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 thermal stability and chemical stability, can resist high temperature and corrosive gas, thereby prolonging the service life of device;Molecule also has proper rigidity and fluidity, thereby having good film-forming property, good fluidity in film-forming process, can form more smooth surface, further improve the luminous efficiency and service life of device.Summarized above, the arylamine compound provided by the present application can be applied to OLED device as hole transport material, host material of light-emitting layer and cover layer material.

Description

Technical Field

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

[0002] Organic Light-Emitting Diode (OLED) has the advantages of light weight, small size, wide viewing angle, fast response, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity, and good flexibility. It can meet consumers' new demands for display technology and has good application prospects in the fields of lighting and display.

[0003] Classic OLED devices have a "sandwich" structure, with a light-emitting layer containing a luminescent substance sandwiched between two electrodes, the cathode and the anode. When a voltage is applied between the two electrodes, electrons and holes are injected from the cathode and anode, respectively, and recombine in the light-emitting layer to form excitons, releasing energy. The excitons migrate, transferring the energy to the guest material, and the electrons in the molecules of the guest material transition from the ground state to the excited state. Because the excited state is unstable, the electrons migrate back from the excited state to the stable ground state, releasing energy in the form of light, resulting in luminescence. To improve the driving voltage, luminous efficiency, color purity, and service life of OLED devices, additional organic functional layers are added between the anode and the light-emitting layer, and between the cathode and the light-emitting layer. Generally, the organic functional layer between the anode and the light-emitting layer injects and transports holes and is called the hole transport region; the organic functional layer between the cathode and the light-emitting layer injects and transports electrons and is called the electron transport region. The hole transport region includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, and a light-assisting layer. The electron transport region includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer. To further improve device performance such as luminous efficiency and service life, a capping layer is often provided on the outside of at least one electrode.

[0004] Hole transport materials generally require high hole mobility, appropriate highest occupied molecular orbital (HOMO) and triplet energy levels (T1), good stability, and film-forming properties. Host materials generally require a higher LUMO value and a lower HOMO value than the guest material. Aromatic amine compounds are among the most widely used OLED materials. These compounds possess the properties expected of the aforementioned hole transport materials, and aromatic amine compounds of different structures exhibit varying performance. They can be used in OLED devices as hole transport functional layers, host materials for the light-emitting layer, or as cover layers. Summary of the Invention

[0005] To solve the above technical problems, the present invention provides an aromatic amine compound having high hole mobility, appropriate HOMO and T1 values, and can be used as a hole transport material, a host material for a light-emitting layer, and a cover layer material, all of which can achieve excellent device performance. The aromatic amine compound has a structure shown in formula (I):

[0006]

[0007] wherein said L1 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and said L1 to L3 are not selected from a single bond at the same time;

[0008] Each occurrence of a1 is identical or different and is selected from 0, 1, 2 or 3;

[0009] Each occurrence of R1 is identical or different and is selected from one of the following groups: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring;

[0010] The Ar1 to Ar6 are independently selected from substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, and groups formed by fusion of substituted or unsubstituted C6 to C30 aromatic rings and substituted or unsubstituted C5 to C7 aliphatic rings;

[0011] The condition is that at least one of L1 to L9, R1, and Ar1 to Ar6 contains a group formed by the fusion of a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, or a divalent group formed by the fusion of a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring.

[0012] Beneficial effects:

[0013] The aromatic amine compound represented by formula (I) provided by the present invention has excellent hole migration ability and has appropriate HOMO and T1 values. When used as a hole transport material in an OLED device, it can improve the hole transport efficiency. When combined with other functional layers, it can improve the luminous efficiency of the device. It also has excellent thermal stability and chemical stability, is resistant to high temperatures and corrosive gases, and thus extends the service life of the device. Since the molecule contains aromatic ring and aliphatic ring fused groups but no deuterium atoms, the molecule has appropriate rigidity and fluidity, and thus has excellent film-forming properties. The good fluidity during the film-forming process can form a smoother surface, further improving the luminous efficiency and service life of the device.

[0014] In summary, the aromatic amine compounds provided by the present invention have good charge transfer ability, stability and film-forming properties, and have appropriate energy levels, and can be used as hole transport materials, host materials of light-emitting layers, and covering layer materials in OLED devices. DETAILED DESCRIPTION

[0015] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0016] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes atoms at both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain approximately 0.0156 atomic % deuterium per hydrogen atom.

[0017] As used herein, the use of "H" and "hydrogen atoms" means that the hydrogen atoms in a chemical structure contain no more than natural abundance of deuterium atoms or tritium atoms, for example, no more than 0.0156 atomic % of deuterium. "D" and "deuterium atoms" mean that the abundance of deuterium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is deuterium. "T" and "tritium atoms" mean that the abundance of tritium content is above natural abundance, for example, any value exceeding 0.1 atomic %, exceeding 1 atomic %, or exceeding 10 atomic %, for example, wherein about 95 atomic % is tritium. As used herein, hydrogen atoms not shown are omitted to represent "H" or "hydrogen".

[0018] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0019] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing 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, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but is not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

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

[0021] The cycloalkenyl group herein refers to a hydrocarbon group formed by removing a 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 include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and cycloheptenyl. The cycloalkyl group is preferably cyclopentenyl or cyclohexenyl.

[0022] The cycloalkynyl group of the present invention refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkyne molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples include, but are not limited to, cyclopropynyl, cyclobutynyl, cyclopentynyl, cyclohexynyl, and cycloheptynyl. The cycloalkyl group is preferably cyclopentynyl or cyclohexynyl.

[0023] The heterocyclic group described herein refers to a group formed by removing a hydrogen atom from a heterocyclic molecule containing at least one heteroatom in addition to carbon atoms. Heteroatoms include nitrogen, oxygen, sulfur, and silicon atoms, with nitrogen, oxygen, and sulfur atoms being preferred. Preferably, the group contains 1 to 3 heteroatoms, more preferably 1 to 2 heteroatoms, and particularly preferably 1 heteroatom. Preferably, the group contains 3 to 15 ring atoms, more preferably 3 to 12 ring atoms, and particularly preferably 5 to 6 ring atoms. Examples include, but are not limited to, oxiranyl, thiothianyl, propidinyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl. Preferred heterocyclic groups are tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, and piperazinyl.

[0024] The aryl group described in the present invention refers to a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. It can be a monocyclic aryl group, a polycyclic aryl group, or a condensed aryl group, 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 group refers to an aryl group with only one aromatic ring in the molecule, such as, but not limited to, phenyl; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as, but not limited to, biphenyl and terphenyl; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as, but not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, etc. The above-mentioned aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0025] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is 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 attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, triazine, furyl, thienyl, pyrrolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited to. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, benzodibenzothienyl, benzodibenzofuranyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, or phenoxathiyl.

[0026] The group formed by the fusion of an aromatic ring and an aliphatic ring of the present invention refers to a general term for a monovalent group formed by removing a hydrogen atom from an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) fused together. The aromatic ring preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, most preferably 6 to 12 carbon atoms, and may include benzene, naphthalene, anthracene, phenanthrene, etc., but is not limited thereto; the aliphatic ring preferably has 3 to 9 carbon atoms, more preferably 5 to 7 carbon atoms, and may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclopropyne, cyclobutyne, cyclopentyne, cyclohexyne, and cycloheptyne. Preferably, examples of the group formed by the condensation of an aromatic ring and an aliphatic ring may include, but are not limited to, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, and the like.

[0027] The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0028] The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the heteroaryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0029] The divalent group formed by the fusion of an aromatic ring and an aliphatic ring described herein 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. The description of the group formed by the fusion of an aromatic ring and an aliphatic ring provided above applies, except that the divalent group formed by the fusion of an aromatic ring and an aliphatic ring is a divalent group.

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

[0031] The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of: halogen atoms, amino groups, cyano groups, nitro groups, substituted or unsubstituted C1-C30 alkyl groups, substituted or unsubstituted C1-C30 alkenyl groups, substituted or unsubstituted C1-C30 alkynyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, substituted or unsubstituted C3-C30 cycloalkenyl groups, substituted or unsubstituted C3-C30 cycloalkyl groups, Alkynyl, substituted or unsubstituted C3-C30 heterocyclic group, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted silyl, preferably a deuterium atom, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocyclic group, C6-C30 aromatic alkyl, C3-C30 heteroaryl, silyl, when substituted by multiple substituents, the multiple substituents are the same or different; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, norbornyl, methyl Oxy, ethoxy, phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, trimethylsilyl, triphenylsilyl. When substituted with multiple substituents, the multiple substituents may be the same or different.

[0032] In the manual, It means the portion to which another substituent is attached. Can be attached to any optional position of the attached group / fragment. express And so on.

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

[0034] The ring structure formed by the connection of the present invention means that the groups are connected to each other by chemical bonds, and optionally form double bonds / triple bonds, and can constitute aromatic groups, as shown in the following example:

[0035]

[0036] In the present invention, the ring formed by the bonding may be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two, and may 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, cyclopentane acene, cyclohexene, cyclohexane, cycloheptene, cycloheptane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but are not limited thereto.

[0037] In addition, two groups attached to the same nitrogen atom can be linked to form a ring, as shown in the following example:

[0038]

[0039] In the present invention, the ring formed by two groups connected to the same nitrogen atom can be carbazole, and a group in which one or two benzene rings of carbazole are fused with a benzene ring or a naphthalene ring.

[0040] The present invention provides an aromatic amine compound having a structure shown in formula (I):

[0041]

[0042] wherein said L1 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and said L1 to L3 are not selected from a single bond at the same time;

[0043] Each occurrence of a1 is identical or different and is selected from 0, 1, 2 or 3;

[0044] Each occurrence of R1 is identical or different and is selected from one of the following groups: a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring;

[0045] Ar1 to Ar6 are independently selected from a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring;

[0046] The condition is that at least one of L1 to L9, R1, and Ar1 to Ar6 contains a group formed by the fusion of a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, or a divalent group formed by the fusion of a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring.

[0047] Preferably, the substituent in the "substituted or unsubstituted" is selected from halogen atoms; cyano groups; C1-C12 straight-chain or branched alkyl groups substituted or unsubstituted by one or more of the group consisting of halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, phenyl groups, naphthyl groups, and biphenyl groups; or C1-C12 straight-chain or branched alkyl groups substituted or unsubstituted by one or more of the group consisting of halogen atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, phenyl groups, naphthyl groups, and biphenyl groups. a substituted or unsubstituted C3-C12 cycloalkyl group; a C3-C12 cycloalkenyl group substituted or unsubstituted by one or more selected from the group consisting of a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; a C6-C30 aryl group substituted or unsubstituted by one or more selected from the group consisting of a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; a C2-C30 heteroaryl group substituted or unsubstituted by one or more selected from the group consisting of a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group; a group formed by a C6-C30 aromatic ring substituted or unsubstituted by one or more selected from the group consisting of a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group, and a substituted or unsubstituted C3-C7 aliphatic ring; a silyl group substituted or unsubstituted by one or more selected from the group consisting of a halogen atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a phenyl group, a naphthyl group, and a biphenyl group, wherein the substituents are one or more; when there are multiple substituents, the multiple substituents may be the same or different; when there are multiple substituents, two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C7 carbocyclic ring.

[0048] Preferably, the substituent in the "substituted or unsubstituted" is selected from methyl; ethyl; n-propyl; isopropyl; n-butyl; sec-butyl; isobutyl; tert-butyl; cyclopropyl substituted or unsubstituted by one or more of the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, biphenyl; cyclobutanyl substituted or unsubstituted by one or more of the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, biphenyl; cyclopentanyl substituted or unsubstituted by one or more of the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, biphenyl; cyclohexyl substituted or unsubstituted by one or more of the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, biphenyl; alkyl; cyclopropenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; cyclobutenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; cyclopentenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; cyclohexenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; methyl sulfonyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; Norbornyl; norbornyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; phenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; naphthyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; anthracenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; phenanthrenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; triphenylene substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; fluorenyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; dibenzofuranyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; carbazolyl substituted or unsubstituted by one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl;Indanyl substituted or unsubstituted with one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; tetralinyl substituted or unsubstituted with one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl; Silyl substituted or unsubstituted with one or more selected from the group consisting of methyl, ethyl, isopropyl, n-butyl, tert-butyl, phenyl, naphthyl, and biphenyl, wherein the substituents are one or more. When there are multiple substituents, the multiple substituents may be the same or different. When there are multiple substituents, two adjacent substituents may be linked to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbocyclic ring.

[0049] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures, and L1 to L3 are not selected from a single bond at the same time:

[0050]

[0051] Among them, the a 11 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 11 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said c 11 Each occurrence is identically or differently selected from 0, 1 or 2; said d 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said e 11 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;

[0052] The R 11 Each time it occurs, it is selected, identically or differently, from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C4 straight-chain or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C12 aryl group, or a group formed by a substituted or unsubstituted C6-C12 aromatic ring fused with a substituted or unsubstituted C5-C7 aliphatic ring.

[0053] Preferably, the R 11each occurrence is identically or differently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, phenyl substituted or unsubstituted with one or more of the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; phenyl substituted or unsubstituted with one or more of the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropyl, cyclobutane, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl; a naphthyl group which is unsubstituted or substituted with one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a biphenyl group which is unsubstituted or substituted with one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group.

[0054] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures, and L1 to L3 are not selected from a single bond at the same time:

[0055]

[0056] Preferably, L1 to L9 are independently selected from a single bond or one of the following structures, and L1 to L3 are not selected from a single bond at the same time:

[0057]

[0058]

[0059] Preferably, one of L1 to L3 is not a single bond, and the others are single bonds. More preferably, L1, L2 or L3 is not a single bond, and the others are single bonds.

[0060] Preferably, two of L1 to L3 are not single bonds, and the rest are single bonds. More preferably, L1 and L2, L1 and L3, or L2 and L3 are not single bonds, and the rest are single bonds.

[0061] Preferably, L1 to L3 are not selected from single bonds.

[0062] Preferably, each occurrence of R1 is identical or different and is selected from one of hydrogen 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 cyclopropanyl group, substituted or unsubstituted cyclobutanyl group, substituted or unsubstituted cyclopentanyl group, substituted or unsubstituted cyclohexanyl group, substituted or unsubstituted cycloheptyl group, substituted or unsubstituted cyclopropenyl group, substituted or unsubstituted cyclobutenyl group, substituted or unsubstituted cyclopentenyl group, substituted or unsubstituted cyclohexenyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted indanyl group, substituted or unsubstituted tetrahydronaphthyl group.

[0063] Preferably, each occurrence of R1 is identical or different and is selected from the group consisting of hydrogen 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; trifluoromethyl group; cyclopropyl group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornyl group; cyclopropyl group, cyclobutyl group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornyl group; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, trifluoromethyl group, cyclopropyl group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornyl group. alkyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl substituted or unsubstituted cyclobutanyl; cyclopentanyl substituted or unsubstituted by one or more of the group consisting of fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl substituted or unsubstituted; cyclopentanyl substituted or unsubstituted by one or more of the group consisting of fluorine atom, chlorine atom, bromine atom, iodine atom, cyano group, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl substituted or unsubstituted; Cyclohexanyl substituted or unsubstituted by one or more groups selected from the group consisting of cyclohexenyl, adamantyl, and norbornyl; cycloheptanyl substituted or unsubstituted by one or more groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl; cycloheptanyl substituted or unsubstituted by one or more groups selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl adamantyl group substituted or unsubstituted with one or more of the group consisting of: a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a phenyl group substituted or unsubstituted with one or more of the group consisting of: a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group;a naphthyl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a naphthyl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; an indanyl group which may be substituted or unsubstituted by one or more of the group consisting of an alkyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; or a tetrahydronaphthyl group which may be substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group.

[0064] Preferably, each occurrence of R1 is identical or different and is selected from a hydrogen atom, a fluorine atom, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group or one of the following structures:

[0065]

[0066] Preferably, at least one of the Ar1 to Ar6 groups is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and the rest are independently selected from a substituted or unsubstituted C6 to C30 aromatic group and a substituted or unsubstituted C2 to C30 heteroaryl group.

[0067] Preferably, one of the Ar1 to Ar6 groups is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and the others are independently selected from a substituted or unsubstituted C6 to C30 aromatic group and a substituted or unsubstituted C2 to C30 heteroaromatic group.

[0068] Preferably, “one of the Ar1 to Ar6” includes Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6.

[0069] Preferably, two of the Ar1 to Ar6 are selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and the rest are independently selected from a substituted or unsubstituted C6 to C30 aromatic group and a substituted or unsubstituted C2 to C30 heteroaryl group.

[0070] Preferably, “two of the Ar1 to Ar6” include Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar4, Ar1 and Ar5, Ar1 and Ar6, Ar2 and Ar3, Ar2 and Ar4, Ar2 and Ar5, Ar2 and Ar6, Ar3 and Ar4, Ar3 and Ar5, Ar3 and Ar6, Ar4 and Ar5, Ar4 and Ar6, or Ar5 and Ar6.

[0071] Preferably, three of the Ar1 to Ar6 are selected from one of the groups formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring, and the rest are independently selected from one of a substituted or unsubstituted C6 to C30 aromatic group and a substituted or unsubstituted C2 to C30 heteroaryl group.

[0072] Preferably, “three of the Ar1 to Ar6” include Ar1, Ar2 and Ar3; Ar1, Ar2 and Ar4; Ar1, Ar2 and Ar5; Ar1, Ar2 and Ar6; Ar1, Ar3 and Ar4; Ar1, Ar3 and Ar5; Ar1, Ar3 and Ar6; Ar1, Ar4 and Ar5; Ar1, Ar4 and Ar6; Ar1, Ar5 and Ar6; Ar2, Ar3 and Ar4; Ar2, Ar3 and Ar5; Ar2, Ar3 and Ar6; Ar2, Ar4 and Ar5; Ar2, Ar4 and Ar6; Ar2, Ar5 and Ar6; Ar3, Ar4 and Ar5; Ar3, Ar4 and Ar6; Ar3, Ar5 and Ar6; or Ar4, Ar5 and Ar6.

[0073] Preferably, the Ar1 is selected from a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring, and the Ar2-Ar6 are independently selected from a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group.

[0074] Preferably, Ar1 and Ar3 are independently selected from one of the groups formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring, and Ar2 and Ar4-Ar6 are independently selected from one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group.

[0075] Preferably, Ar1, Ar3, and Ar5 are independently selected from one of the groups formed by the fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring, and Ar2, Ar4, and Ar6 are independently selected from one of a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C2-C30 heteroaryl group.

[0076] Preferably, the "group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring" in Ar1-Ar6 is selected from one of the following structures:

[0077]

[0078] Preferably, the groups in Ar1 to Ar6 that are not “a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring” are independently selected from one of the following structures:

[0079]

[0080] Among them, the a 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 21 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 21 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said d 21 Each occurrence is identically or differently selected from 0, 1 or 2; said e 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

[0081] The R 21 Each occurrence is the same or different selected from a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C4 straight or branched alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C12 aryl group, a group formed by condensing a substituted or unsubstituted C6-C12 aromatic ring and a substituted or unsubstituted C3-C7 aliphatic ring, or two adjacent R 21 They are connected to form a substituted or unsubstituted saturated or unsaturated C3-C6 carbon ring.

[0082] The R 22 、R 23 is independently selected from a hydrogen atom, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted sec-butyl group, a substituted or unsubstituted isobutyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted indanyl group, a substituted or unsubstituted tetrahydronaphthyl group, or said R 22 With R 23 connected to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbon ring;

[0083] The L 21 One selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, and a substituted or unsubstituted biphenylene group;

[0084] The R 24 One selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted indanyl, and substituted or unsubstituted tetrahydronaphthyl.

[0085] Preferably, the R 21each occurrence is identically or differently selected from the group consisting of hydrogen 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; trifluoromethyl group; cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornyl group; cyclopropane group, cyclobutane group, cyclopentenyl group, cyclohexenyl group, adamantyl group, and norbornyl group; , cycloheptanyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl substituted or unsubstituted cyclobutanyl; cyclopentanyl substituted or unsubstituted by one or more of the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, cyano groups, methyl groups, ethyl groups, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl groups, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclopentenyl, cyclohexenyl, adamantyl, and norbornyl substituted or unsubstituted cyclopentanyl; cyclopentanyl substituted or unsubstituted by one or more of the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, cyano groups, methyl groups, ethyl groups, n-propyl, isopropyl, n-butyl, tert-butyl, trifluoromethyl groups, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyl, cycloheptanyl, cyclopentenyl, cyclohexenyl, a cyclohexyl group which may be substituted or unsubstituted by one or more groups selected from the group consisting of adamantyl and norbornyl; a cycloheptyl group which may be substituted or unsubstituted by one or more groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptanyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and norbornyl; a cycloheptyl group which may be substituted or unsubstituted by one or more groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptanyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and norbornyl; One or more substituted or unsubstituted cyclopentenyl groups; cyclohexenyl groups substituted or unsubstituted by one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; adamantyl group substituted or unsubstituted by one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group;norbornyl group which may be substituted or unsubstituted by one or more groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; phenyl group which may be substituted or unsubstituted by one or more groups selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group ; naphthyl which may be substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; anthracenyl which may be substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutane group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a phenanthryl group which is substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a biphenyl group which is substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; an indanyl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; or a tetrahydronaphthyl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group.

[0086] Preferably, the R 22 、R 23substituted or unsubstituted phenyl groups selected from the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, trifluoromethyl groups, cyclopropyl groups, cyclobutanyl groups, cyclopentanyl groups, cyclohexanyl groups, cycloheptanyl groups, cyclopentenyl groups, cyclohexenyl groups, adamantyl groups, and norbornyl groups; substituted or unsubstituted naphthyl groups selected from the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, trifluoromethyl groups, cyclopropyl groups, cyclobutanyl groups, cyclopentanyl groups, cyclohexanyl groups, cycloheptanyl groups, cyclopentenyl groups, cyclohexenyl groups, adamantyl groups, and norbornyl groups; substituted or unsubstituted naphthyl groups selected from the group consisting of fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, cyano groups, methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, tert-butyl groups, trifluoromethyl groups, cyclopropyl groups, cyclobutanyl groups, cyclopentanyl groups, cyclohexanyl groups, cycloheptanyl groups, cyclopentenyl groups, cyclohexenyl groups, adamantyl groups, and norbornyl groups; a biphenyl group which may be substituted or unsubstituted by one or more selected from the group consisting of a butanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptanyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; an indanyl group which may be substituted or unsubstituted by one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptanyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a tetrahydronaphthyl group which may be substituted or unsubstituted by one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexanyl group, a cycloheptanyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group, or the R 22 With R 23 They are connected to form a substituted or unsubstituted saturated or unsaturated C3-C10 carbon ring.

[0087] Preferably, the L 21 Selected from a single bond or one of the following structures:

[0088]

[0089] Preferably, the L 21 Selected from a single bond or one of the following structures:

[0090]

[0091] Preferably, the R 24a phenyl group which may be substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a phenyl group which may be substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutane group a naphthyl group which is substituted or unsubstituted by one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; an anthracene ... a phenanthryl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, an adamantyl group, and a norbornyl group; a phenanthryl group which is substituted or unsubstituted with one or more of the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a trifluoromethyl group, a cyclopropyl group, a cyclobutane group, a cyclopentane group an indanyl group which is unsubstituted or substituted by one or more selected from the group consisting of an alkyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, adamantyl and norbornyl group; or a tetrahydronaphthyl group which is unsubstituted or substituted by one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a methyl group, an ethyl group, n-propyl, isopropyl, n-butyl, tert-butyl, a trifluoromethyl group, a cyclopropanyl group, a cyclobutanyl group, a cyclopentanyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, adamantyl and norbornyl group.

[0092] Preferably, the "group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring" in Ar1-Ar6 is selected from one of the following structures:

[0093]

[0094]

[0095] Preferably, the groups in Ar1 to Ar6 that are not “a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring” are independently selected from one of the following structures:

[0096]

[0097]

[0098]

[0099]

[0100] Preferably, the aromatic amine compound has a structure shown in formula (IA):

[0101]

[0102] Wherein, the L1 is selected from a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring;

[0103] The L4 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring;

[0104] Ar1 to Ar6 are independently selected from one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and groups formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring; and when Ar1 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L4 is selected from one of substituted or unsubstituted C6-C30 arylene groups, and divalent groups formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring; and when Ar2 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L5 is selected from one of substituted or unsubstituted C6-C30 arylene groups, and divalent groups formed by fusion of a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring;

[0105] Said a1 and R1 are as described in the present invention;

[0106] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0107] Preferably, the aromatic amine compound has a structure shown in formula (IB):

[0108]

[0109] Wherein, the L1 is selected from substituted or unsubstituted C6-C30 arylene groups;

[0110] The L4 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group;

[0111] The Ar1 to Ar6 are independently selected from one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring; and when Ar1 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L4 is selected from a substituted or unsubstituted C6-C30 arylene group; when Ar2 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L5 is selected from a substituted or unsubstituted C6-C30 arylene group;

[0112] Said a1 is as described in the present invention;

[0113] Each occurrence of R1 is the same or different and is selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group or one of the following structures:

[0114]

[0115] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0116] Preferably, the aromatic amine compound has a structure shown in formula (IC) or (ID):

[0117]

[0118] Wherein, the L1 to L3 are independently selected from a substituted or unsubstituted C6 to C30 arylene group, a divalent group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring;

[0119] Said L4-L9, Ar1-Ar6, a1, and R1 are as described in the present invention;

[0120] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0121] Preferably, the aromatic amine compound has a structure shown in Formula (IE) or Formula (IF):

[0122]

[0123] Wherein, L1 to L3 are independently selected from substituted or unsubstituted C6 to C30 arylene groups;

[0124] The L4 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group;

[0125] Said Ar1 to Ar6 and a1 are as described in the present invention;

[0126] Each occurrence of R1 is the same or different and is selected from a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group or one of the following structures:

[0127]

[0128] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0129] Preferably, the aromatic amine compound has a structure shown in formula (IG):

[0130]

[0131] Wherein, the L1 is selected from substituted or unsubstituted C6-C30 arylene groups;

[0132] The L4 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group;

[0133] The Ar1 to Ar6 are independently selected from one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, and a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring; and when Ar1 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L4 is selected from a substituted or unsubstituted C6-C30 arylene group; when Ar2 is selected from a substituted or unsubstituted C2-C30 heteroaryl group, L5 is selected from a substituted or unsubstituted C6-C30 arylene group;

[0134] Each occurrence of R1 is identical or different and is selected from one of hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, cyclopentanyl, cyclohexanyl, adamantyl, and norbornyl; preferably, each occurrence of R1 is identical or different and is selected from one of hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, cyclopentanyl, and cyclohexanyl;

[0135] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0136] Preferably, the aromatic amine compound has a structure shown in Formula (IJ) or Formula (IK):

[0137]

[0138] Wherein, said L1 to L3 are selected from substituted or unsubstituted C6 to C30 arylene groups;

[0139] The L4 to L9 are independently selected from a single bond, a substituted or unsubstituted C6 to C30 arylene group;

[0140] Said Ar1 to Ar6 are as described in the present invention;

[0141] Each occurrence of R1 is identical or different and is selected from one of hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, cyclopentanyl, cyclohexanyl, adamantyl, and norbornyl; preferably, each occurrence of R1 is identical or different and is selected from one of hydrogen atom, methyl, ethyl, isopropyl, tert-butyl, cyclopentanyl, and cyclohexanyl;

[0142] The condition is that at least one of the Ar1 to Ar6 is selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring.

[0143] Preferably, the compounds of the present invention do not contain deuterium atoms.

[0144] Preferably, the aromatic amine compound is selected from one of the following structures:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] The above lists only some specific structural forms of the aromatic amine compounds represented by formula (I), but the present invention is not limited to these chemical structures listed. All chemical structures based on formula (I) and with substituents as defined above should be included.

[0166] The aromatic amine compound represented by formula (I) of the present invention can be prepared by any one of the following synthetic routes:

[0167] Synthesis route 1:

[0168]

[0169] Synthesis route 2:

[0170]

[0171] You can also combine the first and second synthetic routes to obtain the following synthetic route:

[0172] Synthesis route three:

[0173]

[0174] Synthesis Route 4:

[0175]

[0176] Wherein, the L1-L9, a1, R1, Ar1-Ar6 are as described in the present invention; the 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 a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing 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 a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing 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, Y2 is selected from When L3 is selected from a single bond, Y3 is selected from hydrogen; when L3 is selected from a substituted or unsubstituted C6-C30 arylene group, a divalent group formed by condensing 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, Y3 is selected from

[0177] In synthetic route 1, compound (A) can be reacted with aromatic amine compounds (B), (C), and (D) through one or more Buchwald–Hartwig reactions or Suzuki coupling reactions to obtain the compound represented by formula (I).

[0178] In the second synthetic route, compound (E) can react with compounds (F), (G), and (H) through one or more Buchwald–Hartwig reactions to obtain the compound represented by formula (I).

[0179] In synthetic route three, compound (J) can react with compounds (F) and (G) through a one-step or two-step Buchwald–Hartwig reaction to obtain intermediate (K); then, intermediate (K) reacts with compound (D) through a Buchwald–Hartwig reaction or a Suzuki coupling reaction to obtain the compound represented by formula (I).

[0180] In synthetic route 4, compound (L) and compound (B) undergo a Buchwald–Hartwig reaction or a Suzuki coupling reaction to obtain an intermediate (M); then, the intermediate (M) reacts with compounds (G) and (H) through a one-step or two-step Buchwald–Hartwig reaction to obtain the compound represented by formula (I).

[0181] Each of the above reaction routes adopts the reaction type commonly used in organic synthesis. The reaction conditions (for example, the selection of types such as reaction solvent, catalyst, ligand, base, the amount used, and the order and method of addition) are not particularly limited and can be obtained by conventional methods and operations. The above preparation method has readily available raw materials, a simple preparation process, and excellent yield. The first compound shown in formula (I) provided by the present invention can also be synthesized using conventional reaction types in other organic syntheses without particular limitation. The above is only an example of a synthetic route.

[0182] 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 comprises a hole transport region, a light-emitting layer, and an electron transport region, and the organic layer contains the aromatic amine compound of the present invention.

[0183] Preferably, the organic electroluminescent device further comprises a covering layer, and the covering layer is located on the side of the cathode facing away from the anode or on the side of the anode facing away from the cathode.

[0184] The hole transport region includes one or more of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.

[0185] The hole injection layer of the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, radialene 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-hexaazatriphenylene (HATCN), copper phthalocyanine (CuPC), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonic acid) (PEDOT / PSS), compounds HT-1 to HT -15, Compound p-1, Compound p-2, Compound p-3, and the aromatic amine compound described herein, but not limited thereto. Preferably, the hole injection layer is a single-layer structure composed of a host material and a dopant material. The host material can be a triarylamine compound, such as Compounds HT-1 to HT-19, or the aromatic amine compound described herein. The dopant material can be a radialene compound, preferably Compound p-1, Compound p-2, or Compound p-3. More preferably, the mass ratio of the host material to the dopant material is 100:1 to 100:50. Even more preferably, the mass ratio of the host material to the dopant material is 100:1 to 100:10.

[0186]

[0187]

[0188] The hole transport layer of the present invention can be a single layer structure composed of a single substance, or a single layer structure or a multilayer structure composed of different substances. Triarylamine compounds can be used, or other materials with hole mobility in the range of 10 -6 cm 2 / Vs or above, examples 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 of the present invention, but are not limited thereto. Preferably, the hole transport layer contains the aromatic amine compound of the present invention.

[0189] The light-emitting auxiliary layer of the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Triarylamine compounds, spirofluorene derivatives, dibenzofuran derivatives, and other substances with appropriate 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, N-([1,1'-diphenyl]-4-yl) -N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluoren-2-amine, N,N-di([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 of the present invention, but not limited thereto. Preferably, the light-emitting auxiliary layer contains the aromatic amine compound of the present invention.

[0190] The light-emitting layer of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, and may use two host materials to form a dual host material. The guest material may be a fluorescent compound, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolinazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazole vinyl)-1,1'-biphenyl (BCzVBi), 4, 4'-bis[4-(di-p-tolylamino)phenylvinyl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)picolinoyliridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), di(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), etc. The host material preferably uses a substance with a higher LUMO than the guest material and a lower HOMO than the guest material, such as a metal complex such as an aluminum complex or a zinc complex, a heterocyclic compound such as an oxadiazole derivative or a benzimidazole derivative, a condensed aromatic compound such as a carbazole derivative or an anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, and examples thereof include 8-hydroxyquinoline aluminum (Alq3), 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'-di(9-carbazole)biphenyl (CBP), 4,4',4"-tris(carbazole-9-yl)triphenylamine (TCTA), 9,10-di(2-naphthyl)anthracene (ADN), compounds HT-1 to HT-19, and the aromatic amine compounds described in the present invention, but not limited thereto.

[0191] The electron transport region of the present invention includes one or more of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0192] The electron injection layer of the present invention may be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. One or more of the following substances may be selected: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include, but are not limited to, Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, and the like.

[0193] The electron transport layer described in the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. Aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, triazine derivatives, phenanthroline derivatives, polymer compounds, etc. with high electron transport properties can be used. Examples include Alq3, bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, 2-(4-biphenyl)-5-phenyloxadiazole (PBD), etc., but are not limited thereto.

[0194] The hole blocking layer of the present invention can be a single layer structure composed of a single material, or a single layer structure or a multilayer structure composed of different materials. The selected material requires a T1 energy level higher than the light-emitting layer, so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material must be lower than the HOMO energy level of the main material of the light-emitting layer, so as to play a role in blocking holes. Furthermore, the electron mobility of the hole blocking layer material used is 10 -6 cm 2 / Vs or more, which is beneficial to the transmission of electrons. Preferred are triazine derivatives, azabenzene derivatives, and the like.

[0195] The anode of the present 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, or a transparent or translucent layer structure formed from a high work function material, such as a layer 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), or a reflective film formed from the above metals and the above high work function materials. The specific method depends on the type of device to be prepared. If the device to be prepared is a bottom-emitting device (emitting light on the anode side), a transparent or translucent anode is required. If the device to be prepared is a top-emitting device (emitting light on the cathode side), a reflective anode is required.

[0196] The cathode described in the present invention can be a thin film with a low work function made of lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, or a magnesium-silver alloy. The thickness of the film can be adjusted to create a reflective, transparent, or semi-transparent electrode. The specific configuration depends on the type of device being manufactured. For bottom-emitting devices, a reflective cathode is required, while for top-emitting devices, a transparent or semi-transparent cathode is required.

[0197] The covering layer of the present 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 covering layer material can be organic or inorganic, for example, it can be a metal halide, oxide, nitride, nitrogen oxide, sulfide, selenide, aromatic hydrocarbon compound, heteroaromatic hydrocarbon compound, aromatic amine compound, etc. Examples include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, Alq3, compound CP-1, compound CP-2, compound CP-3, compound CP-4, and the aromatic amine compound of the present invention, but are not limited thereto. Preferably,

[0198]

[0199] Preferably, the hole transport region contains the aromatic amine compound described in the present invention.

[0200] 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 the present invention; further preferably, the hole transport layer contains one or more of the aromatic amine compounds described in the present invention.

[0201] Preferably, the hole transport region includes a hole injection layer, a hole transport layer and a luminescence auxiliary layer, and one of the hole injection layer, hole transport layer and luminescence auxiliary layer contains one or more of the aromatic amine compounds described in the present invention; further preferably, the luminescence auxiliary layer contains the aromatic amine compound described in the present invention.

[0202] Preferably, the light-emitting layer contains the aromatic amine compound described in the present invention.

[0203] Preferably, the light-emitting layer contains a guest material and a host material, and the host material contains the aromatic amine compound described in the present invention.

[0204] 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 covering layer, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the covering layer is located on the side of the cathode facing away from the anode or on the side of the anode facing away from the cathode, and the covering layer contains the aromatic amine compound described in the present invention.

[0205] Preferably, the structure of the organic layer is selected from one of the following:

[0206] i-1) hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer;

[0207] i-2) hole injection layer / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer;

[0208] i-3) hole injection layer / hole transport layer / luminescence auxiliary layer / luminescent layer / electron transport layer / electron injection layer;

[0209] i-4) hole injection layer / hole transport layer / luminescence auxiliary layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer.

[0210] Preferably, the device structure of the organic electroluminescent device of the present invention is selected from one of the following device structures:

[0211] ii-1) anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode / covering layer;

[0212] ii-2) anode / hole injection layer / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capping layer;

[0213] ii-3) anode / hole injection layer / hole transport layer / luminescence auxiliary layer / luminescent layer / electron transport layer / electron injection layer / cathode / covering layer;

[0214] ii-4) anode / hole injection layer / hole transport layer / luminescence auxiliary layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer / cathode / covering layer;

[0215] ii-5) capping layer / anode / hole injection layer / hole transport layer / luminescent layer / electron transport layer / electron injection layer / cathode;

[0216] ii-6) capping layer / anode / hole injection layer / hole transport layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer / cathode;

[0217] ii-7) Covering layer / anode / hole injection layer / hole transport layer / luminescence auxiliary layer / luminescent layer / electron transport layer / electron injection layer / cathode;

[0218] ii-8) Covering layer / anode / hole injection layer / hole transport layer / luminescence-assisting layer / luminescent layer / hole blocking layer / electron transport layer / electron injection layer / cathode.

[0219] The organic layers, cathode, anode, and cover layer can be formed using any of the following methods: vacuum deposition, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, dipping, or screen printing. The thickness of each layer is not particularly limited, provided that good device performance is achieved. Preferably, the organic layers are formed using vacuum deposition, inkjet printing, or spin coating.

[0220] The thickness of each organic layer and the cover layer is usually 5 nm to 100 μm, preferably 10 nm to 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0221] The organic electroluminescent device provided by the present invention can be applied to fields such as lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, VR and car taillights.

[0222] The technical solutions and technical effects of the present invention are further described below with reference to embodiments and comparative examples.

[0223] The mass spectra of the compounds of the present invention were determined using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters, UK, using chloroform as the solvent.

[0224] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0225] Synthesis Example 1: Synthesis of Compound 14

[0226]

[0227] Preparation of intermediate db-14:

[0228] Under nitrogen, a'-14 (8.38 g, 90.00 mmol), b'-14 (24.59 g, 90.00 mmol), and sodium tert-butoxide (15.86 g, 165.00 mmol) were added to 240 ml of toluene. Pd(dppf)Cl2 (0.70 g, 0.95 mmol) was added with stirring, and the mixture was heated under reflux for 7 h. After completion of the reaction, the mixture was cooled to room temperature, added with distilled water, and extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from ethyl acetate to obtain intermediate db-14 (21.06 g, 82%). The purity of the solid was ≥99.67% as determined by HPLC. Mass spectrum: m / z: 285.1529 (theoretical value: 285.1517).

[0229] Preparation of intermediate dc-14:

[0230] Under nitrogen, intermediate da-14 (19.80 g, 70.00 mmol), db-14 (19.98 g, 70.00 mmol), and sodium tert-butoxide (12.49 g, 130.00 mmol) were added to 210 ml of toluene. Pd(dppf)Cl2 (0.59 g, 0.80 mmol) was added with stirring, and the mixture was heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. The mixture was allowed to stand for separation, and the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 9:1) to obtain intermediate dc-14 (25.28 g, 78%). The solid purity was ≥99.63% as determined by HPLC. Mass spectrum: m / z: 439.0921 (theoretical value: 439.0936).

[0231] Preparation of intermediate dd-14:

[0232] Under nitrogen, dc-14 (24.22 g, 55.00 mmol), pinacol diboronate (15.36 g, 60.00 mmol), and KOAc (10.80 g, 110.00 mmol) were added to 250 mL of 1,4-dioxane. Pd(dppf)Cl2 (0.80 g, 1.10 mmol) was added with stirring, and the mixture was heated under reflux for 7 h. After completion of the reaction, the reaction solution was cooled to room temperature, added with distilled water, and extracted with ethyl acetate. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was cooled and crystallized, filtered, and the resulting solid was recrystallized from toluene to obtain intermediate dd-14 (18.23 g, 68%). The purity of the solid was ≥99.71% as determined by HPLC. Mass spectrum: m / z 487.2672 (theoretical value: 487.2683).

[0233] Preparation of intermediate cc-14:

[0234] Under nitrogen, aa-14 (9.46 g, 35.00 mmol), bb-14 (15.35 g, 70.00 mmol), and sodium tert-butoxide (11.53 g, 120.00 mmol) were added to 200 ml of toluene. Pd(dppf)Cl2 (0.48 g, 0.65 mmol) was added with stirring, and the mixture was heated under reflux for 4 h. After completion of the reaction, the reaction solution was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from toluene / methanol (10:3) to obtain intermediate cc-14 (15.32 g, 80%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrum: m / z: 546.1874 (theoretical value: 546.1863).

[0235] Preparation of compound 14:

[0236] Under nitrogen, cc-14 (13.68 g, 25.00 mmol), dd-14 (12.19 g, 25.00 mmol), potassium carbonate (6.22 g, 45.00 mmol), and Pd2(dba)3 (0.27 g, 0.30 mmol) were added to a reaction flask. 200 mL of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction system was heated under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The crystals were cooled and filtered. The resulting solid was recrystallized from toluene to obtain compound 14 (13.08 g, 60%). The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 871.3912 (theoretical value: 871.3926). Theoretical element content (%): C 65 H 49 N3: C, 89.52; H, 5.66; N, 4.82. Measured element content (%): C, 89.56; H, 5.61; N, 4.87.

[0237] Synthesis Example 2: Synthesis of Compound 28

[0238]

[0239] According to the preparation method of Synthesis Example 1, da-14 was replaced with an equal molar amount of da-28, db-14 was replaced with an equal molar amount of db-28, dc-14 was replaced with an equal molar amount of dc-28, bb-14 was replaced with an equal molar amount of bb-28, cc-14 was replaced with an equal molar amount of cc-28, and dd-14 was replaced with an equal molar amount of dd-28 to obtain compound 28 (13.99 g, yield 63%). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 887.4228 (theoretical value: 887.4239). Theoretical element content (%) C 66 H 53 N3: C, 89.25; H, 6.02; N, 4.73. Measured element content (%): C, 89.29; H, 6.06; N, 4.77.

[0240] Synthesis Example 3: Synthesis of Compound 31

[0241]

[0242] Following the preparation method of Synthesis Example 1, bb-14 was replaced with an equal molar amount of db-31, cc-14 was replaced with an equal molar amount of cc-31, and dd-14 was replaced with an equal molar amount of dd-31 to obtain compound 31 (14.43 g, 65% yield). HPLC analysis of the solid showed a purity of ≥99.95%. Mass spectrum m / z: 887.4253 (theoretical value: 887.4239). Theoretical element content (%): C 66 H 53 N3: C, 89.25; H, 6.02; N, 4.73. Measured element content (%): C, 89.20; H, 5.98; N, 4.69.

[0243] Synthesis Example 4: Synthesis of Compound 43

[0244]

[0245] According to the preparation method of Synthesis Example 1, db-14 was replaced with an equal molar amount of db-43, dc-14 was replaced with an equal molar amount of dc-43, bb-14 was replaced with an equal molar amount of bb-43, cc-14 was replaced with an equal molar amount of cc-43, and dd-14 was replaced with an equal molar amount of dd-43 to obtain compound 43 (14.91 g, 70% yield). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 851.4228 (theoretical value: 851.4239). Theoretical element content (%): C 63 H 53 N3: C, 88.80; H, 6.27; N, 4.93. Measured element content (%): C, 88.84; H, 6.31; N, 4.88.

[0246] Synthesis Example 5: Synthesis of Compound 46

[0247]

[0248] Following the same preparation method as in Synthesis Example 1, compound 46 (13.39 g, 69% yield) was obtained by replacing db-14 with an equal molar amount of bb-43, dc-14 with an equal molar amount of dc-46, cc-14 with an equal molar amount of cc-43, and dd-14 with an equal molar amount of dd-46. Theoretical element content (%) was C. 57 H 49 N3: C, 88.22; H, 6.36; N, 5.41. Measured element content (%): C, 88.19; H, 6.40; N, 5.45.

[0249] Synthesis Example 6: Synthesis of Compound 68

[0250]

[0251] Compound 68 (14.16 g, 66% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-68, b'-14 was replaced with an equal molar amount of b'-68, da-14 was replaced with an equal molar amount of da-68, db-14 was replaced with an equal molar amount of db-68, dc-14 was replaced with an equal molar amount of dc-68, bb-14 was replaced with an equal molar amount of db-28, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-68. The purity of the solid was ≥99.93% as determined by HPLC. Theoretical element content (%) was C. 63 H 49 N3: C, 88.17; H, 6.93; N, 4.90. Measured element content (%): C, 88.12; H, 6.96; N, 4.95.

[0252] Synthesis Example 7: Synthesis of Compound 70

[0253]

[0254] Following the same preparation method as in Synthesis Example 1, compound 70 (13.77 g, 67% yield) was obtained by replacing da-14 with an equal molar amount of da-70, db-14 with an equal molar amount of bb-28, dc-14 with an equal molar amount of dc-70, cc-14 with an equal molar amount of cc-68, and dd-14 with an equal molar amount of dd-70. Theoretical element content (%) was C. 61 H 47 N3: C, 89.13; H, 5.76; N, 5.11. Measured element content (%): C, 89.16; H, 5.71; N, 5.15.

[0255] Synthesis Example 8: Synthesis of Compound 78

[0256]

[0257] Compound 78 (14.00 g, 65% yield) was obtained by following the same preparation method as in Synthesis Example 1, replacing da-14 with an equal molar amount of da-68, db-14 with an equal molar amount of db-78, dc-14 with an equal molar amount of dc-78, cc-14 with an equal molar amount of cc-43, and dd-14 with an equal molar amount of dd-78. HPLC analysis revealed a solid purity of ≥99.92%. Mass spectrum: m / z: 861.4094 (theoretical value: 861.4083). Theoretical element content (%): C 64 H 51 N3: C, 89.16; H, 5.96; N, 4.87. Measured element content (%): C, 89.11; H, 5.92; N, 4.92.

[0258] Synthesis Example 9: Synthesis of Compound 86

[0259]

[0260] Compound 86 (15.29 g, 69% yield) was obtained by the same preparation method as in Synthesis Example 1, except that da-14 was replaced with an equal molar amount of da-86, db-14 was replaced with an equal molar amount of db-86, dc-14 was replaced with an equal molar amount of dc-86, bb-14 was replaced with an equal molar amount of bb-86, cc-14 was replaced with an equal molar amount of cc-86, and dd-14 was replaced with an equal molar amount of dd-86. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 885.4073 (theoretical value: 885.4083). Theoretical element content (%): C 66 H 51 N3: C, 89.46; H, 5.80; N, 4.74. Measured element content (%): C, 89.42; H, 5.85; N, 4.70.

[0261] Synthesis Example 10: Synthesis of Compound 99

[0262]

[0263] Compound 99 (12.95 g, 63% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-28, b'-14 was replaced with an equal molar amount of b'-99, da-14 was replaced with an equal molar amount of da-99, db-14 was replaced with an equal molar amount of db-99, dc-14 was replaced with an equal molar amount of dc-99, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-99. The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 821.3783 (theoretical value: 821.3770). Theoretical element content (%): C61 H 47 N3: C, 89.13; H, 5.76; N, 5.11. Measured element content (%): C, 89.17; H, 5.71; N, 5.16.

[0264] Synthesis Example 11: Synthesis of Compound 104

[0265]

[0266] Compound 104 (15.45 g, 67% yield) was obtained by the same preparation method as in Synthesis Example 1, except that da-14 was replaced with an equal molar amount of da-104, db-14 was replaced with an equal molar amount of bb-43, dc-14 was replaced with an equal molar amount of dc-104, bb-14 was replaced with an equal molar amount of bb-104, cc-14 was replaced with an equal molar amount of cc-104, and dd-14 was replaced with an equal molar amount of dd-104. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 921.4096 (theoretical value: 921.4083). Theoretical element content (%): C 69 H 51 N3: C, 89.87; H, 5.57; N, 4.56. Measured element content (%): C, 89.83; H, 5.61; N, 4.52.

[0267] Synthesis Example 12: Synthesis of Compound 114

[0268]

[0269] Following the same preparation method as in Synthesis Example 1, bb-14 was replaced with an equal molar amount of db-78, cc-14 was replaced with an equal molar amount of cc-114, and dd-14 was replaced with an equal molar amount of dd-46 to obtain compound 114 (12.72 g, 60% yield). HPLC analysis revealed a solid purity of ≥99.94%. Mass spectrum: m / z: 847.3938 (theoretical value: 847.3926). Theoretical element content (%): C 63 H 49 N3: C, 89.22; H, 5.82; N, 4.95. Measured element content (%): C, 89.26; H, 5.87; N, 4.91.

[0270] Synthesis Example 13: Synthesis of Compound 117

[0271]

[0272] Following the same preparation method as in Synthesis Example 1, compound 117 (15.01 g, 69% yield) was obtained by replacing db-14 with an equal molar amount of db-117, dc-14 with an equal molar amount of dc-117, cc-14 with an equal molar amount of cc-43, and dd-14 with an equal molar amount of dd-117. Theoretical element content (%) was C. 64 H 59 N3: C, 88.34; H, 6.83; N, 4.83. Measured element content (%): C, 88.37; H, 6.87; N, 4.88.

[0273] Synthesis Example 14: Synthesis of Compound 125

[0274]

[0275] Compound 125 (13.81 g, 59% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-28, b'-14 was replaced with an equal molar amount of b'-125, db-14 was replaced with an equal molar amount of db-125, dc-14 was replaced with an equal molar amount of dc-125, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-125. The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum: m / z: 935.4253 (theoretical value: 935.4239). Theoretical element content (%): C 70 H 53 N3: C, 89.81; H, 5.71; N, 4.49. Measured element content (%): C, 89.85; H, 5.66; N, 4.45.

[0276] Synthesis Example 15: Synthesis of Compound 132

[0277]

[0278] Compound 132 (14.14 g, 62% yield) was obtained by the same preparation method as in Synthesis Example 1, except that db-14 was replaced with an equal molar amount of db-132, dc-14 was replaced with an equal molar amount of dc-132, bb-14 was replaced with an equal molar amount of bb-132, cc-14 was replaced with an equal molar amount of cc-132, and dd-14 was replaced with an equal molar amount of dd-132. The purity of the solid was ≥99.94% as determined by HPLC. Mass spectrum: m / z: 911.4227 (theoretical value: 911.4239). Theoretical element content (%): C 68 H 53N3: C, 89.54; H, 5.86; N, 4.61. Measured element content (%): C, 89.59; H, 5.82; N, 4.66.

[0279] Synthesis Example 16: Synthesis of Compound 170

[0280]

[0281] Compound 170 (14.60 g, 64% yield) was obtained by the same preparation method as in Synthesis Example 1, except that da-14 was replaced with an equal molar amount of da-68, db-14 was replaced with an equal molar amount of db-170, dc-14 was replaced with an equal molar amount of dc-170, bb-14 was replaced with an equal molar amount of db-78, cc-14 was replaced with an equal molar amount of cc-170, and dd-14 was replaced with an equal molar amount of dd-170. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 911.4252 (theoretical value: 911.4239). Theoretical element content (%): C 68 H 53 N3: C, 89.54; H, 5.86; N, 4.61. Measured element content (%): C, 89.51; H, 5.90; N, 4.67.

[0282] Synthesis Example 17: Synthesis of Compound 206

[0283]

[0284] Preparation of intermediate ff-206:

[0285] Following the same preparation method as for intermediate dd-14 in Synthesis Example 1, except that db-14 was replaced with an equal molar amount of bb-86, and dc-14 was replaced with an equal molar amount of dc-206, intermediate ff-206 (14.48 g, 64% yield) was obtained. HPLC analysis of the solid revealed a purity of ≥99.71%. Mass spectrum: m / z: 411.2359 (theoretical value: 411.2370).

[0286] Preparation of intermediate cc-206:

[0287] Under nitrogen, aa-206 (11.11 g, 35.00 mmol), db-78 (8.59 g, 35.00 mmol), and sodium tert-butoxide (6.73 g, 70.00 mmol) were added to 105 ml of toluene. Pd(dppf)Cl2 (0.29 g, 0.40 mmol) was added with stirring, and the mixture was heated under reflux for 3 h. After completion of the reaction, the reaction solution was cooled to room temperature, added with distilled water, and extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was cooled and crystallized, and then filtered with suction. The resulting solid was recrystallized from toluene / methanol (10:3) to obtain intermediate cc-206 (11.72 g, 77%). The purity of the solid was ≥99.74% as determined by HPLC. Mass spectrum: m / z: 433.0244 (theoretical value: 433.0233).

[0288] Preparation of intermediate ee-206:

[0289] Under nitrogen, intermediate cc-206 (10.87 g, 25.00 mmol), dd-206 (6.48 g, 25.00 mmol), and sodium tert-butoxide (3.84 g, 40.00 mmol) were added to 100 mL of toluene. Pd2(dba)3 (0.27 g, 0.30 mmol) and P(t-Bu)3 (1.20 mL of a 0.5 M solution in toluene, 0.60 mmol) were added with stirring. The mixture was heated under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. The mixture was allowed to stand for separation. The organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The filtrate was purified by silica gel column chromatography using petroleum ether / ethyl acetate (volume ratio 10:1) to obtain intermediate ee-206 (12.57 g, 82%). The solid purity was ≥99.81% as determined by HPLC. Mass spectrum m / z: 612.1952 (theoretical value: 612.1968).

[0290] Preparation of compound 206:

[0291] Under nitrogen, ee-206 (12.26 g, 20.00 mmol), ff-206 (8.23 g, 20.00 mmol), potassium carbonate (4.98 g, 36.00 mmol), and Pd2(dba)3 (0.23 g, 0.25 mmol) were added to a reaction flask. 200 mL of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction mixture was heated under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The mixture was cooled and crystallized, filtered, and the resulting solid was recrystallized from toluene to obtain compound 206 (10.17 g, 59%). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum: m / z: 861.3732 (theoretical value: 861.3719). Theoretical element content (%): C 63 H 47 N3O: C, 87.77; H, 5.50; N, 4.87. Measured element content (%): C, 87.73; H, 5.56; N, 4.82.

[0292] Synthesis Example 18: Synthesis of Compound 214

[0293]

[0294] Compound 214 (13.15 g, 61% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-214, b'-14 was replaced with an equal molar amount of b'-31, db-14 was replaced with an equal molar amount of db-214, dc-14 was replaced with an equal molar amount of dc-214, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-214. The purity of the solid was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 861.3731 (theoretical value: 861.3719). Theoretical element content (%): C 63 H 47 N3O: C, 87.77; H, 5.50; N, 4.87. Measured element content (%): C, 87.72; H, 5.55; N, 4.83.

[0295] Synthesis Example 19: Synthesis of Compound 223

[0296]

[0297] Compound 223 (13.77 g, 60% yield) was obtained by the same preparation method as in Synthesis Example 1, except that b'-14 was replaced with an equal molar amount of b'-223, db-14 was replaced with an equal molar amount of db-223, dc-14 was replaced with an equal molar amount of dc-223, cc-14 was replaced with an equal molar amount of cc-86, and dd-14 was replaced with an equal molar amount of dd-223. The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 917.3816 (theoretical value: 917.3804). Theoretical element content (%): C 66 H 51 N3S: C, 86.33; H, 5.60; N, 4.58. Measured element content (%): C, 86.38; H, 5.64; N, 4.54.

[0298] Synthesis Example 20: Synthesis of Compound 224

[0299]

[0300] Compound 224 (13.45 g, 59% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-224, b'-14 was replaced with an equal molar amount of b'-214, da-14 was replaced with an equal molar amount of da-68, db-14 was replaced with an equal molar amount of db-224, dc-14 was replaced with an equal molar amount of dc-224, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-224. The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrum: m / z: 911.3889 (theoretical value: 911.3876). Theoretical element content (%): C 67 H 49 N3O: C, 88.22; H, 5.41; N, 4.61. Measured element content (%): C, 88.26; H, 5.45; N, 4.56.

[0301] Synthesis Example 21: Synthesis of Compound 236

[0302]

[0303] Following the same preparation method as in Synthesis Example 1, bb-14 was replaced with an equal molar amount of db-206, cc-14 was replaced with an equal molar amount of db-236, and dd-14 was replaced with an equal molar amount of dd-46 to obtain compound 236 (12.70 g, 58% yield). HPLC analysis revealed a solid purity of ≥99.93%. Mass spectrum: m / z: 875.3526 (theoretical value: 875.3512). Theoretical element content (%): C 63 H 45N3O2: C, 86.37; H, 5.18; N, 4.80. Measured element content (%): C, 86.41; H, 5.13; N, 4.85.

[0304] Synthesis Example 22: Synthesis of Compound 251

[0305]

[0306] Compound 251 (11.42 g, 65% yield) was obtained by following the same preparation method as in Example 17, replacing bb-86 with an equal molar amount of bb-132, dc-206 with an equal molar amount of dc-251, db-78 with an equal molar amount of bb-86, cc-206 with an equal molar amount of cc-251, dd-206 with an equal molar amount of dd-251, ee-206 with an equal molar amount of ee-251, and ff-206 with an equal molar amount of ff-251. HPLC analysis revealed a solid purity of ≥99.95%. Mass spectrum: m / z: 877.3480 (theoretical value: 877.3491). Theoretical element content (%): C 63 H 47 N3S: C, 86.17; H, 5.39; N, 4.79. Measured element content (%): C, 86.12; H, 5.43; N, 4.74.

[0307] Synthesis Example 23: Synthesis of Compound 265

[0308]

[0309] Compound 265 (14.22 g, 60% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-28, b'-14 was replaced with an equal molar amount of b'-265, bb-14 was replaced with an equal molar amount of db-265, cc-14 was replaced with an equal molar amount of cc-265, and dd-14 was replaced with an equal molar amount of dd-31. The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum: m / z: 947.3378 (theoretical value: 947.3368). Theoretical element content (%): C 66 H 49 N3S2: C, 83.60; H, 5.21; N, 4.43. Measured element content (%): C, 83.64; H, 5.25; N, 4.39.

[0310] Synthesis Example 24: Synthesis of Compound 293

[0311]

[0312] Compound 293 (13.59 g, 63% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-68, b'-14 was replaced with an equal molar amount of b'-293, da-14 was replaced with an equal molar amount of da-68, db-14 was replaced with an equal molar amount of db-293, dc-14 was replaced with an equal molar amount of dc-293, cc-14 was replaced with an equal molar amount of cc-68, and dd-14 was replaced with an equal molar amount of dd-293. The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum: m / z: 910.4047 (theoretical value: 910.4035). Theoretical element content (%): C 67 H 50 N4: C, 88.32; H, 5.53; N, 6.15. Measured element content (%): C, 88.37; H, 5.49; N, 6.11.

[0313] Synthesis Example 25: Synthesis of Compound 315

[0314]

[0315] According to the preparation method of Synthesis Example 17, bb-86 was replaced with an equal molar amount of db-315, dc-206 was replaced with an equal molar amount of dc-315, aa-206 was replaced with an equal molar amount of aa-315, cc-206 was replaced with an equal molar amount of cc-315, dd-206 was replaced with an equal molar amount of dd-315, ee-206 was replaced with an equal molar amount of ee-315, and ff-206 was replaced with an equal molar amount of ff-315 to obtain compound 315 (12.19 g, 64% yield). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 951.4176 (theoretical value: 951.4189). Theoretical element content (%): C 70 H 53 N3O: C, 88.30; H, 5.61; N, 4.41. Measured element content (%): C, 88.35; H, 5.57; N, 4.46.

[0316] Synthesis Example 26: Synthesis of Compound 386

[0317]

[0318] According to the preparation method of Synthesis Example 17, da-14 was replaced with an equal molar amount of da-70, bb-86 was replaced with an equal molar amount of db-386, dc-206 was replaced with an equal molar amount of dc-386, aa-206 was replaced with an equal molar amount of aa-386, db-78 was replaced with an equal molar amount of db-28, cc-206 was replaced with an equal molar amount of cc-386, dd-206 was replaced with an equal molar amount of bb-104, ee-206 was replaced with an equal molar amount of ee-386, and ff-206 was replaced with an equal molar amount of ff-386 to obtain compound 386 (11.69 g, yield 67%). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 871.3937 (theoretical value: 871.3926). Theoretical element content (%): C 65 H 49 N3: C, 89.52; H, 5.66; N, 4.82. Measured element content (%): C, 89.57; H, 5.62; N, 4.86.

[0319] Synthesis Example 27: Synthesis of Compound 393

[0320]

[0321] According to the preparation method of Synthesis Example 17, bb-86 was replaced with an equal molar amount of bb-14, dc-206 was replaced with an equal molar amount of dc-393, db-78 was replaced with an equal molar amount of bb-43, cc-206 was replaced with an equal molar amount of cc-393, dd-206 was replaced with an equal molar amount of dd-393, ee-206 was replaced with an equal molar amount of ee-393, and ff-206 was replaced with an equal molar amount of ff-393 to obtain compound 393 (11.34 g, 65% yield). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 871.3914 (theoretical value: 871.3926). Theoretical element content (%): C 65 H 49 N3: C, 89.52; H, 5.66; N, 4.82. Measured element content (%): C, 89.48; H, 5.71; N, 4.77.

[0322] Synthesis Example 28: Synthesis of Compound 414

[0323]

[0324] Compound 414 (10.20 g, 61% yield) was obtained by following the same preparation method as in Example 17, replacing db-78 with an equal molar amount of db-28, cc-206 with an equal molar amount of cc-414, dd-206 with an equal molar amount of dd-414, ee-206 with an equal molar amount of ee-414, and ff-206 with an equal molar amount of ff-315. HPLC analysis revealed a solid purity of ≥99.92%. Mass spectrum: m / z: 835.3940 (theoretical value: 835.3926). Theoretical element content (%): C 62 H 49 N3: C, 89.07; H, 5.91; N, 5.03. Measured element content (%): C, 89.11; H, 5.87; N, 5.08.

[0325] Synthesis Example 29: Synthesis of Compound 461

[0326]

[0327] Preparation of intermediate cc-461:

[0328] Following the same preparation method as that used for intermediate CC-206 in Synthesis Example 17, aa-206 was replaced with an equal molar amount of aa-461, and db-78 was replaced with an equal molar amount of bb-86 to obtain intermediate CC-461 (10.17 g, 82%). HPLC analysis of the solid revealed a purity of ≥99.79%. Mass spectrum: m / z: 353.0756 (theoretical value: 353.0738).

[0329] Preparation of compound 461:

[0330] Under nitrogen, cc-461 (8.86 g, 25.00 mmol), dd-31 (18.56 g, 50.00 mmol), potassium carbonate (12.44 g, 90.00 mmol), and Pd2(dba)3 (0.46 g, 0.50 mmol) were added to a reaction flask. 250 mL of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction system was heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and concentrated by rotary evaporation. The crystals were cooled and filtered, and the resulting solid was recrystallized from toluene to obtain compound 461 (11.77 g, 61%). The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 771.3627 (theoretical value: 771.3613). Theoretical element content (%): C 57 H 45N3: C, 88.68; H, 5.88; N, 5.44. Measured element content (%): C, 88.63; H, 5.82; N, 5.40.

[0331] Synthesis Example 30: Synthesis of Compound 488

[0332]

[0333] Under nitrogen, aa-488 (7.87 g, 25.00 mmol), dd-46 (30.85 g, 75.00 mmol), potassium carbonate (18.66 g, 135.00 mmol), and Pd2(dba)3 (0.73 g, 0.80 mmol) were added to a reaction flask. 300 mL of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction system was heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The crystals were cooled and filtered. The resulting solid was recrystallized from toluene to obtain compound 488 (13.23 g, 57%). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum: m / z: 927.4541 (theoretical value: 927.4552). Theoretical element content (%): C 69 H 57 N3: C, 89.28; H, 6.19; N, 4.53. Measured element content (%): C, 89.31; H, 6.23; N, 4.57.

[0334] Synthesis Example 31: Synthesis of Compound 513

[0335]

[0336] Preparation of intermediate dd-513:

[0337] Following the same preparation method as that used for intermediate dd-14 in Synthesis Example 1, intermediate dd-513 (17.15 g, 74% yield) was obtained by replacing da-14 with an equal molar amount of da-70, db-14 with an equal molar amount of db-28, and dc-14 with an equal molar amount of dc-513. The solid purity was ≥99.73% as determined by HPLC. Mass spectrum: m / z: 421.2227 (theoretical value: 421.2213).

[0338] Preparation of intermediate ff-513:

[0339] Following the same preparation method as for intermediate dd-14 in Synthesis Example 1, except that db-14 was replaced with an equal molar amount of db-437, and dc-14 was replaced with an equal molar amount of fc-513, intermediate ff-513 (16.14 g, 69% yield) was obtained. HPLC analysis of the solid revealed a purity of ≥99.75%. Mass spectrum: m / z: 425.2516 (theoretical value: 425.2526).

[0340] Preparation of intermediate ee-513:

[0341] Under nitrogen, a reaction flask was charged with cc-206 (15.22 g, 35.00 mmol), dd-513 (14.75 g, 35.00 mmol), potassium carbonate (8.98 g, 65.00 mmol), and Pd2(dba)3 (0.37 g, 0.40 mmol). 250 mL of a 2:1:1 toluene / ethanol / water mixture was added and stirred. The reaction system was heated under reflux for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The mixture was cooled and crystallized, filtered, and the resulting solid was recrystallized from toluene to obtain intermediate ee-513 (14.09 g, 62%). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrum: m / z: 648.2345 (theoretical value: 648.2332).

[0342] Preparation of compound 513:

[0343] Following the same preparation method as compound 206 in Example 17, ee-206 was replaced with an equal molar amount of ee-513, and ff-206 was replaced with an equal molar amount of ff-513 to obtain compound 513 (13.68 g, 60%). HPLC analysis of the solid showed a purity of ≥99.94%. Mass spectrum m / z: 911.4251 (theoretical value: 911.4239). Theoretical element content (%): C 68 H 53 N3: C, 89.54; H, 5.86; N, 4.61. Measured element content (%): C, 89.59; H, 5.81; N, 4.66.

[0344] Synthesis Example 32: Synthesis of Compound 535

[0345]

[0346] Compound 535 (13.36 g, 63% yield) was obtained by the same preparation method as in Synthesis Example 1, except that a'-14 was replaced with an equal molar amount of a'-535, b'-14 was replaced with an equal molar amount of b'-535, db-14 was replaced with an equal molar amount of db-535, dc-14 was replaced with an equal molar amount of dc-535, aa-14 was replaced with an equal molar amount of aa-535, bb-14 was replaced with an equal molar amount of db-28, cc-14 was replaced with an equal molar amount of cc-535, and dd-14 was replaced with an equal molar amount of dd-535. The purity of the solid was ≥99.90% as determined by HPLC. Mass spectrum: m / z: 847.3939 (theoretical value: 847.3926). Theoretical element content (%): C 63 H 49 N3: C, 89.22; H, 5.82; N, 4.95. Measured element content (%): C, 89.26; H, 5.87; N, 4.91.

[0347] The organic materials used in the device preparation examples were purified by sublimation, with a purity of more than 99.99%. The ITO glass substrate and ITO / Ag / ITO glass substrate used in the device preparation examples were purchased from the market.

[0348] The following are other compounds used in the device preparation examples except the aromatic amine compound represented by formula (I) of the present invention:

[0349]

[0350]

[0351] The test software, computer, K2400 digital source meter from Keithley Company, USA and PR788 spectrum scanning luminance meter from Photo Research Company, USA were used to form a combined IVL test system. The device prepared by the present invention was tested at a current density of 15 mA / cm at atmospheric pressure and room temperature. 2 The luminous efficiency and driving voltage at the time of 100 s are shown in Tables 1 to 3. The lifespan of the devices prepared in the present invention (luminance decays to 95% of the initial brightness) was tested using the McScience M6000 OLED lifespan test system at atmospheric pressure and room temperature.

[0352] Comparative device preparation example 1: Comparative device 1

[0353] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0354] The following layers were evaporated layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a, 2-TNATA as a hole injection layer with a thickness of 50 nm; b, HT-1 as a hole transport layer with a thickness of 40 nm; c, CBP and Ir(mppy)3 (mass ratio 95:5) as a light-emitting layer with a thickness of 35 nm; d, TPBi as a hole blocking layer with a thickness of 30 nm; e, NBphen and Liq (mass ratio 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 2:1) as a cathode with a thickness of 10 nm; h: CP-4 as a covering layer with a thickness of 100 nm.

[0355] Comparative device preparation examples 2 to 7: Comparative devices 2 to 7

[0356] Comparative devices 2 to 7 were obtained by replacing HT-1 in the hole transport layer with HT-2 to HT-7, respectively, and following the same other steps as in Comparative Device Preparation Example 1.

[0357] Device Preparation Examples 1-32: Light-Emitting Devices 1-32

[0358] Light-emitting devices 1 to 32 were obtained by replacing HT-1 in the hole transport layer with the aromatic amine compounds of the present invention in Synthesis Examples 1 to 32, and following the same other steps as in Comparative Device Preparation Example 1.

[0359] Table 1

[0360]

[0361]

[0362]

[0363] Comparative device preparation example 8: Comparative device 8

[0364] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0365] The following layers were deposited layer by layer on the above ITO / Ag / ITO glass substrate: a, 2-TNATA as a hole injection layer with a thickness of 60 nm; b, NPB as a hole transport layer with a thickness of 35 nm; c, HT-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 48:48:4) as a light-emitting layer with a thickness of 35 nm; e, BAlq as a hole blocking layer with a thickness of 35 nm; f, NBphen and Liq (mass ratio 5:2) as an electron transport layer with a thickness of 25 nm; g, LiF as an electron injection layer with a thickness of 0.2 nm; h, Mg and Ag (mass ratio 1:1) as a cathode with a thickness of 10 nm; i: CP-4 as a covering layer with a thickness of 110 nm.

[0366] Comparative device preparation examples 9 to 14: Comparative devices 9 to 14

[0367] Comparative devices 9 to 14 were obtained by replacing HT-1 in the light-emitting auxiliary layer with HT-2 to HT-7, respectively, and following the same other steps as in Comparative Device Preparation Example 8.

[0368] Device Preparation Examples 33-64: Light-Emitting Devices 33-64

[0369] Light-emitting devices 33 to 64 were obtained by replacing HT-1 in the light-emitting auxiliary layer with the aromatic amine compounds of the present invention in Synthesis Examples 1 to 32, and following the same other steps as in Comparative Device Preparation Example 8.

[0370] Table 2

[0371]

[0372]

[0373] Comparative device preparation example 15: Comparative device 15

[0374] First, the ITO / Ag / ITO glass substrate was ultrasonically cleaned twice with deionized water for 20 minutes each time, and then ultrasonically cleaned with isopropyl alcohol, acetone and methanol for 20 minutes each, followed by exposure to ultraviolet light and ozone for 30 minutes, and finally placed in a vacuum evaporation equipment for use.

[0375] The following layers were deposited layer by layer on the above-mentioned ITO / Ag / ITO glass substrate: a, HTM and p-1 (mass ratio of 100:7) as hole injection layer with a thickness of 20 nm; b, HTM as hole transport layer with a thickness of 35 nm; c, BH and BD (mass ratio of 97:3) as light-emitting layer with a thickness of 30 nm; d, TPBi as hole blocking layer with a thickness of 20 nm; e, NBphen and Liq (mass ratio of 4:1) as electron transport layer with a thickness of 30 nm; f, LiF as electron injection layer with a thickness of 0.2 nm; g, Mg and Ag (mass ratio of 1:1) as cathode with a thickness of 10 nm; h: CP-1 as covering layer with a thickness of 100 nm.

[0376] Comparative device preparation examples 16 to 18: Comparative devices 16 to 18

[0377] Comparative devices 16 to 18 were obtained by replacing CP-1 in the covering layer with CP-2 to CP-4 respectively and following the same other steps as in Comparative Device Preparation Example 15.

[0378] Device Preparation Examples 65-96: Light-Emitting Devices 65-96

[0379] Light-emitting devices 65 to 96 were obtained by replacing CP-1 in the covering layer with the aromatic amine compounds of the present invention in Synthesis Examples 1 to 32, respectively, and following the same other steps as in Comparative Device Preparation Example 15.

[0380] Table 3

[0381]

[0382]

[0383] According to the test data in Tables 1 to 3, the aromatic amine compounds of the present invention, when used as hole transport materials or covering layer materials, can improve the luminous efficiency of the device and extend the service life of the device. They are a type of OLED material with excellent performance and have good application prospects.

[0384] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. An aromatic amine compound having a structure represented by Formula (IB), Formula (IE) or Formula (IF): in, The L1 to L3 are independently selected from one of the following structures: The L4 to L9 are independently selected from a single bond or one of the following structures: Among them, the a 11 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 11 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said c 11 Each occurrence is identically or differently selected from 0, 1 or 2; The R 11 Each occurrence is the same or different and is selected from a hydrogen atom, an unsubstituted C1-C4 linear or branched alkyl group; Each occurrence of a1 is identical or different and is selected from 0, 1, 2 or 3; Each occurrence of R1 is the same or different and is selected from the group consisting of hydrogen, unsubstituted methyl, unsubstituted ethyl, unsubstituted n-propyl, unsubstituted isopropyl, unsubstituted n-butyl, unsubstituted isobutyl, unsubstituted sec-butyl, and unsubstituted tert-butyl. One, two or three of the Ar1 to Ar6 are selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring, "two of the Ar1 to Ar6" are selected from Ar1 and Ar3, Ar1 and Ar5, or Ar3 and Ar5; "three of the Ar1 to Ar6" are selected from Ar1, Ar3 and Ar5; The "group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring" in Ar1 to Ar6 is selected from one of the following structures: The groups in Ar1 to Ar6 that are not "a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring" are independently selected from one of the following structures: Among them, the a 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 21 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 21 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said e 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 21 Each occurrence is the same or different and is selected from one of hydrogen atom, unsubstituted C1-C4 linear or branched alkyl, unsubstituted C3-C10 cycloalkyl, unsubstituted phenyl, or two adjacent R 21 Connected to form an unsubstituted benzene ring; The R 21a Each occurrence is the same or different and is selected from a hydrogen atom, an unsubstituted C1-C4 linear or branched alkyl group; The R 21b Each occurrence is the same or different and is selected from one of hydrogen atom, unsubstituted C1-C4 linear or branched alkyl group, and unsubstituted phenyl group; The R 22 、R 23 independently selected from one of unsubstituted methyl, unsubstituted ethyl, unsubstituted n-propyl, unsubstituted isopropyl, unsubstituted n-butyl, unsubstituted sec-butyl, unsubstituted isobutyl, unsubstituted tert-butyl, unsubstituted phenyl, and unsubstituted naphthyl; The R 24 One selected from unsubstituted phenyl and unsubstituted naphthyl.

2. The aromatic amine compound according to claim 1, characterized in that The L1 to L3 are independently selected from a single bond or one of the structures shown below, and the L1 to L3 are not selected from a single bond at the same time: The L4 to L9 are independently selected from single bonds; The R 11 Each occurrence is identically selected from hydrogen atoms.

3. The aromatic amine compound according to claim 1, characterized in that Each occurrence of R1 is identically selected from hydrogen atoms.

4. The aromatic amine compound according to claim 1, characterized in that The "group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring" in Ar1 to Ar6 is selected from one of the following structures: The groups in Ar1 to Ar6 that are not "a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring" are independently selected from one of the following structures: The R 21 Each occurrence is identically selected from hydrogen atoms; The R 21a Each occurrence is identically selected from hydrogen atoms; The R 21b Each occurrence is identically selected from hydrogen atoms; The R 22 、R 23 Independently selected from one of unsubstituted methyl and unsubstituted phenyl.

5. The aromatic amine compound according to claim 1, characterized in that The aromatic amine compound has a structure shown in formula (IB): Wherein, the L1 is selected from one of the following structures: The L4 to L9 are independently selected from a single bond or one of the following structures: Among them, the a 11 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said b 11 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said c 11 Each occurrence is identically or differently selected from 0, 1 or 2; The R 11 Each occurrence is the same or different and is selected from a hydrogen atom, an unsubstituted C1-C4 linear or branched alkyl group; One, two or three of the Ar1 to Ar6 are selected from a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring with a substituted or unsubstituted C5 to C7 aliphatic ring, "two of the Ar1 to Ar6" are selected from Ar1 and Ar3, Ar1 and Ar5, or Ar3 and Ar5; "three of the Ar1 to Ar6" are selected from Ar1, Ar3 and Ar5; The "group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C5-C7 aliphatic ring" in Ar1 to Ar6 is selected from one of the following structures: The groups in Ar1 to Ar6 that are not "a group formed by condensing a substituted or unsubstituted C6 to C30 aromatic ring and a substituted or unsubstituted C5 to C7 aliphatic ring" are independently selected from one of the following structures: Among them, the a 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4 or 5; said b 21 Each occurrence is identically or differently selected from 0, 1, 2, 3 or 4; said c 21 Each occurrence is identically or differently selected from 0, 1, 2 or 3; said e 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5 or 6; said f 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said g 21 Each occurrence is identically or differently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; The R 21 Each occurrence is the same or different and is selected from one of hydrogen atom, unsubstituted C1-C4 linear or branched alkyl group, and unsubstituted C3-C10 cycloalkyl group; The R 21a Each occurrence is the same or different and is selected from a hydrogen atom, an unsubstituted C1-C4 linear or branched alkyl group; The R 21b Each occurrence is the same or different and is selected from one of hydrogen atom, unsubstituted C1-C4 linear or branched alkyl group, and unsubstituted phenyl group; The R 22 、R 23 independently selected from one of unsubstituted methyl, unsubstituted ethyl, unsubstituted n-propyl, unsubstituted isopropyl, unsubstituted n-butyl, unsubstituted sec-butyl, unsubstituted isobutyl, unsubstituted tert-butyl, unsubstituted phenyl, and unsubstituted naphthyl; The R 24 One selected from unsubstituted phenyl and unsubstituted naphthyl; When Ar1 is selected from When L4 is selected When Ar2 is selected from When L5 is selected Said a1 and R1 are as described in claim 1.

6. The aromatic amine compound according to claim 1, characterized in that The aromatic amine compound has a structure shown in formula (IE) or (IF): Wherein, L1 to L3 are independently selected from one of the following structures:

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 comprises a hole transport region, a light-emitting layer, and an electron transport region, characterized in that: The organic layer contains the aromatic amine compound according to any one of claims 1 to 7.

9. An organic electroluminescent device comprising an anode, a cathode, an organic layer located between the anode and the cathode, and a covering layer, wherein the organic layer comprises a hole transport region, a light-emitting layer, and an electron transport region, and the covering layer is located on the side of the cathode facing away from the anode or on the side of the anode facing away from the cathode, characterized in that: The covering layer contains the aromatic amine compound according to any one of claims 1 to 7.

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