A triamine compound and an organic electroluminescent device thereof

Abstract

The present invention provides a triamine compound and an organic electroluminescent device thereof, relating to the technical field of organic electroluminescent materials. The triamine compound of the present invention has good hole mobility and a suitable HOMO energy level. When used as a hole transport material in an organic electroluminescent device, it can not only improve the injection and transport efficiency of holes in the device, reduce the driving voltage of the device, and improve the luminous efficiency of the device, but also reduce the movement of excitons to the outside of the light-emitting layer, reduce the loss of the device, and extend the service life of the device. In addition, the triamine compound of the present invention has good film-forming property and stability, and is also an excellent capping layer material.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent materials, and particularly relates to a triamine compound and an organic electroluminescent device thereof. Background Art

[0002] An organic light emitting diode (OLED) is a technology that directly converts electrical energy into light energy by using organic semiconductor functional materials. Its light emitting principle is that under the drive of an applied voltage, electrons and holes are generated from the cathode and anode respectively. The electrons and holes are transported in the organic layer, and the two recombine in the light emitting layer to generate excitons. The excitons undergo radiative transitions back to the ground state and emit light. Since OLEDs have the advantages of being all-solid-state, having a wide range of material selection, low working temperature, high luminous efficiency, high color contrast, fast response speed, being thin and light, wide viewing angle, low power consumption, and being able to achieve flexible display, etc., they have become a research hotspot in recent years and have good commercial and market prospects.

[0003] With the development of organic electroluminescent devices, the structure of electroluminescent devices is also constantly being improved. From the earliest single-layer device structure to the double-layer device structure, and then to the multi-layer device structure, the performance of organic electroluminescent devices is improved by continuously improving the structure of organic electroluminescent devices. Nowadays, a sandwich structure of a sandwich type is mostly adopted, that is, an organic functional layer is provided between the cathode and anode on both sides of the device. The organic functional layer can include a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cover layer, etc. Since organic electroluminescent devices have a unique device structure, the research on materials for each functional layer is also crucial.

[0004] The materials used in organic electroluminescent devices mainly include electron injection materials, electron transport materials, hole blocking materials, luminescent materials, electron blocking materials, hole transport materials, hole injection materials, etc. Among them, in terms of hole transport materials, the main function is to improve the injection and transport balance of device holes and improve the performance of organic electroluminescent devices. Hole transport materials need to have the following properties: very high hole mobility, to ensure good hole transport performance, and improve the luminous efficiency of the device; good film forming properties and good thermal stability, to extend the service life of the device; with a suitable HOMO orbital energy level, to reduce the driving voltage and ensure the effective injection and transmission of holes in the device. However, the hole transport materials currently studied still have problems such as poor hole mobility, low thermal stability, poor film forming properties and energy level mismatch, which leads to problems such as increased driving voltage, reduced luminous efficiency and shortened service life of organic electroluminescent devices. Secondly, in terms of covering layer materials, covering layer materials can improve the light coupling efficiency of the device, improve the light output mode, and enable the light originally confined inside the device to be emitted from the device, showing a higher light extraction efficiency. The covering layer materials currently used still have problems such as low light extraction efficiency and low absorption of ultraviolet light from the external environment, which need to be further improved.

[0005] In order to further improve the performance of organic electroluminescent devices and improve the existing problems of organic electroluminescent devices, it is necessary to develop organic electroluminescent materials with better performance, among which hole transport materials and covering layer materials are particularly important. Summary of the invention

[0006] In view of the problems existing in the prior art, the present invention provides a triamine compound and an organic electroluminescent device thereof.

[0007] The present invention provides a triamine compound represented by the following formula 1:

[0008]

[0009] Wherein, the Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 are the same or different and are selected from a substituted or unsubstituted C6-C60 aromatic group, a substituted or unsubstituted C2-C60 heteroaromatic group, a substituted or unsubstituted C3-C25 alicyclic ring and a C6-C30 aromatic ring fused ring group, a substituted or unsubstituted C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring fused ring group;

[0010] At least one of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 is selected from the group shown in the following formula 1-a,

[0011]

[0012] The "*" represents a connection site with L1, L2, L3, L4, L5 or L6;

[0013] The z is the same or different and is selected from CH or N;

[0014] The X is selected from O, S or NR b ;

[0015] The R b is selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0016] The R4 is the same or different and is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 alicyclic and C6-C30 aromatic fused ring group, substituted or unsubstituted C3-C25 alicyclic and C2-C30 heteroaromatic fused ring group, or two adjacent R4s are bonded to each other to form a substituted or unsubstituted ring;

[0017] The n1 is selected from 0, 1, 2, 3, 4 or 5;

[0018] And at least one of the Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 is selected from the group shown in Formula 1-b below,

[0019]

[0020] The Y is selected from O, S, CR x R y or NR z ;

[0021] The R x , R y are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or adjacent Rs x , R y are bonded to each other to form a substituted or unsubstituted ring, or the carbon atoms corresponding to R x , R y are connection sites with L1, L2, L3, L4, L5, L6;

[0022] The R z is selected from one of a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted silyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, or R z The corresponding nitrogen atom is the site connected to L1, L2, L3, L4, L5, and L6;

[0023] The R5 and R6 are the same or different and are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted silyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C2-C30 heteroaryl, a substituted or unsubstituted fused ring group of a C3-C25 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring, or two adjacent R5s and two adjacent R6s are bonded to each other to form a substituted or unsubstituted ring;

[0024] The m1 is selected from 0, 1, 2, 3, or 4; the m2 is selected from 0, 1, 2, 3, or 4;

[0025] The R1, R2, and R3 are the same or different and are each independently selected from hydrogen, deuterium, tritium, cyano, nitro, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted silyl, a substituted or unsubstituted C3-C30 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C2-C60 heteroaryl;

[0026] The L1, L2, L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted fused arylene group of a C3-C25 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused arylene group of a C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring.

[0027] In addition, the present invention also provides an organic electroluminescent device, and the organic electroluminescent device contains the triamine compound of the present invention described above.

[0028] Beneficial effects: The triamine compound of Formula 1 of the present invention has good hole mobility and appropriate HOMO energy level. As a hole transport material for organic light-emitting devices, it can not only effectively reduce the hole transport resistance, improve the injection and transport efficiency of holes in the device, reduce the driving voltage of the device, and improve the light-emitting efficiency of the device; but also reduce the movement of excitons to the outside of the light-emitting layer, avoid interface luminescence, reduce the loss of the device, and extend the service life of the device.

[0029] In addition, the triamine compound of Formula 1 of the present invention contains benzofuran / benzothiophene groups, which is beneficial to film formation of the molecule and increases the glass transition temperature of the compound. When the triamine compound of the present invention is used as a covering layer material in an organic light-emitting device, it can effectively reduce the total reflection loss and waveguide loss in the device, reduce the driving voltage of the device, improve the light-emitting efficiency of the device, and extend the service life of the device. Specific embodiments

[0030] The following further illustrates the present invention in conjunction with specific embodiments. It should be understood that these embodiments are only used to illustrate the present invention and not to limit the scope of the present invention. After reading the present invention, various equivalent modifications of the present invention by those skilled in the art fall within the scope claimed in this application.

[0031] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural and non-natural isotope abundances.

[0032] The halogen described in the present invention includes fluorine, chlorine, bromine, and iodine.

[0033] In the present invention, the "unsubstituted ZZ group" in the "substituted or unsubstituted ZZ group" means that the hydrogen atom of the "ZZ group" is not replaced by a substituent. For example, in the "substituted or unsubstituted aryl group having 6 to 60 carbon atoms", the "unsubstituted aryl group" means that the hydrogen atom of the "aryl group" is not replaced by a substituent. And so on.

[0034] In the present invention, "CXX-CYY of the ZZ group, which may be substituted or unsubstituted" means the number of carbon atoms in the unsubstituted "ZZ group". When the "ZZ group" has substituents, it does not include the carbon atoms of the substituents. For example, in "aryl of C6-C60, which may be substituted or unsubstituted", "C6-C60" represents the number of carbon atoms in the unsubstituted "aryl". When the "aryl" has substituents, it does not include the carbon atoms of the substituents. In "fused ring group of alicyclic ring of C3-C25 and aromatic ring of C6-C30, which may be substituted or unsubstituted", "C3-C25" represents the number of carbon atoms in the unsubstituted "alicyclic ring". When the "alicyclic ring" has substituents, it does not include the carbon atoms of the substituents; "C6-C30" represents the number of carbon atoms in the unsubstituted "aromatic ring". When the "aromatic ring" has substituents, it does not include the carbon atoms of the substituents. And so on.

[0035] In the present invention, when the position of the substituent on the ring is not fixed, it means that it can be connected to any of the corresponding optional sites of the ring.

[0036] For example, may represent may represent may represent And so on.

[0037] In this specification, when the bond where the substituent or the connection site is located passes 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, may represent may represent And so on.

[0038] In the present invention, "adjacent two groups are bonded to form a ring" means that adjacent groups combine with each other and are optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocyclic ring can include an aliphatic heterocyclic ring or an aromatic heterocyclic ring. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocyclic ring can be a saturated aliphatic heterocyclic ring or an unsaturated aliphatic heterocyclic ring. The hydrocarbon ring and the heterocyclic ring can be a monocyclic or polycyclic group. Examples are as follows:

[0039]

[0040] In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. Examples are as follows:

[0041]

[0042] In the present invention, the formed ring can be a three-membered ring, four-membered ring, five-membered ring, six-membered ring, seven-membered ring, eight-membered ring, fused ring, spiro ring, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited thereto.

[0043] "Substituted" in the "substituted or unsubstituted" described in the present invention means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogens are replaced by multiple substituents, the multiple substituents can be the same or different. The position of the hydrogen replaced by the substituent can be any position. The substituents represented by "substituted" in the above "substituted or unsubstituted" include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted silyl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted C6-C20 aryloxy, substituted or unsubstituted C2-C15 heterocyclic group, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C20 heteroaryl, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C6-C20 aromatic ring, substituted or unsubstituted fused ring group of C3-C15 alicyclic ring and C2-C20 heteroaromatic ring, etc. Preferred are the following groups: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, camphenyl, isocamphenyl, fenchyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylenyl, anthryl, pyrenyl, fluorenyl, fluoranthenyl, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indenyl, dihydronaphthyl, fluorene, spirobifluorene, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, benzodioxolyl, benzodithioyl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc. In addition, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can be bonded to form a ring.

[0044] The alkyl group in the present invention refers to the hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. The alkyl group can be a straight-chain alkyl group or a branched-chain alkyl group. When the number of carbon atoms in the chain-like alkyl group in the present invention is three or more, its isomers are included. For example, propyl includes n-propyl and isopropyl; butyl includes n-butyl, isobutyl, sec-butyl, tert-butyl, and so on. Examples of the alkyl group include, but are not limited to, the groups described below, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto. The number of carbon atoms in the alkyl group is C1-C30, preferably C1-C25, preferably C1-C20, preferably C1-C15, and more preferably C1-C10.

[0045] The silyl group in the present invention refers to the -Si(R k )3 group, where each R k is the same or different and is selected from the groups described below: hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C1-C30 alkenyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or unsubstituted C2-C60 heteroaryl group, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C6-C60 aromatic ring, substituted or unsubstituted fused ring group of C3-C30 alicyclic ring and C2-C60 heteroaryl ring. Preferably, each R k is the same or different and is selected from the groups described below: hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C3-C30 cycloalkyl group. The number of carbon atoms in the alkyl group is preferably C1-C20, preferably C1-C15, and more preferably C1-C10, and most preferably C1-C8. The number of carbon atoms in the cycloalkyl group is preferably C3-C20, preferably C3-C15, and more preferably C3-C10, and most preferably C3-C7. Preferably, each R k is the same or different and is selected from the groups described below: hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferred substituted silyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0046] The cycloalkyl group described in the present invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group includes monocyclic cycloalkyl groups, polycyclic cycloalkyl groups, and bridged cycloalkyl groups. Examples of the cycloalkyl group include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, camphenyl, fenchyl, isocamphenyl, etc., but are not limited thereto. The number of carbon atoms in the cycloalkyl group is C3-C30, preferably C3-C25, more preferably C3-C20, still more preferably C3-C15, and even more preferably C3-C10.

[0047] The aryl group described in the present invention refers to the general name of a monovalent group remaining after removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused-ring aryl groups, or combinations thereof. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl, triphenylene, fluorenyl, benzofluorenyl, spirobifluorenyl, spiroanthracenofluorenyl, pyrenyl, -yl, fluoranthenyl, etc., but are not limited thereto. The number of carbon atoms in the aryl group is C6-C60, preferably C6-C30, more preferably C6-C25, and still more preferably C6-C20.

[0048] The heteroaryl group described in the present invention refers to a monovalent group in which at least one carbon atom in the aryl group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Examples of the heteroaryl group include, but are not limited to, the following groups: benzofuranyl, naphthofuranyl, phenanthrofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiophenyl, naphthothiophenyl, phenanthrothiophenyl, dibenzothiophenyl, benzodibenzothiophenyl, indolyl, naphthylindolyl, carbazolyl, benzocarbazolyl, spirofluoreneoxanthenyl, spirofluorenesulfuranthenyl, spirofluoreneazaanthenyl, spirofluorenesiloxanthenyl, benzodioxolyl, benzodithioetheryl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroisobenzothiophenyl, phenoxazinyl, phenothiazinyl, dihydroacridinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, etc., but are not limited thereto. The number of carbon atoms in the heteroaryl group can be C2-C60, preferably C2-C30, more preferably C2-C25, and still more preferably C3-C20.

[0049] The fused ring group of alicyclic and aromatic rings in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom from the fused alicyclic and aromatic rings. Examples of the fused ring group of alicyclic and aromatic rings include, but are not limited to, the following groups: benzocyclopropyl, benzocyclobutyl, benzocyclobutenyl, indanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptyl, benzocycloheptenyl, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3 - C25, preferably C3 - C20, more preferably C3 - C15, still more preferably C3 - C10, and even more preferably C3 - C8. The number of carbon atoms in the aromatic ring is C6 - C30, preferably C6 - C25, more preferably C6 - C18, still more preferably C6 - C12, and even more preferably C6 - C10.

[0050] The fused ring group of alicyclic and heteroaromatic rings in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom from the fused alicyclic and heteroaromatic rings. Examples of the fused ring group of alicyclic and heteroaromatic rings include, but are not limited to, the following groups: pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinocyclopentenyl, pyridinocyclohexenyl, pyrimidinocyclopentyl, pyrimidinocyclohexyl, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3 - C25, preferably C3 - C20, more preferably C3 - C15, still more preferably C3 - C10. The number of carbon atoms in the heteroaromatic ring is C2 - C30, preferably C2 - C25, more preferably C2 - C18, still more preferably C2 - C12, and even more preferably C2 - C10.

[0051] The arylene group in the present invention refers to the general name of the monovalent group remaining after removing one hydrogen atom from the aromatic nucleus carbon of an aromatic compound molecule. The arylene group includes monocyclic arylene, polycyclic arylene, fused ring arylene or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylenyl, naphthylene, phenanthrylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, naphthofluorenylene, spirobifluorenylene, etc., but are not limited thereto. The number of carbon atoms in the arylene group is C6 - C30, preferably C6 - C25, more preferably C6 - C20, and even more preferably C6 - C18.

[0052] The heteroarylene group in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. The heteroarylene group includes monocyclic heteroarylene, polycyclic heteroarylene, fused ring heteroarylene or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the following groups: pyridylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, quinazolinylene, naphthyridinylene, etc., but are not limited thereto. The number of carbon atoms in the heteroarylene group is C2 - C30, preferably C2 - C25, more preferably C2 - C20.

[0053] The sub-fused ring group of an alicyclic ring and an aromatic ring in the present invention refers to the general name of a divalent group remaining after removing two hydrogen atoms when the alicyclic ring and the aromatic ring are fused together. Examples of the sub-fused ring group of the alicyclic ring and the aromatic ring include, but are not limited to, the following groups: benzocyclopropylidene, benzocyclobutylidene, indanyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocycloheptylidene, benzocyclobutenylidene, benzocycloheptenylidene, naphthocyclopentylidene, naphthocyclohexylidene, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3 - C25, preferably C3 - C20, more preferably C3 - C15, and still more preferably C3 - C8. The number of carbon atoms in the aromatic ring is C6 - C30, preferably C6 - C20, more preferably C6 - C18, and preferably C6 - C10.

[0054] The sub-fused ring group of an alicyclic ring and a heteroaromatic ring in the present invention refers to the general name of a divalent group remaining after removing two hydrogen atoms when the alicyclic ring and the heteroaromatic ring are fused together. Examples of the sub-fused ring group of the alicyclic ring and the heteroaromatic ring include, but are not limited to, the following groups: pyridinocyclobutylidene, pyridinocyclopentylidene, pyridinocyclohexylidene, pyridinocyclopentenylidene, etc., but are not limited thereto. The number of carbon atoms in the alicyclic ring is C3 - C25, preferably C3 - C20, more preferably C3 - C15, and still more preferably C3 - C8. The number of carbon atoms in the heteroaromatic ring is C2 - C30, preferably C2 - C20, more preferably C2 - C18, and preferably C2 - C10.

[0055] The present invention provides a triamine compound represented by the following formula 1,

[0056]

[0057] wherein, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 - 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 - 60 carbon atoms, a sub-fused ring group of an alicyclic ring having 3 - 25 carbon atoms and an aromatic ring having 6 - 30 carbon atoms, and a sub-fused ring group of an alicyclic ring having 3 - 25 carbon atoms and a heteroaromatic ring having 2 - 30 carbon atoms;

[0058] At least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group represented by the following formula 1-a,

[0059]

[0060] The "*" represents the connection site with L1, L2, L3, L4, L5, or L6;

[0061] z is the same or different and is each independently selected from CH or N;

[0062] X is selected from O, S or NR b ;

[0063] R b is selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;

[0064] R4s, which may be the same or different, are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C25 fused cycloalkyl-aryl group, and substituted or unsubstituted C3-C25 fused cycloalkyl-heteroaryl group, or two adjacent R4s are bonded to each other to form a substituted or unsubstituted ring;

[0065] n1 is selected from 0, 1, 2, 3, 4 or 5;

[0066] and at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 is selected from the group shown in Formula 1-b below,

[0067]

[0068] Y is selected from O, S, CR x R y or NR z ;

[0069] R x 、R y , which may be the same or different, are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rs x 、R y are bonded to each other to form a substituted or unsubstituted ring, or the carbon atoms corresponding to Rs x 、R y are the bonding sites connected to L1, L2, L3, L4, L5, L6;

[0070] R zSelected from a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or R z The corresponding nitrogen atom is the site connected to L1, L2, L3, L4, L5, and L6;

[0071] Said R5 and R6 are the same or different and are selected from hydrogen, deuterium, tritium, cyano group, halogen, nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted fused ring group of a C3-C25 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused ring group of a C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring, or two adjacent R5s and two adjacent R6s are bonded to each other to form a substituted or unsubstituted ring;

[0072] Said m1 is selected from 0, 1, 2, 3, or 4; said m2 is selected from 0, 1, 2, 3, or 4;

[0073] Said R1, R2, and R3 are the same or different and are selected from hydrogen, deuterium, tritium, cyano group, nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group;

[0074] Said L1, L2, L3, L4, L5, and L6 are the same or different and are selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C2-C30 heteroarylene group, a substituted or unsubstituted fused arylene group of a C3-C25 alicyclic ring and a C6-C30 aromatic ring, a substituted or unsubstituted fused arylene group of a C3-C25 alicyclic ring and a C2-C30 heteroaromatic ring.

[0075] Preferably, said triamine compound is selected from one of Formula 1-1 to Formula 1-3,

[0076]

[0077] Preferably, at least one of Ar1 to Ar6 is selected from the group represented by Formula 1-a, including: one of Ar1 to Ar6 is selected from this group. Specifically, Ar1, Ar2, Ar3, Ar4, Ar5, or Ar6 is selected from this group; two of Ar1 to Ar6 are selected from this group. Specifically, Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar5, Ar3 and Ar4, Ar3 and Ar5, Ar5 and Ar6 are selected from this group; three of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2, and Ar3, Ar1, Ar2, and Ar5, Ar1, Ar3, and Ar4, Ar1, Ar3, and Ar5, Ar1, Ar5, and Ar6, Ar3, Ar4, and Ar5, Ar3, Ar5, and Ar6 are selected from this group; four of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2, Ar3, and Ar4, Ar1, Ar2, Ar3, and Ar5, Ar1, Ar2, Ar5, and Ar6, Ar1, Ar3, Ar4, and Ar5, Ar1, Ar3, Ar5, and Ar6, Ar3, Ar4, Ar5, and Ar6 are selected from this group; five of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2, Ar3, Ar4, and Ar5, Ar1, Ar2, Ar3, Ar5, and Ar6 are selected from this group.

[0078] Preferably, the Formula 1-a is selected from one of the following groups:

[0079]

[0080]

[0081] n1 is selected from 0, 1, 2, 3, 4, or 5; n2 is selected from 0, 1, 2, 3, or 4; n3 is selected from 0, 1, 2, or 3; n4 is selected from 0, 1, or 2; n5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; n6 is selected from 0, 1, 2, 3, 4, 5, or 6; n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; n9 is selected from 0 or 1.

[0082] More preferably, the Formula 1-a is selected from one of the following groups:

[0083]

[0084] Preferably, the R bSelected from methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, benzocyclobutenyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, methylfluorenyl, phenylfluorenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and one of them can be substituted by one or more deuteriums.

[0085] Preferably, the R4s are the same or different and are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted methylfluorenyl, substituted or unsubstituted phenylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof, or two adjacent R4s are bonded to each other to form a substituted or unsubstituted benzene ring.

[0086] More preferably, R4 is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, silyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and one of the above groups may be substituted by one or more deuteriums.

[0087] Preferably, at least one of Ar1 to Ar6 is selected from the group represented by Formula 1-b, including: one of Ar1 to Ar6 is selected from this group. Specifically, Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 is selected from this group; two of Ar1 to Ar6 are selected from this group. Specifically, Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar5, Ar3 and Ar4, Ar3 and Ar5, Ar5 and Ar6 are selected from this group; three of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2 and Ar3, Ar1, Ar2 and Ar5, Ar1, Ar3 and Ar4, Ar1, Ar3 and Ar5, Ar1, Ar5 and Ar6, Ar3, Ar4 and Ar5, Ar3, Ar5 and Ar6 are selected from this group; four of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2, Ar3 and Ar4, Ar1, Ar2, Ar3 and Ar5, Ar1, Ar2, Ar5 and Ar6, Ar1, Ar3, Ar4 and Ar5, Ar1, Ar3, Ar5 and Ar6, Ar3, Ar4, Ar5 and Ar6 are selected from this group; five of Ar1 to Ar6 are selected from this group. Specifically, Ar1, Ar2, Ar3, Ar4 and Ar5, Ar1, Ar2, Ar3, Ar5 and Ar6 are selected from this group.

[0088] Preferably, Formula 1-b is selected from one of the following groups:

[0089]

[0090]

[0091] R7 is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl.

[0092] m1 is selected from 0, 1, 2, 3 or 4; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2 or 3; m4 is selected from 0, 1, 2, 3, 4, 5 or 6; m5 is selected from 0, 1, 2, 3, 4 or 5; m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0093] Preferably, the R x , R y are the same or different and are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopropyl, benzocyclobutyl, benzocyclobutenyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, methylfluorenyl, phenylfluorenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or adjacent R x , R y are bonded to each other to form a substituted or unsubstituted ring, and the above groups may be substituted by one or more deuteriums.

[0094] Preferably, the R z are the same or different and are each independently selected from methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, benzocyclopropyl, benzocyclobutyl, benzocyclobutenyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, methylfluorenyl, phenylfluorenyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0095] More preferably, the formula 1-b is selected from one of the following groups

[0096]

[0097]

[0098] Preferably, R5 and R6 are the same or different and are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or a combination thereof, or adjacent R5 and adjacent R6 are bonded to each other to form a substituted or unsubstituted benzene ring;

[0099] R7 is the same or different and is each independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl;

[0100] m1 is selected from 0, 1, 2, 3 or 4; m2 is selected from 0, 1, 2, 3 or 4; m3 is selected from 0, 1, 2 or 3; m4 is selected from 0, 1, 2, 3, 4, 5 or 6; m5 is selected from 0, 1, 2, 3, 4 or 5; m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0101] More preferably, R5 and R6 are the same or different and are selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and one or a combination thereof, and the above groups may be substituted with one or more deuteriums.

[0102] More preferably, R7 is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilylmethane, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and one of them, and the above groups may be substituted with one or more deuteriums.

[0103] Preferably, at least one of Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 is selected from the group shown in 1-a, and at least one is selected from the group shown in 1-b, and the rest are independently selected from one or a combination of the following groups:

[0104]

[0105] R8 is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, or two adjacent R8s are bonded to each other to form a substituted or unsubstituted ring;

[0106] R9 is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;

[0107] R1 is selected from 0, 1, 2, 3, 4 or 5; R2 is selected from 0, 1, 2, 3 or 4; R3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; R4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; R5 is selected from 0, 1, 2 or 3; R6 is selected from 0, 1, 2, 3, 4, 5 or 6; R7 is selected from 0 or 1; R8 is selected from 0, 1 or 2;

[0108] S1 is selected from 0, 1 or 2; S2 is selected from 0, 1, 2, 3 or 4; S3 is selected from 0, 1, 2, 3, 4, 5 or 6; S4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; S5 is selected from 0, 1, 2, 3, 4 or 5; S6 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; S7 is selected from 0, 1, 2 or 3.

[0109] More preferably, at least one of Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 is selected from the group shown in 1-a, and at least one is selected from the group shown in 1-b, and the rest are independently selected from one or a combination of the following groups:

[0110]

[0111] R8s, which may be the same or different, are each independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutyl, substituted or unsubstituted indanyl, substituted or unsubstituted indenyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted dihydronaphthyl, substituted or unsubstituted benzocycloheptyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, or two adjacent R8s are bonded to form a substituted or unsubstituted benzene ring;

[0112] R9 is the same as or different from and is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, and substituted or unsubstituted quinoxalinyl.

[0113] More preferably, R8 is the same as or different from and is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilylmethane, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0114] More preferably, R9 is the same as or different from and is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilylmethane, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0115] Preferably, R1, R2, and R3 are the same as or different from and are selected from one of hydrogen, deuterium, tritium, cyano, nitro, methyl, ethyl, propyl, butyl, trifluoromethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutyl, indanyl, tetrahydronaphthyl, benzocycloheptyl, indenyl, dihydronaphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0116] Preferably, L1, L2, L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, or one or a combination of the following groups:

[0117]

[0118] v is the same or different and is each independently selected from CR a or N;

[0119] R a is selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or two adjacent Rs a are bonded to each other to form a substituted or unsubstituted ring;

[0120] W is selected from O, S, CR c R d or NR w ;

[0121] R c and R d are the same or different and are each independently selected from one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl, or adjacent Rs c and R d are bonded to each other to form a substituted or unsubstituted ring;

[0122] R w is selected from one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0123] Preferably, L1, L2, L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, or one or a combination of the following groups:

[0124]

[0125]

[0126] R eOne selected from the same or different ones of hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted C3-C30 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group;

[0127] Said t1 is selected from 0, 1, 2, 3 or 4; said t2 is selected from 0, 1, 2, 3, 4, 5 or 6; said t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said t4 is selected from 0, 1, 2 or 3; said t5 is selected from 0, 1 or 2; said t6 is selected from 0 or 1; said t7 is selected from 0, 1, 2, 3, 4 or 5; said t8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; said t9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0128] More preferably, said L1, L2, L3, L4, L5, L6 are the same or different and are selected from a single bond, or one or a combination of the following groups,

[0129]

[0130] Preferably, said R a The same or different ones are selected from hydrogen, deuterium, tritium, cyano group, halogen, nitro group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted trimethylsilyl group, substituted or unsubstituted triethylsilyl group, substituted or unsubstituted triphenylsilyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group;

[0131] Said R eOne selected from the same or different groups of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl.

[0132] More preferably, the R a One selected from the same or different groups of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, silyl, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0133] More preferably, the R e One selected from the same or different groups of hydrogen, deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, silyl, trifluoromethyl, trimethylsilylmethane, triethylsilyl, triphenylsilyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the above groups may be substituted by one or more deuteriums.

[0134] Preferably, the triamine compound is selected from any one of the structures shown below,

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] The above lists some specific chemical structures of the triamine compounds shown in Formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in Formula 1 with substituents being the groups defined above should be included.

[0171] In addition, the present invention also provides an organic electroluminescent device, which contains the triamine compound of the present invention described above.

[0172] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer. The organic layer is located between the cathode and the anode or outside one or more of the anode and the cathode. The organic layer contains the triamine compound of the present invention described above.

[0173] Preferably, the organic layer includes a hole transport region, and the hole transport region contains the triamine compound of the present invention described above.

[0174] Preferably, the hole transport region includes a hole transport layer, and the hole transport layer contains the triamine compound of the present invention described above.

[0175] Preferably, the hole transport layer includes a first hole transport layer and / or a second hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer. The first hole transport layer and / or the second hole transport layer contains the triamine compound of the present invention described above.

[0176] Preferably, the organic layer includes a cover layer, and the cover layer contains the triamine compound of the present invention described above.

[0177] The functional layers of the organic electroluminescent device of the present invention may contain at least one of the following functional layers: 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 cover layer, etc. Any functional layer with hole injection and / or transport properties, electron injection and / or transport properties, light-emitting properties, or light extraction properties should be included. Each functional layer may be composed of a single-layer thin film or multiple-layer thin films, and each thin film may be composed of only one material or multiple materials.

[0178] The present invention does not particularly limit the materials of each thin film in the organic electroluminescent device, and substances known in the art can be used. The following separately introduces each organic functional layer of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device:

[0179] The anode of the present invention preferably uses a material with a relatively high work function to enable holes to smoothly enter the organic layer. The anode material includes metal oxides, metal alloys, metals, conductive polymers, etc., but is not limited thereto. Specific examples of the anode material may include gold (Au), platinum (Pt), aluminum (Al), indium zinc oxide (IZO), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but is not limited thereto.

[0180] The hole injection layer of the present invention preferably uses a material with good hole injection ability and a HOMO energy level matching the anode. The hole injection material includes metal oxides, phthalocyanine metal complexes, arylamine derivatives, polymers, etc., but is not limited thereto. Specific examples of the hole injection material may include N,N'-bis[4-bis(m-tolyl)aminophenyl]-N,N'-diphenylbenzidine (DNTPD), 4,4',4''-tris(N-(1-naphthyl)-N-phenylamino)triphenylamine (1-TNATA), 4,4',4'-tris[2-naphthylphenylamino]triphenylamine (2-TNATA), 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT-CN), poly(4-vinyltriphenylamine) (PVTPA), vanadium pentoxide (V2O5), etc., but is not limited thereto.

[0181] The hole transport layer of the present invention preferably uses a material with good hole transport performance. The hole transport material includes arylamine derivatives, carbazole derivatives, polymers, etc., but is not limited thereto. Specific examples of the hole transport material may include N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N4,N4'-bis(biphenyl-4-yl)-N4,N4'-diphenylbiphenyl-4,4'-diamine (TPD-10), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 1,3,5-tris(9-carbazolyl)benzene (TCB), 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA), etc., but is not limited thereto. The triamine compound of Formula 1 of the present invention is preferred.

[0182] The electron blocking layer of the present invention preferably has a material with good hole transport ability and electron blocking ability. The electron blocking material includes, but is not limited to, aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the electron blocking material may include N,N'-bis(naphthalen-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-yl)-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine, etc., but are not limited thereto. The triamine compound of Formula 1 of the present invention is preferred.

[0183] The light-emitting layer of the present invention comprises a host material and a doping material. The doping ratio of the host material and the doping material can be determined according to the materials used. Generally, the doping ratio of the doping material is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0184] The host material of the light-emitting layer not only needs to have bipolar charge transport properties, but also needs appropriate energy levels to effectively transfer the excitation energy to the guest light-emitting material. The host material includes, but is not limited to, heterocyclic compounds, aromatic amine compounds, fused aromatic ring derivatives, metal complexes, silicon-containing compounds, etc. Specific examples may include 4,4'-bis(carbazol-9-yl)biphenyl (CBP), 1,3-bis(N-carbazolyl)benzene (MCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), tris(8-hydroxyquinoline)aluminum (Alq3), bis(8-hydroxyquinoline)zinc (Znq2), etc., but are not limited thereto.

[0185] The doping material can be a red light-emitting material, a green light-emitting material, or a blue light-emitting material. The doping material includes, but is not limited to, metal complexes, aromatic amine derivatives, styrylamine compounds, fused aromatic compounds, heterocyclic compounds, etc. Specific examples may include tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), bis(2-phenylpyridine)(acetylacetonato)iridium(III) (Ir(ppy)2(acac)), bis(2-benzo[h]quinoline-C2,N')(acetylacetonato)iridium(III) (Ir(bzq)2(acac)), bis(1-phenylisoquinoline)(acetylacetonato)iridium(III) (Ir(piq)2(acac)), tris(1-phenylisoquinoline)iridium(III) (Ir(piq)3), 2,5,8,11-tetra-tert-butylperylene (TBPe), etc., but are not limited thereto.

[0186] The hole blocking layer of the present invention preferably has a material with good electron transport ability and hole blocking ability. The hole blocking material includes metal complexes, heteroaromatic compounds, etc., but is not limited thereto. Specific examples may include bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-ol)aluminum (BAlq), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), etc., but is not limited thereto.

[0187] The electron transport layer of the present invention preferably has a material with good stability and high electron mobility. The electron transport material includes metal complexes, heteroaromatic compounds, polymers, etc., but is not limited thereto. Specific examples may include tris(8-hydroxyquinolinato)aluminum (Alq3), bis(8-hydroxyquinolinato)zinc(II) (Znq), 2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3,3,5,5-tetrakis(m-pyridyl)-benzene-3-yl]biphenyl (BP4mPy), 2-(4-(9,10-bis(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl)-1H-phenanthro[9,10-d]imidazole (ADN-PAimi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB), etc., but is not limited thereto.

[0188] The electron injection layer of the present invention preferably has a material with good electron injection ability and energy level matching with the cathode. The electron injection layer material includes metals, metal compounds, metal oxides, etc., but is not limited thereto. Specific examples may include ytterbium (Yb), lithium fluoride (LiF), magnesium fluoride (MgF), lithium 8-hydroxyquinolate (LiQ), cesium carbonate (Cs2CO3), rubidium acetate (CH3COORb), lithium oxide (Li2O), etc., but is not limited thereto.

[0189] The cathode of the present invention preferably has a material with a low work function. The cathode material includes metals, metal alloys, etc., but is not limited thereto. Specific examples of the cathode material may include aluminum (Al), silver (Ag), gold (Au), lithium (Li), magnesium (Mg), magnesium-silver alloy (Mg:Ag), lithium-aluminum alloy (Li:Al), etc., but is not limited thereto.

[0190] The covering material of the present invention has the function of coupling out the light trapped in the device. The covering material includes, but is not limited to, arylamine derivatives, metal compounds, carbazole derivatives, etc. Specific examples may include tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-bis(carbazol-9-yl)biphenyl (CBP), etc., but are not limited to these. The triamine compound of Formula 1 of the present invention is preferred.

[0191] There is no particular limitation on the preparation method of each layer of thin film in the organic electroluminescent device of the present invention, and vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer printing, etc. can be used, but are not limited to these.

[0192] The organic electroluminescent device of the present invention is mainly applied to the fields of information display technology, lighting, and planar light source. In information display, it is widely used in various information displays, such as mobile phones, tablet computers, flat-panel TVs, smart watches, VR, vehicle-mounted systems, digital cameras, wearable devices, etc.

[0193] The following examples illustrate the present invention in more detail. However, the following examples are only used to illustrate this specification, and the scope of this specification is not limited to these examples.

[0194] Synthesis Examples

[0195] Raw materials and reagents: The present invention has no particular limitation on the raw materials or reagents used in the following synthesis examples, and they can be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all of reagent grade.

[0196] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube type organic elemental analyzer (Elementar, Germany).

[0197] There is no particular limitation on the preparation method of the triamine compound shown in Formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, etc. The triamine compound shown in Formula 1 of the present invention can be prepared by the following synthesis route.

[0198] Synthesis of intermediates:

[0199]

[0200] Synthesis of compounds:

[0201] When intermediate M1, intermediate M2, and intermediate M3 are different from each other, the synthesis route of the compound of Formula 1:

[0202]

[0203] When intermediate M1 and intermediate M3 are the same as each other, the synthetic route of the compound of formula 1:

[0204]

[0205] When intermediate M1, intermediate M2 and intermediate M3 are the same as each other, the synthetic route of the compound of formula 1:

[0206]

[0207] Said Xn is a halogen, for example Xn is the same or different and is selected from Cl, Br, I.

[0208] Synthesis Example 1: Synthesis of Compound 44

[0209]

[0210] Preparation of intermediate M1-44:

[0211] Under nitrogen protection, toluene (800 mL), a-44 (17.91 g, 120.00 mmol), b-44 (27.97 g, 120.00 mmol), Pd(dppf)Cl2 (1.05 g, 1.44 mmol) and sodium tert-butoxide (17.30 g, 180.00 mmol) were successively added to the reaction flask, stirred and dissolved, and refluxed for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate M1-44 (29.30 g, yield 81%), and the solid purity detected by HPLC was ≥99.80%. Mass spectrum m / z: 301.1841 (theoretical value: 301.1830).

[0212] Preparation of intermediate M2-44:

[0213] Under nitrogen protection, toluene (600 mL), c-44 (11.57 g, 70.00 mmol), d-44 (13.79 g, 70.00 mmol), Pd(dppf)Cl2 (0.61 g, 0.84 mmol) and sodium tert-butoxide (9.61 g, 100.00 mmol) were successively added to the reaction flask, stirred and dissolved, and refluxed for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate M2-44 (16.15 g, yield 82%), and the solid purity detected by HPLC was ≥99.84%. Mass spectrum m / z: 281.1219 (theoretical value: 281.1236).

[0214] Preparation of intermediate M3-44:

[0215] Under nitrogen protection, toluene (400mL), e-44 (6.76g, 50.00mmol), f-44 (12.71g, 50.00mmol), Pd(OAc)2 (0.11g, 0.50mmol), sodium tert-butoxide (7.21g, 75.00mmol) and tri-tert-butylphosphine (2.00mL, 1.00mmol, 0.5M in toluene solution) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 4 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization was performed with toluene / methanol (volume ratio 10:1) to obtain intermediate M3-44 (12.34g, yield 80%), and the solid purity was ≥99.87% by HPLC. Mass spectrum m / z: 308.1914 (theoretical value: 308.1906).

[0216] Preparation of intermediate A-44:

[0217] Under nitrogen protection, toluene (700mL), g-44 (25.39g, 80.00mmol), M1-44 (24.11g, 80.00mmol), Pd (OAc) 2 (0.18g, 0.80mmol), sodium tert-butoxide (15.38g, 160.00mmol) and tri-tert-butylphosphine (3.20mL, 1.60mmol, 0.5M in toluene solution) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 6 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. It was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 9: 1) to obtain intermediate A-44 (31.02g, yield 79%), and the solid purity was ≥ 99.76% by HPLC. Mass spectrum m / z: 489.0874 (theoretical value: 489.0859).

[0218] Preparation of intermediate B-44:

[0219] Under nitrogen protection, toluene (400mL), A-44 (24.54g, 50.00mmol), M2-44 (14.07g, 50.00mmol), Pd2(dba)3 (0.46g, 0.50mmol), sodium tert-butoxide (9.61g, 100.00mmol) and tri-tert-butylphosphine (2.00mL, 1.00mmol, 0.5M in toluene solution) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. It was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 6:1) to obtain intermediate B-44 (26.27g, yield 76%), and the solid purity was ≥99.83% by HPLC. Mass spectrum m / z: 690.2843 (theoretical value: 690.2833).

[0220] Preparation of compound 44:

[0221] Under nitrogen protection, toluene (200 mL), B-44 (20.74 g, 30.00 mmol), M3-44 (9.25 g, 30.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol) and X-Phos (0.29 g, 0.60 mmol) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 4.5 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization with toluene gave compound 44 (20.52 g, yield 71%), and the solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 962.4952 (theoretical value: 962.4972). Theoretical element content (%) C 66 H 54 D7N3O2Si: C, 82.29; H, 7.11; N, 4.36. Measured element content (%): C, 82.31; H, 7.08; N, 4.40.

[0222] Synthesis Example 2: Synthesis of Compound 67

[0223]

[0224] According to the same preparation method as in Synthesis Example 1, replace a-44, b-44, c-44, d-44, e-44, f-44 with equimolar amounts of a-67, b-67, a-67, d-67, a-67, f-67 respectively to obtain Compound 67 (18.63 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 954.3383 (theoretical value: 954.3392). Theoretical elemental content (%) C 67 H 46 N4OS: C, 84.25; H, 4.85; N, 5.87. Measured elemental content (%): C, 84.29; H, 4.81; N, 5.90.

[0225] Synthesis Example 3: Synthesis of Compound 75

[0226]

[0227] According to the same preparation method as in Synthesis Example 1, replace a-44, c-44, d-44, e-44, f-44 with equimolar amounts of a-67, c-75, d-75, a-67, f-75 respectively to obtain Compound 75 (18.38 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 1003.3582 (theoretical value: 1003.3596). Theoretical elemental content (%) C 72 H 49 N3OS: C, 86.11; H, 4.92; N, 4.18. Measured elemental content (%): C, 86.07; H, 4.95; N, 4.20.

[0228] Synthesis Example 4: Synthesis of Compound 77

[0229]

[0230] According to the same preparation method as in Synthesis Example 1, replace a-44, b-44, c-44, d-44, e-44, f-44 with equimolar amounts of a-67, b-77, a-67, d-77, a-67, f-77 respectively to obtain Compound 77 (18.51 g), and the solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 994.3350 (theoretical value: 994.3341). Theoretical elemental content (%) C 69 H 46 N4O2S: C, 83.27; H, 4.66; N, 5.63. Measured elemental content (%): C, 83.30; H, 4.61; N, 5.65.

[0231] Synthesis Example 5: Synthesis of Compound 101

[0232]

[0233] According to the same preparation method as in Synthesis Example 1, a-44, b-44, c-44, d-44, e-44, f-44 were respectively replaced with equimolar amounts of a-101, d-44, a-67, b-44, a-67, f-101 to obtain Compound 101 (19.30 g), and the solid purity was detected by HPLC to be ≥99.96%. Mass spectrometry m / z: 959.4803 (theoretical value: 959.4815). Theoretical elemental content (%) C 70 H 61 N3O: C, 87.55; H, 6.40; N, 4.38. Measured elemental content (%): C, 87.51; H, 6.37; N, 4.42.

[0234] Synthesis Example 6: Synthesis of Compound 147

[0235]

[0236] Preparation of Intermediate M2-75:

[0237] Under nitrogen protection, toluene (1000 mL), c-75 (25.38 g, 150.00 mmol), d-75 (29.55 g, 150.00 mmol), Pd(dppf)Cl2 (1.32 g, 1.80 mmol) and sodium tert-butoxide (21.62 g, 225.00 mmol) were successively added to a reaction flask, stirred and dissolved, and refluxed for 9 hours. After the reaction was completed, it was cooled to room temperature, water was added, and it was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave Intermediate M2-75 (34.67 g, yield 81%), and the solid purity was detected by HPLC to be ≧99.86%. Mass spectrometry m / z: 285.1172 (theoretical value: 285.1154).

[0238] Preparation of Intermediate M2-147:

[0239] Under nitrogen protection, toluene (400mL), a-67 (4.66g, 50.00mmol), d-147 (12.35g, 50.00mmol), Pd(OAc)2 (0.11g, 0.50mmol), sodium tert-butoxide (7.21g, 75.00mmol) and tri-tert-butylphosphine (2.00mL, 1.00mmol, 0.5M in toluene solution) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 4 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization was performed with toluene / methanol (volume ratio 7:1) to obtain intermediate M2-147 (10.63g, yield 82%), and the solid purity was ≥99.71% by HPLC. Mass spectrum m / z: 259.0984 (theoretical value: 259.0997).

[0240] Preparation of intermediate C-147:

[0241] Under nitrogen protection, toluene (800mL), g-147 (13.52g, 50.00mmol), M2-75 (28.53g, 100.00mmol), Pd (OAc) 2 (0.27g, 1.20mmol), sodium tert-butoxide (9.61g, 100.00mmol) and tri-tert-butylphosphine (2.00mL, 1.00mmol, 0.5M in toluene solution) were added to the reaction bottle in sequence, stirred to dissolve, and refluxed for 5 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. It was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio 8: 1) to obtain intermediate C-147 (26.15g, yield 77%), and the solid purity was ≥ 99.75% by HPLC. Mass spectrum m / z: 678.2065 (theoretical value: 678.2074).

[0242] Preparation of compound 147:

[0243] Under nitrogen protection, toluene (300 mL), C-147 (20.38 g, 30.00 mmol), M2-147 (7.78 g, 30.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol) and X-Phos (0.29 g, 0.60 mmol) were successively added to a reaction flask, stirred and dissolved, and refluxed for 4.5 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallized with toluene to obtain compound 147 (20.03 g, yield 74%), and the solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: 901.3318 (theoretical value: 901.3304). Theoretical elemental content (%) C 64 H 43 N3O3: C, 85.22; H, 4.80; N, 4.66. Measured elemental content (%): C, 85.18; H, 4.77; N, 4.61.

[0244] Synthesis Example 7: Synthesis of Compound 173

[0245]

[0246] According to the same preparation method as in Synthesis Example 6, d-75, d-147, and g-147 were respectively replaced with equimolar amounts of b-173, b-173, and g-173 to obtain compound 173 (19.83 g), and the solid purity detected by HPLC was ≥99.91%. Mass spectrum m / z: 917.3351 (theoretical value: 917.3366). Theoretical elemental content (%) C 63 H 43 N5O3: C, 82.42; H, 4.72; N, 7.63. Measured elemental content (%): C, 82.39; H, 4.76; N, 7.58.

[0247] Synthesis Example 8: Synthesis of Compound 182

[0248]

[0249] According to the same preparation method as in Synthesis Example 6, c-75 and d-75 were respectively replaced with equimolar amounts of a-67 and b-182 to obtain compound 182 (17.59 g), and the solid purity detected by HPLC was ≥99.97%. Mass spectrum m / z: 849.2999 (theoretical value: 849.2991). Theoretical elemental content (%) C 60 H 39N3O3: C, 84.78; H, 4.62; N, 4.94. Measured elemental content (%): C, 84.81; H, 4.58; N, 4.90.

[0250] Synthesis Example 9: Synthesis of Compound 216

[0251]

[0252] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-67, b-216, and d-216 respectively to obtain Compound 216 (18.40 g), and the solid purity detected by HPLC is ≥99.95%. Mass spectrometry m / z: 901.3321 (theoretical value: 901.3304). Theoretical elemental content (%) C 64 H 43 N3O3: C, 85.22; H, 4.80; N, 4.66. Measured elemental content (%): C, 85.18; H, 4.75; N, 4.68.

[0253] Synthesis Example 10: Synthesis of Compound 246

[0254]

[0255] According to the same preparation method as in Synthesis Example 6, replace d-75 and a-67 with equimolar amounts of b-216 and c-246 respectively to obtain Compound 246 (21.45 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 1035.4413 (theoretical value: 1035.4400). Theoretical elemental content (%) C 74 H 57 N3O3: C, 85.77; H, 5.54; N, 4.05. Measured elemental content (%): C, 85.81; H, 5.49; N, 4.07.

[0256] Synthesis Example 11: Synthesis of Compound 262

[0257]

[0258] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and a-67 with equimolar amounts of a-262, d-44, and c-262 respectively to obtain Compound 262 (20.31 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 1009.4105 (theoretical value: 1009.4120). Theoretical elemental content (%) C 72 H 39D8N3O3: C, 85.60; H, 5.49; N, 4.16. Measured elemental content (%): C, 85.56; H, 5.52; N, 4.21.

[0259] Synthesis Example 12: Synthesis of Compound 290

[0260]

[0261] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-290, d-44, and d-173 respectively to obtain Compound 290 (19.98 g), and the solid purity detected by HPLC is ≥99.96%. Mass spectrometry m / z: 911.3923 (theoretical value: 911.3932). Theoretical elemental content (%) C 64 H 33 D 10 N3O3: C, 84.28; H, 5.85; N, 4.61. Measured elemental content (%): C, 84.32; H, 5.80; N, 4.57.

[0262] Synthesis Example 13: Synthesis of Compound 321

[0263]

[0264] According to the same preparation method as in Synthesis Example 6, replace c-75 and d-147 with equimolar amounts of a-321 and d-321 respectively to obtain Compound 321 (20.84 g), and the solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 1051.4152 (theoretical value: 1051.4171). Theoretical elemental content (%) C 74 H 57 N3O2S: C, 84.46; H, 5.46; N, 3.99. Measured elemental content (%): C, 84.41; H, 5.42; N, 3.97.

[0265] Synthesis Example 14: Synthesis of Compound 323

[0266]

[0267] According to the same preparation method as in Synthesis Example 6, replace d-75 and d-147 with equimolar amounts of b-323 and d-323 respectively to obtain Compound 323 (20.88 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 993.3377 (theoretical value: 993.3389). Theoretical elemental content (%) C 70 H 47N3O2S: C, 84.57; H, 4.77; N, 4.23. Measured elemental content (%): C, 84.61; H, 4.82; N, 4.20.

[0268] Synthesis Example 15: Synthesis of Compound 328

[0269]

[0270] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-321, d-44, and d-328 respectively to obtain Compound 328 (20.28 g), and the solid purity detected by HPLC is ≥99.96%. Mass spectrometry m / z: 993.3397 (theoretical value: 993.3389). Theoretical elemental content (%) C 70 H 47 N3O2S: C, 84.57; H, 4.77; N, 4.23. Measured elemental content (%): C, 84.54; H, 4.80; N, 4.26.

[0271] Synthesis Example 16: Synthesis of Compound 353

[0272]

[0273] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-353, b-353, and d-353 respectively to obtain Compound 353 (21.26 g), and the solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 997.3717 (theoretical value: 997.3702). Theoretical elemental content (%) C 70 H 51 N3O2S: C, 84.22; H, 5.15; N, 4.21. Measured elemental content (%): C, 84.18; H, 5.19; N, 4.23.

[0274] Synthesis Example 17: Synthesis of Compound 359

[0275]

[0276] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-67, b-359, and d-359 respectively to obtain Compound 359 (20.33 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 927.3813 (theoretical value: 927.3825). Theoretical elemental content (%) C 69 H 49N3O2: C, 86.70; H, 5.32; N, 4.53. Measured elemental content (%): C, 86.67; H, 5.29; N, 4.57.

[0277] Synthesis Example 18: Synthesis of Compound 377

[0278]

[0279] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-67, d-44, and d-377 respectively to obtain Compound 377 (19.46 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 939.3817 (theoretical value: 939.3825). Theoretical elemental content (%) C 68 H 49 N3O2: C, 86.87; H, 5.25; N, 4.47. Measured elemental content (%): C, 86.90; H, 5.21; N, 4.42.

[0280] Synthesis Example 19: Synthesis of Compound 389

[0281]

[0282] According to the same preparation method as in Synthesis Example 6, replace c-75 and d-147 with equimolar amounts of a-67 and d-389 respectively to obtain Compound 389 (19.75 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 967.4118 (theoretical value: 967.4138). Theoretical elemental content (%) C 70 H 53 N3O2: C, 86.84; H, 5.52; N, 4.34. Measured elemental content (%): C, 86.80; H, 5.49; N, 4.36.

[0283] Synthesis Example 20: Synthesis of Compound 392

[0284]

[0285] According to the same preparation method as in Synthesis Example 6, replace d-147 with an equimolar amount of d-392 to obtain Compound 392 (21.43 g), and the solid purity detected by HPLC is ≥99.95%. Mass spectrometry m / z: 1019.4460 (theoretical value: 1019.4451). Theoretical elemental content (%) C 74 H 57N3O2: C, 87.11; H, 5.63; N, 4.12. Measured elemental content (%): C, 87.15; H, 5.58; N, 4.16.

[0286] Synthesis Example 21: Synthesis of Compound 495

[0287]

[0288] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-495, d-44, and d-495 respectively to obtain Compound 495 (19.68 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 910.4075 (theoretical value: 910.4092). Theoretical elemental content (%) C 64 H 34 D 10 N4O2: C, 84.37; H, 5.97; N, 6.15. Measured elemental content (%): C, 84.40; H, 5.93; N, 6.12.

[0289] Synthesis Example 22: Synthesis of Compound 511

[0290]

[0291] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, and d-147 with equimolar amounts of a-67, d-147, c-75, and d-44 respectively to obtain Compound 511 (19.71 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 875.3138 (theoretical value: 875.3148). Theoretical elemental content (%) C 62 H 41 N3O3: C, 85.01; H, 4.72; N, 4.80. Measured elemental content (%): C, 85.05; H, 4.69; N, 4.76.

[0292] Synthesis Example 23: Synthesis of Compound 550

[0293]

[0294] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, and d-147 with equimolar amounts of a-67, d-147, c-75, and d-550 respectively to obtain Compound 550 (20.88 g), and the solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 979.3788 (theoretical value: 979.3774). Theoretical elemental content (%) C 70 H49 N3O3: C, 85.78; H, 5.04; N, 4.29. Measured elemental content (%): C, 85.81; H, 5.01; N, 4.34.

[0295] Synthesis Example 24: Synthesis of Compound 556

[0296]

[0297] According to the same preparation method as in Synthesis Example 6, c-75, d-75, a-67, and d-147 were respectively replaced with equimolar amounts of a-67, d-173, c-75, and d-556 to obtain Compound 556 (20.14 g), and the solid purity was ≥99.97% by HPLC detection. Mass spectrometry m / z: 1001.3626 (theoretical value: 1001.3617). Theoretical elemental content (%) C 72 H 47 N3O3: C, 86.29; H, 4.73; N, 4.19. Measured elemental content (%): C, 86.32; H, 4.69; N, 4.21.

[0298] Synthesis Example 25: Synthesis of Compound 570

[0299]

[0300] According to the same preparation method as in Synthesis Example 6, c-75, d-75, a-67, and d-147 were respectively replaced with equimolar amounts of a-67, b-570, c-75, and b-353 to obtain Compound 570 (19.91 g), and the solid purity was ≥99.94% by HPLC detection. Mass spectrometry m / z: 975.3449 (theoretical value: 975.3461). Theoretical elemental content (%) C 70 H 45 N3O3: C, 86.13; H, 4.65; N, 4.30. Measured elemental content (%): C, 86.09; H, 4.67; N, 4.26.

[0301] Synthesis Example 26: Synthesis of Compound 573

[0302]

[0303] According to the same preparation method as in Synthesis Example 6, c-75, d-75, a-67, and d-147 were respectively replaced with equimolar amounts of a-67, b-573, c-75, and b-216 to obtain Compound 573 (21.05 g), and the solid purity was ≥99.91% by HPLC detection. Mass spectrometry m / z: 987.4409 (theoretical value: 987.4400). Theoretical elemental content (%) C70 H 57 N3O3: C, 85.08; H, 5.81; N, 4.25. Measured elemental content (%): C, 85.11; H, 5.77; N, 4.27.

[0304] Synthesis Example 27: Synthesis of Compound 657

[0305]

[0306] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-44, d-147, and d-44 respectively to obtain Compound 657 (20.68 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 943.3610 (theoretical value: 943.3625). Theoretical elemental content (%) C 62 H 53 N3O3Si2: C, 78.86; H, 5.66; N, 4.45. Measured elemental content (%): C, 78.81; H, 5.70; N, 4.42.

[0307] Synthesis Example 28: Synthesis of Compound 694

[0308]

[0309] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, and d-147 with equimolar amounts of a-67, d-67, and d-694 respectively to obtain Compound 694 (19.62 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 907.2680 (theoretical value: 907.2691). Theoretical elemental content (%) C 62 H 41 N3OS2: C, 82.00; H, 4.55; N, 4.63. Measured elemental content (%): C, 82.04; H, 4.52; N, 4.66.

[0310] Synthesis Example 29: Synthesis of Compound 802

[0311]

[0312] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, and d-147 with equimolar amounts of a-67, d-359, c-802, and d-75 respectively to obtain Compound 802 (20.33 g), and the solid purity detected by HPLC is ≥99.95%. Mass spectrometry m / z: 981.4677 (theoretical value: 981.4658). Theoretical elemental content (%) C 72H 59 N3O: C, 88.04; H, 6.05; N, 4.28. Measured elemental content (%): C, 88.08; H, 6.03; N, 4.31.

[0313] Synthesis Example 30: Synthesis of Compound 827

[0314]

[0315] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, d-147 with equimolar amounts of a-67, b-827, c-827, b-216 respectively to obtain Compound 827 (20.32 g), and the solid purity detected by HPLC is ≥99.96%. Mass spectrometry m / z: 1025.4083 (theoretical value: 1025.4094). Theoretical elemental content (%) C 74 H 51 N5O: C, 86.61; H, 5.01; N, 6.82. Measured elemental content (%): C, 86.59; H, 5.05; N, 6.79.

[0316] Synthesis Example 31: Synthesis of Compound 835

[0317]

[0318] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, d-147 with equimolar amounts of a-67, b-44, c-835, d-75 respectively to obtain Compound 835 (19.14 g), and the solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 861.3338 (theoretical value: 861.3355). Theoretical elemental content (%) C 62 H 43 N3O2: C, 86.39; H, 5.03; N, 4.87. Measured elemental content (%): C, 86.43; H, 5.00; N, 4.90.

[0319] Synthesis Example 32: Synthesis of Compound 853

[0320]

[0321] According to the same preparation method as in Synthesis Example 1, a-44, c-44, d-44, e-44, and f-44 were respectively replaced with equimolar amounts of a-67, a-67, d-853, c-835, and b-216 to obtain Compound 853 (20.03 g), and the solid purity was detected by HPLC to be ≥99.97%. Mass spectrometry m / z: 939.3813 (theoretical value: 939.3825). Theoretical elemental content (%) C 68 H 49 N3O2: C, 86.87; H, 5.25; N, 4.47. Measured elemental content (%): C, 86.90; H, 5.21; N, 4.45.

[0322] Synthesis Example 33: Synthesis of Compound 878

[0323]

[0324] Preparation of Intermediate M1-878:

[0325] Under nitrogen protection, toluene (800 mL), c-835 (25.65 g, 140.00 mmol), b-77 (27.58 g, 140.00 mmol), Pd(dppf)Cl2 (1.46 g, 2.00 mmol), and sodium tert-butoxide (26.91 g, 280.00 mmol) were successively added to a reaction flask, stirred and dissolved, and refluxed for 8 hours. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized from ethyl acetate to obtain Intermediate M1-878 (33.11 g, yield 79%), and the solid purity was detected by HPLC to be ≧99.71%. Mass spectrometry m / z: 299.0958 (theoretical value: 299.0946).

[0326] Preparation of Compound 878:

[0327] Under nitrogen protection, toluene (500 mL), g-878 (9.44 g, 30.00 mmol), M1-878 (26.94 g, 90.00 mmol), Pd2(dba)3 (0.82 g, 0.90 mmol), sodium tert-butoxide (17.30 g, 180.00 mmol) and BINAP (1.76 g, 2.70 mmol) were successively added to the reaction flask, stirred and dissolved, and refluxed for 6 hours. After the reaction was completed, it was cooled to room temperature, water was added, extracted with dichloromethane, the organic layer was dried over anhydrous magnesium sulfate, filtered, the solvent was removed under reduced pressure, and recrystallized with toluene to obtain compound 878 (20.95 g, yield 72%), and the solid purity detected by HPLC was ≥99.96%. Mass spectrum m / z: 969.2828 (theoretical value: 969.2839). Theoretical elemental content (%) C 66 H 39 N3O6: C, 81.72; H, 4.05; N, 4.33. Measured elemental content (%): C, 81.69; H, 4.07; N, 4.29.

[0328] Synthesis Example 34: Synthesis of Compound 909

[0329]

[0330] According to the same preparation method as in Synthesis Example 1, a-44, b-44, c-44, d-44, e-44, f-44, g-44 were respectively replaced with equimolar amounts of c-75, b-909, c-75, d-909, a-67, f-909, g-909 to obtain compound 909 (19.18 g), and the solid purity detected by HPLC was ≥99.92%. Mass spectrum m / z: 1047.4097 (theoretical value: 1047.4081). Theoretical elemental content (%) C 74 H 53 DN4OS: C, 84.78; H, 5.29; N, 5.34. Measured elemental content (%): C, 84.80; H, 5.33; N, 5.30.

[0331] Synthesis Example 35: Synthesis of Compound 967

[0332]

[0333] According to the same preparation method as in Synthesis Example 6, d-75 was replaced with an equimolar amount of b-967 to obtain compound 967 (20.46 g), and the solid purity detected by HPLC was ≥99.98%. Mass spectrum m / z: 933.2836 (theoretical value: 933.2848). Theoretical elemental content (%) C 64 H 43N3OS2: C, 82.29; H, 4.64; N, 4.50. Measured elemental content (%): C, 82.32; H, 4.60; N, 4.47.

[0334] Synthesis Example 36: Synthesis of Compound 997

[0335]

[0336] According to the same preparation method as in Synthesis Example 6, replace c-75 and d-75 with equimolar amounts of a-997 and b-997 to obtain Compound 997 (20.57 g), and the solid purity detected by HPLC is ≥99.95%. Mass spectrometry m / z: 951.3969 (theoretical value: 951.3977). Theoretical elemental content (%) C 64 H 25 D 18 N3OS2: C, 80.72; H, 6.45; N, 4.41. Measured elemental content (%): C, 80.68; H, 6.49; N, 4.38.

[0337] Synthesis Example 37: Synthesis of Compound 1002

[0338]

[0339] According to the same preparation method as in Synthesis Example 6, replace d-75 and a-67 with equimolar amounts of b-1002 and c-1002 to obtain Compound 1002 (21.76 g), and the solid purity detected by HPLC is ≥99.93%. Mass spectrometry m / z: 1081.4049 (theoretical value: 1081.4038). Theoretical elemental content (%) C 75 H 51 D4N3OS2: C, 83.22; H, 5.49; N, 3.88. Measured elemental content (%): C, 83.19; H, 5.53; N, 3.83.

[0340] Synthesis Example 38: Synthesis of Compound 1003

[0341]

[0342] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, and g-147 with equimolar amounts of a-1003, b-967, c-1003, and g-1003 to obtain Compound 1003 (20.18 g), and the solid purity detected by HPLC is ≥99.97%. Mass spectrometry m / z: 988.3080 (theoretical value: 988.3097). Theoretical elemental content (%) C 66 H 40D3N5OS2: C, 80.13; H, 4.69; N, 7.08. Measured elemental content (%): C, 80.09; H, 4.72; N, 7.10.

[0343] Synthesis Example 39: Synthesis of Compound 1029

[0344]

[0345] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, a-67, d-147 with equimolar amounts of a-67, d-147, c-1029, d-1029 to obtain Compound 1029 (20.83 g), and the solid purity detected by HPLC is ≥99.94%. Mass spectrometry m / z: 963.3303 (theoretical value: 963.3315). Theoretical elemental content (%) C 65 H 49 N3O2SSi: C, 80.96; H, 5.12; N, 4.36. Measured elemental content (%): C, 80.92; H, 5.08; N, 4.38.

[0346] Synthesis Example 40: Synthesis of Compound 1100

[0347]

[0348] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, d-147 with equimolar amounts of a-67, b-967, d-1100 to obtain Compound 1100 (18.79 g), and the solid purity detected by HPLC is ≥99.98%. Mass spectrometry m / z: 857.2881 (theoretical value: 857.2898). Theoretical elemental content (%) C 59 H 43 N3S2: C, 82.58; H, 5.05; N, 4.90. Measured elemental content (%): C, 82.60; H, 5.01; N, 4.88.

[0349] Synthesis Example 41: Synthesis of Compound 1106

[0350]

[0351] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, d-147 with equimolar amounts of a-67, b-997, d-1106 to obtain Compound 1106 (19.53 g), and the solid purity detected by HPLC is ≥99.91%. Mass spectrometry m / z: 929.2890 (theoretical value: 929.2898). Theoretical elemental content (%) C 65 H 43N3S2: C, 83.93; H, 4.66; N, 4.52. Measured elemental content (%): C, 83.89; H, 4.71; N, 4.49.

[0352] Synthesis Example 42: Synthesis of Compound 1164

[0353]

[0354] According to the same preparation method as in Synthesis Example 1, replace a-44, c-44, d-44, e-44, f-44, g-44 with equimolar amounts of a-67, a-67, b-827, a-67, f-1164, g-1164 respectively to obtain Compound 1164 (18.26 g), and the solid purity detected by HPLC is ≥99.92%. Mass spectrometry m / z: 935.3969 (theoretical value: 935.3988). Theoretical elemental content (%) C 68 H 49 N5: C, 87.24; H, 5.28; N, 7.48. Measured elemental content (%): C, 87.28; H, 5.30; N, 7.51.

[0355] Synthesis Example 43: Synthesis of Compound 1183

[0356]

[0357] According to the same preparation method as in Synthesis Example 6, replace c-75, d-75, d-147 with equimolar amounts of a-67, d-44, d-1183 to obtain Compound 1183 (18.36 g), and the solid purity detected by HPLC is ≥99.96%. Mass spectrometry m / z: 955.4129 (theoretical value: 955.4138). Theoretical elemental content (%) C 69 H 53 N3O2: C, 86.67; H, 5.59; N, 4.39. Measured elemental content (%): C, 86.62; H, 5.61; N, 4.43.

[0358] Device Example

[0359] In the present invention, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with 5% glass cleaning solution for 20 minutes each time, and then ultrasonically cleaned twice with deionized water for 10 minutes each time. Ultrasonically clean with acetone and isopropyl acetone for 20 minutes in sequence and dry at 120 °C. All organic materials are sublimated and their purity is above 99.99%.

[0360] A combined IVL test system consisting of test software, a computer, a K2400 digital source meter produced by Keithley Corporation in the United States, and a PR788 spectral scanning luminance meter from PhotoResearch Corporation in the United States is used to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. The lifetime test is carried out using an M6000 OLED lifetime test system from McScience. The test environment is the atmospheric environment, and the temperature is room temperature.

[0361] Example 1: Preparation of Organic Electroluminescent Device 1

[0362] HAT-CN is vacuum-evaporated on the ITO / Ag / ITO anode as a hole injection layer with a thickness of 9 nm; the compound 44 of the present invention is vacuum-evaporated on the hole injection layer as a hole transport layer with a thickness of 115 nm; the host material CBP and the doping material Ir(piq)3 are vacuum-evaporated on the hole transport layer, and the two are doped in a ratio of CBP:Ir(piq)3 = 98:2 (wt%) to form a light-emitting layer with a thickness of 25 nm; BCP:LiQ = 1:1 (wt%) is vacuum-evaporated on the light-emitting layer as an electron transport layer with a thickness of 29 nm; LiF is vacuum-evaporated on the electron transport layer as an electron injection layer with an evaporation thickness of 1.1 nm; Mg:Ag = 1:9 is vacuum-evaporated on the electron injection layer as a cathode with a thickness of 15 nm; then CP-1 is vacuum-evaporated on the cathode as a covering layer with a thickness of 71 nm.

[0363] Examples 2 to 43: Preparation of Organic Electroluminescent Devices 2 to 43

[0364] The compound 44 in the hole transport layer of Example 1 is replaced with compound 67, compound 75, compound 77, compound 101, compound 147, compound 173, compound 182, compound 216, compound 246, compound 262, compound 290, compound 321, compound 323, compound 328, compound 353, compound 359, compound 377, compound 389, compound 392, compound 495, compound 511, compound 550, compound 556, compound 570, compound 573, compound 657, compound 694, compound 802, compound 827, compound 835, compound 853, compound 878, compound 909, compound 967, compound 997, compound 1002, compound 1003, compound 1029, compound 1100, compound 1106, compound 1164, compound 1183 respectively, and the other steps are the same, obtaining organic electroluminescent devices 2 to 43.

[0365] Comparative Examples 1 to 2: Preparation of Comparative Organic Electroluminescent Devices 1 to 2

[0366] In Example 1, Compound 44 in the hole transport layer was replaced with R-1 and R-2 respectively, and other steps were the same, to obtain Comparative Organic Electroluminescent Devices 1-2.

[0367]

[0368]

[0369] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 1-43 and Comparative Examples 1-2 of the present invention are shown in Table 1.

[0370] Table 1 Test Data of Luminescence Characteristics of Organic Electroluminescent Devices

[0371]

[0372]

[0373] It can be seen from Table 1 that compared with Comparative Devices 1-2, the organic electroluminescent devices of the present invention have lower driving voltage, higher luminous efficiency and longer service life, and the performance of the devices is more excellent.

[0374] Example 44: Preparation of Organic Electroluminescent Device 44

[0375] HI-1:HI-2 = 6:94 was vacuum-evaporated on the ITO / Ag / ITO anode as the hole injection layer with a thickness of 8 nm; NPB was vacuum-evaporated on the hole injection layer as the first hole transport layer with a thickness of 60 nm; Compound 44 of the present invention was vacuum-evaporated on the first hole transport layer as the second hole transport layer with a thickness of 55 nm; the host material CBP and the doping material Ir(piq)2(acac) were vacuum-evaporated on the second hole transport layer, and the two were doped in a ratio of CBP:Ir(piq)2(acac) = 98:2 (wt%) to form the light-emitting layer with a thickness of 20 nm; BCP:LiQ = 1:1 (wt%) was vacuum-evaporated on the light-emitting layer as the electron transport layer with a thickness of 25 nm; LiF was vacuum-evaporated on the electron transport layer as the electron injection layer with an evaporation thickness of 0.9 nm; Mg:Ag = 1:9 was vacuum-evaporated on the electron injection layer as the cathode with a thickness of 12 nm; then CP-1 was vacuum-evaporated on the cathode as the cover layer with a thickness of 70 nm.

[0376] Examples 45-86: Preparation of Organic Electroluminescent Devices 45-86

[0377] In Example 44, compound 44 in the second hole transport layer was replaced with compound 67, compound 75, compound 77, compound 101, compound 147, compound 173, compound 182, compound 216, compound 246, compound 262, compound 290, compound 321, compound 323, compound 328, compound 353, compound 359, compound 377, compound 389, compound 392, compound 495, compound 511, compound 550, compound 556, compound 570, compound 573, compound 657, compound 694, compound 802, compound 827, compound 835, compound 853, compound 878, compound 909, compound 967, compound 997, compound 1002, compound 1003, compound 1029, compound 1100, compound 1106, compound 1164, and compound 1183 respectively, and the other steps were the same, obtaining organic electroluminescent devices 45 to 86.

[0378] Comparative Examples 3 to 4: Preparation of comparative organic electroluminescent devices 3 to 4

[0379] In Example 44, compound 44 in the second hole transport layer was replaced with R-3 and R-4 respectively, and the other steps were the same, obtaining comparative organic electroluminescent devices 3 to 4.

[0380]

[0381] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 44 to 86 and Comparative Examples 3 to 4 of the present invention are shown in Table 2.

[0382] Table 2 Test data of the luminescence characteristics of organic electroluminescent devices

[0383]

[0384]

[0385]

[0386] As can be seen from Table 2, compared with the comparative devices, the organic electroluminescent devices containing the triamine compound of Formula 1 of the present invention in the second hole transport layer have a lower driving voltage, a higher luminous efficiency, and a longer service life.

[0387] Example 87: Preparation of organic electroluminescent device 87

[0388] 2-TNATA was vacuum-evaporated as a hole injection layer on the ITO / Ag / ITO anode with a thickness of 55 nm; NPB was vacuum-evaporated as a hole transport layer on the hole injection layer with a thickness of 110 nm; the host material CBP and the doping material Ir(ppy)2(acac) were vacuum-evaporated on the hole transport layer, and the two were doped in a ratio of CBP:Ir(ppy)2(acac)=93:7 (wt%) to form a light-emitting layer with a thickness of 23 nm; BTB:LiQ = 1:1 (wt%) was vacuum-evaporated as an electron transport layer on the light-emitting layer with a thickness of 27 nm; LiF was vacuum-evaporated as an electron injection layer on the electron transport layer with an evaporation thickness of 0.9 nm; Mg:Ag = 1:9 was vacuum-evaporated as a cathode on the electron injection layer with a thickness of 14 nm; then the compound 44 of the present invention was vacuum-evaporated as a covering layer on the cathode with a thickness of 72 nm.

[0389] Examples 88 to 106: Preparation of organic electroluminescent devices 88 to 106

[0390] The compound 44 in the covering layer of Example 87 was replaced with compound 77, compound 147, compound 182, compound 262, compound 353, compound 359, compound 392, compound 495, compound 511, compound 550, compound 570, compound 694, compound 802, compound 835, compound 967, compound 997, compound 1003, compound 1029, compound 1100 respectively, and the other steps were the same, obtaining organic electroluminescent devices 88 to 106.

[0391] Comparative Example 5: Preparation of comparative organic electroluminescent device 5

[0392] The compound 44 in the covering layer of Example 87 was replaced with R-5 respectively, and the other steps were the same, obtaining comparative organic electroluminescent device 5.

[0393]

[0394] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 87 to 106 and Comparative Example 5 of the present invention are shown in Table 3.

[0395] Table 3 Test data of the luminescence characteristics of organic electroluminescent devices

[0396]

[0397]

[0398] As can be seen from Table 3, compared with the comparative device 5, the organic electroluminescent device with the triamine compound of Formula 1 of the present invention in the covering layer has a lower driving voltage, a higher luminous efficiency, and more excellent device performance.

[0399] It should be noted that the present invention has been specifically described with individual embodiments. However, without departing from the principle of the present invention, those of ordinary skill in the art can make various improvements in form or details to the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triamine compound, characterized in that, The triamine compound is selected from one of Formula 1-1 to Formula 1-2, wherein at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in Formula 1-a, Formula 1-a is selected from one of the groups shown below, n1 is selected from 0, 1, 2, 3, 4, or 5; n2 is selected from 0, 1, 2, 3, or 4; n5 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; The "*" represents the connection site with L1, L2, L3, L4, L5, or L6; X is selected from O, S or NR b ; The R b is selected from phenyl, biphenyl, and naphthyl, and the above groups may be substituted by one or more deuteriums; R4s are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, and substituted or unsubstituted biphenyl; and at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in Formula 1-b, Formula 1-b is selected from one of the groups shown below, m1 is selected from 0, 1, 2, 3, or 4; m2 is selected from 0, 1, 2, 3, or 4; m3 is selected from 0, 1, 2, or 3; m4 is selected from 0, 1, 2, 3, 4, 5, or 6; The R x , R y is the same as or different from one selected from substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; R x , R y The substituents represented by "substituted" in the substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl in R x , R y include deuterium; The substituents represented by "substituted" in the substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl in R The R z is selected from one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; R z The substituents represented by "substituted" in the substituted or unsubstituted phenyl group, the substituted or unsubstituted biphenyl group, and the substituted or unsubstituted naphthyl group include deuterium, methyl, ethyl, propyl, and butyl; R5 and R6 are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted adamantyl, and substituted or unsubstituted phenyl; The remaining ones of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one or a combination of the groups shown below, Said R 8a One selected from the group consisting of the same or different hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted trimethylsilyl, substituted or unsubstituted triethylsilyl, substituted or unsubstituted triphenylsilyl, and substituted or unsubstituted adamantyl; Said R 8b Same or different, and is one selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, and substituted or unsubstituted phenyl; R8s are the same or different and are each independently selected from hydrogen and deuterium; R9s are the same or different and are each independently selected from hydrogen and deuterium; r1 is selected from 0, 1, 2, 3, 4, or 5; r2 is selected from 0, 1, 2, 3, or 4; r3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; r4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; r5 is selected from 0, 1, 2, or 3; r6 is selected from 0, 1, 2, 3, 4, 5, or 6; s2 is selected from 0, 1, 2, 3, or 4; s3 is selected from 0, 1, 2, 3, 4, 5, or 6; s4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; R1, R2, and R3 are the same or different and are each independently selected from hydrogen, deuterium, substituted or unsubstituted methyl, and substituted or unsubstituted ethyl; L1, L2, L3, L4, L5, and L6 are the same or different and are each independently selected from a single bond, or one or a combination of the groups shown below, The R a is the same as or different from one selected from hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted butyl; The R e is the same as or different from and is one selected from hydrogen and deuterium; t1 is selected from 0, 1, 2, 3, or 4; t2 is selected from 0, 1, 2, 3, 4, 5, or 6; t3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; t4 is selected from 0, 1, 2, or 3; t5 is selected from 0, 1, or 2; R4, R5, R6, R 8a , R 8b , R1, R2, R3, R a The substituents represented by "substituted" in the "substituted or unsubstituted" described above include the following groups, deuterium.

2. The triamine compound according to claim 1, characterized in that, Formula 1-a is selected from one of the groups shown below, 3. The triamine compound according to claim 1, characterized in that, Formula 1-b is selected from one of the groups shown below, 4. The triamine compound according to claim 1, wherein At least one of Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 is selected from the group shown in Formula 1-a, and at least one is selected from the group shown in Formula 1-b, and the rest are independently selected from one or a combination of the groups shown below, 5. The triamine compound according to claim 1, characterized in that, L1, L2, L3, L4, L5, L6 are the same or different and are selected from a single bond, or one of the groups shown below, 6. A triamine compound, characterized in that, The triamine compound is selected from any one of the structures shown below, 7. An organic electroluminescent device, characterized in that, The organic electroluminescent device contains the triamine compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, characterized in that, The organic electroluminescent device includes an anode, a cathode, and an organic layer. The organic layer is located between the cathode and the anode or outside one or more electrodes of the anode and the cathode. The organic layer contains the triamine compound according to any one of claims 1 to 6.

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