Arylamine derivative and organic electroluminescent device thereof

Abstract

The application provides an arylamine derivative and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The arylamine derivative has excellent hole transport capacity, when being applied to a hole transport region in an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved, and the arylamine derivative has a suitable HOMO energy level, can be better matched with adjacent functional layers, and when being applied to a P-type charge generation layer of the organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved, which shows that the arylamine derivative has excellent charge generation capacity and stability, can be widely applied to panel display, lighting sources and other fields, and has good application prospect.

Description

Technical Field

[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to an aromatic amine derivative and its organic electroluminescent device. Background Technology

[0002] Organic light-emitting diodes (OLEDs), as a next-generation display technology, have gained increasing popularity among consumers due to their advantages such as wide viewing angles, low power consumption, and fast response times. After decades of development, OLED technology has been successfully applied to electronic devices such as mobile phone screens, televisions, and wearable devices. Although significant progress and applications have been made in related technologies, improving device lifespan and reducing efficiency roll-off remain hot research topics in academia and industry.

[0003] The classic OLED device structure mainly includes an anode, cathode, hole transport layer (HTL), electron transport layer (ETL), and emission layer (EML). The commonly used anode is transparent indium tin oxide (ITO), the cathode is low-power aluminum, and the HTL, ETL, and EML are all organic semiconductor materials. To achieve better device performance, organic semiconductor materials such as electron injection layer (EIL), hole injection layer (HIL), electron blocking layer (EBL), and hole blocking layer (HBL) are also introduced into the device structure. The working principle of an OLED device is as follows: When an external voltage is applied to the device, holes and electrons are injected from the anode and cathode, respectively. Under the influence of the external electric field, holes and electrons migrate through the transport layers to the cathode and anode, respectively. After merging in the emission layer, they recombine to form excitons. The excitons decay back to the ground state through a series of photophysical processes and emit photons, producing light emission.

[0004] Hole transport materials, as an important component of general-purpose OLED materials, possess excellent properties that can improve the hole transport rate in devices, achieving a balance between hole and electron transport rates, and enabling effective collision between holes and electrons in the emissive layer. Furthermore, high-performance hole transport materials can lower the energy barrier during hole injection, improving hole injection efficiency and thus enhancing device efficiency, lifetime, and brightness. Simultaneously, to address lifetime and efficiency issues, multilayer hole transport layers with appropriate energy levels are typically added between the hole transport layer and the emissive layer. This reduces the potential barrier between the hole transport layer and the emissive layer, lowers the driving voltage of organic light-emitting devices, and further increases hole utilization, thereby improving luminous efficiency and lifetime. However, most current hole transport materials suffer from low hole mobility, poor film formation, and poor thermal stability.

[0005] To further improve the current efficiency and extend the lifespan of OLEDs, multilayer organic light-emitting diodes (OLEDs) that electrically connect multiple light-emitting units through a charge generation layer have become a research hotspot. Under an applied electric field, electrons and holes generated by the charge generation layer are injected into adjacent light-emitting units and recombine within the units to form excitons that emit light. Therefore, the selection and design of the charge generation layer material are key factors affecting the luminous efficiency and lifespan of multilayer organic light-emitting diodes.

[0006] To address the aforementioned issues, the development of hole transport materials with high hole mobility and suitable HOMO energy levels, as well as materials that can be used in charge generation layers, has become the focus of current research. Summary of the Invention

[0007] The purpose of this invention is to provide an aromatic amine derivative and its organic electroluminescent device. When the aromatic amine derivative provided by this invention is applied to the hole transport layer or P-type charge generation layer of an organic electroluminescent device, a high-efficiency and long-lifetime organic electroluminescent device can be developed, solving the problems of low luminous efficiency and short lifespan in existing organic electroluminescent devices. The aromatic amine derivative provided by this invention has the general formula shown in Formula 1.

[0008]

[0009] Wherein, R1 is selected from any one of substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C15 alicyclic groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C2-C30 heteroaryl groups; and R2 is selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0010] R5 and R6 are independently selected from substituted or unsubstituted C1-C15 alkyl groups and substituted or unsubstituted silyl groups;

[0011] Each time R3, R4, R7, and R8 appear, they are selected, either identically or differently, from any of the following: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclic, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl; or adjacent R3s, R4s, R7s, and R8s are interconnected to form substituted or unsubstituted rings; a is selected from 1, 2, 3, or 4; b is selected from 1, 2, 3, or 4; c is selected from 1, 2, 3, or 4; d is selected from 1, 2, 3, or 4.

[0012] X is selected from O atoms, N(R) atoms. d );

[0013] Each time v appears, it is selected from N or CH, either the same or different; the v at the bonding site is selected from C;

[0014] The R d It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclic group, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl.

[0015] The R a R b R c Each time it appears, it is selected from hydrogen or deuterium, either the same or different; the e is selected from 1, 2 or 3;

[0016] The L1 and L2 are independently selected from single bonds or groups as shown below:

[0017]

[0018]

[0019] Each time X1 appears, it is selected from O atoms, S atoms, C(R) atoms, either the same or different. j R k ), N(R p );

[0020] Each time X2 appears, it is selected from O atoms, S atoms, N(R) atoms, either the same or different. q );

[0021] Each time x appears, it is selected from N or CH, either the same or different; x at the bonding site is selected from C;

[0022] Each time n appears, it is selected from 1, 2, 3, 4 or 5, either the same or different.

[0023] Each time ring A appears, it is selected from substituted or unsubstituted C3 to C10 alicyclic groups, either the same or different.

[0024] The R 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl.

[0025] The R j R k Each time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0026] The R p R q Each time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0027] Each time g1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time g2 appears, it is selected from 1, 2 or 3, either the same or different; each time g3 appears, it is selected from 1 or 2, either the same or different.

[0028] The L3 is selected from single bonds or groups as shown below:

[0029]

[0030] Each time Y1 appears, it is selected from O atoms, S atoms, C(R) atoms, either the same or different. m R n ), N(R t );

[0031] Each time Y2 appears, it is selected from O atoms, S atoms, N(R) atoms, either the same or different. s );

[0032] Each time z appears, it is selected from N or CH, either the same or different; the z at the bonding site is selected from C;

[0033] Each time m appears, it is selected from 1, 2, 3, 4 or 5, either the same or different.

[0034] Each time ring B appears, it is selected from substituted or unsubstituted C3-C7 alicyclic groups, either the same or different.

[0035] The R 12 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl.

[0036] The R m R n Each time it appears, it is selected, either identically or differently, from any of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl groups; or the R... m and R n They connect to form substituted or unsubstituted rings;

[0037] The R t R sEach time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0038] Each time h1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time h2 appears, it is selected from 1, 2 or 3, either the same or different; each time h3 appears, it is selected from 1 or 2, either the same or different.

[0039] The present invention also provides an organic electroluminescent device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer located between the first electrode and the second electrode or outside one or more of the first electrode and the second electrode, wherein the organic layer contains any one or a combination of at least two of the aromatic amine derivatives described in the present invention.

[0040] Beneficial effects:

[0041] The aromatic amine derivatives disclosed in this invention possess excellent hole transport capabilities, thus they can be used as hole transport layer materials in organic electroluminescent devices. Compared with conventional materials, this enables the fabrication of organic electroluminescent devices with high luminous efficiency and long lifespan. Furthermore, the aromatic amine derivatives of this invention exhibit good charge generation capabilities and stability. When used as p-type materials for the charge generation layer, they are beneficial for improving charge generation efficiency and device stability, thereby obtaining high-performance multilayer organic electroluminescent devices. Detailed Implementation

[0042] 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.

[0043] In the compounds of this invention, any atom not specified as a particular isotope contains any stable isotope of that atom, and contains atoms at both their natural and non-natural isotopic abundances. Taking hydrogen as an example, each hydrogen atom in all naturally occurring compounds contains about 0.0156 atomic percent deuterium.

[0044] In this invention, the use of "H" and "hydrogen atom" refers to the presence of no more than the natural abundance of deuterium or tritium atoms in the chemical structure, for example, no more than 0.0156 atomic% of deuterium. "D" and "deuterium atom" refer to a deuterium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95 atomic% of deuterium. "T" and "tritium atom" refer to a tritium abundance greater than the natural abundance, for example, any value exceeding 0.1 atomic%, 1 atomic%, or 10 atomic%, such as approximately 95% of tritium. In this invention, the omission of undrawn hydrogen atoms signifies "H" or "hydrogen atom".

[0045] Examples of halogens described in this invention may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0046] In this invention, "C1-C15" in "substituted or unsubstituted C1-C15 alkyl groups" refers to the number of carbon atoms in the unsubstituted alkyl group, excluding the number of carbon atoms in the substituents. Similarly, "C6-C30" in "substituted or unsubstituted C6-C30 aryl groups" refers to the number of carbon atoms in the unsubstituted aryl group, excluding the number of carbon atoms in the substituents. And so on.

[0047] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has 1 to 15 carbon atoms, preferably 1 to 10. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0048] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0049] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R W )3 groups, wherein each R W 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 WThe 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. 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... W The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. The term "alkylsilyl" refers to at least one substituent R of a silyl (-SiH3) group. W It is an alkyl group, and the preferred alkylsilyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the "arylsilyl" refers to at least one substituent R of the alkyl (-SiH3) group. W It is an aryl group, and preferred arylsilyl groups include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are not limited to these.

[0050] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, phenanthrene, triphenylene, anthracene, pyrene, fluorenyl, spirodifluorenyl, spiroanthracenefluorenyl, benzo[a]fluorenyl, benzo[a]spirodifluorenyl, etc.

[0051] The alicyclic group described in this invention refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage-like structure, such as adamantane, norbornane, camphene, etc., but are not limited thereto.

[0052] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for monovalent groups formed by fusion of an alicyclic and an aromatic ring and the removal of one hydrogen atom. Examples of fused alicyclic and aromatic ring groups may include dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclobutenyl, benzocycloheptane, benzocycloheptenyl, etc., but are not limited thereto. The alicyclic ring has 3 to 15 carbon atoms, preferably 3 to 10. The aromatic ring has 6 to 30 carbon atoms, preferably 6 to 18, and even more preferably 6 to 12.

[0053] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably deuterium, halogen, cyano, nitro, C1-C12 alkyl, C3- C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, substituted or unsubstituted silyl, wherein, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclopropane Butyl, ethyl-substituted cyclobutyl, deuterated cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrole The following groups are used: yl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophene, trimethylsilyl, triphenylsilyl, where, when substituted by multiple substituents, the multiple substituents may be the same or different from each other.

[0054] 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 or Can represent And so on.

[0055] 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.

[0056] For example, Can represent Can represent Can represent And so on.

[0057] In this invention, "adjacent groups can connect with each other to form substituted or unsubstituted rings" refers to the formation of substituted or unsubstituted hydrocarbon rings or substituted or unsubstituted heterocycles by the combination of adjacent groups and optional aromatization. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Examples are shown below:

[0058]

[0059] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but is not limited thereto.

[0060] This invention provides an aromatic amine derivative having the general formula shown in structural formula 1.

[0061]

[0062] Wherein, R1 is selected from any one of substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C15 alicyclic groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C2-C30 heteroaryl groups; and R2 is selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C2-C30 heteroaryl groups.

[0063] R5 and R6 are independently selected from substituted or unsubstituted C1-C15 alkyl groups and substituted or unsubstituted silyl groups;

[0064] Each time R3, R4, R7, and R8 appear, they are selected, either identically or differently, from any of the following: hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclic, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl; or adjacent R3s, R4s, R7s, and R8s are interconnected to form substituted or unsubstituted rings; a is selected from 1, 2, 3, or 4; b is selected from 1, 2, 3, or 4; c is selected from 1, 2, 3, or 4; d is selected from 1, 2, 3, or 4.

[0065] X is selected from O atoms, N(R) atoms. d );

[0066] Each time v appears, it is selected from N or CH, either the same or different; the v at the bonding site is selected from C;

[0067] The R d It is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C15 alicyclic group, fused cycloalcohol of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl.

[0068] The R a R b R c Each time it appears, it is selected from hydrogen or deuterium, either the same or different; the e is selected from 1, 2 or 3;

[0069] The L1 and L2 are independently selected from single bonds or groups as shown below:

[0070]

[0071] Each time X1 appears, it is selected from O atoms, S atoms, C(R) atoms, either the same or different. j R k ), N(R p );

[0072] Each time X2 appears, it is selected from O atoms, S atoms, N(R) atoms, either the same or different. q );

[0073] Each time x appears, it is selected from N or CH, either the same or different; x at the bonding site is selected from C;

[0074] Each time n appears, it is selected from 1, 2, 3, 4 or 5, either the same or different.

[0075] Each time ring A appears, it is selected from substituted or unsubstituted C3 to C10 alicyclic groups, either the same or different.

[0076] The R 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl.

[0077] The R j R k Each time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0078] The R p R q Each time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0079] Each time g1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time g2 appears, it is selected from 1, 2 or 3, either the same or different; each time g3 appears, it is selected from 1 or 2, either the same or different.

[0080] The L3 is selected from single bonds or groups as shown below:

[0081]

[0082] Each time Y1 appears, it is selected from O atoms, S atoms, C(R) atoms, either the same or different. m R n ), N(R t );

[0083] Each time Y2 appears, it is selected from O atoms, S atoms, N(R) atoms, either the same or different. s );

[0084] Each time z appears, it is selected from N or CH, either the same or different; the z at the bonding site is selected from C;

[0085] Each time m appears, it is selected from 1, 2, 3, 4 or 5, either the same or different.

[0086] Each time ring B appears, it is selected from substituted or unsubstituted C3-C7 alicyclic groups, either the same or different.

[0087] The R 12 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl.

[0088] The R m R n Each time it appears, it is selected, either identically or differently, from any of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and substituted or unsubstituted C2-C30 heteroaryl groups; or the R... m and R n They connect to form substituted or unsubstituted rings;

[0089] The R t R sEach time it appears, it is selected from any one of the following, either identically or differently: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, or substituted or unsubstituted C2-C30 heteroaryl.

[0090] Each time h1 appears, it is selected from 1, 2, 3 or 4, either the same or different; each time h2 appears, it is selected from 1, 2 or 3, either the same or different; each time h3 appears, it is selected from 1 or 2, either the same or different.

[0091] Preferably, in Formula 1 Selected from any one of the following groups:

[0092]

[0093]

[0094] Each time R3 and R4 appear, they are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, indene, tetrahydronaphthyl, fluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, or any combination thereof; or adjacent R3s or R4s may be interconnected to form substituted or unsubstituted rings;

[0095] The R9, R 10 Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, indene, tetrahydronaphthyl, fluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, or any combination thereof; or two adjacent R9s may be interconnected to form substituted or unsubstituted rings;

[0096] Each time f1 appears, it is selected from 1, 2, 3, 4, or 5, either the same or different. Each time f2 appears, it is selected from 1, 2, 3, or 4, either the same or different. Each time f3 appears, it is selected from 1, 2, 3, 4, 5, 6, or 7, either the same or different. Each time f4 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9, either the same or different. Each time f5 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time f6 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. The numbers are selected differently from 1, 2, 3, 4, 5, 6, 7, or 8; each time f7 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, the same or different. Each time f8 appears, it is selected from 1, 2, or 3, the same or different. Each time f9 appears, it is selected from 1 or 2, the same or different. Each time a1 appears, it is selected from 1, 2, 3, 4, 5, or 6, the same or different. Each time b1 appears, it is selected from 1, 2, 3, 4, 5, or 6, the same or different.

[0097] Preferably, in Formula 1 Selected from any one of the following groups:

[0098]

[0099] Each time R7 and R8 appear, they are selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, indene, tetrahydronaphthyl, fluorenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, or any combination thereof; or adjacent R7s or R8s may be interconnected to form substituted or unsubstituted rings;

[0100] The R g The following groups are selected from hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, or any combination thereof;

[0101] Each time c1 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time c2 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time c3 appears, it is selected from 1, 2, 3, 4, 5, 6, or 7, either the same or different. Each time c4 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different. Each time d1 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time d2 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different.

[0102] Preferably, in Formula 1 Selected from any one of the following groups:

[0103]

[0104] The R d The group is selected from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, or any combination thereof.

[0105] Preferably, L1 and L2 are independently selected from single bonds or any one of the following groups:

[0106]

[0107]

[0108]

[0109] The R 11 Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0110] The R 13Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0111] The R p R q Each time it appears, it is selected from the following groups, either substituted or unsubstituted, in the same or different manner: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0112] Each time g1 appears, it is selected from 1, 2, 3, or 4, either the same or different. Each time g2 appears, it is selected from 1, 2, or 3, either the same or different. Each time g3 appears, it is selected from 1 or 2, either the same or different. Each time g4 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time g5 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different.

[0113] More preferably, L1 and L2 are independently selected from single bonds or any one of the following groups:

[0114]

[0115] Preferably, L3 is selected from single bonds or any one of the following groups:

[0116]

[0117]

[0118] The R 12Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0119] The R 14 Each time it appears, it is selected, either identically or differently, from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0120] The R s R t Each time it appears, it is selected from the following groups, either substituted or unsubstituted, in the same or different manner: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, indene, tetrahydronaphthyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, or any combination thereof;

[0121] Each time h1 appears, it is selected from 1, 2, 3, or 4, either the same or different. Each time h2 appears, it is selected from 1, 2, or 3, either the same or different. Each time h3 appears, it is selected from 1 or 2, either the same or different. Each time h4 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time h5 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time h6 appears, it is selected from 1, 2, 3, 4, or 5, either the same or different. Each time h7 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, either the same or different.

[0122] More preferably, L3 is selected from a single bond or any one of the following groups:

[0123]

[0124]

[0125] Most preferably, the aromatic amine derivative represented by Formula 1 is selected from any one of the following chemical structures:

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144] The above lists some specific chemical structures of the aromatic amine derivatives of structural formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any product based on the aromatic amine derivative of structural formula 1 with substituents as defined above should be included.

[0145] Furthermore, the present invention also provides an organic electroluminescent device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic layer located between the first electrode and the second electrode or outside one or more of the first electrode and the second electrode, wherein the organic layer contains any one or a combination of at least two of the aromatic amine derivatives described in the present invention.

[0146] Preferably, the organic layer includes a hole transport region, a light-emitting layer, an electron transport region, and a capping layer, wherein at least one layer of the hole transport region contains any one or a combination of at least two of the aromatic amine derivatives described in this invention.

[0147] Preferably, the organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region, and a capping layer. Each light-emitting layer has an N-type charge generation layer and a P-type charge generation layer in the middle. The P-type charge generation layer contains any one or a combination of at least two of the aromatic amine derivatives described in this invention.

[0148] Preferably, the first electrode is the anode and the second electrode is the cathode, or alternatively, the first electrode is the cathode and the second electrode is the anode.

[0149] Preferably, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer. The hole injection layer is located between the anode and the cathode, the hole transport layer is located between the hole injection layer and the cathode, and the electron blocking layer is located between the hole transport layer and the cathode. At least one of the hole injection layer, the hole transport layer, and the electron blocking layer contains the aromatic amine derivative described in this invention.

[0150] Preferably, the hole transport region includes a hole transport layer, and the hole transport layer contains the aromatic amine derivative described in this invention.

[0151] 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 cathode, and the first hole transport layer containing the aromatic amine derivative described in this invention.

[0152] 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 cathode, and the second hole transport layer containing the aromatic amine derivative described in this invention.

[0153] 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 cathode, and the first hole transport layer and the second hole transport layer containing the aromatic amine derivative described in this invention.

[0154] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, and the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains the aromatic amine derivative described in this invention.

[0155] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the first hole transport layer contains the aromatic amine derivative described in this invention.

[0156] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the second hole transport layer contains the aromatic amine derivative described in this invention.

[0157] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and the third hole transport layer contains the aromatic amine derivative described in this invention.

[0158] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device or a multilayer organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the multilayer organic electroluminescent device is an organic electroluminescent device formed by connecting N (N≥2) independent light-emitting units in series through a charge generation layer.

[0159] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, wherein an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0160] Preferably, the organic electroluminescent device of the present invention is a stacked organic electroluminescent device, wherein a first light-emitting unit emitting light of a first color, an Nth light-emitting unit emitting light of an Nth color, and a charge generation layer uniformly controlling the charge between the first light-emitting unit and the Nth light-emitting unit are formed between the anode and the cathode, and an N-type charge generation layer and a P-type charge generation layer are included between adjacent light-emitting units.

[0161] Preferably, the P-type charge generation layer contains the aromatic amine derivative of the present invention, or the P-type charge generation layer can be formed by doping the aromatic amine derivative of the present invention with other materials.

[0162] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0163] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below:

[0164] The anode of this invention preferably uses metals, alloys, conductive compounds, and mixtures thereof that have a high work function (specifically, 4.0 eV or more). The materials used for the anode in this invention can include: metals or their alloys, metal oxides, multilayer materials, conductive polymers, combinations of metals and oxides, etc., for example, nickel (Ni), platinum (Pt), vanadium (V), silver (Ag), gold (Au), zinc oxide (ZnO), indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (In₂O₃), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polypyrrole, polyaniline, zinc oxide:aluminum (ZnO:Al), etc., but are not limited thereto.

[0165] The hole injection material described in this invention is preferably a material capable of reducing the interfacial barrier between the anode and the hole transport layer. Materials include, as described below, polycyano conjugated organic compounds, axial alkene compounds, phthalocyanine metal complexes, aromatic amine derivatives, polymers, etc. Specific examples may include metalloporphyrins, oligothiophenes, aryl amine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene, but are not limited thereto, and may also include other compounds capable of p-doping.

[0166] The hole transport material of this invention is preferably a material capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer, and possesses high hole mobility and good stability. The hole transport material of this invention is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer, and can be a single-layer structure or a multi-layer structure. For example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc., can be used as the hole transport layer material. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-( Spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 9,10-bis(2-naphthyl)anthracene (DNA), 9,10-diphenylanthracene (DPAnth), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), and aromatic amine derivatives of Formula 1 of the present invention, but not limited thereto. Aromatic amine derivatives of Formula 1 of the present invention are preferred.

[0167] The electron blocking layer of this invention preferably uses a material whose absolute value of the difference between the HOMO value of the electron blocking layer and that of the hole transport layer is greater than or equal to 0.07 eV and less than or equal to 0.35 eV. Specific examples may include materials such as aromatic amine derivatives, spirofluorene derivatives, and furan derivatives, such as TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1' The following are examples of aromatic amine derivatives, including but not limited to: [[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, and the aromatic amine derivatives described in this invention. Preferably, the aromatic amine derivatives shown in Formula 1 of this invention are preferred.

[0168] The light-emitting layer described in this invention may contain only the guest material, or it may be in the form of the guest material being dispersed in the host material, wherein the host material may be composed of one or more materials.

[0169] As the main material of the light-emitting layer of the present invention, it may include fused aromatic ring derivatives, heterocyclic compounds, etc., such as 9,10-bis(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tris(pyrene-1-yl)benzene (TPB3), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 14,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), 9-[4-(10-phenyl-9-yl) [-anthrayl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB), etc., but not limited to these.

[0170] As the guest material of the luminescent layer in this invention, it may include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as 4,4'-bis(4-(9H-carbazole-9-yl)styryl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenyltetraphenyl (Rubrene), coumarin 545T (C-525T)tris(2-phenyl-3-methylpyridine)iridium (Ir(3mppy) 3), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium(III)(Ir(npy)2acac), tri(2-phenylpyridine)iridium(III)(Ir(ppy)3), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac), etc., but not limited to these.

[0171] The hole-blocking layer material described in this invention needs to have good hole-blocking ability in order to block holes within the light-emitting layer. Materials such as imidazole derivatives, phenanthroline derivatives, metal complexes, and triazine derivatives are examples. Specific examples may include, but are not limited to, 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphth-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc.

[0172] The electron transport layer material described in this invention preferably possesses good electron transport capability and good stability. It can be a single-layer structure or a multi-layer structure. Materials such as those described below include imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, quinoline derivatives, oxadiazole derivatives, triazole derivatives, and metal complexes. Specific examples may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazolium, 2-(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 3,3'-[5'-[3-(3- [Pyridyl)phenyl](TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene, 2-(3-(phenanthrene-9-yl)-5-(pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 1,3,5-tris(4-(pyridin-4-yl)quinoline-2-yl)phenyl (TPyQB), 2,5-di- (4-Naphthyl)-1,3,4-oxadiazole (BND), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), lithium 8-hydroxyquinolineate (LiQ), tris(8-hydroxyquinoline)aluminum(III) (abbreviated: Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated: BeBq2), phenanthroline (abbreviated: BPhen), copper bath (abbreviated: BCP), poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py), etc., but not limited to these.

[0173] The electron injection layer material described in this invention is preferably a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. Alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple such compounds can be used in combination.

[0174] The cathode of this invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, 3.8 eV or less). The materials used for the cathode in this invention may include: metals or their alloys, multilayer materials, etc., such as silver (Ag), aluminum (Al), magnesium (Mg), tin (Sb), magnesium silver (Mg:Ag), calcium / magnesium (Ca / Mg), etc., but are not limited thereto.

[0175] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Specific examples may include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, aluminum(III)tris(8-hydroxyquinoline) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (CBP), etc., but are not limited to these.

[0176] The N-type charge-generating material described in this invention can be selected from one of the following materials or combinations thereof: tri-(8-hydroxyquinoline)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinoline (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-phenololine)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( BCP, 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternating-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), etc., but not limited to these. In addition, auxiliary N-type charge-generating materials may also be included. For example, the auxiliary N-type charge generation material can be an alkali metal, such as Li, Cs, K, Rb, Na or Fr, but not limited to these, or an alkaline earth metal, such as Be, Mg, Ca, Sr, Ba or Ra, but not limited to these.

[0177] The P-type charge-generating material of this invention may comprise one of the following materials or combinations thereof: 4,4',4”-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4”-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4”-tris(N-(naphthyl-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4”-tris(N-(naphthyl-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl)-1,1'- Biphenyl-4,4”-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylhexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrene sulfonate (PEDOT / PSS), and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine, aromatic amine derivatives described in this invention, etc., but not limited thereto, with the aromatic amine derivatives shown in Formula 1 of this invention being preferred.

[0178] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., can be used, but are not limited to these. There are no particular limitations on the film thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates. Therefore, it is usually 5nm to 10μm, more preferably 10nm to 0.2μm.

[0179] The organic electroluminescent device of the present invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, televisions, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, lighting equipment, etc.

[0180] Synthesis Examples

[0181] 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.

[0182] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0183] There are no particular limitations on the preparation method of the aromatic amine derivative of structural 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. For example, the aromatic amine derivative of structural formula 1 of the present invention can be prepared by the following synthetic route.

[0184] Synthesis Route 1:

[0185]

[0186] Synthesis Route 2:

[0187]

[0188] X1 and X2 are halogen atoms, for example, they may be the same or different halogen atoms selected from the following: I, Br, Cl.

[0189] The R1~R8, L1~L3, R a ~Rc and a~e are as described in this invention.

[0190] Synthesis Example 1: Preparation of Intermediate C-91

[0191]

[0192] Under argon protection, c-32 (11.03 g, 56.00 mmol), d-91 (8.76 g, 56.00 mmol), potassium carbonate (11.61 g, 84.00 mmol), Pd(PPh3)4 (0.77 g, 0.67 mmol), and 280 mL of a toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried with anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give intermediate C-91 (10.12 g, yield 79%); HPLC purity ≥ 99.80%. Mass spectrometry m / z: 228.0358 (theoretical value: 228.0342).

[0193] Other intermediates required for the present invention were synthesized using the above synthesis method. The relevant raw materials are shown in Table 101.

[0194] Table 101:

[0195]

[0196]

[0197] Synthesis Example 2: Preparation of Compound 3

[0198]

[0199] Preparation of intermediate I-3:

[0200] Under argon protection, a-3 (12.56 g, 60.00 mmol), b-3 (23.84 g, 60.00 mmol), Pd(OAc)2 (0.13 g, 0.60 mmol), sodium tert-butoxide (11.53 g, 120.00 mmol), tri-tert-butylphosphine (1.2 mL, 0.5 M in toluene solution), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and dichloromethane and distilled water were added to the reaction solution. The mixture was stirred and extracted by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed. The mixture was recrystallized from toluene:ethanol = 10:1 to give intermediate I-3 (24.60 g, yield 78%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 525.2440 (theoretical value: 525.2457). Preparation of compound 3:

[0201] Under argon protection, I-3 (21.03 g, 40.00 mmol), c-3 (7.88 g, 40.00 mmol), Pd2(dba)3 (0.46 g, 0.40 mmol), sodium tert-butoxide (7.69 g, 80.00 mmol), BINAP (0.50 g, 0.80 mmol), and 200 mL of toluene were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with diatomaceous earth, concentrated, recrystallized with toluene, filtered under vacuum, and washed with toluene to obtain the recrystallized solid, yielding compound 3 (19.51 g, yield 76%). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrometry m / z: 641.2729 (theoretical value: 641.2719). Theoretical elemental content (%) C 48 H 35 NO: C, 89.83; H, 5.50; N, 2.18. Measured elemental content (%): C, 89.86; H, 5.48; N, 2.15.

[0202] Synthesis Example 3: Preparation of Compound 32

[0203]

[0204] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-32, and c-3 was replaced with an equimolar amount of c-32, yielding compound 32 (20.10 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 669.3020 (theoretical value: 669.3032). Theoretical elemental content (%) C 50 H 39 NO: C, 89.65; H, 5.87; N, 2.09. Measured elemental content (%): C, 89.63; H, 5.85; N, 2.12.

[0205] Synthesis Example 4: Preparation of Compound 41

[0206]

[0207] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-41, and c-3 was replaced with an equimolar amount of c-41, yielding compound 41 (21.72 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 753.3985 (theoretical value: 753.3971). Theoretical elemental content (%) C 56 H 51 NO: C, 89.20; H, 6.82; N, 1.86. Measured elemental content (%): C, 89.17; H, 6.84; N, 1.88.

[0208] Synthesis Example 5: Preparation of Compound 44

[0209]

[0210] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-44, and c-3 was replaced with an equimolar amount of c-32, yielding compound 44 (20.85 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 713.3125 (theoretical value: 713.3114). Theoretical elemental content (%) C 51 H 43 NOSi: C, 85.79; H, 6.07; N, 1.96. Measured elemental content (%): C, 85.81; H, 6.04; N, 1.95.

[0211] Synthesis Example 6: Preparation of Compound 48

[0212]

[0213] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-48, and c-3 was replaced with an equimolar amount of c-32, yielding compound 48 (20.91 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 717.3018 (theoretical value: 717.3032). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Measured elemental content (%): C, 90.37; H, 5.46; N, 1.97.

[0214] Synthesis Example 7: Preparation of Compound 58

[0215]

[0216] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-58, b-3 was replaced with an equimolar amount of b-58, and c-3 was replaced with an equimolar amount of c-32, yielding compound 58 (20.68 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 717.3016 (theoretical value: 717.3032). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Analyzed elemental composition (%): C, 90.37; H, 5.46; N, 1.97. Synthesis Example 8: Preparation of Compound 78

[0217]

[0218] Following the method of Example 2, c-3 was replaced with an equimolar amount of c-78 to obtain compound 78 (18.89 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 646.3047 (theoretical value: 646.3032). Theoretical elemental content (%) C 48 H 30 D5NO: C, 89.13; H, 6.23; N, 2.17. Measured elemental content (%): C, 89.16; H, 6.19; N, 2.15.

[0219] Synthesis Example 9: Preparation of Compound 84

[0220]

[0221] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-84, and c-3 was replaced with an equimolar amount of c-32, yielding compound 84 (19.93 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 691.2860 (theoretical value: 691.2875). Theoretical elemental content (%) C 52 H 37 NO: C, 90.27; H, 5.39; N, 2.02. Measured elemental content (%): C, 90.25; H, 5.41; N, 2.06.

[0222] Synthesis Example 10: Preparation of Compound 91

[0223]

[0224] Following the method of Example 2, c-3 was replaced with an equimolar amount of c-91 to obtain compound 91 (21.82 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 717.3049 (theoretical value: 717.3032). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Measured elemental content (%): C, 90.32; H, 5.46; N, 1.98.

[0225] Synthesis Example 11: Preparation of Compound 94

[0226]

[0227] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-94, and c-3 was replaced with an equimolar amount of C-94, yielding compound 94 (21.00 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 717.3048 (theoretical value: 717.3032). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Measured elemental content (%): C, 90.31; H, 5.47; N, 1.97.

[0228] Synthesis Example 12: Preparation of Compound 95

[0229]

[0230] Following the method of Example 2, c-3 was replaced with an equimolar amount of C-95 to obtain compound 95 (20.10 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 717.3046 (theoretical value: 717.3032). Theoretical elemental content (%) C54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Measured elemental content (%): C, 90.32; H, 5.45; N, 1.94.

[0231] Synthesis Example 13: Preparation of Compound 99

[0232]

[0233] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-99, b-3 with an equimolar amount of b-99, and c-3 with an equimolar amount of C-99, yielding compound 99 (21.91 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 793.3335 (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, 90.74; H, 5.44; N, 1.79.

[0234] Synthesis Example 14: Preparation of Compound 109

[0235]

[0236] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-109, b-3 with an equimolar amount of b-109, and c-3 with an equimolar amount of C-109, yielding compound 109 (23.08 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 911.4141 (theoretical value: 911.4127). Theoretical elemental content (%) C 69 H 53 NO: C, 90.85; H, 5.86; N, 1.54. Measured elemental composition (%): C, 90.88; H, 5.83; N, 1.56. Synthesis Example 15: Preparation of Compound 122

[0237]

[0238] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-122, b-3 with an equimolar amount of b-122, and c-3 with an equimolar amount of C-122, yielding compound 122 (23.75 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 873.3902 (theoretical value: 873.3909). Theoretical elemental content (%) C 66 H 43D4NO: C, 90.69; H, 5.88; N, 1.60. Measured elemental content (%): C, 90.71; H, 5.90; N, 1.63.

[0239] Synthesis Example 16: Preparation of Compound 131

[0240]

[0241] Following the method of Example 2, c-3 was replaced with an equimolar amount of C-131 to obtain compound 131 (22.12 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 781.3355 (theoretical value: 781.3345). Theoretical elemental content (%) C 59 H 43 NO: C, 90.62; H, 5.54; N, 1.79. Measured elemental content (%): C, 90.65; H, 5.52; N, 1.81.

[0242] Synthesis Example 17: Preparation of Compound 142

[0243]

[0244] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-99, and c-3 was replaced with an equimolar amount of C-142, yielding compound 142 (21.22 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 757.3361 (theoretical value: 757.3345). Theoretical elemental content (%) C 57 H 43 NO: C, 90.32; H, 5.72; N, 1.85. Measured elemental content (%): C, 90.29; H, 5.74; N, 1.87.

[0245] Synthetic Example 18: Preparation of Compound 147

[0246]

[0247] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-147, and c-3 was replaced with an equimolar amount of C-147, yielding compound 147 (22.68 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 833.3645 (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, 5.65; N, 1.71.

[0248] Synthesis Example 19: Preparation of Compound 152

[0249]

[0250] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-94, b-3 with an equimolar amount of b-32, and c-3 with an equimolar amount of C-91, yielding compound 152 (20.80 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 745.3355 (theoretical value: 745.3345). Theoretical elemental content (%) C 56 H 43 NO: C, 90.17; H, 5.81; N, 1.88. Measured elemental content (%): C, 90.14; H, 5.79; N, 1.91.

[0251] Synthesis Example 20: Preparation of Compound 155

[0252]

[0253] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-155, and c-3 was replaced with an equimolar amount of C-91, yielding compound 155 (22.29 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 773.3649 (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, 6.15; N, 1.79.

[0254] Synthesis Example 21: Preparation of Compound 183

[0255]

[0256] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-183, and c-3 was replaced with an equimolar amount of C-91, yielding compound 183 (19.80 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 727.3645 (theoretical value: 727.3659). Theoretical elemental content (%) C 54 H 29 D 10 NO: C, 89.10; H, 6.78; N, 1.92. Measured elemental content (%): C, 89.08; H, 6.75; N, 1.93.

[0257] Synthesis Example 22: Preparation of Compound 184

[0258]

[0259] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-122, b-3 with an equimolar amount of b-184, and c-3 with an equimolar amount of C-91, yielding compound 184 (20.00 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 724.3458 (theoretical value: 724.3471). Theoretical elemental content (%) C 54 H 32 D7NO: C, 89.47; H, 6.39; N, 1.93. Measured elemental content (%): C, 89.45; H, 6.41; N, 1.90.

[0260] Synthesis Example 23: Preparation of Compound 198

[0261]

[0262] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-122, b-3 with an equimolar amount of b-198, and c-3 with an equimolar amount of C-198, yielding compound 198 (21.82 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 801.3971 (theoretical value: 801.3971). Theoretical elemental content (%) C 60 H 51 NO: C, 89.85; H, 6.41; N, 1.75. Analyzed elemental composition (%): C, 89.82; H, 6.39; N, 1.78. Synthesis Example 24: Preparation of Compound 199

[0263]

[0264] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-199, b-3 with an equimolar amount of b-199, and c-3 with an equimolar amount of C-199, yielding compound 199 (21.41 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 798.3669 (theoretical value: 798.3658). Theoretical elemental content (%) C 60 H 38 D5NO: C, 90.19; H, 6.05; N, 1.75. Measured elemental content (%): C, 90.21; H, 6.02; N, 1.73.

[0265] Synthesis Example 25: Preparation of Compound 200

[0266]

[0267] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-200, and c-3 was replaced with an equimolar amount of C-200, yielding compound 200 (21.00 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 771.3425 (theoretical value: 771.3439). Theoretical elemental content (%) C 58 H 37 D4NO: C, 90.24; H, 5.87; N, 1.81. Measured elemental content (%): C, 90.27; H, 5.90; N, 1.78.

[0268] Synthesis Example 26: Preparation of Compound 223

[0269]

[0270] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-223, b-3 with an equimolar amount of b-223, and c-3 with an equimolar amount of c-32, yielding compound 223 (23.60 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 893.3672 (theoretical value: 893.3658). Theoretical elemental content (%) C 68 H 47 NO: C, 91.35; H, 5.30; N, 1.57. Analyzed elemental composition (%): C, 91.32; H, 5.28; N, 1.55. Synthesis Example 27: Preparation of Compound 239

[0271]

[0272] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-122, b-3 with an equimolar amount of b-239, and c-3 with an equimolar amount of c-32, yielding compound 239 (18.22 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 669.3045 (theoretical value: 669.3032). Theoretical elemental content (%) C 50 H 39 NO: C, 89.65; H, 5.87; N, 2.09. Analyzed elemental composition (%): C, 89.66; H, 5.84; N, 2.05. Synthesis Example 28: Preparation of Compound 245

[0273]

[0274] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-245, b-3 with an equimolar amount of b-245, and c-3 with an equimolar amount of C-91, yielding compound 245 (21.05 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 773.3641 (theoretical value: 773.3658). Theoretical elemental content (%) C 58 H 47 NO: C, 90.00; H, 6.12; N, 1.81. Analyzed elemental composition (%): C, 90.04; H, 6.09; N, 1.83. Synthesis Example 29: Preparation of Compound 254

[0275]

[0276] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-94, b-3 with an equimolar amount of b-254, and c-3 with an equimolar amount of c-32, yielding compound 254 (20.10 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 717.3049 (theoretical value: 717.3032). Theoretical elemental content (%) C 54 H 39 NO: C, 90.34; H, 5.48; N, 1.95. Measured elemental content (%): C, 90.36; H, 5.50; N, 1.92.

[0277] Synthesis Example 30: Preparation of Compound 263

[0278]

[0279] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-263, and c-3 was replaced with an equimolar amount of C-91, yielding compound 263 (18.88 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 655.2858 (theoretical value: 655.2875). Theoretical elemental content (%) C 49 H 37 NO: C, 89.74; H, 5.69; N, 2.14. Measured elemental content (%): C, 89.75; H, 5.71; N, 2.12.

[0280] Synthesis Example 31: Preparation of Compound 277

[0281]

[0282] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-277, b-3 with an equimolar amount of b-277, and c-3 with an equimolar amount of C-91, yielding compound 277 (23.65 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 845.3643 (theoretical value: 845.3658). Theoretical elemental content (%) C 64 H 47 NO: C, 90.85; H, 5.60; N, 1.66. Analyzed elemental composition (%): C, 90.88; H, 5.57; N, 1.64. Synthesis Example 32: Preparation of Compound 326

[0283]

[0284] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-326, and c-3 was replaced with an equimolar amount of c-326, yielding compound 326 (21.40 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 786.3984 (theoretical value: 786.3974). Theoretical elemental content (%) C 59 H 50 N2: C, 90.04; H, 6.40; N, 3.56. Measured elemental content (%): C, 90.08; H, 6.38; N, 3.53.

[0285] Synthesis Example 33: Preparation of Compound 427

[0286]

[0287] Following the method of Example 2, c-3 was replaced with an equimolar amount of c-427 to obtain compound 427 (18.85 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 730.3359 (theoretical value: 730.3348). Theoretical elemental content (%) C 55 H 42 N2: C, 90.38; H, 5.79; N, 3.83. Measured element content (%): C, 90.40; H, 5.81; N, 3.80.

[0288] Synthesis Example 34: Preparation of Compound 469

[0289]

[0290] Following the method of Example 2, b-3 was replaced with an equimolar amount of b-469, and c-3 was replaced with an equimolar amount of C-199, yielding compound 469 (22.25 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 829.4298 (theoretical value: 829.4284). Theoretical elemental content (%) C 62 H 55 NO: C, 89.71; H, 6.68; N, 1.69. Measured elemental content (%): C, 89.69; H, 6.70; N, 1.71.

[0291] Synthesis Example 35: Preparation of Compound 484

[0292]

[0293] Following the method of Example 2, a-3 was replaced with an equimolar amount of a-484, b-3 with an equimolar amount of b-484, and c-3 with an equimolar amount of C-484, yielding compound 484 (20.65 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 793.3662 (theoretical value: 793.3678). Theoretical elemental content (%) C 57 H 43 D4NOSi: C, 86.21; H, 6.47; N, 1.76. Measured elemental content (%): C, 86.23; H, 6.45; N, 1.74.

[0294] Synthesis Example 36: Preparation of Compound 560

[0295]

[0296] Following the method of Example 2, c-3 was replaced with an equimolar amount of C-560 to obtain compound 560 (20.12 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 718.2971 (theoretical value: 718.2984). Theoretical elemental content (%) C 53 H 38 N₂O: C, 88.55; H, 5.33; N, 3.90. Measured elemental content (%): C, 88.58; H, 5.35; N, 3.88.

[0297] Device Examples

[0298] 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%.

[0299] 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.

[0300] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s, while the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0301] Example 1: Fabrication of Organic Electroluminescent Device 1

[0302] ITO is used as the anode on a glass substrate; a hole injection layer is formed by vacuum evaporating 20 nm of NPB:F4TCNQ (mixed in a mass ratio of 95%:5%) on the anode; a first hole transport layer is formed by vacuum evaporating 35 nm of compound 3 of the present invention on the hole injection layer; a light-emitting layer is formed by vacuum evaporating 31 nm of BH-1:BD-1 (mixed in a mass ratio of 95%:5%) on the first hole transport layer; an electron transport layer is formed by vacuum evaporating 35 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) on the light-emitting layer; an electron injection layer is formed by vacuum evaporating 1.0 nm of LiF on the electron transport layer; and a cathode is formed by vacuum evaporating 120 nm of Al on the electron injection layer.

[0303] Examples 2-35: Fabrication of Organic Electroluminescent Devices 2-35

[0304] Replacing compound 3 in the first hole transport layer of Example 1 with compounds 32, 41, 44, 48, 58, 78, 84, 91, 94, 95, 99, 109, 122, 131, 142, 147, 152, 155, 183, 184, 198, 199, 200, 223, 239, 245, 254, 263, 277, 326, 427, 469, 484, and 560 respectively, while keeping the other steps the same, organic electroluminescent devices 2-35 are obtained.

[0305] Comparative Examples 1-3: Fabrication of Comparative Organic Electroluminescent Devices 1-3

[0306] By replacing compound 3 in the first hole transport layer of Example 1 with R-1, R-2, and R-3 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 3 were obtained.

[0307]

[0308] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 35 and Comparative Examples 1 to 3 of the present invention are shown in Table 1.

[0309] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0310]

[0311]

[0312] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0313] As can be seen from Table 1, compared with Comparative Examples 1 to 3, when the aromatic amine derivatives of Formula 1 of the present invention are used in the first hole transport layer of organic electroluminescent devices, the efficiency of the organic electroluminescent devices is effectively improved and the lifespan of the devices is improved, further demonstrating that the compounds of the present invention have excellent hole transport capabilities.

[0314] Example 36: Fabrication of Organic Electroluminescent Device 36

[0315] ITO is used as the anode on a glass substrate; a hole injection layer of 55 nm DNTPD is vacuum-deposited on the anode; a first hole transport layer of 27 nm NPB is vacuum-deposited on the hole injection layer; compound 3 of the present invention is vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; a light-emitting layer of 30 nm BH-2:BD-2 (mixed at a mass ratio of 97%:3%) is vacuum-deposited on the second hole transport layer; an electron transport layer of 30 nm ET-1:LiQ (mixed at a mass ratio of 1:1) is vacuum-deposited on the light-emitting layer; an electron injection layer of 1.0 nm LiF is vacuum-deposited on the electron transport layer; and a cathode of 120 nm Al is vacuum-deposited on the electron injection layer.

[0316] Examples 37-70: Fabrication of Organic Electroluminescent Devices 37-70

[0317] Replacing compound 3 in the second hole transport layer of Example 36 with compounds 32, 41, 44, 48, 58, 78, 84, 91, 94, 95, 99, 109, 122, 131, 142, 147, 152, 155, 183, 184, 198, 199, 200, 223, 239, 245, 254, 263, 277, 326, 427, 469, 484, and 560 respectively, while keeping the other steps the same, organic electroluminescent devices 37-70 are obtained.

[0318] Comparative Examples 4-6: Fabrication of Comparative Organic Electroluminescent Devices 4-6

[0319] By replacing compound 3 in the second hole transport layer of Example 36 with R-1, R-3, and R-4 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 4 to 6 were obtained.

[0320]

[0321] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 36-70 and Comparative Examples 4-6 of this invention are shown in Table 2.

[0322] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0323]

[0324]

[0325] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0326] As can be seen from the results in Table 2, when the aromatic amine derivatives of the present invention are used in organic electroluminescent devices as the second hole transport layer material, the device performance is significantly improved compared with comparative examples 4 to 6, exhibiting the advantages of high luminous efficiency and long service life.

[0327] Example 71: Fabrication of Organic Electroluminescent Device 71

[0328] ITO is used as the anode on a glass substrate; a hole injection layer is formed by vacuum evaporating 15 nm of NPB:F4TCNQ (mixed in a mass ratio of 95%:5%) on the anode; a first hole transport layer is formed by vacuum evaporating 20 nm of NPB on the hole injection layer; a second hole transport layer is formed by vacuum evaporating 10 nm of HT-2 on the first hole transport layer; a third hole transport layer is formed by vacuum evaporating 10 nm of compound 3 of the present invention on the second hole transport layer; a light-emitting layer is formed by vacuum evaporating 30 nm of BH-3:BD-3 (mixed in a mass ratio of 98%:2%) on the third hole transport layer; an electron transport layer is formed by vacuum evaporating 30 nm of ET-1:Liq (mixed in a mass ratio of 1:1) on the light-emitting layer; an electron injection layer is formed by vacuum evaporating 1.0 nm of LiF on the electron transport layer; and a cathode is formed by vacuum evaporating 120 nm of Al on the electron injection layer.

[0329] Examples 72-105: Fabrication of Organic Electroluminescent Devices 72-105

[0330] Replace compound 3 in the third hole transport layer of Example 71 with compounds 32, 41, 44, 48, 58, 78, 84, 91, 94, 95, 99, 109, 122, 131, 142, 147, 152, 155, 183, 184, 198, 199, 200, 223, 239, 245, 254, 263, 277, 326, 427, 469, 484, and 560 respectively, and follow the same steps to obtain organic electroluminescent devices 72-105.

[0331] Comparative Examples 7-9: Fabrication of Comparative Organic Electroluminescent Devices 7-9

[0332] By replacing compound 6 in the third hole transport layer of Example 77 with R-1, R-5, and R-6 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 7-9 were obtained.

[0333]

[0334] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 71-105 and Comparative Examples 7-9 of this invention are shown in Table 3.

[0335] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0336]

[0337]

[0338] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0339] As can be seen from the results in Table 3, when the aromatic amine derivatives of the present invention are used in organic electroluminescent devices as the third hole transport layer material, the luminous efficiency and lifespan of the devices are improved compared with those of Comparative Examples 7 to 9.

[0340] Example 106: Fabrication of Organic Electroluminescent Device 106 (Stacked Organic Electroluminescent Device)

[0341] ITO was used as the anode on a glass substrate; a hole injection layer was formed by vacuum evaporating 15 nm of NPB:F4TCNQ (mixed at a mass ratio of 97%:3%) on the anode; a hole transport layer 1 was formed by vacuum evaporating 35 nm of NPB on the hole injection layer; a light-emitting layer 1 was formed by vacuum evaporating 25 nm of BH-1:BD-1 (mixed at a mass ratio of 96%:4%) on the hole transport layer 1; an electron transport layer 1 was formed by vacuum evaporating 20 nm of ET-1:LiQ (mixed at a mass ratio of 1:1) on the light-emitting layer 1; an N-type charge generation layer was formed by vacuum evaporating 10 nm of Bphen:Li (mixed at a mass ratio of 98%:2%) on the electron transport layer 1; and a hole transport layer 2 was formed by vacuum evaporating 10 nm of Bphen:Li (mixed at a mass ratio of 98%:2%) on the N-type charge generation layer. A 10 nm layer of compound 3:HAT-CN (mixed at a mass ratio of 95%:5%) was vacuum-deposited on the top layer to form a P-type charge generation layer; a 25 nm layer of NPB was vacuum-deposited on the P-type charge generation layer to form a hole transport layer 2; a 25 nm layer of BH-1:BD-1 (mixed at a mass ratio of 96%:4%) was vacuum-deposited on the hole transport layer 2 to form a light-emitting layer 2; a 20 nm layer of ET-1:LiQ (mixed at a mass ratio of 1:1) was vacuum-deposited on the light-emitting layer 2 to form an electron transport layer 2; a 10 nm layer of EI-1:Li (mixed at a mass ratio of 97%:3%) was vacuum-deposited on the electron transport layer 2 to form an electron injection layer; and a 110 nm layer of Al was vacuum-deposited on the electron injection layer to form a cathode.

[0342] Examples 107-125: Fabrication of Organic Electroluminescent Devices 107-125

[0343] In Example 106, compound 3 in the P-type charge generation layer was replaced with compounds 32, 44, 48, 58, 84, 91, 94, 95, 99, 109, 131, 155, 184, 198, 239, 254, 263, 427, and 469, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 107-125.

[0344] Comparative Examples 10-11: Fabrication of Comparative Organic Electroluminescent Devices 10-11

[0345] By replacing compound 3 in the charge generation layer of Example 106P with R-7 and NPB respectively, and keeping the other steps the same, comparative organic electroluminescent devices 10-11 were obtained.

[0346]

[0347] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 106-125 and Comparative Examples 10-11 of this invention are shown in Table 4.

[0348] Table 4. Test data on the luminescence characteristics of organic electroluminescent devices.

[0349]

[0350]

[0351] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0352] As can be seen from the results in Table 4, when the aromatic amine derivatives of the present invention are applied to the P-type charge generation layer material of organic electroluminescent devices, the luminous efficiency and lifespan of the organic electroluminescent devices are greatly improved compared with Comparative Examples 10-11. This indicates that the compounds of the present invention have good technical effects when used as P-type charge generation layer materials in stacked OLED devices.

[0353] 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. An aromatic amine derivative, characterized in that, It has the general formula shown in structural formula 1, in, Selected from any one of the following groups: Each time R3 and R4 appear, they are selected from hydrogen, deuterium, and -Si(R) in the same or different ways. W 3. Any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl; Each time R9 appears, it is selected from hydrogen, deuterium, or -Si(R) in a specific order, either identically or differently. W 3. Any one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R 10 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; Each time f1 appears, it is selected from 1, 2, 3, 4, or 5, either the same or different. Each time f2 appears, it is selected from 1, 2, 3, or 4, either the same or different. Each time f3 appears, it is selected from 1, 2, 3, 4, 5, 6, or 7, either the same or different. Each time f5 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. Each time f6 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different. Each time f8 appears, it is selected from 1, 2, or 3, either the same or different. Each time b1 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different. R5 and R6 are independently selected from substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl; Each time R7 and R8 appear, they are selected from hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, or any one of these. a is selected from 1, 2, 3, or 4; b is selected from 1, 2, 3, or 4; c is selected from 1, 2, 3, or 4; d is selected from 1, 2, 3, or 4. X is selected from O atoms, N(R) atoms. d ); Each time v appears, it is always selected from CH; the v at the bonding site is selected from C; The R d Selected from any one of the following: substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl, and C6-C12 aryl; The R a R b R c Each time it appears, it is selected from hydrogen or deuterium, either the same or different; the e is selected from 1, 2 or 3; The L1 and L2 are independently selected from single bonds or any of the following groups: The R 11 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; Each time g1 appears, it is selected from 1, 2, 3, or 4, either the same or different; each time g2 appears, it is selected from 1, 2, or 3, either the same or different. The L3 is selected from a single bond or any of the following groups: The R 12a Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl; The R 12 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R 14 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; Each time h1 appears, it is selected from 1, 2, 3, or 4, either the same or different; each time h2 appears, it is selected from 1, 2, or 3, either the same or different; each time h3 appears, it is selected from 1 or 2, either the same or different; each time h4 appears, it is selected from 1, 2, 3, 4, 5, or 6, either the same or different; each time h5 appears, it is selected from 1, 2, 3, 4, 5, 6, 7, or 8, either the same or different; when R 12a When h1 is selected from phenyl, h1 is selected from 1; Each R W The same or different groups are selected from the following groups: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The term "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, methyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl. In the case of substitution by multiple substituents, the multiple substituents may be the same as or different from each other. The condition is that the aromatic amine derivative is not: 。 2. The aromatic amine derivative according to claim 1, characterized in that, In Equation 1 Selected from any one of the following groups: 。 3. The aromatic amine derivative according to claim 1, characterized in that, In Equation 1 Selected from any one of the following groups: Each time R7 and R8 appear, they are selected from hydrogen, deuterium, substituted or unsubstituted groups of any one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and phenyl.

4. The aromatic amine derivative according to claim 1, characterized in that, In Equation 1 Selected from any one of the following groups: The R d The group is selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl.

5. The aromatic amine derivative according to claim 1, characterized in that, The L1 and L2 are independently selected from single bonds or any of the following groups: The R 11 Each time it appears, it is selected from either hydrogen or deuterium, either the same or different.

6. The aromatic amine derivative according to claim 1, characterized in that, The L3 is selected from a single bond or any of the following groups: The R 12 Each time it appears, it is selected from the same or different groups of hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

7. An aromatic amine derivative, characterized in that, The aromatic amine derivative is selected from any one of the following chemical structures: 。 8. An organic electroluminescent device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer located between the first electrode and the second electrode, the organic layer comprising a hole transport region, a light-emitting layer, and an electron transport region, characterized in that at least one layer in the hole transport region contains any one or a combination of at least two of the aromatic amine derivatives according to any one of claims 1-7.

9. An organic electroluminescent device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer located between the first electrode and the second electrode, the organic layer comprising a hole transport region, two or more light-emitting layers, and an electron transport region, wherein each light-emitting layer is provided with an N-type charge generation layer and a P-type charge generation layer in the middle, characterized in that the P-type charge generation layer contains any one or a combination of at least two of the aromatic amine derivatives as described in any one of claims 1-7.

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