An arylamine compound and an organic electroluminescence device thereof

Abstract

The present application relates to the technical field of organic photoelectric material, in particular to a kind of arylamine compound and organic electroluminescent device thereof.The arylamine compound provided by the present application has good spatial configuration, excellent arrangement between molecules, excellent hole transport capacity, good film stability, proper HOMO and T1 value, good matching with adjacent organic functional layer, high glass transition temperature, excellent thermal stability and chemical stability, as light-emitting auxiliary layer, can transport hole well, also can block exciton from light-emitting layer to hole transport region, avoid interface luminescence, effectively improve the luminous efficiency of OLED device, prolong the service life of device;It also has higher refractive index, can be applied to OLED device as cover layer material, enhance the light transmittance of device, while resistant to high temperature, can also effectively isolate water vapor, oxygen and corrosive gas, thereby delaying the aging of device, further improve the luminous efficiency and service life of device.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have the characteristics of being thin and light, having a wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility. They have been widely used in the fields of lighting and display and are considered by the industry to be one of the most promising display and lighting technologies.

[0003] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes: a cathode and an anode. This emissive layer contains a luminescent material (guest material). When a specific operating voltage is applied between the two electrodes, holes and electrons are injected from the anode and cathode respectively, reaching the emissive layer. There, they recombine to generate excitons, releasing energy. Under the influence of an electric field, the excitons migrate, transferring energy to the luminescent material. Electrons in the luminescent material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons then migrate back to the ground state, releasing energy as light, thus producing the luminescence phenomenon. To improve device performance, additional organic functional layers are placed between the anode and the emissive layer, and between the cathode and the emissive layer. Generally, the region between the anode and the emissive layer is the hole transport region, primarily responsible for injecting and transporting holes, including hole injection layers, hole transport layers, luminescent auxiliary layers, and electron blocking layers. The region between the cathode and the emissive layer is the electron transport region, primarily responsible for injecting and transporting electrons, including electron injection layers, electron transport layers, and hole blocking layers.

[0004] In addition to setting an organic functional layer between the anode and cathode, a capping layer is also set on the outside of the light-emitting electrode (away from the non-light-emitting electrode). Generally, the capping layer has a high refractive index, which can improve the light transmittance of the device, change the light emission direction, and thus improve the luminous efficiency and color purity of the device.

[0005] To further improve the performance of OLED devices, such as luminous efficiency, color purity, and lifespan, it is necessary to develop high-performance hole transport materials, electron transport materials, and capping materials. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention provides an aromatic amine compound that possesses high hole mobility, appropriate HOMO and T1 values, excellent thermal and chemical stability, and a high refractive index. It can be used both as a hole transport material and as a capping layer material in OLED devices to improve the luminous efficiency and lifespan of OLED devices. It has the structure shown in formula (I):

[0007]

[0008] Wherein, Ar1 is selected from the structure shown in formula (IA), and Ar2 is selected from the structure shown in formula (IB):

[0009]

[0010] Each time a1 appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different; each time b1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time a2 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time b2 appears, it is selected from 0, 1, 2 or 3, either the same or different.

[0011] Each time R1 and R2 appear, they are selected from one of the following groups, either the same or different: hydrogen atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring. Furthermore, two adjacent R1 or two adjacent R2 can be linked to form one of the following groups: substituted or unsubstituted C3-C7 saturated or unsaturated aliphatic ring, or substituted or unsubstituted C6-C10 aromatic ring.

[0012] The Ar3 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring fused with a C3-C7 aliphatic ring;

[0013] The L1, L2, and L3 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene group, or a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;

[0014] The substituents in R1, R2, L1, and L2 that are “substituted or unsubstituted” are selected from fluorine atoms; cyano groups; C1-C4 alkyl groups substituted or unsubstituted by one or more fluorine atoms; C3-C10 cycloalkyl groups substituted or unsubstituted by one or more of the group consisting of fluorine atoms, cyano groups, and C1-C4 alkyl groups; and C6-C12 aryl groups substituted or unsubstituted by one or more of the group consisting of fluorine atoms, cyano groups, C1-C4 alkyl groups, and C3-C10 cycloalkyl groups.

[0015] In Ar3 and L3, the substituents in "substituted or unsubstituted" are selected from deuterium atom; fluorine atom; cyano group; C1-C4 alkyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; C3-C10 cycloalkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group and C1-C4 alkyl group; and C6-C12 aryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group, C1-C4 alkyl group and C3-C10 cycloalkyl group.

[0016] The condition is that at least one aromatic ring in Ar3 or L3 must be replaced by a deuterium atom, and the deuteration rate of formula (I) is less than 50%.

[0017] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode opposite to the anode, and the organic layer contains one or more of the aromatic amine compounds described in the present invention.

[0018] Beneficial effects:

[0019] The aromatic amine compound provided by this invention has a good spatial configuration, excellent molecular arrangement, excellent hole transport capability, and good film stability. It also has appropriate HOMO and T1 values, which can be well matched with adjacent organic functional layers. At the same time, it has a high glass transition temperature, excellent thermal and chemical stability. When used as a light-emitting auxiliary layer, it can effectively transport holes and prevent excitons from moving from the light-emitting layer to the hole transport region, thereby avoiding interfacial luminescence and effectively improving the luminous efficiency of OLED devices and extending the device's lifespan. It also has a high refractive index and can be used as a capping layer material in OLED devices to enhance the device's light transmittance. While being resistant to high temperatures, it can also effectively isolate water vapor, oxygen, and corrosive gases, thereby delaying device aging and further improving the device's luminous efficiency and lifespan. Detailed Implementation

[0020] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0021] In the compounds of this invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and comprises 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.

[0022] 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".

[0023] The deuteration rate of a certain compound described in this invention refers to the proportion of deuterium relative to the total number of hydrogens, deuterations, and tritium atoms present in the compound.

[0024] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0025] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0026] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0027] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentenyl or cyclohexenyl.

[0028] The heterocyclic alkyl group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, silicon, selenium, and phosphorus atoms, preferably nitrogen, oxygen, or sulfur. It is preferable to contain 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It is preferable to have 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic groups are preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0029] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, fused-ring aryl, or a fused group of aryl and aliphatic ring. It preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, or spiro-adamantyl-fluorenyl.

[0030] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0031] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0032] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0033] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0034] 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 The alkyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, trialkylsilyl, dialkylarylsilyl, diarylalkylsilyl, and triarylsilyl groups, when substituted with multiple substituents, have the multiple substituents being the same or different from each other; preferably, this means unsubstituted or substituted with 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, and cyclopropane. Methyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, deuterated cyclobutane, cyclopentane, methyl-substituted cyclopentane, deuterated cyclopentane, cyclohexane, methyl-substituted cyclohexane, deuterated cyclohexane, cycloheptane, cyclopentenyl, methyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl-substituted piperazine, phenyl-substituted Piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthryl, deuterated phenanthryl, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl, where the multiple substituents are the same or different from each other.

[0035] In this specification, when the position of a substituent or linking site on the aromatic ring is not fixed, it means that it can be linked to any of the optional sites on the aromatic ring. For example, Can represent Can represent Can represent

[0036] And so on.

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

[0038] The linked ring structure described in this invention (e.g., forming saturated or unsaturated C3-C10 carbon rings, forming substituted or unsubstituted saturated or unsaturated C3-C6 carbon rings) refers to the individual groups being connected to each other by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0039]

[0040] 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.

[0041] This invention provides an aromatic amine compound having the structure shown in formula (I):

[0042]

[0043] Wherein, Ar1 is selected from the structure shown in formula (IA), and Ar2 is selected from the structure shown in formula (IB):

[0044]

[0045] Each time a1 appears, it is selected from 0, 1, 2, 3, 4 or 5, either the same or different; each time b1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time a2 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different; each time b2 appears, it is selected from 0, 1, 2 or 3, either the same or different.

[0046] Each time R1 and R2 appear, they are selected from one of the following groups, either the same or different: hydrogen atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or a group formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring. Furthermore, two adjacent R1 or two adjacent R2 can be linked to form one of the following groups: substituted or unsubstituted C3-C7 saturated or unsaturated aliphatic ring, or substituted or unsubstituted C6-C10 aromatic ring.

[0047] The Ar3 is selected from one of the following: a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 aromatic ring fused with a C3-C7 aliphatic ring;

[0048] The L1, L2, and L3 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene group, or a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a C3-C7 aliphatic ring;

[0049] The substituents in R1, R2, L1, and L2 that are “substituted or unsubstituted” are selected from fluorine atoms; cyano groups; C1-C4 alkyl groups substituted or unsubstituted by one or more fluorine atoms; C3-C10 cycloalkyl groups substituted or unsubstituted by one or more of the group consisting of fluorine atoms, cyano groups, and C1-C4 alkyl groups; and C6-C12 aryl groups substituted or unsubstituted by one or more of the group consisting of fluorine atoms, cyano groups, C1-C4 alkyl groups, and C3-C10 cycloalkyl groups.

[0050] In Ar3 and L3, the substituents in "substituted or unsubstituted" are selected from deuterium atom; fluorine atom; cyano group; C1-C4 alkyl group substituted or unsubstituted by one or more of deuterium atom and fluorine atom; C3-C10 cycloalkyl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group and C1-C4 alkyl group; and C6-C12 aryl group substituted or unsubstituted by one or more of the group consisting of deuterium atom, fluorine atom, cyano group, C1-C4 alkyl group and C3-C10 cycloalkyl group.

[0051] The condition is that at least one aromatic ring in Ar3 or L3 must be replaced by a deuterium atom, and the deuteration rate of formula (I) is less than 50%.

[0052] Preferably, the deuteration rate of formula (I) is less than 40%; more preferably, the deuteration rate of formula (I) is less than 35%; even more preferably, the deuteration rate of formula (I) is less than 30%.

[0053] Preferably, the deuteration rate of formula (I) is between 5% and 40%; more preferably, the deuteration rate of formula (I) is between 5% and 35%; even more preferably, the deuteration rate of formula (I) is between 5% and 30%.

[0054] Preferably, the deuteration rate of formula (I) is between 10% and 40%; more preferably, the deuteration rate of formula (I) is between 10% and 35%; even more preferably, the deuteration rate of formula (I) is between 10% and 30%.

[0055] Preferably, the substituents in "substituted or unsubstituted" of R1, R2, L1, and L2 are selected from fluorine atoms, cyano, methyl, trifluoromethyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, methyl-substituted norbornyl, phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, fluorine-substituted naphthyl, and cyano-substituted naphthyl.

[0056] Preferably, the substituents in "substituted or unsubstituted" of Ar3 and L3 are selected from deuterium, fluorine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, deuterated tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, deuterated adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, norbornyl, deuterated norbornyl, and methyl-substituted norbornyl. One of the following: alkyl, phenyl, deuterated phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, biphenyl, deuterated biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, naphthyl, deuterated naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, fluorine-substituted naphthyl, and cyano-substituted naphthyl.

[0057] Preferably, the formula (IA) is selected from one of the following structures:

[0058]

[0059] Wherein, the a 11Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either the same or different; b 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0060] The R mentioned 11 Each time it appears, it is selected from the same or different groups of hydrogen atom, fluorine atom, cyano, methyl, trifluoromethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl-substituted phenyl, naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, indanyl, and tetrahydronaphthyl.

[0061] Preferably, the formula (IA) is selected from one of the following structures:

[0062]

[0063]

[0064] Preferably, the formula (IB) is selected from one of the following structures:

[0065]

[0066] Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either the same or different;

[0067] The R mentioned 21Each time it appears, it is selected from the same or different groups of hydrogen atom, fluorine atom, cyano, methyl, trifluoromethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl-substituted phenyl, naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, indanyl, and tetrahydronaphthyl.

[0068] Preferably, the formula (IB) is selected from one of the following structures:

[0069]

[0070]

[0071] Preferably, the Ar3 is selected from one of the following structures:

[0072]

[0073]

[0074] Wherein, the a 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 31 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 31 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, either identically or differently; the f mentioned 31 Each time it appears, it is selected from 0, 1, or 2, either the same or different;

[0075] The R mentioned 31Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, deuterated methyl-substituted phenyl, isopropyl-substituted phenyl, deuterated isopropyl-substituted phenyl, tert-butyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl-substituted phenyl, deuterated naphthyl-substituted phenyl, naphthyl, deuterated One of the following: naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, deuterated phenyl-substituted naphthyl, naphthyl-substituted naphthyl, deuterated naphthyl-substituted naphthyl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, deuterated methyl-substituted biphenyl, isopropyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, indanyl, deuterated indanyl, tetrahydronaphthyl, and deuterated tetrahydronaphthyl.

[0076] Preferably, the Ar3 is selected from one of the following structures:

[0077]

[0078]

[0079] Preferably, the Ar3 is selected from those of the above groups that contain deuterium.

[0080] Preferably, L1 and L2 are independently selected from a single bond or one of the following structures:

[0081]

[0082] Wherein, the a 41 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 41 Each time it appears, it is the same or different number 0, 1, 2 or 3; the c mentioned 41 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 41 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0083] The R mentioned 41Each time it appears, it is selected from the same or different groups of hydrogen atom, fluorine atom, cyano, methyl, trifluoromethyl, isopropyl, tert-butyl, adamantyl, norbornel, phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornel-substituted phenyl, naphthyl-substituted phenyl, naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, naphthyl-substituted naphthyl, biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, indanyl, and tetrahydronaphthyl.

[0084] Preferably, L1 and L2 are independently selected from a single bond or one of the following structures:

[0085]

[0086]

[0087] Preferably, L3 is selected from a single bond or one of the following structures:

[0088]

[0089] Wherein, the a 51 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 51 Each time it appears, it is the same or different number 0, 1, 2 or 3; the c mentioned 51 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 51 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 51 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0090] The R mentioned 51Each time it appears, it is selected from the same or different groups: hydrogen atom, deuterium atom, fluorine atom, cyano, methyl, trifluoromethyl, deuterated methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, phenyl, deuterated phenyl, fluorine-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, deuterated methyl-substituted phenyl, isopropyl-substituted phenyl, deuterated isopropyl-substituted phenyl, tert-butyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl-substituted phenyl, deuterated naphthyl-substituted phenyl, naphthyl, deuterated One of the following: naphthyl, fluorine-substituted naphthyl, cyano-substituted naphthyl, methyl-substituted naphthyl, isopropyl-substituted naphthyl, tert-butyl-substituted naphthyl, phenyl-substituted naphthyl, deuterated phenyl-substituted naphthyl, naphthyl-substituted naphthyl, deuterated naphthyl-substituted naphthyl, biphenyl, deuterated biphenyl, fluorine-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, deuterated methyl-substituted biphenyl, isopropyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, indanyl, deuterated indanyl, tetrahydronaphthyl, and deuterated tetrahydronaphthyl.

[0091] Preferably, L3 is selected from a single bond or one of the following structures:

[0092]

[0093]

[0094] Preferably, the L3 is selected from those of the above groups that contain deuterium.

[0095] Most preferably, the aromatic amine compound is selected from one of the following compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The above only lists some specific structural forms of the aromatic amine compounds represented by formula (I), but the present invention is not limited to these chemical structures. Any chemical structure based on formula (I) with substituents as defined in the present invention should be included.

[0104] The aromatic amine compound represented by formula (I) of this invention can be prepared by one of the following synthetic routes:

[0105] Synthesis Route 1:

[0106]

[0107] Synthesis Route 2:

[0108]

[0109] Synthesis Route 3:

[0110]

[0111] Wherein, X1 and X2 are independently selected from chlorine atoms, bromine atoms, or iodine atoms;

[0112] L1 to L3 and Ar1 to Ar3 are as described in this invention.

[0113] In the above synthetic routes, the target compound (I) is obtained by reacting aromatic amine compound (Y1) with halides (Y2) and (Y3) via a Buchwald-Hartwig coupling reaction. The reaction order of aromatic amine compound (Y1) with halides (Y2) and (Y3) is not limited; it can react with (Y2) first and then with (Y3), or with (Y3) first and then with (Y2), or with both (Y2) and (Y3) simultaneously.

[0114] All the above reaction routes employ commonly used reaction types in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation methods use readily available raw materials, have simple processes, and yield excellent results. The compound represented by formula (I) provided by this invention can also be synthesized using other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0115] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer comprises at least one of a hole transport region between the anode and the cathode, a light-emitting layer, an electron transport region, and a capping layer on the side of the cathode opposite to the anode, and the organic layer contains one or more of the aromatic amine compounds described in the present invention.

[0116] Preferably, the organic layer includes a hole transport region containing the aromatic amine compound described in this invention.

[0117] The hole transport region of the present invention includes at least one of a hole injection layer, a hole transport layer, and a light emission assist layer.

[0118] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and one of the hole injection layer and the hole transport layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0119] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein one of the hole injection layer, the hole transport layer, and the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention.

[0120] Preferably, the organic layer includes a capping layer containing one or more of the aromatic amine compounds described in this invention.

[0121] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used, such as 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), and other chemical compounds. The compounds are HT-1 to HT-19, p-1 to p-3, and the aromatic amine compounds described in this invention, but are not limited thereto. Preferably, the hole injection layer is a monolayer structure composed of a matrix material and a dopant material. The matrix material can be a triaromatic amine compound, such as HT-1 to HT-19. The dopant material can be an axial alkene compound, preferably p-1, p-2, or p-3. More preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:50. Even more preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:10.

[0122]

[0123] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2 Substances with a concentration of / Vs or higher, such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), compounds HT-1 to HT-19 as shown above, and aromatic amine compounds described in this invention, but not limited thereto.

[0124] The luminescent auxiliary 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. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1 [1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, compounds HT-1 to HT-19 as shown above, and aromatic amine compounds described in this invention, but not limited thereto.

[0125] The luminescent layer of the present invention comprises a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material. Examples include metal complexes such as aluminum complexes or zinc complexes, heterocyclic compounds such as oxadiazole derivatives, benzoxazole derivatives, benzothiazole derivatives or benzimidazole derivatives, fused aromatic compounds such as carbazole derivatives or anthracene derivatives, and aromatic amine compounds such as triaromatic amine derivatives or fused polycyclic aromatic amine derivatives. Examples include Alq3, BAlq, TPBI, TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), and 9,10-bis(2-naphthyl)anthracene (ADN), but are not limited to these.

[0126] The electron transport region of the present invention includes at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0127] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0128] The electron transport 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. It can use aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymers, etc. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline) beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but is not limited to these.

[0129] The hole-blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The selected material must have a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10. -6 cm 2 A value of / Vs or higher facilitates electron transport. One or more of the following substances can be selected: aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, and polymers. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI) and BAlq, but these are not limited to these.

[0130] The anode described in this invention can be a reflective anode, such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a layered structure with a high work function that is transparent or semi-transparent, such as a layered structure formed of indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2). The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or semi-transparent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0131] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to make a reflective electrode, a transparent electrode, or a semi-transparent electrode. If a bottom-emitting device is to be made, a reflective cathode needs to be made. If a top-emitting device is to be made, a transparent or semi-transparent cathode needs to be made.

[0132] 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. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compounds described in this invention, but are not limited thereto.

[0133]

[0134] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0135] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0136] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention.

[0137] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention.

[0138] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0139] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the capping layer contains one or more of the aromatic amine compounds described in this invention.

[0140] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0141] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the capping layer contains one or more of the aromatic amine compounds described in this invention.

[0142] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention.

[0143] Preferably, the organic layer comprises a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the capping layer contains one or more of the aromatic amine compounds described in this invention.

[0144] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention.

[0145] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer, wherein the capping layer contains one or more of the aromatic amine compounds described in this invention.

[0146] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0147] The thickness of each of the aforementioned organic layers and capping layers is typically between 5 nm and 100 μm, preferably between 10 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0148] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0149] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0150] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent.

[0151] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0152] Synthesis Example 1: Synthesis of intermediate dd

[0153]

[0154] Under nitrogen protection, ee-31 (12.79 g, 60.00 mmol), ff-31 (9.62 g, 60.00 mmol), Pd(PPh3)4 (0.81 g, 0.70 mmol), potassium carbonate (13.82 g, 100.00 mmol), and 400 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 4 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 over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out under cooling, and the solid was filtered. The obtained solid was recrystallized from toluene to give intermediate dd-31 (12.54 g, yield 84%); HPLC purity ≥ 99.75%. Mass spectrometry m / z: 248.1279 (theoretical value: 248.1270).

[0155] Following the above synthesis method, other intermediates dd required for this invention were synthesized, and the relevant raw materials are shown in Table 101:

[0156] Table 101:

[0157]

[0158] Synthesis Example 2: Synthesis of Compound 1

[0159]

[0160] Synthetic intermediate cc-1:

[0161] Under nitrogen protection, aa-1 (19.89 g, 60.00 mmol), bb-1 (23.84 g, 60.00 mmol), Pd(OAc)2 (0.16 g, 0.70 mmol), P(t-Bu)3 (0.14 g, 0.70 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and refluxed for 5 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The extract was allowed to stand and separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was then filtered again and finally recrystallized from toluene / methanol (10:3) to give intermediate cc-1 (31.48 g, yield 81%) with an HPLC purity ≥ 99.87%. Mass spectrometry m / z: 647.2628 (theoretical value: 647.2613).

[0162] Synthesized compound 1:

[0163] Under nitrogen protection, cc-1 (19.43 g, 30.00 mmol), dd-1 (4.86 g, 30.00 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), BINAP (0.50 g, 0.80 mmol), sodium tert-butoxide (4.81 g, 50 mmol), and 150 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 7 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The extract was allowed to stand and separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was then filtered again and finally recrystallized from toluene / methanol (10:1) to give compound 1 (16.18 g, 74%) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 728.3256 (theoretical value: 728.3240). Theoretical elemental content (%) C 56 H 32 D5N: C, 92.27; H, 5.81; N, 1.92. Measured elemental content (%): C, 92.25; H, 5.84; N, 1.94.

[0164] Synthesis Example 3: Synthesis of Compound 2

[0165]

[0166] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-2, and all other steps were the same, yielding compound 2 (17.48 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 808.3815 (theoretical value: 808.3804). Theoretical elemental content (%) C 62 H 32D9N: C, 92.04; H, 6.23; N, 1.73. Measured elemental content (%): C, 92.06; H, 6.25; N, 1.69.

[0167] Synthesis Example 4: Synthesis of Compound 13

[0168]

[0169] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-13, and all other steps were the same, yielding compound 13 (18.85 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 884.4095 (theoretical value: 884.4086). Theoretical elemental content (%) C 68 H 32 D 11 N: C, 92.27; H, 6.15; N, 1.58. Measured elemental content (%): C, 92.26; H, 6.18; N, 1.53.

[0170] Synthesis Example 5: Synthesis of Compound 19

[0171]

[0172] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-19, and all other steps were the same, yielding compound 19 (19.48 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 853.3659 (theoretical value: 853.3647). Theoretical elemental content (%) C 66 H 39 D4N: C, 92.81; H, 5.55; N, 1.64. Measured elemental content (%): C, 92.79; H, 5.52; N, 1.66.

[0173] Synthesis Example 6: Synthesis of Compound 23

[0174]

[0175] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-23, and all other steps were the same, yielding compound 23 (17.78 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 846.3980 (theoretical value: 846.3991). Theoretical elemental content (%) C 65 H 38 D7N: C, 92.16; H, 6.19; N, 1.65. Measured elemental content (%): C, 92.18; H, 6.15; N, 1.67.

[0176] Synthesis Example 7: Synthesis of Compound 31

[0177]

[0178] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-31, and all other steps were the same, yielding compound 31 (20.13 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 859.4104 (theoretical value: 859.4116). Theoretical elemental content (%) C 66 H 45 D4N: C, 92.16; H, 6.21; N, 1.63. Measured elemental content (%): C, 92.11; H, 6.23; N, 1.66.

[0179] Synthesis Example 8: Synthesis of Compound 32

[0180]

[0181] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-32, and all other steps were the same, yielding compound 32 (20.34 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 903.3819 (theoretical value: 903.3803). Theoretical elemental content (%) C 70 H 41 D4N: C, 92.99; H, 5.46; N, 1.55. Measured elemental content (%): C, 92.98; H, 5.44; N, 1.59.

[0182] Synthesis Example 9: Synthesis of Compound 45

[0183]

[0184] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-45, and all other steps were the same, yielding compound 45 (18.36 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 804.3563 (theoretical value: 804.3553). Theoretical elemental content (%) C 62 H 36 D5N: C, 92.50; H, 5.76; N, 1.74. Measured elemental content (%): C, 92.53; H, 5.74; N, 1.72.

[0185] Synthesis Example 10: Synthesis of Compound 47

[0186]

[0187] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-47, and all other steps were the same, yielding compound 47 (18.51 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 856.3844 (theoretical value: 856.3835). Theoretical elemental content (%) C 66 H 36 D7N: C, 92.49; H, 5.88; N, 1.63. Measured elemental content (%): C, 92.46; H, 5.89; N, 1.60.

[0188] Synthesis Example 11: Synthesis of Compound 55

[0189]

[0190] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-55, and all other steps were the same, yielding compound 55 (19.05 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 906.3983 (theoretical value: 906.3991). Theoretical elemental content (%) C 70 H 38 D7N: C, 92.68; H, 5.78; N, 1.54. Measured elemental content (%): C, 92.65; H, 5.77; N, 1.58.

[0191] Synthesis Example 12: Synthesis of Compound 57

[0192]

[0193] In Synthesis Example 2, dd-1 was replaced with an equimolar amount of dd-57, and all other steps were the same, yielding compound 57 (18.77 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 880.3854 (theoretical value: 880.3866). Theoretical elemental content (%) C 68 H 40 D5N: C, 92.69; H, 5.72; N, 1.59. Measured elemental content (%): C, 92.70; H, 5.74; N, 1.56.

[0194] Synthesis Example 13: Synthesis of Compound 73

[0195]

[0196] In Synthesis Example 2, bb-1 and dd-1 were replaced with equimolar amounts of bb-73 and dd-73, with all other steps remaining the same, to obtain compound 73 (20.33 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 879.3815 (theoretical value: 879.3803). Theoretical elemental content (%) C 68 H 41 D4N: C, 92.80; H, 5.61; N, 1.59. Measured elemental content (%): C, 92.82; H, 5.60; N, 1.58.

[0197] Synthesis Example 14: Synthesis of Compound 88

[0198]

[0199] In Synthesis Example 2, bb-1 and dd-1 were replaced with equimolar amounts of bb-88 and dd-88, respectively, while maintaining the same other steps, to obtain compound 88 (18.70 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 853.3640 (theoretical value: 853.3647). Theoretical elemental content (%) C 66 H 39 D4N: C, 92.81; H, 5.55; N, 1.64. Measured elemental content (%): C, 92.78; H, 5.54; N, 1.67.

[0200] Synthesis Example 15: Synthesis of Compound 90

[0201]

[0202] In Synthesis Example 2, bb-1 and dd-1 were replaced with equimolar amounts of bb-90 and dd-90, respectively, while maintaining the same other steps, yielding compound 90 (17.70 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 830.3688 (theoretical value: 830.3678). Theoretical elemental content (%) C 64 H 34 D7N: C, 92.49; H, 5.82; N, 1.69. Measured elemental content (%): C, 92.50; H, 5.85; N, 1.65.

[0203] Synthesis Example 16: Synthesis of Compound 97

[0204]

[0205] In Synthesis Example 2, aa-1 and dd-1 were replaced with equimolar amounts of aa-97 and dd-97, respectively, while maintaining the same other steps, yielding compound 97 (17.70 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 840.4483 (theoretical value: 840.4492). Theoretical elemental content (%) C 64 H 48 D5N: C, 91.39; H, 6.95; N, 1.67. Measured elemental content (%): C, 91.37; H, 6.96; N, 1.69.

[0206] Synthesis Example 17: Synthesis of Compound 105

[0207]

[0208] In Synthesis Example 2, aa-1, bb-1, and dd-1 were replaced with equimolar amounts of aa-105, bb-105, and dd-97, with all other steps remaining the same, yielding compound 105 (19.29 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 892.4786 (theoretical value: 892.4774). Theoretical elemental content (%) C 68 H 48 D7N: C, 91.44; H, 7.00; N, 1.57. Measured elemental content (%): C, 91.41; H, 7.05; N, 1.54.

[0209] Synthesis Example 18: Synthesis of Compound 123

[0210]

[0211] In Synthesis Example 2, aa-1 and dd-1 were replaced with equimolar amounts of aa-123 and dd-123, respectively, while maintaining the same other steps, to obtain compound 123 (20.10 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 880.3877 (theoretical value: 880.3866). Theoretical elemental content (%) C 68 H 40 D5N: C, 92.69; H, 5.72; N, 1.59. Measured elemental content (%): C, 92.66; H, 5.73; N, 1.58.

[0212] Synthesis Example 19: Synthesis of Compound 130

[0213]

[0214] In Synthesis Example 2, cc-1 and dd-1 were replaced with equimolar amounts of cc-105 and dd-130, with all other steps remaining the same, to obtain compound 130 (19.49 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 914.4629 (theoretical value: 914.4617). Theoretical elemental content (%) C 70 H 46 D7N: C, 91.86; H, 6.61; N, 1.53. Measured elemental content (%): C, 91.87; H, 6.64; N, 1.50.

[0215] Synthesis Example 20: Synthesis of Compound 149

[0216]

[0217] In Synthesis Example 2, aa-1 and dd-1 were replaced with equimolar amounts of aa-149 and dd-149, respectively, with all other steps remaining the same, to obtain compound 149 (19.42 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 937.4599 (theoretical value: 937.4586). Theoretical elemental content (%) C 72 H 51 D4N: C, 92.17; H, 6.34; N, 1.49. Measured elemental content (%): C, 92.19; H, 6.36; N, 1.45.

[0218] Synthesis Example 21: Synthesis of Compound 155

[0219]

[0220] In Synthesis Example 2, cc-1 and dd-1 were replaced with equimolar amounts of cc-149 and dd-155, with all other steps remaining the same, to obtain compound 155 (19.01 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 904.3851 (theoretical value: 904.3866). Theoretical elemental content (%) C 70 H 40 D5N: C, 92.89; H, 5.57; N, 1.55. Measured elemental content (%): C, 92.90; H, 5.58; N, 1.51.

[0221] Synthesis Example 22: Synthesis of Compound 174

[0222]

[0223] In Synthesis Example 2, cc-1 and dd-1 were replaced with equimolar amounts of cc-149 and dd-155, with all other steps remaining the same, to obtain compound 155 (20.07 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 915.4759 (theoretical value: 915.4742). Theoretical elemental content (%) C 70 H 53 D4N: C, 91.76; H, 6.71; N, 1.53. Measured elemental content (%): C, 91.75; H, 6.70; N, 1.56.

[0224] Synthesis Example 23: Synthesis of Compound 191

[0225]

[0226] In Synthesis Example 2, aa-1, bb-1, and dd-1 were replaced with equimolar amounts of aa-191, bb-105, and dd-191, with all other steps remaining the same, yielding compound 191 (17.48 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 808.3823 (theoretical value: 808.3804). Theoretical elemental content (%) C 62 H 32 D9N: C, 92.04; H, 6.23; N, 1.73. Measured elemental content (%): C, 92.06; H, 6.20; N, 1.72.

[0227] Synthesis Example 24: Synthesis of Compound 209

[0228]

[0229] In Synthesis Example 2, cc-1 and dd-1 were replaced with equimolar amounts of cc-97 and dd-209, with all other steps remaining the same, to obtain compound 209 (18.98 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 854.3725 (theoretical value: 854.3709). Theoretical elemental content (%) C 66 H 38 D5N: C, 92.70; H, 5.66; N, 1.64. Measured elemental content (%): C, 92.75; H, 5.63; N, 1.62.

[0230] Synthesis Example 25: Synthesis of Compound 227

[0231]

[0232] In Synthesis Example 2, aa-1, bb-1, and dd-1 were replaced with equimolar amounts of aa-97, bb-227, and dd-227, respectively, with all other steps remaining the same, yielding compound 227 (19.83 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 880.3851 (theoretical value: 880.3866). Theoretical elemental content (%) C 68 H 40 D5N: C, 92.69; H, 5.72; N, 1.59. Measured elemental content (%): C, 92.71; H, 5.70; N, 1.59.

[0233] Synthesis Example 26: Synthesis of Compound 233

[0234]

[0235] In Synthesis Example 2, aa-1, bb-1, and dd-1 were replaced with equimolar amounts of aa-174, bb-227, and dd-233, with all other steps remaining the same, yielding compound 233 (19.12 g). HPLC analysis showed a solid purity ≥ 99.99%. Mass spectrometry m / z: 936.4385 (theoretical value: 936.4399). Theoretical elemental content (%) C 72 H 36 D 11 N: C, 92.27; H, 6.24; N, 1.49. Measured elemental content (%): C, 92.29; H, 6.26; N, 1.45.

[0236] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0237] The following are compounds other than the aromatic amine compounds described in this invention used in the device fabrication examples:

[0238]

[0239] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were measured. The lifespan (brightness decaying to 95% of initial brightness) of the device prepared in this invention was tested using the McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The test results are shown in Tables 1 and 2.

[0240] Comparative device fabrication example 1: Comparative device 1

[0241] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0242] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-1 and p-1 (mass ratio 100:3) as hole injection layer with a thickness of 20 nm; b) HT-1 as hole transport layer with a thickness of 35 nm; c) HTL-1 as light-emitting auxiliary layer with a thickness of 30 nm; d) RH-1, RH-2 and Ir(dpm)(piq)2 (mass ratio 64:32:4) as light-emitting layer with a thickness of 35 nm; e) TPBi as hole blocking layer with a thickness of 25 nm; f) NBphen and Liq (mass ratio 9:1) as electron transport layer with a thickness of 25 nm; g) LiF as electron injection layer with a thickness of 0.1 nm; h) Mg and Ag (mass ratio 3:7) as cathode with a thickness of 10 nm; i) CP-4 as capping layer with a thickness of 120 nm.

[0243] Comparative device fabrication example 2: Comparative device 2

[0244] By replacing HTL-1 in the light-emitting auxiliary layer with HTL-2, and keeping everything else the same as in Comparative Device Preparation Example 1, Comparative Device 2 can be obtained.

[0245] Device fabrication examples 1-25: Light-emitting devices 1-25

[0246] By replacing HTL-1 in the light-emitting auxiliary layer with the aromatic amine compounds of the present invention synthesized in Examples 2 to 26, and keeping everything else the same as in Comparative Device Preparation Example 1, Comparative Devices 1 to 25 can be obtained.

[0247] Table 1

[0248]

[0249]

[0250] Comparative device fabrication example 3: Comparative device 3

[0251] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0252] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-2 and p-1 (mass ratio 100:5) as hole injection layer with a thickness of 25 nm; b) HT-2 as hole transport layer with a thickness of 35 nm; c) BH and BD (mass ratio 96:4) as light-emitting layer with a thickness of 35 nm; d) BAlq as hole blocking layer with a thickness of 25 nm; e) NBphen and Liq (mass ratio 4:1) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 0.1 nm; g) Mg and Ag (mass ratio 5:5) as cathode with a thickness of 10 nm; h) CP-1 as capping layer with a thickness of 110 nm.

[0253] Device fabrication examples 26-50: Light-emitting devices 26-50

[0254] By replacing CP-1 in the capping layer with the aromatic amine compounds of the present invention synthesized in Examples 2 to 26, and with all other steps being the same as in Comparative Device Preparation Example 3, light-emitting devices 26 to 50 can be obtained.

[0255] Table 2

[0256]

[0257]

[0258] The device data in Table 1 show that the aromatic amine compounds described in this invention, when used as a light-emitting auxiliary layer, significantly improve the driving voltage, luminous efficiency, and lifespan of OLED devices. The device data in Table 2 further indicate that they can also be used as a capping layer material in OLED devices, thereby improving the luminous efficiency and lifespan of the devices. In summary, the aromatic amine compounds provided by this invention are a class of high-performance OLED materials with excellent application prospects.

[0259] 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 arylamine compound characterized in that, The arylamine compound has a structure shown in formula (I): The Ar1 is selected from a structure shown in formula (I-A), and the Ar2 is selected from a structure shown in formula (I-B). The a1 is selected from 0, 1, 2, 3, 4 or 5, the b1 is selected from 0, 1, 2, 3 or 4, the a2 is selected from 0, 1, 2, 3 or 4, and the b2 is selected from 0, 1, 2 or 3. The R1 and R2 are selected from a hydrogen atom, an unsubstituted C1-C6 alkyl, an unsubstituted C3-C10 cycloalkyl, and a substituted or unsubstituted phenyl, and two adjacent R1 can be connected to form a substituted or unsubstituted benzene ring. The L1 and L2 are independently selected from a single bond or one of the following structures: wherein said a 41 at each occurrence, is selected from 0, 1, 2, 3, or 4; said b 41 at each occurrence, is selected from 0, 1, 2, or 3; R is selected from the group consisting of hydrogen atom, methyl, isopropyl, tert-butyl; 41 independently at each occurrence, is selected from the group consisting of hydrogen atom, methyl, isopropyl, tert-butyl; The L3 is selected from a single bond or one of the following structures: The substituent in the "substituted or unsubstituted" in the R1 and R2 is selected from an unsubstituted C1-C4 alkyl. When the L3 is a single bond, the Ar3 is selected from one of the following structures: when L3is selected from Ar3is selected from one of the following structures: The deuterium enrichment of formula (I) is less than 50%.

2. The arylamine compound according to claim 1, characterized by The formula (I-A) is selected from one of the structures shown below: wherein said a 11 at each occurrence, the same or different, is selected from 0, 1, 2, 3, 4, or 5; b 11 at each occurrence, the same or different, is selected from 0, 1, 2, 3, or 4; said c 11 at each occurrence, the same or different, is selected from 0, 1, 2, or 3; said d 11 at each occurrence, the same or different, is selected from 0, 1, or 2; R is selected from the group consisting of hydrogen atom, methyl, isopropyl, tert-butyl, and 11 each occurrence is the same or different selected from one of a hydrogen atom, a methyl group, an isopropyl group, a tert-butyl group.

3. The arylamine compound according to claim 1, characterized by The formula (I-B) is selected from one of the following structures: wherein said a 21 at each occurrence, is selected from 0, 1, 2, 3, or 4; said b 21 at each occurrence, is selected from 0, 1, 2, or 3; R is selected from the group consisting of hydrogen atom, methyl, isopropyl, tert-butyl, and 21 each occurrence, is selected from the group consisting of hydrogen atom, methyl, isopropyl, tert-butyl, and 4. The arylamine compound according to claim 1, characterized by Ar3is selected from one of the following structures:

5. The arylamine compound according to claim 1, characterized by L1, L2are independently selected from a single bond or the structure shown below:

6. The arylamine compound according to claim 1, characterized by The L3 is a single bond.

7. An arylamine compound characterized in that, The arylamine compound is selected from one of the following compounds:

8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer comprising at least one of a hole transport region between the anode and the cathode, a light emitting layer, an electron transport region, and a cover layer on the side of the cathode facing away from the anode, characterized in that The organic layer contains one or more arylamine compounds according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole-transporting region. The hole transport region contains one or more arylamine compounds according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a capping layer. The cover layer contains one or more arylamine compounds according to any one of claims 1 to 7.

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