A triamine derivative and an organic electroluminescent device thereof

Abstract

The application provides a triamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. The triamine derivative provided by the application is connected with three arylamines with benzene as the center, and at least one benzopentaheterocycle is contained in the three arylamines. The triamine derivative has a suitable HOMO energy level, good hole mobility and strong electron-donating capacity, is conducive to the transmission and injection of holes, increases the transmission balance of carriers, improves the effective recombination of excitons in the light-emitting layer, and has good refractive index, high glass transition temperature, good film-forming property, excellent light extraction efficiency and reduced accumulation of internal Joule heat. When the triamine derivative is applied to an organic electroluminescent device as a hole transport layer material or a cover layer material, the luminous efficiency of the device is significantly improved and the service life is prolonged. The triamine derivative and the organic electroluminescent device thereof have good application effect and industrialization prospect.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic electroluminescent materials, in particular to a triamine derivative and an organic electroluminescent device thereof. BACKGROUND

[0002] With the progress and development of society, organic electroluminescent devices (OLED) are widely used in many fields such as display and lighting, and have the characteristics of light weight, wide viewing angle, fast response, wide temperature range, low energy consumption, high efficiency, good color purity, high definition, flexibility and the like, and are considered by the industry as one of the most promising display technologies based on these advantages.

[0003] Electroluminescence refers to the phenomenon that organic optoelectronic materials release energy in the form of light radiation under the driving of current or electric field, and directly convert electric energy into light energy. An organic electroluminescent device is usually a classic sandwich structure composed of a cathode, an anode and an organic functional layer. The organic electroluminescent device can be divided into single-layer devices, double-layer devices and multi-layer devices according to the structure. The multi-layer device is composed of an anode, a cathode and an organic layer, and the organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cover layer.

[0004] The performance of an organic electroluminescent device depends on the performance of each organic layer material. The triplet energy level of the hole transport layer material in the prior art is low, which increases the energy barrier of the hole injection and transport process, and the glass transition temperature is low, the thermal stability is poor, the film-forming property is poor, the hole mobility is low, the transport of holes and electrons is unbalanced, the effective recombination of holes and electrons in the light emitting layer is reduced, and the light emitting efficiency of the device is reduced. In addition, there is a plasmonic resonance effect between the cover layer material and the cathode material, which reduces the light extraction efficiency inside the device, so that part of the light is confined inside the device, heat accumulates and the service life of the device is reduced. In order to obtain an organic electroluminescent device with high light emitting efficiency and long service life, it is crucial to design an organic electroluminescent material with suitable HOMO energy level, high hole mobility, high glass transition temperature, good thermal stability and good film-forming property. SUMMARY

[0005] In order to solve the problem of low performance of the organic electroluminescent device in the prior art, the present application provides a triamine derivative and an organic electroluminescent device thereof.

[0006] The present application provides a triamine derivative, which has a structure as shown in formula I,

[0007]

[0008] In Formula I, Ar1 to Ar6 are the same as or different from each other, at least one of which is selected from the group represented by the formula shown below, the rest of which are the same as or different from each other, selected from any one of the groups represented by the formula shown below, and any one of Ar1 and Ar2, Ar3 and Ar4, Ar5 and Ar6 is not simultaneously substituted with a tert-butyl group;

[0009]

[0010] z and x are the same as or different from each other, selected from CH or N atom, when z and x are bonded with other groups, z and x are selected from C atom;

[0011] t1 is selected from any one of O, S, N(R), and t2 is selected from any one of O, S, N(R0);

[0012] R and R0 are the same as or different from each other, selected from any one of substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted fused ring group of C6 to C30 aromatic ring and C3 to C30 aliphatic ring, substituted or unsubstituted C2 to C30 heteroaryl, or R and R0 can be directly bonded with any one of L1 to L6;

[0013] R a , R b , R c , R d are the same as or different from each other, selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C2 to C12 alkenyl, substituted or unsubstituted C3 to C12 cycloalkyl, substituted or unsubstituted C3 to C25 silyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted fused ring group of C6 to C30 aromatic ring and C3 to C30 aliphatic ring, substituted or unsubstituted C2 to C30 heteroaryl;

[0014] m1 is selected from 0, 1, 2, 3 or 4, and m2 is selected from 0, 1 or 2, when two or more R a are present, two or more R a are the same as or different from each other, or adjacent two R a may be connected to each other to form one or more substituted or unsubstituted aromatic rings; when two or more R b are present, two or more R b are the same as or different from each other;

[0015] said n1 is selected from 0, 1, 2, 3, 4 or 5, said n2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, said n3 is selected from 0, 1, 2, 3 or 4, said n4 is selected from 0 or 1, when there are two or more R c , two or more R c are the same or different, or adjacent two R c may be connected to each other to form one or more substituted or unsubstituted rings;

[0016] said L1~L6 are the same or different, selected from any one of a single bond, a substituted or unsubstituted C6~C30arylene, a substituted or unsubstituted C2~C30heteroarylene, a divalent substituted or unsubstituted C6~C30aromatic ring and a C3~C30aliphatic ring fused ring group, and a combination thereof;

[0017] said R1~R3 are the same or different, selected from any one of hydrogen, deuterium, cyano, a trifluoromethyl group, a substituted or unsubstituted C1~C12alkyl group, a substituted or unsubstituted C3~C12cycloalkyl group, a substituted or unsubstituted C3~C25silyl group, a substituted or unsubstituted C6~C30aryl group, a substituted or unsubstituted C6~C30aromatic ring and a C3~C30aliphatic ring fused ring group, a substituted or unsubstituted C2~C30heteroaryl group;

[0018] provided that the triamine derivative is not

[0019] The present application also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside any one of the anode and the cathode, and the organic layer comprises any one or more of the triamine derivatives.

[0020] Beneficial effects: The triamine derivative represented by formula I provided by the present application has a suitable HOMO energy level, which can reduce the energy barrier to be overcome in the hole transport process, a strong electron-donating ability, a good hole mobility, which is conducive to the transmission of holes in the hole transport region, increases the effective recombination of excitons in the light-emitting layer, and has a good refractive index, a high glass transition temperature, a good film-forming property, and high thermal stability. When the triamine derivative is applied to an organic electroluminescent device as a hole transport layer material or a cover layer material, the luminous efficiency of the device is significantly improved and the service life is prolonged. DETAILED DESCRIPTION

[0021] The technical solutions of the embodiments of the present application will be described clearly and completely below. Obviously, the described embodiments are only some of the embodiments of the present application, but not all the embodiments. Based on the embodiments of the present application, all other embodiments obtained by those skilled in the art without creative work fall within the protection scope of the present application.

[0022] In the compounds of the present application, any atom not designated as a particular isotope is included as any stable isotope of that atom, and includes atoms in both their natural isotopic abundance and non-natural abundance.

[0023] In the present specification, “*” means a moiety connected to another substituent.

[0024] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be connected to any one of the corresponding optional sites of the ring. For example, may mean may mean may mean and so on.

[0025] In the present specification, when a substituent or a connecting site is through a bond between two or more rings, it means that it can be connected to any one of the two or more rings, and specifically, it can be connected to any one of the corresponding optional sites of the ring. For example, may mean or may mean and so on.

[0026] Examples of the halogen atom described in the present application can include fluorine, chlorine, bromine, or iodine.

[0027] The alkyl group described in the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule, which can be a straight-chain alkyl group or a branched-chain alkyl group, preferably has 1 to 12 carbon atoms, more preferably has 1 to 8 carbon atoms, and particularly preferably has 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples can include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and the like, but are not limited thereto.

[0028] The alkenyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from an alkenyl molecule, which can be a straight-chain alkenyl group or a branched-chain alkenyl group, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms. The alkenyl group can be substituted or unsubstituted. Specific examples can include vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylvinyl-1-yl, styryl, etc., but are not limited thereto.

[0029] The cycloalkyl group according to the present application refers to a monovalent group obtained by removing one hydrogen atom from a cycloalkane molecule, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group can be substituted or unsubstituted. The cycloalkyl group includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, etc., but is not limited thereto.

[0030] The "substituted or unsubstituted silyl group" according to the present application refers to a —Si(R k )3 group, wherein each R k is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, and a substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each R k is the same or different and is selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a halogen, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, and a substituted or unsubstituted C6-C60 aryl group. The number of carbon atoms of the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms of the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. The number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R kthe same or different groups selected from the group consisting of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3 to C25 silyl group" means a silyl group substituted with a substituted or unsubstituted C3 to C25 alkyl group or aryl group, which is preferably substituted with 3 alkyl groups, 3 aryl groups. Examples of the "substituted or unsubstituted silyl group", in particular, the "substituted or unsubstituted C3 to C25 silyl group" can include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-t-butylsilyl, triphenylsilyl, etc., but are not limited thereto.

[0031] The aryl group according to the present application means a monovalent group obtained by removing one hydrogen atom from the aromatic ring carbon of an aromatic compound molecule, and can be a monocyclic aryl group, a polycyclic aryl group, or a fused ring aryl group, preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 12 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, a phenyl group, etc., but is not limited thereto. The polycyclic aryl group means an aryl group having two or more independent aromatic rings in the molecule, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., but is not limited thereto. The fused ring aryl group means an aryl group having two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, for example, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a fluoranthenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a benzofluorenyl group, a 9,9'-spirobifluorenyl group, etc., but is not limited thereto.

[0032] The heteroaryl group according to the present application refers to the group of radicals obtained by replacing one or more of the ring carbon atoms in an aryl group with a heteroatom, including but not limited to O, S, N, Si or P atom, preferably having 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, most preferably 2 to 12 carbon atoms. The connecting site of the heteroaryl group can be located on the ring carbon atom or on the ring heteroatom, and the heteroaryl group can be monocyclic, polycyclic or fused ring heteroaryl group. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc., but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, bipyrimidyl, phenylpyridyl, phenylpyrimidyl, etc., but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolyl, quinoxalyl, benzoquinazolyl, benzoquinoxalyl, phenanthrolinyl, naphthylidinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzofuranyl, dibenzothienyl, dibenzothienyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiazinyl, spirofluorene xanthene, spirofluorene thioxanthene, etc., but is not limited thereto.

[0033] The aliphatic ring according to the present application refers to the cyclic hydrocarbon having aliphatic property, containing closed carbon ring in the molecule, preferably having 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, further preferably 3 to 12 carbon atoms, more preferably 3 to 7 carbon atoms. It can form a single ring hydrocarbon or a polycyclic hydrocarbon, and can be completely unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples can include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple single ring hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings can also be connected to each other to form a cage structure.

[0034] The fused ring of the aromatic ring and the aliphatic ring according to the present application refers to a ring in which one or more aromatic rings and one or more aliphatic rings are fused to each other by sharing two adjacent carbon atoms, the aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms, and the aliphatic ring preferably has 3 to 30 carbon atoms, more preferably C3 to C18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. The fused ring of the aromatic ring and the aliphatic ring can be substituted or unsubstituted. Examples include benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexanyl, benzocycloheptanyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropanyl, naphthocyclobutanyl, naphthocyclopentanyl, naphthocyclohexanyl, naphthocyclopentenyl, naphthocyclohexenyl, and the like, but are not limited thereto.

[0035] The arylene group according to the present application refers to a general term for a divalent group obtained by removing two hydrogen atoms from the aromatic nucleus carbon of an aromatic hydrocarbon molecule, and can be a monocyclic arylene group, a polycyclic arylene group, or a fused ring arylene group, preferably has 6 to 30 carbon atoms, more preferably has 6 to 22 carbon atoms, more preferably has 6 to 18 carbon atoms, and most preferably has 6 to 12 carbon atoms. As the monocyclic arylene group, a phenylene group or the like can be used, but is not limited thereto. The arylene group can be substituted or unsubstituted. As the polycyclic arylene group, a biphenylene group, a terphenylene group, a quaterphenylene group, or the like can be used, but is not limited thereto. As the fused ring arylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a pyrenylene group, a fluorenylene group, a spirofluorenylene group, a triphenylylene group, a perylenylene group, a fluoranthrylene group, a chrysenylene group, a pyrenylene group, a group, or the like can be used, but is not limited thereto.

[0036] The heteroarylene group according to the present application refers to a general term of divalent group obtained by removing two hydrogen atoms from the core carbon of the aromatic heterocycle composed of carbon and heteroatom, and the heteroatom can be one or more of N, O, S, Si, P, and can be monocyclic heteroarylene, polycyclic heteroarylene or fused ring heteroarylene, preferably having 2 to 30 carbon atoms, more preferably having 2 to 22 carbon atoms, still more preferably having 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms, and the heteroarylene group can be substituted or unsubstituted. Examples can include pyridylene, pyrimidylene, pyrazylene, pyridazylene, triazylene, thiophenylene, pyrrolylene, furanylene, pyranylene, oxazolyiene, thiazolyiene, imidazolyiene, benzoxazolyiene, benzothiazolyiene, benzimidazolyiene, carbazolyiene, benzocarbazolyiene, azidylene, xanthylene, thianthrene, phenazinylene, phenothiazinylene, phenoxazinylene, indolyiene, quinolyiene, isoquinolyiene, benzothiophenylene, benzofuranylene, dibenzofuranylene, dibenzothiophenylene, quinoxalyiene, quinazolyiene, naphtholyiene, purinylene, phenanthrolinylene, and the like, but are not limited thereto.

[0037] The divalent aromatic ring and aliphatic ring fused ring group according to the present application refers to a divalent group having two linking positions on the aromatic ring and aliphatic ring fused ring group. They can be applicable to the above description of the aromatic ring and aliphatic ring fused ring group except that they are divalent groups, respectively.

[0038] The "unsubstituted" in the "substituted or unsubstituted" according to the present application means that the hydrogen atoms on the group are not substituted by any substituent; "substituted" means that at least one hydrogen atom on the group is substituted by a substituent, and the position of substitution is not limited. When a plurality of hydrogens are substituted by a plurality of substituents, the plurality of substituents can be the same or different.

[0039] The substituents in the "substituted or unsubstituted" described in the present application can be the same as or different from each other, and are selected from any one of deuterium, a cyano group, a nitro group, a trifluoromethyl group, a halogen atom, a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C2 to C12 alkenyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C3 to C25 silyl group, a substituted or unsubstituted C2 to C12 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a fused ring group of a substituted or unsubstituted C6 to C30 aromatic ring and a C3 to C30 aliphatic ring, and preferably deuterium, a cyano group, a halogen atom, a trifluoromethyl group, a C1 to C12 alkyl group, a C3 to C12 cycloalkyl group, a C3 to C25 silyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, and specific examples can include deuterium, fluorine, chlorine, bromine, iodine, a cyano group, a trifluoromethyl group, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a deuterated methyl group, a deuterated i-propyl group, a deuterated t-butyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a trimethylsilyl group, a triethylsilyl group, a tri-i-propylsilyl group, a tri-t-butylsilyl group, a triphenylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, a tolyl group, a penta-deuterated phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a triphenylenyl group, a perylenyl group, a fluoranthenyl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9-methyl-9-phenylfluorenyl group, a spirofluorenyl group, a carbazolyl group, a 9-phenylcarbazolyl group, a 9,9'-spirobifluorenyl group, a benzocyclopropanyl group, a benzocyclobutanyl group, a benzocyclopentanyl group, a benzocyclohexanyl group, a benzocycloheptanyl group, a benzocyclobutenyl group, a benzocyclopentenyl group, a benzocyclohexenyl group, a benzocycloheptenyl group, a pyrrolyl group, a furanyl group, a thiophenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, an oxazolyl group, a thiazolyl group, an imidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzotriazolyl group, a benzimidazolyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolyl group, a phenothiazinyl group, a phenoxazinyl group, an acridinyl group, and the like, but are not limited thereto.

[0040] The "connection to form a ring" described in the present application means that two groups are connected to each other by a chemical bond and optionally aromatized. As an example, the following is shown:

[0041]

[0042] ​In the present specification, a ring formed by linking can be an aromatic ring or a non-aromatic ring, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, an eight-membered ring, a fused ring, and the like, for example, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornane, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, and the like, but is not limited thereto.

[0043] The present application provides a triamine derivative having a structure as shown in Formula I,

[0044]

[0045] In Formula I, Ar1 to Ar6 are the same as or different from each other, at least one of which is selected from the remaining ones are the same as or different from each other, and are selected from any one of the groups shown below, and any one of Ar1 and Ar2, Ar3 and Ar4, and Ar5 and Ar6 is not simultaneously substituted with a tert-butyl group;

[0046]

[0047] z and x are the same as or different from each other, and are selected from a CH or N atom, and when z and x are bonded to other groups, z and x are selected from a C atom;

[0048] t1 is selected from any one of O, S, and N(R), and t2 is selected from any one of O, S, and N(R0);

[0049] R and R0 are the same as or different from each other, and are selected from any one of a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted fused ring group of a C6 to C30 aromatic ring and a C3 to C30 aliphatic ring, a substituted or unsubstituted C2 to C30 heteroaryl group, or R and R0 can be directly bonded to any one of L1 to L6;

[0050] R a , R b , R c , R deach independently of one another selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring-fused with C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0051] m1 is selected from 0, 1, 2, 3, or 4, m2 is selected from 0, 1, or 2, when two or more R a are present, two or more R a may be joined to form one or more substituted or unsubstituted aromatic rings; a when two or more R b are present, two or more R b are the same or different;

[0052] n1 is selected from 0, 1, 2, 3, 4, or 5, n2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, n3 is selected from 0, 1, 2, 3, or 4, n4 is selected from 0 or 1, when two or more R c are present, two or more R c may be joined to form one or more substituted or unsubstituted rings; c

[0053] L1-L6 are the same or different, selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, divalent substituted or unsubstituted C6-C30 aromatic ring-fused with C3-C30 aliphatic ring, and combinations thereof;

[0054] R1-R3 are the same or different, selected from any one of hydrogen, deuterium, cyano, trifluoromethyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 aromatic ring-fused with C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl;

[0055] provided that the triamine derivative is not

[0056] ​Preferably, the triamine derivative is selected from any one of the following structures:

[0057]

[0058] Preferably, at least one of Ar1to Ar6is selected from the group consisting of: one of Ar1to Ar6is selected from the group, in particular, Ar1, Ar2, Ar3, Ar4, Ar5or Ar6is selected from the group; two of Ar1to Ar6are selected from the group, in particular, Ar1and Ar2, Ar1and Ar3, Ar1and Ar5, Ar3and Ar4, Ar3and Ar5, Ar5and Ar6are selected from the group; three of Ar1to Ar6are selected from the group, in particular, Ar1, Ar2and Ar3, Ar1, Ar2and Ar5, Ar1, Ar3and Ar4, Ar1, Ar3and Ar5, Ar1, Ar5and Ar6, Ar3, Ar4and Ar5, Ar3, Ar5and Ar6are selected from the group; four of Ar1to Ar6are selected from the group, in particular, Ar1, Ar2, Ar3and Ar4, Ar1, Ar2, Ar3and Ar5, Ar1, Ar2, Ar5and Ar6, Ar1, Ar3, Ar4and Ar5, Ar1, Ar3, Ar5and Ar6, Ar3, Ar4, Ar5and Ar6are selected from the group; five of Ar1to Ar6are selected from the group, in particular, Ar1, Ar2, Ar3, Ar4and Ar5, Ar1, Ar2, Ar3, Ar5and Ar6are selected from the group; six of Ar1to Ar6are selected from the group, in particular, Ar1, Ar2, Ar3, Ar4, Ar5and Ar6are selected from the group.

[0059] Preferably, the triamine derivative is selected from any one of the following structures: is selected from any one of the following groups:

[0060]

[0061] t1is selected from any one of O, S, N(R);

[0062] R, equal to or different from each other, is selected from any one of the following groups substituted or unsubstituted with one or more deuterium, trifluoromethyl, halogen, cyano, C1-C12alkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, adamantoyl, norbornanoyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, benzocyclopropanoyl, benzocyclobutanoyl, benzocyclopentanoyl or benzocyclohexanoyl, or R can be directly bonded to any one of L1to L6;

[0063] said R a , R b are identical or different from each other and are selected from the group consisting of hydrogen, deuterium, cyano, trifluoromethyl or any one of the following groups, which can be substituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, C1-C12 alkyl or are unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexan- yl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, ben- zocyclopropanyl, benzocyclobutanyl, benzocyclopentanyl, benzocyclohexan- yl, benzofuranyl or benzothiophenyl;

[0064] said a1 is selected from 0, 1, 2, 3 or 4, said a2 is selected from 0, 1 or 2, said a3 is selected from 0, 1, 2 or 3, said a4 is selected from 0 or 1, said a5 is selected from 0, 1, 2, 3, 4, 5 or 6, said a6 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a7 is selected from 0, 1, 2, 3, 4 or 5, said a8 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0065] Preferably, said is selected from any one of the following groups,

[0066]

[0067]

[0068]

[0069] said t1 is selected from any one of O, S, N(R);

[0070] said R are identical or different from each other and are selected from any one of the following groups, which can be substituted by one or more deuterium, trifluoromethyl, halogen, cyano, C1-C12 alkyl or are unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexan- yl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentan- yl or benzocyclohexanyl, or R can be directly bound to any one of L1 to L6;

[0071] said b1 is selected from 1, 2, 3, 4 or 5, said b2 is selected from 1, 2, 3 or 4, said b3 is selected from 1, 2, 3, 4, 5, 6 or 7, said b4 is selected from 1, 2, 3, 4, 5 or 6.

[0072] Preferably, Ar1to Ar6are the same as or different from each other, at least one of which is selected from the remaining ones of which are the same as or different from each other, are selected from any one of the following groups,

[0073]

[0074] x is the same as or different from each other, is selected from a CH or N atom, when x is bonded to other groups, x is selected from a C atom;

[0075] t2is selected from any one of O, S, N(R0);

[0076] R0is the same as or different from each other, is selected from any one of the following groups substituted with one or more deuterium, trifluoromethyl, halogen, cyano, C1-C12 alkyl, or unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, or benzocyclohexane, or R0may be directly bonded to any one of L1to L6;

[0077] R c , R d are the same as or different from each other, are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups substituted with one or more deuterium, cyano, trifluoromethyl, C1-C12 alkyl, or unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornane, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolyl, quinoxalyl, naphthrydinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzofuranyl, or benzothiophenyl;

[0078] c1is selected from 0, 1, 2, 3, 4, or 5, c2is selected from 0, 1, 2, 3, 4, 5, 6, or 7, c3is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, c4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, c5is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, c6is selected from 0, 1, 2, 3, or 4, c7is selected from 0 or 1, c8is selected from 0, 1, 2, 3, 4, 5, or 6, and c9is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0079] Preferably, Ar1to Ar6are the same as or different from each other, at least one of which is selected from the remaining ones of which are the same as or different from each other, are selected from any one of the following groups,

[0080]

[0081]

[0082]

[0083] t2is selected from any one of O, S, and N(R0);

[0084] R0is the same as or different from each other, is selected from any one of the following groups substituted with one or more deuterium, trifluoromethyl, halogen, cyano, C1to C12alkyl, or unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanoyl, cyclohexanoyl, adamantoyl, norbornanoyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, benzocyclopropanoyl, benzocyclobutanoyl, benzocyclopentanoyl, or benzocyclohexanoyl, or R0may be directly bonded to any one of L1to L6;

[0085] R c , R d are the same as or different from each other, are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups substituted with one or more deuterium, cyano, trifluoromethyl, C1to C12alkyl, or unsubstituted: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanoyl, cyclobutanoyl, cyclopentanoyl, cyclohexanoyl, adamantoyl, norbornanoyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropanoyl, benzocyclobutanoyl, benzocyclopentanoyl, benzocyclohexanoyl, benzofuranyl, or benzothiophenyl;

[0086] d1is selected from 0, 1, 2, 3, 4, or 5, d2is selected from 0, 1, 2, 3, or 4, d3is selected from 0, 1, 2, 3, 4, 5, 6, or 7, d4is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, d5is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, d6is selected from 0, 1, 2, or 3, d7is selected from 0, 1, or 2, d8is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, d9is selected from 0, 1, 2, 3, 4, 5, or 6, d10is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d11is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d12is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d13is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d14is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d15is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d16is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d17is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d18is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d19is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d20is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d21is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d22is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d23is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d24is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d25is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20, d26is selected from 0, 1, 2, 3, 4, 5, 610 d is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, said d 11 d is selected from 0 or 1, said d 12 d is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13.

[0087] Preferably, L1to L6are the same or different from each other and are selected from a single bond or any one of the following structures,

[0088]

[0089]

[0090] R is selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, halogen, trimethylsilyl, C1to C12alkyl, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanly, adamantyl, norbornanyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanly, or benzocyclohexanly; e R is selected from hydrogen, deuterium, cyano, trifluoromethyl, halogen, or any one of the following groups substituted or unsubstituted with one or more deuterium, cyano, trifluoromethyl, halogen, trimethylsilyl, C1to C12alkyl, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanly, adamantyl, norbornanyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthrydinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclopentanly, or benzocyclohexanly;

[0091] e1is selected from 0, 1, 2, 3, or 4, e2is selected from 0, 1, 2, or 3, e3is selected from 0, 1, or 2, e4is selected from 0 or 1, e5is selected from 0, 1, 2, 3, 4, 5, or 6, e6is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, and e7is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0092] Preferably, the triamine derivative is selected from any one of the following structures,

[0093]

[0094]

[0095]

[0096]

[0097]

[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] The above lists some specific structural forms of the triamine derivatives of the present application represented by Formula I, but the present application is not limited to these listed chemical structures, and any structure based on Formula I and having substituents as defined above should be included.

[0135] The present application provides a method for preparing the compound represented by Formula I through a carbon-nitrogen coupling reaction well known in the art, but the preparation method of the present application is not limited thereto, and the specific synthesis route is shown as follows:

[0136] Preparation of intermediate A:

[0137]

[0138] Preparation of intermediate B:

[0139]

[0140] Preparation of intermediate C:

[0141]

[0142] Preparation of Formula I compound:

[0143] 1. When intermediate A, intermediate B and intermediate C are not the same as each other:

[0144]

[0145] 2. When intermediate A and intermediate B are the same:

[0146]

[0147] 3. When the intermediate A, the intermediate B and the intermediate C are the same as each other:

[0148]

[0149] wherein X a are the same as or different from each other, and are selected from any one of Cl, Br and I; Ar1 to Ar6, L1 to L6, R1 to R3 are the same as described above.

[0150] The substituents described above can be bonded by a method known in the art, and the kind and position of the substituents or the number of the substituents can be changed according to a technique known in the art.

[0151] The present application also provides an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside of any one of the anode and the cathode, and the organic layer comprises any one or more of the triamine derivatives described above.

[0152] Preferably, the organic layer described above is located between the anode and the cathode, and comprises at least one of a hole transport region, a light emitting layer, and an electron transport region.

[0153] Preferably, the hole transport region described above comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

[0154] Preferably, at least one of the hole injection layer, the hole transport layer, and the electron blocking layer described above comprises any one or more of the triamine derivatives described above.

[0155] Preferably, the hole transport layer described above comprises a first hole transport layer and / or a second hole transport layer, and the first hole transport layer and / or the second hole transport layer comprises any one or more of the triamine derivatives described above.

[0156] Preferably, the light emitting layer described above comprises a host material and a dopant material.

[0157] Preferably, the electron transport region described above comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0158] Preferably, the organic layer described above is located outside of any one of the anode and the cathode, and the organic layer comprises a capping layer, and the capping layer comprises any one or more of the triamine derivatives described above.

[0159] The material of each thin film layer in the organic electroluminescent device according to the present application is not particularly limited, and a material known in the art can be used. Each organic functional layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are described below, respectively.

[0160] The organic electroluminescent device according to the present application is generally formed on a substrate. The substrate described above can be any substrate that does not change when electrodes and organic layers are formed, such as a glass, a plastic, a polymer film, silicon, or the like.

[0161] The anode material according to the present application preferably uses a material having a high functional function to improve the hole injection efficiency. The anode material that can be used in the present application is selected from the group consisting of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single layer structure or a multi-layer structure including two or more layers, for example, the anode can have a single layer structure of Al or a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0162] The hole injection layer according to the present application preferably uses a material having a good ability to accept holes. Specific examples of the hole injection layer material that can be used in the present application can include silver oxide, vanadium oxide, tungsten oxide, copper oxide, titanium oxide, and other metal oxides, phthalocyanine compounds, benzidine compounds, phenazine compounds, and the like, but are not limited thereto.

[0163] The hole transport layer material according to the present application preferably has a material having a high hole mobility. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, diphenylamine derivatives, fluorene derivatives, stilbene derivatives, hexacene hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, and the like, but is not limited thereto. Preferably, the triamine derivative according to the present application.

[0164] The light-emitting layer material according to the present application includes a host material and a dopant material. The light-emitting layer host material needs to have bipolar charge transport properties and appropriate energy levels, and is selected from 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (a-AND), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"'-terphenyl]-4,4"-diamine (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), and the like. In addition to the above materials and combinations thereof, the light-emitting layer host material can also include other known materials suitable for light-emitting layers, but is not limited thereto. The light-emitting layer dopant material according to the present application is classified into blue light-emitting materials, green light-emitting materials, and red light-emitting materials. The light-emitting layer dopant material can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, and is selected from 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)picolatoiridium (FIrpic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-di[N-(p-tolyl)anilino]anthracene (TPA), tris[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), and the like, but is not limited thereto.

[0165] The hole blocking layer according to the present application preferably uses a material having strong hole blocking ability and appropriate HOMO / LUMO energy levels. The hole blocking layer material according to the present application can be selected from any one or several of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazaphenanthrene derivatives, azabenzene derivatives, anthrone derivatives, and the like, but is not limited thereto.

[0166] The electron transport layer material according to the present application is preferably a material having a high electron mobility. It can be selected from any one or more of the following structures: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 1,3,5-tris(N-phenyl-2-benzimidazole) benzene (TPBi), tris(8-hydroxyquinoline)aluminum (III) (Alq3), 8-hydroxyquinoline-lithium (Liq), bis(2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), and 3-(diphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), and the like, but is not limited thereto.

[0167] The electron injection layer material according to the present application is preferably a material having a small difference in potential barrier from the material of the adjacent organic layer. Specific examples can include: alkali metal compounds (e.g., lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, cesium 8-hydroxyquinolate, aluminum 8-hydroxyquinolate), organic metal salts (metal acetate, metal benzoate, or metal stearate), molybdenum trioxide, metallic aluminum, and the like, but is not limited thereto.

[0168] The cathode material according to the present application is preferably a material having a low work function that can facilitate electron injection into the organic layer, thereby lowering the electron injection barrier. It can be selected from any one or more of the following materials: Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including the same, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.

[0169] The cover layer according to the present application is provided on the outside of any one of the anode and the cathode, and is preferably a material that can improve the internal light coupling efficiency of the device. It can be selected from any one or more of the following structures: arylamine derivatives, biscarbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, benzofuran derivatives, bisamine derivatives, porphyrin derivatives, phthalocyanine derivatives, and the like, but is not limited thereto. Preferably, the triamine derivative according to the present application is used.

[0170] The thickness of each organic layer of the organic electroluminescent device according to the present application is not particularly limited, and a thickness commonly used in the art can be used.

[0171] The organic electroluminescent device according to the present application can be manufactured by any one of a vacuum evaporation method, a spin coating method, a vapor deposition method, a blade coating method, a laser thermal transfer printing method, an electro-spray coating method, a slot coating method, and a dip coating method.

[0172] The organic electroluminescent device provided by the present application can be widely applied in the fields of panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, indicator, signal lamp and the like.

[0173] The present application is explained in more detail by the following examples, but is not intended to be limited thereby. Based on this description, one of ordinary skill in the art will be able to practice the application and prepare other compounds and devices according to the present application without undue experimentation, all without departing from the scope of the application.

[0174] Preparation and characterization of compounds

[0175] Description of raw materials, reagents and characterization equipment:

[0176] The raw materials and reagents used in the following examples of the present application are not particularly limited and can be commercially available products or prepared by methods well known to those skilled in the art. The raw materials and reagents used in the present application are reagent pure.

[0177] Mass spectrometry uses a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer in the UK, chloroform as the solvent;

[0178] Elemental analysis uses a Vario EL cube organic elemental analyzer of Elementar Company in Germany, and the sample mass is 5-10 mg;

[0179] Synthesis Example 1: Preparation of compound 8

[0180]

[0181] Preparation of intermediate A-8:

[0182] Under nitrogen protection, a-8 (100.00 mmol, 15.70 g), b-8 (105.00 mmol, 9.78 g), 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (1.00 mmol, 0.73 g), sodium tert-butoxide (175.00 mmol, 16.82 g) were added into the reaction bottle in turn, then 500 mL of toluene was added, and the reaction was heated to reflux for 4 hours. After the reaction was completed, it was cooled to room temperature, distilled water was added, extracted with dichloromethane, and separated by standing. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by reduced pressure distillation. The crystals were precipitated by cooling, suction filtered, and the obtained solid was recrystallized with ethyl acetate to obtain intermediate A-8 (14.38 g, yield 85%), and the solid purity was ≥99.70% detected by HPLC. Mass spectrometry m / z: 169.0879 (theoretical value: 169.0891).

[0183] Preparation of intermediate B-8:

[0184] Following the same procedure of preparation of intermediate A-8, a-8 was replaced by equimolar of c-8, b-8 was replaced by equimolar of d-8, to obtain intermediate B-8 (26.68 g, yield 83%) with solid purity > 99.76% by HPLC. Mass m / z: 321.1530 (Theoretical: 321.1517).

[0185] Preparation of intermediate C-8:

[0186] Following the same procedure of preparation of intermediate A-8, a-8 was replaced by equimolar of e-8, b-8 was replaced by equimolar of f-8, to obtain intermediate C-8 (23.85 g, yield 81%) with solid purity > 99.73% by HPLC. Mass m / z: 294.1719 (Theoretical: 294.1719).

[0187] Preparation of intermediate I-8:

[0188] Into a reaction flask was added g-8 (60.00 mmol, 19.04 g), A-8 (60.00 mmol, 10.15 g), palladium acetate (0.60 mmol, 0.13 g), tri-tert-butylphosphine (2.4 mL of 0.50 M solution in toluene, 1.20 mmol), sodium tert-butoxide (150 mmol, 14.42 g) and 300 mL of toluene under nitrogen protection, the mixture was stirred and heated to reflux for 5.5 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added to extract, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, purified by silica gel column chromatography (dichloromethane: n-hexane = 1:8) to obtain intermediate I-8 (17.86 g, yield 83%) with solid purity > 99.85% by HPLC. Mass m / z: 356.9935 (Theoretical: 356.9920).

[0189] Preparation of intermediate II-8:

[0190] To a reaction flask was added I-8 (40.00 mmol, 14.35 g), B-8 (40.00 mmol, 12.86 g), palladium acetate (0.40 mmol, 0.09 g), tri-tert-butylphosphine (1.6 mL of 0.50 M solution in toluene, 0.80 mmol), sodium tert-butoxide (90.00 mmol, 8.65 g) and 250 mL of toluene under nitrogen protection, the mixture was stirred and heated to reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain intermediate II-8 (18.93 g, yield 79%), the solid purity was ≥99.82% detected by HPLC. Mass m / z: 598.2192 (theoretical value: 598.2176).

[0191] Preparation of compound 8:

[0192] To a reaction flask was added II-8 (20.00 mmol, 11.98 g), C-8 (20.00 mmol, 5.89 g), tris-dibenzylideneacetone dichloropalladium (0.20 mmol, 0.18 g), X-Phos (0.40 mmol, 0.19 g), sodium tert-butoxide (50.00 mmol, 4.80 g) and 200 mL of toluene under nitrogen protection, the mixture was stirred and heated to reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the solid was recrystallized from toluene to obtain compound 8 (12.86 g, yield 75%), the solid purity was ≥99.93% detected by HPLC. Mass m / z: 856.4140 (theoretical value: 856.4128). Theoretical elemental content (%) 62 H 36 D9N3O: C, 86.88; H, 6.35; N, 4.90. Found elemental content (%): C, 86.90; H, 6.34; N, 4.87.

[0193] Synthesis Example 2: Preparation of compound 50

[0194]

[0195] Preparation of intermediate C-50:

[0196] Following the same preparation method as intermediate A-8 in Synthesis Example 1, a-8 was replaced with an equimolar amount of e-50 to obtain intermediate C-50 (28.92 g, yield 80%). The solid purity was ≥99.71% as determined by HPLC. Mass spectrometry m / z: 361.1482 (theoretical value: 361.1467).

[0197] Preparation of intermediate II-50:

[0198] Under nitrogen protection, g-50 (40.00 mmol, 11.94 g), A-8 (80.00 mmol, 13.54 g), palladium acetate (0.45 mmol, 0.10 g), x-phos (0.90 mmol, 0.43 g), sodium tert-butoxide (120.00 mmol, 11.53 g), and 400 mL of toluene were added sequentially to a reaction flask. The mixture was stirred and refluxed for 6.5 hours. After the reaction was complete, the mixture was cooled to room temperature, and dichloromethane and distilled water were added to extract the mixture. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1:5) to obtain II-50 (13.87 g, yield 73%). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 474.1848 (theoretical value: 474.1863).

[0199] Preparation of compound 50:

[0200] Under nitrogen protection, II-50 (20.00 mmol, 9.50 g), C-50 (21.00 mmol, 7.59 g), tris(dibenzylacetone)palladium (0.25 mmol, 0.23 g), tri-tert-butylphosphine (1.00 mL of 0.50 M toluene solution, 0.50 mmol), sodium tert-butoxide (50.00 mmol, 4.80 g), and 200 mL of toluene were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 7.5 hours. After the reaction was complete, the mixture was cooled to room temperature, and dichloromethane and distilled water were added for extraction. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Crystallization was carried out at a lower temperature, filtered, and the resulting solid was recrystallized from toluene to give compound 50 (11.36 g, yield 71%). The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrometry m / z: 799.3580 (theoretical value: 799.3563). Theoretical elemental content (%) C 58 H 45 N3O: C, 87.08; H, 5.67; N, 5.25. Measured elemental content (%): C, 87.10; H, 5.70; N, 5.23.

[0201] Synthesis Example 3: Preparation of Compound 59

[0202]

[0203] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with an equal molar of a-63, e-50 with an equal molar of e-63, b-8 with an equal molar of d-8, g-50 with an equal molar of g-59, to obtain compound 63 (13.74 g) with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 847.3573 (theoretical value: 847.3563). Theoretical elemental content (%) C 62 H 45 N3O: C, 87.81 ; H, 5.35; N, 4.95. Found: C, 87.78; H, 5.36; N, 4.92.

[0204] Synthesis Example 4: Preparation of compound 63

[0205]

[0206] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with an equal molar of a-63, e-50 with an equal molar of e-63, b-8 with an equal molar of d-8, g-50 with an equal molar of g-59, to obtain compound 63 (13.74 g) with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 847.3573 (theoretical value: 847.3563). Theoretical elemental content (%) C 62 H 45 N3O: C, 87.81 ; H, 5.35; N, 4.95. Found: C, 87.78; H, 5.36; N, 4.92.

[0207] Synthesis Example 5: Preparation of compound 79

[0208]

[0209] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with an equal molar of a-63, e-50 with an equal molar of e-63, b-8 with an equal molar of d-8, g-50 with an equal molar of g-59, to obtain compound 63 (13.74 g) with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 847.3573 (theoretical value: 847.3563). Theoretical elemental content (%) C 62 H 45 N3O: C, 87.81 ; H, 5.35; N, 4.95. Found: C, 87.78; H, 5.36; N, 4.92.

[0210] Synthesis Example 6: Preparation of compound 96

[0211]

[0212] Following the procedure of synthesis example 2 for the preparation of compound 50, replace a-8 with an equivalent molar of c-8, e-50 with an equivalent molar of e-96, b-8 with an equivalent molar of f-96, g-50 with an equivalent molar of g-59, to obtain compound 96 (13.57 g) with solid purity > 99.92% by HPLC. Mass spectrum m / z: 847.3572 (calcd 847.3563). Theoretical elemental content (%) C 62 H 45 N3O: C, 87.81 ; H, 5.35; N, 4.95. Found: C, 87.78; H, 5.37; N, 4.92.

[0213] Synthesis Example 7: Preparation of compound 112

[0214]

[0215] Following the procedure of synthesis example 2 for the preparation of compound 50, replace a-8 with an equivalent molar of c-8, e-50 with an equivalent molar of e-112, g-50 with an equivalent molar of g-59, to obtain compound 112 (13.74 g) with solid purity > 99.95% by HPLC. Mass spectrum m / z: 847.3575 (calcd 847.3563). Theoretical elemental content (%) C 62 H 45 N3O: C, 87.81 ; H, 5.35; N, 4.95. Found: C, 87.79; H, 5.39; N, 4.93.

[0216] Synthesis Example 8: Preparation of compound 137

[0217]

[0218] Following the procedure of synthesis example 2 for the preparation of compound 50, replace a-8 with an equivalent molar of a-137, e-50 with an equivalent molar of e-63, b-8 with an equivalent molar of d-8, g-50 with an equivalent molar of g-59, to obtain compound 137 (13.56 g) with solid purity > 99.94% by HPLC. Mass spectrum m / z: 857.4177 (calcd 857.4190). Theoretical elemental content (%) C 62 H 35 D 10N3O: C, 86.78; H, 6.46; N, 4.90. Found: C, 86.80; H, 6.44; N, 4.88.

[0219] Synthesis Example 9: Preparation of compound 173

[0220]

[0221] According to the preparation method of compound 50 of synthesis example 2, a-8 was replaced with equimolar of a-236, b-8 was replaced with equimolar of d-8, e-50 was replaced with equimolar of e-59, b-8 was replaced with equimolar of d-8, and g-50 was replaced with equimolar of g-59 to obtain compound 236 (13.84 g) with solid purity ≥ 99.93% detected by HPLC. Mass m / z: 875.3890 (theoretical value: 875.3876). Theoretical elemental content (%) C 62 H 35 D 10 N3O: C, 87.74; H, 5.64; N, 4.80. Found: C, 87.72; H, 5.66; N, 4.79.

[0222] Synthesis Example 10: Preparation of compound 236

[0223]

[0224] According to the preparation method of compound 50 of synthesis example 2, a-8 was replaced with equimolar of a-236, b-8 was replaced with equimolar of d-8, e-50 was replaced with equimolar of e-59, b-8 was replaced with equimolar of d-8, and g-50 was replaced with equimolar of g-59 to obtain compound 236 (13.84 g) with solid purity ≥ 99.93% detected by HPLC. Mass m / z: 875.3890 (theoretical value: 875.3876). Theoretical elemental content (%) C 64 H 49 N3O: C, 87.74; H, 5.64; N, 4.80. Found: C, 87.72; H, 5.66; N, 4.79.

[0225] Synthesis Example 11: Preparation of compound 369

[0226]

[0227] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-369, e-50 with an equal molar amount of e-369, g-50 with an equal molar amount of g-59, compound 369 (12.98 g) was obtained with a purity > 99.90% solids by HPLC. Mass spectrum m / z: 888.4782 (calcd 888.4767). Theoretical elemental content (%) C 63 H 60 N4O: C, 85.10; H, 6.80; N, 6.30. Found: C, 85.08; H, 6.82; N, 6.27.

[0228] Synthesis Example 12: Preparation of compound 427

[0229]

[0230] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-427, e-50 with an equal molar amount of e-59, b-8 with an equal molar amount of d-8, g-50 with an equal molar amount of g-59, compound 427 (14.36 g) was obtained with a purity > 99.92% solids by HPLC. Mass spectrum m / z: 919.5430 (calcd 919.5441). Theoretical elemental content (%) C 66 H 69 N3O: C, 86.14; H, 7.56; N, 4.57. Found: C, 86.11; H, 7.58; N, 4.60.

[0231] Synthesis Example 13: Preparation of compound 435

[0232]

[0233] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-435, b-8 with an equal molar amount of b-173, e-50 with an equal molar amount of e-8, b-8 with an equal molar amount of f-435, g-50 with an equal molar amount of g-59, compound 435 (11.41 g) was obtained with a purity > 99.97% solids by HPLC. Mass spectrum m / z: 791.4520 (calcd 791.4505). Theoretical elemental content (%) C 56 H 21 D 20 N3O: C, 84.92; H, 7.76; N, 5.31. Found: C, 84.90; H, 7.78; N, 5.29.

[0234] Synthesis Example 14: Preparation of compound 455

[0235]

[0236] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equimolar amount of a-63, e-50 with an equimolar amount of e-59, b-8 with an equimolar amount of f-507, g-50 with an equimolar amount of g-59, compound 507 (12.92 g) was obtained with a solid purity > 99.93% as determined by HPLC. Mass spectrum m / z: 827.3861 (calculated: 827.3876). Theoretical elemental content (%) C 56 H 41 N3O: C, 87.03; H, 5.96; N, 5.07. Found: C, 87.04; H, 5.93; N, 5.10.

[0237] Synthesis Example 15: Preparation of compound 507

[0238]

[0239] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equimolar amount of a-63, e-50 with an equimolar amount of e-59, b-8 with an equimolar amount of f-507, g-50 with an equimolar amount of g-59, compound 507 (12.92 g) was obtained with a solid purity > 99.93% as determined by HPLC. Mass spectrum m / z: 827.3861 (calculated: 827.3876). Theoretical elemental content (%) C 60 H 49 N3O: C, 87.03; H, 5.96; N, 5.07. Found: C, 87.04; H, 5.93; N, 5.10.

[0240] Synthesis Example 16: Preparation of compound 549

[0241]

[0242] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equimolar amount of a-63, e-50 with an equimolar amount of e-59, b-8 with an equimolar amount of f-507, g-50 with an equimolar amount of g-59, compound 507 (12.92 g) was obtained with a solid purity > 99.93% as determined by HPLC. Mass spectrum m / z: 827.3861 (calculated: 827.3876). Theoretical elemental content (%) C 58 H 41 N3O: C, 87.03; H, 5.96; N, 5.07. Found: C, 87.04; H, 5.93; N, 5.10.

[0243] Synthesis Example 17: Preparation of compound 581

[0244]

[0245] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-581, e-50 with an equivalent molar of e-8, b-8 with an equivalent molar of d-8, g-50 with an equivalent molar of g-59, to obtain compound 581 (14.73 g) with solid purity > 99.91% by HPLC. Mass spectrum m / z: 955.4359 (theoretical value: 955.4378). Theoretical elemental content (%) C 70 H 41 D8N3O: C, 87.93; H, 6.01; N, 4.39. Found elemental content (%) C, 87.90; H, 6.03; N, 4.40.

[0246] Synthesis Example 18: Preparation of compound 590

[0247]

[0248] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-590, e-50 with an equivalent molar of e-59, g-50 with an equivalent molar of g-59, to obtain compound 590 (14.39 g) with solid purity > 99.93% by HPLC. Mass spectrum m / z: 971.3856 (theoretical value: 971.3876). Theoretical elemental content (%) C 72 H 49 N3O: C, 88.95; H, 5.08; N, 4.32. Found elemental content (%) C, 88.93; H, 5.10; N, 4.29.

[0249] Synthesis Example 19: Preparation of compound 626

[0250]

[0251] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-626, b-8 with an equivalent molar of d-8, e-50 with an equivalent molar of e-63, b-8 with an equivalent molar of d-8, g-50 with an equivalent molar of g-59, to obtain compound 626 (14.29 g) with solid purity > 99.95% by HPLC. Mass spectrum m / z: 927.4178 (theoretical value: 927.4189). Theoretical elemental content (%) C 68 H 53N3O: C, 87.99; H, 5.76; N, 4.53. Found (%,): C, 87.97; H, 5.80; N, 4.52.

[0252] Synthesis Example 20: Preparation of compound 720

[0253]

[0254] According to the preparation method of compound 50 in synthesis example 2, a-8 was replaced with equimolar a-720, e-50 was replaced with equimolar e-720, g-50 was replaced with equimolar g-59, compound 720 (11.90 g) was obtained, the solid purity was ≥99.90% detected by HPLC. Mass m / z: 825.3709 (theoretical value: 825.3719). Theoretical elemental content (%) C 60 H 47 N3O: C, 87.99; H, 5.76; N, 4.53. Found (%,): C, 87.97; H, 5.80; N, 4.52.

[0255] Synthesis Example 21: Preparation of compound 770

[0256]

[0257] According to the preparation method of compound 50 in synthesis example 2, a-8 was replaced with equimolar c-8, e-50 was replaced with equimolar e-8, b-8 was replaced with equimolar f-770, g-50 was replaced with equimolar g-770, compound 770 (12.60 g) was obtained, the solid purity was ≥99.94% detected by HPLC. Mass m / z: 862.3688 (theoretical value: 862.3672). Theoretical elemental content (%) C 62 H 46 N4O: C, 86.28; H, 5.37; N, 6.49. Found (%,): C, 86.30; H, 5.35; N, 6.50.

[0258] Synthesis Example 22: Preparation of compound 775

[0259]

[0260] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with equimolar of a-775, replace e-50 with equimolar of e-59, replace b-8 with equimolar of d-8, replace g-50 with equimolar of g-59, to obtain compound 775 (15.48 g), HPLC tested solid purity ≥ 99.96%. Mass spectrum m / z: 991.4335 (theoretical value: 991.4353). Theoretical elemental content (%) C 68 H 61 N3OSi2: C, 82.30; H, 6.20; N, 4.23. Found elemental content (%) C, 82.28; H, 6.17; N, 4.25.

[0261] Synthesis Example 23: Preparation of compound 848

[0262]

[0263] Preparation of compound 848:

[0264] Into a reaction flask was placed g-848 (20.00 mmol, 6.30 g), C-59 (60.00 mmol, 17.12 g), tris-dibenzylideneacetone palladium (0.25 mmol, 0.23 g), tri-tert-butylphosphine (1.0 mL of 0.50 M solution in toluene, 0.50 mmol), sodium tert-butoxide (60.00 mmol, 5.77 g) and 250 mL of toluene under nitrogen protection, the mixture was stirred and heated to reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, dichloromethane and distilled water were added to the mixture for extraction, the organic phase was collected after standing for separation, dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated under reduced pressure, and the solid was obtained by crystallization under cooling, which was recrystallized with toluene to obtain compound 848 (14.66 g, yield 79%), HPLC tested solid purity ≥ 99.97%. Mass spectrum m / z: 927.3443 (theoretical value: 927.3461). Theoretical elemental content (%) C 66 H 45 N3O3: C, 85.41; H, 4.89; N, 4.53. Found elemental content (%) : C, 85.39; H, 4.91; N, 4.56.

[0265] Synthesis Example 24: Preparation of compound 918

[0266]

[0267] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar of a-63, e-50 with an equal molar of e-977, b-8 with an equal molar of f-79, g-50 with an equal molar of g-59, compound 977 (13.95 g) was obtained with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 863.3324 (theoretical value: 863.3334). Theoretical elemental content (%) C 62 H 45 N3S: C, 86.18; H, 5.25; N, 4.86. Found: C, 86.20; H, 5.24; N, 4.90.

[0268] Synthesis Example 25: Preparation of compound 929

[0269]

[0270] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar of a-63, e-50 with an equal molar of e-977, b-8 with an equal molar of f-79, g-50 with an equal molar of g-59, compound 977 (13.95 g) was obtained with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 863.3324 (theoretical value: 863.3334). Theoretical elemental content (%) C 62 H 45 N3S: C, 86.18; H, 5.25; N, 4.86. Found: C, 86.20; H, 5.24; N, 4.90.

[0271] Synthesis Example 26: Preparation of compound 941

[0272]

[0273] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar of a-63, e-50 with an equal molar of e-977, b-8 with an equal molar of f-79, g-50 with an equal molar of g-59, compound 977 (13.95 g) was obtained with a solid purity > 99.95% as determined by HPLC. Mass spectrum m / z: 863.3324 (theoretical value: 863.3334). Theoretical elemental content (%) C 62 H 45 N3S: C, 86.18; H, 5.25; N, 4.86. Found: C, 86.20; H, 5.24; N, 4.90.

[0274] Synthesis Example 27: Preparation of compound 977

[0275]

[0276] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-63, e-50 with an equal molar amount of e-977, g-50 with an equal molar amount of g-59, compound 977 (13.83 g) was obtained with a solid purity > 99.96% as determined by HPLC. Mass spectrum m / z: 863.3320 (calculated: 863.3334). Theoretical elemental content (%) C 62 H 45 N3S: C, 86.18; H, 5.25; N, 4.86. Found: C, 86.16; H, 5.23; N, 4.90.

[0277] Synthesis Example 28: Preparation of compound 1207

[0278]

[0279] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-435, e-50 with an equal molar amount of e-941, b-8 with an equal molar amount of f-1207, g-50 with an equal molar amount of g-59, compound 1207 (11.19 g) was obtained with a solid purity > 99.91% as determined by HPLC. Mass spectrum m / z: 776.3823 (calculated: 776.3806). Theoretical elemental content (%) C 54 H 24 D 15 N3S: C, 83.47; H, 7.00; N, 5.41. Found: C, 83.50; H, 7.02; N, 5.39.

[0280] Synthesis Example 29: Preparation of compound 1223

[0281]

[0282] Following the procedure for the preparation of compound 50 of synthesis example 2, replacing a-8 with an equal molar amount of a-1223, e-50 with an equal molar amount of e-929, b-8 with an equal molar amount of d-8, g-50 with an equal molar amount of g-59, compound 1223 (14.43 g) was obtained with a solid purity > 99.92% as determined by HPLC. Mass spectrum m / z: 975.4599 (calculated: 975.4586). Theoretical elemental content (%) C 70 H 61 N3S: C, 86.11; H, 6.30; N, 4.30. Found: C, 86.09; H, 6.28; N, 4.33.

[0283] Synthesis Example 30: Preparation of compound 1321

[0284]

[0285] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-1321, e-50 with an equivalent molar of e-1321, g-50 with an equivalent molar of g-59, to obtain compound 1321 (14.85 g) with solid purity > 99.95% by HPLC. Mass spectrum m / z: 963.3660 (theoretical value: 963.3647). Theoretical elemental content (%) C 70 H 49 N3S: C, 87.19; H, 5.12; N, 4.36. Actual elemental content (%) found: C, 87.21; H, 5.09; N, 4.37.

[0286] Synthesis Example 31: Preparation of compound 1333

[0287]

[0288] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-1333, e-50 with an equivalent molar of e-1333, b-8 with an equivalent molar of f-79, g-50 with an equivalent molar of g-59, to obtain compound 1333 (13.66 g) with solid purity > 99.94% by HPLC. Mass spectrum m / z: 961.3472 (theoretical value: 961.3491). Theoretical elemental content (%) C 70 H 47 N3S: C, 87.38; H, 4.92; N, 4.37. Actual elemental content (%) found: C, 87.40; H, 4.89; N, 4.35.

[0289] Synthesis Example 32: Preparation of compound 1399

[0290]

[0291] Following the procedure for the preparation of compound 50 of Synthesis Example 2, replace a-8 with an equivalent molar of a-1399, e-50 with an equivalent molar of e-1399, g-50 with an equivalent molar of g-59, to obtain compound 1399 (12.85 g) with solid purity > 99.94% by HPLC. Mass spectrum m / z: 867.3662 (theoretical value: 867.3647). Theoretical elemental content (%) C 62 H 49N3S: C, 85.78; H, 5.69; N, 4.84. Found ( % ): C, 85.80; H, 5.71; N, 4.86.

[0292] Synthesis Example 33: Preparation of compound 1425

[0293]

[0294] According to the preparation method of compound 50 of synthesis example 2, a-8 was replaced with an equivalent of a-1425, b-8 was replaced with an equivalent of d-8, e-50 was replaced with an equivalent of e-1425, and g-50 was replaced with an equivalent of g-59 to obtain compound 1425 (13.25 g) with a solid purity of ≥ 99.97% detected by HPLC. Mass spectrum m / z: 945.3155 (theoretical value: 945.3137). Theoretical elemental content (%) C 64 H 43 N5O2S: C, 81.25; H, 4.58; N, 7.40. Found ( % ): C, 81.27; H, 4.60; N, 7.37.

[0295] Synthesis Example 34: Preparation of compound 1454

[0296]

[0297] According to the preparation method of compound 50 of synthesis example 2, a-8 was replaced with an equivalent of a-1454, b-8 was replaced with an equivalent of d-8, e-50 was replaced with an equivalent of e-1454, and g-50 was replaced with an equivalent of g-59 to obtain compound 1454 (15.93 g) with a solid purity of ≥ 99.92% detected by HPLC. Mass spectrum m / z: 1007.4137 (theoretical value: 1007.4125). Theoretical elemental content (%) C 68 H 61 N3SSi2: C, 80.99; H, 6.10; N, 4.17. Found ( % ): C, 80.96; H, 6.08; N, 4.20.

[0298] Synthesis Example 35: Preparation of compound 1466

[0299]

[0300] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with an equal molar of c-8, e-50 with an equal molar of e-918, b-8 with an equal molar of f-79, g-50 with an equal molar of g-59, to obtain compound 1466 (13.80 g) with a solid purity > 99.96% as determined by HPLC. Mass spectrum m / z: 919.3068 (calcd 919.3055). Theoretical elemental content (%) C 64 H 45 N3S2: C, 83.54; H, 4.93; N, 4.57. Found elemental content (%) C, 83.52; H, 4.89; N, 4.60.

[0301] Synthesis Example 36: Preparation of compound 1503

[0302]

[0303] Following the procedure for the preparation of compound 848 of synthesis example 23, replace C-59 with an equal molar C-1503, to obtain compound 1503 (14.25 g) with a solid purity > 99.93% as determined by HPLC. Mass spectrum m / z: 975.2759 (calcd 975.2776). Theoretical elemental content (%) C 66 H 45 N3S3: C, 81.20; H, 4.65; N, 4.30. Found elemental content (%) C, 81.18; H, 4.62; N, 4.29.

[0304] Synthesis Example 37: Preparation of compound 1546

[0305]

[0306] Following the procedure for the preparation of compound 50 of synthesis example 2, replace a-8 with an equal molar of a-1546, e-50 with an equal molar of e-1546, b-8 with an equal molar of f-1546, g-50 with an equal molar of g-1546, to obtain compound 1546 (11.47 g) with a solid purity > 99.92% as determined by HPLC. Mass spectrum m / z: 830.3258 (calcd 830.3271). Theoretical elemental content (%) C 57 H 38 D3N5S: C, 82.38; H, 5.34; N, 8.43. Found elemental content (%) C, 82.40; H, 5.32; N, 8.45.

[0307] Synthesis Example 38: Preparation of compound 1564

[0308]

[0309] According to the preparation method of compound 8 in synthesis example 1, a-8 is replaced by equimolar a-1564, c-8 is replaced by equimolar c-1564, d-8 is replaced by equimolar b-8, e-8 is replaced by equimolar e-929, f-8 is replaced by equimolar b-173, g-8 is replaced by equimolar g-1564, to obtain compound 1564 (10.84 g), solid purity ≥ 99.90% detected by HPLC. Mass spectrum m / z: 873.3730 (theoretical value: 873.3713). Theoretical elemental content (%) C 57 H 31 D 12 N5S2: C, 78.31; H, 6.34; N, 8.01. Measured elemental content (%) C, 78.29; H, 6.32; N, 8.04.

[0310] Synthesis Example 39: Preparation of compound 1586

[0311]

[0312] According to the preparation method of compound 50 in synthesis example 2, a-8 is replaced by equimolar a-1586, e-50 is replaced by equimolar e-1586, g-50 is replaced by equimolar g-59, to obtain compound 1586 (13.19 g), solid purity ≥ 99.95% detected by HPLC. Mass spectrum m / z: 878.4348 (theoretical value: 878.4348). Theoretical elemental content (%) C 64 H 54 N4: C, 87.44; H, 6.19; N, 6.37. Measured elemental content (%) C, 87.43; H, 6.20; N, 6.39.

[0313] [Device Example 1]

[0314] First, the ITO substrate is cleaned with ultrasonic cleaning in distilled water for 3 times, each time for 15 minutes, after the distilled water cleaning, isopropanol, acetone, methanol and other solvents are used for ultrasonic cleaning in turn, each time for 10 minutes, after the cleaning, drying is performed at 120°C.

[0315] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate HI-1 as a hole injection layer on an ITO substrate which had been cleaned, at a thickness of 10 nm; to evaporate compound 8 as a hole transport layer on the hole injection layer, at a thickness of 85 nm; to evaporate GH-1:GH-2:GD-1 = 47:47:6 (mass ratio) as a light emitting layer on the hole transport layer, at a thickness of 40 nm; to evaporate HB-1 as a hole blocking layer on the light emitting layer, at a thickness of 35 nm; to evaporate Alq3 as an electron transport layer on the hole blocking layer, at a thickness of 30 nm; to evaporate LiF as an electron injection layer on the electron transport layer, at a thickness of 1.0 nm; and to evaporate Al as a cathode on the electron injection layer, at a thickness of 130 nm.

[0316]

[0317] [Device Example 2-39]

[0318] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate compound 50, compound 59, compound 63, compound 79, compound 96, compound 112, compound 137, compound 173, compound 236, compound 369, compound 427, compound 435, compound 455, compound 507, compound 549, compound 581, compound 590, compound 626, compound 720, compound 770, compound 775, compound 848, compound 918, compound 929, compound 941, compound 977, compound 1207, compound 1223, compound 1321, compound 1333, compound 1399, compound 1425, compound 1454, compound 1466, compound 1503, compound 1546, compound 1564, compound 1586 of the present application, respectively, as a hole transport layer material instead of compound 8 in Device Example 1, and an organic electroluminescence device was produced by the same production method as in Device Example 1, except for this.

[0319] [Comparative Device Examples 1-4]

[0320] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate comparative compound 1, comparative compound 2, comparative compound 3, or comparative compound 4, respectively, as a hole transport layer material instead of compound 8 in Device Example 1, and an organic electroluminescence device was produced by the same production method as in Device Example 1, except for this.

[0321] The test software, computer, K2400 digital source meter produced by Keithley Company of USA and PR788 spectral scanning luminance meter of PhotoResearch Company of USA are combined into an integrated IVL test system to test the luminous efficiency of the organic electroluminescent device. The life test adopts M6000 OLED life test system of McScience Company. The test environment is atmospheric environment, and the temperature is room temperature.

[0322] The test results of the luminous characteristics of the organic electroluminescent devices obtained in device embodiments 1 to 39 and comparative embodiments 1 to 4 are shown in Table 1.

[0323]

[0324]

[0325] [Device embodiment 40]

[0326] Firstly, the ITO substrate is cleaned in distilled water for 3 times, each time for 15 minutes of ultrasonic cleaning. After the distilled water cleaning, isopropanol, acetone, methanol and the like are used for ultrasonic cleaning in sequence, each time for 10 minutes of ultrasonic cleaning. After the cleaning, drying is performed at 120°C.

[0327] The vacuum evaporation method is adopted to evaporate HI-1 on the cleaned ITO substrate as a hole injection layer, and the evaporation thickness is 10 nm. HT-1 is evaporated on the hole injection layer as a first hole transport layer, and the evaporation thickness is 25 nm. Compound 8 is evaporated on the first hole transport layer as a second hole transport layer, and the evaporation thickness is 60 nm. RH-1:RD-1=98:2 (mass ratio) is evaporated on the second hole transport layer as a light-emitting layer, and the evaporation thickness is 40 nm. HB-1 is evaporated on the light-emitting layer as a hole blocking layer, and the evaporation thickness is 40 nm. Alq3 is evaporated on the hole blocking layer as an electron transport layer, and the evaporation thickness is 30 nm. LiF is evaporated on the electron transport layer as an electron injection layer, and the evaporation thickness is 1.0 nm. Al is evaporated on the electron injection layer as a cathode, and the evaporation thickness is 130 nm, so as to prepare an organic electroluminescent device.

[0328] [Device embodiments 41-78]

[0329] An organic electroluminescent device was produced in the same manner as in Device Example 40, except for using compound 50, compound 59, compound 63, compound 79, compound 96, compound 112, compound 137, compound 173, compound 236, compound 369, compound 427, compound 435, compound 455, compound 507, compound 549, compound 581, compound 590, compound 626, compound 720, compound 770, compound 775, compound 848, compound 918, compound 929, compound 941, compound 977, compound 1207, compound 1223, compound 1321, compound 1333, compound 1399, compound 1425, compound 1454, compound 1466, compound 1503, compound 1546, compound 1564, compound 1586 of the present application instead of compound 8 as the second hole transport layer material, respectively.

[0330] [Comparative Device Examples 5 to 8]

[0331] An organic electroluminescent device was produced in the same manner as in Device Example 40, except for using comparative compound 1, comparative compound 2, comparative compound 3 or comparative compound 4 instead of compound 8 as the second hole transport layer material, respectively.

[0332] The results of the luminescence characteristics test of the organic electroluminescent devices obtained in Device Examples 40 to 78 and Comparative Examples 5 to 8 of the present application are shown in Table 2 below.

[0333]

[0334]

[0335] As can be seen from the data in Table 1 and Table 2, the triamine derivatives represented by Formula I of the present application, when applied to an organic electroluminescent device, can balance the transport of carriers, increase the recombination probability of excitons in the light-emitting layer, and have good thermal stability and good film-forming properties and are not easy to crystallize, thus effectively improving the luminous efficiency and service life of the device when used as a hole transport layer material and a second hole transport layer material.

[0336] [Device Example 79]

[0337] First, the ITO / Ag / ITO substrate was cleaned with ultrasonic washing in distilled water for 3 times, each time for 15 minutes. After the distilled water cleaning, the substrate was cleaned with ultrasonic washing in isopropanol, acetone, methanol and the like, each time for 10 minutes. After the cleaning, the substrate was dried at 120°C.

[0338] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate HI-1 as a hole injection layer on an ITO / Ag / ITO substrate which had been cleaned, with an evaporation thickness of 15 nm; HT-1 was evaporated as a hole transport layer on the hole injection layer, with an evaporation thickness of 80 nm; GH-3:GH-4:GD-2 = 46:46:8 (mass ratio) was evaporated as a light emitting layer on the hole transport layer, with an evaporation thickness of 45 nm; HB-2 was evaporated as a hole blocking layer on the light emitting layer, with an evaporation thickness of 35 nm; Liq was evaporated as an electron transport layer on the hole blocking layer, with an evaporation thickness of 25 nm; LiF was evaporated as an electron injection layer on the electron transport layer, with an evaporation thickness of 0.8 nm; Mg:Ag = 1:9 (doping mass ratio) was evaporated as a cathode on the electron injection layer, with an evaporation thickness of 12 nm; and Compound 8 was evaporated as a cover layer on the cathode, with an evaporation thickness of 70 nm, thereby producing an organic electroluminescence device.

[0339] [Device Example 80-103]

[0340] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate Compound 50, Compound 59, Compound 79, Compound 112, Compound 137, Compound 236, Compound 369, Compound 507, Compound 549, Compound 581, Compound 590, Compound 626, Compound 775, Compound 918, Compound 929, Compound 941, Compound 977, Compound 1207, Compound 1321, Compound 1333, Compound 1425, Compound 1454, Compound 1466, Compound 1503 of the present application as a cover layer material instead of Compound 8 in Device Example 79, and the same production method as Device Example 79 was used, thereby producing an organic electroluminescence device.

[0341] [Comparative Device Example 9]

[0342] An organic electroluminescence device was produced in the following manner. A vacuum evaporation method was used to evaporate Compound 5 of the present application as a cover layer material instead of Compound 8 in Device Example 79, and the same production method as Device Example 79 was used, thereby producing an organic electroluminescence device.

[0343] The results of the luminescence characteristics test of the organic electroluminescence devices obtained in Device Examples 79-98 and Comparative Example 9 of the present application are shown in Table 3 below.

[0344]

[0345]

[0346] According to the data results of Table 3, it can be seen that the triamine derivative represented by Formula I of the present application, when applied to an organic electroluminescent device as a cover layer material, can effectively reduce the total reflection phenomenon of light inside the device, greatly improve the light extraction efficiency, and thus improve the luminous efficiency of the device and prolong the service life.

[0347] It should be noted that the present application is particularly described with individual embodiments, but those skilled in the art can make various forms or details of improvements to the present application without departing from the principles of the present application, and these improvements also fall within the protection scope of the present application.

Claims

1. A triamine derivative, characterized in that, the t1 is selected from any one of O, S, N(R); wherein Ar1to Ar6are the same or different from each other, at least one of which is selected from the group consisting of is selected from any one of the group consisting of the R is the same or different from each other, selected from any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl group: phenyl, biphenyl, naphthyl; the a1 is selected from 0, 1, 2, 3 or 4, the a2 is selected from 0, 1 or 2, the a3 is selected from 0, 1, 2 or 3, and the a5 is selected from 0, 1, 2, 3, 4, 5 or 6; R a , R b are the same or different from each other and are selected from hydrogen, deuterium, or any one of the following groups, which are unsubstituted or substituted with one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl; the rest of Ar1-Ar6 are the same or different from each other, selected from any one of the following groups, the t2 is selected from any one of O, S, N(R0); the R0 is the same or different from each other, selected from any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl group: phenyl, biphenyl, naphthyl; and any one of the Ar1 and Ar2, Ar3 and Ar4, Ar5 and Ar6 is not simultaneously substituted with a tert-butyl group; said R ca each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyle, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl or triphenylsilyl; said R cb each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: phenyl; said R cc each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl; said R c each independently of one another, selected from any one of hydrogen, deuterium; said R d each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: phenyl; said d1 is selected from 0, 1, 2, 3, 4 or 5, said d2 is selected from 0, 1, 2, 3 or 4, said d3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 1 1, said d6 is selected from 0, 1, 2 or 3, said d 11 selected from 0 or 1, said d 12 selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1, 12 or 13; the L1-L6 are the same or different from each other, selected from a single bond or any one of the following groups, the e1 is selected from 0, 1, 2, 3 or 4, and the e2 is selected from 0, 1, 2 or 3; said R e each independently of one another, selected from any one of hydrogen, deuterium; the R1-R3 are the same or different from each other, selected from any one of hydrogen, deuterium, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group; the "substituted or unsubstituted" in the above-mentioned "substituted or unsubstituted" is selected from deuterium; the t1 is selected from any one of O, S, N(R); with the proviso that the triamine derivative is not 2. A triamine derivative according to claim 1, wherein The is selected from any one of the following groups of radicals, the R is the same or different from each other, selected from any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl group: phenyl; the b1 is selected from 1, 2, 3, 4 or 5, the b2 is selected from 1, 2, 3 or 4, and the b3 is selected from 1, 2, 3, 4, 5, 6 or 7. the rest of Ar1-Ar6 are the same or different from each other, selected from any one of the following groups, 3. A triamine derivative according to claim 1, characterized in that, the triamine derivative is selected from any one of the following groups, said R ca each other or different from each other, are selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclobutane, cyclopentane, cyclohexane, adamantane.

4. A triamine derivative, characterized in that, the organic layer comprises any one or more of the triamine derivatives of claim 4.

5. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being positioned between the anode and the cathode or outside of either of the anode and the cathode, characterized by, the organic layer is located between the anode and the cathode, and the organic layer comprises a hole transport region, wherein the hole transport region comprises any one or more of the triamine derivatives of claim 4.

6. An organic electroluminescent device according to claim 5, characterized in that the organic layer is located outside of any one of the anode and the cathode, and the organic layer comprises a capping layer, wherein the capping layer comprises any one or more of the triamine derivatives of claim 4.

7. An organic electroluminescent device according to claim 5, characterized in that the organic layer comprises any one or more of the triamine derivatives, and the triamine derivative is selected from any one of the following groups, 8. An organic electroluminescent device comprising an anode, an organic layer, and a cathode, the organic layer being positioned between the anode and the cathode or outside of either of the anode and the cathode, characterized by, the t1 is selected from any one of O, S, N(R); wherein Ar1to Ar6are the same or different from each other, at least one of which is selected from the group consisting of is selected from any one of the group consisting of the R is the same or different from each other, selected from any one of the following groups substituted or unsubstituted with one or more deuterium, C1-C6 alkyl group: phenyl, biphenyl, naphthyl; the a1 is selected from 0, 1, 2, 3 or 4, the a2 is selected from 0, 1 or 2, the a3 is selected from 0, 1, 2 or 3, and the a5 is selected from 0, 1, 2, 3, 4, 5 or 6; R a , R b are the same or different from each other and are selected from hydrogen, deuterium, or any one of the following groups, which are unsubstituted or substituted with one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl; ​ the rest of Ar1~Ar6are the same as or different from each other, selected from any one of the following groups, said t2is selected from any one of O, S, N(R0); said R0are the same as or different from each other, selected from any one of the following groups substituted or unsubstituted by one or more deuterium, C1~C6alkyl: said R ca each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropanyl, cyclobutanyl, cyclopentanyl, cyclohexanyle, adamantyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl or triphenylsilyl; said R cb each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: phenyl; said R cc each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl; said R c any one of hydrogen, deuterium; said R d each independently of one another, selected from hydrogen, deuterium, or any one of the following groups unsubstituted or substituted by one or more deuterium: phenyl; said d1 is selected from 0, 1, 2, 3, 4 or 5, said d2 is selected from 0, 1, 2, 3 or 4, said d3 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, said d4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 1 1, said d6 is selected from 0, 1, 2 or 3, said d 11 is selected from 0 or 1, said d 12 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1, 12 or 13; and any one of Ar1and Ar2, Ar3and Ar4, Ar5and Ar6is not simultaneously substituted by t-butyl; said L1~L6are the same as or different from each other, selected from a single bond or any one of the following structures, said R e any one of hydrogen, deuterium; said e1is selected from 0, 1, 2, 3 or 4, said e2is selected from 0, 1, 2 or 3; said R1~R3are the same as or different from each other, selected from any one of hydrogen, deuterium, substituted or unsubstituted methyl, substituted or unsubstituted ethyl; said "substituted or unsubstituted" in the substituted group is selected from deuterium; with the proviso that the triamine derivative is not 9. An organic electroluminescent device according to claim 8, characterized in that The is selected from any one of the following groups of radicals, said t1is selected from any one of O, S, N(R); said R are the same as or different from each other, selected from any one of the following groups substituted or unsubstituted by one or more deuterium, C1~C6alkyl: said b1is selected from 1, 2, 3, 4 or 5, said b2is selected from 1, 2, 3 or 4, said b3is selected from 1, 2, 3, 4, 5, 6 or 7.

10. An organic electroluminescent device according to claim 8, characterized in that the rest of Ar1~Ar6are the same as or different from each other, selected from any one of the following groups, said R ca , independently of each other, are selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, cyclobutane, cyclopentane, cyclohexane, adamantane.

11. An organic electroluminescent device according to any of claims 8 to 10, characterised in that said organic layer is located between said anode and said cathode, said organic layer comprises a hole transport region, said hole transport region comprises any one or more than one of the triamine derivatives according to any one of claims 8-10.

12. An organic electroluminescent device according to any of claims 8 to 10, characterised in that said organic layer is located outside of any one of said anode and said cathode, said organic layer comprises a capping layer, said capping layer comprises any one or more than one of the triamine derivatives according to any one of claims 8-10.

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