Triamine compound and organic electroluminescent device thereof

Abstract

According to the triamine compound and the organic electroluminescent device thereof provided by the invention, the triamine compound has relatively high hole mobility and proper triplet state energy level, the hole transport performance can be effectively improved, and the device can have relatively low driving voltage, relatively high luminous efficiency and relatively long service life; and when the material is used as a covering layer material, light limited in a device can be refracted out, and the material has good thermal stability. In conclusion, the triamine compound provided by the invention is simple to synthesize, the raw materials are easy to obtain, and the triamine compound can be widely applied to the fields of display, illumination, medical treatment and the like and has good application potential.

Description

Technical Field

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

[0002] OLED (Organic Light-Emitting Diode), also known as organic electro-optic display or organic light-emitting diode display, works by generating electrons and holes from the cathode and anode respectively under an applied voltage. These electrons and holes are transported within the organic layer and recombine in the light-emitting layer to generate excitons. The excitons then radiatively transition back to the ground state and emit light. OLEDs offer advantages such as wide viewing angles, rich colors, flexibility, thin and lightweight structures, short response times, and ease of production. They are gradually replacing traditional inorganic electroluminescent materials and are widely used in various fields such as display, lighting, and medicine.

[0003] In recent years, the structure and performance of organic light-emitting diodes (OLEDs) have been continuously improved, evolving from the earliest single-layer device structure to double-layer and even multi-layer device structures. Currently, sandwich structures are commonly used, mainly including a substrate, anode, hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, cathode, and capping layer.

[0004] Each functional layer requires suitable materials to achieve high luminous efficiency and long lifespan in OLED devices. However, current hole transport materials still suffer from poor hole mobility, low thermal stability, poor film formation properties, and energy level mismatch, leading to problems such as high driving voltage, low luminous efficiency, and short lifespan in organic light-emitting diodes (OLEDs). Secondly, capping layer materials cannot effectively refract light confined within the device and lack good thermal stability, requiring further improvement. Therefore, finding new materials with superior performance is currently key to overcoming the bottlenecks in OLED technology. Summary of the Invention

[0005] To address the problems of high driving voltage, low luminous efficiency, and short lifespan in organic electroluminescent devices, this invention provides a triamine compound and an organic electroluminescent device containing the triamine compound, which can significantly improve the above-mentioned problems, resulting in organic electroluminescent devices with low driving voltage, high luminous efficiency, and long lifespan.

[0006] Specifically, the present invention provides a triamine compound, which is shown in Formula I.

[0007]

[0008] R1 is independently selected from any one of deuterium, cyano, fluorine, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl;

[0009] The a0 is selected from 1, 2, or 3;

[0010] The Ar1 is selected from the group shown in formula a;

[0011] The Ar2 is selected from the group shown in formula a or formula b;

[0012] X and Y are independently selected from O or S;

[0013] The z and v are independently selected from CH or N;

[0014] The R2 and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent R2 or adjacent R3 are bonded to each other to form a substituted or unsubstituted ring;

[0015] The n1 is selected from 0, 1, 2, 3, 4 or 5;

[0016] The m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0017] The Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups.

[0018] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring in a fused cycloalcoholic group, or a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroarylene ring in a fused cycloalcoholic group.

[0019] Beneficial effects:

[0020] The triamine compounds provided by this invention have high hole mobility and suitable triplet energy levels, which can effectively improve hole transport performance, enabling devices to have lower driving voltage, higher luminous efficiency and longer lifespan; and when used as a capping layer material, they can refract light confined inside the device and have good thermal stability. Detailed Implementation

[0021] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0022] In the compounds of this invention, any atom not specified as a particular isotope includes any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0023] The halogen atom mentioned in this invention refers to fluorine, chlorine, bromine, and iodine atoms.

[0024] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Examples of the alkyl group include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, etc., but are not limited thereto. The chain alkyl group with more than three carbon atoms described in this invention includes its isomers; for example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on.

[0025] The “substituted or unsubstituted silyl group” mentioned in this invention refers to the -Si(Rw)3 group, wherein each Rw group, whether identical or different, is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each Rw is the same or different from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 30 carbon atoms, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each Rw is the same or different from the following groups: 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 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 norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C1-C25 silyl" refers to a silyl group substituted with a substituted or unsubstituted C1-C25 alkyl or aryl group, preferably substituted with 3 alkyl groups or 3 aryl groups. Examples of “substituted or unsubstituted silyl groups”, especially “substituted or unsubstituted C1 to C25 silyl groups”, may include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, etc.

[0026] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornene, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, 1-adamantane, or 2-adamantane.

[0027] The aryl group described in this invention refers to the general term for a monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this. The polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, tetraphenyl, etc., but not limited to this. The fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthrene, triphenylene, pyrene, perylene, fluoranyl, fluorene, benzo[a]fluorene, spiroanthracenefluorene, spirodifluorene, etc., but not limited to this.

[0028] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, pyrrolithyl, furanyl, thiopheneyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include spirofluorenoxanthyl, spirofluorenthixanthyl, acridinel, 9,10-dihydroacridinyl, naphridinyl, indolyl, phenoxazinyl Phenothiazinyl, phenoxathialyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, o-phenanthrolinel, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, benzothiopheneyl, benzothiazolyl, dibenzothiopheneyl, benzodibenzothiopheneyl, benzooxazolyl, dibenzooxazolyl, benzoimidazolyl, dibenzoimidazolyl, dibenzothiazolyl, carbazoleyl, benzocarbazoleyl, etc., but not limited to these.

[0029] The fused alicyclic and aromatic cyclic group described in this invention refers to a monovalent group formed by removing one hydrogen atom after the alicyclic and aromatic rings are fused together. Preferably, it has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 13 carbon atoms, such as benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropyl, naphthocyclobutyl, naphthocyclopentyl, naphthocyclohexyl, etc., but is not limited thereto.

[0030] The fused cyclic group of alicyclic and heteroaromatic rings mentioned in this invention refers to a monovalent group formed by removing a hydrogen atom after the alicyclic and heteroaromatic rings are fused together. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms, such as pyridocyclopropyl, pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridinium benzocycloheptyl, pyrimidinium cyclopropyl, pyrimidinium cyclobutyl, pyrimidinium cyclopentyl, pyrimidinium benzocycloheptyl, carbazole cyclopropyl, carbazole cyclobutyl, carbazole cyclopentyl, carbazole cyclohexyl, carbazole cycloheptyl, dibenzofuran cyclopropyl, dibenzofuran cyclobutyl, dibenzofuran cyclopentyl, dibenzofuran cyclohexyl, dibenzofuran cycloheptyl, dibenzothiophene cyclopropyl, dibenzothiophene cyclobutyl, dibenzothiophene cyclopentyl, dibenzothiophene cyclohexyl, dibenzothiophene cycloheptyl, etc., but not limited thereto.

[0031] The arylene group described in this invention refers to an aryl group with two bonding sites, i.e., a divalent group. The above description of aryl groups can be applied to it, the difference being that the arylene group is a divalent group.

[0032] In this invention, a heteroaryl group refers to a heteroaryl group with two bonding sites, i.e., a divalent group. The above description of heteroaryl groups can be applied to it, the difference being that the heteroaryl group is a divalent group.

[0033] The fused alicyclic and aromatic ring groups described in this invention refer to the divalent groups formed by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. The above description of fused alicyclic and aromatic ring groups can be applied to them, the difference being that the fused alicyclic and aromatic ring groups are divalent groups.

[0034] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0035] In this invention, "substituted or unsubstituted" means either unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkylboron, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C6-C60 arylamine, substituted or unsubstituted C6-C60 aryl... The alkyl group is boryl or silyl, preferably deuterium, tritium, halogen, cyano, C1-C12 alkyl, C3-C12 cycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or silyl. When substituted with multiple substituents, the substituents may be the same or different from each other. Preferably, it means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, propyl, butyl, deuterated butyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or deuterium. tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated cyclobutane, cyclopentane, methyl-substituted cyclopentane, ethyl-substituted cyclopentane, deuterated cyclopentane, cyclohexane, methyl-substituted cyclohexane, ethyl-substituted cyclohexane, n-propyl-substituted cyclohexane, n-butyl-substituted cyclohexane, cyclohexane-substituted cyclohexane, deuterated cyclohexane, cycloheptane, adamantane, methyl-substituted adamantane, ethyl-substituted adamantane, deuterated adamantane, norbornyl, methyl-substituted norbornyl Ethyl-substituted norbornel, deuterated norbornel, tetrahydropyrrolyl, piperidinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracel, deuterated anthracel, phenanthryl, deuterated phenanthryl, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, triphenylsilyl, where the multiple substituents are the same or different from each other when substituted by multiple substituents.

[0036] In this invention, when the position of the substituent on the aromatic ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the aromatic ring. For example, Can represent Can represent Can represent And so on.

[0037] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent Can represent And so on.

[0038] In this invention, "adjacent groups linked together to form a substituted or unsubstituted ring" refers to the formation of a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle by the combination of adjacent groups and optional aromatization. The "adjacent groups" refer to two substituents on two directly connected atoms, a substituent positioned spatially closest to the corresponding substituent, or another substituent on an atom with a corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an aliphatic ring can be considered "adjacent" to each other. The aliphatic ring and the aliphatic heterocycle can be saturated or unsaturated rings. Specifically, the rings formed can be three-membered, four-membered, five-membered, six-membered, seven-membered, spirocyclic, or fused rings. The aromatic ring formed preferably has 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The heteroaromatic ring formed preferably has 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The aliphatic ring formed preferably has 3 to 30 carbon atoms, particularly preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The aliphatic heterocycle formed preferably has 3 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, more preferably 2 to 12 carbon atoms, and most preferably 2 to 7 carbon atoms. Furthermore, the rings formed by the connection can be, for example, benzene, naphthalene, indene, cyclopentane, cyclopentanophenene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but are not limited to these.

[0039]

[0040] This invention provides a triamine compound, as shown in Formula I.

[0041]

[0042] R1 is independently selected from any one of deuterium, cyano, fluorine, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl;

[0043] The a0 is selected from 1, 2, or 3;

[0044] The Ar1 is selected from the group shown in formula a;

[0045] The Ar2 is selected from the group shown in formula a or formula b;

[0046] X and Y are independently selected from O or S;

[0047] The z and v are independently selected from CH or N;

[0048] The R2 and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent R2 or adjacent R3 are bonded to each other to form a substituted or unsubstituted ring;

[0049] The n1 is selected from 0, 1, 2, 3, 4 or 5;

[0050] The m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7;

[0051] The Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups.

[0052] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring in a fused cycloalcoholic group, or a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroarylene ring in a fused cycloalcoholic group.

[0053] Preferably, the triamine compound is selected from any one of the structures shown in Formula I-1 to Formula I-5:

[0054]

[0055] Preferably, R1 is independently selected from deuterium, cyano, fluorine, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, Dibenzothiophene, benzofuranopyridyl, benzothiophene-pyridyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridinooxazolyl, pyridinothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl.

[0056] Preferably, when R1 is selected from deuterium, a0 is selected from 3; when R1 is selected from fluorine, a0 is selected from 3.

[0057] Preferably, when R1 is selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazolyl, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl, pyridothiophene, dibenzofuranyl, dibenzothiophene, benzofuranopyridyl, benzothiophene-pyridyl, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzooxazolyl, benzothiazolyl, pyridooxazolyl, pyridothiazolyl, a0 is selected from 1.

[0058] Preferably, formula a is selected from any one of the following groups:

[0059]

[0060]

[0061] The R2 is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl , pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R2 groups bonded together to form substituted or unsubstituted rings;

[0062] The n1 is selected from 0, 1, 2, 3, 4 or 5; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2 or 3; the n4 is selected from 0, 1 or 2; the n5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6; the n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; and the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0063] More preferably, formula a is selected from any one of the following groups:

[0064]

[0065] Preferably, formula b is selected from any one of the following groups:

[0066]

[0067]

[0068] Y1 is selected from O, S or C(RsRt);

[0069] The R3 is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl Pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R3s bonded together to form substituted or unsubstituted rings;

[0070] The Rs and Rt are independently selected from hydrogen, deuterium, cyano, halogen, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl Benzothiophene, pyridofuran, pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl;

[0071] The m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3 or 4; the m5 is selected from 0, 1, 2 or 3; the m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0072] More preferably, formula b is selected from any one of the following groups:

[0073]

[0074] Preferably, the Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following groups:

[0075]

[0076]

[0077]

[0078]

[0079] The Rd is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl , pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rds bonded together to form substituted or unsubstituted rings;

[0080] The Re and Rf groups are independently selected from hydrogen, deuterium, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzene Thiopheneyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, benzofuranopyridine, benzothienopyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl;

[0081] The q1 is selected from 0, 1, 2, 3, 4 or 5; the q2 is selected from 0, 1, 2, 3 or 4; the q3 is selected from 0, 1, 2 or 3; the q4 is selected from 0, 1 or 2; the q5 is selected from 0, 1, 2, 3, 4, 5 or 6; the q6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the q7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the q9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0082] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one or a combination of the following groups:

[0083]

[0084] The u is independently selected from CH or N;

[0085] The V is selected from O, S, or N (Rh);

[0086] The ring W is selected from substituted or unsubstituted C3 to C30 alicyclic rings;

[0087] The Rm is independently selected from any one of deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl ring, or adjacent Rm are bonded to each other to form a substituted or unsubstituted ring;

[0088] The Rp and Rq are independently selected from any one of deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent Rp and Rq can be connected to each other to form substituted or unsubstituted rings;

[0089] The Rh is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl;

[0090] p1 is selected from 0, 1, 2, 3 or 4; p2 is selected from 0, 1, 2 or 3; p3 is selected from 0, 1 or 2; p4 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0091] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or any one or a combination of the following groups:

[0092]

[0093]

[0094] The Rm is independently selected from hydrogen, deuterium, cyano, fluorine, chlorine, bromine, iodine, or selected from any one of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridoxuryl yl, pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rm groups bonded together to form substituted or unsubstituted rings;

[0095] The Rh is selected from hydrogen, deuterium, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene. Pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, benzofuranopyridine, benzothienopyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl;

[0096] p5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; p6 is selected from 0, 1, 2, 3, 4 or 5.

[0097] The triamine compound is selected from any one of the following compounds:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] The above only lists some specific structural forms of triamine compounds represented by Formula I. However, this invention is not limited to these chemical structures. Any compound based on Formula I with substituents as defined in this invention should be included.

[0138] The triamine compounds represented by Formula I in this invention can be prepared via the following synthetic route:

[0139] when and When they are the same,

[0140]

[0141] when and When they are the same,

[0142]

[0143] when and When they are the same,

[0144]

[0145] The main reaction type involved in this invention is the Buchwald coupling reaction. The raw materials in the synthetic route provided by this invention can be commercially available products or prepared by methods known in the art.

[0146] X1, X2, X3, and X4 are independently selected from I, Br, or Cl; the limitations of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, and a0 are the same as those described above.

[0147] Alternatively, the order of the above reactions can be changed to obtain the triamine compound represented by Formula I of the present invention.

[0148] The above reaction routes all employ reaction types commonly used in organic synthesis, and there are no particular restrictions on reaction conditions (e.g., the selection, amount, order, and method of addition of reaction solvents, catalysts, ligands, bases, etc.). The above preparation methods utilize readily available raw materials, have simple processes, and yield excellent results. The compounds represented by Formula I provided by this invention can also be synthesized using other conventional reaction types in organic synthesis without particular limitations; the above are merely examples of synthetic routes.

[0149] The present invention provides an organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, and the organic functional layer comprises any one or more of the triamine compounds described in the present invention.

[0150] Preferably, the organic functional layer includes a hole transport region, a light-emitting layer, and an electron transport region. The hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the cathode and the light-emitting layer. The hole transport region contains any one or more of the triamine compounds described in this invention.

[0151] Preferably, the hole transport region includes a hole transport layer, and the hole transport layer contains any one or more of the triamine compounds described in this invention.

[0152] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer and / or the second hole transport layer contains any one or more of the triamine compounds described in this invention.

[0153] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the first hole transport layer contains any one or more of the triamine compounds described in this invention.

[0154] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, wherein the second hole transport layer contains any one or more of the triamine compounds described in this invention.

[0155] Preferably, the organic functional layer is located outside either the anode or the cathode, and the organic functional layer includes a capping layer containing any one or more of the triamine compounds described in this invention.

[0156] Preferably, the organic functional layer includes an anode, a cathode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer. The first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the anode and the cathode. The charge-generating layer is located between the first light-emitting unit and the second light-emitting unit. The charge-generating layer contains any one or more of the triamine compounds described in this invention.

[0157] Preferably, the charge generation layer includes a P-type charge generation layer and an N-type charge generation layer, wherein the P-type charge generation layer comprises any one or more of the triamine compounds described in this invention.

[0158] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0159] The anode of this invention needs to have a high work function in order to improve hole injection efficiency. The anode material can be selected from materials such as metal oxides, combinations of metals and oxides, metals or their alloys. Specific examples may include indium tin oxide (ITO), indium zinc oxide (IZO), aluminum (Al), titanium (Ti), gold (Au), platinum (Pt), copper (Cu), silver (Ag), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), etc., but are not limited to these.

[0160] The cathode of this invention needs to have a low work function in order to improve electron injection efficiency. The cathode material can be selected from materials such as metals or their alloys. Specific examples may include aluminum (Al), silver (Ag), calcium (Ca), indium (In), magnesium:silver (Mg:Ag), etc., but are not limited to these.

[0161] The hole injection layer material of this invention needs to have good hole injection capability and a suitable HOMO energy level, which can effectively reduce the interfacial barrier between the anode and the hole transport layer and improve the hole injection capability. The hole injection layer material can be selected from the following materials: aromatic amine derivatives, metal oxides, phthalocyanine metal complexes, polycyano conjugated organic compounds, polymers, etc. Specific examples may include N,N'-bis[4-di(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-hexaazabenzonitrile (HAT-CN), poly(4-vinyltriphenylamine) (PVTPA), vanadium pentoxide (V2O5), etc., but are not limited to these.

[0162] The hole transport layer material of this invention needs to have a high hole mobility to facilitate hole injection. The hole transport layer material can be selected from aromatic amine derivatives, carbazole derivatives, fluorene derivatives, polymers, etc. Specific examples may include, but are not limited to, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(2-naphthyl)-1,1'-biphenyl-4,4'-diamine (β-NPB), N,N,N',N'-tetra-1-naphthyl[1,1'-biphenyl]-4,4'-diamine (α-TNB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC), and 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA). Triamine compounds described in this invention are preferred.

[0163] The electron blocking layer of the present invention is preferably made of a material with good hole transport capability and electron blocking capability. Electron blocking materials include, but are not limited to, aromatic amine derivatives, carbazole derivatives, etc. Specific examples of the electron blocking material may include, but are not limited to, N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), N,N-bis([1,1'-biphenyl]-4-)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, etc. Triamine compounds of the present invention are preferred.

[0164] The luminescent layer material of this invention typically contains a guest (doped) material and a host material. The guest material can be a simple fluorescent material, phosphorescent material, or TADF material, or a combination of fluorescent and phosphorescent materials. The host material of the luminescent layer not only needs to possess bipolar charge transport properties but also needs appropriate energy levels to effectively transfer excitation energy to the guest luminescent material. Examples of such materials include carbazole derivatives, stilbene aryl derivatives, stilbene derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives. Specific examples may include 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CZSi), 9,9'-diphenyl-9H,9'H-3,3'-bicarbazole (BCzPh), and 9-(5-(3-(9H-carbazole-9-yl)phenyl)pyridine-3- 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazolyl)benzene (MCP), tris(6-fluoro-8-hydroxyquinoline)aluminum (6FAlq3), tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), bis(8-hydroxyquinoline)zinc (Znq2), but not limited to these.

[0165] The guest material may be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but not limited to these. Specific examples may include bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium (Ir(npy)2acac), tris[2-(3-methyl-2-pyridyl)phenyl]iridium (Ir(3mppy)3), bis(2-benzo[H]quinoline-C2,N')(acetylacetone)iridium (Ir(bzq)2(acac)), 2,5,8,11-tetra-tert-butylperylene (TBPe), rubrene, 9-(9-phenylcarbazole-3-yl)-10-(naphthyl-1-yl) (PCAN), 1,4-bis(4-(9H-carbazole-9-yl)styryl)benzene (BCzSB), but not limited to these.

[0166] The hole-blocking layer of this invention needs to have good electron transport capability and hole blocking capability, effectively transporting electrons and restricting the escape of holes to the light-emitting layer interface. The hole-blocking layer material includes, but is not limited to, the following materials: metal complexes, quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azirbenzene derivatives, etc. Specific examples may include 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine (TmPyPB), etc., but is not limited to these.

[0167] The electron transport material of this invention needs to have a high electron mobility to facilitate electron injection. The electron transport layer material includes, but is not limited to, the following: quinoline derivatives, imidazole derivatives, o-phenanthroline derivatives, triazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, etc. Specific examples may include, but are not limited to, aluminum 8-hydroxyquinoline (Alq3), zinc (II) bis(8-hydroxyquinoline) (Znq), 2,9-bis(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 3,3,5,5-tetra[m-pyridyl]-phenyl-3-yl]biphenyl (BP4mPy), 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-phenyl)-1-phenyl)-1H-phenanthrene[9,10-d]imidazole (ADN-PAimi), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), and 4,4'-bis(4,6-diphenyl-1,3,5-triazin-2-yl)biphenyl (BTB).

[0168] The electron injection material of this invention needs to have good electron injection capability and a suitable LUMO energy level in order to reduce the interface barrier between the cathode and the electron transport layer and improve the electron injection capability. The electron injection layer material includes, but is not limited to, the following materials: ytterbium (Yb), lithium fluoride (LiF), magnesium fluoride (MgF), lithium 8-hydroxyquinoline (LiQ), cesium carbonate (Cs₂CO₃), rubidium acetate (CH₃COORb), lithium oxide (Li₂O), etc.

[0169] The P-type charge-generating layer material of this invention may comprise one of the following materials or combinations thereof: N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HATCN), etc. In addition to the above materials, the P-type charge-generating material may also comprise doped materials, specific examples of which may include vanadium pentoxide (V₂O₅), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F₄-TCNQ), etc., but are not limited thereto. Preferably, the triamine compound of this invention is preferred.

[0170] The capping layer of this invention serves to couple light trapped within a device. The capping layer material includes, but is not limited to, the following: metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Specific examples may include, but are not limited to, aluminum tris(8-hydroxyquinoline)aluminum (Alq3), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), 4,4'-di(9-carbazole)biphenyl (CBP), etc. Triamine compounds of this invention are preferred.

[0171] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc. can be used, but it is not limited to these methods.

[0172] The organic electroluminescent device provided by this invention can be applied to lighting and display fields, specifically including smartphone displays, tablet displays, smart wearable device displays, large-size displays such as televisions, VR, and car taillights.

[0173] The technical solutions and effects of the present invention will be further described below with reference to embodiments and comparative examples.

[0174] The mass spectrometry of the compounds in this invention was performed using a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer from Waters Instruments, UK, with chloroform as the solvent.

[0175] Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0176] Synthesis Example 1: Preparation of Compound 2

[0177]

[0178] Preparation of intermediate B-2:

[0179] Under nitrogen protection, toluene (800 mL), a-2 (18.84 g, 120.00 mmol), b-2 (20.31 g, 120.00 mmol), Pd(dppf)Cl2 (1.05 g, 1.44 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and then refluxed for 8.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate B-2 (24.43 g, 83% yield), with a solid purity ≥99.89% as determined by HPLC. Mass spectrometry m / z: 245.1215 (theoretical value: 245.1204).

[0180] Preparation of intermediate D-2:

[0181] Under nitrogen protection, toluene (320 mL), c-2 (9.88 g, 40.00 mmol), d-2 (5.33 g, 40.00 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), and tri-tert-butylphosphine (1.60 mL, 0.80 mmol, in 0.5 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred to dissolve and refluxed for 3.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (5:1 v / v) yielded intermediate D-2 (9.58 g, 80% yield), with a solid purity ≥99.86% as determined by HPLC. Mass spectrometry m / z: 299.0959 (theoretical value: 299.0946).

[0182] Preparation of intermediate C-2:

[0183] Under nitrogen protection, toluene (640 mL), A-2 (10.93 g, 40.00 mmol), B-2 (19.63 g, 80.00 mmol), Pd(OAc)2 (0.22 g, 0.96 mmol), sodium tert-butoxide (7.69 g, 80.00 mmol), and tri-tert-butylphosphine (1.60 mL, 0.80 mmol, in 0.5 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred to dissolve and refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (6:1 v / v) to give intermediate C-2 (18.07 g, 75% yield). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 601.2374 (theoretical value: 601.2364).

[0184] Preparation of compound 2:

[0185] Under nitrogen protection, toluene (240 mL), C-2 (14.45 g, 24.00 mmol), D-2 (7.18 g, 24.00 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol), sodium tert-butoxide (4.61 g, 48.00 mmol), and X-Phos (0.23 g, 0.48 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and the mixture was refluxed for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 2 (14.95 g, 72% yield), with a solid purity ≥99.97% as determined by HPLC. Mass spectrometry m / z: 864.3556 (theoretical value: 864.3544). Theoretical elemental content (%) C 62 H 40 D3N3O2: C, 86.08; H, 5.36; N, 4.86. Measured elemental content (%): C, 86.07; H, 5.40; N, 4.82.

[0186] Synthesis Example 2: Preparation of Compound 28

[0187]

[0188] Following the same preparation method as in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-28 to obtain compound 28 (12.67 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 722.3556 (theoretical value: 722.3545). Theoretical elemental content (%) C 50 H 22 D 13N3O2: C, 83.07; H, 6.69; N, 5.81. Measured elemental content (%): C, 83.12; H, 6.64; N, 5.83.

[0189] Synthesis Example 3: Preparation of Compound 99

[0190]

[0191] Following the same preparation method as in Synthesis Example 1, b-2 was replaced with an equimolar amount of b-99 to obtain compound 99 (16.22 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 964.3877 (theoretical value: 964.3857). Theoretical elemental content (%) C 70 H 44 D3N3O2: C, 87.11; H, 5.22; N, 4.35. Measured elemental content (%): C, 87.13; H, 5.25; N, 4.34.

[0192] Synthesis Example 4: Preparation of Compound 163

[0193]

[0194] Following the same preparation method as in Synthesis Example 1, c-2, d-2, and B-2 were replaced with equimolar amounts of a-2, d-163, and D-2, respectively, to obtain compound 163 (14.36 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 842.2983 (theoretical value: 842.2972). Theoretical elemental composition (%) C58H34D3N3O4: C, 82.64; H, 4.78; N, 4.98. Measured elemental composition (%): C, 82.65; H, 4.82; N, 4.97.

[0195] Synthesis Example 5: Preparation of Compound 174

[0196]

[0197] Following the same preparation method as in Synthesis Example 1, a-2, b-2, c-2, and d-2 were replaced with equimolar amounts of c-2, b-174, a-2, and d-174 to obtain compound 174 (15.10 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 898.3608 (theoretical value: 898.3598). Theoretical elemental content (%) C 62 H 42 D3N3O4: C, 82.83; H, 5.38; N, 4.67. Measured elemental content (%): C, 82.86; H, 5.37; N, 4.71.

[0198] Synthesis Example 6: Preparation of Compound 238

[0199]

[0200] Following the same preparation method as in Synthesis Example 1, b-2 and A-2 were replaced with equimolar amounts of b-238 and A-238, respectively, to obtain compound 238 (15.21 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 867.3689 (theoretical value: 867.3676). Theoretical elemental content (%) C 57 H 53 N3O2S i2 C, 78.85; H, 6.15; N, 4.84. Measured elemental content (%): C, 78.89; H, 6.14; N, 4.88.

[0201] Synthesis Example 7: Preparation of Compound 254

[0202]

[0203] Following the same preparation method as in Synthesis Example 1, b-2 and A-2 were replaced with equimolar amounts of b-254 and A-238, respectively, to obtain compound 254 (16.06 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 955.4150 (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, 86.70; H, 5.57; N, 4.35.

[0204] Synthesis Example 8: Preparation of Compound 272

[0205]

[0206] Following the same preparation method as in Synthesis Example 1, a-2, A-2, and D-2 were replaced with equimolar amounts of a-272, A-272, and B-174, respectively, to obtain compound 272 (17.76 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 1041.4288 (theoretical value: 1041.4294). Theoretical elemental content (%) C 76 H 55 N3O2: C, 87.58; H, 5.32; N, 4.03. Measured elemental content (%): C, 87.57; H, 5.36; N, 4.08.

[0207] Synthesis Example 9: Preparation of Compound 297

[0208]

[0209] Following the same preparation method as in Synthesis Example 1, b-2, A-2, and D-2 were replaced with equimolar amounts of b-297, A-238, and B-174, respectively, to obtain compound 297 (15.19 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 903.3079 (theoretical value: 903.3097). Theoretical elemental content (%) C 63 H 41 N3O4: C, 83.70; H, 4.57; N, 4.65. Measured elemental content (%): C, 83.73; H, 4.55; N, 4.70.

[0210] Synthesis Example 10: Preparation of Compound 325

[0211]

[0212] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of a-2, d-325, A-238, and D-2, respectively, to obtain compound 325 (14.97 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 903.3090 (theoretical value: 903.3097). Theoretical elemental content (%) C 63 H 41 N3O4: C, 83.70; H, 4.57; N, 4.65. Measured elemental content (%): C, 83.75; H, 4.54; N, 4.71.

[0213] Synthesis Example 11: Preparation of Compound 329

[0214]

[0215] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of a-2, d-329, A-238, and D-2, respectively, to obtain compound 329 (14.81 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 893.3250 (theoretical value: 893.3254). Theoretical elemental content (%) C 62 H 43 N3O4: C, 83.29; H, 4.85; N, 4.70. Measured elemental content (%): C, 83.33; H, 4.82; N, 4.76.

[0216] Synthesis Example 12: Preparation of Compound 373

[0217]

[0218] Preparation of intermediate B-373:

[0219] Under nitrogen protection, toluene (800 mL), c-373 (29.65 g, 120.00 mmol), b-373 (15.98 g, 120.00 mmol), Pd(dppf)Cl2 (1.05 g, 1.44 mmol), and sodium tert-butoxide (17.30 g, 180.00 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and then refluxed for 8.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate B-373 (28.74 g, 80% yield), with a solid purity ≥99.89% as determined by HPLC. Mass spectrometry m / z: 299.0961 (theoretical value: 299.0946).

[0220] Preparation of compound 373

[0221] Under nitrogen protection, toluene (384 mL), A-373 (5.36 g, 24.00 mmol), B-373 (21.55 g, 72.00 mmol), Pd(OAc)₂ (0.13 g, 0.576 mmol), sodium tert-butoxide (4.62 g, 48.00 mmol), and tri-tert-butylphosphine (0.96 mL, 0.48 mmol, in 0.5 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred to dissolve and refluxed for 9 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (5:1 v / v) to give compound 373 (17.25 g, 71% yield). The solid purity was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 1011.3319 (theoretical value: 1011.3308). Theoretical elemental content (%) C 69 H 45 N3O6: C, 81.88; H, 4.48; N, 4.15. Measured elemental content (%): C, 81.85; H, 4.45; N, 4.19.

[0222] Synthesis Example 13: Preparation of Compound 401

[0223]

[0224] Preparation of intermediate D-401:

[0225] Under nitrogen protection, toluene (320 mL), c-401 (9.88 g, 40.00 mmol), b-174 (5.33 g, 40.00 mmol), Pd(OAc)₂ (0.09 g, 0.40 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), and tri-tert-butylphosphine (1.60 mL, 0.80 mmol, in 0.5 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred to dissolve and refluxed for 3.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (5:1 v / v) yielded intermediate D-401 (12.49 g, 80% yield), with a solid purity ≥99.83% as determined by HPLC. Mass spectrometry m / z: 389.0730 (theoretical value: 389.0738).

[0226] Preparation of intermediate C-401:

[0227] Under nitrogen protection, toluene (640 mL), A-401 (12.08 g, 40.00 mmol), D-163 (6.77 g, 40.00 mmol), Pd(OAc)2 (0.22 g, 0.96 mmol), sodium tert-butoxide (7.69 g, 80.00 mmol), and tri-tert-butylphosphine (1.60 mL, 0.80 mmol, in 0.5 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred to dissolve and refluxed for 3 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (6:1 v / v) to give intermediate C-401 (11.40 g, 73% yield). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 389.0754 (theoretical value: 389.0738).

[0228] Preparation of compound 401:

[0229] Under nitrogen protection, toluene (240 mL), C-401 (9.37 g, 24.00 mmol), D-401 (14.37 g, 48.00 mmol), Pd2(dba)3 (0.22 g, 0.24 mmol), sodium tert-butoxide (4.61 g, 48.00 mmol), and X-Phos (0.23 g, 0.48 mmol) were added sequentially to a reaction flask. The mixture was stirred until dissolved, and the mixture was refluxed for 4.5 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 401 (15.39 g, 70% yield), with a solid purity ≥99.95% as determined by HPLC. Mass spectrometry m / z: 915.3090 (theoretical value: 915.3097). Theoretical elemental content (%) C 64 H 41 N3O4: C, 83.92; H, 4.51; N, 4.59. Measured elemental content (%): C, 83.94; H, 4.54; N, 4.55.

[0230] Synthetic Example 14: Preparation of Compound 415

[0231]

[0232] Following the same preparation method as in Synthesis Example 12, A-373 and B-373 were replaced with equimolar amounts of A-415 and D-2, respectively, to obtain compound 415 (16.96 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 1023.2540 (theoretical value: 1023.2556). Theoretical elemental content (%) C 66 H 36 F3N3O6: C, 77.41; H, 3.54; N, 4.10. Measured elemental content (%): C, 77.45; H, 3.50; N, 4.16.

[0233] Synthesis Example 15: Preparation of Compound 431

[0234]

[0235] Following the same preparation method as in Synthesis Example 1, c-2, b-2, and B-2 were replaced with equimolar amounts of c-431, d-431, and D-163, respectively, to obtain compound 431 (14.53 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 864.3555 (theoretical value: 864.3544). Theoretical elemental content (%) C 62 H 40D3N3O2: C, 86.08; H, 5.36; N, 4.86. Measured elemental content (%): C, 86.06; H, 5.40; N, 4.85.

[0236] Synthetic Example 16: Preparation of Compound 436

[0237]

[0238] Following the same preparation method as in Synthesis Example 1, c-2, d-2, and B-2 were replaced with equimolar amounts of c-436, d-436, and D-163, respectively, to obtain compound 431 (16.60 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 1016.4178 (theoretical value: 1016.4170). Theoretical elemental content (%) C 74 H 48 D3N3O2: C, 87.37; H, 5.35; N, 4.13. Measured elemental content (%): C, 87.35; H, 5.40; N, 4.10.

[0239] Synthesis Example 17: Preparation of Compound 441

[0240]

[0241] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of c-441, d-441, A-272, and D-163, respectively, to obtain compound 441 (15.30 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 897.4179 (theoretical value: 897.4170). Theoretical elemental content (%) C 64 H 39 D8N3O2: C, 85.59; H, 6.17; N, 4.68. Measured elemental content (%): C, 85.57; H, 6.20; N, 4.64.

[0242] Synthetic Example 18: Preparation of Compound 446

[0243]

[0244] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of a-446, d-2, and D-163, respectively, to obtain compound 446 (14.40 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 856.3859 (theoretical value: 856.3851). Theoretical elemental content (%) C 58 H 20 D 17N3O4: C, 81.28; H, 6.35; N, 4.90. Measured elemental content (%): C, 81.24; H, 6.37; N, 4.94.

[0245] Synthetic Example 19: Preparation of Compound 454

[0246]

[0247] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of a-454, d-2, and D-163, respectively, to obtain compound 454 (16.28 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 954.4232 (theoretical value: 954.4224). Theoretical elemental content (%) C 66 H 50 D3N3O4: C, 82.99; H, 5.91; N, 4.40. Measured elemental content (%): C, 82.96; H, 5.97; N, 4.44.

[0248] Synthesis Example 20: Preparation of Compound 458

[0249]

[0250] Following the same preparation method as in Synthesis Example 1, c-2 and A-2 were replaced with equimolar amounts of c-458 and A-238, respectively, to obtain compound 458 (16.45 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 951.3810 (theoretical value: 951.3825). Theoretical elemental content (%) C 69 H 49 N3O2: C, 87.04; H, 5.19; N, 4.41. Measured elemental content (%): C, 87.10; H, 5.15; N, 4.44.

[0251] Synthesis Example 21: Preparation of Compound 470

[0252]

[0253] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of a-470, b-470, and D-163, respectively, to obtain compound 470 (14.23 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 846.2790 (theoretical value: 846.2782). Theoretical elemental content (%) C 54 H 30D3N7O4: C, 76.58; H, 4.28; N, 11.58. Measured elemental content (%): C, 76.60; H, 4.32; N, 11.54.

[0254] Synthesis Example 22: Preparation of Compound 474

[0255]

[0256] Following the same preparation method as in Synthesis Example 1, c-2 and d-2 were replaced with equimolar amounts of c-474 and d-474, respectively, to obtain compound 474 (15.15 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 914.3709 (theoretical value: 914.3700). Theoretical elemental content (%) C 66 H 42 D3N3O2: C, 86.63; H, 5.29; N, 4.59. Measured elemental content (%): C, 86.60; H, 5.24; N, 4.57.

[0257] Synthesis Example 23: Preparation of Compound 479

[0258]

[0259] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of a-479, d-2, and D-163, respectively, to obtain compound 479 (16.70 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 1022.3193 (theoretical value: 1022.3184). Theoretical elemental content (%) C 70 H 38 D3N3O6: C, 82.18; H, 4.33; N, 4.11. Measured elemental content (%): C, 82.24; H, 4.31; N, 4.15.

[0260] Synthesis Example 24: Preparation of Compound 497

[0261]

[0262] Following the same preparation method as in Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-497 and c-497, respectively, to obtain compound 497 (12.10 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 690.3083 (theoretical value: 690.3074). Theoretical elemental content (%) C 48 H 34D3N3O2: C, 83.45; H, 5.84; N, 6.08. Measured elemental content (%): C, 83.44; H, 5.90; N, 6.12.

[0263] Synthesis Example 25: Preparation of Compound 513

[0264]

[0265] Following the same preparation method as in Synthesis Example 1, b-2, c-2, and d-2 were replaced with equimolar amounts of b-513, c-513, and b-174, respectively, to obtain compound 513 (12.58 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 770.3720 (theoretical value: 770.3700). Theoretical elemental content (%) C 54 H 42 D3N3O2: C, 84.12; H, 6.27; N, 5.45. Measured elemental content (%): C, 84.14; H, 6.26; N, 5.48.

[0266] Synthesis Example 26: Preparation of Compound 567

[0267]

[0268] Following the same preparation method as in Synthesis Example 1, b-2, A-2, and D-2 were replaced with equimolar amounts of b-567, A-238, and D-497, respectively, to obtain compound 567 (14.25 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 835.3994 (theoretical value: 835.3983). Theoretical elemental content (%) C 59 H 33 D 10 N3O2: C, 84.76; H, 6.39; N, 5.03. Measured elemental content (%): C, 84.81; H, 6.36; N, 5.09.

[0269] Synthesis Example 27: Preparation of Compound 601

[0270]

[0271] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of a-2, d-601, A-238, and D-497, respectively, to obtain compound 601 (14.78 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 879.3090 (theoretical value: 879.3097). Theoretical elemental content (%) C 61 H 41N3O4: C, 83.26; H, 4.70; N, 4.78. Measured elemental content (%): C, 83.29; H, 4.74; N, 4.76.

[0272] Synthesis Example 28: Preparation of Compound 610

[0273]

[0274] Following the same preparation method as in Synthesis Example 1, A-2 and D-2 were replaced with equimolar amounts of A-441 and D-497, respectively, to obtain compound 610 (14.92 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 839.3525 (theoretical value: 839.3512). Theoretical elemental content (%) C 60 H 45 N3O2: C, 85.79; H, 5.40; N, 5.00. Measured elemental content (%): C, 85.78; H, 5.46; N, 5.05.

[0275] Synthesis Example 29: Preparation of Compound 674

[0276]

[0277] Following the same preparation method as in Synthesis Example 12, B-373 was replaced with an equimolar amount of B-674 to obtain compound 674 (14.27 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 861.2859 (theoretical value: 861.2839). Theoretical elemental content (%) C 57 H 39 N3O6: C, 79.43; H, 4.56; N, 4.88. Measured elemental content (%): C, 79.48; H, 4.51; N, 4.86.

[0278] Synthesis Example 30: Preparation of Compound 741

[0279]

[0280] Following the same preparation method as in Synthesis Example 1, b-2 and c-2 were replaced with equimolar amounts of b-741 and c-741, respectively, to obtain compound 741 (20.63 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 1244.4431 (theoretical value: 1244.4419). Theoretical elemental content (%) C 86 H 60 D3N3OSSi2: C, 82.92; H, 5.34; N, 3.37. Measured elemental content (%): C, 82.90; H, 5.36; N, 3.34.

[0281] Synthesis Example 31: Preparation of Compound 786

[0282]

[0283] Following the same preparation method as in Synthesis Example 1, A-2, B-2, and D-2 were replaced with equimolar amounts of A-786, D-163, and D-741, respectively, to obtain compound 786 (12.96 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 739.2650 (theoretical value: 739.2657). Theoretical elemental content (%) C 51 H 37 N3OS: C, 82.79; H, 5.04; N, 5.68. Measured elemental content (%): C, 82.76; H, 5.06; N, 5.65.

[0284] Synthesis Example 32: Preparation of Compound 809

[0285]

[0286] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of a-2, d-809, A-238, and D-741, respectively, to obtain compound 809 (16.40 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 961.2789 (theoretical value: 961.2797). Theoretical elemental content (%) C 65 H 43 N3O2S2: C, 81.14; H, 4.50; N, 4.37. Measured elemental content (%): C, 81.18; H, 4.53; N, 4.36.

[0287] Synthesis Example 33: Preparation of Compound 861

[0288]

[0289] Following the same preparation method as in Synthesis Example 1, a-2, b-2, A-2, and D-2 were replaced with equimolar amounts of a-861, b-861, A-238, and D-163, respectively, to obtain compound 861 (14.84 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 895.3120 (theoretical value: 895.3111). Theoretical elemental content (%) C 59 H 29 D 10 N3O2S2: C, 79.08; H, 5.51; N, 4.69. Measured elemental content (%): C, 79.06; H, 5.57; N, 4.66.

[0290] Synthesis Example 34: Preparation of Compound 871

[0291]

[0292] Following the same preparation method as in Synthesis Example 1, d-2 and B-2 were replaced with equimolar amounts of d-871 and D-163, respectively, to obtain compound 871 (12.95 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 728.2679 (theoretical value: 728.2689). Theoretical elemental content (%) C 50 H 32 D3N3OS: C, 82.39; H, 5.25; N, 5.76. Measured elemental content (%): C, 82.37; H, 5.28; N, 5.80.

[0293] Synthesis Example 35: Preparation of Compound 972

[0294]

[0295] Following the same preparation method as in Synthesis Example 12, b-373 and B-373 were replaced with equimolar amounts of b-972 and A-972, respectively, to obtain compound 972 (17.31 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 1059.2610 (theoretical value: 1059.2623). Theoretical elemental content (%) C 69 H 45 N3O3S3: C, 78.16; H, 4.28; N, 3.96. Measured elemental content (%): C, 78.11; H, 4.26; N, 3.93.

[0296] Synthesis Example 36: Preparation of Compound 1015

[0297]

[0298] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of d-2, b-1015, and D-163, respectively, to obtain compound 1015 (13.39 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 774.2215 (theoretical value: 774.2202). Theoretical elemental content (%) C 50 H 30 D3N3O2S2: C, 77.49; H, 4.68; N, 5.42. Measured elemental content (%): C, 77.52; H, 4.66; N, 5.47.

[0299] Synthesis Example 37: Preparation of Compound 1128

[0300]

[0301] Following the same preparation method as in Synthesis Example 1, a-2, b-2, and D-2 were replaced with equimolar amounts of c-861, d-871, and D-163, respectively, to obtain compound 1128 (15.46 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 906.2051 (theoretical value: 906.2059). Theoretical elemental content (%) C 58 H 34 D3N3S4: C, 76.79; H, 4.44; N, 4.63. Measured elemental content (%): C, 76.77; H, 4.46; N, 4.68.

[0302] Synthesis Example 38: Preparation of Compound 1256

[0303]

[0304] Following the same preparation method as in Synthesis Example 1, c-2, d-2, A-2, and B-2 were replaced with equimolar amounts of c-1256, d-871, A-272, and D-163, respectively, to obtain compound 1256 (12.44 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 719.2422 (theoretical value: 719.2429). Theoretical elemental content (%) C 48 H 37 N3S2: C, 80.08; H, 5.18; N, 5.84. Measured elemental content (%): C, 80.06; H, 5.20; N, 5.80.

[0305] Synthesis Example 39: Preparation of Compound 1280

[0306]

[0307] Following the same preparation method as in Synthesis Example 1, c-2 and A-2 were replaced with equimolar amounts of c-1280 and A-1280, respectively, to obtain compound 1280 (14.51 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 875.3524 (theoretical value: 875.3512). Theoretical elemental content (%) C 63 H 45 N3O2: C, 86.37; H, 5.18; N, 4.80. Measured elemental content (%): C, 86.39; H, 5.15; N, 4.84.

[0308] Synthesis Example 40: Preparation of Compound 1366

[0309]

[0310] Following the same preparation method as in Synthesis Example 1, a-2 and b-2 were replaced with equimolar amounts of a-1366 and b-297, respectively, to obtain compound 1366 (15.62 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 875.3524 (theoretical value: 875.3512). Theoretical elemental content (%) C 66 H 38 D3N3O4: C, 84.06; H, 4.70; N, 4.46. Measured elemental content (%): C, 84.09; H, 4.75; N, 4.48.

[0311] Device Examples

[0312] The organic materials used in the device fabrication examples were all purified by sublimation, with a purity of over 99.99%. The ITO glass substrates and ITO / Ag / ITO glass substrates used in the device fabrication examples were purchased commercially.

[0313] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer. The device prepared according to this invention was tested at atmospheric pressure and room temperature at a current density of 10 mA / cm². 2 The luminous efficiency and driving voltage were measured. Using McScience's M6000 OLED lifetime testing system, the lifetime (brightness decaying to 95% of initial brightness) of the device prepared in this invention was tested at atmospheric pressure and room temperature. The current density during the test was 10 mA / cm². 2 .

[0314] Device Example 1: Fabrication of a Green Organic Light Emitting Device

[0315] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone, and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0316] The following layers were deposited sequentially on the aforementioned ITO / Ag / ITO glass substrate: a. HI-1 as a hole injection layer, with a deposition thickness of 20 nm. b. Compound 2 as the first hole transport layer, with a deposition thickness of 80 nm. c. HT2-1 as the second hole transport layer, with a deposition thickness of 20 nm. d. GH-1 as the host material and GD-1 as the guest material (mass ratio 93:7), with a light-emitting layer thickness of 30 nm. e. ET-1 and Liq (mass ratio 1:1) as the electron transport layer, with a deposition thickness of 30 nm. f. LiF layer as the electron injection layer, with a deposition thickness of 1 nm. g. Mg and Ag with a mass ratio of 1:9, with a deposition thickness of 15 nm. h. CP-1 as the capping layer, with a deposition thickness of 80 nm.

[0317] Device Examples 2 to 40: Fabrication of Green Organic Light Emitting Devices

[0318] Organic electroluminescent devices were prepared by replacing compound 2 in Device Example 1 with compounds 28, 99, 163, 119, 163, 174, 238, 254, 272, 297, 325, 329, 373, 401, 415, 431, 436, 441, 446, 454, 458, 470, 474, 479, 497, 513, 567, 601, 610, 674, 741, 786, 809, 861, 871, 972, 1015, 1128, 1256, 1280, and 1366 as the first hole transport layer material, while maintaining the same fabrication process.

[0319] Comparative device examples 1-2:

[0320] Organic electroluminescent devices were prepared by replacing compound 2 in device example 1 with comparative compound 1 and comparative compound 2 as the first hole transport layer material, with the rest of the fabrication process being exactly the same.

[0321]

[0322] Table 1: Test data on the luminescence characteristics of organic electroluminescent devices prepared in Device Examples 1-40 and Comparative Device Examples 1-2

[0323]

[0324]

[0325] As shown in Table 1, the triamine compounds described in this invention, when used as the first hole transport layer material, exhibit high hole mobility and suitable triplet energy levels, which can effectively improve hole transport performance.

[0326] Device Example 41: Fabrication of a Green Organic Light Emitting Device

[0327] First, the ITO / Ag / ITO glass substrate is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone, and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0328] The following layers were deposited sequentially on the aforementioned ITO / Ag / ITO glass substrate: a. HI-2:HI-3 = 6:94 as a hole injection layer, with a deposition thickness of 25 nm. b. HT1-1 as the first hole transport layer, with a deposition thickness of 85 nm. c. Compound 2 as the second hole transport layer, with a deposition thickness of 25 nm. d. GH-1 as the host material and GD-2 as the guest material (mass ratio 93:7), with a light-emitting layer thickness of 40 nm. e. ET-1 and Liq (mass ratio 1:1) as an electron transport layer, with a deposition thickness of 30 nm. f. LiF layer as an electron injection layer, with a deposition thickness of 1 nm. g. Mg and Ag with a mass ratio of 1:9, with a deposition thickness of 15 nm. h. CP-1 as a capping layer, with a deposition thickness of 80 nm.

[0329] Device Examples 42–80: Fabrication of Green Organic Light Emitting Devices

[0330] Organic electroluminescent devices were prepared by replacing compound 2 in device example 41 with compounds 28, 99, 163, 119, 163, 174, 238, 254, 272, 297, 325, 329, 373, 401, 415, 431, 436, 441, 446, 454, 458, 470, 474, 479, 497, 513, 567, 601, 610, 674, 741, 786, 809, 861, 871, 972, 1015, 1128, 1256, 1280, and 1366 as the second hole transport layer material, while maintaining the same fabrication process.

[0331] Comparative device examples 3-4:

[0332] Organic electroluminescent devices were prepared by replacing compound 2 in device example 41 with comparative compounds 3 and 4 as the second hole transport layer material, while keeping the rest of the fabrication process exactly the same.

[0333]

[0334] Table 2: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 41-80 and Comparative Device Examples 3-4

[0335]

[0336]

[0337]

[0338] As shown in Table 2, when the triamine compound described in this invention is used as the second hole transport layer material, it has a lower driving voltage, higher luminous efficiency, and longer lifespan compared to the comparative device.

[0339] Device Example 81: Fabrication of a Blue Organic Light Emitting Device

[0340] First, the ITO / Ag / ITO is ultrasonically cleaned twice with deionized water for 20 minutes each time. Then, it is ultrasonically cleaned sequentially with isopropanol, acetone, and methanol for 20 minutes each. After that, it is exposed to ultraviolet light and ozone for 30 minutes. Finally, it is placed in a vacuum evaporation equipment for later use.

[0341] The following layers were deposited sequentially on the aforementioned ITO / Ag / ITO glass substrate: a. HT1-4 as a hole injection layer, with a deposition thickness of 15 nm. b. HT1-1 as the first hole transport layer, with a deposition thickness of 85 nm. c. HT2-2 as the second hole transport layer, with a deposition thickness of 20 nm. d. BH-1 as the host material and BD-1 as the guest material (mass ratio 97:3), with a light-emitting layer thickness of 35 nm. e. ET-2 and Liq (mass ratio 1:1) as the electron transport layer, with a deposition thickness of 30 nm. f. LiF layer as the electron injection layer, with a deposition thickness of 1 nm. g. Mg and Ag with a mass ratio of 1:9, with a deposition thickness of 15 nm. h. Compound 2 as the capping layer, with a deposition thickness of 80 nm.

[0342] Device Examples 82–120: Fabrication of Blue Organic Light Emitting Devices

[0343] Organic electroluminescent devices were prepared by replacing compound 2 in device example 81 with compounds 28, 99, 163, 119, 163, 174, 238, 254, 272, 297, 325, 329, 373, 401, 415, 431, 436, 441, 446, 454, 458, 470, 474, 479, 497, 513, 567, 601, 610, 674, 741, 786, 809, 861, 871, 972, 1015, 1128, 1256, 1280, and 1366 as the capping layer material, while maintaining the same fabrication process.

[0344] Comparative device examples 7-8:

[0345] Organic electroluminescent devices were prepared by replacing compound 2 in device example 81 with comparative compounds 7 and 8 as the capping material, while keeping the rest of the fabrication process exactly the same.

[0346]

[0347]

[0348] Table 3: Test data on the luminescence characteristics of the organic electroluminescent devices prepared in Device Examples 81-120 and Comparative Device Examples 7-8

[0349]

[0350]

[0351] As shown in Table 3, the triamine compounds described in this invention, when used as a capping layer material, can effectively refract light confined inside the device and have good thermal stability.

[0352] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triamine compound, characterized in that, The triamine compounds are shown in Formula I. R1 is independently selected from any one of deuterium, cyano, fluorine, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl, substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl fused cycloyl; The a0 is selected from 1, 2, or 3; The Ar1 is selected from the group shown in formula a; The Ar2 is selected from the group shown in formula a or formula b; X and Y are independently selected from O or S; The z and v are independently selected from CH or N; The R2 and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl rings, or adjacent R2 or adjacent R3 are bonded to each other to form a substituted or unsubstituted ring; The n1 is selected from 0, 1, 2, 3, 4 or 5; The m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; The Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C6-C60 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic groups, and substituted or unsubstituted C3-C30 alicyclic and C2-C30 heteroaryl groups. L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C30 alicyclic ring and a C6-C30 aromatic ring in a fused cycloalcoholic group, or a substituted or unsubstituted C3-C30 alicyclic ring and a C2-C30 heteroarylene ring in a fused cycloalcoholic group.

2. The triamine compound according to claim 1, characterized in that, R1 is independently selected from deuterium, cyano, fluorine, or any one of the following groups, substituted or unsubstituted: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thienyl, benzofuranyl, benzothienyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, benzofuranopyridine, benzothienopyridine, pyridyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl Quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridinoxazolyl, pyridinothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, dimethylethylsilyl, dimethyl-tert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, dimethylphenylsilyl, diethylphenylsilyl, diisopropylphenylsilyl, di-tert-butylphenylsilyl, methyl-diphenylsilyl, ethyl-diphenylsilyl, isopropyl-diphenylsilyl, tert-butyl-diphenylsilyl, triphenylsilyl.

3. The triamine compound according to claim 1, characterized in that, Formula a is selected from any one of the following groups: The R2 is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl , pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R2 groups bonded together to form substituted or unsubstituted rings; The n1 is selected from 0, 1, 2, 3, 4 or 5; the n2 is selected from 0, 1, 2, 3 or 4; the n3 is selected from 0, 1, 2 or 3; the n4 is selected from 0, 1 or 2; the n5 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the n6 is selected from 0, 1, 2, 3, 4, 5 or 6; the n7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; and the n8 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

4. The triamine compound according to claim 1, characterized in that, Formula b is selected from any one of the following groups: Y1 is selected from O, S or C(RsRt); The R3 is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl Pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent R3s bonded together to form substituted or unsubstituted rings; The Rs and Rt are independently selected from hydrogen, deuterium, cyano, halogen, or selected from any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl Benzothiophene, pyridofuran, pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl; The m1 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the m2 is selected from 0, 1, 2, 3, 4, 5 or 6; the m3 is selected from 0, 1, 2, 3, 4 or 5; the m4 is selected from 0, 1, 2, 3 or 4; the m5 is selected from 0, 1, 2 or 3; the m6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; and the m7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

5. The triamine compound according to claim 1, characterized in that, The Ar3, Ar4, Ar5, and Ar6 are independently selected from any one of the following groups: The Rd is independently selected from hydrogen, deuterium, cyano, halogen, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzothiophene, pyridofuranyl , pyridothiophene, dibenzofuran, dibenzothiophene, benzofuranopyridine, benzothiophene-pyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, or two adjacent Rd bonds to each other to form substituted or unsubstituted rings; The Re and Rf groups are independently selected from hydrogen, deuterium, cyano, or any one of the following substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, benzocyclopropyl, benzocyclobutyl, benzocyclopentyl, benzocycloheptyl, benzocyclopentenyl, benzocyclohexenyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, carbazole, furanyl, thiophene, benzofuranyl, benzene Thiopheneyl, pyridofuranyl, pyridothienyl, dibenzofuranyl, dibenzothienyl, benzofuranopyridine, benzothienopyridine, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthinyl, o-phenanthrolinel, oxazolyl, thiazolyl, benzoxazolyl, benzothiazolyl, pyridoxazolyl, pyridothiazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl; The q1 is selected from 0, 1, 2, 3, 4 or 5; the q2 is selected from 0, 1, 2, 3 or 4; the q3 is selected from 0, 1, 2 or 3; the q4 is selected from 0, 1 or 2; the q5 is selected from 0, 1, 2, 3, 4, 5 or 6; the q6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the q7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the q8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; and the q9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

6. The triamine compound according to claim 1, characterized in that, The compound of formula I is selected from any one of the following compounds:

7. An organic electroluminescent device, comprising an anode, a cathode, and an organic functional layer, wherein the organic functional layer is located between the anode and the cathode or outside either the anode or the cathode, characterized in that, The organic functional layer comprises any one or more of the triamine compounds described in any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic functional layer comprises a hole transport region, a light-emitting layer, and an electron transport region, the hole transport region being located between the anode and the light-emitting layer, and the electron transport region being located between the cathode and the light-emitting layer, characterized in that, The hole transport region comprises any one or more of the triamine compounds described in any one of claims 1-6.

9. The organic electroluminescent device according to claim 7, wherein the organic functional layer includes a capping layer located outside either the anode or the cathode, and the capping layer comprises any one or more of the triamine compounds according to any one of claims 1-6.

10. The organic electroluminescent device according to claim 7, wherein the organic functional layer comprises an anode, a cathode, a first light-emitting unit, a second light-emitting unit, and a charge-generating layer, wherein the first light-emitting unit, the second light-emitting unit, and the charge-generating layer are located between the anode and the cathode, and the charge-generating layer is located between the first light-emitting unit and the second light-emitting unit, wherein the charge-generating layer comprises any one or more of the triamine compounds described in this invention.

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