Aromatic amine compound and organic electroluminescent device thereof

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound and an organic electroluminescent device thereof. The aromatic amine compound provided by the invention has proper hole mobility, HOMO and T1 value, has proper charge transfer rate when being applied to an OLED device as a hole transport material, has high energy level matching degree with an adjacent organic matter layer, and effectively improves the luminous efficiency and driving voltage of the device and prolongs the service life of the device. The structure also has good thermal stability and chemical stability, and the service life of the device is further prolonged. The structure can also be used as a covering layer material or a charge generation layer material to be applied to OLED devices.

Description

Technical Field

[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to an aromatic amine compound and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) has the characteristics of light weight, wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity and good flexibility. It has been widely used in the field of lighting and display and is considered by the industry to be one of the most promising display and lighting technologies.

[0003] The classic OLED device has a "sandwich" structure, with a light-emitting layer sandwiched between the cathode and anode electrodes, wherein the light-emitting layer contains a light-emitting substance (guest material). A certain working voltage is applied between the two electrodes, so that holes and electrons are injected from the anode and cathode respectively, and then reach the light-emitting layer, recombine to produce excitons, release energy, and the excitons migrate under the action of the electric field, transfer energy to the light-emitting substance, and the electrons in the molecules of the light-emitting substance transition from the ground state to the excited state. Since the excited state is unstable, the electrons migrate back from the excited state to the ground state, thereby releasing energy in the form of light, generating a light-emitting phenomenon. In order to improve the device performance such as driving voltage, luminous efficiency, color purity, clarity and service life, in general, a hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is provided between the cathode and the light-emitting layer. Among them, the hole transport region mainly plays the role of injecting and transporting holes, and may include one or more layers of the hole injection layer, hole transport layer, light-emitting auxiliary layer, electron blocking layer, etc.; and the electron transport region mainly plays the role of injecting and transporting electrons, and may include one or more layers of the electron injection layer, electron transport layer, hole blocking layer, etc. In order to achieve high luminous efficiency, long service life, low driving voltage, high color purity, etc., each organic layer is required to have an appropriate charge transfer rate, and each organic layer is also required to have a good energy level match. In order to further improve the luminous efficiency, color purity and service life of the device, a covering layer is also set on the outside of the electrode on the light-emitting side (for example, the outside of the cathode of the top-emitting device). At the same time, OLED researchers have also developed a stacked OLED that includes two or more independent light-emitting units connected in series through a charge generation layer (CGL). The electrons and holes generated by the CGL are respectively injected into adjacent light-emitting units, and are compounded into excitons in the light-emitting units to emit light. In addition, n-type doped layers / p-type doped layers are often used as connecting layers between light-emitting units.

[0004] At present, hole transport materials that have good energy level matching with the light-emitting layer materials (guest materials and host materials) used in the industry and have appropriate charge transfer rates are very limited, and covering layer and charge generation layer materials with excellent performance are also relatively limited and urgently need to be developed. Summary of the invention

[0005] In order to solve the above technical problems, the present invention provides an aromatic amine compound, which has appropriate hole mobility, appropriate highest occupied molecular orbital (HOMO) and triplet energy level (T1) values, and excellent thermal stability and chemical stability. It is applied to OLED devices as a hole transport material to improve the driving voltage, luminous efficiency and service life of OLED devices. It has a structure shown in formula (I):

[0006]

[0007] Wherein, each occurrence of a is identically or differently selected from 0, 1, 2, 3 or 4;

[0008] Each time the R appears, it is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring;

[0009] The Ar 1 ,Ar 2 At least one of the following groups is selected from:

[0010]

[0011] Wherein, each time the ring A appears, it is identically or differently selected from one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring;

[0012] Each occurrence of X is the same or different selected from oxygen atoms, sulfur atoms, NR 2 , the R 2Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0013] The a 1 Each time it occurs, it is selected from 0, 1 or 2, either identically or differently;

[0014] The R 1 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0015] Ar not selected from the above groups 1 or Ar 2 One selected from a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring fused monovalent group;

[0016] The Ar 3 Selected from one of the following groups:

[0017]

[0018] Among them, the a 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 2 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 2 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said d 2 Each occurrence is identically or differently selected from 0, 1 or 2; said e 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0019] The R 3 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0020] The R 4 One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0021] The R 5 One selected from substituted or unsubstituted C1-C12 straight chain or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl;

[0022] The R 6 One selected from substituted or unsubstituted C1-C12 straight or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0023] The R 7 One selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring;

[0024] The L 1 Selected from one of the following groups:

[0025]

[0026] Among them, the a 3 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 3 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 3 Each occurrence is identically or differently selected from 0, 1 or 2; said d 3 Each time it occurs, it is selected from 0 or 1 identically or differently; the e 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 3Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0027] The R 8 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0028] The R 9 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0029] The L 2 , L 3 One independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a divalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring;

[0030] The condition is that the R, Ar 1 ~Ar 3 , L 1 ~L 3 At least one of them contains a substituted or unsubstituted silyl group.

[0031] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer contains one or more of the aromatic amine compounds described in the present invention.

[0032] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer on the side of the cathode away from the anode, wherein the covering layer contains one or more of the aromatic amine compounds described in the present invention.

[0033] The present invention also provides a stacked organic electroluminescent device, comprising an anode, a cathode, two or more light-emitting units between the anode and the cathode, and a charge generation layer between each light-emitting unit, wherein the charge generation layer contains one or more of the aromatic amine compounds described in the present invention.

[0034] Beneficial effects:

[0035] The aromatic amine compound provided by the present invention has appropriate hole mobility, HOMO and T1 value. When used as a hole transport material in an OLED device, it has an appropriate charge transfer rate and a high energy level matching degree with the adjacent organic layer, effectively improving the luminous efficiency, driving voltage and service life of the device. The structure also has good thermal stability and chemical stability, further improving the service life of the device. The structure can also be used as a covering layer material or a charge generation layer material in an OLED device. DETAILED DESCRIPTION

[0036] The following will be clearly and completely described in conjunction with the technical solutions of the specific embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0037] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain about 0.0156 atomic % deuterium per hydrogen atom.

[0038] In the present invention, the use of "H" and "hydrogen atom" means that the hydrogen atoms in the chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium atom" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95 atomic % of which is deuterium. "T" and "tritium atom" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, exceeding 10 atomic %, for example, about 95 atomic % of which is tritium. In the present invention, the omitted hydrogen represents "H" or "hydrogen atom".

[0039] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0040] The "silyl group" in the present invention refers to -SiH 3 The “substituted or unsubstituted silyl group” means that one or more H on the silyl group is substituted or unsubstituted by a substituent.

[0041] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing a hydrogen atom in an alkane molecule, which 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 not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0042] The cycloalkyl group of the present invention refers to a hydrocarbon group formed by removing a 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, adamantyl, norbornane, etc., but are not limited thereto. The above cycloalkyl group is preferably cyclopentane, cyclohexane, 1-adamantyl, 2-adamantyl, norbornane.

[0043] The cycloalkenyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloolefin 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 above-mentioned cycloalkenyl group is preferably cyclopentenyl and cyclohexenyl.

[0044] The heterocycloalkyl group described in the present invention refers to a group formed by missing a hydrogen atom from a heterocyclic molecule whose atoms constituting the ring contain at least one heteroatom in addition to carbon atoms. The heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, selenium atoms, phosphorus atoms, etc., preferably nitrogen atoms, oxygen atoms, and sulfur atoms. It preferably contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. It preferably has 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples may include oxirane, thioethane, propylene, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, etc., but are not limited thereto. The above-mentioned heterocyclic group is preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0045] The aromatic group described in the present invention refers to a general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule, which can be a monocyclic aromatic group, a polycyclic aromatic group, a condensed aromatic group or a plurality of other groups, preferably having 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 aromatic group refers to an aromatic group having only one aromatic ring in the molecule, for example, phenyl, etc., but not limited thereto; the polycyclic aromatic group refers to an aromatic group containing two or more independent aromatic rings in the molecule, for example, biphenyl, terphenyl, etc., but not limited thereto; the condensed-ring aromatic group refers to an aromatic group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, naphthyl, anthracenyl, phenanthrenyl, pyrene, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited thereto. The above-mentioned aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0046] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in the aromatic group are replaced by heteroatoms, wherein 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 attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include furanyl, thienyl, pyrrolyl, imidazolyl, pyridyl, pyrimidinyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include phenylfuranyl, phenylthienyl, etc., but are not limited thereto; the condensed ring heteroaryl groups include benzothienyl, benzofuranyl, indolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, etc., but are not limited thereto. The heteroaryl group is preferably a benzothienyl group, a benzofuranyl group, an indolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuranyl group, a dibenzothienyl group, or a pyridyl group.

[0047] The monovalent group formed by the fusion of an aliphatic ring and an aromatic ring of the present invention refers to a general term for a monovalent group after aliphatic rings (cycloalkanes, cycloolefins, cycloalkynes) and aromatic rings are fused together and a hydrogen atom is removed. The aromatic ring 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, which may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, which may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, cycloheptyne. Preferably, examples of the monovalent group formed by the fusion of an aliphatic ring and an aromatic ring may include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited thereto.

[0048] The arylene group described in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0049] The heteroarylene group described in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the heteroaryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0050] The divalent group formed by the fusion of an aliphatic ring and an aromatic ring described in the present invention refers to a group formed by the fusion of an aliphatic ring and an aromatic ring having two bonding sites, that is, a divalent group. The description of the group formed by the fusion of an aliphatic ring and an aromatic ring provided above can be applied to it, except that the divalent group formed by the fusion of an aliphatic ring and an aromatic ring is a divalent group.

[0051] The "substitution" described in the present 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 the substitution is not limited as long as the position is the position where the hydrogen atom is replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0052] The term "substituted or unsubstituted" as used herein means not substituted or substituted by one or more substituents selected from the group consisting of: a deuterium atom, a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C3-C12 cycloalkyl group, a C3-C12 cycloalkenyl group, C3-C12 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, substituted or unsubstituted silyl, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, deuterated isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl substituted cyclopropane, ethyl substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl substituted cyclobutane, ethyl substituted cyclobutane, deuterated cyclobutane, cyclopentane, methyl substituted cyclopropane pentyl, 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, 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 piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, Deuterated anthracenyl, phenanthryl, deuterated phenanthryl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzoxazolyl, benzothiazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triphenylsilyl. When substituted by multiple substituents, the multiple substituents are the same or different from each other, and two adjacent substituents may be connected to form a ring.

[0053] In this specification, when the position of a substituent or a connection site on a ring is not fixed, it means that it can be connected to any of the optional sites of the ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0054] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed Can be expressed And so on.

[0055] The linked ring structure (e.g., a saturated or unsaturated C3-C10 carbon ring, a substituted or unsubstituted saturated or unsaturated C3-C6 aliphatic ring) of the present invention means that the groups are connected to each other by chemical bonds, and optionally form double bonds / triple bonds, and can constitute aromatic groups, as shown in the following examples:

[0056]

[0057] In the present invention, the ring formed by 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 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, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0058] In the present specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0059] The present invention provides an aromatic amine compound having a structure shown in formula (I):

[0060]

[0061] Wherein, each occurrence of a is identically or differently selected from 0, 1, 2, 3 or 4;

[0062] Each time the R appears, it is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring;

[0063] The Ar 1 ,Ar 2 At least one of the following groups is selected from:

[0064]

[0065] Wherein, each time the ring A appears, it is identically or differently selected from one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring;

[0066] Each occurrence of X is the same or different selected from oxygen atoms, sulfur atoms, NR 2 , the R 2 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0067] The a 1 Each time it occurs, it is selected from 0, 1 or 2, either identically or differently;

[0068] The R 1 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0069] Ar not selected from the above groups 1 or Ar 2One selected from a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring fused monovalent group;

[0070] The Ar 3 Selected from one of the following groups:

[0071]

[0072] Among them, the a 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 2 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 2 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said d 2 Each occurrence is identically or differently selected from 0, 1 or 2; said e 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 2 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0073] The R 3 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0074] The R 4 One selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0075] The R 5 One selected from substituted or unsubstituted C1-C12 straight chain or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl;

[0076] The R 6One selected from substituted or unsubstituted C1-C12 straight or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0077] The R 7 One selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, and a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring;

[0078] The L 1 Selected from one of the following groups:

[0079]

[0080] Among them, the a 3 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 3 Each time it occurs, it is selected from 0, 1, 2 or 3 identically or differently; 3 Each occurrence is identically or differently selected from 0, 1 or 2; said d 3 Each time it occurs, it is selected from 0 or 1 identically or differently; the e 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 3 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0081] The R 8 Each occurrence is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group;

[0082] The R 9 Each occurrence is the same or different and is selected from one of the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, and a substituted or unsubstituted silyl group;

[0083] The L 2, L 3 One independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, and a divalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring;

[0084] The condition is that the R, Ar 1 ~Ar 3 , L 1 ~L 3 At least one of them contains a substituted or unsubstituted silyl group.

[0085] Preferably, the substituents in the "substituted or unsubstituted" are independently selected from one of the following groups: a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 aliphatic ring fused with a C6-C30 aromatic ring, a substituted or unsubstituted silyl group, and the substituents are one or more. When there are multiple substituents, the multiple substituents are the same or different. When there are multiple substituents, two adjacent substituents can be connected to form a substituted or unsubstituted saturated or unsaturated C3-C7 carbocyclic ring.

[0086] Preferably, the substituent in the "substituted or unsubstituted" is independently selected from one of the following groups: deuterium atom; fluorine atom; cyano group; methyl substituted or unsubstituted by deuterium atom or fluorine atom; ethyl; n-propyl group; isopropyl group substituted or unsubstituted by deuterium atom or fluorine atom; n-butyl group; sec-butyl group; isobutyl group; tert-butyl group substituted or unsubstituted by deuterium atom or fluorine atom; cyclopropane group; cyclobutane group; cyclopentane group; cyclohexane group; the following groups substituted or unsubstituted by one or more of deuterium atom, methyl, ethyl, isopropyl and tert-butyl group: adamantyl group and norbornyl group; the following groups substituted or unsubstituted by one or more of deuterium atom, fluorine atom, cyano group, methyl, ethyl, isopropyl, tert-butyl, adamantyl and norbornyl group: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene group, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spiro Difluorenyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, N-phenylcarbazolyl, benzocyclopentyl, benzocyclohexyl; silyl substituted or unsubstituted by one or more of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, fluorine atom-substituted phenyl, cyano-substituted phenyl, adamantyl-substituted phenyl, norbornyl-substituted phenyl, naphthyl, deuterated naphthyl, anthracenyl, phenanthryl, biphenyl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothienyl, 9,9-dimethylfluorenyl, wherein the substituent is one or more, and when the substituent is multiple, the multiple substituents are the same or different, and when the substituent is multiple, two adjacent substituents can be connected to form a substituted or unsubstituted saturated or unsaturated C3~C6 carbon ring.

[0087] Preferably, the R, Ar 1 ~Ar 3 At least one of them contains a substituted or unsubstituted silyl group.

[0088] Preferably, the Ar 1 ~Ar 3 At least one of them contains a substituted or unsubstituted silyl group.

[0089] Preferably, the Ar 1 ,Ar 2 or Ar 3 Contains substituted or unsubstituted silyl group.

[0090] Preferably, the Ar 3 Contains substituted or unsubstituted silyl group.

[0091] Preferably, the number of substituted or unsubstituted silyl groups in the aromatic amine compound is 1, 2, 3, 4 or more.

[0092] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k ) 3 A group in which each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms in the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms in the aryl group is preferably 6 to 20, preferably 6 to 13, more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R k The same or different radicals are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropane, substituted or unsubstituted cyclobutane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the substituted silyl group specifically includes trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, isopropyldimethylsilyl, vinyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, naphthyldiphenylsilyl, dibenzofuranyldiphenylsilyl, dibenzothienyldiphenylsilyl, 9,9-dimethylfluorenyldiphenylsilyl, etc., but is not limited thereto. The above-mentioned substituted silyl group is preferably trimethylsilyl, triethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl.

[0093] Preferably, the R is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group, a benzocyclopentyl group, a benzocyclohexyl group, and a silyl group, and two adjacent R groups can be connected to form a ring;

[0094] Preferably, the Ar 1 ,Ar 2 At least one of the following groups is selected from:

[0095]

[0096] Among them, the a 11 Each time it occurs, it is selected from 0, 1 or 2 identically or differently; 11 Each time it occurs, it is selected from 0, 1, 2 or 3 identically or differently; 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said d 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said e 11 Each time it occurs, it is selected from 0, 1, 2, 3 or 4 identically or differently; said f 11 Each time it occurs, it is selected from 0 or 1, either identically or differently;

[0097] Each occurrence of X is the same or different selected from oxygen atoms, sulfur atoms, NR 21 , the R 21 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, silyl;

[0098] The R 11Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, silyl;

[0099] Ar not selected from the above groups 1 or Ar 2 Selected from one of the following groups:

[0100]

[0101] Among them, the a 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 12 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 12 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said d 12 Each occurrence is identically or differently selected from 0, 1 or 2; said e 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0102] The R 12 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, a fluorenyl group, a benzocyclopentyl group, a benzocyclohexyl group, a silyl group, and two adjacent R 12 They may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring;

[0103] The R 13Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: one of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and silyl;

[0104] The R 14 A substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane;

[0105] The R 15 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl;

[0106] The R 16 A substituted or unsubstituted group selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl and benzocyclohexyl.

[0107] Preferably, the Ar 1 ,Ar 2 At least one of the following groups is selected from:

[0108]

[0109] Ar not selected from the above groups 1 or Ar 2 Selected from one of the following groups:

[0110]

[0111]

[0112] Preferably, the R 3Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, silyl, and two adjacent R 3 They may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring;

[0113] Preferably, the R 4 A hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, an adamantyl group, a norbornyl group, and a silyl group;

[0114] Preferably, the R 5 A substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane;

[0115] Preferably, the R 6 A substituted or unsubstituted group selected from the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl;

[0116] Preferably, the R 7 A substituted or unsubstituted group selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl and benzocyclohexyl.

[0117] Preferably, the Ar 3 Selected from one of the following groups:

[0118]

[0119] Among them, the R k At each occurrence, it is identically or differently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C2-C60 heteroaryl.

[0120] Preferably, the R k At each occurrence, it is identically or differently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0121] Preferably, the R k Each occurrence is identically or differently selected from one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl.

[0122] Preferably, the R k Each occurrence is identically or differently selected from one of the following groups: methyl, deuterated methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, adamantyl, norbornyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, pyridyl, pyrimidinyl, dibenzofuranyl, deuterated dibenzofuranyl, dibenzothienyl, deuterated dibenzothienyl, 9,9-dimethylfluorenyl, deuterated 9,9-dimethylfluorenyl.

[0123] Preferably, the -Si(R k ) 3 Each occurrence is identically or differently selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, isopropyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl and the like.

[0124] Preferably, the R 8Each time it occurs, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, and silyl.

[0125] Preferably, the R 9 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and a silyl group.

[0126] The L 1 Selected from one of the following groups:

[0127]

[0128] Preferably, the L 2 , L 3 Independently selected from a single bond, a group as shown below, or a combination thereof:

[0129]

[0130] Among them, the a 101 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 101 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 101 Each occurrence is identically or differently selected from 0, 1 or 2; said d 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0131] The R 101Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a fluorenyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a benzocyclopentyl group, a benzocyclohexyl group, a silyl group;

[0132] The R 102 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and a silyl group.

[0133] Preferably, the L 2 , L 3 Independently selected from a single bond, a group as shown below, or a combination thereof:

[0134]

[0135] Preferably, the aromatic amine compound has one of the structures shown below:

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] The above lists only some specific structural forms of the aromatic amine compounds described in the present invention, but the present invention is not limited to these chemical structures listed, and all those based on formula (I) and with substituents as defined in the present invention should be included.

[0148] The aromatic amine compound of the present invention can be prepared by one of the following synthetic routes:

[0149] Synthesis route 1:

[0150]

[0151] Synthesis route 2:

[0152]

[0153] Synthesis route three:

[0154]

[0155] In the above-mentioned synthetic routes, the X 1 is, at each occurrence, identically or differently selected from a chlorine atom, a bromine atom or an iodine atom;

[0156] The R and Ar 1 ~Ar 3 , L 1 ~L 3 , a are as described in the present invention.

[0157] In each of the above-mentioned synthetic routes, the aromatic amine compound of the present invention can be obtained by a CN coupling reaction between the secondary amine compound (M) and the halide (Y).

[0158] The above reaction route adopts the reaction type commonly used in organic synthesis, and the reaction conditions (for example, the selection of types of reaction solvents, catalysts, ligands, bases, etc., the amount used, and the order and method of addition) are not particularly limited. The above preparation method has easy-to-obtain raw materials, a simple preparation process, and excellent yield. The present invention can also be synthesized using conventional reaction types in other organic syntheses without particular restrictions, and the above is only an example of a synthetic route.

[0159] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer contains one or more of the aromatic amine compounds described in the present invention. Preferably, the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, wherein the hole transport region contains one or more of the aromatic amine compounds described in the present invention. Preferably, the organic electroluminescent device further comprises a covering layer on the side of the cathode facing away from the anode.

[0160] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer on the side of the cathode away from the anode, wherein the covering layer contains one or more of the aromatic amine compounds described in the present invention.

[0161] The present invention also provides a stacked organic electroluminescent device, comprising an anode, a cathode, two or more light-emitting units between the anode and the cathode, and a charge generation layer between each light-emitting unit, wherein the charge generation layer contains one or more of the aromatic amine compounds described in the present invention. Preferably, the charge generation layer comprises an electron generation layer and a hole generation layer, wherein the hole generation layer contains one or more of the aromatic amine compounds described in the present invention.

[0162] The hole transport region of the present invention includes at least one layer of a hole injection layer, a hole transport layer and a light-emitting auxiliary layer.

[0163] The hole injection layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer 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 may be used, for example, 4,4',4"-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (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), compounds HT-1 to HT-19, compounds p-1 to p-3, and aromatic amine compounds of the present invention, but are not limited thereto.

[0164]

[0165] The hole transport layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. A triarylamine compound may be used, or other materials with a hole mobility of 10 -6 cm 2 / Vs or above, for example, 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), the compounds HT-1 to HT-19 shown above, and the aromatic amine compounds described in the present invention, but are not limited thereto.

[0166] The light-emitting auxiliary layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, and other substances with appropriate HOMO and T1 energy levels may be used. Examples include TPD, NPB, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1 ,1'-biphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, the compounds HT-1 to HT-19 shown above, and the aromatic amine compounds described in the present invention, but are not limited thereto.

[0167] The light-emitting layer of the present invention includes a guest material and a host material, and a dual host material formed of two host materials may be used. The guest material may be a fluorescent compound such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, and the like. Examples thereof include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazole vinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), and the like. Phosphorescent materials may also be used, such as metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples thereof include bis(4,6-difluorophenylpyridine-N,C2)picolinyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ), bis(2-phenylpyridinium) acetylacetonate (Ir(ppy) 2 The host material preferably uses a substance having a higher LUMO and a lower HOMO than the guest material, such as a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative, a benzoxazole derivative, a benzothiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and examples thereof include Alq 3, BAlq, TPBI, TPD, 4,4'-di(9-carbazole)biphenyl (CBP), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(2-naphthyl)anthracene (ADN), but are not limited thereto.

[0168] The electron transport region of the present invention comprises at least one layer of an electron injection layer, an electron transport layer and a hole blocking layer.

[0169] The electron injection layer of the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. One or more of the following substances can be selected: 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, CaF 2 、BaO、Li 2 CO 3 、CaCO 3 , Li 2 C 2 O 4 , Cs 2 C 2 O 4 , CsAlF 4 , LiOx, Yb, Tb, etc., but not limited to these.

[0170] The electron transport layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, polymer compounds, etc. with high electron transport properties may be used. Examples include 8-hydroxyquinoline aluminum (Alq 3 ), bis(10-hydroxybenzo[h]quinolinolato)beryllium (BeBq 2 ), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited thereto.

[0171] The hole blocking layer of the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The selected material requires a T1 energy level higher than the light-emitting layer, so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material must be lower than the HOMO energy level of the main material of the light-emitting layer, so as to play a role in blocking holes. Furthermore, the electron mobility of the hole blocking layer material used is 10 -6 cm 2 / Vs or more, which is conducive to the transmission of electrons. One or more of the following substances can be selected: aluminum complex, lithium complex, beryllium complex, oxazole derivative, benzoxazole derivative, thiazole derivative, benzothiazole derivative, imidazole derivative, benzimidazole derivative, phenanthroline derivative, polymer compound, etc. Examples include 1,3,5-tris(1-phenyl-1H-benzimidazole-2-yl)benzene (TPBI), BAlq, etc., but are not limited thereto.

[0172] The anode of the present invention can be a reflective anode, such as a reflective film formed by silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb) or their alloys, or a transparent or translucent layer structure with a high work function, such as indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In 2 O 3 ) or tin oxide (SnO 2 ) is formed according to the type of device to be prepared. For example, if the device to be prepared is a bottom-emitting device (emitting light on the anode side), a transparent or translucent anode needs to be made; if the device to be prepared is a top-emitting device (emitting light on the cathode side), a reflective anode needs to be made.

[0173] The cathode described in the present 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., and can be made into a reflective electrode, a transparent electrode or a semi-transparent electrode by adjusting the thickness of the film. If a bottom-emitting device is to be prepared, a reflective cathode needs to be made. If a top-emitting device is to be prepared, a transparent or semi-transparent cathode needs to be made.

[0174] The cover layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The cover layer material may be an organic or inorganic substance with an appropriate refractive index, such as a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic compound, heteroaromatic compound, aromatic amine compound, etc. Examples include LiF, CsF, MgF 2 , CaF 2 、CsCl、CuI、V2 O 5 , WO 3 、MoO 3 、TiO 2 、ZrO、ZnO、SiO 2 、SiN、ZnS、Alq 3 , compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compounds described in the present invention, but not limited thereto.

[0175]

[0176] The electron generation layer of the present invention includes a main material and a doping material, wherein the doping material is generally a transition metal such as ytterbium or an alkali metal or alkaline earth metal such as lithium and magnesium, and the main material is mostly an electron transport material, such as a phenanthroline derivative, but not limited thereto.

[0177] The hole generating layer described in the present invention comprises a main material and a doping material, wherein the doping material is generally a cyclic olefin compound, such as the above-mentioned compounds p-1 to p-3, and the main material is mostly an aromatic amine compound, such as the above-mentioned compounds HT-1 to HT-19 and the aromatic amine compound described in the present invention, but is not limited thereto.

[0178] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and the hole injection layer contains one or more of the aromatic amine compounds described in the present invention.

[0179] Preferably, the hole transport region comprises a hole injection layer and a hole transport layer, and the hole transport layer contains one or more of the aromatic amine compounds described in the present invention.

[0180] Preferably, the hole transport region comprises a hole injection layer and a hole transport layer, and the hole injection layer and the hole transport layer both contain one or more of the aromatic amine compounds described in the present invention.

[0181] Preferably, the hole transport region includes a hole injection layer, a hole transport layer and a light-emitting auxiliary layer, and the hole injection layer contains one or more of the aromatic amine compounds described in the present invention.

[0182] Preferably, the hole transport region includes a hole injection layer, a hole transport layer and a light-emitting auxiliary layer, and the hole transport layer contains one or more of the aromatic amine compounds described in the present invention.

[0183] Preferably, the hole transport region includes a hole injection layer, a hole transport layer and a luminescence auxiliary layer, and the luminescence auxiliary layer contains one or more of the aromatic amine compounds described in the present invention.

[0184] Preferably, the hole transport region comprises a hole injection layer, a hole transport layer and a light-emitting auxiliary layer, and the hole injection layer and the hole transport layer both contain one or more of the aromatic amine compounds described in the present invention.

[0185] The above-mentioned organic layers, cathode, and anode can be prepared by any method including vacuum evaporation, inkjet printing, sputtering, plasma, ion plating, spin coating, dipping, screen printing, etc. There is no special restriction on the thickness of each layer as long as good device performance is obtained.

[0186] The above-mentioned organic layers are preferably prepared by vacuum evaporation, inkjet printing or spin coating.

[0187] The thickness of each organic layer is usually 5 nm to 100 um, preferably 10 nm to 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0188] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, VR, and car taillights.

[0189] The technical scheme and technical effects of the present invention are further illustrated below with reference to embodiments and comparative examples.

[0190] The mass spectra of the compounds of the present invention were determined using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, with chloroform as the solvent;

[0191] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0192] Synthesis Example 1: Synthesis of Intermediate DD

[0193] Synthesis of intermediate DD-17:

[0194]

[0195] Add magnesium powder (1.22 g, 50 mmol) to the reaction flask, add dropwise 100 mL of dry diethyl ether solution containing compound bb-17 (11.66 g, 50 mmol), and reflux the solution slowly for 3 h to prepare the corresponding Grignard reagent. Slowly add 110 mL of dry diethyl ether solution containing compound aa-17 (18.33 g, 55 mmol) to the Grignard reagent and reflux overnight. After the reaction is completed, cool to room temperature, filter the deposited precipitate by suction, and wash with cold ether. Stir the obtained solid in an ice-cold saturated aqueous ammonium chloride solution for 2 h, collect the precipitate, and dry it in vacuum. Dissolve the obtained solid in boiling acetic acid (110 mL), and add concentrated HCl (0.5 mL) dropwise to solidify the mixture. Filter out the crude product and use CHCl 3 / EtOH recrystallization to obtain intermediate DD-17 (19.48 g, yield 83%), solid purity ≥ 99.83% detected by HPLC. Mass spectrum m / z: 468.0923 (theoretical value: 468.0909).

[0196] By replacing the raw materials accordingly and following the synthesis method of intermediate DD-17, other intermediates DD can be obtained, as shown in the following table:

[0197]

[0198] Synthesis Example 2: Synthesis of Intermediate AA / BB

[0199] Synthesis of intermediate BB-257:

[0200]

[0201] Under argon atmosphere, aa'-257 (12.12 g, 60 mmol), bb'-257 (7.82 g, 50 mmol), Pd(PPh 3 ) 4 (0.23g, 0.2mmol), potassium carbonate aqueous solution (14.51g, 105mmol), toluene (370mL), reflux for 24 hours. After the reaction is completed, cool to room temperature, add water to quench the reaction, extract with dichloromethane, combine the organic phases, dry the organic phase with anhydrous magnesium sulfate, filter, rotary evaporate the filtrate, and purify it on a silica gel column (dichloromethane: petroleum ether = 1:1) to obtain BB-257 (10.05g, 86%); HPLC purity ≥99.87%. Mass spectrum m / z: 233.0644 (theoretical value: 233.0656).

[0202] By replacing the raw materials accordingly and following the synthesis method of intermediate BB-257, other intermediates AA / BB can be obtained, as shown in the following table:

[0203]

[0204]

[0205] Synthesis of intermediate BB-431:

[0206]

[0207] Under nitrogen protection, cc-431 (7.58 g, 50 mmol), aa'-324 (13.75 g, 60 mmol), copper powder (0.42 g, 6.5 mmol), 18-crown-6 (0.13 g, 0.5 mmol), K 2 CO 3 (0.83 g, 6 mmol), DMF (25 mL), stirred under reflux for 20 hours. After the reaction was completed, cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was washed with water, dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain intermediate BB-431 (11.55 g, 77%); HPLC detected the solid purity ≧99.85%. Mass spectrum m / z: 299.0881 (theoretical value: 299.0897).

[0208] Synthesis Example 3: Synthesis of Compound 17

[0209]

[0210] Under nitrogen protection, AA-17 (5.08 g, 30 mmol), BB-17 (5.91 g, 30 mmol), Pd(OAc) were added to the reaction bottle. 2 (0.07 g, 0.3 mmol), P(t-Bu) 3 (1.2mL of 0.5M toluene solution, 0.6mmol), sodium tert-butoxide (5.77g, 60mmol), toluene (270mL), stir the mixture, and heat under reflux for 5h. After the reaction is completed, cool to room temperature, add distilled water to wash the mixture, then extract with dichloromethane, stand and separate, collect the organic phase and dry it with anhydrous magnesium sulfate, cool and crystallize, filter, and recrystallize the obtained residue with toluene / methanol (volume ratio 9:1) to obtain intermediate CC-17 (7.62g, 89%). The solid purity is ≥99.88% by HPLC. Mass spectrum m / z: 285.1169 (theoretical value: 285.1154).

[0211] Under nitrogen protection, CC-17 (2.85 g, 10 mmol), DD-17 (4.69 g, 10 mmol), Pd 2 (dba) 3(0.09 g, 0.1 mmol), P(t-Bu) 3 (0.4mL of 0.5M toluene solution, 0.2mmol), sodium tert-butoxide (1.92g, 20mmol), toluene (100mL), stir the mixture, and heat under reflux for 6.5h. After the reaction is completed, cool to room temperature, wash the mixture with distilled water, extract with dichloromethane, stand and separate, collect the organic phase and dry it with anhydrous magnesium sulfate, cool and crystallize, filter, and recrystallize the residue with toluene to obtain compound 17 (5.66g, 84%). The solid purity is ≥99.99% by HPLC. Mass spectrum m / z: 673.2818 (theoretical value: 673.2801). Theoretical element content (%) C 48 H 39 NOSi: C, 85.55; H, 5.83; N, 2.08. Measured element content (%): C, 85.58; H, 5.78; N, 2.09.

[0212] Synthesis Example 4: Synthesis of Compound 24

[0213]

[0214] AA-17 was replaced by an equal molar amount of AA-24, and BB-17 was replaced by an equal molar amount of BB-24. The other steps were the same as those in Synthesis Example 3 to obtain Compound 24 (6.21 g, yield 80%). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 775.3284 (theoretical value: 775.3270). Theoretical element content (%) C 56 H 45 NOSi: C, 86.67; H, 5.84; N, 1.80. Measured element content (%): C, 86.66; H, 5.89; N, 1.78.

[0215] Synthesis Example 5: Synthesis of Compound 47

[0216]

[0217] AA-17 was replaced by an equal molar amount of AA-47, and BB-17 was replaced by an equal molar amount of BB-47. The other steps were the same as those in Synthesis Example 3 to obtain Compound 47 (6.23 g, yield 83%). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 749.3126 (theoretical value: 749.3114). Theoretical element content (%) C54H43NOSi: C, 86.48; H, 5.78; N, 1.87. Measured element content (%): C, 86.45; H, 5.75; N, 1.91.

[0218] Synthesis Example 6: Synthesis of Compound 53

[0219]

[0220] AA-17 was replaced by an equal molar amount of AA-53, and BB-17 was replaced by an equal molar amount of BB-47. The other steps were the same as those in Synthesis Example 3 to obtain Compound 53 (6.40 g, yield 81%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 789.3435 (theoretical value: 789.3427). Theoretical element content (%) C 57 H 47 NOSi: C, 86.65; H, 6.00; N, 1.77. Measured element content (%): C, 86.67; H, 6.04; N, 1.73.

[0221] Synthesis Example 7: Synthesis of Compound 123

[0222]

[0223] AA-17 was replaced by an equal molar amount of AA-53, BB-17 was replaced by an equal molar amount of BB-47, and DD-17 was replaced by an equal molar amount of DD-123. The other steps were the same as those in Synthesis Example 3 to obtain Compound 123 (6.56 g, yield 83%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 789.3415 (theoretical value: 789.3427). Theoretical element content (%) C 57 H 47 NOSi: C, 86.65; H, 6.00; N, 1.77. Measured element content (%): C, 86.68; H, 6.05; N, 1.71.

[0224] Synthesis Example 8: Synthesis of Compound 129

[0225]

[0226] AA-17 was replaced by an equal molar amount of AA-47, BB-17 was replaced by an equal molar amount of BB-129, and DD-17 was replaced by an equal molar amount of DD-123. The other steps were the same as those in Synthesis Example 3 to obtain Compound 129 (6.44 g, yield 84%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 765.2897 (theoretical value: 765.2885). Theoretical element content (%) C 54 H 43NSSi: C, 84.66; H, 5.66; N, 1.83. Measured element content (%): C, 84.69; H, 5.61; N, 1.84.

[0227] Synthesis Example 9: Synthesis of Compound 190

[0228]

[0229] AA-17 was replaced by an equal molar amount of AA-24, BB-17 was replaced by an equal molar amount of BB-190, and DD-17 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 3 to obtain Compound 190 (5.46 g, yield 81%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 673.2816 (theoretical value: 673.2801). Theoretical element content (%) C 48 H 39 NOSi: C, 85.55; H, 5.83; N, 2.08. Measured element content (%): C, 85.59; H, 5.80; N, 2.09.

[0230] Synthesis Example 10: Synthesis of Compound 193

[0231]

[0232] AA-17 was replaced by an equal molar amount of AA-193, BB-17 was replaced by an equal molar amount of BB-190, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 193 (6.15 g, yield 82%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 749.3128 (theoretical value: 749.3114). Theoretical element content (%) C 54 H 43 NOSi: C, 86.48; H, 5.78; N, 1.87. Measured element content (%): C, 86.49; H, 5.72; N, 1.90.

[0233] Synthesis Example 11: Synthesis of Compound 237

[0234]

[0235] AA-17 was replaced by an equal molar amount of AA-237, BB-17 was replaced by an equal molar amount of BB-237, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 237 (5.12 g, yield 79%). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 647.2660 (theoretical value: 647.2644). Theoretical element content (%) C 46 H 37 NOSi: C, 85.28; H, 5.76; N, 2.16. Measured element content (%): C, 85.25; H, 5.74; N, 2.18.

[0236] Synthesis Example 12: Synthesis of Compound 246

[0237]

[0238] AA-17 was replaced by an equal molar amount of AA-237, BB-17 was replaced by an equal molar amount of BB-246, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 246 (5.73 g, yield 85%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 673.2819 (theoretical value: 673.2801). Theoretical element content (%) C 48 H 39 NOSi: C, 85.55; H, 5.83; N, 2.08. Measured element content (%): C, 85.53; H, 5.89; N, 2.05.

[0239] Synthesis Example 13: Synthesis of Compound 257

[0240]

[0241] AA-17 was replaced by an equal molar amount of AA-237, BB-17 was replaced by an equal molar amount of BB-257, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 257 (5.84 g, yield 86%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 678.3128 (theoretical value: 678.3115). Theoretical element content (%) C 48 H 34 D 5 NOSi: C, 84.91; H, 6.53; N, 2.06. Measured element content (%): C, 84.96; H, 6.50; N, 2.05.

[0242] Synthesis Example 14: Synthesis of Compound 259

[0243]

[0244] AA-17 was replaced by an equal molar amount of AA-259, BB-17 was replaced by an equal molar amount of BB-259, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 259 (5.73 g, yield 80%). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 715.3279 (theoretical value: 715.3270). Theoretical element content (%) C 51 H 45 NOSi: C, 85.55; H, 6.34; N, 1.96. Measured element content (%): C, 85.52; H, 6.39; N, 1.94.

[0245] Synthesis Example 15: Synthesis of Compound 266

[0246]

[0247] AA-17 was replaced by an equal molar amount of AA-266, BB-17 was replaced by an equal molar amount of BB-266, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 266 (6.97 g, yield 81%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 859.3285 (theoretical value: 859.3270). Theoretical element content (%) C 63 H 45 NOSi: C, 87.97; H, 5.27; N, 1.63. Measured element content (%): C, 87.98; H, 5.24; N, 1.64.

[0248] Synthesis Example 16: Synthesis of Compound 272

[0249]

[0250] AA-17 was replaced by an equal molar amount of AA-266, BB-17 was replaced by an equal molar amount of BB-190, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 272 (6.45 g, yield 86%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 749.3124 (theoretical value: 749.3114). Theoretical element content (%) C 54 H 43NOSi: C, 86.48; H, 5.78; N, 1.87. Measured element content (%): C, 86.46; H, 5.76; N, 1.90.

[0251] Synthesis Example 17: Synthesis of Compound 324

[0252]

[0253] AA-17 was replaced by an equal molar amount of AA-324, BB-17 was replaced by an equal molar amount of BB-324, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 324 (6.95 g, yield 84%). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 826.3364 (theoretical value: 826.3379). Theoretical element content (%) C 59 H 46 N 2 OSi: C, 85.68; H, 5.61; N, 3.39. Measured element content (%): C, 85.69; H, 5.64; N, 3.38.

[0254] Synthesis Example 18: Synthesis of Compound 364

[0255]

[0256] AA-17 was replaced by an equal molar amount of AA-364, BB-17 was replaced by an equal molar amount of aa'-404, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 364 (6.29 g, yield 85%). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 739.2741 (theoretical value: 739.2729). Theoretical element content (%) C 52 H 41 NSSi: C, 84.40; H, 5.58; N, 1.89. Measured element content (%): C, 84.44; H, 5.56; N, 1.87.

[0257] Synthesis Example 19: Synthesis of Compound 378

[0258]

[0259] AA-17 was replaced by an equal molar amount of AA-378, BB-17 was replaced by an equal molar amount of BB-378, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 378 (5.80 g, yield 84%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 689.2585 (theoretical value: 689.2572). Theoretical element content (%) C 48 H 39 NSSi: C, 83.56; H, 5.70; N, 2.03. Measured element content (%): C, 83.53; H, 5.75; N, 2.04.

[0260] Synthesis Example 20: Synthesis of Compound 381

[0261]

[0262] AA-17 was replaced by an equal molar amount of AA-381, BB-17 was replaced by an equal molar amount of BB-381, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 381 (6.02 g, yield 79%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 761.2983 (theoretical value: 761.2968). Theoretical element content (%) C 51 H 47 NSSi 2 :C, 80.37;H, 6.22;N, 1.84. Measured element content (%): C, 80.36;H, 6.25;N, 1.82.

[0263] Synthesis Example 21: Synthesis of Compound 386

[0264]

[0265] AA-17 was replaced by an equal molar amount of AA-381, BB-17 was replaced by an equal molar amount of BB-386, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 386 (5.99 g, yield 81%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 739.2746 (theoretical value: 739.2729). Theoretical element content (%) C 52 H 41 NSSi: C, 84.40; H, 5.58; N, 1.89. Measured element content (%): C, 84.43; H, 5.52; N, 1.91.

[0266] Synthesis Example 22: Synthesis of Compound 390

[0267]

[0268] AA-17 was replaced by an equal molar amount of AA-390, BB-17 was replaced by an equal molar amount of BB-390, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 390 (6.62 g, yield 86%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 769.3154 (theoretical value: 769.3137). Theoretical element content (%) C 54 H 39 D 4 NSSi: C, 84.22; H, 6.15; N, 1.82. Measured element content (%): C, 84.26; H, 6.12; N, 1.80.

[0269] Synthesis Example 23: Synthesis of Compound 404

[0270]

[0271] AA-17 was replaced by an equal molar amount of AA-404, BB-17 was replaced by an equal molar amount of BB-404, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 404 (6.69 g, yield 83%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 805.3185 (theoretical value: 805.3198). Theoretical element content (%) C 57 H 47 NSSi: C, 84.92; H, 5.88; N, 1.74. Measured element content (%): C, 84.87; H, 5.92; N, 1.77.

[0272] Synthesis Example 24: Synthesis of Compound 410

[0273]

[0274] AA-17 was replaced by an equal molar amount of AA-410, BB-17 was replaced by an equal molar amount of BB-190, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 410 (6.02 g, yield 77%). The solid purity was ≥ 99.90% by HPLC. Mass spectrum m / z: 781.2959 (theoretical value: 781.2947). Theoretical element content (%) C 53 H 43 N 3SSi: C, 81.39; H, 5.54; N, 5.37. Measured element content (%): C, 81.36; H, 5.59; N, 5.35.

[0275] Synthesis Example 25: Synthesis of Compound 431

[0276]

[0277] AA-17 was replaced by an equal molar amount of AA-47, BB-17 was replaced by an equal molar amount of BB-431, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 431 (5.84 g, yield 78%). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 748.3286 (theoretical value: 748.3274). Theoretical element content (%) C 54 H 44 N 2 Si: C, 86.59; H, 5.92; N, 3.74. Measured element content (%): C, 86.57; H, 5.98; N, 3.70.

[0278] Synthesis Example 26: Synthesis of Compound 442

[0279]

[0280] AA-17 was replaced by an equal molar amount of AA-324, BB-17 was replaced by an equal molar amount of BB-442, and DD-17 was replaced by an equal molar amount of DD-193. The other steps were the same as those in Synthesis Example 3 to obtain Compound 442 (6.77 g, yield 82%). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 824.3571 (theoretical value: 824.3587). Theoretical element content (%) C 60 H 48 N 2 Si: C, 87.34; H, 5.86; N, 3.40. Measured element content (%): C, 87.37; H, 5.83; N, 3.39.

[0281] Synthesis Example 27: Synthesis of Compound 493

[0282]

[0283] AA-17 was replaced by an equal molar amount of AA-237, and BB-17 was replaced by an equal molar amount of BB-47. The other steps were the same as those in Synthesis Example 3 to obtain Compound 493 (6.19 g, yield 83%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 745.3178 (theoretical value: 745.3196). Theoretical element content (%) C 51 H 47 NOS 2 :C, 82.10;H, 6.35;N, 1.88. Measured element content (%): C, 82.16;H, 6.32;N, 1.84.

[0284] Synthesis Example 28: Synthesis of Compound 495

[0285]

[0286] AA-17 was replaced by an equal molar amount of AA-324, BB-17 was replaced by an equal molar amount of BB-190, and DD-17 was replaced by an equal molar amount of DD-495. The other steps were the same as those in Synthesis Example 3 to obtain Compound 495 (6.74 g, yield 82%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 821.3521 (theoretical value: 821.3509). Theoretical element content (%) C 57 H 51 NOS 2 :C, 83.27;H, 6.25;N, 1.70. Measured element content (%): C, 83.23;H, 6.27;N, 1.75.

[0287] Synthesis Example 29: Synthesis of Compound 498

[0288]

[0289] AA-17 was replaced by an equal molar amount of AA-53, BB-17 was replaced by an equal molar amount of BB-47, and DD-17 was replaced by an equal molar amount of DD-495. The other steps were the same as those in Synthesis Example 3 to obtain Compound 498 (6.40 g, yield 81%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 789.3411 (theoretical value: 789.3427). Theoretical element content (%) C 57 H 47 NOSi: C, 86.65; H, 6.00; N, 1.77. Measured element content (%): C, 86.62; H, 6.08; N, 1.74.

[0290] The following are other compounds used in the device preparation examples except the aromatic amine compound described in the present invention:

[0291]

[0292] The test software, computer, K2400 digital source meter of Keithley Company and PR788 spectrum scanning luminance meter of Photo Research Company were combined into a combined IVL test system. The device prepared by the present invention was tested at a current density of 15 mA / cm at atmospheric pressure and room temperature. 2 The luminous efficiency and driving voltage at the time of the device are measured. The life of the device prepared by the present invention is tested at atmospheric pressure and room temperature using the M6000 OLED life test system of McScience Company (brightness decays to 95% of the initial brightness). The test results are shown in Tables 1 to 3.

[0293] Comparative device preparation example 1: Comparative device 1

[0294] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0295] The following layers were deposited layer by layer on the ITO / Ag / ITO glass substrate: a, HT-14 and p-1 (mass ratio of 100:1) as hole injection layer with a thickness of 10 nm; b, HTL-1 as hole transport layer with a thickness of 100 nm; c, TPBA and BD (mass ratio of 95:5) as light-emitting layer with a thickness of 20 nm; d, TPBi as hole blocking layer with a thickness of 10 nm; e, BCP and Liq (mass ratio of 5:5) as electron transport layer with a thickness of 25 nm; f, LiF as electron injection layer with a thickness of 1 nm; g, Mg and Ag (mass ratio of 1:9) as cathode with a thickness of 10 nm; h: CP-4 as covering layer with a thickness of 80 nm.

[0296] Device Preparation Examples 1 to 27: Light Emitting Devices 1 to 27

[0297] The HTL-1 in the hole transport layer is replaced with the aromatic amine compounds of the present invention synthesized in Synthesis Examples 3 to 29, respectively, and the other steps are the same as those in Comparative Device Preparation Example 1, to obtain light-emitting devices 1 to 27.

[0298] Table 1

[0299]

[0300]

[0301] Comparative device preparation example 2: Comparative device 2

[0302] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0303] The following layers were deposited layer by layer on the above ITO / Ag / ITO glass substrate: a. HT-1 and p-1 (mass ratio is 100:1) as hole injection layer with a thickness of 10 nm; b. HT-1 as hole transport layer with a thickness of 90 nm; c. HTL-1 as light-emitting auxiliary layer with a thickness of 30 nm; d. RH-1, RH-2 and Ir(dpm)PQ 2 (mass ratio 47:47:6) as the light-emitting layer with a thickness of 25nm; e, TPBi as the hole blocking layer with a thickness of 10nm; f, BCP and Liq (mass ratio 5:5) as the electron transport layer with a thickness of 20nm; g, LiF as the electron injection layer with a thickness of 1nm; h, Mg and Ag (mass ratio 1:9) as the cathode with a thickness of 10nm; i: CP-4 as the covering layer with a thickness of 80nm.

[0304] Device Preparation Examples 28 to 54: Light Emitting Devices 28 to 54

[0305] The HTL-1 in the light-emitting auxiliary layer is replaced with the aromatic amine compound of the present invention synthesized in Synthesis Examples 3 to 29, and the other steps are the same as those in Comparative Device Preparation Example 2, to obtain light-emitting devices 28 to 54.

[0306] Table 2

[0307]

[0308]

[0309] Comparative device preparation example 3: Comparative device 3

[0310] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropanol, acetone and methanol for 20 minutes each, and then exposed to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0311] The following layers were deposited layer by layer on the above ITO / Ag / ITO glass substrate: a. HT-14 and p-1 (mass ratio of 100:1) as hole injection layer with a thickness of 10 nm; b. HT-8 as hole transport layer with a thickness of 120 nm; c. GH-1, GH-2 and Ir(ppy) 2 (m-bppy) (mass ratio 64:32:4) as the light-emitting layer with a thickness of 30nm; e, TPBi as the hole blocking layer with a thickness of 10nm; f, BCP and Liq (mass ratio 5:5) as the electron transport layer with a thickness of 20nm; g, LiF as the electron injection layer with a thickness of 1nm; h, Mg and Ag (mass ratio 1:9) as the cathode with a thickness of 10nm; i: CP-4 as the covering layer with a thickness of 80nm.

[0312] Device Preparation Examples 55 to 81: Light Emitting Devices 55 to 81

[0313] The CP-4 in the covering layer is replaced with the aromatic amine compounds of the present invention synthesized in Synthesis Examples 3 to 29, respectively, and the other steps are the same as those in Comparative Device Preparation Example 3, to obtain light-emitting devices 55 to 81.

[0314] Table 3

[0315]

[0316]

[0317] The device data in Table 1 and Table 2 show that the aromatic amine compound described in the present invention is used as a hole transport material in an OLED device, which greatly improves the driving voltage, luminous efficiency and service life. The device data in Table 3 show that the aromatic amine compound described in the present invention is used as a covering layer material in an OLED device, which can improve the luminous efficiency and service life of the device. In summary, the aromatic amine compound provided by the present invention is a class of OLED materials with excellent performance and has a good application prospect.

[0318] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An aromatic amine compound, characterized in that It has the structure shown in formula (I): Wherein, each occurrence of a is identically or differently selected from 0, 1, 2, 3 or 4; Each time the R appears, it is selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring; At least one of Ar1 and Ar2 is selected from the following groups: Wherein, each time the ring A appears, it is identically or differently selected from one of the following substituted or unsubstituted structures: benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring; Each time X appears, it is selected from oxygen atom, sulfur atom, N-R2, the same or different, each time R2 appears, it is selected from hydrogen atom, deuterium atom, substituted or unsubstituted C1-C12 straight chain or branched alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring fused monovalent group, substituted or unsubstituted silyl; Each time a1 appears, it is selected from 0, 1 or 2, the same or different; Each time the R1 appears, it is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group; Ar1 or Ar2 not selected from the above groups is selected from a substituted or unsubstituted C6-C30 aromatic group, a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring fused monovalent group; The Ar3 is selected from one of the following groups: wherein each time a2 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time b2 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time c2 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time d2 appears, it is selected from 0, 1 or 2 in the same or different manner; each time e2 appears, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time f2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time g2 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner; Each time the R3 appears, it is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group; The R4 is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or a substituted or unsubstituted silyl group; The R5 is selected from a substituted or unsubstituted C1-C12 straight chain or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group; The R6 is selected from a substituted or unsubstituted C1-C12 straight chain or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group; The R7 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C3-C20 aliphatic ring fused with a C6-C30 aromatic ring; The L1 is selected from one of the following groups: wherein each time a3 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time b3 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time c3 appears, it is selected from 0, 1 or 2 in the same or different manner; each time d3 appears, it is selected from 0 or 1 in the same or different manner; each time e3 appears, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time f3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; each time g3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner; Each time the R8 appears, it is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a monovalent group formed by condensing a substituted or unsubstituted C3-C20 aliphatic ring and a C6-C30 aromatic ring, and a substituted or unsubstituted silyl group; Each occurrence of R9 is identically or differently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, or a substituted or unsubstituted silyl group; The L2 and L3 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C20 aliphatic ring fused with a C6-C30 aromatic ring, or a divalent group; The condition is that at least one of the R, Ar1 to Ar3, and L1 to L3 contains a substituted or unsubstituted silyl group.

2. The aromatic amine compound according to claim 1, characterized in that At least one of R and Ar1 to Ar3 contains a substituted or unsubstituted silyl group.

3. The aromatic amine compound according to claim 1, characterized in that At least one of Ar1 and Ar2 is selected from the following groups: Among them, the a 11 Each time it occurs, it is selected from 0, 1 or 2 identically or differently; 11 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said d 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said e 11 Each time it occurs, it is selected from 0, 1, 2, 3 or 4 identically or differently; said f 11 Each time it occurs, it is selected from 0 or 1, either identically or differently; Each occurrence of X is the same or different selected from oxygen atoms, sulfur atoms, NR 21 , the R 21 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, silyl; The R 11 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, silyl; Ar1 or Ar2 not selected from the above groups is selected from one of the following groups: Among them, the a 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 12 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 12 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said d 12 Each occurrence is identically or differently selected from 0, 1 or 2; said e 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 12 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 12 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, a fluorenyl group, a benzocyclopentyl group, a benzocyclohexyl group, a silyl group, and two adjacent R 12 They may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring; The R 13 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: one of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and silyl; The R 14 A substituted or unsubstituted group selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane; The R 15 Each occurrence is identically or differently selected from the group consisting of substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl; The R 16 A substituted or unsubstituted group selected from the group consisting of phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl and benzocyclohexyl.

4. The aromatic amine compound according to claim 1, characterized in that Each time the R3 appears, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, a fluorenyl group, a benzofuranyl group, a benzothiophenyl group, an indolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a benzocyclopentyl group, a benzocyclohexyl group, or a silyl group; two adjacent R3 groups may be connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring; The R4 is selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, an adamantyl group, a norbornyl group, and a silyl group; The R5 is selected from the group consisting of substituted or unsubstituted groups as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane; The R6 is selected from the group consisting of substituted or unsubstituted groups as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl; The R7 is selected from the group consisting of substituted or unsubstituted groups as shown below: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, and benzocyclohexyl; Each time R8 appears, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, phenyl, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, and silyl. Each time R9 appears, it is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and a silyl group.

5. The aromatic amine compound according to claim 1, characterized in that The L2 and L3 are independently selected from a single bond, the following groups, or a combination thereof: Among them, the a 101 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 101 Each time it occurs, it is selected from 0, 1, 2 or 3, the same or different; 101 Each occurrence is identically or differently selected from 0, 1 or 2; said d 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said f 101 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 101 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, a phenyl group, a fluorenyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a benzocyclopentyl group, a benzocyclohexyl group, a silyl group; The R 102 Each occurrence is identically or differently selected from a hydrogen atom; a deuterium atom; a fluorine atom; a cyano group; a substituted or unsubstituted group as shown below: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and a silyl group.

6. The aromatic amine compound according to claim 1, characterized in that The aromatic amine compound is selected from one of the following compounds:

7. An organic electroluminescent device comprising an anode, a cathode, and an organic layer between the anode and the cathode, characterized in that: The organic layer contains one or more of the aromatic amine compounds according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, wherein: The hole transport region contains one or more of the aromatic amine compounds described in any one of claims 1 to 6.

9. An organic electroluminescent device comprising an anode, a cathode, an organic layer between the anode and the cathode, and a covering layer on the side of the cathode facing away from the anode, characterized in that: The covering layer contains one or more of the aromatic amine compounds described in any one of claims 1 to 6.

10. A stacked organic electroluminescent device comprising an anode, a cathode, two or more light-emitting units between the anode and the cathode, and a charge generation layer between the light-emitting units, characterized in that: The charge generating layer contains one or more of the aromatic amine compounds according to any one of claims 1 to 6.

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