An arylamine compound and an organic electroluminescence device thereof

Abstract

The present application relates to the technical field of organic photoelectric material, in particular to a kind of arylamine compound and organic electroluminescent device thereof.The arylamine compound shown in formula (I) provided by the present application has good hole migration ability, and proper HOMO and T1 value, is applied to OLED device as hole transport material, can improve the transmission efficiency of hole, collocates other functional layer, can improve the luminous efficiency of device;It also has good stability, can resist high temperature and corrosive gas, thereby prolonging the service life of device;The arylamine compound also has good space configuration, excellent arrangement between molecules, good film-forming property, further improve the luminous efficiency and service life of device.Summarized above, the arylamine compound provided by the present application has the advantages of proper energy level, good stability, good film-forming property etc., can be used as hole transport material, can also be used as the host material of light-emitting layer and cover layer material, is a kind of excellent performance, widely used OLED material.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) have advantages such as light weight, small size, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high definition, and good flexibility, and have great application prospects in the fields of lighting and display.

[0003] Classic OLED devices have a "sandwich" structure, with an emissive layer sandwiched between two electrodes, a cathode and an anode, containing a luminescent material. When a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode, respectively, recombine in the emissive layer to form excitons, releasing energy. These excitons migrate, transferring energy to the guest material. Electrons in the guest material molecules transition from the ground state to an excited state. Since the excited state is unstable, the electrons migrate back to the stable ground state, releasing energy as light, producing the luminescence phenomenon. To improve the performance of OLED devices, such as driving voltage, luminous efficiency, color purity, and lifespan, additional organic functional layers are added between the anode and the emissive layer, and between the cathode and the emissive layer. Generally, the organic functional layer between the anode and the emissive layer acts as a hole transport region, while the organic functional layer between the cathode and the emissive layer acts as an electron transport region. The hole transport region includes one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer. The electron transport region includes one or more of the following: an electron injection layer, an electron transport layer, and a hole blocking layer. To further improve the luminous efficiency and lifespan of the device, a capping layer is often provided on the outer side of the electrode on the light-emitting side.

[0004] Hole transport materials generally require high hole mobility, appropriate highest occupied molecular orbitals (HOMO) and triplet energy levels (T1), good stability, and film-forming properties. The host material typically needs a higher LUMO value and a lower HOMO value than the guest material. Aromatic amine compounds are currently one of the most widely used OLED materials. These compounds possess the properties required of hole transport materials, and different aromatic amine compounds exhibit varying performance characteristics. They can be used as hole transport functional layers, host materials for emissive layers, or capping layers in OLED devices. Summary of the Invention

[0005] To address the aforementioned technical problems, this invention provides an aromatic amine compound possessing high hole mobility, appropriate HOMO and T1 values. It can be used as a hole transport material, a host material for the light-emitting layer, and a capping layer material, achieving excellent device performance in all applications. The aromatic amine compound has the structure shown in formula (I):

[0006]

[0007] Wherein, L1 to L9 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a substituted or unsubstituted C3 to C7 aliphatic ring;

[0008] Each time a1 appears, it is selected from 0, 1, or 2, either the same or different.

[0009] Each time b1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different.

[0010] Each time R1 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or substituted or unsubstituted C3-C10 cycloalkenyl group.

[0011] The Ar1 to Ar6 are independently selected from one of the following: a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a substituted or unsubstituted C3 to C7 aliphatic ring;

[0012] The substituents in "substituted or unsubstituted" are selected from deuterium atoms; halogen atoms; cyano groups; and C1-C12 straight-chain or branched alkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, deuterated methyl groups, deuterated ethyl groups, deuterated isopropyl groups, deuterated tert-butyl groups, phenyl groups, deuterated phenyl groups, naphthyl groups, deuterated naphthyl groups, biphenyl groups, and deuterated biphenyl groups. A C3-C12 cycloalkyl group substituted or unsubstituted with one or more of the following groups: alkyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; alkyl group substituted or unsubstituted with one of the following groups: deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, or biphenyl. A C3-C12 cycloalkenyl group substituted or unsubstituted with one or more of the groups consisting of deuterated biphenyl groups; a C6-C30 aryl group substituted or unsubstituted with one or more of the groups consisting of deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl groups; a C6-C30 aryl group substituted or unsubstituted with one or more of the groups consisting of deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, deuterated biphenyl groups; The silyl group is one or more substituted or unsubstituted from the group consisting of propyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl, wherein the substituent is one or more, and when there are multiple substituents, the multiple substituents are the same or different, and when there are multiple substituents, two adjacent substituents can be linked to form a substituted or unsubstituted saturated or unsaturated C3 to C6 carbon ring.

[0013] Beneficial effects:

[0014] The aromatic amine compound represented by formula (I) provided by this invention has excellent hole migration ability and appropriate HOMO and T1 values. When used as a hole transport material in OLED devices, it can improve hole transport efficiency. Combined with other functional layers, it can improve the luminous efficiency of the device. At the same time, it also has good thermal and chemical stability, and can withstand high temperature and corrosive gases, thereby extending the life of the device. The aromatic amine compound also has a good spatial configuration and excellent molecular arrangement, which has good film-forming properties, further improving the luminous efficiency and life of the device.

[0015] In summary, the aromatic amine compounds provided by this invention have advantages such as appropriate energy levels, good stability, and good film-forming properties. They can be used as hole transport materials, as well as as the main material for the light-emitting layer and the capping layer material. They are a class of high-performance and widely used OLED materials. Detailed Implementation

[0016] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0017] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0018] The halogen atoms mentioned in this invention refer to fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0019] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomers of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0020] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, or norbornane.

[0021] The cycloalkenyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkene molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto. The cycloalkenyl groups described above are preferably cyclopentenyl or cyclohexenyl.

[0022] The cycloalkynyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkynyl 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 cyclopropynyl, cyclobutynyl, cyclopentynyl, cyclohexynyl, cycloheptynyl, etc., but are not limited thereto. The cycloalkynyl groups described above are preferably cyclopentynyl or cyclohexynyl.

[0023] The heterocyclic group described in this invention refers to a group formed by removing one hydrogen atom from a heterocyclic molecule that contains at least one heteroatom in addition to carbon atoms. The heteroatom includes nitrogen, oxygen, sulfur, silicon, etc., preferably nitrogen, oxygen, or sulfur. 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 ethylene oxide, cyclothioethylene, propylidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazine, etc., but are not limited thereto. The aforementioned heterocyclic group is preferably tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, or piperazine.

[0024] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, 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 aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0025] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0026] The term "group formed by the fusion of an aromatic ring and an aliphatic ring" as used in this invention refers to the general term for a monovalent group formed by the fusion of an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) and the removal of one hydrogen atom. Preferably, it has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms. Examples include benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but are not limited to these.

[0027] In this invention, the term arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that arylene is a divalent group.

[0028] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the hybrid aryl group is a divalent group.

[0029] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring as described in this invention refers to a group formed by the fusion of an aromatic ring and an aliphatic ring having two bonding sites, i.e., a divalent group. It can be applied to the above description of groups formed by the fusion of an aromatic ring and an aliphatic ring, the difference being that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

[0030] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0031] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: halogen atom, deuterium atom, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C1-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 cycloalkynyl. The following are substituted or unsubstituted C3-C30 heterocyclic groups, substituted or unsubstituted C1-C30 alkoxy groups, substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C6-C60 aryloxy groups, substituted or unsubstituted C2-C60 heteroaryl groups, substituted or unsubstituted silyl groups, preferably halogen atoms, cyano groups, deuterium atoms, C1-C12 alkyl groups, C3-C12 cycloalkyl groups, C3-C12 cycloalkenyl groups, C3-C12 heterocyclic groups, and C6-C30 alkyl groups. One or more of aryl, C3-C30 heteroaryl, and silyl groups, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other; preferably, this means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, norberyl Alkyl, methoxy, ethoxy, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, where the substituents are the same or different from each other when substituted by multiple substituents.

[0032] In the instruction manual, This refers to the portion that is connected to another substituent. It can be attached to any optional position of the group / fragment to which it is attached. For example express And so on.

[0033] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent And so on.

[0034] The linked ring structure described in this invention refers to the interconnection of various groups by chemical bonds, optionally forming double / triple bonds, and can constitute aromatic groups, as shown in the following example:

[0035]

[0036]

[0037] In this invention, the bonded ring can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of the two. It can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring. Examples may include benzene, naphthalene, indene, fluorene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited thereto.

[0038] Furthermore, two groups attached to the same nitrogen atom can be linked together to form a ring, as shown in the following example:

[0039]

[0040] In this invention, the ring formed by two groups connected to the same nitrogen atom can be carbazole, or a group in which one or two benzene rings of carbazole are fused with benzene rings or naphthalene rings.

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

[0042]

[0043] Wherein, L1 to L9 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a substituted or unsubstituted C3 to C7 aliphatic ring;

[0044] Each time a1 appears, it is selected from 0, 1, or 2, either the same or different.

[0045] Each time b1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different.

[0046] Each time R1 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C12 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or substituted or unsubstituted C3-C10 cycloalkenyl group.

[0047] The Ar1 to Ar6 are independently selected from one of the following: a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aromatic ring fused with a substituted or unsubstituted C3 to C7 aliphatic ring;

[0048] The substituents in "substituted or unsubstituted" are selected from deuterium atoms; halogen atoms; cyano groups; and C1-C12 straight-chain or branched alkyl groups substituted or unsubstituted by one or more of the group consisting of deuterium atoms, halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, deuterated methyl groups, deuterated ethyl groups, deuterated isopropyl groups, deuterated tert-butyl groups, phenyl groups, deuterated phenyl groups, naphthyl groups, deuterated naphthyl groups, biphenyl groups, and deuterated biphenyl groups. A C3-C12 cycloalkyl group substituted or unsubstituted with one or more of the following groups: alkyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; alkyl group substituted or unsubstituted with one of the following groups: deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, or biphenyl. A C3-C12 cycloalkenyl group substituted or unsubstituted with one or more of the groups consisting of deuterated biphenyl groups; a C6-C30 aryl group substituted or unsubstituted with one or more of the groups consisting of deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl groups; a C6-C30 aryl group substituted or unsubstituted with one or more of the groups consisting of deuterium atom, halogen atom, cyano, methyl, ethyl, n-propyl, isopropyl, deuterated biphenyl groups; The silyl group is one or more substituted or unsubstituted from the group consisting of propyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl, wherein the substituent is one or more, and when there are multiple substituents, the multiple substituents are the same or different, and when there are multiple substituents, two adjacent substituents can be linked to form a substituted or unsubstituted saturated or unsaturated C3 to C6 carbon ring.

[0049] Preferably, the substituent in "substituted or unsubstituted" is selected from the group consisting of deuterium atom; methyl; deuterated methyl; ethyl; deuterated ethyl; n-propyl; isopropyl; deuterated isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; deuterated tert-butyl; cyclopropane group substituted or unsubstituted by one or more of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl; cyclopropane group substituted or unsubstituted by one of the group consisting of deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterated biphenyl Cyclobutyl groups with one or more substituted or unsubstituted components; cyclopentyl groups with one or more substituted or unsubstituted components from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclohexyl groups with one or more substituted or unsubstituted components from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; cyclohexyl groups with one or more substituted or unsubstituted components from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, and deuterated phenyl. Cyclopropenyl groups substituted or unsubstituted with one or more of the group consisting of naphthyl, deuteronyl, biphenyl, and deuteronylbiphenyl; cyclobutenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuteronylmethyl, deuteronylisopropyl, deuteronyltert-butyl, phenyl, deuteronyl, naphthyl, deuteronyl, biphenyl, and deuteronylbiphenyl; cyclopentenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuteronylmethyl, deuteronylisopropyl, deuteronyltert-butyl, phenyl, deuteronyl, naphthyl, deuteronyl, biphenyl, and deuteronylbiphenyl; cyclopentenyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, and deuteronylbiphenyl. Cyclohexenyl groups substituted or unsubstituted with one or more of the group consisting of methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; adamantyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; norbornenealkyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl;A phenyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; One or more substituted or unsubstituted naphthyl groups from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl groups; anthraceneyl groups substituted or unsubstituted by one or more substituted or unsubstituted anthraceneyl groups from the group consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, and deuterated... A phenanthrene group substituted or unsubstituted with one or more of the groups consisting of phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a triphenylene group substituted or unsubstituted with one or more of the groups consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl; a phenanthrene group substituted or unsubstituted with one or more of the groups consisting of deuterium, methyl, ethyl, isopropyl, n-butyl, tert-butyl, and deuterated biphenyl. The silyl group comprising one or more of the following groups: deuterated methyl, deuterated isopropyl, deuterated tert-butyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, biphenyl, and deuterated biphenyl. The silyl group may be one or more substituents. When there are multiple substituents, the multiple substituents may be the same or different. When there are multiple substituents, adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring.

[0050] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures:

[0051]

[0052] Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0053] The R mentioned 11Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0054] The R mentioned 12 R 13 Independently selected from one of substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or the R mentioned above. 12 With R 13 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C6 carbon rings.

[0055] Preferably, the R 11 Each time it appears, it is selected from the same or different groups: hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano group; methyl group; ethyl group; n-propyl group; isopropyl group; n-butyl group; tert-butyl group; deuterated methyl group; deuterated ethyl group; deuterated isopropyl group; deuterated tert-butyl group; trifluoromethyl group; cyclopropane group; cyclobutane group; cyclopentane group; cyclohexane group; cycloheptane group; cyclopentenyl group; cyclohexenyl group; adamantyl group; norbornel group; deuterated group. A phenyl group consisting of one or more substituted or unsubstituted atoms from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel; a phenyl group substituted or unsubstituted with one atom; A naphthyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; a biphenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl.

[0056] Preferably, the R 12 R 13 The phenyl group independently selected from the group consisting of methyl; ethyl; isopropyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; phenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; phenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl A naphthyl group substituted or unsubstituted with one or more of the group consisting of alkyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; or a biphenyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl, or the aforementioned R. 12 With R 13 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C6 carbon rings.

[0057] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures:

[0058]

[0059]

[0060] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures:

[0061]

[0062] Preferably, each time R1 appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted sec-butyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted cyclopropane group, substituted or unsubstituted cyclobutane group, substituted or unsubstituted cyclopentane group, substituted or unsubstituted cyclohexane group, substituted or unsubstituted cycloheptane group, substituted or unsubstituted cyclopropene group, substituted or unsubstituted cyclobutenyl group, substituted or unsubstituted cyclopentenyl group, substituted or unsubstituted cyclohexenyl group, substituted or unsubstituted adamantyl group, and substituted or unsubstituted norbornel group.

[0063] Preferably, each time R1 appears, it is selected, either identically or differently, from the group consisting of hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; trifluoromethyl; substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel. Cyclopropane; cyclobutane substituted or unsubstituted by one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; cyclobutane substituted or unsubstituted by one of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane Cyclopentyl groups substituted or unsubstituted with one or more of the group consisting of alkyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, and tert-butyl. Cycloheptyl groups substituted or unsubstituted with one or more of the following groups: deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; adamantyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl.One or more of the norbornel groups substituted or unsubstituted by one of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel.

[0064] Preferably, each occurrence of R1 is selected, either identically or differently, from one of the following structures: hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, ethyl group, isopropyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, or the structure shown below:

[0065]

[0066] Preferably, Ar1 to Ar6 are independently selected from one of the following structures:

[0067]

[0068] Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the d mentioned 21 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different.

[0069] The R mentioned 21 Each time it appears, it is selected from one of the following groups, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C3-C10 cycloalkenyl group, substituted or unsubstituted C6-C12 aryl group, or a group formed by fusion of a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring;

[0070] The R mentioned 22 R 23Independently selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted sec-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted tert-butyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted tetrahydronaphthyl group, or the aforementioned R group. 22 With R 23 They connect to form substituted or unsubstituted saturated or unsaturated C3-C6 carbon rings;

[0071] The L mentioned 21 It is selected from one of substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthylene, and substituted or unsubstituted biphenylene.

[0072] Preferably, the R 21Each time it appears, it is selected, either identically or differently, from the group consisting of hydrogen atom; deuterium atom; fluorine atom; chlorine atom; bromine atom; iodine atom; cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; trifluoromethyl; cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; cyclopropane, cyclobutane, cyclopentyl, cyclohexenyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; Cyclobutyl groups substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, norbornel group; cyclobutane groups substituted or unsubstituted with one of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, deuterated methyl group, deuterated ethyl group, deuterated isopropyl group, deuterated tert-butyl group, trifluoromethyl group, cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group. Cyclopentyl groups substituted or unsubstituted with one or more of the group consisting of alkyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl groups; cyclohexyl groups substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, and deuterium groups. Cycloheptyl groups substituted or unsubstituted with one or more of the following groups: methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; cyclopentenyl groups substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl.A cyclohexenyl group substituted or unsubstituted by one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; a cyclohexenyl group substituted or unsubstituted by one of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl. Adamantyl group substituted or unsubstituted with one or more of the group consisting of cyclohexenyl, adamantyl, and norbornyl; norbornyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; norbornyl group substituted or unsubstituted with one or more of the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated ...tert-butyl, A phenyl group substituted or unsubstituted with one or more of the following groups: butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; a naphthyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, and n-propyl. Anthracene group substituted or unsubstituted with one or more of the following groups: cyclopropane, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; phenanthrene group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl;A biphenyl group substituted or unsubstituted with one or more of the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; One or more substituted or unsubstituted fluorene groups from the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel.

[0073] Preferably, the R 22 R 23The phenyl group independently selected from the group consisting of methyl; ethyl; isopropyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; phenyl group substituted or unsubstituted with one or more of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano; methyl; ethyl; n-propyl; isopropyl; n-butyl; tert-butyl; deuterated methyl; deuterated ethyl; deuterated isopropyl; deuterated tert-butyl; trifluoromethyl; cyclopropane; cyclobutane; cyclopentane; cyclohexane; cycloheptane; cyclopentenyl; cyclohexenyl; adamantyl; norbornel ...propane; cyclobutane; cyclopentane; cyclohexenyl; adamantyl; norborne The naphthyl group substituted or unsubstituted with one or more of the following groups: chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, norbornel; a naphthyl group substituted or unsubstituted with one of the following groups: deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl. Biphenyl groups substituted or unsubstituted with one or more of the following groups: deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel; biphenyl groups substituted or unsubstituted with one of the following atoms: deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, or cyclopentenyl. One or more substituted or unsubstituted indenyl groups from the group consisting of cyclohexenyl, adamantyl, and norbornel; one or more substituted or unsubstituted tetrahydronaphthyl groups from the group consisting of deuterium, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, trifluoromethyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentenyl, cyclohexenyl, adamantyl, and norbornel; or the aforementioned R. 22 With R 23 They connect to form substituted or unsubstituted saturated or unsaturated C3 to C6 carbon rings.

[0074] Preferably, the L 21 Choose one of the following structures:

[0075]

[0076] Preferably, the L 21 Choose one of the following structures:

[0077]

[0078] Preferably, Ar1 to Ar6 are independently selected from one of the following structures:

[0079]

[0080]

[0081] Preferably, the aromatic amine compound has the structure shown in formula (IA):

[0082]

[0083] Wherein, L1~L9 and Ar1~Ar6 are as described in this invention.

[0084] Preferably, the aromatic amine compound has one of the structures shown in formulas (IB) to (IH):

[0085]

[0086]

[0087] Wherein, L1~L9 and Ar1~Ar6 are as described in this invention.

[0088] Preferably, the aromatic amine compound has one of the structures shown in formulas (IJ) to (IU):

[0089]

[0090] Wherein, L1~L9 and Ar1~Ar6 are as described in this invention.

[0091] Preferably, the aromatic amine compound is selected from one of the following structures:

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] The above only lists some specific structural forms of the compounds represented by formula (I), but the present invention is not limited to these chemical structures. Any chemical structure based on formula (I) with substituents as defined above should be included.

[0105] The aromatic amine compounds of this invention can be prepared by any of the following synthetic routes:

[0106] Synthesis Route 1:

[0107]

[0108] Synthesis Route 2:

[0109]

[0110] Combining synthesis route one with synthesis route two yields the following synthesis route:

[0111] Synthesis Route 3:

[0112]

[0113] Synthesis Route 4:

[0114]

[0115] Wherein, L1-L9, a1, b1, R1, and Ar1-Ar6 are as described in this invention; X1-X3 are independently selected from chlorine atoms, bromine atoms, or iodine atoms; when L1 is selected from a single bond, Y1 is selected from hydrogen; when L1 is selected from one of substituted or unsubstituted C6-C30 arylene groups, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene group, Y1 is selected from... When L2 is selected from a single bond, Y2 is selected from hydrogen. When L2 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene, Y2 is selected from... When L3 is selected from a single bond, Y3 is selected from hydrogen. When L3 is selected from one of the following: a substituted or unsubstituted C6-C30 arylene, a divalent group formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or a substituted or unsubstituted C3-C30 heteroarylene, Y3 is selected from...

[0116] In synthetic route one, compound (A) can be reacted with aromatic amine compounds (B), (C), and (D) in one or more steps via a Buchwald–Hartwig reaction or a Suzuki coupling reaction to obtain the compound shown in formula (I).

[0117] In synthetic route two, compound (E) can react with compounds (F), (G), and (H) in one or more steps via the Buchwald–Hartwig reaction to obtain the compound shown in formula (I).

[0118] In synthetic route three, compound (J) can react with compounds (F) and (G) in one or two steps via a Buchwald-Hartwig reaction to obtain intermediate (K); then, intermediate (K) reacts with compound (D) via a Buchwald-Hartwig reaction or a Suzuki coupling reaction to obtain the compound shown in formula (I).

[0119] In synthetic route four, compound (L) reacts with compound (B) via a Buchwald–Hartwig reaction or a Suzuki coupling reaction to give intermediate (M); then, intermediate (M) reacts with compounds (G) and (H) via a one-step or two-step Buchwald–Hartwig reaction to give the compound shown in formula (I).

[0120] All the above reaction routes employ commonly used reaction types in organic synthesis, and there are no particular restrictions on the reaction conditions (e.g., the selection, amount, order, and method of adding reaction solvents, catalysts, ligands, bases, etc., can be done using conventional methods). The above preparation methods use readily available raw materials, have simple processes, and yield excellent results. The compound represented by formula (I) provided by this invention can also be synthesized using other conventional reaction types in organic synthesis without particular restrictions; the above are merely examples of synthetic routes.

[0121] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains the aromatic amine compound described in the present invention.

[0122] Preferably, the organic electroluminescent device further includes a capping layer, which is located on the side of the cathode away from the anode or on the side of the anode away from the cathode.

[0123] The hole transport region includes one or more of the following: a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0124] The hole injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds, and other substances with high hole injection properties can be used. Examples include 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzenephenanthrene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), and compounds HT-1 to HT. -15, compound p-1, compound p-2, compound p-3, and the aromatic amine compounds described in this invention, but not limited thereto. Preferably, the hole injection layer is a monolayer structure composed of a matrix material and a dopant material. The matrix material can be a triaromatic amine compound, such as compounds HT-1 to HT-19, or the aromatic amine compounds described in this invention. The dopant material can be an axial alkene compound, preferably compound p-1, compound p-2, or compound p-3. More preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:50. Even more preferably, the mass ratio of the matrix material to the dopant material is 100:1 to 100:10.

[0125]

[0126]

[0127] The hole transport layer described in this invention can be a monolayer structure composed of a single material, or a monolayer or multilayer structure composed of different materials. Triarylamine compounds can be used, or other compounds with a hole mobility of 10... -6 cm 2Examples of substances with a density of / Vs or higher include N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4,4'4"-tris(N,N-diphenylamino)triphenylamine (TDATA), compounds HT-1 to HT-19, and the aromatic amine compounds described in this invention, but are not limited thereto. Preferably, the hole transport layer contains the aromatic amine compounds described in this invention.

[0128] The luminescent auxiliary layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, or other substances with suitable HOMO and T1 energy levels can be used. Examples include TPD, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl, N4'-[1,1':4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, and N-([1,1'-diphenyl]-4-yl) -N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, compounds HT-1 to HT-19, and the aromatic amine compounds described in this invention, but not limited thereto. Preferably, the luminescent auxiliary layer contains the aromatic amine compounds described in this invention.

[0129] The luminescent layer of the present invention may contain only a guest material, or the guest material may be dispersed in a host material, and two host materials may be used to form a dual host material. The guest material may be a fluorescent compound, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-Bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi) and other materials can also be used, such as phosphorescent materials, metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridineformyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), and bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)). The host material is preferably a substance with a higher LUMO than the guest material and a lower HOMO than the guest material. Examples include metal complexes such as aluminum or zinc complexes, heterocyclic compounds such as oxadiazole or benzimidazole derivatives, fused aromatic compounds such as carbazole or anthracene derivatives, and aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives. Examples include aluminum 8-hydroxyquinoline (Alq3) and bis(2-methyl-8-hydroxyquinoline-N1,O8). )-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBI), TPD, 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-bis(2-naphthyl)anthracene (ADN), compounds HT-1 to HT-19, and aromatic amine compounds described in this invention, but not limited thereto.

[0130] The electron transport region described in this invention includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0131] The electron injection layer described in this invention can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. It can be one or more of the following substances: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited to these.

[0132] The electron transport layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can use aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, triazine derivatives, phenanthroline derivatives, polymers, etc. with high electron transport properties. Examples include Alq3, bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, 2-(4-biphenyl)-5-phenyloxadiazole (PBD), etc., but are not limited to these.

[0133] The hole-blocking layer described in this invention can be a single-layer structure composed of a single material, or a single-layer or multi-layer structure composed of different materials. The selected material must have a T1 energy level higher than that of the emissive layer to prevent energy loss from the emissive layer. Furthermore, the HOMO energy level of the selected material must be lower than that of the main material of the emissive layer to effectively block holes. Further, the electron mobility of the hole-blocking layer material used is 10. -6 cm 2 A concentration of / Vs or higher facilitates electron transport. Triazine derivatives and azirene derivatives are preferred.

[0134] The anode described in this invention can be a reflective anode, such as a reflective film formed from silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr), ytterbium (Yb), or their alloys. It can also be a transparent or translucent layered structure formed from a high work function material, such as a layered structure formed from 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). Alternatively, it can be a reflective film formed from the aforementioned metals and the aforementioned high work function materials. The specific anode depends on the type of device to be fabricated. For example, if the device to be fabricated is a bottom-emitting device (emitting light from the anode side), a transparent or translucent anode needs to be fabricated. If the device to be fabricated is a top-emitting device (emitting light from the cathode side), a reflective anode needs to be fabricated.

[0135] The cathode described in this invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, magnesium-silver alloy, etc. The thickness of the film can be adjusted to create a reflective electrode, a transparent electrode, or a semi-transparent electrode. The specific choice depends on the type of device to be fabricated. For example, a reflective cathode is required for a bottom-emitting device, while a transparent or semi-transparent cathode is required for a top-emitting device.

[0136] The capping layer described in this invention can be a single-layer structure composed of a single substance, a single-layer structure composed of different substances, a multi-layer structure composed of a single substance, or a multi-layer structure composed of different substances. The capping layer material can be organic or inorganic, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compounds described in this invention, but are not limited thereto.

[0137]

[0138] Preferably, the hole transport region contains the aromatic amine compound described in this invention.

[0139] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, and one of the hole injection layer and the hole transport layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the hole transport layer contains one or more of the aromatic amine compounds described in this invention.

[0140] Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer, wherein one of the hole injection layer, the hole transport layer, and the light-emitting auxiliary layer contains one or more of the aromatic amine compounds described in this invention; more preferably, the light-emitting auxiliary layer contains the aromatic amine compounds described in this invention.

[0141] Preferably, the light-emitting layer contains the aromatic amine compound described in this invention.

[0142] Preferably, the light-emitting layer contains a guest material and a host material, wherein the host material contains the aromatic amine compound described in this invention.

[0143] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, an organic layer located between the anode and the cathode, and a capping layer, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the capping layer is located on the side of the cathode away from the anode or the side of the anode away from the cathode, and the capping layer contains the aromatic amine compound described in the present invention.

[0144] Preferably, the structure of the organic layer is selected from one of the following:

[0145] i-1) Hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer;

[0146] i-2) Hole injection layer / hole transport layer / light emission layer / hole blocking layer / electron transport layer / electron injection layer;

[0147] i-3) Hole injection layer / hole transport layer / luminescent auxiliary layer / luminescent layer / electron transport layer / electron injection layer;

[0148] i-4) Hole injection layer / hole transport layer / luminescence auxiliary layer / luminescence layer / hole blocking layer / electron transport layer / electron injection layer.

[0149] Preferably, the device structure of the organic electroluminescent device of the present invention is selected from one of the following device structures:

[0150] ii-1) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode / capping layer;

[0151] ii-2) Anode / hole injection layer / hole transport layer / light emission layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer;

[0152] ii-3) Anode / hole injection layer / hole transport layer / light-emitting auxiliary layer / light-emitting layer / electron transport layer / electron injection layer / cathode / capping layer;

[0153] ii-4) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Assist Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Capping Layer;

[0154] ii-5) Capping layer / Anode / Hole injection layer / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode;

[0155] ii-6) Capping layer / Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode;

[0156] ii-7) Capping layer / Anode / Hole injection layer / Hole transport layer / Light emission auxiliary layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode;

[0157] ii-8) Capping layer / Anode / Hole injection layer / Hole transport layer / Light emission auxiliary layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode.

[0158] The aforementioned organic layers, cathode, anode, and capping layer can be prepared using any of the following methods: vacuum evaporation, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, impregnation, or screen printing. There are no particular limitations on the thickness of each layer, as long as good device performance is achieved. Preferably, the aforementioned organic layers are prepared using vacuum evaporation, inkjet printing, or spin coating.

[0159] The thickness of each of the aforementioned organic layers and capping layers is typically between 5 nm and 100 μm, preferably between 10 nm and 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0160] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0161] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0162] The mass spectrometry of the compounds of this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments Ltd., UK, with chloroform as the solvent.

[0163] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0164] [Synthesis Example 1] Synthesis of Compound 1

[0165]

[0166] Under nitrogen protection, aa-1 (30.00 mmol, 10.95 g), bb-1 (95.00 mmol, 16.08 g), tris(dibenzylacetone)palladium (1.80 mmol, 1.65 g), tri-tert-butylphosphine (3.60 mmol, 0.73 g), sodium tert-butoxide (180.00 mmol, 17.30 g), and 300 ml of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. The mixture was recrystallized from toluene to give compound 1 (13.04 g, yield 69%). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrometry m / z: 629.2845 (theoretical value: 629.2831). Theoretical elemental content (%) C 46 H 35 N3: C, 87.73; H, 5.60; N, 6.67. Measured elemental content (%): C, 87.72; H, 5.61; N, 6.66.

[0167] [Synthesis Example 2] Preparation of Compound 8

[0168]

[0169] Under nitrogen protection, aa-8 (50.00 mmol, 16.02 g), bb-1 (105.00 mmol, 17.77 g), tris(dibenzylacetone)palladium (2.00 mmol, 1.83 g), tri-tert-butylphosphine (4.00 mmol, 0.81 g), sodium tert-butoxide (200.00 mmol, 19.22 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. The mixture was recrystallized from toluene to give cc-8 (19.38 g, yield 78%). The purity of the solid was ≥99.71% as determined by HPLC.

[0170] Under nitrogen protection, cc-8 (30.00 mmol, 14.91 g), dd-8 (35.00 mmol, 11.25 g), palladium acetate (0.60 mmol, 0.13 g), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (1.20 mmol, 0.57 g), sodium tert-butoxide (60.00 mmol, 5.77 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 5.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. The mixture was recrystallized from toluene to give compound 8 (15.72 g, yield 67%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 781.3447 (theoretical value: 781.3457). Theoretical element content (%) C 58 H 43 N3: C, 89.08; H, 5.54; N, 5.37. Measured elemental content (%): C, 89.07; H, 5.55; N, 5.33.

[0171] [Synthetic Example 3] Synthesis of Compound 14

[0172]

[0173] Following the preparation method of Synthesis Example 1, bb-1 was replaced with an equimolar amount of bb-14 to obtain compound 14 (16.99 g, 66%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 857.3785 (theoretical value: 857.3770). Theoretical elemental content (%) C 64 H 47 N3: C, 89.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 89.59; H, 5.53; N, 4.87.

[0174] [Synthetic Example 4] Synthesis of Compound 24

[0175]

[0176] Following the preparation method of Synthesis Example 1, bb-1 was replaced with an equimolar amount of bb-24 to obtain compound 24 (14.74 g, 63%), with a solid purity ≥99.95% as determined by HPLC. Mass spectrometry m / z: 779.3318 (theoretical value: 779.3300). Theoretical elemental content (%) C 58 H 41 N3: C, 89.31; H, 5.30; N, 5.39. Measured elemental content (%): C, 89.33; H, 5.28; N, 5.38.

[0177] [Synthetic Example 5] Synthesis of Compound 30

[0178]

[0179] Following the preparation method of Synthesis Example 2, dd-8 was replaced with an equimolar amount of dd-30 to obtain compound 30 (14.51 g, 64%), with a solid purity ≥99.97% as determined by HPLC. Mass spectrometry m / z: 755.3308 (theoretical value: 755.3300). Theoretical elemental content (%) C 56 H 41 N3: C, 88.97; H, 5.47; N, 5.56. Measured element content (%): C, 88.91; H, 5.51; N, 5.57.

[0180] [Synthetic Example 6] Synthesis of Compound 40

[0181]

[0182] Following the preparation method of Synthesis Example 2, bb-1 was replaced with an equimolar amount of bb-24, and dd-8 was replaced with an equimolar amount of dd-40, yielding compound 40 (15.14 g, 62%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 813.4095 (theoretical value: 813.4083). Theoretical elemental content (%) C 60 H 51 N3: C, 88.52; H, 6.31; N, 5.16. Measured elemental content (%): C, 88.51; H, 6.32; N, 5.18.

[0183] [Synthetic Example 7] Synthesis of Compound 47

[0184]

[0185] Following the preparation method of Synthesis Example 2, bb-1 was replaced with an equimolar amount of dd-30, and dd-8 was replaced with an equimolar amount of bb-1, yielding compound 47 (16.67 g, 63%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 881.3778 (theoretical value: 881.3770). Theoretical elemental content (%) C 66 H 47 N3: C, 89.87; H, 5.37; N, 4.76. Measured elemental content (%): C, 89.88; H, 5.38; N, 4.73.

[0186] [Synthetic Example 8] Synthesis of Compound 84

[0187]

[0188] Following the preparation method of Synthesis Example 2, aa-8 was replaced with an equimolar amount of aa-84, and dd-8 was replaced with an equimolar amount of dd-84, yielding compound 84 (14.67 g, 64%). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 763.3933 (theoretical value: 763.3926). Theoretical elemental content (%) C 56 H 49 N3: C, 88.04; H, 6.46; N, 5.50. Measured elemental content (%): C, 88.05; H, 6.47; N, 5.47.

[0189] [Synthesis Example 9] Synthesis of Compound 103

[0190]

[0191] Following the preparation method of Synthesis Example 2, dd-8 was replaced with an equimolar amount of dd-103 to obtain compound 103 (14.55 g, 65%), with a solid purity ≥99.97% as determined by HPLC. Mass spectrometry m / z: 745.3447 (theoretical value: 745.3457). Theoretical elemental content (%) C 55 H 43 N3: C, 88.56; H, 5.81; N, 5.63. Measured elemental content (%): C, 88.55; H, 5.85; N, 5.61.

[0192] [Synthetic Example 10] Synthesis of Compound 120

[0193]

[0194] Under nitrogen protection, aa-120 (50.00 mmol, 13.80 g), bb-14 (55.00 mmol, 13.49 g), tris(dibenzylacetone)palladium (1.00 mmol, 0.92 g), tri-tert-butylphosphine (2.00 mmol, 0.40 g), sodium tert-butoxide (100.00 mmol, 9.61 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. The mixture was recrystallized from toluene to give cc-120 (17.61 g, 80% yield). The purity of the solid was ≥99.77% as determined by HPLC.

[0195] Under nitrogen protection, cc-120 (30.00 mmol, 13.21 g), bb-24 (65.00 mmol, 14.25 g), palladium acetate (1.20 mmol, 0.27 g), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (2.40 mmol, 1.14 g), sodium tert-butoxide (120.00 mmol, 11.53 g), and 300 mL of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 5.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. The mixture was recrystallized from toluene to give compound 120 (15.96 g, yield 66%). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 805.3469 (theoretical value: 805.3457). Theoretical element content (%) C 60 H 43 N3: C, 89.41; H, 5.38; N, 5.21. Measured elemental content (%): C, 89.38; H, 5.40; N, 5.20.

[0196] [Synthetic Example 11] Synthesis of Compound 133

[0197]

[0198] Following the preparation method of Synthesis Example 1, aa-1 was replaced with an equimolar amount of aa-133, and bb-1 was replaced with an equimolar amount of bb-24, yielding compound 133 (15.21 g, 65%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 779.3316 (theoretical value: 779.3300). Theoretical elemental content (%) C 58 H 41 N3: C, 89.31; H, 5.30; N, 5.39. Measured element content (%): C, 89.28; H, 5.28; N, 5.43.

[0199] [Synthetic Example 12] Synthesis of Compound 169

[0200]

[0201] Following the preparation method of Synthesis Example 2, bb-1 was replaced with an equimolar amount of bb-169, and dd-8 was replaced with an equimolar amount of bb-1, yielding compound 169 (15.92 g, 67%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 791.4097 (theoretical value: 791.4085). Theoretical elemental content (%) C 58 H 33 D 10N3: C, 87.95; H, 6.74; N, 5.31. Measured elemental content (%): C, 87.91; H, 6.73; N, 5.38.

[0202] [Synthetic Example 13] Synthesis of Compound 175

[0203]

[0204] Following the preparation method of Synthesis Example 1, bb-1 was replaced with an equimolar amount of bb-175 to obtain compound 175 (17.29 g, 66%), with a solid purity ≥99.96% as determined by HPLC. Mass spectrometry m / z: 872.4723 (theoretical value: 872.4711). Theoretical elemental content (%) C 64 H 32 D 15 N3: C, 88.03; H, 7.15; N, 4.81. Measured elemental content (%): C, 88.05; H, 7.14; N, 4.85.

[0205] [Synthetic Example 14] Synthesis of Compound 221

[0206]

[0207] Following the preparation method of Synthesis Example 1, bb-1 was replaced with an equimolar amount of bb-221 to obtain compound 221 (15.62 g, 65%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 800.4628 (theoretical value: 800.4619). Theoretical elemental content (%) C 58 H 20 D 21 N3: C, 86.96; H, 7.80; N, 5.25. Measured elemental content (%): C, 86.97; H, 7.85; N, 5.23.

[0208] [Synthetic Example 15] Synthesis of Compound 228

[0209]

[0210] Following the preparation method of Synthesis Example 1, aa-1 was replaced with an equimolar amount of aa-133, and bb-1 was replaced with an equimolar amount of bb-228, yielding compound 228 (13.16 g, 68%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 644.3785 (theoretical value: 644.3772). Theoretical elemental content (%) C 46 H 20 D 15N3: C, 85.67; H, 7.81; N, 6.52. Measured element content (%): C, 85.66; H, 7.85; N, 6.54.

[0211] [Synthetic Example 16] Synthesis of Compound 267

[0212]

[0213] Following the preparation method of Synthesis Example 6, dd-40 was replaced with an equimolar amount of dd-267 to obtain compound 267 (14.78 g, 64%), with a solid purity ≥99.97% as determined by HPLC. Mass spectrometry m / z: 769.3447 (theoretical value: 769.3457). Theoretical elemental content (%) C 57 H 43 N3: C, 88.91; H, 5.63; N, 5.46. Measured elemental content (%): C, 88.95; H, 5.61; N, 5.47.

[0214] [Synthetic Example 17] Synthesis of Compound 302

[0215]

[0216] Following the preparation method of Synthesis Example 1, aa-1 was replaced with an equimolar amount of aa-133, and bb-1 was replaced with an equimolar amount of dd-267, yielding compound 302 (14.85 g, 66%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 749.3785 (theoretical value: 749.3770). Theoretical elemental content (%) C 55 H 47 N3: C, 88.08; H, 6.32; N, 5.60. Measured elemental content (%): C, 88.05; H, 6.33; N, 5.61.

[0217] [Synthetic Example 18] Synthesis of Compound 339

[0218]

[0219] Following the method for preparing cc-8 in Synthesis Example 2, aa-8 was replaced with an equimolar amount of aa-339, and bb-1 was replaced with an equimolar amount of bb-24 to obtain compound cc-339 (24.18 g, yield 81%). The solid purity was ≥99.66% as determined by HPLC.

[0220] Under nitrogen protection, cc-339 (30.00 mmol, 17.91 g), dd-339 (35.0 mmol, 12.78 g), potassium carbonate (45.00 mmol, 6.22 g), and Pd2(dba)3 (0.30 mmol, 0.27 g) were added to a reaction flask. 200 mL of a toluene / ethanol / water (2:1:1) mixed solvent was added, and the mixture was stirred. The reaction system was heated under reflux for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 339 (16.67 g, 63%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 881.3761 (theoretical value: 881.3770). Theoretical elemental content (%) C 66 H 47 N3: C, 89.87; H, 5.37; N, 4.76. Measured elemental content (%): C, 89.88; H, 5.38; N, 4.75.

[0221] [Synthetic Example 19] Synthesis of Compound 341

[0222]

[0223] Following the preparation method of Synthetic Example 18, aa-339 was replaced with an equimolar amount of aa-84, bb-24 with an equimolar amount of bb-14, and dd-339 with an equimolar amount of dd-341, yielding compound 341 (17.55 g, 64%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 913.4385 (theoretical value: 913.4396). Theoretical elemental content (%) C 68 H 55 N3: C, 89.34; H, 6.06; N, 4.60. Measured elemental content (%): C, 89.33; H, 6.05; N, 4.65.

[0224] [Synthetic Example 20] Synthesis of Compound 351

[0225]

[0226] Under nitrogen protection, aa-351 (50.00 mmol, 13.80 g), bb-351 (55.00 mmol, 15.90 g), potassium carbonate (75.00 mmol, 10.37 g), and Pd2(dba)3 (0.50 mmol, 0.46 g) were added to a reaction flask, along with 300 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene to give compound cc-351 (17.39 g, 79%). The purity of the solid was ≥99.74% as determined by HPLC.

[0227] Following the method used to prepare compound 120 in Synthesis Example 10, cc-120 was replaced with an equimolar amount of cc-351, and bb-24 was replaced with an equimolar amount of dd-351, yielding compound 351 (14.51 g, 60%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 805.3447 (theoretical value: 805.3457). Theoretical elemental content (%) C 60 H 43 N3: C, 89.41; H, 5.38; N, 5.21. Measured elemental composition (%): C, 89.43; H, 5.33; N, 5.23. [Synthesis Example 21] Synthesis of compound 358

[0228]

[0229] Following the preparation method of Synthesis Example 20, bb-351 was replaced with an equimolar amount of bb-358, and dd-351 was replaced with an equimolar amount of bb-1, yielding compound 358 (16.62 g, 61%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 907.3938 (theoretical value: 907.3926). Theoretical elemental content (%) C 68 H 49 N3: C, 89.93; H, 5.44; N, 4.63. Measured elemental content (%): C, 89.95; H, 5.47; N, 4.60.

[0230] [Synthetic Example 22] Synthesis of Compound 363

[0231]

[0232] Following the preparation method of Synthetic Example 20, aa-351 was replaced with an equimolar amount of aa-120, bb-351 with an equimolar amount of bb-363, and dd-351 with an equimolar amount of bb-1, yielding compound 363 (15.25 g, 65%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 781.3466 (theoretical value: 781.3457). Theoretical elemental content (%) C 58 H 43 N3: C, 89.08; H, 5.54; N, 5.37. Measured elemental content (%): C, 89.05; H, 5.51; N, 5.38.

[0233] [Synthetic Example 23] Synthesis of Compound 367

[0234]

[0235] Following the preparation method of Synthetic Example 18, cc-339 was replaced with an equimolar amount of cc-8, and dd-339 was replaced with an equimolar amount of dd-367, yielding compound 367 (17.25 g, 67%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 857.3785 (theoretical value: 857.3770). Theoretical elemental content (%) C 64 H 47 N3: C, 89.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 89.61; H, 5.51; N, 4.89.

[0236] [Synthetic Example 24] Synthesis of Compound 382

[0237]

[0238] Following the preparation method of Synthetic Example 18, bb-24 was replaced with an equimolar amount of bb-1, and dd-339 was replaced with an equimolar amount of dd-382, yielding compound 382 (17.16 g, 63%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 907.3938 (theoretical value: 907.3926). Theoretical elemental content (%) C 68 H 49 N3: C, 89.93; H, 5.44; N, 4.63. Measured elemental content (%): C, 89.95; H, 5.43; N, 4.61.

[0239] [Synthetic Example 25] Synthesis of Compound 389

[0240]

[0241] Following the preparation method of Synthesis Example 24, dd-382 was replaced with an equimolar amount of dd-389 to obtain compound 389 (17.51 ​​g, 68%), with a solid purity ≥99.96% as determined by HPLC. Mass spectrometry m / z: 857.3781 (theoretical value: 857.3770). Theoretical elemental content (%) C 64 H 47 N3: C, 89.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 89.59; H, 5.53; N, 4.87.

[0242] [Synthetic Example 26] Synthesis of Compound 398

[0243]

[0244] Following the preparation method of Synthetic Example 20, aa-351 was replaced with an equimolar amount of aa-120, bb-351 with an equimolar amount of bb-398, and dd-351 with an equimolar amount of bb-1, yielding compound 398 (15.31 g, 63%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 809.3716 (theoretical value: 809.3708). Theoretical elemental content (%) C 60 H 39 D4N3: C, 88.96; H, 5.85; N, 5.19. Measured elemental content (%): C, 88.95; H, 5.88; N, 5.18.

[0245] [Synthetic Example 27] Synthesis of Compound 405

[0246]

[0247] Under nitrogen protection, aa-8 (50.00 mmol, 16.02 g), bb-405 (105.00 mmol, 35.62 g), potassium carbonate (150.00 mmol, 20.73 g), and Pd2(dba)3 (1.00 mmol, 0.92 g) were added to a reaction flask, along with 300 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 7.5 hours. After the reaction was complete, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The obtained solid was recrystallized from toluene to give compound cc-405 (29.22 g, 78%). The purity of the solid was ≥99.70% as determined by HPLC.

[0248] Following the method used to prepare compound 8 in Synthesis Example 2, cc-8 was replaced with an equimolar amount of cc-405, and dd-8 was replaced with an equimolar amount of bb-1, yielding compound 405 (16.94 g, 64%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 881.3780 (theoretical value: 881.3770). Theoretical elemental content (%) C 66 H 47 N3: C, 89.87; H, 5.37; N, 4.76. Measured elemental content (%): C, 89.88; H, 5.38; N, 4.73.

[0249] [Synthetic Example 28] Synthesis of Compound 412

[0250]

[0251] Under nitrogen protection, aa-1 (50.00 mmol, 18.24 g), bb-412 (155.00 mmol, 44.82 g), potassium carbonate (225.00 mmol, 31.10 g), and Pd2(dba)3 (1.50 mmol, 1.37 g) were added to a reaction flask, along with 300 mL of a toluene / ethanol / water (2:1:1) mixed solvent. The mixture was stirred, and the reaction system was heated under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out at a lower temperature, and the solid was filtered. The resulting solid was recrystallized from toluene to give compound 412 (16.73 g, 65%). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrometry m / z: 857.3762 (theoretical value: 857.3770). Theoretical elemental content (%) C 64 H 47 N3: C, 89.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 89.59; H, 5.51; N, 4.95.

[0252] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0253] The following are compounds other than those shown in formula (I) used in the device fabrication examples:

[0254]

[0255]

[0256] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 15 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using the McScience M6000 OLED lifetime testing system, the lifetime (brightness decaying to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature. The test results are shown in Tables 1 to 4.

[0257] Comparative device fabrication example 1: Comparative device 1

[0258] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0259] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HATCN as a hole injection layer with a thickness of 10 nm; b) HTM-1 as a hole transport layer with a thickness of 40 nm; c) TBADN and BD (mass ratio of 97:3) as a light-emitting layer with a thickness of 30 nm; d) TPBi as a hole blocking layer with a thickness of 20 nm; e) NBphen and Liq (mass ratio of 5:1) as an electron transport layer with a thickness of 25 nm; f) LiF as an electron injection layer with a thickness of 0.2 nm; g) Mg and Ag (mass ratio of 7:3) as a cathode with a thickness of 15 nm; h) CP-4 as a capping layer with a thickness of 80 nm.

[0260] Comparative device fabrication examples 2-5: Comparative devices 2-5

[0261] By replacing HTM-1 in the hole transport layer with HTM-2, HTM-3, HTM-4 and HTM-5 respectively, and following the same steps as in Comparative Device Preparation Example 1, Comparative Devices 2 to 5 can be obtained.

[0262] Device fabrication examples 1-28: Light-emitting devices 1-28

[0263] By replacing HTM-1 in the hole transport layer with the aromatic amine compounds of the present invention synthesized in Examples 1 to 28, and with all other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 1 to 28 can be obtained.

[0264] Table 1

[0265]

[0266]

[0267] Comparative device fabrication example 6: Comparative device 6

[0268] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0269] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-3 and p-1 (mass ratio 100:5) as hole injection layer with a thickness of 20 nm; b) HT-3 as hole transport layer with a thickness of 35 nm; c) HTM-2, GH and Ir(mppy)3 (mass ratio 48:48:4) as light-emitting layer with a thickness of 35 nm; d) TPBi as hole blocking layer with a thickness of 25 nm; e) NBphen and Liq (mass ratio 4:1) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 0.3 nm; g) Mg and Ag (mass ratio 7:3) as cathode with a thickness of 10 nm; h) CP-4 as capping layer with a thickness of 100 nm.

[0270] Comparative device fabrication examples 7-9: Comparative devices 7-9

[0271] By replacing HTM-2 in the light-emitting layer with HTM-3, HTM-4 and HTM-5 respectively, and following the same steps as in Comparative Device Preparation Example 6, Comparative Devices 7 to 9 can be obtained.

[0272] Device fabrication examples 29-56: Light-emitting devices 29-56

[0273] By replacing HTM-2 in the light-emitting layer with the aromatic amine compounds of the present invention synthesized in Examples 1 to 28, and with all other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 29 to 56 can be obtained.

[0274] Table 2

[0275]

[0276]

[0277] Comparative device fabrication example 10: Comparative device 10

[0278] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0279] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) HT-3 and p-1 (mass ratio 100:5) as hole injection layer with a thickness of 35 nm; b) HT-3 as hole transport layer with a thickness of 35 nm; c) RH-1, RH-2 and Ir(2-phq)2(acac) (mass ratio 64:32:4) as light-emitting layer with a thickness of 30 nm; d) TPBi as hole blocking layer with a thickness of 25 nm; e) NBphen and Liq (mass ratio 5:3) as electron transport layer with a thickness of 25 nm; f) LiF as electron injection layer with a thickness of 0.1 nm; g) Mg and Ag (mass ratio 1:1) as cathode with a thickness of 15 nm; h) CP-2 as capping layer with a thickness of 90 nm.

[0280] Device fabrication examples 57-84: Light-emitting devices 57-84

[0281] By replacing CP-2 in the capping layer with the aromatic amine compounds of the present invention synthesized in Examples 1 to 28, and with all other steps being the same as in Comparative Device Preparation Example 1, light-emitting devices 57 to 84 can be obtained.

[0282] Table 3

[0283]

[0284]

[0285] Comparative device fabrication example 11: Comparative device 11

[0286] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0287] The following layers were deposited layer by layer on the aforementioned ITO / Ag / ITO glass substrate: a) 2-TNATA as a hole injection layer with a thickness of 50 nm; b) HT-3 as a hole transport layer with a thickness of 45 nm; c) HTM-1 as a light-emitting auxiliary layer with a thickness of 35 nm; d) RH-1, RH-2, and Ir(2-phq)2(acac) (mass ratio of 64:32:4) as a light-emitting layer with a thickness of 35 nm; e) NBphen and Liq (mass ratio of 4:1) as an electron transport layer with a thickness of 35 nm; f) LiF as an electron injection layer with a thickness of 0.2 nm; g) Mg and Ag (mass ratio of 3:7) as a cathode with a thickness of 12 nm; h) CP-2 as a capping layer with a thickness of 100 nm.

[0288] Comparative device fabrication examples 12-15: Comparative devices 12-15

[0289] By replacing HTM-1 in the light-emitting auxiliary layer with HTM-2, HTM-3, HTM-4 and HTM-5 respectively, and following the same steps as in Comparative Device Preparation Example 11, Comparative Devices 12 to 15 can be obtained.

[0290] Device fabrication examples 85-112: Light-emitting devices 85-112

[0291] By replacing HTM-1 in the light-emitting auxiliary layer with the aromatic amine compounds of the present invention synthesized in Examples 1 to 28, and with all other steps being the same as in Comparative Device Preparation Example 14, light-emitting devices 85 to 112 can be obtained.

[0292] Table 4

[0293]

[0294]

[0295] The device data in Tables 1 to 4 show that when the aromatic amine compounds described in this invention are used as the hole transport layer, the main material of the light-emitting layer, the capping layer, and the light-emitting auxiliary layer, the driving voltage, luminous efficiency, and lifespan of the device are significantly improved. This indicates that the aromatic amine compounds described in this invention are a class of high-performance OLED materials with excellent application prospects.

[0296] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. An aromatic amine compound, characterized in that, The aromatic amine compound has the structure shown in formula (I): Wherein, L1~L9 are independently selected from a single bond or one of the following structures: Wherein, the a 11 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the b mentioned 11 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the c mentioned 11 Each time it appears, it is selected from 0, 1, or 2, either identically or differently; the d mentioned 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the e 11 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different. The R 11 Each time it appears, it is selected from the same or different groups of hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1 to C4 straight-chain or branched alkyl group; Each time a1 appears, it is selected from 0, 1, or 2, either the same or different. Each time b1 appears, it is selected from 0, 1, 2, 3 or 4, either the same or different. Each time R1 appears, it is selected from one of hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted C1-C6 straight-chain or branched alkyl groups, either the same or different. Ar1 to Ar6 are independently selected from one of the following structures: Wherein, the a 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, or 5, either identically or differently; the b mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, or 4, either identically or differently; the c mentioned 21 Each time it appears, it is selected from 0, 1, 2, or 3, either identically or differently; the e 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, or 6, either identically or differently; the f mentioned 21 Each time it appears, it is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, either the same or different. The R 21 Each time it appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, or substituted or unsubstituted C6-C12 aryl group. The R 22 R 23 It is independently selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted sec-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; The substituent in "substituted or unsubstituted" is selected from one or more of the following groups: deuterium atom; halogen atom; cyano group; and a C1-C6 straight-chain or branched alkyl group substituted or unsubstituted by one or more of the following groups: deuterium atom, halogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, and deuterated tert-butyl. The substituent may be one or more, and when there are multiple substituents, the multiple substituents may be the same or different. The aromatic amine compound is not .

2. The aromatic amine compound according to claim 1, characterized in that, The L1 to L9 are independently selected from a single bond or one of the following structures: 。 3. The aromatic amine compound according to claim 1, characterized in that, Each time R1 appears, it is selected from one of the following, either the same or different: hydrogen atom, deuterium atom, fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted sec-butyl group, and substituted or unsubstituted tert-butyl group.

4. The aromatic amine compound according to claim 1, characterized in that, The Ar1 to Ar6 are independently selected from one of the following structures: 。 5. The aromatic amine compound according to claim 1, characterized in that, The aromatic amine compound has the structure shown in formula (IA): Wherein, L1~L9 and Ar1~Ar6 are all as described in claim 1.

6. The aromatic amine compound according to claim 1, characterized in that, The aromatic amine compounds have the structures shown in formulas (IB) to (IG): Wherein, L1~L9 and Ar1~Ar6 are all as described in claim 1.

7. An aromatic amine compound, characterized in that, The aromatic amine compound is selected from one of the following structures: 。 8. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, characterized in that, The organic layer contains the aromatic amine compound as described in claim 1.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic electroluminescent device further includes a capping layer, which is located on the side of the cathode away from the anode or on the side of the anode away from the cathode.

10. An organic electroluminescent device, comprising an anode, a cathode, an organic layer located between the anode and the cathode, and a capping layer, wherein the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region, and the capping layer is located on the side of the cathode away from the anode or on the side of the anode away from the cathode, characterized in that, The coating layer contains the aromatic amine compound as described in claim 1.

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