A triarylamine compound and its organic electroluminescent device

Abstract

This invention provides a triarylamine compound and its organic electroluminescent device, relating to the field of organic electroluminescent materials technology. The triarylamine compound of Formula 1 exhibits good hole mobility, enabling effective hole transport and allowing holes to effectively combine with electrons within the emissive layer to emit light, thus improving the device's luminous efficiency. Furthermore, the well-matched energy levels of the triarylamine compound of Formula 1 result in a lower hole injection barrier, reducing the device's driving voltage. Additionally, the good stability of the triarylamine compound extends the device's lifespan, resulting in superior device performance.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), as a strong contender for next-generation lighting and flat panel displays, have maintained a robust and rapid development since their inception, sparking a research boom worldwide and attracting attention from numerous countries and regions. OLEDs possess characteristics such as self-illumination, high contrast, thinness, wide viewing angle, fast response speed, low energy consumption, and the ability to fabricate flexible devices, earning them the reputation of a dream display technology.

[0003] OLEDs are electroluminescent. By applying an external voltage, charge carriers, namely electrons and holes, are obtained at the cathode and anode, respectively. Subsequently, the charge carriers are injected into the organic layer, and the electrons and holes migrate to the light-emitting layer through the charge carrier transport region. They combine in the light-emitting layer to form excitons. When these excitons radiatively relax from the excited state to the ground state, electroluminescence occurs.

[0004] OLED device structures have evolved from single-layer to dual-layer structures, then to more complex three-layer structures, and finally to the classic multilayer structures. Single-layer and dual-layer devices suffer from low efficiency due to the lack of corresponding hole and electron transport layers, while multilayer devices offer superior performance compared to three-layer devices. Therefore, multilayer structures are currently the most commonly used.

[0005] Multilayer device structures typically include an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. Some more complex device structures introduce organic functional layers such as hole injection layers, electron injection layers, hole blocking layers, or electron blocking layers to increase the recombination probability of charge carriers and improve the overall efficiency of the device.

[0006] The hole transport layer plays a crucial role in OLEDs by improving the balance between hole injection and transport, thereby enhancing device performance. Therefore, developing stable and efficient hole transport materials is a significant current task. Summary of the Invention

[0007] To address the problems existing in the prior art, the present invention provides a triarylamine compound and its organic electroluminescent device.

[0008] This invention provides a triarylamine compound, represented by the following formula 1.

[0009]

[0010] Wherein, Ar1 is selected from the group represented by formula 1-a1 or formula 1-a2.

[0011] The R1 is selected from the group shown in Formula 1-b, the R 10 Selected from the groups shown in Formula 1-c,

[0012]

[0013] X is selected from O, S, N(R) x ), the R x It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0014] The m is selected from an integer from 0 to 2, and the same or different R4 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3 to C20 alicyclic and C6 to C30 aromatic rings;

[0015] The ring A is selected from substituted or unsubstituted C6-C30 aromatic rings or substituted or unsubstituted C2-C30 heteroaromatic rings;

[0016] The R2 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or a group shown in Formula 1-b, or a combination thereof.

[0017] The n is selected from an integer from 0 to 4, the n1 is selected from an integer from 0 to 3, and the R3s, whether the same or different, are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R3s bonded to each other to form a substituted or unsubstituted ring;

[0018] The Ar2 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination thereof as shown below.

[0019]

[0020] e1 is selected from integers from 0 to 5, and e2 is selected from integers from 0 to 4.

[0021] The R6s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R6s bonded together to form substituted or unsubstituted rings.

[0022] The same or different R0s are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R0s bonded together to form substituted or unsubstituted rings;

[0023] The Y is selected from O, S, N(R) y ) or C(R y )2, the R y The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or two adjacent R yThey bond together to form substituted or unsubstituted rings;

[0024] The E that is the same or different is selected from CH or N, and at least one E is N;

[0025] The Ar3 is selected from one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic groups and C6-C30 aromatic groups.

[0026] The L2, L3, and L4 are independently selected from one or a combination thereof, of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C20 alicyclic and a C6-C30 aromatic ring.

[0027] The L1 is selected from one or a combination of single bonds, substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C2-C30 heteroarylene groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and the substituents on the arylene groups in the L1 are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, and substituted or unsubstituted C2-C25 heteroarylene group.

[0028] In addition, the present invention also provides an organic electroluminescent device containing the triarylamine compound described above.

[0029] Beneficial effects: The triarylamine compound of Formula 1 of this invention has a good hole mobility, which can effectively transport holes, enabling holes to effectively combine with electrons in the light-emitting layer to emit light, thereby improving the luminous efficiency of the device. Secondly, the well-matched energy level of the triarylamine compound of Formula 1 gives the holes a lower injection barrier, reducing the driving voltage of the device. In addition, the good stability of the triarylamine compound extends the lifespan of the device, enabling the device to exhibit excellent performance. Detailed Implementation

[0030] 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.

[0031] In this specification, halogens include fluorine, chlorine, bromine, and iodine.

[0032] In the compounds described herein, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances. In this invention, "H," "hydrogen," and "hydrogen atom" refer to isotopes with different numbers of neutrons, including protium, deuterium, and tritium.

[0033] In this specification, "integer selected from 0 to M" means that the value is selected from any one of the integers from 0 to M, including 0, 1, 2...M-2, M-1, M. For example, "n1 is selected from 0 to 3" means that n1 is selected from 0, 1, 2, or 3. And so on.

[0034] 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. For example, Can represent Can represent Can represent And so on.

[0035] 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 rings. For example, Can represent or Can represent And so on.

[0036] In this specification, "the formation of a ring by bonding two adjacent groups" refers to the formation of a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by bonding adjacent groups together and optionally aromatizing them. The hydrocarbon ring can be an aliphatic or aromatic hydrocarbon ring. The heterocycle can be an aliphatic or aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated or unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated or unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by bonding adjacent groups can be connected to another ring to form a spirostructure. See the example below:

[0037]

[0038] In this specification, the rings formed by the linkage can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0039] In this specification, "unsubstituted ZZ group" in "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not substituted by a substituent. For example, "unsubstituted aryl group" in "substituted or unsubstituted C6-C60 aryl group" means that the hydrogen atom of the "aryl group" is not substituted by a substituent. And so on.

[0040] In this specification, "CXX~CYY" in "substituted or unsubstituted CXX~CYY ZZ group" represents the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has a substituent, the number of carbon atoms in the substituent is not included. For example, "C6~C60" in "substituted or unsubstituted C6~C60 aryl group" represents the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, the number of carbon atoms in the substituent is not included. And so on.

[0041] In this specification, "substituted" in "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" in the above-mentioned terms include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted C3-C15 heterocyclic group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, substituted or unsubstituted C6-C20 aryl group, substituted or unsubstituted C2-C20 heteroaryl group, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C20 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C20 heteroaryl ring, etc. Preferred groups include: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, fentanyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The substituents include benzo[a]yl, fluorenyl, dihydroindene, indene, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocycloheptane, benzocyclobutenyl, fluorenyl, benzo[fluorenyl]spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, benzodibenzofuranyl, carbazoleyl, benzocarbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can bond to form a substituted or unsubstituted ring.

[0042] In this invention, the alkyl group refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule, and the alkyl group includes straight-chain alkyl and branched-chain alkyl. Chain alkyl groups containing three or more carbon atoms include their isomers, such as butyl including n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on. Examples of the alkyl group may include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, etc., but are not limited thereto. The alkyl group has 1 to 20 carbon atoms, preferably 1 to 15, and even more preferably 1 to 10.

[0043] In this invention, the cycloalkyl group refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl, polycyclic cycloalkyl, and bridged cycloalkyl groups. Examples of the cycloalkyl group may include adamantyl, norbornel, camphenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc., but are not limited thereto. The cycloalkyl group has 3 to 20 carbon atoms, preferably 3 to 15, and more preferably 3 to 10.

[0044] In this invention, the aryl group refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. The aryl group includes monocyclic aryl, polycyclic aryl, fused-ring aryl, or combinations thereof. Examples of the aryl group may include phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene, perylene, etc. Aryl, fluoranyl, fluorenyl, benzo[a]fluorenyl, spirodifluorenyl, benzo[a]spirodifluorenyl, spiroanthracene fluorenyl, etc., but not limited to these. The number of carbon atoms in the aryl group is 6 to 30, preferably 6 to 25, more preferably 6 to 18, and even more preferably 6 to 12.

[0045] In this invention, the term "heteroaryl" refers to a group obtained by replacing at least one carbon atom in an aryl group with a heteroatom. The heteroatom includes, but is not limited to, atoms such as oxygen, sulfur, nitrogen, phosphorus, boron, and silicon. The heteroaryl comprises monocyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group may include, but are not limited to, indolyl, carbazole, benzocarbazole, dibenzocarbazole, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, naphthofuranyl, phenanthrofuranyl, pyridinofuranyl, pyrazinofuranyl, pyridazinofuranyl, quinolinofuranyl, isoquinolinofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, naphthothiophene, phenanthiophene, pyridinothiophene, pyrazinothiophene, pyridazinothiophene, quinolinothiophene, isoquinolinothiophene, spirofluorenexanthyl, spirofluorenethionanthyl, spirofluorenexanthyl, pyridinyl, etc. The heteroaryl group may have 2 to 30 carbon atoms, preferably 2 to 25, and even more preferably 3 to 18.

[0046] In this invention, the fused alicyclic and aromatic ring group refers to the general term for a monovalent group remaining after removing one hydrogen atom from the fused alicyclic and aromatic rings. Examples of the fused alicyclic and aromatic ring group may include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The alicyclic ring has 3 to 20 carbon atoms, preferably 3 to 15, and even more preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 25, preferably 6 to 18, even more preferably 6 to 12, and even more preferably 6 to 10.

[0047] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R s )3 groups, wherein each R s The same or different groups are selected from the following: 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 sThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl. 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. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... s The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silanes specifically include, but are not limited to, trimethylsilane, triethylsilane, tripropylsilane, triisopropylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, and phenylsilane. The aforementioned substituted silanes are preferably trimethylsilane, triethylsilane, triphenylsilane, diphenylmethylsilane, phenyldimethylsilane, diphenylmethylsilane, and phenyldimethylsilane.

[0048] In this invention, the term "arylene" refers to the collective term for divalent groups remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. The arylene includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of the arylene may include, but are not limited to, phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, trimethyleneene, fluorene, benzo[a]fluorene, and spirodifluorene. The number of carbon atoms in the arylene is 6 to 30, preferably 6 to 18.

[0049] In this invention, the heteroaryl group refers to a divalent group in which at least one carbon atom is replaced by a heteroatom. The heteroatom is selected from oxygen, sulfur, nitrogen, phosphorus, boron, silicon, etc., but is not limited thereto. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group may include, but are not limited to, furanyl, benzofuranyl, dibenzofuranyl, thiopheneyl, benzothiopheneyl, dibenzothiopheneyl, carbazoyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, etc. The number of carbon atoms in the heteroaryl group is 2 to 30, preferably 2 to 25, and even more preferably 3 to 18.

[0050] In this invention, the term "hybridized alicyclic and aromatic rings" refers to the general term for divalent groups remaining after two hydrogen atoms are removed from the alicyclic and aromatic rings that have been fused together. Examples of the hybridized 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 20 carbon atoms, preferably 3 to 15, and more preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 18, more preferably 6 to 12, and more preferably 6 to 10.

[0051] This invention provides a triarylamine compound, represented by the following formula 1.

[0052]

[0053] Wherein, Ar1 is selected from the group represented by formula 1-a1 or formula 1-a2.

[0054] The R1 is selected from the group shown in Formula 1-b, the R 10 Selected from the groups shown in Formula 1-c,

[0055]

[0056] X is selected from O, S, N(R) x ), the R x It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0057] The m is selected from an integer from 0 to 2, and the same or different R4 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3 to C20 alicyclic and C6 to C30 aromatic rings;

[0058] The ring A is selected from substituted or unsubstituted C6-C30 aromatic rings or substituted or unsubstituted C2-C30 heteroaromatic rings;

[0059] The R2 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic ring, or a group shown in Formula 1-b, or a combination thereof.

[0060] The n is selected from an integer from 0 to 4, the n1 is selected from an integer from 0 to 3, and the R3s, whether the same or different, are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R3s bonded to each other to form a substituted or unsubstituted ring;

[0061] The Ar2 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination thereof as shown below.

[0062]

[0063] e1 is selected from integers from 0 to 5, and e2 is selected from integers from 0 to 4.

[0064] The R6s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R6s bonded together to form substituted or unsubstituted rings.

[0065] The same or different R0s are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R0s bonded together to form substituted or unsubstituted rings;

[0066] The Y is selected from O, S, N(R) y ) or C(R y )2, the R y The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or two adjacent R y They bond together to form substituted or unsubstituted rings;

[0067] The E that is the same or different is selected from CH or N, and at least one E is N;

[0068] The Ar3 is selected from one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C20 alicyclic groups and C6-C30 aromatic groups.

[0069] The L2, L3, and L4 are independently selected from one or a combination thereof, of a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C20 alicyclic and a C6-C30 aromatic ring.

[0070] The L1 is selected from one or a combination of single bonds, substituted or unsubstituted C6-C30 arylene groups, substituted or unsubstituted C2-C30 heteroarylene groups, substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, and the substituents on the arylene groups in the L1 are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C3-C15 cycloalkyl group, and substituted or unsubstituted C2-C25 heteroarylene group.

[0071] Preferably, the Ar2 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination of the groups shown below.

[0072]

[0073]

[0074] The integer e1 is selected from 0 to 5, the integer e2 is selected from 0 to 4, the integer e3 is selected from 0 to 7, the integer e4 is selected from 0 to 9, the integer e5 is selected from 0 to 3, the integer e6 is selected from 0 to 2, the integer e7 is selected from 0 to 6, the integer e8 is selected from 0 to 8, and the integer e9 is selected from 0 to 10.

[0075] The R6, R 60 The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R6, two adjacent R 60 They bond together to form substituted or unsubstituted rings;

[0076] The R y The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R y They bond together to form substituted or unsubstituted rings;

[0077] The R e The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R e They bond with each other to form substituted or unsubstituted rings.

[0078] Preferably, R6, R 60The same or different from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydro Naphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiophene One or a combination thereof, or two adjacent R6 groups, or two adjacent R6 groups. 60 They bond together to form substituted or unsubstituted rings;

[0079] The R ySelected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydro Naphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted The following are possible combinations of substituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted indole group, substituted or unsubstituted carbazole group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, or two adjacent R groups. y They bond together to form substituted or unsubstituted rings;

[0080] The R e Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, etc. One or a combination thereof, or two adjacent Rs, of the following: substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl. eThey bond with each other to form substituted or unsubstituted rings.

[0081] Preferably, the Ar3 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination of the groups shown below.

[0082]

[0083] f1 is selected from integers from 0 to 5, and f2 is selected from integers from 0 to 4.

[0084] The R7s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R7s bonded together to form substituted or unsubstituted rings.

[0085] The R ` The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0086] The W is selected from O, S, N(R) w ), C(R w )2 or Si(R w )2, the R w The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or two adjacent R w They bond together to form substituted or unsubstituted rings;

[0087] W1 is selected from O, S, or N(R). w1 ), the R w1It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings;

[0088] The Fs that are the same or different are selected from CH or N, and at least one F is N.

[0089] Preferably, the Ar3 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination of the groups shown below.

[0090]

[0091] f1 is selected from integers from 0 to 5, f2 is selected from integers from 0 to 4, f3 is selected from integers from 0 to 7, f4 is selected from integers from 0 to 9, f5 is selected from integers from 0 to 3, f6 is selected from integers from 0 to 2, f7 is selected from integers from 0 to 6, f8 is selected from integers from 0 to 8, and f9 is selected from integers from 0 to 10.

[0092] The R7, R 70 The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R7s, two adjacent Rs 70 They bond together to form substituted or unsubstituted rings;

[0093] The R ` The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings;

[0094] The R wThe same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R w They bond together to form substituted or unsubstituted rings;

[0095] The R w1 It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings;

[0096] The R f The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R f They bond with each other to form substituted or unsubstituted rings.

[0097] Preferably, the Ar3 is selected from the groups shown in Formula 1-a1, Formula 1-a2, or one or a combination of the groups shown below.

[0098]

[0099]

[0100] f1 is selected from integers from 0 to 5, f2 is selected from integers from 0 to 4, f3 is selected from integers from 0 to 7, f4 is selected from integers from 0 to 9, f5 is selected from integers from 0 to 3, f6 is selected from integers from 0 to 2, f7 is selected from integers from 0 to 6, f8 is selected from integers from 0 to 8, and f9 is selected from integers from 0 to 10.

[0101] The R7, R 70The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, or two adjacent R7s, two adjacent Rs 70 They bond together to form substituted or unsubstituted rings;

[0102] The R ` The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings;

[0103] The R w The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings;

[0104] The R w1 It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings;

[0105] The R f The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C10 alicyclic and C6-C20 aromatic rings, or two adjacent R f They bond with each other to form substituted or unsubstituted rings.

[0106] Preferably, R7, R 70The same or different from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetrahydro Naphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiophene One or a combination thereof, or two adjacent R7s, two adjacent R7s, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted indolyl group, substituted or unsubstituted carbazole group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, or two adjacent R7s ... 70 They bond together to form substituted or unsubstituted rings;

[0107] The R `Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted Tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, One or a combination thereof of substituted or unsubstituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted indol group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, and substituted or unsubstituted isoquinolinyl group;

[0108] The R wSelected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted Tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, One or a combination thereof of substituted or unsubstituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted indol group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, and substituted or unsubstituted isoquinolinyl group;

[0109] The R w1Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted anthracene, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted Tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzospirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, One or a combination thereof of substituted or unsubstituted thiophene group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted indol group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, and substituted or unsubstituted isoquinolinyl group;

[0110] The R f Selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, etc. One or a combination thereof, or two adjacent Rs, of the following: substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl. f They bond with each other to form substituted or unsubstituted rings.

[0111] Preferably, the and Ring A in the figure is selected from one of the following groups:

[0112]

[0113]

[0114] The m is selected from integers from 0 to 2, the m1 is selected from integers from 0 to 4, the m2 is selected from integers from 0 to 6, the m3 is selected from integers from 0 to 8, the m4 is selected from integers from 0 to 3, the m5 is selected from integers from 0 to 5, and the m6 is selected from integers from 0 to 7.

[0115] X is selected from O, S, N(R) x ), the R x It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings;

[0116] The R4 is the same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings;

[0117] The R5 is the same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C20 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings.

[0118] Preferably, the R xSelected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, substituted or unsubstituted tetramethylsilyl ... One or a combination of the following: hydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, and substituted or unsubstituted isoquinolinyl.

[0119] R4 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or unsubstituted The tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or a combination thereof;

[0120] R5 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted The tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or a combination thereof.

[0121] Preferably, the middle,

[0122] The R1 is selected from the group shown in Formula 1-b, the R 10 Selected from the groups shown in Formula 1-c,

[0123] The R2 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic ring, or a group shown in Formula 1-b, or a combination thereof.

[0124] The R3s, whether identical or different, are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or adjacent R3s bonded together to form a substituted or unsubstituted ring.

[0125] Preferably, the Ar1 is selected from one of the groups shown in Formula 1-a1 or Formula 1-a2.

[0126]

[0127] Formula 1-a1 is selected from one of the groups shown in Formulas 1-a3 to 1-6 below.

[0128]

[0129] Preferably, R1 is selected from the group shown in Formula 1-b, wherein R 10 Selected from the groups shown in Formula 1-c.

[0130] Preferably, R2 is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene. The group may contain, or be composed of, a combination of, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirodifluorenyl group, a substituted or unsubstituted dihydroindene group, a substituted or unsubstituted indene group, a substituted or unsubstituted tetrahydronaphthyl group, a substituted or unsubstituted dihydronaphthyl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted benzocyclobutenyl group, a substituted or unsubstituted benzocycloheptyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted carbazoyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, or any group represented by formula 1-b.

[0131] Preferably, R3 is the same as or different from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted Cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dihydroindenyl, substituted or Unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted One or a combination of substituted dibenzothiophene, substituted or unsubstituted indol, substituted or unsubstituted carbazolyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or two adjacent R3s bonded to each other to form a substituted or unsubstituted ring.

[0132] Preferably, L2, L3, and L4 are independently selected from single bonds or one or a combination of the following groups:

[0133]

[0134] k1 is selected from integers from 0 to 4, k2 is selected from integers from 0 to 3, and k3 is selected from integers from 0 to 2.

[0135] The R8s, whether identical or different, are selected from one or a combination thereof, including hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C20 alicyclic and C6-C30 aromatic rings, or adjacent R8s bonded together to form substituted or unsubstituted rings.

[0136] The Z that is the same or different is selected from CH or N, and at least one Z is N;

[0137] The L1 is selected from a single bond or one or a combination of the following groups.

[0138]

[0139] The g1 is selected from integers from 0 to 4, the g2 is selected from integers from 0 to 3, and the g3 is selected from integers from 0 to 2.

[0140] The R9s are the same or different and are selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R9s are bonded to each other to form a substituted or unsubstituted ring.

[0141] The V that is the same or different is selected from CH or N, and at least one V is N.

[0142] Preferably, L2, L3, and L4 are independently selected from single bonds or one or a combination of the following groups:

[0143]

[0144] k1 is selected from integers from 0 to 4, k2 is selected from integers from 0 to 3, k3 is selected from integers from 0 to 2, k4 is selected from integers from 0 to 6, and k5 is selected from integers from 0 to 8;

[0145] The R8 is the same as or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalkanes of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings;

[0146] The R k The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C25 aromatic rings, or two adjacent R k They bond together to form substituted or unsubstituted rings;

[0147] The L1 is selected from a single bond or one or a combination of the following groups.

[0148]

[0149] The g1 is selected from integers from 0 to 4, the g2 is selected from integers from 0 to 3, the g3 is selected from integers from 0 to 2, the g4 is selected from integers from 0 to 6, and the g5 is selected from integers from 0 to 8;

[0150] The same or different R9 is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C25 heteroaryl.

[0151] The R g The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C2-C25 heteroaryl, or two adjacent Rs g They bond with each other to form substituted or unsubstituted rings.

[0152] Preferably, the same or different R8s are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindene, substituted or unsubstituted indene, etc. The substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, or a combination thereof;

[0153] The R k The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclobutyl, or two adjacent R k They bond together to form substituted or unsubstituted rings;

[0154] The R9 is the same as or different from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindenyl, substituted or unsubstituted indenyl, substituted or One or a combination of unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted indolyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolinyl, and substituted or unsubstituted isoquinolinyl.

[0155] The R g The same or different from one or a combination thereof selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dihydroindyl, substituted or unsubstituted indyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocyclobutyl, or two adjacent R g They bond with each other to form substituted or unsubstituted rings.

[0156] Preferably, the triarylamine compound of Formula 1 is selected from at least one of the following structures:

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] The above lists some specific chemical structures of the triarylamine compounds represented by Formula 1 of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents defined above should be included.

[0181] In addition, the present invention also provides an organic electroluminescent device containing the triarylamine compound described above.

[0182] Preferably, the organic electroluminescent device includes an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode, and the organic layer contains the triarylamine compound described in this invention.

[0183] Preferably, the organic layer includes a hole transport region containing the triarylamine compound described in this invention.

[0184] Preferably, the hole transport region contains a hole transport layer, and the hole transport layer contains the triarylamine compound described in this invention.

[0185] The functional layer of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, light-emitting layer, hole blocking layer, electron transport layer, electron injection layer, capping layer, etc. Any functional layer having hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, or light extraction properties should be included. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may be composed of only one material or multiple materials.

[0186] 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:

[0187] Anode: The anode of this invention needs to have a high work function, good stability, and high conductivity. 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 silver (Ag), gold (Au), platinum (Pt), nickel (Ni), palladium (Pd), indium tin oxide (ITO), indium zinc oxide (IZO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), poly(3-methylthiophene), etc., but are not limited to these.

[0188] Cathode: The cathode of this invention needs to have a low work function and good stability. The cathode includes, but is not limited to, the materials described below, metals or their alloys, laminated materials, etc. Specific examples may include silver (Ag), aluminum (Al), magnesium (Mg), calcium (Ca), magnesium:silver (Mg:Ag), aluminum oxide:aluminum (Al2O3:Al), lithium:aluminum (Li:Al), etc., but are not limited to these.

[0189] Hole injection layer: The hole injection layer of this invention serves to further increase the work function of the anode in the device, thereby improving hole injection. The hole injection layer includes, but is not limited to, the materials described below: aromatic amine derivatives, polycyano conjugated organic compounds, phthalocyanine metal complexes, metal oxides, polymers, etc. Specific examples may include, but are not limited to, 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (2-TNATA), N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamino)phenyl]benzidine (NPNPB), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (PCzPCA2), 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), 7,7,8,8-tetracyano-p-benzoquinone dimethyl ether (TCNQ), zinc phthalocyanine (ZnPC), molybdenum oxide (MoO3), poly(3,4-vinyldioxythiophene):poly(styrene sulfonate) (PEDT:PSS), etc.

[0190] Hole transport layer: The hole transport layer of this invention functions to lower the energy level barrier between the anode and the light-emitting layer, and then transports the holes injected by the anode to the light-emitting layer. The hole transport layer includes, but is not limited to, the materials described below, such as aromatic amine derivatives, carbazole derivatives, polymers, etc. Specific examples may include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), tri(biphenyl-4-yl)amine (TBA), 4,4'-(9H-fluorene-9-ylidene)bis[N,N-bis(4-methylphenyl)aniline (DTAF), 4,4'-(diphenylsilanediyl)bis(N,N-diphenylaniline) (TSBPA), 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), polyvinylcarbazole (PVK), etc., but is not limited thereto. Preferably, the triaromatic amine compound of Formula 1 of this invention is preferred.

[0191] Light-emitting layer: The light-emitting layer of the present invention comprises a host material and a dopant material. The light-emitting material may be a red light-emitting material, a green light-emitting material, a blue light-emitting material, or a combination thereof. The doping ratio of the host material and the dopant material may vary depending on the material used. Typically, the doping ratio of the dopant material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0192] The host material of the luminescent layer not only needs to possess bipolar charge transport properties but also requires appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. The host material can be one material or two or more materials. Host materials include, but are not limited to, the following: heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples include 9-(3-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, 9-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, 2,7-bis(diphenylphosphate)-9,9'-spirodifluorene (SPPO13), 2,7-bis(carbazole-9-yl)-9,9-spirodifluorene (Spiro-2CBP), 3,5 3,3'-bis(3-(9H-carbazole-9-yl)phenyl)pyridine (35DCzPPy), 3,3'-bis(dibenzothiophene-4-yl)-1,1'-biphenyl (m-BPDBT), 3'-(dibenzothiophene-4-yl)-10-phenyl-10H-spiro[acridin-9,9'-fluorene] (STDBT-4), 1,4-bis(9-phenyl-9H-fluorene-9-yl)phenyl (pDPFB), tris(8-hydroxyquinoline)aluminum (Alq3), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9Hcarbazole (CzSi), etc., but not limited to these.

[0193] The doped material can be a fluorescent material, a phosphorescent material, a TADF material, or a combination thereof. Doped materials include, but are not limited to, the following: metal complexes, aromatic amine derivatives, styrene amine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include tris[2-(2,4-difluorophenyl)pyridine]iridium (Ir(Fppy)3), bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (FIrPic), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetonate)iridium (Ir(bzq)2(acac)), tris[2-(4-n-hexylphenyl)quinoline]iridium (Hex-Ir(phq)3), bis(1-phenyl-isoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), tris(1-phenyl-isoquinoline)iridium (Ir(piq)2(acac)). Ir(piq)3), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), 2,5,8,11-tetra-tert-butylperylene (TBPe), 9,10-bis[N,N-di(p-tolyl)amino]anthracene (TTPA), 9,10-bis[N-(m-tolyl)phenylamino]anthracene (TPA), 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidin-9-enyl)-4H-pyran (DCJTB), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), etc., but not limited to these.

[0194] Electron transport layer: The function of the electron transport layer in this invention is to lower the energy level barrier between the cathode and the light-emitting layer, and then transport the electrons injected from the cathode to the light-emitting layer. The electron transport layer includes, but is not limited to, the materials described below, such as metal complexes and heteroaromatic compounds. Specific examples may include, but are not limited to, aluminum 8-hydroxyquinoline (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzimidazole (DNDAPM), 1,3,5-tris[(3-pyridyl)-phenyl-3-yl]benzene (TmPyPB), 1,3,5-tris(1-phenyl-1-benzimidazole-2-yl)benzene (TPBi), 3,5-diphenyl-4-(1-naphthyl)-1,2,4-triazole (NTAZ), 2,7-bis[2-(2,2'-bipyridin-6-yl)-1,3,4-oxadiazol-5-yl]-9,9-dimethylfluorene (Bpy-FOXD), etc.

[0195] Electron injection layer: The function of the electron injection layer in this invention is to modify the interface of the cathode material, reduce the energy level barrier between the cathode material and the organic material, and increase the electron injection efficiency. The electron injection material includes, but is not limited to, the materials described below, such as metals, metal compounds, and metal oxides. Specific examples may include, but are not limited to, lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), calcium fluoride (CaF2), cesium carbonate (CsCO3), and lithium oxide (Li2O).

[0196] 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 methods.

[0197] The organic electroluminescent device of this invention is mainly used in the fields of information display technology and lighting. In terms of information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-screen TVs, smartwatches, VR, in-vehicle systems, digital cameras, wearable devices, etc.

[0198] Synthesis Examples

[0199] 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.

[0200] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0201] There are no particular limitations on the preparation method of the triarylamine compound of Formula 1 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. The triarylamine compound of Formula 1 of the present invention can be prepared, for example, by the synthetic route shown below.

[0202]

[0203] The Xn is a halogen, for example, the same or different Xn are selected from Cl, Br, I.

[0204] Synthesis example 1:

[0205]

[0206] Preparation of A-15: Under nitrogen protection, a-15 (15.17 g, 77 mmol) was dissolved in 70 ml of anhydrous tetrahydrofuran. The temperature of the solution was maintained at -78 °C. 30.8 ml of 2.5 M n-butyllithium in hexane was slowly added dropwise to the solution, and then the mixture was stirred for 2 hours to obtain a tetrahydrofuran solution of A-15.

[0207] Preparation of B-15: Under nitrogen protection, b-15 (15.76 g, 80 mmol) was dissolved in 180 mL of anhydrous tetrahydrofuran. The solution temperature was maintained at -78 °C. 32 mL of 2.5 M n-butyllithium in hexane was slowly added dropwise. After the addition was complete, the mixture was stirred for 30 minutes. c-15 (8.60 g, 80 mmol) was dissolved in 120 mL of tetrahydrofuran and added dropwise. The reaction mixture was stirred at -78 °C for 1 hour. The reaction was terminated by adding dilute hydrochloric acid. The mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate. The mixture was filtered, the solvent was removed under reduced pressure, and the solution was purified by silica gel column chromatography (petroleum ether:dichloromethane = 6:1) to obtain B-15 (13.62 g, yield 90%); HPLC purity ≥99.94%.

[0208] Preparation of C-15: Under nitrogen protection, a previously prepared tetrahydrofuran solution of A-15 was added to the reaction flask. The solution temperature was maintained at -78℃. 28 ml of a 2.5 M n-butyllithium solution in hexane was slowly added dropwise. After the addition was complete, the mixture was stirred for 30 minutes. B-15 (13.24 g, 70 mmol) was dissolved in 100 ml of tetrahydrofuran and added dropwise. The reaction solution was heated from -78℃ to 0℃ and stirred. The reaction was terminated by adding dilute hydrochloric acid. The mixture was extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (n-hexane:ethyl acetate = 7:1) to obtain C-15 (11.93 g, yield 65%); HPLC purity ≥99.86%.

[0209] Preparation of D-15: D-15 (14.36 g, 40 mmol) was dissolved in 75 mL of anhydrous tetrahydrofuran. Under nitrogen atmosphere, the solution temperature was maintained at -78 °C. 16 mL of a 2.5 M n-butyllithium solution in hexane was slowly added dropwise. After the addition was complete, the mixture was stirred for 1 hour. Then, C-15 (10.49 g, 40 mmol) was dissolved in 50 mL of tetrahydrofuran and added dropwise. The reaction solution was maintained at -78 °C and stirred for 1 hour, then allowed to reach room temperature and stirred overnight. The solvent was removed under reduced pressure, and the residue was dissolved in glacial acetic acid (60 mL). A concentrated hydrochloric acid solution (31%, 6 mL) was added, and the mixture was reacted under reflux for 3.5 hours and stirred overnight at room temperature. After the reaction was complete, water was added, and the mixture was extracted with dichloromethane. The organic phases were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was recrystallized from isopropanol to give D-15 (13.36 g, yield 70%); HPLC purity ≥99.91%.

[0210] Preparation of E-15: Under nitrogen protection, D-15 (11.93 g, 25 mmol), e-15 (4.32 g, 25.5 mmol), palladium acetate (45 mg, 0.2 mmol), tri-tert-butylphosphine (81 mg, 0.4 mmol), sodium tert-butoxide (2.88 g, 30 mmol), and toluene (200 ml) were added to a reaction flask. The mixture was stirred under reflux for 10 hours, cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from ethyl acetate / petroleum ether (3:1) to obtain E-15 (10.46 g, yield 74%); HPLC purity ≥99.88%.

[0211] Preparation of Compound 15: Under nitrogen protection, E-15 (8.48 g, 15 mmol), f-15 (3.50 g, 15 mmol), sodium tert-butoxide (1.73 g, 18 mmol), tris(dibenzylacetone) dipalladium (137 mg, 0.15 mmol), tri-tert-butylphosphine (61.00 mg, 0.30 mmol), and toluene (100 ml) were added to a reaction flask and reacted under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was recrystallized from toluene / ethanol (4:1) to give compound 15 (8.72 g, yield 81%); HPLC purity ≥99.93%. Mass spectrometry m / z: 717.2675 (theoretical value: 717.2668). Theoretical elemental content (%) C 53 H 35 NO2: C, 88.68; H, 4.91; N, 1.95. Measured elemental content (%): C, 88.65; H, 4.88; N, 1.97.

[0212] Synthesis example 2:

[0213]

[0214] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and e-15 were replaced with equimolar amounts of a-54, b-54, and e-54, respectively, to obtain compound 54 (9.46 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 829.3362 (theoretical value: 829.3345). Theoretical elemental content (%) C 63 H 43 NO: C, 91.16; H, 5.22; N, 1.69. Measured elemental content (%): C, 91.19; H, 5.26; N, 1.66.

[0215] Synthesis example 3:

[0216]

[0217]

[0218] Following the preparation method of compound 15 in Synthetic Example 1, a-15 and b-15 were replaced with equimolar amounts of a-77 and a-77, respectively, to obtain compound 77 (8.89 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 749.2226 (theoretical value: 749.2211). Theoretical elemental content (%) C 53 H 35 NS2: C, 84.88; H, 4.70; N, 1.87. Measured elemental content (%): C, 84.86; H, 4.74; N, 1.84.

[0219] Synthesis example 4:

[0220]

[0221] Following the preparation method of compound 15 in Synthetic Example 1, b-15, d-15, and f-15 were replaced with equimolar amounts of b-101, d-101, and f-101, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium diethyl ether solution, yielding compound 101 (8.41 g); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 757.2814 (theoretical value: 757.2803). Theoretical elemental content (%) C 56 H 39 NS: C, 88.74; H, 5.19; N, 1.85. Measured elemental content (%): C, 88.76; H, 5.15; N, 1.83.

[0222] Synthesis example 5:

[0223]

[0224] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-132, e-132, and f-132, respectively, to obtain compound 132 (9.29 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 773.3671 (theoretical value: 773.3658). Theoretical elemental content (%) C 58 H 47 NO: C, 90.00; H, 6.12; N, 1.81. Measured elemental content (%): C, 90.03; H, 6.10; N, 1.84.

[0225] Synthesis example 6:

[0226]

[0227]

[0228] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, e-140, and f-140, respectively, to obtain compound 140 (10.23 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 821.3676 (theoretical value: 821.3658). Theoretical elemental content (%) C 62 H 47 NO: C, 90.59; H, 5.76; N, 1.70. Measured elemental content (%): C, 90.57; H, 5.78; N, 1.72.

[0229] Synthesis example 7:

[0230]

[0231] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-180, e-132, and f-140, respectively, to obtain compound 180 (9.11 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 831.2974 (theoretical value: 831.2960). Theoretical elemental content (%) C 62 H 41 NS: C, 89.50; H, 4.97; N, 1.68. Measured elemental content (%): C, 89.54; H, 4.95; N, 1.64.

[0232] Synthesis example 8:

[0233]

[0234] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, e-15, and f-15 were replaced with equimolar amounts of a-54, a-77, d-186, e-132, and f-186, respectively, to obtain compound 186 (9.61 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 831.2978 (theoretical value: 831.2960). Theoretical elemental content (%) C 62 H 41 NS: C, 89.50; H, 4.97; N, 1.68. Measured elemental content (%): C, 89.53; H, 4.95; N, 1.66.

[0235] Synthesis example 9:

[0236]

[0237] Following the preparation method of compound 15 in Synthetic Example 1, b-15, e-15, and f-15 were replaced with equimolar amounts of a-77, e-132, and f-190, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution, yielding compound 190 (7.80 g); HPLC purity ≥ 99.84%. Mass spectrometry m / z: 721.2815 (theoretical value: 721.2803). Theoretical elemental content (%) C 53 H 39 NS: C, 88.17; H, 5.45; N, 1.94. Measured elemental content (%): C, 88.14; H, 5.48; N, 1.91.

[0238] Synthesis example 10:

[0239]

[0240] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-200, a-200, and f-200, respectively, to obtain compound 200 (9.44 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 757.2993 (theoretical value: 757.2981). Theoretical elemental content (%) C 56 H 39 NO2: C, 88.74; H, 5.19; N, 1.85. Measured elemental content (%): C, 88.76; H, 5.16; N, 1.87.

[0241] Synthesis example 11:

[0242]

[0243] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-201, a-201, and f-201, respectively, to obtain compound 201 (10.01 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 833.3283 (theoretical value: 833.3294). Theoretical elemental content (%) C 62 H 43 NO2: C, 89.29; H, 5.20; N, 1.68. Measured elemental content (%): C, 89.26; H, 5.24; N, 1.66.

[0244] Synthesis example 12:

[0245]

[0246] Following the preparation method of compound 15 in Synthetic Example 1, a-15, d-15, and f-15 were replaced with equimolar amounts of a-54, d-101, and f-224, respectively, to obtain compound 224 (8.98 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 767.3197 (theoretical value: 767.3188). Theoretical elemental content (%) C 58 H 41 NO: C, 90.71; H, 5.38; N, 1.82. Measured elemental content (%): C, 90.74; H, 5.35; N, 1.84.

[0247] Synthesis example 13:

[0248]

[0249] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-226, b-226, e-54, and f-224, respectively, to obtain compound 224 (9.41 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 793.3357 (theoretical value: 793.3345). Theoretical elemental content (%) C 60 H 43 NO: C, 90.76; H, 5.46; N, 1.76. Measured elemental content (%): C, 90.78; H, 5.44; N, 1.73.

[0250] Synthesis example 14:

[0251]

[0252] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-140, and f-231, respectively, to obtain compound 231 (10.61 g); HPLC purity ≥ 99.94%. Mass spectrometry m / z: 841.3356 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.27; H, 5.17; N, 1.68.

[0253] Synthesis example 15:

[0254]

[0255] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-200, and f-236, respectively, to obtain compound 236 (10.36 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 841.3359 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.26; H, 5.17; N, 1.68.

[0256] Synthesis example 16:

[0257]

[0258] Following the preparation method of compound 15 in Synthetic Example 1, b-15, e-15, and f-15 were replaced with equimolar amounts of a-200, e-252, and f-140, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution, yielding compound 252 (9.76 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 855.3515 (theoretical value: 855.3501). Theoretical elemental content (%) C 65 H 45 NO: C, 91.20; H, 5.30; N, 1.64. Measured elemental content (%): C, 91.24; H, 5.33; N, 1.62.

[0259] Synthesis example 17:

[0260]

[0261] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, e-272, and f-272, respectively, to obtain compound 272 (9.88 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 833.3667 (theoretical value: 833.3658). Theoretical elemental content (%) C 63 H 47 NO: C, 90.72; H, 5.68; N, 1.68. Measured elemental content (%): C, 90.75; H, 5.66; N, 1.65.

[0262] Synthesis example 18:

[0263]

[0264] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, e-15, and f-15 were replaced with equimolar amounts of a-200, a-200, d-186, e-276, and f-276, respectively, to obtain compound 276 (8.68 g); HPLC purity ≥99.87%. Mass spectrometry m / z: 771.2785 (theoretical value: 771.2773). Theoretical elemental content (%) C 56 H 37 NO3: C, 87.14; H, 4.83; N, 1.81. Measured element content (%): C, 87.17; H, 4.80; N, 1.84.

[0265] Synthesis example 19:

[0266]

[0267] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-200, a-77, e-54, and f-289, respectively, to obtain compound 289 (9.06 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 773.2764 (theoretical value: 773.2752). Theoretical elemental content (%) C 56 H 39 NOS: C, 86.90; H, 5.08; N, 1.81. Measured elemental content (%): C, 86.92; H, 5.05; N, 1.84.

[0268] Synthesis example 20:

[0269]

[0270] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-77, a-77, and f-297, respectively, to obtain compound 297 (10.59 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 881.3163 (theoretical value: 881.3150). Theoretical elemental content (%) C 63 H 47 NS2: C, 85.77; H, 5.37; N, 1.59. Measured elemental content (%): C, 85.75; H, 5.39; N, 1.56.

[0271] Synthesis example 21:

[0272]

[0273] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-300, and f-300, respectively, to obtain compound 300 (10.19 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 859.3285 (theoretical value: 859.3273). Theoretical elemental content (%) C 64 H 45 NS: C, 89.37; H, 5.27; N, 1.63. Measured elemental content (%): C, 89.35; H, 5.23; N, 1.66.

[0274] Synthesis example 22:

[0275]

[0276]

[0277] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-301, and f-200, respectively, to obtain compound 301 (9.70 g); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 873.3440 (theoretical value: 873.3429). Theoretical elemental content (%) C 65 H 47 NS: C, 89.31; H, 5.42; N, 1.60. Measured elemental content (%): C, 89.35; H, 5.40; N, 1.62.

[0278] Synthesis example 23:

[0279]

[0280] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, a-77, e-303, and f-303, respectively, to obtain compound 303 (9.60 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 809.3125 (theoretical value: 809.3116). Theoretical elemental content (%) C 60 H 43 NS: C, 88.96; H, 5.35; N, 1.73. Measured elemental content (%): C, 88.94; H, 5.37; N, 1.75.

[0281] Synthesis example 24:

[0282]

[0283] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-311, and f-311, respectively, to obtain compound 311 (9.45 g); HPLC purity ≥ 99.84%. Mass spectrometry m / z: 895.3284 (theoretical value: 895.3273). Theoretical elemental content (%) C 67 H 45 NS: C, 89.80; H, 5.06; N, 1.56. Measured elemental content (%): C, 89.84; H, 5.04; N, 1.53.

[0284] Synthesis example 25:

[0285]

[0286]

[0287] Following the preparation method of compound 15 in Synthetic Example 1, b-15, e-15, and f-15 were replaced with equimolar amounts of a-77, e-333, and f-236, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution, yielding compound 333 (9.84 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 851.2693 (theoretical value: 851.2680). Theoretical elemental content (%) C 61 H 41 NS2: C, 85.98; H, 4.85; N, 1.64. Measured elemental content (%): C, 85.95; H, 4.87; N, 1.67.

[0288] Synthesis example 26:

[0289]

[0290] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-200, a-200, e-132, and f-336, respectively, to obtain compound 336 (10.37 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 803.2836 (theoretical value: 803.2824). Theoretical elemental content (%) C 60 H 37 NO2: C, 89.64; H, 4.64; N, 1.74. Measured elemental content (%): C, 89.62; H, 4.62; N, 1.77.

[0291] Synthesis example 27:

[0292]

[0293] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, e-392, and f-336, respectively, to obtain compound 392 (10.13 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 803.3197 (theoretical value: 803.3188). Theoretical elemental content (%) C 61 H 41 NO: C, 91.13; H, 5.14; N, 1.74. Measured elemental content (%): C, 91.16; H, 5.12; N, 1.72.

[0294] Synthesis example 28:

[0295]

[0296] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-398, e-132, and f-336, respectively, to obtain compound 398 (10.33 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 839.3196 (theoretical value: 839.3188). Theoretical elemental content (%) C 64 H 41 NO: C, 91.51; H, 4.92; N, 1.67. Measured elemental content (%): C, 91.53; H, 4.94; N, 1.64.

[0297] Synthesis example 29:

[0298]

[0299] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, e-401, and f-336, respectively, to obtain compound 401 (10.54 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 835.3281 (theoretical value: 835.3270). Theoretical elemental content (%) C 61 H 45 NOSi: C, 87.63; H, 5.43; N, 1.68. Measured elemental content (%): C, 87.65; H, 5.46; N, 1.66.

[0300] Synthesis example 30:

[0301]

[0302] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-406, e-132, and f-406, respectively, to obtain compound 406 (9.52 g); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 813.3045 (theoretical value: 813.3032). Theoretical elemental content (%) C 62 H 39 NO: C, 91.48; H, 4.83; N, 1.72. Measured elemental content (%): C, 91.44; H, 4.85; N, 1.75.

[0303] Synthesis example 31:

[0304]

[0305] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-408, b-140, e-132, and f-336, respectively, to obtain compound 408 (9.64 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 813.3048 (theoretical value: 813.3032). Theoretical elemental content (%) C 62 H 39 NO: C, 91.48; H, 4.83; N, 1.72. Measured elemental content (%): C, 91.45; H, 4.82; N, 1.75.

[0306] Synthesis example 32:

[0307]

[0308] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-200, e-415, and f-415, respectively, to obtain compound 415 (10.90 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 844.3514 (theoretical value: 844.3502). Theoretical elemental content (%) C 64 H 36 D5NO: C, 90.96; H, 5.49; N, 1.66. Measured elemental content (%): C, 90.98; H, 5.46; N, 1.68.

[0309] Synthesis example 33:

[0310]

[0311] Following the preparation method of compound 15 in Synthetic Example 1, b-15, e-15, and f-15 were replaced with equimolar amounts of a-200, e-448, and f-448, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution, yielding compound 448 (9.91 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 835.3823 (theoretical value: 835.3814). Theoretical elemental content (%) C 63 H 49 NO: C, 90.50; H, 5.91; N, 1.68. Measured elemental content (%): C, 90.53; H, 5.93; N, 1.66.

[0312] Synthesis example 34:

[0313]

[0314] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-460, a-460, e-132, and f-406, respectively, to obtain compound 406 (9.98 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 863.2694 (theoretical value: 863.2680). Theoretical elemental content (%) C 62 H 41 NS2: C, 86.18; H, 4.78; N, 1.62. Measured elemental content (%): C, 86.15; H, 4.76; N, 1.64.

[0315] Synthesis example 35:

[0316]

[0317]

[0318] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-101, e-132, and f-480, respectively, to obtain compound 480 (10.97 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 891.3886 (theoretical value: 891.3899). Theoretical elemental content (%) C 66 H 53 NS: C, 88.85; H, 5.99; N, 1.57. Measured elemental content (%): C, 88.87; H, 5.96; N, 1.55.

[0319] Synthesis example 36:

[0320]

[0321] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-485, a-77, e-132, and f-336, respectively, to obtain compound 485 (9.78 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 835.3285 (theoretical value: 835.3273). Theoretical elemental content (%) C 62 H 45 NS: C, 89.07; H, 5.43; N, 1.68. Measured elemental content (%): C, 89.09; H, 5.41; N, 1.66.

[0322] Synthesis example 37:

[0323]

[0324] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-200, a-200, and f-336, respectively, to obtain compound 508 (11.08 g); HPLC purity ≥ 99.93%. Mass spectrometry m / z: 879.3149 (theoretical value: 879.3137). Theoretical elemental content (%) C 66 H 41 NO2: C, 90.08; H, 4.70; N, 1.59. Measured elemental content (%): C, 90.06; H, 4.72; N, 1.57.

[0325] Synthesis example 38:

[0326]

[0327]

[0328] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, and f-15 were replaced with equimolar amounts of a-200, b-531, d-531, and f-531, respectively, to obtain compound 531 (10.16 g); HPLC purity ≥ 99.91%. Mass spectrometry m / z: 879.3146 (theoretical value: 879.3137). Theoretical elemental content (%) C 66 H 41 NO2: C, 90.08; H, 4.70; N, 1.59. Measured elemental content (%): C, 90.05; H, 4.73; N, 1.56.

[0329] Synthesis example 39:

[0330]

[0331] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, e-545, and f-336, respectively, to obtain compound 545 (10.65 g); HPLC purity ≥ 99.96%. Mass spectrometry m / z: 844.3516 (theoretical value: 844.3502). Theoretical elemental content (%) C 64 H 36 D5NO: C, 90.96; H, 5.49; N, 1.66. Measured elemental content (%): C, 90.98; H, 5.46; N, 1.68.

[0332] Synthesis example 40:

[0333]

[0334] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, e-15, and f-15 were replaced with equimolar amounts of a-54, a-200, d-553, e-54, and f-336, respectively, to obtain compound 553 (10.08 g); HPLC purity ≥ 99.92%. Mass spectrometry m / z: 839.3197 (theoretical value: 839.3188). Theoretical elemental content (%) C 64 H 41 NO: C, 91.51; H, 4.92; N, 1.67. Measured elemental content (%): C, 91.54; H, 4.90; N, 1.65.

[0335] Synthesis example 41:

[0336]

[0337]

[0338] Following the preparation method of compound 15 in Synthetic Example 1, b-15 and f-15 were replaced with equimolar amounts of a-200 and f-589, respectively, and the A-15 solution was replaced with 43.75 ml of 1.6 M lithium methyl ether solution to obtain compound 589 (9.56 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 827.3197 (theoretical value: 827.3188). Theoretical elemental content (%) C 63 H 41 NO: C, 91.39; H, 4.99; N, 1.69. Measured elemental content (%): C, 91.37; H, 4.97; N, 1.72.

[0339] Synthesis example 42:

[0340]

[0341] Following the preparation method of compound 15 in Synthetic Example 1, b-15, e-15, and f-15 were replaced with equimolar amounts of a-200, e-627, and f-336, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution, yielding compound 627 (9.75 g); HPLC purity ≥ 99.88%. Mass spectrometry m / z: 866.3288 (theoretical value: 866.3297). Theoretical elemental content (%) C 65 H 42 N₂O: C, 90.04; H, 4.88; N, 3.23. Measured elemental content (%): C, 90.07; H, 4.84; N, 3.26.

[0342] Synthesis example 43:

[0343]

[0344] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-77, a-77, and f-634, respectively, to obtain compound 634 (10.81 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 911.2691 (theoretical value: 911.2680). Theoretical elemental content (%) C 66 H 41 NS2: C, 86.90; H, 4.53; N, 1.54. Measured elemental content (%): C, 86.93; H, 4.55; N, 1.51.

[0345] Synthesis example 44:

[0346]

[0347]

[0348] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-300, and f-336, respectively, to obtain compound 648 (9.89 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 855.2974 (theoretical value: 855.2960). Theoretical elemental content (%) C 64 H 41 NS: C, 89.79; H, 4.83; N, 1.64. Measured elemental content (%): C, 89.76; H, 4.85; N, 1.66.

[0349] Synthesis example 45:

[0350]

[0351] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, and f-15 were replaced with equimolar amounts of a-54, b-656, d-531, and f-336, respectively, to obtain compound 656 (10.14 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 855.2971 (theoretical value: 855.2960). Theoretical elemental content (%) C 64 H 41 NS: C, 89.79; H, 4.83; N, 1.64. Measured elemental content (%): C, 89.77; H, 4.85; N, 1.66.

[0352] Synthesis example 46:

[0353]

[0354] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-101, e-679, and f-336, respectively, to obtain compound 679 (9.46 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 829.2818 (theoretical value: 829.2803). Theoretical elemental content (%) C 62 H 39 NS: C, 89.71; H, 4.74; N, 1.69. Measured elemental content (%): C, 89.73; H, 4.77; N, 1.65.

[0355] Synthesis example 47:

[0356]

[0357]

[0358] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-685, e-685, and f-336, respectively, to obtain compound 685 (9.70 g); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 885.2537 (theoretical value: 885.2524). Theoretical elemental content (%) C 64 H 39 NS2: C, 86.75; H, 4.44; N, 1.58. Measured elemental content (%): C, 86.78; H, 4.47; N, 1.56.

[0359] Synthesis example 48:

[0360]

[0361] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, a-200, e-54, and f-704, respectively, to obtain compound 704 (8.41 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 727.2889 (theoretical value: 727.2875). Theoretical elemental content (%) C 55 H 37 NO: C, 90.75; H, 5.12; N, 1.92. Measured elemental content (%): C, 90.72; H, 5.14; N, 1.95.

[0362] Synthesis example 49:

[0363]

[0364] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-54, b-706, and f-704, respectively, to obtain compound 706 (9.03 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 802.3357 (theoretical value: 802.3348). Theoretical elemental content (%) C 61 H 42 N2: C, 91.24; H, 5.27; N, 3.49. Measured elemental content (%): C, 91.27; H, 5.25; N, 3.45.

[0365] Synthesis example 50:

[0366]

[0367]

[0368] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-140, d-715, e-132, and f-336, respectively, to obtain compound 715 (9.28 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 835.3464 (theoretical value: 835.3450). Theoretical elemental content (%) C 62 H 45 NO2: C, 89.07; H, 5.43; N, 1.68. Measured elemental content (%): C, 89.09; H, 5.47; N, 1.65.

[0369] Synthesis example 51:

[0370]

[0371] Following the preparation method of compound 15 in Synthetic Example 1, b-15, d-15, e-15, and f-15 were replaced with equimolar amounts of b-140, d-731, e-731, and f-731, respectively. Solution A-15 was replaced with 43.75 ml of 1.6 M lithium methyl ether solution to obtain compound 731 (9.98 g); HPLC purity ≥ 99.87%. Mass spectrometry m / z: 886.3372 (theoretical value: 886.3359). Theoretical elemental content (%) C 65 H 43 FN2O: C, 88.01; H, 4.89; N, 3.16. Measured elemental content (%): C, 88.04; H, 4.86; N, 3.18.

[0372] Synthesis example 52:

[0373]

[0374] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-15 were replaced with equimolar amounts of a-739, a-739, and f-739, respectively, to obtain compound 739 (8.47 g); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 773.2223 (theoretical value: 773.2211). Theoretical elemental content (%) C 55 H 35 NS2: C, 85.35; H, 4.56; N, 1.81. Measured elemental content (%): C, 85.33; H, 4.54; N, 1.84.

[0375] Synthesis example 53:

[0376]

[0377]

[0378] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, and f-15 were replaced with equimolar amounts of a-54, a-77, d-748, and f-748, respectively, to obtain compound 748 (8.98 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 767.2658 (theoretical value: 767.2647). Theoretical elemental content (%) C 57 H 37 NS: C, 89.15; H, 4.86; N, 1.82. Measured elemental content (%): C, 89.13; H, 4.84; N, 1.85.

[0379] Synthesis example 54:

[0380]

[0381] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, e-15, and f-15 were replaced with equimolar amounts of a-54, b-101, e-751, and f-751, respectively, to obtain compound 751 (9.40 g); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 846.3080 (theoretical value: 846.3069). Theoretical elemental content (%) C 62 H 42 N2S: C, 87.91; H, 5.00; N, 3.31. Measured elemental content (%): C, 87.95; H, 5.03; N, 3.29.

[0382] Synthesis example 55:

[0383]

[0384] Following the preparation method of compound 15 in Synthetic Example 1, D-15, e-15, and f-15 were replaced with equimolar amounts of D-480, e-132, and D-303, respectively, to obtain compound 794 (9.93 g); HPLC purity ≥ 99.90%. Mass spectrometry m / z: 837.2536 (theoretical value: 837.2524). Theoretical elemental content (%) C 60 H 39 NS2: C, 85.99; H, 4.69; N, 1.67. Measured elemental content (%): C, 85.96; H, 4.67; N, 1.69.

[0385] Synthesis example 56:

[0386]

[0387] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, d-15, and f-15 were replaced with equimolar amounts of a-200, a-200, d-887, and f-224, respectively, to obtain compound 887 (10.38 g); HPLC purity ≥ 99.95%. Mass spectrometry m / z: 833.3309 (theoretical value: 833.3294). Theoretical elemental content (%) C 62 H 43 NO2: C, 89.29; H, 5.20; N, 1.68. Measured elemental content (%): C, 89.26; H, 5.23; N, 1.70.

[0388] Synthesis example 57:

[0389]

[0390] Following the preparation method of compound 15 in Synthetic Example 1, b-15 was replaced with an equimolar amount of b-977, and the A-15 solution was replaced with 43.75 ml of 1.6 M methyllithium in diethyl ether solution, yielding compound 977 (7.31 g); HPLC purity ≥ 99.86%. Mass spectrometry m / z: 632.2297 (theoretical value: 632.2286). Theoretical elemental content (%) C 45 H 32 N₂S: C, 85.41; H, 5.10; N, 4.43. Measured elemental content (%): C, 85.44; H, 5.12; N, 4.41.

[0391] Synthesis example 58:

[0392]

[0393] Following the preparation method of compound 15 in Synthetic Example 1, a-15, b-15, and f-77 were replaced with equimolar amounts of a-77, a-77, and f-992, respectively, to obtain compound 992 (8.90 g); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 750.2175 (theoretical value: 750.2163). Theoretical elemental content (%) C 52 H 34 N2S2: C, 83.17; H, 4.56; N, 3.73. Measured elemental content (%): C, 83.13; H, 4.54; N, 3.75.

[0394] Device Examples

[0395] 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%.

[0396] 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.

[0397] Example 1: Fabrication of Organic Electroluminescent Device 1

[0398] HAT-CN was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 5 nm; p-BPD was vacuum-deposited on the hole injection layer as a first hole transport layer with a thickness of 65 nm; compound 54 of the present invention was vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 35 nm; m-CBP:Ir(ppy)2(acac)=90:10(wt%) was vacuum-deposited on the second hole transport layer as a light-emitting layer with a thickness of 42 nm; ET-1:Liq=1:1(wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 30 nm; Liq was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.2 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0399] Examples 2-30: Fabrication of Organic Electroluminescent Devices 2-30

[0400] Replacing compound 54 in the second hole transport layer of Example 1 with compounds 101, 132, 180, 190, 226, 231, 236, 252, 272, 289, 297, 300, 303, 311, 392, 401, 408, 448, 485, 508, 531, 589, 627, 634, 685, 715, 731, 748, and 794 respectively, organic electroluminescent devices 2-30 are obtained.

[0401] Comparative Examples 1-2: Fabrication of Comparative Organic Electroluminescent Devices 1-2

[0402] By replacing compound 54 in the second hole transport layer of Example 1 with R-1 and R-2 respectively, comparative organic electroluminescent devices 1-2 were obtained.

[0403]

[0404] The luminescence characteristics of the organic electroluminescent devices prepared in Examples 1-30 and Comparative Examples 1-2 of this invention are shown in Table 1.

[0405] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0406]

[0407]

[0408] As shown in Table 1, organic electroluminescent devices containing the triarylamine compound of Formula 1 of the present invention in the hole transport layer have good photoelectric performance, specifically, they have lower driving voltage, higher luminous efficiency, and longer lifespan.

[0409] Example 31: Fabrication of Organic Electroluminescent Device 31

[0410] HAT-CN was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 5 nm; Compound 15 of the present invention was vacuum-deposited on the hole injection layer as a hole transport layer with a thickness of 45 nm; BH-1:BD-1 = 97:3 (wt%) was vacuum-deposited on the hole transport layer as a light-emitting layer with a thickness of 44 nm; ET-2:Liq = 1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 28 nm; Liq was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.0 nm; Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 150 nm.

[0411] Examples 31-59: Fabrication of organic electroluminescent devices 31-59

[0412] Replacing compound 15 in the hole transport layer of Example 31 with compounds 77, 140, 186, 200, 201, 224, 231, 276, 301, 333, 336, 398, 406, 415, 460, 480, 545, 553, 648, 656, 679, 704, 706, 739, 751, 887, 977, and 992 respectively, organic electroluminescent devices 31-59 are obtained.

[0413] Comparative Examples 3-4: Fabrication of Comparative Organic Electroluminescent Devices 3-4

[0414] By replacing compound 15 in the hole transport layer of Example 31 with R-1 and R-2 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 3-4 were obtained.

[0415]

[0416] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 31-59 and Comparative Examples 3-4 of this invention are shown in Table 1.

[0417] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0418]

[0419]

[0420] As shown in Table 2, organic electroluminescent devices containing the triarylamine compound of Formula 1 of this invention in the hole transport layer have good photoelectric performance, specifically, they have lower driving voltage, higher luminous efficiency, and longer lifespan.

[0421] 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 triarylamine compound characterized in that, represented by the following formula 1, wherein the Ar1 is selected from the group consisting of the group represented by formula 1-a1, the R1 is selected from the group represented by formula 1-b, ； said ring A in is selected from one of the following groups: the m is selected from an integer from 0 to 2, the m1 is selected from an integer from 0 to 4, the m2 is selected from an integer from 0 to 6, the m3 is selected from an integer from 0 to 8, said X is selected from O, S, N(R x ), said R x is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; the R4 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted phenyl; the R5 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl; the R2 is selected from one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or the group represented by formula 1-b; the n is selected from an integer from 0 to 4, the n1 is selected from an integer from 0 to 3, the R3 is the same or different and is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted phenyl, or two adjacent R3s are bonded to each other to form a substituted or unsubstituted benzene ring; the Ar2 is selected from one of the group represented by formula 1-a1 or the group represented by the following formula, the e1 is selected from an integer from 0 to 5, the e2 is selected from an integer from 0 to 4, the e3 is selected from an integer from 0 to 7, the e4 is selected from an integer from 0 to 9, the e5 is selected from an integer from 0 to 3, the e6 is selected from an integer from 0 to 2, the e7 is selected from an integer from 0 to 6, the e8 is selected from an integer from 0 to 8, the e9 is selected from an integer from 0 to 10, The The R6 in the same or different group is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted phenyl. The The R6 in the same or different is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted phenyl; The The R6 in the sample, whether the same or different, is selected from one of hydrogen, deuterium, and tritium; said R 60 the same or different, one selected from the group consisting of hydrogen, deuterium, tritium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group, a substituted or unsubstituted phenyl group, or Two adjacent R 60 They bond with each other to form substituted or unsubstituted benzene rings; R y is selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl;​ the R y one, which is the same or different, is selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The R e The same or different from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl groups; the Ar3 is selected from one of the group represented by the following formula, the f1 is selected from an integer from 0 to 5, the f2 is selected from an integer from 0 to 4, the f3 is selected from an integer from 0 to 7, the f4 is selected from an integer from 0 to 9, the f5 is selected from an integer from 0 to 3, the f6 is selected from an integer from 0 to 2, the f7 is selected from an integer from 0 to 6, the f8 is selected from an integer from 0 to 8, the f9 is selected from an integer from 0 to 10, The The R7 in the same or different group is selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted tripropylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted phenyl. The The R7 values, whether identical or different, are selected from one of hydrogen, deuterium, and tritium. The The R7 in the same or different is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted phenyl; The R 70 The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl; The R ` one selected from the group consisting of hydrogen, deuterium, tritium; said R w one, identical or different, selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; the L2, L4 is independently selected from one of a single bond or the group represented by the following formula, the L3 is selected from one of a single bond or the group represented by the following formula, the k1 is selected from an integer from 0 to 4, the k2 is selected from an integer from 0 to 3; the R8 is the same or different and is selected from one of hydrogen, deuterium, tritium; the L1 is selected from one of a single bond or the group represented by the following formula, the g1 is selected from an integer from 0 to 4; the R9 is the same or different and is selected from one of hydrogen, deuterium, tritium; the "substitution" in the "substituted or unsubstituted" represents a substituent including the group represented by the following formula, deuterium, tritium.

2. A triarylamine compound characterized in that, represented by the following formula 1, wherein the Ar1 is selected from the group represented by formula 1-a2, said R 10 is selected from a group consisting of radicals of formula 1-c, ； said and Ring A in the above is selected from one of the following groups: the m is selected from an integer from 0 to 2, the m1 is selected from an integer from 0 to 4, the X is selected from one of O, S; the R4 is the same or different and is selected from one of hydrogen, deuterium, tritium; the R5 is the same or different and is selected from one of hydrogen, deuterium, tritium; the R2 is selected from one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a group represented by formula 1-b; the n is selected from an integer from 0 to 4, the R3 is the same or different and is selected from one of hydrogen, deuterium, tritium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group; the Ar2 is selected from one of the following groups, the e2 is selected from an integer from 0 to 4, the e5 is selected from an integer from 0 to 3, The R 60 The same or different is selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl; the Ar3 is selected from one of the following groups, the f1 is selected from an integer from 0 to 5, the f2 is selected from an integer from 0 to 4, the R7 is the same or different and is selected from one of hydrogen, deuterium, tritium, halogen, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted pentyl group, a substituted or unsubstituted hexyl group; the L2, L4 is selected from a single bond, the L3 is selected from a single bond or one of the following groups, the k1 is selected from an integer from 0 to 4, the k2 is selected from an integer from 0 to 3; the R8 is the same or different and is selected from one of hydrogen, deuterium, tritium; the L1 is selected from a single bond; the "substituted" in the "substituted or unsubstituted" represents a substituent including the following groups, deuterium, tritium.

3. The triarylamine compound according to claim 1, characterized by the Ar2 is selected from one of the following groups, 。 4. The triarylamine compound according to claim 1, characterized by the Ar3 is selected from one of the following groups, 。 5. The compound of claim 1, wherein said Ring A in the above is selected from one of the following groups: 。 6. The compound of claim 1, wherein the L2, L3, L4 is independently selected from a single bond or one of the following groups, ； the L1 is selected from a single bond.

7. A triarylamine compound characterized in that, the triarylamine compound is selected from at least one of the following structures, 。 8. An organic electroluminescent device, characterized by the organic electroluminescence device contains the triarylamine compound according to any one of claims 1 to 7. the organic electroluminescence device contains the triarylamine compound according to any one of claims 1 to 7.

Images