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 can improve the luminous efficiency and driving voltage of the device and prolong 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, transferring energy to the light-emitting substance. 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. The hole transport region mainly plays the role of injecting and transporting holes, including one or more layers of the hole injection layer, the hole transport layer, the light-emitting auxiliary layer, and the electron blocking layer. The electron transport region mainly plays the role of injecting and transporting electrons, including one or more layers of the electron injection layer, the electron transport layer, and the hole blocking layer. 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. By setting a covering layer on the outside of the electrode on the light-emitting side (for example, the outside of the cathode of the top-emitting device), the luminous efficiency, color purity and service life of the device can be further improved. OLED researchers have also developed a stacked OLED containing two or more independent light-emitting units. Each independent light-emitting unit is connected in series through a charge generation layer (CGL). The electrons and holes generated by the CGL are respectively injected into the adjacent light-emitting units, and are recombined into excitons in the light-emitting unit to emit light. In addition, n-type doped layers / p-type doped layers are often used as charge generation 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, the ring A is selected from one of the substituted or unsubstituted structures shown below: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane;

[0008] Each time a appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time b appears, it is selected from 0, 1, 2 or 3 in the same or different manner;

[0009] Each time the R appears, it is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 straight chain or branched alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring;

[0010] The Ar1 is selected from one of the following groups:

[0011]

[0012] Wherein, the ring B is selected from one of the substituted or unsubstituted structures shown below: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring;

[0013] The X is selected from oxygen atom, sulfur atom, N-R2, and the R2 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, a monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted silyl.

[0014] The R1 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, 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] Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted o-phenanthroline, substituted or unsubstituted phenanthridinyl or one of the following groups:

[0016]

[0017] Among them, the a 30 is selected from 0, 1 or 2; said b 30 Select from 0 or 1;

[0018] The ring C, ring D, and ring G, when they appear each time, are selected from the same or different groups consisting of one or more R 30 A substituted or unsubstituted one of the following structures: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring;

[0019] The R 30Each occurrence is identically or differently 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, an anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclopentane group, a substituted or unsubstituted benzocyclohexane group, a substituted or unsubstituted benzocycloheptane group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, and a substituted or unsubstituted silyl group;

[0020] The R 50 , R 60 Independently 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, or the two are connected to form a ring;

[0021] The R 70 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups;

[0022] The Y is selected from oxygen atom, sulfur atom, NR 80 , the R 80 One selected from the group consisting of 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;

[0023] The L1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene;

[0024] The L2 and L3 are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene.

[0025] 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 comprises a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains one or more of the aromatic amine compounds described in the present invention. Preferably, the hole transport layer contains one or more of the aromatic amine compounds described in the present invention.

[0026] 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.

[0027] 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.

[0028] Beneficial effects:

[0029] 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, which can improve 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

[0030] 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.

[0031] 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.

[0032] 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".

[0033] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0034] The "silyl group" mentioned in the present invention refers to a -SiH3 group, and the "substituted or unsubstituted silyl group" mentioned herein refers to one or more H groups on the silyl group being substituted or unsubstituted by a substituent.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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:

[0050]

[0051] 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.

[0052] In the present specification, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0053] The present invention provides an aromatic amine compound having a structure shown in formula (I):

[0054]

[0055] Wherein, the ring A is selected from one of the substituted or unsubstituted structures shown below: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane;

[0056] Each time a appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time b appears, it is selected from 0, 1, 2 or 3 in the same or different manner;

[0057] Each time the R appears, it is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 straight chain or branched alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring;

[0058] The Ar1 is selected from one of the following groups:

[0059]

[0060] Wherein, the ring B is selected from one of the substituted or unsubstituted structures shown below: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring;

[0061] The X is selected from oxygen atom, sulfur atom, N-R2, and the R2 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, a monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted silyl.

[0062] The R1 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, 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;

[0063] Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted o-phenanthroline, substituted or unsubstituted phenanthridinyl or one of the following groups:

[0064]

[0065] Among them, the a 30 is selected from 0, 1 or 2; said b 30 Select from 0 or 1;

[0066] The ring C, ring D, and ring G, when they appear each time, are selected from the same or different groups consisting of one or more R 30 A substituted or unsubstituted one of the following structures: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring;

[0067] The R 30 Each occurrence is identically or differently 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, an anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclopentane group, a substituted or unsubstituted benzocyclohexane group, a substituted or unsubstituted benzocycloheptane group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, and a substituted or unsubstituted silyl group;

[0068] The R 50 , R 60 Independently 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, or the two are connected to form a ring;

[0069] The R70 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups;

[0070] The Y is selected from oxygen atom, sulfur atom, NR 80 , the R 80 One selected from the group consisting of 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;

[0071] The L1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene;

[0072] The L2 and L3 are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene.

[0073] 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.

[0074] 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.

[0075] Preferably, the ring A is selected from one of the following structures substituted or unsubstituted with one or more of 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: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane.

[0076] Preferably, the ring A is selected from the group consisting of a deuterium atom, a fluorine atom, a cyano group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a n-propyl group, an isopropyl group, a deuterated isopropyl group, a n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, and a group substituted or unsubstituted with one or more of three substituted or unsubstituted silyl groups, which may be the same or different, selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl groups: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane and norbornane.

[0077] Preferably, each time the R 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, 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 silyl group, and two adjacent R groups can be connected to form a ring; preferably, the Ar1 is selected from one of the groups shown below:

[0078]

[0079]

[0080] wherein each time a1 appears, it is selected from 0, 1 or 2 in the same or different manner; each time b1 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time c1 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time d1 appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7 in the same or different manner; each time e1 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time f1 appears, it is selected from 0 or 1 in the same or different manner; each time g1 appears, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time h1 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner;

[0081] Each time X appears, it is selected from oxygen atom, sulfur atom, N-R2 in the same or different manner; each time R2 appears, it is selected from hydrogen atom in the same or different manner; deuterium atom; substituted or unsubstituted groups 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;

[0082] Each time R1 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, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, and silyl.

[0083] Preferably, the Ar1 is selected from one of the following groups:

[0084]

[0085]

[0086]

[0087] Preferably, the Ar2 is selected from one of the following groups:

[0088]

[0089]

[0090] wherein each time a3 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time b3 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time c3 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time d3 appears, it is selected from 0, 1 or 2 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 or 1 in the same or different manner; each time h3 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 in the same or different manner;

[0091] Each time the R3 occurs, it is identically or differently selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted C1-C6 straight or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclopentane group, substituted or unsubstituted benzocyclohexane group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted isoquinolyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted silyl group;

[0092] Each time the R4 appears, it is identically or differently selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted C1-C12 straight chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted silyl group;

[0093] The R5 and R6 are independently 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;

[0094] The R7 is selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group;

[0095] The Y is selected from one of oxygen atoms, sulfur atoms, and N-R8, and the R8 is selected from one of hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C12 straight or branched alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, 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.

[0096] Preferably, each time 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: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, and silyl.

[0097] Preferably, R4 is 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, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornyl, and silyl.

[0098] Preferably, R5 and R6 are independently selected from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, phenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl.

[0099] Preferably, R7 is selected from the group consisting of substituted or unsubstituted groups as shown below: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl.

[0100] Preferably, R8 is 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, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocyclopentyl, benzocyclohexyl, and silyl.

[0101] Preferably, the Ar2 is selected from one of the following groups:

[0102]

[0103]

[0104] Preferably, L1 is selected from a single bond, a group as shown below, or a combination thereof:

[0105]

[0106] The L2 and L3 are independently selected from a single bond, the following groups, or a combination thereof:

[0107]

[0108] 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;

[0109] 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 C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C10 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;

[0110] The R 102 Each time it occurs, it is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted silyl group.

[0111] Preferably, the R 101Each 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, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, benzocyclopentyl, benzocyclohexyl, and silyl.

[0112] Preferably, 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.

[0113] Preferably, L1 is selected from a single bond, a group as shown below, or a combination thereof:

[0114]

[0115] Preferably, L2 and L3 are independently selected from a single bond, a group as shown below, or a combination thereof:

[0116]

[0117] Preferably, the aromatic amine compound has one of the structures shown below:

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131] 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.

[0132] The aromatic amine compound of the present invention can be prepared by one of the following synthetic routes:

[0133] Synthesis route 1:

[0134]

[0135] Synthesis route 2:

[0136]

[0137] Synthesis route three:

[0138]

[0139] In each of the above synthetic routes, the X1, when it appears each time, is selected from a chlorine atom, a bromine atom or an iodine atom, the same or different;

[0140] The rings A, a, b, R, Ar1, Ar2, and L1-L3 are all as described in the present invention.

[0141] 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).

[0142] 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.

[0143] 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 comprises a hole transport region, a light emitting layer, and an electron transport region, and the organic layer contains one or more of the aromatic amine compounds described in the present invention. Preferably, the hole transport region contains one or more of the aromatic amine compounds described in the present invention.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148]

[0149] 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.

[0150] 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.

[0151] The light-emitting layer of the present invention includes a guest material and a host material, and a dual host material formed by two host materials can be used. The guest material can use a fluorescent compound, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, etc. Examples 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), etc., phosphorescent materials can also be used, such as metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)picolinoyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), etc. The host material preferably uses a substance with a higher LUMO and a lower HOMO than that of the guest material, for example, 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, examples of which include Alq3, BAlq, TPBI, TPD, 4,4'-di(9-carbazole)biphenyl (CBP), 4,4',4"-tri(carbazole-9-yl)triphenylamine (TCTA), and 9,10-di(2-naphthyl)anthracene (ADN), but are not limited thereto.

[0152] 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.

[0153] 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, and can be selected from one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited thereto.

[0154] The electron transport layer described in 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. 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 can be used. Examples include 8-hydroxyquinoline aluminum (Alq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), and 2-(4-biphenyl)-5-phenyloxadiazole (PBD), but are not limited to these.

[0155] 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.

[0156] The anode described in 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 it can be a layer structure with a high work function and is transparent or translucent, such as a layer structure formed by indium tin oxide (ITO), indium zinc oxide (ZnO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3) or tin oxide (SnO2). It depends on the type of device to be prepared. 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.

[0157] 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.

[0158] The covering 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 covering layer material can use organic or inorganic substances with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compound of the present invention, but are not limited thereto.

[0159]

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] The above-mentioned organic layers are preferably prepared by vacuum evaporation, inkjet printing or spin coating.

[0171] 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.

[0172] 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.

[0173] The technical scheme and technical effects of the present invention are further illustrated below with reference to embodiments and comparative examples.

[0174] 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;

[0175] 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.

[0176] Synthesis Example 1: Synthesis of Intermediate BB / DD

[0177] Synthesis of intermediate DD-63:

[0178]

[0179] Under argon atmosphere, aa-63 (11.94 g, 60 mmol), bb-63 (7.82 g, 50 mmol), Pd(PPh3)4 (0.23 g, 0.2 mmol), potassium carbonate aqueous solution (14.51 g, 105 mmol), toluene (370 mL) were added to the reaction bottle and refluxed for 24 hours. After the reaction was completed, it was cooled to room temperature, water was added to quench the reaction, and it was extracted with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated and purified by silica gel column (dichloromethane: petroleum ether = 1:1) to obtain DD-63 (8.76 g, 76%); HPLC purity ≥ 99.84%. Mass spectrum m / z: 230.0258 (theoretical value: 230.0247).

[0180] By replacing the raw materials accordingly and following the synthesis method of intermediate DD-63, other intermediates BB / DD can be obtained, as shown in the following table:

[0181]

[0182] Synthesis Example 2: Synthesis of Compound 63

[0183]

[0184] Under nitrogen protection, AA-63 (6.58 g, 30 mmol), BB-63 (8.98 g, 30 mmol), Pd(OAc)2 (0.07 g, 0.3 mmol), P(t-Bu)3 (1.2 mL of 0.5 M toluene solution, 0.6 mmol), sodium tert-butoxide (5.77 g, 60 mmol), toluene (270 mL) were added to the reaction bottle, the mixture was stirred, and heated to reflux for 5 h. After the reaction was completed, it was cooled to room temperature, distilled water was added to wash the mixture, and then extracted with dichloromethane, allowed to stand for separation, the organic phase was collected and dried with anhydrous magnesium sulfate, cooled for crystallization, filtered, and the residue was recrystallized with toluene / methanol (volume ratio 9:1) to obtain intermediate CC-63 (11.42 g, 87%). The solid purity was ≥99.82% by HPLC. Mass spectrum m / z: 437.2162 (theoretical value: 437.2143).

[0185] Under nitrogen protection, CC-63 (4.38 g, 10 mmol), DD-63 (2.31 g, 10 mmol), Pd2(dba)3 (0.09 g, 0.1 mmol), P(t-Bu)3 (0.4 mL of 0.5 M toluene solution, 0.2 mmol), sodium tert-butoxide (1.92 g, 20 mmol), toluene (100 mL) were added to the reaction bottle, the mixture was stirred, and heated to reflux for 6.5 h. After the reaction was completed, it was cooled to room temperature, the mixture was washed with distilled water, extracted with dichloromethane, allowed to stand for separation, the organic phase was collected and dried with anhydrous magnesium sulfate, cooled for crystallization, filtered, and the residue was recrystallized from toluene to obtain compound 63 (5.12 g, 81%). The solid purity was ≥99.93% by HPLC. Mass spectrum m / z: 631.2635 (theoretical value: 631.2624). Theoretical element content (%) C 45 H 33 N3O: C, 85.55; H, 5.27; N, 6.65. Measured element content (%): C, 85.53; H, 5.23; N, 6.69.

[0186] Synthesis Example 3: Synthesis of Compound 91

[0187]

[0188] AA-63 was replaced by an equal molar amount of AA-91, and DD-63 was replaced by an equal molar amount of DD-91. The other steps were the same as those in Synthesis Example 2 to obtain Compound 91 (5.58 g, yield 75%). The solid purity was ≥ 99.90% as determined by HPLC. Mass spectrum m / z: 743.3320 (theoretical value: 743.3300). Theoretical element content (%) C 55 H 41N3: C, 88.80; H, 5.56; N, 5.65. Measured element content (%): C, 88.86; H, 5.52; N, 5.62.

[0189] Synthesis Example 4: Synthesis of Compound 110

[0190]

[0191] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-110. The other steps were the same as those in Synthesis Example 2 to obtain Compound 110 (4.70 g, yield 79%). The solid purity was ≥ 99.90% by HPLC. Mass spectrum m / z: 594.2662 (theoretical value: 594.2671). Theoretical element content (%) C 43 H 34 N2O: C, 86.84; H, 5.76; N, 4.71. Measured element content (%): C, 86.87; H, 5.71; N, 4.74.

[0192] Synthesis Example 5: Synthesis of Compound 128

[0193]

[0194] AA-63 was replaced by an equal molar amount of AA-128, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-128. The other steps were the same as those in Synthesis Example 2 to obtain Compound 128 (5.47 g, yield 77%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 710.3285 (theoretical value: 710.3297). Theoretical element content (%) C 52 H 42 N2O: C, 87.85; H, 5.96; N, 3.94. Measured element content (%): C, 87.87; H, 5.99; N, 3.90.

[0195] Synthesis Example 6: Synthesis of Compound 190

[0196]

[0197] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 190 (5.06 g, yield 85%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 594.2687 (theoretical value: 594.2671). Theoretical element content (%) C 43 H 34 N2O: C, 86.84; H, 5.76; N, 4.71. Measured element content (%): C, 86.88; H, 5.70; N, 4.74.

[0198] Synthesis Example 7: Synthesis of Compound 206

[0199]

[0200] AA-63 was replaced by an equal molar amount of AA-206, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-206. The other steps were the same as those in Synthesis Example 2 to obtain Compound 206 (5.55 g, yield 78%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 710.3284 (theoretical value: 710.3297). Theoretical element content (%) C 52 H 42 N2O: C, 87.85; H, 5.96; N, 3.944. Measured element content (%): C, 87.87; H, 5.92; N, 3.97.

[0201] Synthesis Example 8: Synthesis of Compound 210

[0202]

[0203] AA-63 was replaced by an equal molar amount of AA-91, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-210. The other steps were the same as those in Synthesis Example 2 to obtain Compound 210 (6.15 g, yield 81%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 758.3286 (theoretical value: 758.3297). Theoretical element content (%) C 56 H 42 N2O: C, 88.62; H, 5.58; N, 3.69. Measured element content (%): C, 88.68; H, 5.54; N, 3.64.

[0204] Synthesis Example 9: Synthesis of Compound 215

[0205]

[0206] AA-63 was replaced by an equal molar amount of AA-215, BB-63 was replaced by an equal molar amount of BB-215, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 215 (6.22 g, yield 79%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 786.3627 (theoretical value: 786.3610). Theoretical element content (%) C 58 H 46 N2O: C, 88.52; H, 5.89; N, 3.56. Measured element content (%): C, 88.59; H, 5.84; N, 3.51.

[0207] Synthesis Example 10: Synthesis of Compound 228

[0208]

[0209] AA-63 was replaced by an equal molar amount of AA-215, BB-63 was replaced by an equal molar amount of BB-228, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 228 (6.69 g, yield 77%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 868.4380 (theoretical value: 868.4393). Theoretical element content (%) C 64 H 56 N2O: C, 88.44; H, 6.49; N, 3.22. Measured element content (%): C, 88.47; H, 6.41; N, 3.27.

[0210] Synthesis Example 11: Synthesis of Compound 232

[0211]

[0212] AA-63 was replaced by an equal molar amount of AA-232, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-206. The other steps were the same as those in Synthesis Example 2 to obtain Compound 232 (6.51 g, yield 78%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 834.3625 (theoretical value: 834.3610). Theoretical element content (%) C 62 H 46 N2O: C, 89.18; H, 5.55; N, 3.35. Measured element content (%): C, 89.11; H, 5.59; N, 3.38.

[0213] Synthesis Example 12: Synthesis of Compound 238

[0214]

[0215] AA-63 was replaced by an equal molar amount of AA-238, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 238 (5.41 g, yield 79%). The solid purity was ≥ 99.97% by HPLC. Mass spectrum m / z: 684.2791 (theoretical value: 684.2777). Theoretical element content (%) C 49 H 36 N2O2: C, 85.94; H, 5.30; N, 4.09. Measured element content (%): C, 85.98; H, 5.35; N, 4.04.

[0216] Synthesis Example 13: Synthesis of Compound 243

[0217]

[0218] AA-63 was replaced by an equal molar amount of AA-243, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 243 (6.08 g, yield 80%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 759.3267 (theoretical value: 759.3250). Theoretical element content (%) C 55 H 41 N3O: C, 86.93; H, 5.44; N, 5.53. Measured element content (%): C, 86.91; H, 5.41; N, 5.59.

[0219] Synthesis Example 14: Synthesis of Compound 248

[0220]

[0221] AA-63 was replaced by an equal molar amount of AA-215, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 248 (5.38 g, yield 74%). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 726.3628 (theoretical value: 726.3610). Theoretical element content (%) C 53 H 46N2O: C, 87.57; H, 6.38; N, 3.85. Measured element content (%): C, 87.55; H, 6.33; N, 3.90.

[0222] Synthesis Example 15: Synthesis of Compound 304

[0223]

[0224] AA-63 was replaced by an equal molar amount of AA-304, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-304. The other steps were the same as those in Synthesis Example 2 to obtain Compound 304 (5.56 g, yield 78%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 712.2931 (theoretical value: 712.2912). Theoretical element content (%) C 51 H 40 N2S: C, 85.92; H, 5.66; N, 3.93. Measured element content (%): C, 85.97; H, 5.63; N, 3.90.

[0225] Synthesis Example 16: Synthesis of Compound 308

[0226]

[0227] AA-63 was replaced by an equal molar amount of AA-308, BB-63 was replaced by an equal molar amount of BB-308, and DD-63 was replaced by an equal molar amount of DD-308. The other steps were the same as those in Synthesis Example 2 to obtain Compound 308 (5.66 g, yield 75%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 754.3365 (theoretical value: 754.3382). Theoretical element content (%) C 54 H 46 N2S: C, 85.90; H, 6.14; N, 3.71. Measured element content (%): C, 85.96; H, 6.10; N, 3.69.

[0228] Synthesis Example 17: Synthesis of Compound 329

[0229]

[0230] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-329. The other steps were the same as those in Synthesis Example 2 to obtain Compound 329 (4.76 g, yield 78%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 610.2461 (theoretical value: 610.2443). Theoretical element content (%) C 43 H 34 N2S: C, 84.55; H, 5.61; N, 4.59. Measured element content (%): C, 84.54; H, 5.58; N, 4.64.

[0231] Synthesis Example 18: Synthesis of Compound 331

[0232]

[0233] AA-63 was replaced by an equal molar amount of AA-331, BB-63 was replaced by an equal molar amount of BB-331, and DD-63 was replaced by an equal molar amount of DD-331. The other steps were the same as those in Synthesis Example 2 to obtain Compound 331 (5.22 g, yield 76%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 686.2768 (theoretical value: 686.2756). Theoretical element content (%) C 49 H 38 N2S: C, 85.68; H, 5.58; N, 4.08. Measured element content (%): C, 85.65; H, 5.56; N, 4.14.

[0234] Synthesis Example 19: Synthesis of Compound 333

[0235]

[0236] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-333. The other steps were the same as those in Synthesis Example 2 to obtain Compound 333 (5.29 g, yield 77%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 686.2779 (theoretical value: 686.2756). Theoretical element content (%) C 49 H 38 N2S: C, 85.68; H, 5.58; N, 4.08. Measured element content (%): C, 85.62; H, 5.60; N, 4.12.

[0237] Synthesis Example 20: Synthesis of Compound 377

[0238]

[0239] AA-63 was replaced by an equal molar amount of AA-377, BB-63 was replaced by an equal molar amount of aa-331, and DD-63 was replaced by an equal molar amount of DD-377. The other steps were the same as those in Synthesis Example 2 to obtain Compound 377 (5.72 g, yield 74%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 772.2928 (theoretical value: 772.2912). Theoretical element content (%) C 56 H 40 N2S: C, 87.01; H, 5.22; N, 3.62. Measured element content (%): C, 87.07; H, 5.18; N, 3.61.

[0240] Synthesis Example 21: Synthesis of Compound 431

[0241]

[0242] AA-63 was replaced by an equal molar amount of AA-431, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-431. The other steps were the same as those in Synthesis Example 2 to obtain Compound 431 (4.70 g, yield 75%). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 626.3284 (theoretical value: 626.3297). Theoretical element content (%) C 45 H 42 N2O: C, 86.22; H, 6.75; N, 4.47. Measured element content (%): C, 86.20; H, 6.79; N, 4.43.

[0243] Synthesis Example 22: Synthesis of Compound 437

[0244]

[0245] AA-63 was replaced by an equal molar amount of AA-437, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-110. The other steps were the same as those in Synthesis Example 2 to obtain Compound 437 (5.61 g, yield 78%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 718.3363 (theoretical value: 718.3379). Theoretical element content (%) C 50 H 46N2OSi: C, 83.52; H, 6.45; N, 3.90. Measured element content (%): C, 83.55; H, 6.41; N, 3.92.

[0246] Synthesis Example 23: Synthesis of Compound 442

[0247]

[0248] AA-63 was replaced by an equal molar amount of AA-91, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-442. The other steps were the same as those in Synthesis Example 2 to obtain Compound 442 (5.59 g, yield 76%). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 734.3277 (theoretical value: 734.3297). Theoretical element content (%) C 54 H 42 N2O: C, 88.25; H, 5.76; N, 3.81. Measured element content (%): C, 88.28; H, 5.71; N, 3.85.

[0249] Synthesis Example 24: Synthesis of Compound 457

[0250]

[0251] AA-63 was replaced by an equal molar amount of AA-377, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-110. The other steps were the same as those in Synthesis Example 2 to obtain Compound 457 (6.23 g, yield 77%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 808.3468 (theoretical value: 808.3454). Theoretical element content (%) C 60 H 44 N2O: C, 89.08; H, 5.48; N, 3.46. Measured element content (%): C, 89.05; H, 5.43; N, 3.52.

[0252] Synthesis Example 25: Synthesis of Compound 468

[0253]

[0254] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-468. The other steps were the same as those in Synthesis Example 2 to obtain Compound 468 (5.30 g, yield 76%). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 696.3157 (theoretical value: 696.3141). Theoretical element content (%) C 51 H 40 N2O: C, 87.90; H, 5.79; N, 4.02. Measured element content (%): C, 87.95; H, 5.73; N, 4.04.

[0255] Synthesis Example 26: Synthesis of Compound 472

[0256]

[0257] AA-63 was replaced by an equal molar amount of AA-110, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-210. The other steps were the same as those in Synthesis Example 2 to obtain Compound 472 (4.85 g, yield 75%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 646.2996 (theoretical value: 646.2984). Theoretical element content (%) C 47 H 38 N2O: C, 87.27; H, 5.92; N, 4.33. Measured element content (%): C, 87.25; H, 5.90; N, 4.39.

[0258] Synthesis Example 27: Synthesis of Compound 473

[0259]

[0260] AA-63 was replaced by an equal molar amount of AA-473, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-473. The other steps were the same as those in Synthesis Example 2 to obtain Compound 473 (5.08 g, yield 78%). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 651.3278 (theoretical value: 651.3298). Theoretical element content (%) C 47 H 33 D5N2O: C, 86.60; H, 6.65; N, 4.30. Measured element content (%): C, 86.62; H, 6.61; N, 4.34.

[0261] Synthesis Example 28: Synthesis of Compound 477

[0262]

[0263] AA-63 was replaced by an equal molar amount of AA-477, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 477 (5.15 g, yield 75%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 686.3285 (theoretical value: 686.3297). Theoretical element content (%) C 50 H 42 N2O: C, 87.43; H, 6.16; N, 4.08. Measured element content (%): C, 87.48; H, 6.12; N, 4.05.

[0264] Synthesis Example 29: Synthesis of Compound 478

[0265]

[0266] AA-63 was replaced by an equal molar amount of AA-206, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-210. The other steps were the same as those in Synthesis Example 2 to obtain Compound 478 (5.22 g, yield 76%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 686.3283 (theoretical value: 686.3297). Theoretical element content (%) C 50 H 42 N2O: C, 87.43; H, 6.16; N, 4.08. Measured element content (%): C, 87.46; H, 6.11; N, 4.13.

[0267] Synthesis Example 30: Synthesis of Compound 481

[0268]

[0269] AA-63 was replaced by an equal molar amount of AA-481, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-190. The other steps were the same as those in Synthesis Example 2 to obtain Compound 481 (6.33 g, yield 78%). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 810.3628 (theoretical value: 810.3610). Theoretical element content (%) C 60 H 46N2O: C, 88.86; H, 5.72; N, 3.45. Measured element content (%): C, 88.82; H, 5.70; N, 3.50.

[0270] Synthesis Example 31: Synthesis of Compound 484

[0271]

[0272] AA-63 was replaced by an equal molar amount of AA-484, BB-63 was replaced by an equal molar amount of BB-484, and DD-63 was replaced by an equal molar amount of DD-210. The other steps were the same as those in Synthesis Example 2 to obtain Compound 484 (5.77 g, yield 77%). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 748.3469 (theoretical value: 748.3454). Theoretical element content (%) C 55 H 44 N2O: C, 88.20; H, 5.92; N, 3.74. Measured element content (%): C, 88.17; H, 5.98; N, 3.71.

[0273] Synthesis Example 32: Synthesis of Compound 493

[0274]

[0275] AA-63 was replaced by an equal molar amount of AA-493, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-206. The other steps were the same as those in Synthesis Example 2 to obtain Compound 493 (7.40 g, yield 79%). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 736.3074 (theoretical value: 736.3090). Theoretical element content (%) C 53 H 40 N2O2: C, 86.38; H, 5.47; N, 3.80. Measured element content (%): C, 86.36; H, 5.42; N, 3.87.

[0276] Synthesis Example 33: Synthesis of Compound 496

[0277]

[0278] AA-63 was replaced by an equal molar amount of AA-496, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-210. The other steps were the same as those in Synthesis Example 2 to obtain Compound 496 (6.01 g, yield 74%). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 811.3577 (theoretical value: 811.3563). Theoretical element content (%) C 59 H 45 N3O: C, 87.27; H, 5.59; N, 5.17. Measured element content (%): C, 87.21; H, 5.63; N, 5.19.

[0279] Synthesis Example 34: Synthesis of Compound 500

[0280]

[0281] Under nitrogen protection, AA-484 (3.01 g, 10 mmol), DD-190 (2.74 g, 20 mmol), Pd2(dba)3 (0.18 g, 0.2 mmol), P(t-Bu)3 (0.4 mL of 0.5 M toluene solution, 0.4 mmol), sodium tert-butoxide (3.84 g, 40 mmol), toluene (200 mL) were added to the reaction bottle, the mixture was stirred, and heated to reflux for 6.5 h. After the reaction was completed, it was cooled to room temperature, the mixture was washed with distilled water, extracted with dichloromethane, allowed to stand for separation, the organic phase was collected and dried with anhydrous magnesium sulfate, cooled for crystallization, filtered, and the residue was recrystallized from toluene to obtain compound 500 (5.23 g, 76%). The solid purity was ≥99.94% by HPLC. Mass spectrum m / z: 687.2869 (theoretical value: 687.2886). Theoretical element content (%) C 48 H 37 N3O2: C, 83.82; H, 5.42; N, 6.11. Measured element content (%): C, 83.87; H, 5.40; N, 6.08.

[0282] Synthesis Example 35: Synthesis of Compound 510

[0283]

[0284] AA-63 was replaced by an equal molar amount of AA-91, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-510. The other steps were the same as those in Synthesis Example 2 to obtain Compound 510 (5.92 g, yield 73%). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 810.3625 (theoretical value: 810.3610). Theoretical element content (%) C 60 H 46 N2O: C, 88.86; H, 5.72; N, 3.45. Measured element content (%): C, 88.82; H, 5.78; N, 3.42.

[0285] Synthesis Example 36: Synthesis of Compound 522

[0286]

[0287] AA-63 was replaced by an equal molar amount of AA-522, BB-63 was replaced by an equal molar amount of BB-522, and DD-63 was replaced by an equal molar amount of DD-522. The other steps were the same as those in Synthesis Example 2 to obtain Compound 522 (5.12 g, yield 72%). The solid purity was ≥ 99.90% by HPLC. Mass spectrum m / z: 710.3674 (theoretical value: 710.3695). Theoretical element content (%) C 50 H 50 N2S: C, 84.46; H, 7.09; N, 3.94. Measured element content (%): C, 84.43; H, 7.07; N, 3.99.

[0288] Synthesis Example 37: Synthesis of Compound 549

[0289]

[0290] AA-63 was replaced by an equal molar amount of AA-232, BB-63 was replaced by an equal molar amount of BB-248, and DD-63 was replaced by an equal molar amount of DD-331. The other steps were the same as those in Synthesis Example 2 to obtain Compound 549 (6.12 g, yield 74%). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 826.3365 (theoretical value: 826.3382). Theoretical element content (%) C 60 H 46 N2S: C, 87.13; H, 5.61; N, 3.39. Measured element content (%): C, 87.19; H, 5.57; N, 3.34.

[0291] The following are other compounds used in the device preparation examples except the aromatic amine compound described in the present invention:

[0292]

[0293] 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.

[0294] Comparative device preparation example 1: Comparative device 1

[0295] 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.

[0296] The following layers were deposited layer by layer on the above ITO / Ag / ITO glass substrate: a, HT-8 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 110 nm; c, BDAF and BD (mass ratio of 93:7) 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.

[0297] Comparative device preparation example 2: Comparative device 2

[0298] The HTL-1 in the hole transport layer is replaced by HTL-2, and the other steps are the same as those in the comparative device preparation example 1, so as to obtain the comparative device 2.

[0299] Device Preparation Examples 1 to 36: Light Emitting Devices 1 to 36

[0300] The HTL-1 in the hole transport layer is replaced with the aromatic amine compounds of the present invention synthesized in Synthesis Examples 2 to 37, respectively, and the other steps are the same as those in Comparative Device Preparation Example 1, to obtain light-emitting devices 1 to 36.

[0301] Table 1

[0302]

[0303]

[0304]

[0305] Comparative device preparation example 3: Comparative device 3

[0306] 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.

[0307] 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-7 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)PQ2 (mass ratio of 47:47:6) as light-emitting layer with a thickness of 25 nm; e, TPBi as hole blocking layer with a thickness of 10 nm; f, BCP and Liq (mass ratio of 5:5) as electron transport layer with a thickness of 20 nm; g, LiF as electron injection layer with a thickness of 1 nm; h, Mg and Ag (mass ratio of 1:9) as cathode with a thickness of 10 nm; i: CP-4 as covering layer with a thickness of 80 nm.

[0308] Comparative device preparation example 4: Comparative device 4

[0309] The HTL-1 in the light-emitting auxiliary layer is replaced by HTL-2, and the other steps are the same as those in Preparation Example 3 of the Comparative Device, thereby obtaining Comparative Device 4.

[0310] Device Preparation Examples 37 to 72: Light Emitting Devices 37 to 72

[0311] The HTL-1 in the light-emitting auxiliary layer is replaced with the aromatic amine compounds of the present invention synthesized in Synthesis Examples 2 to 37 in sequence, and the other steps are the same as those in Comparative Device Preparation Example 3, to obtain light-emitting devices 37 to 72.

[0312] Table 2

[0313]

[0314]

[0315] Comparative device preparation example 5: Comparative device 5

[0316] 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.

[0317] The following layers were deposited layer by layer on the above ITO / Ag / ITO glass substrate: a, HT-1 and p-1 (mass ratio of 100:1) as hole injection layer with a thickness of 10 nm; b, HT-1 as hole transport layer with a thickness of 100 nm; c, GH-1, GH-2 and Ir(ppy)2(m-bppy) (mass ratio of 32:64:4) as light-emitting layer with a thickness of 30 nm; e, TPBi as hole blocking layer with a thickness of 10 nm; f, BCP and Liq (mass ratio of 5:5) as electron transport layer with a thickness of 20 nm; g, LiF as electron injection layer with a thickness of 1 nm; h, Mg and Ag (mass ratio of 1:9) as cathode with a thickness of 10 nm; i: CP-4 as covering layer with a thickness of 80 nm.

[0318] Device Preparation Examples 73 to 91: Light Emitting Devices 73 to 91

[0319] The CP-4 in the covering layer is replaced with the aromatic amine compounds 63, 110, 128, 190, 206, 210, 238, 243, 329, 437, 472, 473, 477, 478, 481, 493, 500, 510, and 549 described in the present invention synthesized in Synthesis Examples 2 to 37 in sequence, and the other steps are the same as those in Comparative Device Preparation Example 5, to obtain light-emitting devices 73 to 91.

[0320] Table 3

[0321] Device Embodiment Covering Luminous efficiency (cd / A) Lifespan (h) Comparative device preparation example 5 CP-4 36.51 110.5 Device Preparation Example 73 63 46.81 137.0 Device Preparation Example 74 110 47.51 147.9 Device Preparation Example 75 128 47.14 144.1 Device Preparation Example 76 190 48.03 139.7 Device Preparation Example 77 206 47.58 144.8 Device Preparation Example 78 210 47.23 148.8 Device Preparation Example 79 238 47.71 145.9 Device Preparation Example 80 243 46.73 140.5 Device Preparation Example 81 329 48.45 141.2 Device Preparation Example 82 437 48.36 152.5 Device Preparation Example 83 472 48.25 143.2 Device Preparation Example 84 473 48.61 153.8 Device Preparation Example 85 477 47.30 142.7 Device Preparation Example 86 478 47.81 142.0 Device Preparation Example 87 481 47.39 150.1 Device Preparation Example 88 493 48.16 151.2 Device Preparation Example 89 500 47.96 138.0 Device Preparation Example 90 510 46.95 138.9 Device Preparation Example 91 549 47.06 147.0

[0322] 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 luminous efficiency, service life and driving voltage. The device data in Table 3 show that the aromatic amine compound described in the present invention can also be used as a covering layer material to 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.

[0323] 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, the ring A is selected from one of the substituted or unsubstituted structures shown below: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane; Each time a appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time b appears, it is selected from 0, 1, 2 or 3 in the same or different manner; Each time the R appears, it is selected from the group consisting of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 straight chain or branched alkyl group, substituted or unsubstituted C3-C12 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted silyl group, and two adjacent R groups can be connected to form a ring; The Ar1 is selected from one of the following groups: Wherein, the ring B is selected from one of the substituted or unsubstituted structures shown below: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring; The X is selected from oxygen atom, sulfur atom, N-R2, and the R2 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, a monovalent group formed by fusion of substituted or unsubstituted C3-C20 aliphatic ring and C6-C30 aromatic ring, and substituted or unsubstituted silyl. The R1 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, 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; Ar2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropane, substituted or unsubstituted benzocyclobutane, substituted or unsubstituted benzocyclopentane, substituted or unsubstituted benzocyclohexane, substituted or unsubstituted benzocycloheptane, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinolyl, substituted or unsubstituted o-phenanthroline, substituted or unsubstituted phenanthridinyl or one of the following groups: Among them, the a 30 is selected from 0, 1 or 2; said b 30 Select from 0 or 1; The ring C, ring D, and ring G, when they appear each time, are selected from the same or different groups consisting of one or more R 30 A substituted or unsubstituted one of the following structures: benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, acridine ring, phenanthridine ring, benzoquinoline ring; The R 30 Each occurrence is identically or differently 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, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, an anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzocyclopropane group, a substituted or unsubstituted benzocyclobutane group, a substituted or unsubstituted benzocyclopentane group, a substituted or unsubstituted benzocyclohexane group, a substituted or unsubstituted benzocycloheptane group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, and a substituted or unsubstituted silyl group; The R 50 , R 60 Independently 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, or the two are connected to form a ring; The R 70 One selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C2-C30 heteroaryl groups; The Y is selected from oxygen atom, sulfur atom, NR 80 , the R 80 One selected from the group consisting of 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; The L1 is selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene; The L2 and L3 are independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthrylene, a substituted or unsubstituted phenanthrylene, a substituted or unsubstituted benzocyclopropanediylene, a substituted or unsubstituted benzocyclobutanediylene, a substituted or unsubstituted benzocyclopentanediylene, a substituted or unsubstituted benzocyclohexanediylene, a substituted or unsubstituted benzocycloheptanediylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted benzofuranylene, a substituted or unsubstituted benzothiophenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidylene, a substituted or unsubstituted quinolylene, a substituted or unsubstituted isoquinolylene, a substituted or unsubstituted quinazolinylene, and a substituted or unsubstituted quinoxalinylene.

2. The aromatic amine compound according to claim 1, characterized in that The Ar1 is selected from one of the following groups: wherein each time a1 appears, it is selected from 0, 1 or 2 in the same or different manner; each time b1 appears, it is selected from 0, 1, 2 or 3 in the same or different manner; each time c1 appears, it is selected from 0, 1, 2, 3, 4 or 5 in the same or different manner; each time d1 appears, it is selected from 0, 1, 2, 3, 4, 5, 6 or 7 in the same or different manner; each time e1 appears, it is selected from 0, 1, 2, 3 or 4 in the same or different manner; each time f1 appears, it is selected from 0 or 1 in the same or different manner; each time g1 appears, it is selected from 0, 1, 2, 3, 4, 5 or 6 in the same or different manner; each time h1 appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8 in the same or different manner; Each time X appears, it is selected from oxygen atom, sulfur atom, N-R2 in the same or different manner; each time R2 appears, it is selected from hydrogen atom in the same or different manner; deuterium atom; substituted or unsubstituted groups 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; Each time R1 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, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, benzofuranyl, benzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzocyclopentyl, benzocyclohexyl, and silyl.

3. The aromatic amine compound according to claim 1, characterized in that The Ar2 is selected from one of the following groups: wherein each time a3 appears, it is identically or differently selected from 0, 1, 2, 3, 4 or 5; each time b3 appears, it is identically or differently selected from 0, 1, 2, 3 or 4; each time c3 appears, it is identically or differently selected from 0, 1, 2 or 3; each time d3 appears, it is identically or differently selected from 0, 1 or 2; each time e3 appears, it is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; each time f3 appears, it is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; each time g3 appears, it is identically or differently selected from 0 or 1; each time h3 appears, it is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; each time i3 appears, it is identically or differently selected from 0, 1, 2, 3, 4, 5, 6 or 7; Each time the R3 occurs, it is identically or differently selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted C1-C6 straight or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted benzocyclopropane group, substituted or unsubstituted benzocyclobutane group, substituted or unsubstituted benzocyclopentane group, substituted or unsubstituted benzocyclohexane group, substituted or unsubstituted benzocycloheptane group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidyl group, substituted or unsubstituted quinolyl group, substituted or unsubstituted isoquinolyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted silyl group; Each time the R4 appears, it is identically or differently selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, substituted or unsubstituted C1-C12 straight chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted silyl group; The R5 and R6 are independently 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; The Y is selected from one of oxygen atoms, sulfur atoms, and N-R8, and the R8 is selected from one of hydrogen atoms, deuterium atoms, substituted or unsubstituted C1-C12 straight or branched alkyl groups, substituted or unsubstituted C3-C12 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, 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.

4. The aromatic amine compound according to claim 3, 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 cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, an adamantyl group, a norbornane group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylene group, and a silyl group; 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; R5 and R6 are independently 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, n-pentyl, n-hexyl, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl; The R7 is selected from the group consisting of substituted or unsubstituted groups as shown below: phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl; The R8 is 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, phenanthryl, triphenylene, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, benzofuranyl, benzothiophenyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocyclopentyl, benzocyclohexyl, and silyl.

5. The aromatic amine compound according to claim 1, characterized in that The L1 is selected from a single bond, the following groups, or a combination thereof: 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 C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C10 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 R 102 Each time it occurs, it is identically or differently selected from one of the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a cyano group, a substituted or unsubstituted C1-C12 straight or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted 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, wherein the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, 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, characterized in that: 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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