPBI), N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (DNTPD), copper phthalocyanine (II) (abbreviated as CuPc), 4,4',4”-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 2,3,6,7 Examples of suitable materials for hole injection layers include, but are not limited to, 10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), 4,4',4”-tris{N,N-diphenylamino}triphenylamine (TDATA), and 4,4',4”-tris(N,N-2-naphthylphenylamino)triphenylamine (2-TNATA). The structure can be a single substance or a single-layer or multi-layer structure formed by different substances. In addition to the above materials and their combinations, other known materials suitable for hole injection layers can also be selected.

[0118] The hole transport material described in this invention preferably possesses good hole transport performance. It can be selected from small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, and butadiene compounds, as well as polymer materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, and a carbazole-containing compound provided by this invention, but is not limited thereto. Preferably, the hole transport layer is selected from the carbazole-containing compound described in this invention. It can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances. The hole transport layer may include a single layer, or a first hole transport layer, a second hole transport layer, or more layers. One or more layers of the hole transport layer contain a carbazole-containing compound provided by this invention. The first hole transport layer is located between the hole injection layer and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer.

[0119] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material and dopants. The luminescent layer material may contain multiple host materials and multiple dopants. The dopants can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The doping ratio of the host material and the dopants can vary depending on the materials used; preferably, the doping concentration of the dopant, based on the host compound, is less than 20 wt%. Fluorescent compounds can be used as dopants, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolineazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as iridium complexes, osmium complexes, platinum complexes and other metal complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylated iridium (FIrpic), tri(2-phenylpyridine)iridium (Ir(ppy)3), acetylacetonate di(2-phenylpyridine)iridium (Ir(ppy)2(acac)), etc.

[0120] The host material of the luminescent layer needs to have bipolar charge transport properties and appropriate energy levels to effectively transfer the excitation energy to the guest luminescent material. It may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., as well as heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these.

[0121] The electron transport material described in this invention is required to have excellent electron transport performance, effectively transporting electrons from the cathode to the light-emitting layer, and possessing a high electron mobility. It may contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited to these.

[0122] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material may 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, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiO, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.

[0123] The cathode of this invention is preferably made of a material with a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, laminated materials, etc. Specific examples may include aluminum (Al), silver (Ag), lithium (Li), magnesium (Mg), magnesium:silver (Mg:Ag), etc., but are not limited to these.

[0124] The following is a method for preparing the carbazole-containing compound represented by Formula 1 of this invention, but the preparation method of this invention is not limited thereto. The core structure of the carbazole-containing compound of Formula 1 can be prepared by the reaction route shown below. The 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.

[0125] [Synthesis Route]

[0126] Preparation of compounds containing a carbazole group (Formula 1):

[0127] There are no particular limitations on the preparation method of the carbazole-containing compound shown in Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reactions, carbon-nitrogen coupling reactions, etc., are described below:

[0128] [Synthesis Route]

[0129]

[0130] Xa, Xb, and Xc are each independently selected from any one of I, Br, and Cl; the limitations of Ra, Rb, R1, R2, Ar, Ar1, Ar2, L0, L1, and L2 are the same as those described above.

[0131] 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.

[0132] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Instruments, UK); Vario ELcube organic elemental analyzer (Elementar Instruments, Germany)

[0133] [Synthesis Example]

[0134] Synthesis Example 1: Preparation of Intermediate A-84

[0135]

[0136] Under nitrogen protection, a-84 (29.54 g, 80.00 mmol), b-84 (14.08 g, 80.00 mmol), K2CO3 (19.35 g, 140.00 mmol), and 350 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. The air was then purged with nitrogen three times. Pd(PPh3)4 (0.92 g, 0.8 mmol) was then added, and the mixture was stirred at reflux for 4 h. After the reaction was complete, the reaction mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was recrystallized from toluene and dried to obtain intermediate A-84 (20.31 g, yield 75%); HPLC purity ≥ 98.87%. Mass spectrometry m / z: 338.1733 (theoretical value: 338.1721).

[0137] Synthesis Example 2: Preparation of Intermediate A-110

[0138]

[0139] According to the method in Example 1, a-84 was replaced with an equimolar amount of a-110, and b-84 was replaced with an equimolar amount of b-110 to obtain intermediate A-110 (29.19 g). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 506.2710 (theoretical value: 506.2722).

[0140] Synthesis Example 3: Preparation of Intermediate A-119

[0141]

[0142] According to the method in Example 1, a-84 was replaced with an equimolar amount of a-119, and b-84 was replaced with an equimolar amount of b-119 to obtain intermediate A-119 (22.76 g). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 384.1639 (theoretical value: 384.1626).

[0143] Synthesis Example 4: Preparation of Compound 2

[0144]

[0145] Synthetic intermediate H-2

[0146] Under nitrogen protection, toluene (300 mL), A-2 (16.72 g, 50.00 mmol), B-2 (8.10 g, 50.00 mmol), palladium acetate (0.17 g, 0.75 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), and tri-tert-butylphosphine (3 mL of 0.50 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization was performed using toluene:ethanol (10:1) to obtain intermediate H-2 (17.04 g, 82%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 415.2082 (theoretical value: 415.2097).

[0147] Synthetic compound 2

[0148] Under nitrogen protection, toluene (200 ml), intermediate H-2 (12.47 g, 30.00 mmol), C-2 (9.88 g, 30.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), and BINAP (0.30 g, 0.48 mmol) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was recrystallized from toluene to give compound 2 (14.34 g, 72%). The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrometry m / z: 663.3136 (theoretical value: 663.3118). Theoretical elemental content (%) C 47 H 33 D5N2Si: C, 85.02; H, 6.53; N, 4.22. Measured elemental content (%): C, 85.05; H, 6.52; N, 4.20.

[0149] Synthesis Example 5: Preparation of Compound 15

[0150]

[0151] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-15, B-2 with an equimolar amount of B-15, and C-2 with an equimolar amount of C-15, yielding compound 15 (18.75 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 879.4042 (theoretical value: 879.4057). Theoretical elemental content (%) C 64 H 45 D5N2Si: C, 87.33; H, 6.30; N, 3.18. Measured elemental content (%): C, 87.36; H, 6.33; N, 3.12.

[0152] Synthesis Example 6: Preparation of Compound 19

[0153]

[0154] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-19, and C-2 was replaced with an equimolar amount of C-19 to obtain compound 19 (17.15 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 761.3680 (theoretical value: 761.3670). Theoretical elemental content (%) C 52 H 43D5N2Si2: C, 81.95; H, 7.01; N, 3.68. Measured elemental content (%): C, 81.98; H, 7.03; N, 3.63.

[0155] Synthesis Example 7: Preparation of Compound 28

[0156]

[0157] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-28, and C-2 was replaced with an equimolar amount of C-28 to obtain compound 28 (15.36 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 691.3414 (theoretical value: 691.3400). Theoretical elemental content (%) C 49 H 33 D7N2Si: C, 85.05; H, 6.84; N, 4.05. Measured elemental content (%): C, 85.07; H, 6.86; N, 4.01.

[0158] Synthesis Example 8: Preparation of Compound 36

[0159]

[0160] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-36, and C-2 was replaced with an equimolar amount of C-28, yielding compound 36 (16.76 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 754.3670 (theoretical value: 754.3681). Theoretical elemental content (%) C 54 H 42 D4N2Si: C, 85.90; H, 6.67; N, 3.71. Measured elemental content (%): C, 85.93; H, 6.62; N, 3.73.

[0161] Synthesis Example 9: Preparation of Compound 47

[0162]

[0163] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-47, and C-2 was replaced with an equimolar amount of C-47, yielding compound 47 (14.59 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 639.3133 (theoretical value: 639.3118). Theoretical elemental content (%) C 45 H 33 D5N2Si: C, 84.46; H, 6.77; N, 4.38. Measured elemental content (%): C, 84.49; H, 6.78; N, 4.33.

[0164] Synthesis Example 10: Preparation of Compound 74

[0165]

[0166] Following the method of Example 4, C-2 was replaced with an equimolar amount of C-28 to obtain compound 74 (14.40 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 639.3108 (theoretical value: 639.3118). Theoretical elemental content (%) C 45 H 33 D5N2Si: C, 84.46; H, 6.77; N, 4.38. Measured elemental content (%): C, 84.49; H, 6.78; N, 4.36.

[0167] Synthesis Example 11: Preparation of Compound 84

[0168]

[0169] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-84, and C-2 was replaced with an equimolar amount of C-84, yielding compound 84 (13.91 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 643.3380 (theoretical value: 643.3369). Theoretical elemental content (%) C 45 H 29 D9N2Si: C, 83.93; H, 7.35; N, 4.35. Measured elemental content (%): C, 83.96; H, 7.33; N, 4.34.

[0170] Synthesis Example 12: Preparation of Compound 89

[0171]

[0172] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-89, and C-2 was replaced with an equimolar amount of C-28, yielding compound 89 (15.90 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 715.3420 (theoretical value: 715.3431). Theoretical elemental content (%) C 51 H 37 D5N2Si: C, 85.55; H, 6.62; N, 3.91. Measured elemental content (%): C, 85.51; H, 6.64; N, 3.93.

[0173] Synthesis Example 13: Preparation of Compound 110

[0174]

[0175] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-110, and C-2 was replaced with an equimolar amount of C-28, yielding compound 110 (17.54 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 811.4382 (theoretical value: 811.4370). Theoretical elemental content (%) C 58 H 49 D5N2Si: C, 85.77; H, 7.32; N, 3.45. Measured elemental content (%): C, 85.75; H, 7.35; N, 3.44.

[0176] Synthetic Example 14: Preparation of Compound 119

[0177]

[0178] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-119, and C-2 was replaced with an equimolar amount of C-28, yielding compound 119 (15.32 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 689.3260 (theoretical value: 689.3275). Theoretical elemental content (%) C 49 H 35 D5N2Si: C, 85.30; H, 6.57; N, 4.06. Measured elemental content (%): C, 85.33; H, 6.52; N, 4.08.

[0179] Synthesis Example 15: Preparation of Compound 129

[0180]

[0181] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-15, and C-2 was replaced with an equimolar amount of C-47, yielding compound 129 (15.17 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 639.3130 (theoretical value: 639.3118). Theoretical elemental content (%) C 45 H 33 D5N2Si: C, 84.46; H, 6.77; N, 4.38. Measured elemental content (%): C, 84.49; H, 6.75; N, 4.37.

[0182] Synthetic Example 16: Preparation of Compound 144

[0183]

[0184] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-144, and C-2 was replaced with an equimolar amount of C-144, yielding compound 144 (14.68 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 643.3359 (theoretical value: 643.3369). Theoretical elemental content (%) C 45 H 29 D9N2Si: C, 83.93; H, 7.35; N, 4.35. Measured elemental content (%): C, 83.97; H, 7.33; N, 4.33.

[0185] Synthesis Example 17: Preparation of Compound 149

[0186]

[0187] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-149, B-2 with an equimolar amount of B-15, and C-2 with an equimolar amount of C-149, yielding compound 149 (15.41 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 693.3538 (theoretical value: 693.3526). Theoretical elemental content (%) C 49 H 31 D9N2Si: C, 84.80; H, 7.11; N, 4.04. Measured elemental content (%): C, 84.83; H, 7.10; N, 4.02.

[0188] Synthesis Example 18: Preparation of Compound 168

[0189]

[0190] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-15, and C-2 was replaced with an equimolar amount of C-168, yielding compound 168 (15.14 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 681.3575 (theoretical value: 681.3588). Theoretical elemental content (%) C 48 H 39 D5N2Si: C, 84.53; H, 7.24; N, 4.11. Measured elemental content (%): C, 84.51; H, 7.22; N, 4.15.

[0191] Synthetic Example 19: Preparation of Compound 181

[0192]

[0193] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-181, B-2 with an equimolar amount of B-181, and C-2 with an equimolar amount of C-47, yielding compound 181 (14.40 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 639.3134 (theoretical value: 639.3118). Theoretical elemental content (%) C 45 H 33 D5N2Si: C, 84.46; H, 6.77; N, 4.38. Measured elemental content (%): C, 84.47; H, 6.79; N, 4.35.

[0194] Synthesis Example 20: Preparation of Compound 183

[0195]

[0196] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-15, and C-2 was replaced with an equimolar amount of C-28, yielding compound 183 (16.97 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 715.3420 (theoretical value: 715.3431). Theoretical elemental content (%) C 51 H 37 D5N2Si: C, 85.55; H, 6.62; N, 3.91. Measured elemental content (%): C, 85.50; H, 6.65; N, 3.93.

[0197] Synthesis Example 21: Preparation of Compound 200

[0198]

[0199] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-15, and C-2 was replaced with an equimolar amount of C-200, yielding compound 200 (16.33 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 715.3422 (theoretical value: 715.3431). Theoretical elemental content (%) C 51 H 37 D5N2Si: C, 85.55; H, 6.62; N, 3.91. Measured elemental content (%): C, 85.50; H, 6.64; N, 3.94.

[0200] Synthesis Example 22: Preparation of Compound 217

[0201]

[0202] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-217, B-2 with an equimolar amount of B-15, and C-2 with an equimolar amount of C-28, yielding compound 217 (16.78 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 765.3599 (theoretical value: 765.3588). Theoretical elemental content (%) C 55 H 39 D5N2Si: C, 86.23; H, 6.45; N, 3.66. Measured elemental content (%): C, 86.26; H, 6.46; N, 3.62.

[0203] Synthesis Example 23: Preparation of Compound 241

[0204]

[0205] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-241, and C-2 was replaced with an equimolar amount of C-47, yielding compound 241 (16.54 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 715.3431 (theoretical value: 715.3418). Theoretical elemental content (%) C 51 H 37 D5N2Si: C, 85.55; H, 6.62; N, 3.91. Measured elemental content (%): C, 85.51; H, 6.64; N, 3.93.

[0206] Synthesis Example 24: Preparation of Compound 291

[0207]

[0208] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-291, B-2 with an equimolar amount of B-291, and C-2 with an equimolar amount of C-291, yielding compound 291 (17.20 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 818.4042 (theoretical value: 818.4056). Theoretical elemental content (%) C 59 H 54 N₂Si: C, 86.51; H, 6.64; N, 3.42. Measured elemental content (%): C, 86.52; H, 6.61; N, 3.44.

[0209] Synthesis Example 25: Preparation of Compound 293

[0210]

[0211] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-293, B-2 with an equimolar amount of B-293, and C-2 with an equimolar amount of C-28, yielding compound 293 (17.47 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 868.4201 (theoretical value: 868.4213). Theoretical elemental content (%) C 63 H 56 N₂Si: C, 87.05; H, 6.49; N, 3.22. Measured elemental content (%): C, 87.02; H, 6.46; N, 3.28.

[0212] Synthesis Example 26: Preparation of Compound 295

[0213]

[0214] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-295, B-2 with an equimolar amount of B-295, and C-2 with an equimolar amount of C-295, yielding compound 295 (16.51 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 774.3819 (theoretical value: 774.3806). Theoretical elemental content (%) C 54 H 51 FN2Si: C, 83.68; H, 6.63; N, 3.61. Measured elemental content (%): C, 83.65; H, 6.64; N, 3.63.

[0215] Synthesis Example 27: Preparation of Compound 308

[0216]

[0217] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-308, B-2 with an equimolar amount of B-295, and C-2 with an equimolar amount of C-308, yielding compound 308 (17.04 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 822.4356 (theoretical value: 822.4369). Theoretical elemental content (%) C 59 H 58 N₂Si: C, 86.08; H, 7.10; N, 3.40. Measured elemental content (%): C, 86.05; H, 7.11; N, 3.42.

[0218] Synthesis Example 28: Preparation of Compound 311

[0219]

[0220] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-295, and C-2 was replaced with an equimolar amount of C-47, yielding compound 311 (15.59 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 692.3598 (theoretical value: 692.3587). Theoretical elemental content (%) C 49 H 48 N₂Si: C, 84.92; H, 6.98; N, 4.04. Measured elemental content (%): C, 84.96; H, 6.95; N, 4.03.

[0221] Synthesis Example 29: Preparation of Compound 344

[0222]

[0223] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-291, B-2 with an equimolar amount of B-295, and C-2 with an equimolar amount of C-344, yielding compound 344 (18.73 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 878.4039 (theoretical value: 878.4056). Theoretical elemental content (%) C 64 H 54 N₂Si: C, 87.43; H, 6.19; N, 3.19. Measured elemental content (%): C, 87.46; H, 6.18; N, 3.17.

[0224] Synthesis Example 30: Preparation of Compound 346

[0225]

[0226] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-295, and C-2 was replaced with an equimolar amount of C-28, yielding compound 346 (17.07 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 768.3913 (theoretical value: 768.3900). Theoretical elemental content (%) C 55 H 52 N₂Si: C, 85.89; H, 6.82; N, 3.64. Measured elemental content (%): C, 85.84; H, 6.84; N, 3.67.

[0227] Synthesis Example 31: Preparation of Compound 364

[0228]

[0229] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-364, and C-2 was replaced with an equimolar amount of C-28, yielding compound 364 (16.15 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 768.3915 (theoretical value: 768.3900). Theoretical elemental content (%) C 55 H 52 N₂Si: C, 85.89; H, 6.82; N, 3.64. Measured elemental content (%): C, 85.86; H, 6.86; N, 3.63.

[0230] Synthesis Example 32: Preparation of Compound 365

[0231]

[0232] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-365, and C-2 was replaced with an equimolar amount of C-28, yielding compound 365 (16.84 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 768.3911 (theoretical value: 768.3900). Theoretical elemental content (%) C 55 H 52 N₂Si: C, 85.89; H, 6.82; N, 3.64. Measured elemental content (%): C, 85.85; H, 6.84; N, 3.66.

[0233] Synthesis Example 33: Preparation of Compound 370

[0234]

[0235] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-370, B-2 with an equimolar amount of B-370, and C-2 with an equimolar amount of C-28, yielding compound 370 (16.72 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 773.4233 (theoretical value: 773.4214). Theoretical elemental content (%) C 55 H 47 D5N2Si: C, 85.33; H, 7.42; N, 3.62. Measured elemental content (%): C, 85.30; H, 7.40; N, 3.67.

[0236] Synthesis Example 34: Preparation of Compound 401

[0237]

[0238] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-401, and C-2 was replaced with an equimolar amount of C-47, yielding compound 401 (16.84 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 768.3912 (theoretical value: 768.3900). Theoretical elemental content (%) C 55 H 52 N₂Si: C, 85.89; H, 6.82; N, 3.64. Measured elemental content (%): C, 85.83; H, 6.85; N, 3.67.

[0239] Synthesis Example 35: Preparation of Compound 441

[0240]

[0241] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-401, and C-2 was replaced with an equimolar amount of C-28, yielding compound 441 (18.26 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 844.4202 (theoretical value: 844.4213). Theoretical elemental content (%) C 61 H 56 N₂Si: C, 86.68; H, 6.68; N, 3.31. Measured elemental content (%): C, 86.66; H, 6.66; N, 3.35.

[0242] Synthesis Example 36: Preparation of Compound 454

[0243]

[0244] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-291, B-2 with an equimolar amount of B-454, and C-2 with an equimolar amount of C-28, yielding compound 454 (18.00 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 844.4201 (theoretical value: 844.4213). Theoretical elemental content (%) C 61 H 56 N₂Si: C, 86.68; H, 6.68; N, 3.31. Measured elemental content (%): C, 86.66; H, 6.65; N, 3.36.

[0245] Synthesis Example 37: Preparation of Compound 510

[0246]

[0247] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-291, B-2 with an equimolar amount of B-510, and C-2 with an equimolar amount of C-510, yielding compound 510 (18.16 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 876.4788 (theoretical value: 876.4777). Theoretical elemental content (%) C 63 H 56 D4N2Si: C, 86.25; H, 7.35; N, 3.19. Measured elemental content (%): C, 86.28; H, 7.37; N, 3.14.

[0248] Synthesis Example 38: Preparation of Compound 539

[0249]

[0250] Following the method of Example 4, B-2 was replaced with an equimolar amount of B-539, and C-2 was replaced with an equimolar amount of C-28, yielding compound 539 (16.81 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 756.3916 (theoretical value: 756.3900). Theoretical elemental content (%) C 54 H 52 N₂Si: C, 85.67; H, 6.92; N, 3.70. Measured elemental content (%): C, 85.63; H, 6.94; N, 3.72.

[0251] Synthesis Example 39: Preparation of Compound 556

[0252]

[0253] Following the method of Example 4, A-2 was replaced with an equimolar amount of A-291, B-2 with an equimolar amount of B-556, and C-2 with an equimolar amount of C-28, yielding compound 556 (17.63 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 804.3912 (theoretical value: 804.3900). Theoretical elemental content (%) C 58 H 52 N₂Si: C, 86.52; H, 6.51; N, 3.48. Measured elemental content (%): C, 86.54; H, 6.55; N, 3.42.

[0254] [Device Examples]

[0255] The instruments used to test the device performance in this invention consist of a combined IVL testing system comprising testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. This system was used to test the driving voltage and luminous efficiency of the organic electroluminescent device. The lifetime test employed the McScience M6000 OLED lifetime testing system. The testing conditions were atmospheric conditions, room temperature, and a current density of 10 mA / cm². 2 .

[0256] [Device Example 1]

[0257] First, a transparent conductive ITO glass substrate is used as the anode and ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0258] Using vacuum evaporation, a 62 nm thick m-MTDATA layer was deposited on a cleaned ITO glass substrate as a hole injection layer. A 70 nm thick compound 2 layer was then deposited on the hole injection layer as a hole transport layer. An m-CBP:Ir(ppy)2(acac) = 95:5 (mass ratio) layer with a 20 nm thick light-emitting layer was deposited on the hole transport layer. An ET and Liq layer (doped at a 1:1 mass ratio) was then deposited on the light-emitting layer as an electron transport layer with a 32 nm thick layer. LiF was then deposited on the electron transport layer as an electron injection layer with a 1 nm thick layer. Finally, Al was deposited on the electron injection layer as a cathode with a 120 nm thick layer.

[0259]

[0260] [Device Examples 2-36]

[0261] Compounds 15, 19, 28, 36, 47, 74, 84, 89, 110, 119, 129, 144, 149, 168, 181, 183, 200, 217, 241, 291, 293, 295, 308, 311, 344, 346, 364, 365, 370, 401, 441, 454, 510, 539, and 556 of the present invention were used to replace compound 2 in device example 1 as hole transport materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.

[0262] [Comparative Device Examples 1-3]

[0263] Compounds A, B, and C were used respectively to replace compound 2 in device example 1 as hole transport materials. Otherwise, organic electroluminescent devices were prepared using the same preparation method as in device example 1.

[0264] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.

[0265] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-36 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-3 are shown in Table 1 below.

[0266] Table 1:

[0267]

[0268]

[0269] As shown in Table 1, when the compound described in this invention is used as a hole transport material in an organic electroluminescent device, the device exhibits a lower driving voltage, higher luminous efficiency, and longer lifespan. The compound described in this invention is a high-performance hole transport material.

[0270] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A compound comprising a carbazole group, characterized in that, The compound containing a carbazole group is selected from the group consisting of the structure shown in Formula 1, The Ar1-(Ra)m is selected from any one of the following groups, The R5, which are the same or different, are selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C6 alkyl, or a combination thereof; when there are two or more R5, the two or more R5 are the same or different from each other; The e1 is selected from 0, 1, 2, 3, or 4; the e2 is selected from 0, 1, 2, 3, 4, 5, or 6; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the e4 is selected from 0, 1, 2, 3, 4, or 5; the e5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; The m1 is selected from 1 or 2; the m2 is selected from 1 or 2; the m3 is selected from 1 or 2; the m4 is selected from 1 or 2; the m5 is selected from 1 or 2; the m7 is selected from 1; The Ra is selected from Si(R0)3; The R0, which are the same or different, are selected from any one of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C12 aryl, or a combination thereof; The Ar is selected from any one of substituted or unsubstituted C6-C12 aryl; The Ar2-(Rb)n is selected from any one of the following groups, The L0 is selected from a single bond or any one of the following groups, The L1, L2, which are the same or different, are selected from a single bond or any one of the following groups, The R8, which are the same or different, are selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C6 alkyl, or a combination thereof; when there are two or more R8, the two or more R8 are the same or different from each other; The q1, which are the same or different, are selected from 0, 1, 2, 3, or 4; the q2, which are the same or different, are selected from 0, 1, 2, 3, 4, 5, or 6; the q6, which are the same or different, are selected from 0, 1, 2, 3, 4, or 5; The R1, R2, which are the same or different, are selected from any one of hydrogen, deuterium, tritium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, or a combination thereof, or two adjacent R1 are connected to each other to form a substituted or unsubstituted benzene ring, or two adjacent R2 are connected to each other to form a substituted or unsubstituted benzene ring; the a is selected from 0, 1, 2, 3, or 4; the b is selected from 0, 1, 2, or 3; The substituents in the "substituted or unsubstituted" are independently selected from deuterium, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl.

2. The compound containing a carbazole group according to claim 1, characterized by The Ra is selected from any one of the following groups, The R3, which are the same or different, are selected from any one of hydrogen, deuterium, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, or a combination thereof; The c1, which are the same or different, are selected from 0, 1, 2, 3, 4, or 5; the c2, which are the same or different, are selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c3, which are the same or different, are selected from 0, 1, 2, 3, 4, 5, 6, or 7.

3. The compound containing a carbazole group according to claim 1, characterized by The Ar1-(Ra)m is selected from any one of the following groups, R5is the same or different selected from any one of hydrogen, deuterium, tritium, or a combination thereof.

4. The compound containing a carbazole group according to claim 1, characterized by Ar2-(Rb)n is selected from any one of the following groups, 。 5. The compound containing a carbazole group according to claim 1, characterized by Ar is selected from any one of the following groups, R7is the same or different selected from any one of hydrogen, deuterium, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, or a combination thereof; when there are two or more R7, the two or more R7are the same or different from each other; k1is the same or different selected from 0, 1, 2, 3, 4, or 5; k2is the same or different selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; k4is the same or different selected from 0, 1, 2, 3, 4, 5, 6, or 7.

6. The compound containing a carbazole group according to claim 1, characterized by L0is selected from a single bond or any one of the following groups, R8is the same or different selected from any one of hydrogen, deuterium, tritium, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, or a combination thereof.

7. A compound comprising a carbazole group, characterized in that, The compound is selected from any one of the following structures, 。 8. An organic electroluminescent device, characterized by The organic electroluminescent device comprises the compound containing a carbazole group according to any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, which comprises an anode, a cathode, and an organic layer between the anode and the cathode, the organic layer comprising a hole-transporting region, a light-emitting layer, and an electron-transporting region, characterized in that, The hole transport region comprises the compound containing a carbazole group according to any one of claims 1-7.

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