Arylamine compound and organic electroluminescent device thereof
By using aromatic amine compounds as hole transport layer and cover layer materials, the problem of insufficient luminescence efficiency and service life of organic electroluminescent devices in the prior art is solved, and higher luminescence efficiency and longer service life are achieved.
Patent Information
- Application Number
- CN202510180088.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-02-18
- Publication Date
- 2025-04-15
AI Technical Summary
Existing hole transport materials and cover materials cannot effectively improve the luminous efficiency and service life of organic electroluminescent devices.
An aromatic amine compound is used as the hole transport layer and cover layer material to increase the hole transport rate, block electrons, achieve maximum recombination between carriers, and reduce the energy barrier during hole injection.
It improves the luminescence efficiency of organic electroluminescent devices and extends the service life of the device, while simplifies the preparation method, reduces costs, and has good industrialization prospects.
Smart Images

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Abstract
Description
Technical Field
[0001] The invention relates to the technical field of organic photoelectric materials, and in particular to an aromatic amine compound and an organic electroluminescent device thereof. Background Art
[0002] With the continuous development of the information age, people have higher and higher requirements for information display technology. The response speed of liquid crystal displays is relatively slow and it is difficult to prepare large-area display devices with modern technology. Compared with liquid crystal displays, organic electroluminescent devices (OLED) displays have significant characteristics such as active luminescence, lightness, thinness, good contrast, no viewing angle restrictions, and low energy consumption. They have obvious advantages in the fields of display and lighting and have broad application prospects.
[0003] The structure of OLED devices is usually divided into single-layer devices, double-layer devices, three-layer devices and multi-layer devices. The typical OLED structure is to form HTL (hole transport layer), EML (light-emitting layer), ETL (electron transport layer), cathode, etc. on the anode. The working principle of OLED devices is that the holes and electrons emitted from the anode and cathode are injected into the organic layer of the device; the electrons and holes migrate from the hole transport layer and the electron transport layer to the light-emitting area of the device respectively; the holes injected from the anode and the electrons injected from the cathode recombine in the light-emitting layer of the organic matter to form excitons; the excited state energy is transferred to the organic light-emitting substance; and it is transitioned from the ground state to the excited state. Because the energy of the excited state is unstable, the excited organic molecules will transition from the excited state to the ground state, and the luminescence phenomenon will occur after the radiation transition.
[0004] The basic function of the hole transport layer in the OLED device is to increase the transmission rate of holes in the device and effectively block electrons in the light-emitting layer to achieve maximum recombination between carriers and improve the luminous efficiency. At the same time, it reduces the energy barrier of holes in the injection process and improves the injection efficiency of holes, thereby improving the luminous efficiency of the device and extending the service life of the device. The function of the cover layer in the OLED device is to improve the light extraction efficiency, adjust the interference effect of light, and reduce the amount of light loss, thereby improving the luminous efficiency of the device and extending the service life of the device.
[0005] However, traditional hole transport materials and covering layer materials usually cannot provide satisfactory luminous efficiency and service life; therefore, how to design a type of hole transport material and covering layer material with high brightness, long life and low cost is a problem to be solved. Summary of the invention
[0006] In order to solve the above problems, the present invention aims to provide an aromatic amine compound and an organic electroluminescent device thereof, which can improve the luminous efficiency of the organic electroluminescent device and extend the service life of the device.
[0007] The present invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:
[0008]
[0009] Wherein, Ar1 is selected from the structure represented by formula II:
[0010]
[0011] The v is independently selected from any one of CH and N, and at least one of the v is selected from N;
[0012] The z is independently selected from any one of CH and N;
[0013] The R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0014] The a is selected from 0, 1, 2, 3 or 4; when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;
[0015] The b is selected from 0, 1, 2, 3 or 4; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring;
[0016] The c is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;
[0017] The d is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R4, the two or more R4 are the same or different from each other;
[0018] The Ar2 is selected from any one of the following groups:
[0019]
[0020] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;
[0021] The R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0022] The R x Any one selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring;
[0023] The R y any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring, or R x , R y are connected to form a substituted or unsubstituted ring;
[0024] The e1 is selected from 0, 1, 2, 3 or 4; when there are two or more R e When two or more R e The same or different from each other, or two adjacent R e are connected to each other to form a substituted or unsubstituted ring;
[0025] The L1, L2, and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring group.
[0026] 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 or located on the side of the cathode away from the anode, wherein the organic layer contains at least one of the aromatic amine compounds described in the present invention.
[0027] Beneficial Effects
[0028] The present invention provides an aromatic amine compound, which can improve the hole transmission rate in the device when used in the hole transport layer of an OLED device, and effectively block electrons in the light-emitting layer to achieve maximum recombination between carriers, and at the same time, reduce the energy barrier of holes in the injection process, improve the hole injection efficiency, thereby improving the luminous efficiency of the device and extending the service life of the device; when the compound is used in the covering layer of the device, it can improve the light extraction efficiency, adjust the interference effect of light, and reduce the amount of light loss, thereby improving the luminous efficiency of the device and extending the service life of the device. The preparation method of the compound provided by the present invention is simple, the raw materials are easily available, can meet the needs of industrialization, and has good industrialization prospects. DETAILED DESCRIPTION
[0029] The following will be clearly and completely described in conjunction with the technical solutions of the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. After reading the present invention, modifications of various equivalent forms of the present invention by those skilled in the art all fall within the scope defined by the present invention.
[0030] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine and iodine.
[0031] In the present specification, "-*" means a part connected to another substituent. "-*" can be connected to any optional position of the group / fragment to which it is connected.
[0032] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically, it can be connected to any of the corresponding optional sites of the ring. For example, Can be expressed Can be expressed And so on.
[0033] In the present specification, when the position of a substituent or a bonding site on a ring is not fixed, it means that it can be bonded to any one of any optional sites of the ring.
[0034] For example, Can be expressed Can be expressed Can be expressed And so on.
[0035] The aryl group of the present invention refers to the general term for the group remaining after removing a hydrogen atom from an aromatic carbon nucleus of an aromatic hydrocarbon molecule, which can be a monocyclic aryl group or a condensed ring aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. For example, it can be selected from phenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, benzofluorenyl, spirobifluorenyl, etc., but is not limited thereto.
[0036] The heteroaryl group of the present invention refers to a general term for a group obtained by replacing one or more aromatic carbon atoms in an aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon or phosphorus, and the heteroaryl group may be a monocyclic heteroaryl group or a condensed ring heteroaryl group, preferably having 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. For example, it may be selected from pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, carbazolyl, thienyl, benzothienyl, furyl, benzofuranyl, benzopyrimidinyl, dibenzofuranyl, dibenzothienyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, etc., but is not limited thereto.
[0037] The alkyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from an alkane molecule, and can be a straight-chain alkyl group, a branched-chain alkyl group, or a cycloalkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. For example, the alkyl group can be selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, etc., but is not limited thereto.
[0038] The cycloalkyl group of the present invention refers to a monovalent group formed by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, more preferably 3 to 12 carbon atoms, particularly preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, bornyl, etc., but not limited thereto.
[0039] The heterocycloalkyl group of the present invention refers to a group formed by removing a hydrogen atom from a heterocyclic molecule whose atoms constituting the ring contain at least one heteroatom in addition to carbon atoms, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon or phosphorus, preferably having 1 to 25 carbon atoms, more preferably 1 to 15 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 6 carbon atoms. For example, piperidinyl, piperazinyl, tetrahydropyrrolyl, oxiranyl, cyclothioranyl, propylene, morpholinyl, thiomorpholinyl, etc., but not limited thereto.
[0040] The arylene group of the present invention refers to the general term for the divalent group remaining after removing one hydrogen atom from each of the two aromatic carbon nuclei of the aromatic hydrocarbon molecule, which can be a divalent monocyclic aromatic group or a divalent condensed aromatic group, preferably having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. For example, it can be selected from phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, pyrenyl, perylene, fluorenyl, phenylene fluorenyl, dibenzofluorenyl, spirobifluorenyl, benzospirobifluorenyl, etc., but is not limited thereto.
[0041] The heteroaryl group of the present invention refers to a general term for a group obtained by replacing one or more aromatic core carbons in the aryl group with heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, silicon or phosphorus, and the divalent heteroaryl group may be a divalent monocyclic heteroaryl group or a divalent condensed ring heteroaryl group, preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms. For example, it may be selected from pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, furanylene, thienylene, carbazolylene, benzofuranylene, benzothienylene, benzocarbazolylene, dibenzofuranylene, dibenzothienylene, dibenzocarbazolylene, benzodibenzofuranylene, benzodibenzothienylene, bipyridylene, bipyrimidylene, phenylpyridylene, phenylpyrimidylene, etc., but is not limited thereto.
[0042] The fused cyclic group of an alicyclic ring and an aromatic ring of the present invention refers to a monovalent group formed by removing a hydrogen atom from an alicyclic ring and an aromatic ring after the alicyclic ring and the aromatic ring are fused together. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but is not limited thereto.
[0043] The fused cyclic radical of an alicyclic ring and an aromatic ring of the present invention refers to a divalent group formed by removing two hydrogen atoms after the alicyclic ring and the aromatic ring are fused together. It preferably has 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzocyclopropylene, benzocyclobutylene, benzocyclopentylene, benzocyclohexylene, benzocycloheptylene, naphthocyclopropylene, naphthocyclobutylene, naphthocyclopentylene, naphthocyclohexylene, etc., but is not limited thereto.
[0044] The fused ring group of heterocycloalkane and aromatic ring of the present invention refers to a monovalent group formed by removing a hydrogen atom after the heterocycloalkane and aromatic ring are fused together. It preferably has 6 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 13 carbon atoms, for example, benzopyrrolyl, naphthopyrrolyl, phenanthropyrrolyl, benzazetidinyl, benzazepanyl, benzopiperidinyl, naphthopiperidinyl, phenanthropiperidinyl, etc., but is not limited thereto.
[0045] The fused ring group of an alicyclic ring and a heteroaromatic ring described in the present invention refers to a monovalent group formed by condensing an alicyclic ring and a heteroaromatic ring together and removing a hydrogen atom. It preferably has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, for example, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, dibenzothienocycloheptyl, carbazolylcyclopropyl, carbazolylcyclobutyl, carbazolylcyclopentyl, carbazolylcyclohexyl, carbazolylcycloheptyl, pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl, pyrimidocyclopropyl, pyrimidocyclobutyl, pyrimidocyclopentyl, pyrimidocyclohexyl, pyrimidobenzocycloheptyl,
[0046] The sub-fused cyclic group of an alicyclic ring and a heteroaromatic ring described in the present invention refers to a divalent group formed by removing two hydrogen atoms after an alicyclic ring and a heteroaromatic ring are fused together. It preferably has 5 to 30 carbon atoms, more preferably 5 to 18 carbon atoms, and most preferably 5 to 12 carbon atoms, for example, dibenzofuranocyclopropyl, dibenzofuranocyclobutyl, dibenzofuranocyclopentyl, dibenzofuranocyclohexyl, dibenzofuranocycloheptyl, dibenzothienocyclopropyl, dibenzothienocyclobutyl, dibenzothienocyclopentyl, dibenzothienocyclohexyl, The following examples include, but are not limited to, dibenzothienocycloheptylene, carbazolylcyclopropylene, carbazolylcyclobutylene, carbazolylcyclopentylene, carbazolylcyclohexylene, carbazolylcycloheptylene, pyridocyclopropylene, pyridocyclobutylene, pyridocyclopentylene, pyridocyclohexylene, pyridobenzocycloheptylene, pyrimidocyclopropylene, pyrimidocyclobutylene, pyrimidocyclopentylene, pyrimidocyclohexylene, pyrimidobenzocycloheptylene, and the like, but are not limited to.
[0047] The substituents in the "substituted or unsubstituted" described in the present invention can be independently selected from deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1~C12 alkyl, substituted or unsubstituted C3~C12 cycloalkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C30 heteroaryl, substituted or unsubstituted C1~C12 alkoxy, substituted or unsubstituted C1~C6 alkylthio, substituted or unsubstituted C1~C12 alkylamino, substituted or unsubstituted C6~C30 aryloxy, substituted or unsubstituted C6~C30 arylamino, etc., but are not limited to these, or two adjacent substituents can be connected to form a ring. Deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, C1-C12 alkoxy, and specific examples include deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, phenyl, tolyl, mesityl, pentadeuterated phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, peryl, pyrenyl, fluoranthenyl, fluorenyl, 9,9-dimethylfluorenyl, 9 ,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, spirofluorenyl, 9,9'-spirobifluorenyl, carbazolyl, 9-phenylcarbazolyl, carbazolindolyl, pyrrolyl, furanyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazine, oxazolyl, thiazolyl, imidazolyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzimidazolyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, acridinyl, benzocyclobutane, benzocyclobutene, benzocyclopentane, benzocyclopentene, benzocyclohexane, benzocyclohexene, etc., but are not limited thereto. Or when there are multiple substituents, the multiple substituents may be the same as or different from each other; or adjacent substituents may be connected to form a ring.
[0048] The term "connected to form a ring" used in the present invention refers to two groups connected to each other by a chemical bond and optionally aromatized. For example:
[0049]
[0050] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanebenzophenone, cyclohexene, cyclohexane, cyclohexanebenzophenone, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.
[0051] In the present invention, the term "at least one" includes one, two, three, four or more. The term "two or more" includes two, three, four or more, where permitted.
[0052] The present invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:
[0053]
[0054] Wherein, Ar1 is selected from the structure represented by formula II:
[0055]
[0056] The v is independently selected from any one of CH and N, and at least one of the v is selected from N;
[0057] The z is independently selected from any one of CH and N;
[0058] The R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0059] The a is selected from 0, 1, 2, 3 or 4; when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;
[0060] The b is selected from 0, 1, 2, 3 or 4; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring;
[0061] The c is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring;
[0062] The d is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R4, the two or more R4 are the same or different from each other;
[0063] The Ar2 is selected from any one of the following groups:
[0064]
[0065] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;
[0066] The R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0067] The R x Any one selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring;
[0068] The R y any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring, or Rx , R y are connected to form a substituted or unsubstituted ring;
[0069] The e1 is selected from 0, 1, 2, 3 or 4; when there are two or more R e When two or more R e The same or different from each other, or two adjacent R e are connected to each other to form a substituted or unsubstituted ring;
[0070] The L1, L2, and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring group.
[0071] Preferably, Ar1 is selected from any one of the following groups:
[0072]
[0073] The R4 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthylcyclopropyl, benzocyclobutyl, naphthylcyclobutyl, benzocyclopentyl, naphthylcyclopentyl, benzocyclohexyl, naphthylcyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, any one of naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl and indolyl;
[0074] The d1 is selected from 0, 1, 2, 3, 4, 5 or 6; the d2 is selected from 0, 1, 2, 3, 4 or 5; the d3 is selected from 0, 1, 2, 3 or 4; when two or more R4 are present, the two or more R4 are the same as or different from each other.
[0075] More preferably, Ar1 is selected from any one of the following groups:
[0076]
[0077] Preferably, Ar2 is selected from any one of the following groups:
[0078]
[0079] The x is independently selected from any one of CH and N;
[0080] The R e independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, any one of triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl;
[0081] The R y , R p , R qindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro ...
[0082] The R z selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylmethyl Any one of silanyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;
[0083] The e1 is selected from 0, 1, 2, 3 or 4; the e2 is selected from 0, 1, 2 or 3; the e3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R e When two or more R e The same or different from each other, or two adjacent R e They are connected to each other to form a substituted or unsubstituted ring.
[0084] More preferably, Ar2 is selected from any one of the following groups:
[0085]
[0086]
[0087]
[0088]
[0089] Preferably, the Any one selected from the following groups:
[0090]
[0091] Said X1 and X2 are independently selected from O, S, N (R t )
[0092] X3 is selected from O, S, C(R i R j )、N(R k )
[0093] Said R1, R2, R3, R3' are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthylcyclopropyl, benzocyclobutyl, naphthylcyclobutyl, benzocyclopentyl, naphthylcyclopentyl, benzocyclohexyl, naphthylcyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl , anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzooxazolyl any one of oxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl and phenothiazinyl;
[0094] The R i , R jindependently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl , triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or R i , R j are connected to form a substituted or unsubstituted ring;
[0095] The R t , R k independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl;
[0096] Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c4 is selected from 0, 1, 2, 3 or 4; said c5 is selected from 0, 1, 2 or 3; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring;
[0097] The c'1 is selected from 0, 1, 2, 3 or 4; the c'2 is selected from 0, 1 or 2; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0 or 1; when there are two or more Rc ', two or more R c ' are the same as or different from each other.
[0098] More preferably, the Any one selected from the following groups:
[0099]
[0100]
[0101] Preferably, L1, L2, L3 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0102]
[0103] The r is independently selected from any one of CH and N;
[0104] The Y a , Y b independently selected from O, S, N(R s )
[0105] The Y c , Y d , Y e independently selected from O, S, C(R m R n )、N(R v )
[0106] The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0107] The R h , R h 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group;
[0108] The R m , R nis independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R m , R n are connected to form a substituted or unsubstituted ring;
[0109] The R s , R v Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
[0110] Said p is selected from 1, 2, 3 or 4;
[0111] The h1 is selected from 0, 1, 2, 3 or 4; the h2 is selected from 0, 1, 2, 3, 4, 5 or 6; the h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the h4 is selected from 0, 1 or 2; when there are two or more R h When two or more R h The same or different from each other, or two adjacent R h are connected to each other to form a substituted or unsubstituted ring;
[0112] The h'1 is selected from 0, 1 or 2; when there are two or more R h ', two or more R h ' are the same as or different from each other.
[0113] More preferably, L1, L2, and L3 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0114]
[0115] The R h , R h' is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, benzocyclopropyl, naphthocyclopropyl, cyclobutyl, benzocyclobutyl, naphthocyclobutyl, cyclopentyl, benzocyclopentyl, naphthocyclopentyl, cyclohexyl, benzocyclohexyl, naphthocyclohexyl, cycloheptyl, benzocycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazine any one of 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 51, 52, 53, 54, 55, 56, 57, 58, 59, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 101, 102, 114, 115, 126, 136, 147, 159, 119, 127, 137, 148, 15
[0116] The R m , R n independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, benzocyclopropyl, naphthocyclopropyl, cyclobutyl, benzocyclobutyl, naphthocyclobutyl, cyclopentyl, benzocyclopentyl, naphthocyclopentyl, cyclohexyl, benzocyclohexyl, naphthocyclohexyl, cycloheptyl, benzocycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0117] The R s , R vindependently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, benzocyclopropyl, naphthocyclopropyl, cyclobutyl, benzocyclobutyl, naphthocyclobutyl, cyclopentyl, benzocyclopentyl, naphthocyclopentyl, cyclohexyl, benzocyclohexyl, naphthocyclohexyl, cycloheptyl, benzocycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0118] h'1 is selected from 0, 1 or 2; h'2 is selected from 0, 1, 2, 3 or 4; h'3 is selected from 0, 1, 2, 3, 4, 5 or 6; h'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; h'5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R h ', two or more R h ' are the same as or different from each other.
[0119] More preferably, L1, L2, L3 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0120]
[0121]
[0122] Most preferably, the formula I is selected from any one of the following structures:
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139] Some specific structural forms of the aromatic amine compounds represented by Chemical Formula I of the present invention are listed above, but the present invention is not limited to these listed chemical structures, and all structures based on the structure shown in Chemical Formula I and having substituents as defined above should be included.
[0140] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer located between the anode and the cathode or located on the side of the cathode away from the anode, wherein the organic layer contains at least one of the aromatic amine compounds described in the present invention.
[0141] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises at least one of a hole transport layer and a charge generation layer, and at least one of the hole transport layer and the charge generation layer comprises at least one of the aromatic amine compounds described in the present invention.
[0142] More preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises at least one of the aromatic amine compounds described in the present invention.
[0143] More preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, the third hole transport layer is located between the second hole transport layer and the light-emitting layer, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer comprises at least one of the aromatic amine compounds described in the present invention.
[0144] More preferably, the organic layer is located between the anode and the cathode, the organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generating layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generating layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generating layer comprises at least one of the aromatic amine compounds described in the present invention.
[0145] More preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, and the charge generation layer includes a P-type charge generation layer, and the P-type charge generation layer includes at least one of the aromatic amine compounds described in the present invention.
[0146] Preferably, the organic layer is located on a side of the cathode facing away from the anode, and the organic layer comprises a covering layer, and the covering layer comprises at least one of the aromatic amine compounds described in the present invention.
[0147] The anode of the present invention is preferably a high work function material that can promote hole injection into the organic layer, and may include metals, metal oxides or multilayer structures, such as vanadium, chromium, copper, zinc and gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), ITO / Ag / ITO, Al / Ag, etc., but is not limited thereto.
[0148] The hole injection layer of the present invention preferably has a material with good hole acceptance ability. In addition to the aromatic amine compounds provided by the present invention, triarylamine compounds, porphyrin compounds, styrene compounds, polythiophene and its derivatives, phthalocyanine derivatives, axialene compounds and other substances with high hole injection properties may also be included, such as 4,4',4"-tri[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(styrene sulfonic acid) (PEDOT / PSS), etc., but not limited thereto. The aromatic amine compounds of the present invention are preferred.
[0149] The hole transport layer of the present invention preferably has a material with excellent hole transport performance. In addition to the aromatic amine compound provided by the present invention, it can also include carbazole derivatives, fluorene derivatives, biphenyl diamine derivatives, triarylamine derivatives, stilbene derivatives, phthalocyanine compounds, anthraquinone compounds, quinacridone compounds, hexanitrile hexaazatriphenylene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc., such as N, N'-diphenyl-N, N'-(1-naphthyl)-1, 1'-biphenyl-4, 4'-diamine (NPB), N, N'-diphenyl-N, N'-di (3-methylphenyl) -1, 1'-biphenyl-4, 4'-diamine (TPD), N, N'-di (4-biphenyl) -N, N'-diphenyl benzidine, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0150] The electron blocking layer of the present invention preferably has a material with good hole transport ability and the ability to block electrons. In addition to the aromatic amine compound provided by the present invention, aromatic amine derivatives, carbazole derivatives, etc. may also be included. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), etc., but are not limited thereto. The aromatic amine compound of the present invention is preferred.
[0151] The light-emitting layer of the present invention may contain only a guest material, or a guest material may be dispersed in a host material. The guest material may be a fluorescent compound, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, such as C545T, BCzVBi, DPAVBi, etc.; a phosphorescent luminescent material may also be used, such as a metal complex such as an iridium complex, an osmium complex, a platinum complex, such as FIrpic, Ir(ppy)3, Ir(ppy)2(acac), etc. The host material preferably uses a substance having a higher LUMO energy level 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 anthracene derivative, an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative, such as Alq3, BAlq, TPBi, TPD, CBP, TCTA, ADN, etc., but is not limited thereto.
[0152] The hole blocking layer of the present invention is a layer that prevents holes from reaching the cathode, and can usually be formed using the same conditions as the hole injection layer. It can include aluminum complexes, lithium complexes, beryllium complexes, oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, phenanthroline derivatives, polymer compounds, etc., such as TPBi, BAlq, etc., but not limited thereto.
[0153] The electron transport layer of the present invention uses a material with high electron transport properties, which may include metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives and other aromatic heterocyclic compounds, polymer compounds, etc., such as Alq3, BeBq2, BAlq, PBD, ZnPBO, PBD, BPhen, etc., but not limited thereto.
[0154] The electron injection layer of the present invention uses a material with high electron injection property, which may include alkali metals, alkaline earth metals, alkali metal salts, alkaline earth metal salts, metal oxides, etc., such as LiF, CsF, Al2O3, Yb, Mg, Ca, Li, Sr, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Tb, etc., but is not limited thereto.
[0155] The cathode of the present invention is preferably a low work function material, which may include metals, metal alloys or multilayer structures, such as alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium and strontium, alloys containing these metals (such as MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), alloys containing rare earth metals, etc., but are not limited thereto.
[0156] The cover layer material of the present invention is preferably a material having a light coupling effect. In addition to the aromatic amine compound provided by the present invention, it may also include metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc., such as Alq3, LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0157] The P-type charge generation layer material of the present invention includes an organic material doped with a metal or a P-type dopant. In addition to the aromatic amine compound provided by the present invention, it may also include an alloy of one or two of the group consisting of aluminum (Al), copper (Cu), iron (Fe), lead (Pb), zinc (Zn), gold (Au), platinum (Pt), tungsten (W), indium (In), molybdenum (Mo), nickel (Ni) and titanium (Ti). The P-type dopant may include F4-TCNQ, iodine (I), ferric chloride (FeCl3), ferric fluoride (FeF3) and antimony chloride (SbCl5), and the main body may include at least one selected from the group consisting of NPB, TPD, TNB and HAT-CN, but is not limited thereto. The aromatic amine compound of the present invention is preferred.
[0158] The N-type charge generation layer materials described in the present invention include N-type doped organic materials such as alkali metals such as Li, Na, K, Rb, Cs, Fr, etc.; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, Ra, etc.; Group 15 metals such as Bi (bismuth) and Sb (antimony); lanthanide metals such as La (lanthanum), Ce (cerium), Pr (praseodymium), Nd (neodymium), Pm (promethium), Sm (samarium), Gd (gadolinium), etc.; and more than one of the above metal compounds, etc. In addition, it can also be an organic N-type dopant that has electron-donating properties and can supply at least a portion of the electron charge to the organic host and form a charge transfer complex with the organic host. Examples thereof include BEDT-TTF, TTF, etc., but are not limited thereto.
[0159] The following is a method for preparing the compound represented by the chemical formula I of the present invention, but the preparation method of the present invention is not limited thereto. The core structure of the compound of the chemical formula I can be prepared by the reaction route shown below, the substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be changed according to techniques known in the art.
[0160] [Synthetic route]
[0161] Preparation of compounds of formula I:
[0162]
[0163] Xa and Xb are each independently selected from any one of Cl, Br, and I; the definitions of Ar1, Ar2, L1, L2, L3, R1, R2, R3, a, b, c, and z are the same as those above.
[0164] Description of raw materials, reagents and characterization equipment:
[0165] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. The raw materials and reagents may be commercially available products or prepared by methods well known to those skilled in the art.
[0166] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;
[0167] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar of Germany, with a sample mass of 5 to 10 mg.
[0168] [Synthesis Example 1] Synthesis of Compound 2
[0169]
[0170] Preparation of intermediate A-2:
[0171] Under nitrogen protection, toluene (450mL), a-2 (10.81g, 75.00mmol), b-2 (29.80g, 75.00mmol), sodium tert-butoxide (14.42g, 150.00mmol), palladium acetate (0.25g, 1.13mmol) and tri-tert-butylphosphine (9.00ml, 4.50mmol) were added to the reaction bottle and refluxed for 3.5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extracted with dichloromethane, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene: ethanol (5:1) to obtain A-2 (29.36g, yield 85%), and the solid purity was ≥99.86% by HPLC. Mass spectrum m / z: 460.1927 (theoretical value: 460.1939).
[0172] Preparation of compound 2:
[0173] Under nitrogen protection, toluene (300mL), A-2 (18.42g, 40.00mmol), c-2 (13.41g, 40.00mmol), sodium tert-butoxide (7.69g, 80.00mmol), tridibenzylideneacetone palladium (0.37g, 0.40mmol) and X-phos (0.38mL, 0.80mmol) were added to the reaction bottle and refluxed for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, extracted with chloroform, the organic phase was dried with anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 2 (20.88g, yield 73%). The solid purity was ≥99.99% detected by HPLC. Mass spectrum m / z: 714.3049 (theoretical value: 714.3035). Theoretical element content (%) C 54 H 38 N2: C, 90.72; H, 5.36; N, 3.92. Measured element content (%): C, 90.73; H, 5.34; N, 3.91.
[0174] [Synthesis Example 2] Synthesis of Compound 39
[0175]
[0176] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-39, and c-2 was replaced by an equal mole of c-39 to obtain compound 39 (22.04 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 786.3803 (theoretical value: 786.3819). Theoretical element content (%) C 59 H 30 D 10N2: C, 90.04; H, 6.40; N, 3.56. Measured element content (%): C, 90.05; H, 6.43; N, 3.57.
[0177] [Synthesis Example 3] Synthesis of Compound 58
[0178]
[0179] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-58 to obtain compound 58 (22.22 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 804.3516 (theoretical value: 804.3504). Theoretical element content (%) C 61 H 44 N2: C, 91.01; H, 5.51; N, 3.48. Measured element content (%): C, 91.02; H, 5.53; N, 3.46.
[0180] [Synthesis Example 4] Synthesis of Compound 93
[0181]
[0182] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-93, and c-2 was replaced by an equal mole of c-93 to obtain compound 93 (23.83 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 888.4454 (theoretical value: 888.4443). Theoretical element content (%) C 67 H 56 N2: C, 90.50; H, 6.35; N, 3.15. Measured element content (%): C, 90.53; H, 6.36; N, 3.14.
[0183] [Synthesis Example 5] Synthesis of Compound 99
[0184]
[0185] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-58, b-2 was replaced by an equal molar amount of b-99, and c-2 was replaced by an equal molar amount of c-99 to obtain Compound 99 (22.54 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 804.3521 (theoretical value: 804.3504). Theoretical element content (%) C 61 H 44N2: C, 91.01; H, 5.51; N, 3.48. Measured element content (%): C, 91.03; H, 5.52; N, 3.45.
[0186] [Synthesis Example 6] Synthesis of Compound 104
[0187]
[0188] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-104 to obtain compound 104 (23.10 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 848.3572 (theoretical value: 848.3587). Theoretical element content (%) C 62 H 48 N2Si: C, 87.70; H, 5.70; N, 3.30. Measured element content (%): C, 87.72; H, 5.71; N, 3.33.
[0189] [Synthesis Example 7] Synthesis of Compound 107
[0190]
[0191] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-107 to obtain compound 107 (22.83 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 826.3335 (theoretical value: 826.3348). Theoretical element content (%) C 63 H 42 N2: C, 91.49; H, 5.12; N, 3.39. Measured element content (%): C, 91.47; H, 5.13; N, 3.38.
[0192] [Synthesis Example 8] Synthesis of Compound 112
[0193]
[0194] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-112 to obtain compound 112 (23.24 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 866.3672 (theoretical value: 866.3661). Theoretical element content (%) C 66 H 46 N2: C, 91.42; H, 5.35; N, 3.23. Measured element content (%): C, 91.45; H, 5.34; N, 3.22.
[0195] [Synthesis Example 9] Synthesis of Compound 153
[0196]
[0197] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-153 to obtain compound 153 (23.42 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 886.4272 (theoretical value: 886.4287). Theoretical element content (%) C 67 H 54 N2: C, 90.71; H, 6.14; N, 3.16. Measured element content (%): C, 90.72; H, 6.15; N, 3.14.
[0198] [Synthesis Example 10] Synthesis of Compound 177
[0199]
[0200] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-58, and c-2 was replaced by an equal mole of c-177 to obtain compound 177 (22.46 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 790.2973 (theoretical value: 790.2984). Theoretical element content (%) C 59 H 38 N2O: C, 89.59; H, 4.84; N, 3.54. Measured element content (%): C, 89.58; H, 4.85; N, 3.52.
[0201] [Synthesis Example 11] Synthesis of Compound 208
[0202]
[0203] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-208, and c-2 was replaced by an equal mole of c-208 to obtain compound 208 (23.20 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 852.3516 (theoretical value: 852.3504). Theoretical element content (%) C 65 H 44 N2: C, 91.52; H, 5.20; N, 3.28. Measured element content (%): C, 91.53; H, 5.22; N, 3.26.
[0204] [Synthesis Example 12] Synthesis of Compound 221
[0205]
[0206] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-221, and c-2 was replaced by an equal mole of c-208 to obtain compound 221 (22.86 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 852.3515 (theoretical value: 852.3504). Theoretical element content (%) C 65 H 44 N2: C, 91.52; H, 5.20; N, 3.28. Measured element content (%): C, 91.53; H, 5.21; N, 3.25.
[0207] [Synthesis Example 13] Synthesis of Compound 227
[0208]
[0209] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-227, and c-2 was replaced by an equal mole of c-227 to obtain compound 227 (23.68 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 857.3806 (theoretical value: 857.3818). Theoretical element content (%) C 65 H 39 D5N2: C, 90.98; H, 5.75; N, 3.26. Measured element content (%): C, 90.95; H, 5.76; N, 3.24.
[0210] [Synthesis Example 14] Synthesis of Compound 231
[0211]
[0212] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-227, b-2 was replaced by an equal mole of b-231, and c-2 was replaced by an equal mole of c-208 to obtain Compound 231 (23.34 g). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 857.3832 (theoretical value: 857.3818). Theoretical element content (%) C 65 H 39 D5N2: C, 90.98; H, 5.75; N, 3.26. Measured element content (%): C, 90.96; H, 5.74; N, 3.25.
[0213] [Synthesis Example 15] Synthesis of Compound 285
[0214]
[0215] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-285, b-2 was replaced by an equal molar amount of b-285, and c-2 was replaced by an equal molar amount of c-285 to obtain Compound 285 (24.37 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 908.4143 (theoretical value: 908.4130). Theoretical element content (%) C 69 H 52 N2: C, 91.15; H, 5.77; N, 3.08. Measured element content (%): C, 91.18; H, 5.75; N, 3.07.
[0216] [Synthesis Example 16] Synthesis of Compound 303
[0217]
[0218] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-227, b-2 was replaced by an equal mole of b-303, and c-2 was replaced by an equal mole of c-208 to obtain compound 303 (23.64 g). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 908.4115 (theoretical value: 908.4130). Theoretical element content (%) C 69 H 52 N2: C, 91.15; H, 5.77; N, 3.08. Measured element content (%): C, 91.16; H, 5.75; N, 3.07.
[0219] [Synthesis Example 17] Synthesis of Compound 346
[0220]
[0221] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-346, and c-2 was replaced by an equal mole of c-346 to obtain compound 346 (23.29 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 868.3241 (theoretical value: 868.3254). Theoretical element content (%) C 65 H 41 FN2: C, 89.83; H, 4.76; N, 3.22. Measured element content (%): C, 89.85; H, 4.73; N, 3.21.
[0222] [Synthesis Example 18] Synthesis of Compound 362
[0223]
[0224] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-362, and c-2 was replaced by an equal mole of c-362 to obtain compound 362 (22.66 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 820.3828 (theoretical value: 820.3817). Theoretical element content (%) C 62 H 48 N2: C, 90.70; H, 5.89; N, 3.41. Measured element content (%): C, 90.73; H, 5.88; N, 3.42.
[0225] [Synthesis Example 19] Synthesis of Compound 560
[0226]
[0227] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-560, b-2 was replaced by an equal molar amount of b-560, and c-2 was replaced by an equal molar amount of c-560 to obtain Compound 560 (22.63 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 831.3625 (theoretical value: 831.3613). Theoretical element content (%) C 62 H 45 N3: C, 89.50; H, 5.45; N, 5.05. Measured element content (%): C, 89.52; H, 5.48; N, 5.06.
[0228] [Synthesis Example 20] Synthesis of Compound 571
[0229]
[0230] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-571, b-2 was replaced by an equal molar amount of b-571, and c-2 was replaced by an equal molar amount of c-208 to obtain Compound 571 (23.84 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 902.3675 (theoretical value: 902.3661). Theoretical element content (%) C 69 H 46 N2: C, 91.76; H, 5.13; N, 3.10. Measured element content (%): C, 91.78; H, 5.15; N, 3.11.
[0231] [Synthesis Example 21] Synthesis of Compound 580
[0232]
[0233] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-58, b-2 was replaced by an equal molar amount of b-580, and c-2 was replaced by an equal molar amount of c-208 to obtain compound 580 (24.40 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 952.3803 (theoretical value: 952.3817). Theoretical element content (%) C 73 H 48 N2: C, 91.99; H, 5.08; N, 2.94. Measured element content (%): C, 91.97; H, 5.06; N, 2.91.
[0234] [Synthesis Example 22] Synthesis of Compound 601
[0235]
[0236] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-601, b-2 was replaced by an equal molar amount of b-601, and c-2 was replaced by an equal molar amount of c-208 to obtain compound 601 (23.23 g). The solid purity was ≥ 99.94% by HPLC. Mass spectrum m / z: 853.3443 (theoretical value: 853.3457). Theoretical element content (%) C 64 H 43 N3: C, 90.00; H, 5.07; N, 4.92. Measured element content (%): C, 90.02; H, 5.06; N, 4.93.
[0237] [Synthesis Example 23] Synthesis of Compound 630
[0238]
[0239] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-630, and c-2 was replaced by an equal mole of c-630 to obtain compound 630 (23.87 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 903.3625 (theoretical value: 903.3613). Theoretical element content (%) C 68 H 45 N3: C, 90.34; H, 5.02; N, 4.65. Measured element content (%): C, 90.35; H, 5.03; N, 4.67.
[0240] [Synthesis Example 24] Synthesis of Compound 637
[0241]
[0242] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal mole of a-637, and c-2 was replaced by an equal mole of c-208 to obtain compound 637 (24.18 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 929.3786 (theoretical value: 929.3770). Theoretical element content (%) C 70 H 47 N3: C, 90.39; H, 5.09; N, 4.52. Measured element content (%): C, 90.38; H, 5.06; N, 4.53.
[0243] [Synthesis Example 25] Synthesis of Compound 676
[0244]
[0245] According to the preparation method of Synthesis Example 1, a-2 was replaced by an equal molar amount of a-676, b-2 was replaced by an equal molar amount of b-676, and c-2 was replaced by an equal molar amount of c-676 to obtain compound 676 (22.18 g). The solid purity was ≥ 99.99% as determined by HPLC. Mass spectrum m / z: 769.3441 (theoretical value: 769.3457). Theoretical element content (%) C 57 H 43 N3: C, 88.91; H, 5.63; N, 5.46. Measured element content (%): C, 88.94; H, 5.61; N, 5.45.
[0246] [Device Example]
[0247] The test software, computer, K2400 digital source meter produced by Keithley Company of the United States and PR788 spectrum scanning luminance meter produced by PhotoResearch Company of the United States are combined into a joint IVL test system to test the luminous efficiency of organic electroluminescent devices. The life test adopts the M6000 OLED life test system of McScience Company.
[0248] [Example 1]
[0249] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-1 was evaporated on the anode to form a thickness of The hole injection layer is formed by evaporating the compound 2 of the present invention on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is deposited on the hole transport layer. The light-emitting layer is formed by evaporating GH-1 as the main material of the light-emitting layer and doping 6wt% of GD-1 to form a layer with a thickness of ET-1:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0250]
[0251] [Examples 2 to 25]
[0252] The compound 39, compound 58, compound 93, compound 99, compound 104, compound 107, compound 112, compound 153, compound 177, compound 208, compound 221, compound 227, compound 231, compound 285, compound 303, compound 346, compound 362, compound 560, compound 571, compound 580, compound 601, compound 630, compound 637 and compound 676 of the present invention were used to replace compound 2 in Example 1 as hole transport layer materials, except that an organic electroluminescent device was prepared by the same preparation method as Example 1.
[0253] [Comparative Examples 1 to 3]
[0254] Organic electroluminescent devices were prepared by the same preparation method as in Example 1 except that Compound P-1, Compound P-2 and Compound P-3 were used to replace Compound 2 in Example 1 as hole transport layer materials.
[0255] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the devices 1 to 25 in the embodiments of the present invention and the comparative examples 1 to 3 are shown in Table 1 below.
[0256] Table 1:
[0257]
[0258]
[0259] From the results in Table 1, it can be seen that when the aromatic amine compound described in the present invention is applied to the hole transport layer of an organic electroluminescent device, compared with the comparative compounds P-1 to P-3, the device has higher luminous efficiency and longer service life. The aromatic amine compound of the present invention is a hole transport layer material with good performance.
[0260] [Example 26]
[0261] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. Indium tin oxide (ITO) was coated on the glass substrate to form an anode. HI-2 was evaporated on the anode to form a thickness of HT-2 is evaporated on the hole injection layer to form a hole injection layer with a thickness of The first hole transport layer is formed by evaporating the compound 2 of the present invention on the first hole transport layer to form a layer with a thickness of The second hole transport layer is deposited on the second hole transport layer. The light-emitting layer is formed by evaporating BH-2 as the main material of the light-emitting layer and doping 4wt% of BD-2 to form a thickness of ET-2 is evaporated on the luminescent layer to form a luminescent layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Al is evaporated on the electron injection layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0262]
[0263] [Examples 27 to 50]
[0264] The compound 39, compound 58, compound 93, compound 99, compound 104, compound 107, compound 112, compound 153, compound 177, compound 208, compound 221, compound 227, compound 231, compound 285, compound 303, compound 346, compound 362, compound 560, compound 571, compound 580, compound 601, compound 630, compound 637 and compound 676 of the present invention were used to replace compound 2 in Example 26 as the second hole transport layer material. Except for this, an organic electroluminescent device was prepared by the same preparation method as Example 26.
[0265] [Comparative Examples 4 to 5]
[0266] An organic electroluminescent device was prepared by the same preparation method as in Example 26 except that Compound P-4 and Compound P-5 were used to replace Compound 2 in Example 26 as the second hole transport layer material.
[0267] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the embodiments 26 to 50 of the present invention and comparative embodiments 4 to 5 are shown in Table 2 below.
[0268] Table 2:
[0269]
[0270]
[0271] It can be seen from the results in Table 2 that when the aromatic amine compound described in the present invention is applied to the second hole transport layer of the organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-4 to P-5. The compound of the present invention is a second hole transport layer material with good performance.
[0272] [Example 51]
[0273] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water washing, ultrasonic washing was performed using solvents such as isopropyl alcohol, acetone, and methanol, and then dried. After drying, the substrate was transferred to a plasma cleaning machine, and after washing, the substrate was transferred to an evaporator. ITO / Ag / ITO was coated on the glass substrate to form an anode. HI-3 was evaporated on the anode to form a thickness of HT-3 is evaporated on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is deposited on the hole transport layer. The light-emitting layer is formed with BH-3 as the main material of the light-emitting layer and 5 wt% of BD-3 doped to form a hole transport layer with a thickness of ET-2:LiQ (mass ratio 1:1) was evaporated on the luminescent layer to form a layer with a thickness of The electron transport layer is formed by evaporating LiF on the electron transport layer to form a layer with a thickness of Mg:Ag (mass ratio 1:9) was evaporated on the electron injection layer to form a layer with a thickness of The present invention compound 2 is evaporated on the cathode layer to form a cathode with a thickness of Thus, an organic light-emitting device is formed.
[0274]
[0275] [Examples 52 to 75]
[0276] Compound 39, compound 58, compound 93, compound 99, compound 104, compound 107, compound 112, compound 153, compound 177, compound 208, compound 221, compound 227, compound 231, compound 285, compound 303, compound 346, compound 362, compound 560, compound 571, compound 580, compound 601, compound 630, compound 637 and compound 676 of the present invention were used to replace compound 2 in Example 51 as covering layer materials, except that an organic electroluminescent device was prepared by the same preparation method as Example 51.
[0277] [Comparative Examples 6 to 7]
[0278] An organic electroluminescent device was prepared by the same preparation method as that of Device Example 51, except that Compound P-6 and Compound P-7 were used to replace Compound 2 in Device Example 51 as the covering layer material.
[0279] The test environment is an atmospheric environment and the temperature is room temperature. The test results of the luminescence characteristics of the organic electroluminescent devices obtained in the devices 51 to 75 in the embodiments of the present invention and the comparative examples 6 to 7 are shown in Table 3 below.
[0280] Table 3:
[0281]
[0282]
[0283] The results in Table 3 show that when the aromatic amine compound of the present invention is applied to the covering layer of an organic electroluminescent device, the device has higher luminous efficiency and longer service life than the comparative compounds P-6 to P-7. The compound of the present invention is a covering layer material with good performance.
[0284] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.
Claims
1. An aromatic amine compound, characterized in that The aromatic amine compound has a structure represented by Formula I: Wherein, Ar1 is selected from the structure represented by formula II: The v is independently selected from any one of CH and N, and at least one of the v is selected from N; The z is independently selected from any one of CH and N; The R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; The a is selected from 0, 1, 2, 3 or 4; when there are two or more R1, the two or more R1 are the same or different from each other, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring; The b is selected from 0, 1, 2, 3 or 4; when there are two or more R2, the two or more R2 are the same or different from each other, or two adjacent R2 are connected to each other to form a substituted or unsubstituted ring; The c is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R3, the two or more R3 are the same or different from each other, or two adjacent R3 are connected to each other to form a substituted or unsubstituted ring; The d is selected from 0, 1, 2, 3, 4, 5 or 6; when there are two or more R4, the two or more R4 are the same or different from each other; The Ar2 is selected from any one of the following groups: The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring; The R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; The R x Any one selected from a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, and a fused ring group of a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring; The R y any one selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring, or R x , R y are connected to form a substituted or unsubstituted ring; The e1 is selected from 0, 1, 2, 3 or 4; when there are two or more R e When two or more R e The same or different from each other, or two adjacent R e are connected to each other to form a substituted or unsubstituted ring; The L1, L2, and L3 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring condensed ring group, and a substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic ring condensed ring group.
2. An aromatic amine compound according to claim 1, characterized in that: The Ar1 is selected from any one of the following groups: The R4 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthylcyclopropyl, benzocyclobutyl, naphthylcyclobutyl, benzocyclopentyl, naphthylcyclopentyl, benzocyclohexyl, naphthylcyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, any one of naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl and indolyl; The d1 is selected from 0, 1, 2, 3, 4, 5 or 6; the d2 is selected from 0, 1, 2, 3, 4 or 5; the d3 is selected from 0, 1, 2, 3 or 4; when two or more R4 are present, the two or more R4 are the same as or different from each other.
3. An aromatic amine compound according to claim 1, characterized in that: The Ar2 is selected from any one of the following groups: The x is independently selected from any one of CH and N; The R e independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, any one of triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl; The R y , R p , R q independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilane any one of 1,2-dimethyl-1,2-dihydro ... The R z selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylmethyl Any one of silanyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; The e1 is selected from 0, 1, 2, 3 or 4; the e2 is selected from 0, 1, 2 or 3; the e3 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R e When two or more R e The same or different from each other, or two adjacent R e They are connected to each other to form a substituted or unsubstituted ring.
4. An aromatic amine compound according to claim 1, characterized in that: Said Any one selected from the following groups: Said X1 and X2 are independently selected from O, S, N (R t ) X3 is selected from O, S, C(R i R j )、N(R k ) Said R1, R2, R3, R3' are independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthylcyclopropyl, benzocyclobutyl, naphthylcyclobutyl, benzocyclopentyl, naphthylcyclopentyl, benzocyclohexyl, naphthylcyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl , anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzooxazolyl any one of oxazolyl, dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl and phenothiazinyl; The R i , R j independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl , triethylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or R i , R j are connected to form a substituted or unsubstituted ring; The R t , R k independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, any one of methylsilyl, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl and triazinyl; Said c1 is selected from 0, 1, 2, 3, 4 or 5; said c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said c4 is selected from 0, 1, 2, 3 or 4; said c5 is selected from 0, 1, 2 or 3; when there are two or more R c When two or more R c The same or different from each other, or two adjacent R c are connected to each other to form a substituted or unsubstituted ring; The c'1 is selected from 0, 1, 2, 3 or 4; the c'2 is selected from 0, 1 or 2; the c'3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c'4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c'5 is selected from 0 or 1; when there are two or more R c ', two or more R c ' are the same as or different from each other.
5. An aromatic amine compound according to claim 1, characterized in that: Said Any one selected from the following groups:
6. An aromatic amine compound according to claim 1, characterized in that: The L1, L2, and L3 are independently selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The r is independently selected from any one of CH and N; The Y a , Y b independently selected from O, S, N(R s ) The Y c , Y d , Y e independently selected from O, S, C(R m R n )、N(R v ) The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings; The R h , R h 'Independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group; The R m , R n is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or R m , R n are connected to form a substituted or unsubstituted ring; The R s , R v Any one independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C1-C25 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; Said p is selected from 1, 2, 3 or 4; The h1 is selected from 0, 1, 2, 3 or 4; the h2 is selected from 0, 1, 2, 3, 4, 5 or 6; the h3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the h4 is selected from 0, 1 or 2; when there are two or more R h When two or more R h The same or different from each other, or two adjacent R h are connected to each other to form a substituted or unsubstituted ring; The h'1 is selected from 0, 1 or 2; when there are two or more R h ', two or more R h ' are the same as or different from each other.
7. An aromatic amine compound according to claim 1, characterized in that: The formula I is selected from any 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 or located on a side of the cathode away from the anode, characterized in that: The organic layer contains at least one of the aromatic amine compounds according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode or on a side of the cathode away from the anode, wherein: The organic layer comprises at least one of a hole transport layer and a covering layer, and the at least one of the hole transport layer and the covering layer comprises at least one of the aromatic amine compounds according to any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, wherein: The organic layer comprises a first light-emitting portion, a second light-emitting portion and a charge generation layer, the first light-emitting portion is located between the anode and the cathode, the second light-emitting portion is located between the first light-emitting portion and the cathode, the charge generation layer is located between the first light-emitting portion and the second light-emitting portion, and the charge generation layer comprises at least one of the aromatic amine compounds described in any one of claims 1 to 7.