Arylamine compound and organic electroluminescent device thereof
By using new aromatic amine compounds as hole transport materials, cover material or charge generation layer material in organic electroluminescent devices, the problem of insufficient luminescence efficiency and service life in the prior art is solved, and higher luminescence is achieved Efficiency and longer service life.
Patent Information
- Application Number
- CN202411595033.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-11-08
- Publication Date
- 2025-02-18
- Estimated Expiration
- Not applicable · inactive patent
AI Technical Summary
There is room for improvement in the luminous efficiency and service life of existing organic electroluminescent devices, especially in the performance of hole transport materials, cover materials and charge generation materials.
A new aromatic amine compound is used as a hole transport material, a cover material or a charge generation layer material, and the luminescence efficiency of the device is improved and service life is extended through its excellent physical and chemical properties.
The aromatic amine compound can increase hole transfer rate, reduce energy barriers, enhance luminescence efficiency, and extend the service life of the device by reducing light loss.
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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 development of the times, organic electroluminescent devices have shown potential application value in display fields such as mobile phones, digital products, and car audio and video, and will have a larger market in the future flat panel display and lighting fields. Compared with traditional liquid crystal displays, organic electroluminescent device displays have significant characteristics such as light and thin body, wide viewing angle, fast response speed, wide operating temperature range, low energy consumption, high efficiency, good color purity, high clarity, and good flexibility. They have obvious advantages in the display and lighting fields and have broad application prospects, which has attracted widespread attention.
[0003] The basic principle of organic electroluminescence is that under the drive of external voltage, electrons are injected from the cathode into the organic matter; holes are injected from the anode into the organic functional layer. When electrons and holes recombine in the light-emitting layer to form excitons, the excitons emit light through radiation decay.
[0004] Organic electroluminescent devices (OLEDs) are sandwich devices. The organic functional layer of the device is sandwiched between the electrode layers on both sides like a sandwich, and one side is a transparent electrode to facilitate light emission. The organic functional layer can be divided into a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a covering layer, a charge generation layer, etc. according to their functions. Among them, the hole transport material can increase the transmission rate of holes in the device, so that the hole transmission rate and the electron transmission rate are balanced, so that holes and electrons can be effectively combined in the light-emitting layer, and the hole transport material with excellent performance can reduce the energy barrier in the hole injection process, so that the hole injection efficiency is improved, thereby achieving the improvement of the luminous efficiency of the device and the extension of the service life; when the covering layer material is applied to the device, it can effectively reduce the light loss reflected by the nearby electrode during light emission, thereby improving the luminous efficiency of the device and extending the service life of the device; when the charge generation layer material is applied to the stacked device, each light-emitting unit can emit light independently, and the luminous efficiency is significantly improved compared with the single-layer device, and the service life is greatly extended.
[0005] In order to obtain organic electroluminescent devices with higher luminous efficiency and longer service life, it is worth considering how to find hole transport materials, covering layer materials, and charge generation layer materials with excellent performance. 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 Formula II:
[0010]
[0011] The z is selected from any one of CH and N;
[0012] X1 is selected from O, S, N (R s )
[0013] The R1, R2, R a , R a '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;
[0014] The R s Any one selected from hydrogen, deuterium, tritium, 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;
[0015] 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 or 3; 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 a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a They are connected to each other to form a substituted or unsubstituted aromatic ring;
[0017] The Ar2 is selected from any one of the following structures:
[0018]
[0019] The v is selected from any one of CH and N;
[0020] The R p , R q , R p '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;
[0021] The R b , R c 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-C18 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;
[0022] The R d , R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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;
[0023] The b1 is selected from 0, 1, 2, 3 or 4; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; the c1 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 d1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R d When two or more R d The same or different from each other, or two adjacent R d are connected to each other to form a substituted or unsubstituted ring; said e1 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 are connected to each other to form a substituted or unsubstituted ring;
[0024] The Ar3 and Ar4 are independently selected from any one of the following structures:
[0025]
[0026] The x is selected from any one of CH and N;
[0027] The X2 and X3 are independently selected from O, S, N (R u )
[0028] X4 is selected from O, S, C(R i R j )、N(R w )
[0029] The R r , R r '、R i , R jR is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, or R i , R j are connected to form a substituted or unsubstituted ring;
[0030] The R u , R w Any one independently selected from hydrogen, deuterium, tritium, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring;
[0031] Said r1 is selected from 0, 1, 2, 3, 4 or 5; said r2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said r4 is selected from 0, 1, 2, 3 or 4; said r5 is selected from 0, 1 or 2; said r6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said r7 is selected from 0, 1, 2 or 3; when there are two or more R r When two or more R r The same or different from each other, or two adjacent R r They are connected to each other to form a substituted or unsubstituted aromatic ring;
[0032] The r'1 is selected from 0, 1 or 2; when there are two or more R r ', two or more R r 'same or different from each other;
[0033] The L1 is 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 group and a C6-C30 aromatic ring condensed sub-cyclic group, a substituted or unsubstituted C3-C25 alicyclic group and a C2-C30 heteroaromatic ring condensed sub-cyclic group; wherein the substituent in the "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, C1-C25 alkyl, C3-C12 cycloalkyl, C1-C25 heterocycloalkyl, and C6-C30 aryl;
[0034] The 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.
[0035] 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.
[0036] Beneficial Effects
[0037] The invention provides an aromatic amine compound. When the compound is used as a hole transport material, the hole transport rate in the device can be increased, so that the hole transport rate and the electron transport rate are balanced, so that the hole and the electron can be effectively combined in the light-emitting layer. The hole transport material with excellent performance can reduce the energy barrier in the hole injection process, so that the hole injection efficiency is improved, thereby realizing the improvement of the luminous efficiency and the extension of the service life of the device; when the compound is used as a covering layer material, the light loss reflected by the nearby electrode during light emission can be effectively reduced, thereby improving the luminous efficiency of the device and extending the service life of the device; when the compound is used as a charge generation layer material in a stacked device, each light-emitting unit can emit light independently, and the luminous efficiency is significantly improved compared with a single-layer device, and the service life is greatly extended. The preparation method of the compound is simple, the raw materials are easily available, and the industrialization needs can be met, and the compound has a good industrialization prospect. DETAILED DESCRIPTION
[0038] 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.
[0039] In the present specification, "—*" means a part connected to another substituent. "—*" can be connected to any optional position of the connected group / fragment.
[0040] 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.
[0041] 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.
[0042] For example, Can be expressed Can be expressed Can be expressed And so on.
[0043] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine and iodine.
[0044] The alkyl group described in the present invention is a monovalent group obtained by removing a hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group or a branched-chain alkyl 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, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but not limited thereto.
[0045] The cycloalkyl group described in the present invention is a monovalent group obtained 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, adamantyl, norbornyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc., but not limited thereto.
[0046] The heterocycloalkyl group of the present invention is a group formed by removing a hydrogen atom from a heterocyclic molecule whose ring atoms contain at least one heteroatom in addition to carbon atoms, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, 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, tetrahydropyrrolyl, piperidinyl, piperazinyl, oxiranyl, cyclothioranyl, propylene, morpholinyl, thiomorpholinyl, etc., but not limited thereto.
[0047] The aryl group described in the present invention is a monovalent group obtained by removing a hydrogen atom from the aromatic carbon of the aromatic compound molecule, 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, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, peryl, fluorenyl, benzofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, fluoranthenyl, etc., but not limited thereto.
[0048] The heteroaryl group described in the present invention is a group obtained by replacing one or more aromatic carbon atoms in the aromatic group with a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, 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, pyridyl, phenylpyridyl, bipyridyl, pyrrolyl, pyrimidinyl, bipyrimidinyl, triazine, quinolyl, isoquinolyl, indolyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzimidazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, and the like, but are not limited thereto.
[0049] The arylene group described in the present invention is a divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene 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, phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, pyrenyl, perylene, fluorenyl, phenylenefluorenyl, fluoranthenyl, etc., but are not limited thereto.
[0050] The heteroarylene group described in the present invention is a group formed by replacing one or more aromatic core carbons in the arylene group with heteroatoms, wherein the heteroatoms include but are not limited to oxygen, sulfur, nitrogen, silicon, selenium or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms, for example, pyridylene, bipyridylene, phenylpyridylene, pyrimidylene, bipyrimidylene, phenylpyrimidylene, triazineylene, furylene, benzofuranylene, dibenzofuranylene, thienylene, benzothienylene, dibenzothienylene, carbazolylene, benzocarbazolylene, dibenzocarbazolylene, etc., but are not limited thereto.
[0051] The fused ring group of heterocycloalkane and aromatic ring of the present invention is 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, benzopiperidinyl, naphthopiperidinyl, phenanthropiperidinyl, benzotetrahydropyrrolyl, naphthotetrahydropyrrolyl, phenanthrotetrahydropyrrolyl, benzazetidinyl, benzazepanyl, etc., but is not limited thereto.
[0052] The fused cyclic group of an alicyclic ring and an aromatic ring of the present invention is a monovalent group formed by removing a hydrogen atom after an alicyclic ring and an 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, naphthocyclopropyl, benzocyclobutyl, naphthocyclobutyl, benzocyclopentyl, naphthocyclopentyl, benzocyclohexyl, naphthocyclohexyl, benzocyclohexenyl, benzocycloheptyl, benzocycloheptenyl, benzocyclopentenyl, etc., but is not limited thereto.
[0053] The sub-fused cyclic group of the alicyclic ring and the aromatic ring of the present invention is 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, naphthocyclopropylene, benzocyclobutylene, naphthocyclobutylene, benzocyclopentylene, naphthocyclopentylene, benzocyclopentenylene, benzocyclohexylene, benzocyclohexenylene, naphthocyclohexylene, benzocycloheptylene, benzocycloheptenylene, etc., but is not limited thereto.
[0054] The fused ring group of an alicyclic ring and a heteroaromatic ring described in the present invention is 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, pyridocyclopropyl, pyrimidocyclopropyl, carbazolol, dibenzofuranocyclopropyl, dibenzothienocyclopropyl, pyridocyclobutyl, pyrimidocyclobutyl, carbazolol, dibenzofuranocyclobutyl, dibenzothienocyclobutyl, pyridocyclopentyl, pyrimidocyclopentyl, carbazolol, dibenzofuranocyclopentyl, dibenzothienocyclopentyl, pyridocyclohexyl, pyrimidocyclohexyl, carbazolol, dibenzofuranocyclohexyl, dibenzothienocyclohexyl, pyridobenzocycloheptyl, pyrimidobenzocycloheptyl, carbazolol, dibenzofuranocycloheptyl, dibenzothienocycloheptyl, and the like, but is not limited thereto.
[0055] The sub-fused cyclic group of the alicyclic ring and the heteroaromatic ring of the present invention is a divalent group formed by removing two hydrogen atoms after the alicyclic ring and the 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, pyridocyclopropyl, pyrimidocyclopropyl, dibenzofuranocyclopropyl, dibenzothiophenocyclopropyl, carbazocyclopropyl, pyridocyclobutyl, pyrimidocyclobutyl, dibenzofuranocyclobutyl, dibenzothiophenocyclobutyl, carbazocyclobutyl, pyridocyclopentyl ... The invention also includes cyclopentylene, pyrimidinylcyclopentylene, dibenzofuranylcyclopentylene, dibenzothiopheneylcyclopentylene, carbazolylcyclopentylene, pyridinylcyclohexylene, pyrimidinylcyclohexylene, dibenzofuranylcyclohexylene, dibenzothiopheneylcyclohexylene, carbazolylcyclohexylene, pyridinylcycloheptylene, pyrimidinylcycloheptylene, dibenzofuranylcycloheptylene, dibenzothiopheneylcycloheptylene, carbazolylcycloheptylene, and the like, but are not limited thereto.
[0056] 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.
[0057] 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:
[0058]
[0059] 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.
[0060] In the present invention, the term "at least one" includes one, two, three or four. The term "two or more" includes two, three, four or more, where permitted.
[0061] The present invention provides an aromatic amine compound, wherein the aromatic amine compound is selected from the structure represented by formula I:
[0062]
[0063] Wherein, Ar1 is selected from Formula II:
[0064]
[0065] The z is selected from any one of CH and N;
[0066] X1 is selected from O, S, N (R s )
[0067] The R1, R2, R a , R a '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;
[0068] The R sAny one selected from hydrogen, deuterium, tritium, 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;
[0069] 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 or 3; 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;
[0070] The a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a They are connected to each other to form a substituted or unsubstituted aromatic ring;
[0071] The Ar2 is selected from any one of the following structures:
[0072]
[0073] The v is selected from any one of CH and N;
[0074] The R p , R q , R p '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;
[0075] The R b , R cAny 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-C18 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;
[0076] The R d , R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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;
[0077] The b1 is selected from 0, 1, 2, 3 or 4; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; the c1 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 d1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R d When two or more R d The same or different from each other, or two adjacent R d are connected to each other to form a substituted or unsubstituted ring; said e1 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 are connected to each other to form a substituted or unsubstituted ring;
[0078] The Ar3 and Ar4 are independently selected from any one of the following structures:
[0079]
[0080] The x is selected from any one of CH and N;
[0081] The X2 and X3 are independently selected from O, S, N (R u )
[0082] X4 is selected from O, S, C(R i R j )、N(R w )
[0083] The R r , R r '、R i , R j R is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, or R i , R j are connected to form a substituted or unsubstituted ring;
[0084] The R u , R w Any one independently selected from hydrogen, deuterium, tritium, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring;
[0085] Said r1 is selected from 0, 1, 2, 3, 4 or 5; said r2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said r4 is selected from 0, 1, 2, 3 or 4; said r5 is selected from 0, 1 or 2; said r6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said r7 is selected from 0, 1, 2 or 3; when there are two or more R r When two or more R r The same or different from each other, or two adjacent R r They are connected to each other to form a substituted or unsubstituted aromatic ring;
[0086] The r'1 is selected from 0, 1 or 2; when there are two or more R r ', two or more R r 'same or different from each other;
[0087] The L1 is 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 group and a C6-C30 aromatic ring condensed sub-cyclic group, a substituted or unsubstituted C3-C25 alicyclic group and a C2-C30 heteroaromatic ring condensed sub-cyclic group; wherein the substituent in the "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, C1-C25 alkyl, C3-C12 cycloalkyl, C1-C25 heterocycloalkyl, and C6-C30 aryl;
[0088] The 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.
[0089] Preferably, Ar1 is selected from any one of the following groups:
[0090]
[0091] The R a , R a' is 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, phenanthrenyl , triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, Any one of dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl;
[0092] The R s 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, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrene any one of 1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-di
[0093] a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a4 is selected from 0, 1 or 2; when there are two or more R a When two or more R a The same or different from each other.
[0094] More preferably, Ar1 is selected from any one of the following groups:
[0095]
[0096]
[0097]
[0098] The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 is selected from 0, 1 or 2; the m5 is selected from 0, 1, 2, 3, 4 or 5; the m6 is selected from 0, 1, 2 or 3.
[0099] More preferably, Ar1 is selected from any one of the following groups:
[0100]
[0101]
[0102]
[0103] Preferably, Ar2 is selected from any one of the following groups:
[0104]
[0105]
[0106] The R p , R q , R p '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;
[0107] The Rb , R c 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;
[0108] The R d , R d '、R e , R e '、R i '、R j ' is 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, norbornene Any one of alkyl, 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;
[0109] The R mSelected from hydrogen, deuterium, tritium, 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, tetrahydropyrrole any one of benzophenone, benzothiazolyl, benzophenone ...
[0110] The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d4 is selected from 0, 1, 2, 3 or 4; the d5 is selected from 0, 1, 2 or 3; when there are two or more R d When two or more R d the same as or different from each other;
[0111] The d'1 is selected from 0, 1, 2, 3, 4, 5 or 6; the d'2 is selected from 0, 1, 2, 3 or 4; the d'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d'4 is selected from 0, 1 or 2; when there are two or more R d ', two or more R d 'same or different from each other;
[0112] The e1 is selected from 0, 1, 2, 3, 4 or 5; the e2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the e4 is selected from 0, 1, 2, 3 or 4; the e5 is selected from 0, 1, 2 or 3; when there are two or more R e When two or more R e the same as or different from each other;
[0113] The e'1 is selected from 0, 1, 2, 3, 4, 5 or 6; the e'2 is selected from 0, 1, 2, 3 or 4; the e'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the e'4 is selected from 0, 1 or 2; when there are two or more R e ', two or more R e ' are the same as or different from each other.
[0114] More preferably, Ar2 is selected from any one of the following groups:
[0115]
[0116]
[0117]
[0118]
[0119]
[0120] Preferably, the Any one selected from the following groups:
[0121]
[0122] Said R1 and R2 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, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, 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, indolyl, acridinyl, phenoxazinyl, phenothiazinyl;
[0123] R3, R3', R4, R4', 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, norbornane any one of 1,2-dihydropyrrolyl, ...
[0124] The R u , R w 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, tetrahydro Any one of pyrrolyl, 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;
[0125] The f1 is selected from 0, 1, 2, 3, 4 or 5; the f2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the f4 is selected from 0, 1, 2, 3 or 4; the f5 is selected from 0, 1, 2 or 3; when there are two or more R3, the two or more R3 are the same or different from each other;
[0126] The f'1 is selected from 0, 1 or 2; when there are two or more R3's, the two or more R3's are the same or different from each other;
[0127] The g1 is selected from 0, 1, 2, 3, 4 or 5; the g2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the g4 is selected from 0, 1, 2, 3 or 4; the g5 is selected from 0, 1, 2 or 3; when there are two or more R4, the two or more R4 are the same or different from each other;
[0128] The g'1 is selected from 0, 1 or 2; when two or more R4' are present, the two or more R4' are the same as or different from each other.
[0129] More preferably, the Any one selected from the following groups:
[0130]
[0131]
[0132] Preferably, L1 is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0133]
[0134] The Y is selected from any one of CH and N;
[0135] The Y a , Y b independently selected from O, S, N(R z )
[0136] The Y c , Y d independently selected from O, S, C(R x R y )、N(R z ')
[0137] The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring;
[0138] 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 C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group;
[0139] The R x , R y , R g , R vR 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 C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, or R x , R y are connected to form a substituted or unsubstituted ring;
[0140] The R z , R z 'Independently selected from any one of 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;
[0141] The substituent in the "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, C1-C25 alkyl, C3-C12 cycloalkyl, C1-C25 heterocycloalkyl, and C6-C30 aryl;
[0142] The q is selected from 1, 2, 3 or 4;
[0143] 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;
[0144] The h1' 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.
[0145] More preferably, L1 is selected from a single bond or any one of the following groups or a combination of two or more of the following groups:
[0146]
[0147] 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
[0148] The R x , R y , R g , R v 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;
[0149] The R z , R z' is independently selected from hydrogen, deuterium, tritium, 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;
[0150] wherein the substituent in the “substituted or unsubstituted” is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, benzocyclopropyl, naphthiocyclopropyl, cyclobutyl, benzocyclobutyl, naphthiocyclobutyl, cyclopentyl, benzocyclopentyl, naphthiocyclopentyl, cyclohexyl, benzocyclohexyl, naphthiocyclohexyl, cycloheptyl, benzocycloheptyl, adamantyl, norbornyl, tetrahydropyrrolyl, piperidinyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylenyl, fluorenyl and spirofluorenyl;
[0151] The h1' is selected from 0, 1 or 2; the h2' is selected from 0, 1, 2, 3 or 4; the h3' is selected from 0, 1, 2, 3, 4, 5 or 6; the h4' is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the h5' 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.
[0152] Preferably, 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:
[0153]
[0154] The E is selected from any one of CH and N;
[0155] The Y a ', Y b 'Independently selected from O, S, N (R z ”’);
[0156] The Y c ', Y d 'Independently selected from O, S, C (R x 'R y '), N(R z”);
[0157] The ring B is selected from substituted or unsubstituted C3-C10 alicyclic rings;
[0158] The R n , R n '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 C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group;
[0159] The R x '、R y '、R g '、R v ' 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 C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, or R x '、R y ' are connected to form a substituted or unsubstituted ring;
[0160] The R z ”、R z ”' is independently selected from any one of 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;
[0161] The q' is selected from 1, 2, 3 or 4;
[0162] The n1 is selected from 0, 1, 2, 3 or 4; the n2 is selected from 0, 1, 2, 3, 4, 5 or 6; the n3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the n4 is selected from 0, 1 or 2; when there are two or more R n When two or more R n The same or different from each other, or two adjacent R nare connected to each other to form a substituted or unsubstituted ring;
[0163] The n1' is selected from 0, 1 or 2; when there are two or more R n ', two or more R n ' are the same as or different from each other.
[0164] More preferably, 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:
[0165]
[0166] The R n , R n ' 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
[0167] The R x '、R y '、R g '、R v' 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, perylene, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0168] The R z ”、R z ”′ is independently 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, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl;
[0169] The n1' is selected from 0, 1 or 2; the n2' is selected from 0, 1, 2, 3 or 4; the n3' is selected from 0, 1, 2, 3, 4, 5 or 6; the n4' is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the n5' is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; when there are two or more R n ', two or more R n ' are the same as or different from each other.
[0170] 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:
[0171]
[0172]
[0173] Most preferably, the formula I is selected from any one of the following structures:
[0174]
[0175]
[0176]
[0177]
[0178]
[0179]
[0180]
[0181]
[0182]
[0183]
[0184]
[0185]
[0186]
[0187]
[0188]
[0189]
[0190]
[0191]
[0192] 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.
[0193] 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.
[0194] 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.
[0195] 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.
[0196] 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.
[0197] 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.
[0198] 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.
[0199] 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.
[0200] The anode of the present invention preferably has a material with a higher work function. It may include metals or their alloys, metal oxides, laminated materials, conductive polymers, etc. For example, aluminum (Al), silver (Ag), gold (Au), magnesium (Mg), nickel (Ni), chromium (Cr), ytterbium (Yb), indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), tin oxide (SnO2) or indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but not limited thereto.
[0201] The hole injection layer material of the present invention is preferably a material with good hole acceptance ability. In addition to the aromatic amine compound provided by the present invention, it can also include anthraquinone compounds, quinacridone compounds, porphyrin compounds, triarylamine compounds, polythiophene and its derivatives, phthalocyanine derivatives, radialene compounds and other substances with high hole injection properties, such as 2-TNATA, HATCN, F4-TCNQ, CuPC, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0202] The hole transport layer material of the present invention preferably has a good hole transport performance. In addition to the aromatic amine compound provided by the present invention, it can also include biphenyl diamine derivatives, fluorene derivatives, triarylamine derivatives, carbazole derivatives, anthraquinone compounds, quinacridone compounds, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazatriphenylene compounds, polythiophene, polyaniline, polyvinylcarbazole, etc., such as TPD, NPB, TDATA, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0203] The electron blocking layer of the present invention preferably has a material capable of blocking electrons. In addition to the aromatic amine compound provided by the present invention, aromatic amine derivatives, carbazole derivatives, etc. may also be used. Specific examples may include N, N'-di (naphthalene-1-yl) -N, N'-diphenyl-benzidine (NPD), N- (4'- (9H-carbazole-9-yl) -[1,1'-biphenyl] -4-N- ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene-2-amine, N, N-di ([1,1'-biphenyl] -4-yl) -(9H-carbazole-9-yl) -[1,1'-biphenyl] -4-amine, etc., but are not limited thereto. The aromatic amine compound of the present invention is preferred.
[0204] The light-emitting layer material of the present invention generally comprises a main material and a dopant material. The main material of the light-emitting layer may comprise naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, fluoranthene derivatives, pyrimidine derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, carbazole derivatives, pentacene derivatives, distyryl aryl derivatives, stilbene derivatives, etc., such as Alq3, BAlq, ADN, TPBI, TPD, TCTA, CBP, etc. The dopant material of the light-emitting layer may use a fluorescent light-emitting material, such as a pyrene derivative, a fluoranthene derivative, an aromatic amine derivative, etc., such as BCzVBi, DPAVBi, etc., and a phosphorescent light-emitting material may also be used, such as a metal complex such as an iridium complex, an osmium complex, a platinum complex, such as Ir(ppy)3, Ir(ppy)2(acac), FIrpic, etc., but is not limited thereto.
[0205] 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 oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, aluminum complexes, lithium complexes, beryllium complexes, phenanthroline derivatives, polymer compounds, etc., such as TPBI, BAlq, etc., but not limited thereto.
[0206] The electron transport layer material described in the present invention preferably has a material with high electron mobility, and may be a single-layer structure or a multi-layer structure, which may include oxazole derivatives, benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, imidazole derivatives, benzimidazole derivatives, carbazole derivatives, phenanthroline derivatives, aluminum complexes, lithium complexes, beryllium complexes, zinc complexes, polymer compounds, etc., such as Alq3, BAlq, PBD, BeBq2, etc., but not limited to these.
[0207] The electron injection layer material described in the present invention preferably has a material with good electron accepting ability, which may include alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties, such as Li, Ca, Yb, Tb, Sr, LiF, CsF, CaF2, BaO, Al2O3, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, MoO3, MgF2, etc., but are not limited to these.
[0208] The cathode of the present invention preferably has a material with a relatively low work function, which may include metals, metal alloys or multilayer structures, such as aluminum, silver, magnesium, magnesium-silver alloy, lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, etc., but is not limited thereto.
[0209] 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 aromatic amine compounds, aromatic hydrocarbon compounds, heteroaromatic hydrocarbon compounds, metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, etc., such as MgF2, CaF2, LiF, CsF, CsCl, CuI, V2O5, WO3, MoO3, Alq3, TiO2, ZrO, SiO2, SiN, ZnO, ZnS, etc., but not limited thereto. The aromatic amine compound of the present invention is preferred.
[0210] The P-type charge generation layer material of the present invention can be composed of metal or organic material doped with P-type. Metals include Al, Au, Cu, Fe, Pb, Zn, Pt, In, Mo, Ni and Ti, etc., which can be used alone or in alloys of two or more. In addition to the aromatic amine compounds provided by the present invention, P-type dopants may also include: F4-TCNQ, FeCl3, FeF3, SbCl5 and iodine, etc., which can be used alone or in a mixture of two or more, but are not limited thereto. The aromatic amine compounds of the present invention are preferred.
[0211] The N-type charge generation layer material of the present invention may include N-type doped organic materials such as alkali metals such as Na, Li, K, Rb, Cs, Fr, etc.; alkaline earth metals such as Ca, Ba, Be, Mg, Sr, Ra, etc.; Group 15 metals such as Bi, Sb, etc.; lanthanide metals such as La, Ce, Pr, Nd, Pm, Sm, Gd, etc.; and more than one of the above metal compounds, etc. In addition, it may also be an organic N-type dopant that has electron-donating properties and can supply at least a portion of the electronic charge to the organic host and form a charge transfer complex with the organic host, as examples thereof, there are TTF, BEDT-TTF, etc., but are not limited thereto.
[0212] 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.
[0213] [Synthetic route]
[0214] Preparation of compounds of formula I:
[0215]
[0216] Xa, Xb, and Xc are each independently selected from any one of Cl, Br, and I; the definitions of Ar1, Ar2, Ar3, Ar4, L1, L2, L3, R1, R2, a, and b are the same as those above.
[0217] Description of raw materials, reagents and characterization equipment:
[0218] 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.
[0219] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;
[0220] The elemental analysis was performed using a VarioELcube organic element analyzer from Elementar of Germany, with a sample mass of 5 to 10 mg.
[0221] [Synthesis Example 1] Synthesis of Compound 14
[0222]
[0223] Preparation of intermediate A-14:
[0224] Under nitrogen protection, toluene (300 mL), a-14 (20.01 g, 60.00 mmol), b-14 (16.39 g, 60.00 mmol), sodium tert-butoxide (11.53 g, 120.00 mmol), palladium acetate (0.20 g, 0.9 mmol) and tri-tert-butylphosphine (0.73 g, 3.60 mmol) were added to the reaction bottle in sequence, stirred and dissolved, and refluxed for 4.5 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 (8: 1) to obtain A-14 (26.18 g, yield 83%), and the solid purity was ≥ 99.87% by HPLC. Mass spectrum m / z: 525.2442 (theoretical value: 525.2457).
[0225] Preparation of compound 14:
[0226] Under nitrogen protection, toluene (250 mL), A-14 (15.77 g, 30.00 mmol), c-14 (8.34 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), tridibenzylideneacetone dipalladium (0.27 g, 0.30 mmol) and X-phos (0.29 mL, 0.60 mmol) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 7 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 over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 14 (15.83 g, yield 73%). HPLC detected the solid purity ≧99.98%. Mass spectrum m / z: 722.3246 (theoretical value: 722.3235). Theoretical element content (%) C 53 H 34 D4N2O: C, 88.06; H, 5.86; N, 3.88. Measured element content (%): C, 88.03; H, 5.84; N, 3.87.
[0227] [Synthesis Example 2] Synthesis of Compound 33
[0228]
[0229] According to the preparation method of Synthesis Example 1, a-14 was replaced by an equal molar amount of a-33, b-14 was replaced by an equal molar amount of b-33, and c-14 was replaced by an equal molar amount of c-33 to obtain compound 33 (17.23 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 808.3467 (theoretical value: 808.3454). Theoretical element content (%) C 60 H 44 N2O: C, 89.08; H, 5.48; N, 3.46. Measured element content (%): C, 89.05; H, 5.47; N, 3.48.
[0230] [Synthesis Example 3] Synthesis of Compound 47
[0231]
[0232] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-47, and c-14 was replaced by an equal mole of c-33 to obtain compound 47 (17.92 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 852.4096 (theoretical value: 852.4080). Theoretical element content (%) C 63 H 52 N2O: C, 88.70; H, 6.14; N, 3.28. Measured element content (%): C, 88.73; H, 6.15; N, 3.26.
[0233] [Synthesis Example 4] Synthesis of Compound 59
[0234]
[0235] According to the preparation method of Synthesis Example 1, a-14 was replaced by an equal molar amount of a-33, b-14 was replaced by an equal molar amount of b-59, and c-14 was replaced by an equal molar amount of c-33 to obtain compound 59 (15.96 g). The solid purity was ≥ 99.99% as determined by HPLC. Mass spectrum m / z: 718.2998 (theoretical value: 718.2984). Theoretical element content (%) C 53 H 38 N2O: C, 88.55; H, 5.33; N, 3.90. Measured element content (%): C, 88.57; H, 5.34; N, 3.92.
[0236] [Synthesis Example 5] Synthesis of Compound 75
[0237]
[0238] According to the preparation method of Synthesis Example 1, c-14 was replaced with an equal molar amount of c-75 to obtain compound 75 (16.61 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 768.3157 (theoretical value: 768.3141). Theoretical element content (%) C 57 H 40 N2O: C, 89.03; H, 5.24; N, 3.64. Measured element content (%): C, 89.06; H, 5.25; N, 3.62.
[0239] [Synthesis Example 6] Synthesis of Compound 110
[0240]
[0241] According to the preparation method of Synthesis Example 1, c-14 was replaced with an equal molar amount of c-110 to obtain compound 110 (16.84 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 768.3156 (theoretical value: 768.3141). Theoretical element content (%) C 57 H 40 N2O: C, 89.03; H, 5.24; N, 3.64. Measured element content (%): C, 89.06; H, 5.21; N, 3.65.
[0242] [Synthesis Example 7] Synthesis of Compound 145
[0243]
[0244] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-145, and c-14 was replaced by an equal mole of c-33 to obtain compound 145 (17.75 g). The solid purity was ≥ 99.95% as determined by HPLC. Mass spectrum m / z: 844.3441 (theoretical value: 844.3454). Theoretical element content (%) C 63 H 44 N2O: C, 89.54; H, 5.25; N, 3.32. Measured element content (%): C, 89.53; H, 5.27; N, 3.34.
[0245] [Synthesis Example 8] Synthesis of Compound 168
[0246]
[0247] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-33 to obtain compound 168 (17.96 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 842.3285 (theoretical value: 842.3297). Theoretical element content (%) C 63 H 42 N2O: C, 89.76; H, 5.02; N, 3.32. Measured element content (%): C, 89.77; H, 5.04; N, 3.33.
[0248] [Synthesis Example 9] Synthesis of Compound 170
[0249]
[0250] Under nitrogen protection, toluene (250 mL), a-170 (6.31 g, 30.00 mmol), b-170 (24.14 g, 60.00 mmol), sodium tert-butoxide (8.65 g, 90.00 mmol), tridibenzylideneacetone dipalladium (0.55 g, 0.60 mmol) and X-phos (0.43 mL, 0.90 mmol) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 8 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 over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from toluene to obtain compound 170 (17.66 g, yield 69%). The solid purity was ≥99.94% detected by HPLC. Mass spectrum m / z: 852.3938 (theoretical value: 852.3925). Theoretical element content (%) C 63 H 32 D 10 N2O: C, 88.70; H, 6.14; N, 3.28. Measured element content (%): C, 88.72; H, 6.15; N, 3.27.
[0251] [Synthesis Example 10] Synthesis of Compound 189
[0252]
[0253] According to the preparation method of Synthesis Example 9, b-170 was replaced with an equal molar amount of b-189 to obtain Compound 189 (17.77 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 870.3624 (theoretical value: 870.3610). Theoretical element content (%) C 65 H 46N2O: C, 89.62; H, 5.32; N, 3.22. Measured element content (%): C, 89.64; H, 5.35; N, 3.21.
[0254] [Synthesis Example 11] Synthesis of Compound 199
[0255]
[0256] According to the preparation method of Synthesis Example 9, b-170 was replaced with an equal molar amount of b-199 to obtain Compound 199 (20.82 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 1066.5816 (theoretical value: 1066.5801). Theoretical element content (%) C 79 H 74 N2O: C, 88.89; H, 6.99; N, 2.62. Measured element content (%): C, 88.86; H, 6.97; N, 2.64.
[0257] [Synthesis Example 12] Synthesis of Compound 212
[0258]
[0259] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-212 to obtain compound 212 (18.34 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 898.3936 (theoretical value: 898.3923). Theoretical element content (%) C 67 H 50 N2O: C, 89.50; H, 5.61; N, 3.12. Measured element content (%): C, 89.52; H, 5.64; N, 3.13.
[0260] [Synthesis Example 13] Synthesis of Compound 214
[0261]
[0262] According to the preparation method of Synthesis Example 9, b-170 was replaced with an equal molar amount of b-214 to obtain Compound 214 (19.55 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 986.4072 (theoretical value: 986.4088). Theoretical element content (%) C 69 H 58 N2OSi2: C, 83.93; H, 5.92; N, 2.84. Measured element content (%): C, 83.96; H, 5.93; N, 2.85.
[0263] [Synthesis Example 14] Synthesis of Compound 230
[0264]
[0265] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-230, and c-14 was replaced by an equal mole of c-230 to obtain Compound 230 (18.03 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 870.3626 (theoretical value: 870.3610). Theoretical element content (%) C 65 H 46 N2O: C, 89.62; H, 5.32; N, 3.22. Measured element content (%): C, 89.63; H, 5.34; N, 3.21.
[0266] [Synthesis Example 15] Synthesis of Compound 260
[0267]
[0268] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-260 to obtain compound 260 (18.75 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 918.3623 (theoretical value: 918.3610). Theoretical element content (%) C 69 H 46 N2O: C, 90.17; H, 5.04; N, 3.05. Measured element content (%): C, 90.16; H, 5.02; N, 3.06.
[0269] [Synthesis Example 16] Synthesis of Compound 271
[0270]
[0271] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-271 to obtain Compound 271 (18.96 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 942.3628 (theoretical value: 942.3610). Theoretical element content (%) C 71 H 46 N2O: C, 90.42; H, 4.92; N, 2.97. Measured element content (%): C, 90.43; H, 4.95; N, 2.96.
[0272] [Synthesis Example 17] Synthesis of Compound 297
[0273]
[0274] According to the preparation method of Synthesis Example 9, b-170 was replaced with an equal molar amount of b-297 to obtain Compound 297 (19.24 g). The solid purity was ≥ 99.93% as determined by HPLC. Mass spectrum m / z: 942.3624 (theoretical value: 942.3610). Theoretical element content (%) C 71 H 46 N2O: C, 90.42; H, 4.92; N, 2.97. Measured element content (%): C, 90.45; H, 4.93; N, 2.96.
[0275] [Synthesis Example 18] Synthesis of Compound 315
[0276]
[0277] According to the preparation method of Synthesis Example 9, b-170 was replaced with an equal molar amount of b-315 to obtain compound 315 (19.60 g). The solid purity was ≥ 99.91% as determined by HPLC. Mass spectrum m / z: 1004.4565 (theoretical value: 1004.4551). Theoretical element content (%) C 75 H 40 D 10 N2O: C, 89.61; H, 6.01; N, 2.79. Measured element content (%): C, 89.62; H, 6.04; N, 2.77.
[0278] [Synthesis Example 19] Synthesis of Compound 376
[0279]
[0280] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-376, and c-14 was replaced by an equal mole of c-376 to obtain compound 376 (16.49 g). The solid purity was ≥ 99.98% as determined by HPLC. Mass spectrum m / z: 752.2678 (theoretical value: 752.2661). Theoretical element content (%) C 53 H 37 FN2S: C, 84.55; H, 4.95; N, 3.72. Measured element content (%): C, 84.56; H, 4.92; N, 3.73.
[0281] [Synthesis Example 20] Synthesis of Compound 385
[0282]
[0283] According to the preparation method of Synthesis Example 1, c-14 was replaced with an equal molar amount of c-385 to obtain compound 385 (17.28 g). The solid purity was ≥ 99.96% as determined by HPLC. Mass spectrum m / z: 810.3053 (theoretical value: 810.3069). Theoretical element content (%) C 59 H 42 N2S: C, 87.37; H, 5.22; N, 3.45. Measured element content (%): C, 87.36; H, 5.24; N, 3.48.
[0284] [Synthesis Example 21] Synthesis of Compound 399
[0285]
[0286] According to the preparation method of Synthesis Example 1, a-14 was replaced by an equal molar amount of a-33, b-14 was replaced by an equal molar amount of b-399, and c-14 was replaced by an equal molar amount of c-376 to obtain compound 399 (17.03 g). The solid purity was ≥ 99.95% by HPLC. Mass spectrum m / z: 810.3057 (theoretical value: 810.3069). Theoretical element content (%) C 59 H 42 N2S: C, 87.37; H, 5.22; N, 3.45. Measured element content (%): C, 87.38; H, 5.25; N, 3.44.
[0287] [Synthesis Example 22] Synthesis of Compound 416
[0288]
[0289] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-416 to obtain compound 416 (16.91 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 782.2742 (theoretical value: 782.2756). Theoretical element content (%) C 57 H 38 N2S: C, 87.44; H, 4.89; N, 3.58. Measured element content (%): C, 87.45; H, 4.87; N, 3.56.
[0290] [Synthesis Example 23] Synthesis of Compound 476
[0291]
[0292] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-476 to obtain compound 476 (17.80 g). The solid purity was ≥ 99.94% as determined by HPLC. Mass spectrum m / z: 859.3036 (theoretical value: 859.3021). Theoretical element content (%) C 62 H 41 N3S: C, 86.58; H, 4.81; N, 4.89. Measured element content (%): C, 86.56; H, 4.82; N, 4.87.
[0293] [Synthesis Example 24] Synthesis of Compound 578
[0294]
[0295] According to the preparation method of Synthesis Example 1, b-14 was replaced by an equal mole of b-168, and c-14 was replaced by an equal mole of c-578 to obtain compound 578 (18.47 g). The solid purity was ≥ 99.92% as determined by HPLC. Mass spectrum m / z: 918.3736 (theoretical value: 918.3722). Theoretical element content (%) C 68 H 46 N4: C, 88.86; H, 5.04; N, 6.10. Measured element content (%): C, 88.83; H, 5.05; N, 6.14.
[0296] [Synthesis Example 25] Synthesis of Compound 589
[0297]
[0298] According to the preparation method of Synthesis Example 1, c-14 was replaced with an equal molar amount of c-589 to obtain compound 589 (17.15 g). The solid purity was ≥ 99.97% as determined by HPLC. Mass spectrum m / z: 793.345768 (theoretical value: 793.3457). Theoretical element content (%) C 59 H 43 N3: C, 89.25; H, 5.46; N, 5.29. Measured element content (%): C, 89.26; H, 5.43; N, 5.27.
[0299] [Device Example]
[0300] 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.
[0301] [Example 1]
[0302] The glass substrate was cleaned with distilled water and ultrasonic waves. After the distilled water cleaning, ultrasonic cleaning 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 cleaning, the substrate was transferred to an evaporator. ITO / Ag / 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 14 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 7wt% of GD-1 to form a layer with a thickness of ET-1 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 Mg:Ag (mass ratio 1:9) was evaporated on the electron injection layer to form a layer with a thickness of CP-1 is evaporated on the cathode layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0303]
[0304] [Examples 2 to 25]
[0305] Compound 33, compound 47, compound 59, compound 75, compound 110, compound 145, compound 168, compound 170, compound 189, compound 199, compound 212, compound 214, compound 230, compound 260, compound 271, compound 297, compound 315, compound 376, compound 385, compound 399, compound 416, compound 476, compound 578, and compound 589 of the present invention were used to replace compound 14 in Example 1 as hole transport layer materials, except that an organic electroluminescent device was prepared by the same preparation method as Example 1.
[0306] [Comparative Examples 1 to 3]
[0307] 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 14 in Example 1 as hole transport layer materials.
[0308] 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.
[0309] Table 1:
[0310]
[0311]
[0312] 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, the device has higher luminous efficiency and longer service life than the comparative compounds P-1 to P-3. The compound of the present invention is a hole transport layer material with good performance.
[0313] [Example 26]
[0314] 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. The compound 14 of the present invention is evaporated 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: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.
[0315]
[0316] [Examples 27 to 50]
[0317] Compound 33, compound 47, compound 59, compound 75, compound 110, compound 145, compound 168, compound 170, compound 189, compound 199, compound 212, compound 214, compound 230, compound 260, compound 271, compound 297, compound 315, compound 376, compound 385, compound 399, compound 416, compound 476, compound 578, and compound 589 of the present invention were used to replace compound 14 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.
[0318] [Comparative Examples 4 to 5]
[0319] 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 14 in Example 26 as the second hole transport layer material.
[0320] 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 of the present invention 26-50 and comparative embodiments 4-5 are shown in Table 2 below.
[0321] Table 2:
[0322]
[0323]
[0324] 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.
[0325] [Example 51]
[0326] 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 compound 14 is evaporated on the cathode layer to form a layer with a thickness of Thus, an organic light-emitting device is formed.
[0327]
[0328]
[0329] [Examples 52 to 75]
[0330] Compound 33, compound 47, compound 59, compound 75, compound 110, compound 145, compound 168, compound 170, compound 189, compound 199, compound 212, compound 214, compound 230, compound 260, compound 271, compound 297, compound 315, compound 376, compound 385, compound 399, compound 416, compound 476, compound 578, and compound 589 of the present invention were used to replace compound 14 in Example 51 as covering layer materials. Except for this, an organic electroluminescent device was prepared by the same preparation method as Example 51.
[0331] [Comparative Examples 6 to 7]
[0332] 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 14 in Device Example 51 as the covering layer material.
[0333] 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.
[0334] Table 3:
[0335]
[0336]
[0337] 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.
[0338] 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 Formula II: The z is selected from any one of CH and N; X1 is selected from O, S, N (R s ) The R1, R2, R a , R a '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 s Any one selected from hydrogen, deuterium, tritium, 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 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 or 3; 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 a1 is selected from 0, 1, 2, 3 or 4; when there are two or more R a When two or more R a The same or different from each other, or two adjacent R a They are connected to each other to form a substituted or unsubstituted aromatic ring; The Ar2 is selected from any one of the following structures: The v is selected from any one of CH and N; The R p , R q , R p '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; The R b , R c 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-C18 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 R d , R e Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, 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 b1 is selected from 0, 1, 2, 3 or 4; when there are two or more R b When two or more R b The same or different from each other, or two adjacent R b are connected to each other to form a substituted or unsubstituted ring; the c1 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 d1 is selected from 0, 1, 2, 3, 4 or 5; when there are two or more R d When two or more R d The same or different from each other, or two adjacent R d are connected to each other to form a substituted or unsubstituted ring; said e1 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 are connected to each other to form a substituted or unsubstituted ring; The Ar3 and Ar4 are independently selected from any one of the following structures: The x is selected from any one of CH and N; The X2 and X3 are independently selected from O, S, N (R u ) X4 is selected from O, S, C(R i R j )、N(R w ) The R r , R r '、R i , R j R is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring, or R i , R j are connected to form a substituted or unsubstituted ring; The R u , R w Any one independently selected from hydrogen, deuterium, tritium, 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, a fused ring group of a substituted or unsubstituted C3-C30 alicyclic and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C1-C25 heterocycloalkane and a C6-C30 aromatic ring, a fused ring group of a substituted or unsubstituted C3-C25 alicyclic and a C2-C30 heteroaromatic ring; Said r1 is selected from 0, 1, 2, 3, 4 or 5; said r2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said r3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said r4 is selected from 0, 1, 2, 3 or 4; said r5 is selected from 0, 1 or 2; said r6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; said r7 is selected from 0, 1, 2 or 3; when there are two or more R r When two or more R r The same or different from each other, or two adjacent R r They are connected to each other to form a substituted or unsubstituted aromatic ring; The r'1 is selected from 0, 1 or 2; when there are two or more R r ', two or more R r 'same or different from each other; The L1 is 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 group and a C6-C30 aromatic ring condensed sub-group, a substituted or unsubstituted C3-C25 alicyclic group and a C2-C30 heteroaromatic ring condensed sub-group; wherein the substituent in the "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, C1-C25 alkyl, C3-C12 cycloalkyl, C1-C25 heterocycloalkyl, and C6-C30 aryl; The 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 R a , R a ' is 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, phenanthrenyl , triphenylene, pyrenyl, peryl, fluorenyl, spirofluorenyl, fluoranthenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, benzocarbazolyl, pyrrolyl, oxazolyl, benzoxazolyl, Any one of dibenzoxazolyl, thiazolyl, benzothiazolyl, dibenzothiazolyl, imidazolyl, benzimidazolyl, dibenzimidazolyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, acridinyl, phenoxazinyl, and phenothiazinyl; The R s 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, tetrahydropyrrolyl, piperidinyl, benzocyclopropyl, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrene any one of 1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-dibenzo-1,2-di a1 is selected from 0, 1, 2, 3 or 4; a2 is selected from 0, 1, 2, 3, 4, 5 or 6; a3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; a4 is selected from 0, 1 or 2; when there are two or more R a When two or more R a The same or different from each other.
3. An aromatic amine compound according to claim 1, characterized in that: The Ar1 is selected from any one of the following groups: The m1 is selected from 0, 1, 2, 3 or 4; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the m4 is selected from 0, 1 or 2; the m5 is selected from 0, 1, 2, 3, 4 or 5; the m6 is selected from 0, 1, 2 or 3.
4. An aromatic amine compound according to claim 1, characterized in that: The Ar2 is selected from any one of the following groups: The R p , R q , R p '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; The R b , R c 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 d , R d '、R e , R e '、R i '、R j ' is 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, norbornene Any one of alkyl, 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 R m Selected from hydrogen, deuterium, tritium, 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, tetrahydropyrrole any one of benzophenone, benzothiazolyl, benzophenone ... The d1 is selected from 0, 1, 2, 3, 4 or 5; the d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the d4 is selected from 0, 1, 2, 3 or 4; the d5 is selected from 0, 1, 2 or 3; when there are two or more R d When two or more R d the same as or different from each other; The d'1 is selected from 0, 1, 2, 3, 4, 5 or 6; the d'2 is selected from 0, 1, 2, 3 or 4; the d'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the d'4 is selected from 0, 1 or 2; when there are two or more R d ', two or more R d 'same or different from each other; The e1 is selected from 0, 1, 2, 3, 4 or 5; the e2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the e3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the e4 is selected from 0, 1, 2, 3 or 4; the e5 is selected from 0, 1, 2 or 3; when there are two or more R e When two or more R e the same as or different from each other; The e'1 is selected from 0, 1, 2, 3, 4, 5 or 6; the e'2 is selected from 0, 1, 2, 3 or 4; the e'3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the e'4 is selected from 0, 1 or 2; when there are two or more R e ', two or more R e ' 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: Said R1 and R2 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, naphthoxycyclopropyl, benzocyclobutyl, naphthoxycyclobutyl, benzocyclopentyl, naphthoxycyclopentyl, benzocyclohexyl, naphthoxycyclohexyl, benzocycloheptyl, phenyl, biphenyl, terphenyl, 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, indolyl, acridinyl, phenoxazinyl, phenothiazinyl; R3, R3', R4, R4', 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, norbornane any one of 1,2-dihydropyrrolyl, ... The R u , R w 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, tetrahydro Any one of pyrrolyl, 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 f1 is selected from 0, 1, 2, 3, 4 or 5; the f2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the f3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the f4 is selected from 0, 1, 2, 3 or 4; the f5 is selected from 0, 1, 2 or 3; when there are two or more R3, the two or more R3 are the same or different from each other; The f'1 is selected from 0, 1 or 2; when there are two or more R3's, the two or more R3's are the same or different from each other; The g1 is selected from 0, 1, 2, 3, 4 or 5; the g2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the g3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the g4 is selected from 0, 1, 2, 3 or 4; the g5 is selected from 0, 1, 2 or 3; when there are two or more R4, the two or more R4 are the same or different from each other; The g'1 is selected from 0, 1 or 2; when two or more R4' are present, the two or more R4' are the same as or different from each other.
6. An aromatic amine compound according to claim 1, characterized in that: The L1 is selected from a single bond or any one of the following groups or a combination of two or more of the following groups: The Y is selected from any one of CH and N; The Y a , Y b independently selected from O, S, N(R z ) The Y c , Y d independently selected from O, S, C(R x R y )、N(R z ') The ring A is selected from a substituted or unsubstituted C3-C10 alicyclic ring; 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 C3-C30 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring group; The R x , R y , R g , R v R 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 C3-C30 alicyclic and C6-C30 aromatic fused ring, substituted or unsubstituted C1-C25 heterocycloalkane and C6-C30 aromatic fused ring, or R x , R y are connected to form a substituted or unsubstituted ring; The R z , R z 'Independently selected from any one of 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; The substituent in the "substituted or unsubstituted" is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, C1-C25 alkyl, C3-C12 cycloalkyl, C1-C25 heterocycloalkyl, and C6-C30 aryl; The q 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 h1' 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, wherein: The organic layer comprises at least one of a hole transport layer and a charge generation layer, and the at least one of the hole transport layer and the charge generation 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 on a side of the cathode away from the anode, wherein: The organic layer includes a covering layer, and the covering layer includes at least one of the aromatic amine compounds according to any one of claims 1 to 7.