A triarylamine compound and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The triarylamine compound has good thermal stability, high hole mobility and a suitable HOMO energy level, and is used as a hole transport material in the organic electroluminescent device, which can effectively reduce the hole transport resistance, improve the injection and transport efficiency of holes in the device, make the efficient recombination of electrons and holes in the light-emitting layer, effectively reduce the driving voltage of the device, improve the light-emitting efficiency of the device, reduce the movement of excitons to the outside of the light-emitting layer, avoid interface light emission, reduce the loss of the device, and prolong the service life of the device.The triarylamine compound can be applied to the fields of display, illumination and organic solar cells.

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) are a technology that uses organic materials to directly convert electrical energy into light energy. The principle is that under the influence of an external electric field, charge carriers are injected through electrodes. After passing through the organic functional layer, the charge carriers recombine in the light-emitting layer to form excitons, which then emit light through transitions. OLEDs have advantages such as thin and light weight, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and flexibility, and have been widely used in lighting and display fields.

[0003] With the development of organic light-emitting diodes (OLEDs), their structures are constantly being improved. From the earliest single-layer device structures to double-layer structures, and then to multi-layer structures, the performance of OLEDs has been enhanced through continuous structural improvements. Currently, sandwich structures are commonly used, where an organic functional layer is placed between the cathode and anode on both sides of the device. This organic functional layer can include hole transport regions, light-emitting layers, and electron transport regions. The hole transport regions include hole injection layers, hole transport layers, and electron blocking layers, while the electron transport regions include electron injection layers, electron transport layers, and hole blocking layers.

[0004] The hole transport layer, serving as the connecting layer between the anode and the emissive layer, plays two main roles: first, it facilitates the transport of holes injected from the anode to the emissive layer and, to some extent, blocks the diffusion of electrons from the emissive layer to the hole transport layer, thus better confining electrons within the emissive layer and maximizing carrier recombination; second, it simultaneously lowers the energy barrier during hole injection, improving hole injection efficiency and consequently enhancing the device's brightness, efficiency, and lifetime. Hole transport materials require high hole mobility to ensure good hole transport performance and improve device luminous efficiency; good film-forming properties and thermal stability to extend device lifespan; and suitable HOMO orbital energy levels to reduce driving voltage and ensure effective hole injection and transport within the device. However, current hole transport materials still suffer from poor hole mobility, low thermal stability, poor film-forming properties, and energy level mismatch, leading to increased driving voltage, reduced luminous efficiency, and shortened lifetime in organic light-emitting diodes (OLEDs).

[0005] To further improve the performance of organic electroluminescent devices and effectively address their existing problems, it is necessary to develop organic electroluminescent materials with superior performance, among which hole transport materials are particularly important. Summary of the Invention

[0006] To address the problems existing in the prior art, the present invention provides a triarylamine compound and its organic electroluminescent device.

[0007] This invention provides a triarylamine compound, represented by the following formula 1,

[0008]

[0009] Wherein, R1, R2, R3, and R4 are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1, two R2, two R3, and two R4 can be bonded to each other to form a substituted or unsubstituted ring;

[0010] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3 or 4; the n4 is selected from 0, 1, 2, 3 or 4.

[0011] The Ar1 is selected from the group shown in Formula 1-a below.

[0012]

[0013] The asterisk (*) indicates the connection point with bridge L1;

[0014] The W is selected from single bonds or CR. a R b ;

[0015] The R a R b The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0016] The R5, R6, R7, and R8 are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R5, two R6, two R7, and two R8 can be bonded to each other to form a substituted or unsubstituted ring;

[0017] The u1 is selected from 0 or 1;

[0018] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3, 4 or 5.

[0019] The Ar2 is selected from the groups shown in Formula 1-b below.

[0020]

[0021] The Y is selected from O, S, or NR. c ;

[0022] The x that is the same or different is selected from CR t Or N;

[0023] The R c It is selected from one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0024] The R t Selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R t They bond together to form substituted or unsubstituted rings;

[0025] The R d It is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0026] The s1 is selected from 0, 1, or 2;

[0027] The L0, L1, and L2 are the same or different and are selected from one of the single-bonded, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups.

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

[0029] Beneficial effects: The triarylamine compounds of Formula 1 of this invention have good thermal stability, high hole mobility, and suitable HOMO energy levels. When used as hole transport materials in organic electroluminescent devices, they can effectively reduce hole transport resistance, improve hole injection and transport efficiency within the device, increase the recombination efficiency of electrons and holes in the emitting layer, effectively reduce the driving voltage of the device, and improve the luminous efficiency of the device. They can also reduce the movement of excitons to the outside of the emitting layer, avoid interfacial luminescence, reduce device losses, and extend the device's lifespan. 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 the compounds of the present invention, 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.

[0032] The halogens described in this invention include fluorine, chlorine, bromine, and iodine.

[0033] In this invention, "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.

[0034] In this invention, "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, it does not include the number of carbon atoms in the substituent. For example, in "substituted or unsubstituted C6~C60 aryl group", "C6~C60" represents the number of carbon atoms in the unsubstituted "aryl group". When the "aryl group" has a substituent, it does not include the number of carbon atoms in the substituent. In "fused cycloalcoholic group of substituted or unsubstituted C3~C25 alicyclic ring and C6~C30 aromatic ring", "C3~C25" represents the number of carbon atoms in the unsubstituted "alicyclic ring". When the "alicyclic ring" has a substituent, it does not include the number of carbon atoms in the substituent; "C6~C30" represents the number of carbon atoms in the unsubstituted "aromatic ring". When the "aromatic ring" has a substituent, it does not include the number of carbon atoms in the substituent. And so on.

[0035] In this invention, 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.

[0036] For example, Can represent Can represent Can represent And so on.

[0037] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent And so on.

[0038] In this invention, "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. Examples are shown below:

[0039]

[0040] Furthermore, a ring formed by the bonding of adjacent groups can connect with another ring to form a helical structure. See the example below:

[0041]

[0042] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, eight-membered rings, fused rings, spirocyclic rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but are not limited to these.

[0043] In this invention, "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 C1-C15 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C2-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 heteroaromatic 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, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. Substituents include benzo[a]yl, fluoranyl, benzocyclopropane, benzocyclobutane, dihydroindenyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl, fluorenyl, spirodifluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can bond to form a ring.

[0044] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched alkyl group. When the chain alkyl group described in this invention has three or more carbon atoms, it includes its isomers; for example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The alkyl group has a carbon number of C1 to C30, preferably C1 to C25, preferably C1 to C20, preferably C1 to C15, and even more preferably C1 to C10.

[0045] The silyl group mentioned in this invention refers to -Si(R) k )3 groups, wherein each R kThe 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 k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl groups, and substituted or unsubstituted C3-C30 cycloalkyl groups. The alkyl group preferably has C1-C20 carbon atoms, more preferably C1-C15, even more preferably C1-C10, and most preferably C1-C8. The cycloalkyl group preferably has C3-C20 carbon atoms, more preferably C3-C15, even more preferably C3-C10, and most preferably C3-C7. Preferably, each R... k 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 silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0046] The cycloalkyl group described in this invention 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 cycloalkyl groups include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, fentanyl, isocamphenyl, etc., but are not limited thereto. The cycloalkyl group has 3 to 30 carbon atoms, preferably 3 to 25, preferably 3 to 20, preferably 3 to 15, and more preferably 3 to 10.

[0047] The aryl group referred to in this invention 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 include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, triphenylene, fluorene, benzo[a]fluorene, spirodifluorene, spiroanthracenefluorene, pyrene, etc. Aryl, fluoranthyl, etc., but not limited to these. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C25, and even more preferably C6 to C20.

[0048] The heteroaryl group described in this invention refers to a monovalent group in which at least one carbon atom of an aryl group is replaced by a heteroatom. The heteroatom is selected from, but is not limited to, O, S, N, Si, B, P, etc. Examples of heteroaryl groups include, but are not limited to, the following groups: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophene, naphthothiophene, phenanthiophene, dibenzothiophene, benzodibenzothiophene, indolyl, naphthoindolyl, carbazoyl, benzocarbazoyl, spirofluorenexanthracene, spirofluorenexanthracene, spirofluorenexanthracene, spirofluorenexanthracene, benzodioxonyl, benzodisulfide, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophene, dihydroisobenzothiophene, phenoxazinyl, phenthiazinyl, dihydroacridyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc., but are not limited to these. The heteroaryl group can have 2 to 30 carbon atoms, preferably 2 to 25, and even more preferably 3 to 20.

[0049] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, naphthyl[a]fluorene, spirodifluorene, etc., but are not limited thereto. The arylene group has a carbon number of C6 to C30, preferably C6 to C25, more preferably C6 to C20, and more preferably C6 to C18.

[0050] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, 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 include, but are not limited to, the following groups: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthidyl, etc., but are not limited thereto. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C25, and more preferably C2 to C20.

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

[0052]

[0053] Wherein, R1, R2, R3, and R4 are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R1, two R2, two R3, and two R4 can be bonded to each other to form a substituted or unsubstituted ring;

[0054] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3 or 4; the n4 is selected from 0, 1, 2, 3 or 4.

[0055] The Ar1 is selected from the group shown in Formula 1-a below.

[0056]

[0057] The asterisk (*) indicates the connection point with bridge L1;

[0058] The W is selected from single bonds or CR. a R b ;

[0059] The R a R b The same or different is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0060] The R5, R6, R7, and R8 are the same or different and are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R5, two R6, two R7, and two R8 can be bonded to each other to form a substituted or unsubstituted ring;

[0061] The u1 is selected from 0 or 1;

[0062] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3, 4 or 5.

[0063] The Ar2 is selected from the groups shown in Formula 1-b below.

[0064]

[0065] The Y is selected from O, S, or NR. c ;

[0066] The x that is the same or different is selected from CR t Or N;

[0067] The R c It is selected from one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0068] The R t Selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R t They bond together to form substituted or unsubstituted rings;

[0069] The R d It is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0070] The s1 is selected from 0, 1, or 2;

[0071] The L0, L1, and L2 are the same or different and are selected from one of the single-bonded, substituted or unsubstituted C6-C30 aryl groups, or substituted or unsubstituted C2-C30 heteroaryl groups.

[0072] Preferably, the triarylamine compound is selected from one of formulas 1-1 to 1-3.

[0073]

[0074] Preferably, the Selected from one of the following groups,

[0075]

[0076] Preferably, R1, R2, R3, and R4 are the same or different from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted... One of the following: substituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted methylfluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R1, two R2, two R3, or two R4 can be bonded to each other to form a substituted or unsubstituted ring;

[0077] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3 or 4; the n4 is selected from 0, 1, 2, 3 or 4; the n5 is selected from 0, 1, 2 or 3; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6; and the n7 is selected from 0, 1, 2, 3, 4 or 5.

[0078] Preferably, R1, R2, R3, and R4, whether the same or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopropane, benzocyclobutane, dihydroindyl, tetrahydronaphthyl, benzocycloheptyl, indyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl. The above groups can be substituted with one or more deuterium groups.

[0079] Preferably, formula 1-a is selected from one of the following groups:

[0080]

[0081]

[0082] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3, 4 or 5; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the m7 is selected from 0, 1, 2 or 3.

[0083] More preferably, formula 1-a is selected from one of the following groups:

[0084]

[0085] Preferably, R5, R6, R7, and R8 are the same or different from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted... One of the following: substituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted methylfluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R5s, two R6s, two R7s, or two R8s may be bonded to each other to form a substituted or unsubstituted ring.

[0086] Preferably, R5, R6, R7, and R8, whether identical or different, are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopropane, benzocyclobutane, dihydroindyl, tetrahydronaphthyl, benzocycloheptyl, indyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl. The above groups may be substituted with one or more deuterium groups.

[0087] Preferably, formula 1-b is selected from one of the following groups:

[0088]

[0089] s1 is selected from 0, 1, or 2; s2 is selected from 0 or 1;

[0090] The r1 is selected from 0, 1, 2, 3 or 4; the r2 is selected from 0, 1, 2 or 3; the r3 is selected from 0, 1 or 2; the r4 is selected from 0 or 1; the r5 is selected from 0, 1, 2, 3, 4, 5 or 6; the r6 is selected from 0, 1, 2, 3, 4 or 5; the r7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the r8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0091] More preferably, formula 1-b is selected from one of the following groups:

[0092]

[0093] Preferably, the Y is selected from O, S, or NR. c ;

[0094] The R c It is selected from one of methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl, wherein the above groups may be substituted by one or more deuterium groups;

[0095] The R t Selected from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 terphenyl, substituted or unsubstituted naphthyl One of the following: substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted methylfluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R groups. t They bond with each other to form substituted or unsubstituted benzene rings;

[0096] The R dSelected from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 terphenyl, substituted or unsubstituted One of the following: naphthyl, substituted or unsubstituted anthraceneyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted methylfluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, or substituted or unsubstituted quinoxalinyl.

[0097] More preferably, formula 1-b is selected from one of the following groups:

[0098]

[0099] Preferably, the Y is selected from O or S;

[0100] Preferably, the R t It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0101] Preferably, the R d It is selected from one or a combination of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0102] Preferably, L0, L1, and L2, whether the same or different, are selected from single bonds, or from one or a combination of the following groups.

[0103]

[0104] The same or different v is selected from CR f Or N;

[0105] The R f Selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R f They bond together to form substituted or unsubstituted rings;

[0106] Z is selected from O, S, and CR. g R h Or NR i ;

[0107] The R g R h The same or different from one selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent R g R h They bond together to form substituted or unsubstituted rings;

[0108] The R i It is selected from one of the following: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0109] More preferably, L0, L1, and L2, whether the same or different, are selected from single bonds, or from one or a combination of the following groups:

[0110]

[0111] The R fThe same or different from one selected from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, two adjacent R f They bond with each other to form substituted or unsubstituted benzene rings;

[0112] The R j The same or different from one selected from 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 trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, 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 pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl;

[0113] The t1 is selected from 0, 1, 2, 3 or 4; the t2 is selected from 0, 1, 2, 3, 4, 5 or 6; the t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the t4 is selected from 0, 1, 2 or 3; the t5 is selected from 0, 1 or 2; the t6 is selected from 0 or 1; the t7 is selected from 0, 1, 2, 3, 4 or 5; and the t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0114] More preferably, the L0, L1, and L2, whether the same or different, are selected from single bonds, or from one or a combination of the following groups.

[0115]

[0116] The R fThe same or different are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl;

[0117] The R j The same or different are selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0118] Preferably, the triarylamine compound is selected from any one of the structures shown below.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132] 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 as defined above should be included.

[0133] In addition, the present invention also provides an organic electroluminescent device containing the triarylamine compound of the present invention described above.

[0134] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains the triarylamine compound of the present invention described above.

[0135] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the cathode and the anode, the organic layer including a hole transport region containing the triarylamine compound of the present invention described above.

[0136] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, the organic layer being located between the cathode and the anode, the organic layer including a hole transport region, the hole transport region including a hole transport layer, and the hole transport layer containing the triarylamine compound of the present invention described above.

[0137] Preferably, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. At least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains the triarylamine compound of the present invention described above.

[0138] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the light-emitting layer, and the first hole transport layer containing the triarylamine compound of the present invention described above.

[0139] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the light-emitting layer, and the second hole transport layer containing the triarylamine compound of the present invention described above.

[0140] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the light-emitting layer, and the first hole transport layer and the second hole transport layer containing the triarylamine compound of the present invention described above.

[0141] Preferably, the hole transport layer includes a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. The third hole transport layer contains the triarylamine compound of the present invention described above.

[0142] 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.

[0143] 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:

[0144] The anode of this invention preferably has a high work function, allowing holes to easily enter the organic layer. Conductive metal oxide films, semi-transparent metal films, etc., are commonly used, but are not limited to these. Specific examples of the anode material may include gold (Au), platinum (Pt), aluminum (Al), indium zinc oxide (IZO), indium tin oxide (ITO), zinc oxide (ZnO), tin dioxide (SnO2), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited to these.

[0145] The hole injection layer of the present invention is preferably made of a material with good hole injection capability. Hole injection materials include, but are not limited to, metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, and phenazine compounds. Specific examples of the hole injection materials may include, but are not limited to, N,N'-bis[4-di(m-tolyl)aminophenyl]-N,N'-diphenylbenzidine (DNTPD), 4,4',4"-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 4,4',4'-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), and 1,4,5,8,9,11-hexaazabenzonitrile (HAT-CN), etc.

[0146] The hole transport layer of the present invention is preferably made of a material with good hole transport performance. Hole transport materials include, but are not limited to, carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, and polyvinylcarbazole. Specific examples of the hole transport material may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4'-di(biphenyl-4-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine (TPD-10), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), 1,3,5-tris(9-carbazolyl)benzene (TCB), and 4,4',4'-tris(carbazol-9-yl)triphenylamine (TCTA). Preferably, triarylamine compounds of Formula 1 of the present invention are preferred.

[0147] The electron blocking layer of the present invention is preferably made of a material with good hole transport capability and electron blocking capability. Electron blocking materials include, but are not limited to, aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the electron blocking material may include, but are not limited to, N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, etc. Triaromatic amine compounds of Formula 1 of the present invention are preferred.

[0148] The light-emitting layer of this invention comprises a host material and a dopant material. The light-emitting layer can be a single light-emitting layer or a composite light-emitting layer stacked laterally or vertically. The doping ratio of the host material and the dopant material can be determined according to the materials 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%. The host material of the light-emitting layer not only needs to possess bipolar charge transport properties but also needs appropriate energy levels to effectively transfer excitation energy to the guest light-emitting material. The host material includes, but is not limited to, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include, but are not limited to, 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 1,3-bis(N-carbazole-yl)benzene (MCP), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), and tris(8-hydroxyquinoline)aluminum (Alq3). The doped material may be a red-emitting material, a green-emitting material, or a blue-emitting material. The doped material includes heavy metal complexes, phosphorescent rare-earth metal complexes, etc., but is not limited to these. Specific examples may include, but are not limited to, tri(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)(acetylacetone)iridium (Ir(ppy)2(acac)), di(1-phenyl-isoquinoline)(acetylacetone)iridium (Ir(piq)2(acac)), tri(1-phenyl-isoquinoline)iridium (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), etc.

[0149] The hole-blocking layer of the present invention is preferably made of a material with good electron transport capability and hole-blocking capability. The hole-blocking material includes, but is not limited to, metal complexes, heteroaromatic compounds, etc. Specific examples may include, but are not limited to, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc.

[0150] The electron transport layer of the present invention is preferably made of a material with good stability and high electron mobility. The electron transport material includes, but is not limited to, metal chelates, oxazole derivatives, thiazole derivatives, diazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc. Specific examples may include, but are not limited to, 8-hydroxyquinoline aluminum (Alq3), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-phenyl)-1-phenyl)-1H-phenanthrene[9,10-d]imidazole (ADN-PAimi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB).

[0151] The electron injection layer of the present invention is preferably made of a material with a small potential barrier to the adjacent organic transport material or host material, and simultaneously has the effect of injecting electrons from the cathode. The electron injection layer material includes, but is not limited to, metals, metal compounds, and metal oxides. Specific examples may include, but are not limited to, ytterbium (Yb), lithium fluoride (LiF), magnesium fluoride (MgF2), lithium 8-hydroxyquinoline (LiQ), cesium carbonate (Cs2CO3), and rubidium acetate (CH3COORb).

[0152] The cathode of the present invention is preferably made of a material with a low work function. The cathode material includes metals, metal alloys, etc., but is not limited thereto. Specific examples of the cathode material may include aluminum (Al), silver (Ag), gold (Au), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg:Ag), lithium-aluminum alloy (Li:Al), etc., but are not limited thereto.

[0153] The capping material of this invention has the function of coupling out light trapped within a device. The capping material includes, but is not limited to, aromatic amine derivatives, metal compounds, carbazole derivatives, etc. Specific examples may include, but are not limited to, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), etc.

[0154] 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.

[0155] The organic electroluminescent device of the present invention is mainly used in the fields of information display technology, lighting, and planar light source. 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.

[0156] The present invention is illustrated in more detail by the following embodiments; however, the embodiments described below are merely illustrative of this specification and the scope of this specification is not limited to these embodiments.

[0157] Synthesis Examples

[0158] 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.

[0159] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0160] There are no particular limitations on the preparation method of the triamine compounds shown in Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reactions, etc. The triarylamine compounds shown in Formula 1 of this invention can be prepared using the synthetic route shown below.

[0161] Synthesis route:

[0162]

[0163] The Xn is a halogen, for example, the same or different Xn are selected from Cl, Br, I.

[0164] Synthesis Example 1: Synthesis of Compound 11

[0165]

[0166] Preparation of intermediate A-11:

[0167] Under nitrogen protection, toluene (500 mL), a-11 (16.57 g, 50.00 mmol), b-11 (19.87 g, 50.00 mmol), Pd(OAc)₂ (0.17 g, 0.75 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), and tri-tert-butylphosphine (0.30 g, 1.50 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved and refluxed for 4.5 hours. After the reaction was complete, dichloromethane and distilled water were added to the reaction solution and stirred. The mixture was then separated and extracted. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed. The mixture was then purified by column chromatography using cyclohexane:ethyl acetate (9:1) as the eluent to obtain intermediate A-11 (24.62 g, yield 76%). The purity of the solid was ≥99.80% as determined by HPLC. Mass spectrometry m / z: 647.2626 (theoretical value: 647.2613).

[0168] Preparation of compound 11:

[0169] Under nitrogen protection, toluene (300 mL), A-11 (19.43 g, 30.00 mmol), c-11 (10.48 g, 30.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), and BINAP (0.59 g, 0.90 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and then refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered with diatomaceous earth, the filtrate was concentrated, recrystallized from toluene, filtered under vacuum, and washed with toluene to obtain the recrystallized solid, yielding compound 11 (19.51 g, yield 71%). HPLC analysis showed that the solid purity was ≥99.92%. Mass spectrometry m / z: 915.3510 (theoretical value: 915.3501). Theoretical elemental content (%) C 70 H 45 NO: C, 91.77; H, 4.95; N, 1.53. Measured elemental content (%): C, 91.80; H, 4.91; N, 1.56.

[0170] Synthesis Example 2: Synthesis of Compound 19

[0171]

[0172] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-19 and c-19, respectively, to obtain compound 19 (17.19 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 763.2856 (theoretical value: 763.2875). Theoretical elemental content (%) C 58 H 37NO: C, 91.19; H, 4.88; N, 1.83. Measured elemental content (%): C, 91.21; H, 4.90; N, 1.79.

[0173] Synthesis Example 3: Synthesis of Compound 40

[0174]

[0175] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-40, b-40, and c-40, respectively, to obtain compound 40 (18.67 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 888.3155 (theoretical value: 888.3141). Theoretical elemental content (%) C 67 H 40 N₂O: C, 90.51; H, 4.54; N, 3.15. Measured elemental content (%): C, 90.48; H, 4.52; N, 3.11.

[0176] Synthesis Example 4: Synthesis of Compound 54

[0177]

[0178] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-54, b-54, and c-54, respectively, to obtain compound 54 (19.02 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 945.3957 (theoretical value: 945.3971). Theoretical elemental content (%) C 72 H 51 NO: C, 91.40; H, 5.43; N, 1.48. Measured elemental content (%): C, 91.44; H, 5.39; N, 1.50.

[0179] Synthesis Example 5: Synthesis of Compound 60

[0180]

[0181] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-19, and c-60, respectively, to obtain compound 60 (18.40 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 839.3196 (theoretical value: 839.3188). Theoretical elemental content (%) C 64 H 41NO: C, 91.51; H, 4.92; N, 1.67. Measured elemental content (%): C, 91.49; H, 4.89; N, 1.72.

[0182] Synthesis Example 6: Synthesis of Compound 141

[0183]

[0184] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-141 and c-141, respectively, to obtain compound 141 (18.45 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 853.3363 (theoretical value: 853.3345). Theoretical elemental content (%) C 65 H 43 NO: C, 91.41; H, 5.08; N, 1.64. Measured elemental content (%): C, 91.39; H, 5.11; N, 1.61.

[0185] Synthesis Example 7: Synthesis of Compound 153

[0186]

[0187] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-153 and c-153, respectively, to obtain compound 153 (18.43 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 829.4118 (theoretical value: 829.4129). Theoretical elemental content (%) C 62 H 35 D 10 NO: C, 89.71; H, 6.68; N, 1.69. Measured elemental content (%): C, 89.66; H, 6.70; N, 1.72.

[0188] Synthesis Example 8: Synthesis of Compound 161

[0189]

[0190] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-161, and c-161, respectively, to obtain compound 161 (18.48 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 879.3510 (theoretical value: 879.3501). Theoretical elemental content (%) C 67 H 45NO: C, 91.44; H, 5.15; N, 1.59. Measured elemental content (%): C, 91.48; H, 5.12; N, 1.61.

[0191] Synthesis Example 9: Synthesis of Compound 164

[0192]

[0193] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-40, b-164, and c-164, respectively, to obtain compound 164 (18.16 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 889.3332 (theoretical value: 889.3345). Theoretical elemental content (%) C 68 H 43 NO: C, 91.76; H, 4.87; N, 1.57. Measured elemental content (%): C, 91.80; H, 4.84; N, 1.60.

[0194] Synthesis Example 10: Synthesis of Compound 165

[0195]

[0196] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-165, and c-165, respectively, to obtain compound 165 (18.77 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 947.4048 (theoretical value: 947.4065). Theoretical elemental content (%) C 72 H 45 D4NO: C, 91.20; H, 5.63; N, 1.48. Measured elemental content (%): C, 91.18; H, 5.68; N, 1.45.

[0197] Synthesis Example 11: Synthesis of Compound 169

[0198]

[0199] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-169 and c-169, respectively, to obtain compound 169 (18.09 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 899.4078 (theoretical value: 899.4065). Theoretical elemental content (%) C 68 H 45D4NO: C, 90.73; H, 5.93; N, 1.56. Measured elemental content (%): C, 90.70; H, 5.95; N, 1.60.

[0200] Synthesis Example 12: Synthesis of Compound 185

[0201]

[0202] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-185 and c-185, respectively, to obtain compound 185 (18.45 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 890.3289 (theoretical value: 890.3297). Theoretical elemental content (%) C 67 H 42 N₂O: C, 90.31; H, 4.75; N, 3.14. Measured elemental content (%): C, 90.27; H, 4.78; N, 3.10.

[0203] Synthesis Example 13: Synthesis of Compound 206

[0204]

[0205] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-206 and c-206, respectively, to obtain compound 206 (18.60 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 837.3020 (theoretical value: 837.3032). Theoretical elemental content (%) C 64 H 39 NO: C, 91.73; H, 4.69; N, 1.67. Measured elemental content (%): C, 91.68; H, 4.72; N, 1.70.

[0206] Synthesis Example 14: Synthesis of Compound 233

[0207]

[0208] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-233, and c-233, respectively, to obtain compound 233 (17.14 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 761.2729 (theoretical value: 761.2719). Theoretical elemental content (%) C 58 H 35NO: C, 91.43; H, 4.63; N, 1.84. Measured elemental content (%): C, 91.46; H, 4.60; N, 1.82.

[0209] Synthesis Example 15: Synthesis of Compound 257

[0210]

[0211] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-257, b-206, and c-257, respectively, to obtain compound 257 (18.37 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 913.3330 (theoretical value: 913.3345). Theoretical elemental content (%) C 70 H 43 NO: C, 91.98; H, 4.74; N, 1.53. Measured elemental content (%): C, 91.93; H, 4.77; N, 1.50.

[0212] Synthesis Example 16: Synthesis of Compound 264

[0213]

[0214] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-264, b-233, and c-264, respectively, to obtain compound 264 (18.96 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 986.4148 (theoretical value: 986.4136). Theoretical elemental content (%) C 70 H 50 D5NOSi2: C, 85.15; H, 6.12; N, 1.42. Measured elemental content (%): C, 85.18; H, 6.09; N, 1.39.

[0215] Synthesis Example 17: Synthesis of Compound 267

[0216]

[0217] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-267 and c-267, respectively, to obtain compound 267 (19.38 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 949.4270 (theoretical value: 949.4284). Theoretical elemental content (%) C 72 H 55NO: C, 91.01; H, 5.83; N, 1.47. Measured elemental content (%): C, 91.06; H, 5.79; N, 1.44.

[0218] Synthesis Example 18: Synthesis of Compound 273

[0219]

[0220] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-273 and c-273, respectively, to obtain compound 273 (18.58 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 859.3805 (theoretical value: 859.3814). Theoretical elemental content (%) C 65 H 49 NO: C, 90.77; H, 5.74; N, 1.63. Measured elemental content (%): C, 90.73; H, 5.76; N, 1.59.

[0221] Synthesis Example 19: Synthesis of Compound 314

[0222]

[0223] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-314, and c-314, respectively, to obtain compound 314 (18.74 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 931.3289 (theoretical value: 931.3273). Theoretical elemental content (%) C 70 H 45 NS: C, 90.19; H, 4.87; N, 1.50. Measured elemental content (%): C, 90.22; H, 4.90; N, 1.45.

[0224] Synthesis Example 20: Synthesis of Compound 333

[0225]

[0226] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-54, b-333, and c-333, respectively, to obtain compound 333 (18.53 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 869.3127 (theoretical value: 869.3116). Theoretical elemental content (%) C 65 H 43NS: C, 89.72; H, 4.98; N, 1.61. Measured elemental content (%): C, 89.68; H, 4.95; N, 1.65.

[0227] Synthesis Example 21: Synthesis of Compound 334

[0228]

[0229] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-334, b-206, and c-334, respectively, to obtain compound 334 (17.64 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 783.2888 (theoretical value: 783.2898). Theoretical elemental content (%) C 58 H 33 D4NS: C, 88.85; H, 5.27; N, 1.79. Measured elemental content (%): C, 88.89; H, 5.30; N, 1.75.

[0230] Synthesis Example 22: Synthesis of Compound 358

[0231]

[0232] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-358 and c-358, respectively, to obtain compound 358 (19.03 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 905.4064 (theoretical value: 905.4055). Theoretical elemental content (%) C 67 H 55 NS: C, 88.80; H, 6.12; N, 1.55. Measured elemental content (%): C, 88.76; H, 6.09; N, 1.59.

[0233] Synthesis Example 23: Synthesis of Compound 360

[0234]

[0235] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-360, and c-360, respectively, to obtain compound 360 (18.94 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 927.3339 (theoretical value: 927.3355). Theoretical elemental content (%) C 67 H 49NSSi: C, 86.69; H, 5.32; N, 1.51. Measured elemental content (%): C, 86.73; H, 5.29; N, 1.49.

[0236] Synthesis Example 24: Synthesis of Compound 370

[0237]

[0238] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-370 and c-370, respectively, to obtain compound 370 (18.30 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 883.3263 (theoretical value: 883.3273). Theoretical elemental content (%) C 66 H 45 NS: C, 89.66; H, 5.13; N, 1.58. Measured elemental content (%): C, 89.70; H, 5.08; N, 1.60.

[0239] Synthesis Example 25: Synthesis of Compound 378

[0240]

[0241] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-378, b-378, and c-378, respectively, to obtain compound 378 (17.81 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 885.3411 (theoretical value: 885.3429). Theoretical elemental content (%) C 66 H 47 NS: C, 89.46; H, 5.35; N, 1.58. Measured elemental content (%): C, 89.50; H, 5.32; N, 1.60.

[0242] Synthesis Example 26: Synthesis of Compound 419

[0243]

[0244] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-206 and c-419, respectively, to obtain compound 419 (18.70 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 853.2823 (theoretical value: 853.2803). Theoretical elemental content (%) C 64 H 39NS: C, 90.00; H, 4.60; N, 1.64. Measured elemental content (%): C, 90.04; H, 4.58; N, 1.61.

[0245] Synthesis Example 27: Synthesis of Compound 460

[0246]

[0247] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-460, b-460, and c-460, respectively, to obtain compound 460 (18.76 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 961.3733 (theoretical value: 961.3742). Theoretical elemental content (%) C 72 H 51 NS: C, 89.87; H, 5.34; N, 1.46. Measured elemental content (%): C, 89.92; H, 5.31; N, 1.44.

[0248] Synthesis Example 28: Synthesis of Compound 463

[0249]

[0250] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-60, b-463, and c-463, respectively, to obtain compound 463 (17.70 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 854.2770 (theoretical value: 854.2756). Theoretical elemental content (%) C 63 H 38 N2S: C, 88.49; H, 4.48; N, 3.28. Measured elemental content (%): C, 88.52; H, 4.51; N, 3.30.

[0251] Synthesis Example 29: Synthesis of Compound 474

[0252]

[0253] Following the same preparation method as in Synthesis Example 1, b-11 and c-11 were replaced with equimolar amounts of b-474 and c-474, respectively, to obtain compound 474 (18.17 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 903.2972 (theoretical value: 903.2960). Theoretical elemental content (%) C 68 H 41NS: C, 90.33; H, 4.57; N, 1.55. Measured elemental content (%): C, 90.29; H, 4.60; N, 1.58.

[0254] Synthesis Example 30: Synthesis of Compound 505

[0255]

[0256] Following the same preparation method as in Synthesis Example 1, a-11, b-11, and c-11 were replaced with equimolar amounts of a-505, b-505, and c-505, respectively, to obtain compound 505 (19.30 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 945.3412 (theoretical value: 945.3429). Theoretical elemental content (%) C 71 H 47 NS: C, 90.12; H, 5.01; N, 1.48. Measured elemental content (%): C, 90.09; H, 5.05; N, 1.50.

[0257] Device Examples

[0258] In this invention, the ITO glass substrate and the ITO / Ag / ITO glass substrate are 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. They are then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0259] 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.

[0260] Example 1: Fabrication of Organic Electroluminescent Device 1

[0261] DNTPD was vacuum-deposited as a hole injection layer with a thickness of 60 nm on an ITO / Ag / ITO anode; Compound 19 of this invention was vacuum-deposited as a hole transport layer with a thickness of 118 nm on the hole injection layer; RH-1, the host material, and RD-1, the dopant material, were vacuum-deposited on the hole transport layer in a ratio of RH-1:RD-1 = 98:2 (wt%) to form a light-emitting layer with a thickness of 22 nm; ET:LiQ = 1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 27 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.1 nm; Mg:Ag = 1:9 was vacuum-deposited on the electron injection layer as a cathode with a thickness of 12 nm; and then CP-1 was vacuum-deposited on the cathode as a capping layer with a thickness of 70 nm.

[0262] Examples 2-20: Fabrication of Organic Electroluminescent Devices 2-20

[0263] Replacing compound 19 in the hole transport layer of Example 1 with compounds 60, 141, 153, 165, 169, 185, 206, 233, 257, 264, 267, 273, 334, 358, 360, 370, 378, 419, and 505 respectively, while keeping other steps the same, organic electroluminescent devices 2-20 are obtained.

[0264] Comparative Examples 1-2: Fabrication of Comparative Organic Electroluminescent Devices 1-2

[0265] By replacing compound 19 in the hole transport layer of Example 1 with R-1 and R-2 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1-2 were obtained.

[0266]

[0267] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1-20 and Comparative Examples 1-2 of this invention are shown in Table 1.

[0268] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0269]

[0270]

[0271] As can be seen from Table 1, compared with comparative devices 1 to 2, the organic electroluminescent device of the present invention has a lower driving voltage, higher luminous efficiency and longer lifespan, and the device performance is superior.

[0272] Example 21: Fabrication of Organic Electroluminescent Device 21

[0273] A 60 nm thick DNTPD hole injection layer was vacuum-deposited on an ITO / Ag / ITO anode. An NPB hole transport layer with a thickness of 75 nm was vacuum-deposited on the hole injection layer. Compound 11 of this invention was vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 65 nm. On the second hole transport layer, CBP (body material) and Ir(piq)2(acac) (doped material) were vacuum-deposited in a ratio of CBP:Ir(piq)2(acac) = 98:2 (wt%) to form a light-emitting layer with a thickness of 22 nm. BCP:LiQ (1:1 (wt%)) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 29 nm. LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 0.9 nm. Mg:Ag (1:9) was vacuum-deposited on the electron injection layer as a cathode with a thickness of 14 nm. Finally, CP-1 was vacuum-deposited on the cathode as a capping layer with a thickness of 73 nm.

[0274] Examples 22-40: Fabrication of organic electroluminescent devices 22-40

[0275] In Example 21, compound 11 in the second hole transport layer was replaced with compounds 19, 54, 60, 141, 161, 164, 169, 206, 233, 257, 267, 273, 314, 333, 360, 419, 460, 463, and 474, respectively. The other steps were the same, and organic electroluminescent devices 22-40 were obtained.

[0276] Comparative Examples 3-4: Fabrication of Comparative Organic Electroluminescent Devices 3-4

[0277] By replacing compound 11 in the second hole transport layer of Example 21 with R-3 and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 3-4 were obtained.

[0278]

[0279] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 21-40 and Comparative Examples 3-4 of this invention are shown in Table 2.

[0280] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0281]

[0282]

[0283] As can be seen from Table 2, the organic electroluminescent device containing the triarylamine compound of Formula 1 of the present invention in the second hole transport layer has a lower driving voltage, higher luminous efficiency and longer lifespan compared with the comparative device.

[0284] Example 41: Fabrication of Organic Electroluminescent Device 41

[0285] HAT-CN was vacuum-deposited on the ITO anode as a hole injection layer with a thickness of 12 nm; NPB was vacuum-deposited on the hole injection layer as a first hole transport layer with a thickness of 70 nm; HT-2 was vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 40 nm; Compound 11 of the present invention was vacuum-deposited on the second hole transport layer as a third hole transport layer with a thickness of 35 nm; CBP, the host material, and GD-1, the dopant material, were vacuum-deposited on the third hole transport layer in a ratio of CBP:GD-1 = 92:8 (wt%) to form a light-emitting layer with a thickness of 20 nm; BCP:LiQ = 1:1 (wt%) was vacuum-deposited on the light-emitting layer as an electron transport layer with a thickness of 28 nm; LiF was vacuum-deposited on the electron transport layer as an electron injection layer with a thickness of 1.0 nm; and Al was vacuum-deposited on the electron injection layer as a cathode with a thickness of 110 nm.

[0286] Examples 42-60: Fabrication of Organic Electroluminescent Devices 42-60

[0287] In Example 41, compound 11 in the third hole transport layer was replaced with compounds 19, 40, 54, 60, 161, 164, 169, 206, 233, 267, 314, 333, 360, 378, 419, 460, 463, 474, and 505, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 42-60.

[0288] Comparative Examples 5-6: Fabrication of Comparative Organic Electroluminescent Devices 5-6

[0289] By replacing compound 11 in the third hole transport layer of Example 41 with R-4 and R-5 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 5-6 were obtained.

[0290]

[0291] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 41-60 and Comparative Examples 5-6 of this invention are shown in Table 3.

[0292] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0293]

[0294]

[0295] As can be seen from Table 3, compared with comparative devices 5-6, the organic electroluminescent devices containing the triarylamine compounds of Formula 1 of this invention have lower driving voltage, higher luminous efficiency, and superior device performance.

[0296] 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, The triarylamine compound is selected from one of formulas 1-1 to 1-3. Wherein, R1, R2, R3, and R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, substituted or unsubstituted phenyl, or two adjacent R1, two R2, two R3, and two R4 are bonded to each other to form a substituted or unsubstituted benzene ring; The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3 or 4; the n4 is selected from 0, 1, 2, 3 or 4. The R5, R6, R7, and R8 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or two adjacent R5, two R6, two R7, and two R8 are bonded to each other to form a substituted or unsubstituted benzene ring; The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3, 4 or 5. The Selected from one of the following groups, s1 is selected from 0, 1, or 2; s2 is selected from 0 or 1; r1 is selected from 0, 1, 2, 3 or 4; r2 is selected from 0, 1, 2 or 3; r5 is selected from 0, 1, 2, 3, 4, 5 or 6; r7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; The Y is selected from O and S; The R t It is selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl. The R d It is selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridine; The L0, L1, and L2 that are the same or different are selected from single bonds, or one or a combination of the following groups. The R f The same or different are selected from one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, trimethylsilyl, and triethylsilyl; t1 is selected from 0, 1, 2, 3 or 4; t2 is selected from 0, 1, 2, 3, 4, 5 or 6; The substituents represented by "substituted or unsubstituted" are selected from the groups, including deuterium, cyano, halogen, methyl, ethyl, propyl, and butyl.

2. The triarylamine compound according to claim 1, characterized in that, The triarylamine compound is selected from one of Formula 1-1 to Formula 1-2. 。 3. The triarylamine compound according to claim 1, characterized in that, The Selected from one of the following groups, The same or different R1, R2, R3, and R4 are selected from hydrogen, deuterium, methyl, ethyl, propyl, and butyl. The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2, 3 or 4; the n4 is selected from 0, 1, 2, 3 or 4; the n5 is selected from 0, 1, 2 or 3; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6; and the n7 is selected from 0, 1, 2, 3, 4 or 5.

4. The triarylamine compound according to claim 1, characterized in that, The Selected from one of the following groups, The Selected from one of the following groups, The Selected from one of the following groups, The same or different R5, R6, R7, and R8 are selected from hydrogen, deuterium, methyl, ethyl, propyl, and butyl. The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3 or 4; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3, 4 or 5; the m5 is selected from 0, 1, 2, 3, 4, 5 or 6; the m6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the m7 is selected from 0, 1, 2 or 3.

5. The triarylamine compound according to claim 1, characterized in that, The Selected from one of the following groups, The R t Selected from one of hydrogen, deuterium, methyl, ethyl, propyl, and butyl; The R d It is selected from one of hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted pyridine.

6. The triarylamine compound according to claim 1, characterized in that, The L0, L1, and L2 that are the same or different are selected from single bonds, or one or a combination of the following groups. The R f The same or different ones are selected from hydrogen and deuterium.

7. A triarylamine compound, characterized in that, The triarylamine compounds are selected from any one of the structures shown below. 。 8. An organic electroluminescent device, characterized in that, The organic electroluminescent device contains a triarylamine compound as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode, and the organic layer contains a triarylamine compound as described in any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the cathode and the anode, and the organic layer includes a hole transport region containing a triarylamine compound as described in any one of claims 1 to 7.

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