Star-type triamine derivative and organic electroluminescent device thereof

Abstract

The invention provides a star-shaped triamine derivative and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescence. The star-shaped triamine derivative provided by the invention has efficient hole mobility and proper HOMO energy level, and is applied to an organic electroluminescent device as a hole transport layer material, so that the transport balance of holes and electrons among organic layers is increased, the electrons can be effectively blocked in a light-emitting layer, and the light-emitting efficiency of the organic electroluminescent device is improved. In addition, the material is used as a covering layer material and has good refractive index, good film forming property and high glass transition temperature, so that the extraction efficiency of light in the device is improved, the accumulation of Joule heat in the device is reduced, the luminous efficiency of the device is remarkably improved, and the service life of the device is remarkably prolonged. Good application effects and industrialization prospects are realized.

Description

Technical Field

[0001] The present invention relates to the technical field of organic electroluminescent materials, in particular to a star-shaped triamine derivative and an organic electroluminescent device thereof. Background Art

[0002] Organic light-emitting diodes (OLEDs), also known as organic electroluminescent diodes, are devices that, under the influence of an external electric field, inject and transfer electrons and holes from the cathode and anode into the organic layer of the organic photoelectric material, respectively. These electrons and holes recombine within the light-emitting layer to produce excitons. The excitons transfer energy to the organic light-emitting molecules, causing them to transition from the ground state to an excited state. The excited state molecules are unstable, and when the excited molecules return to the ground state, the energy is released as light, producing luminescence. OLEDs offer advantages such as fast response, wide viewing angle, thin and lightweight design, wide operating temperature range, low energy consumption, high clarity, strong flexibility, and the ability to realize large-area, full-color flat-panel displays. They are widely used in numerous fields, including display and lighting, making them a research hotspot in recent years and offering excellent commercial and market prospects.

[0003] With the development of organic electroluminescent devices, the structure of organic electroluminescent devices is also constantly improving. Organic electroluminescent devices can be divided into single-layer devices, double-layer devices and multi-layer devices according to their structure. The classic device structure is usually a sandwich structure consisting of a cathode, an anode and an organic functional layer. 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, a covering layer and other functional layers.

[0004] High-quality organic electroluminescent devices need to meet the characteristics of high luminous efficiency and long service life. However, the development of organic electroluminescent materials is not yet perfect, and there are still many problems in preparing high-quality organic electroluminescent devices. The hole transport layer acts as a connecting layer between the anode and the light-emitting layer, better transporting holes injected from the anode to the light-emitting layer and, to a certain extent, blocking the diffusion of electrons from the light-emitting layer to the hole transport layer, thereby better confining electrons within the light-emitting layer and achieving maximum carrier recombination. It also reduces the energy barrier for hole injection and improves the hole injection efficiency. However, hole transport layer materials in the prior art have many problems, such as low triplet energy levels, which increase the energy barrier for hole injection and transport, low glass transition temperature, poor thermal stability, poor film forming properties, low hole mobility, and unbalanced hole and electron transport. There is a plasmon resonance effect between the capping layer material and the cathode material, which reduces the light extraction efficiency within the device, causing some light to be confined within the device, resulting in heat accumulation and a reduced device life. In addition, two or more independent light-emitting parts are connected in series through a charge generation layer (CGL). The electrons and holes generated by the CGL are injected into adjacent light-emitting units respectively. Conventional n-type doped layers / p-type doped layers serve as connecting layers between light-emitting units, improving the recombination of holes / electrons into excitons within the light-emitting units. In order to obtain organic electroluminescent devices with high luminous efficiency and long service life, it is crucial to design organic electroluminescent materials with suitable HOMO energy levels, high hole mobility, high glass transition temperature, good thermal stability and good film-forming properties. Summary of the Invention

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

[0006] The present invention provides a star-shaped triamine derivative having a structure as shown in Formula I.

[0007]

[0008] In formula I, the Ar1 is selected from the group shown in formula II;

[0009] Ar2 is selected from the group shown in formula III;

[0010]

[0011] The Ar3 to Ar6 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted by one or more R3: a C6 to C30 aryl group, a fused ring group of a C6 to C30 aromatic ring and a C3 to C30 aliphatic ring, and a C2 to C30 heteroaryl group;

[0012] R3 is selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0013] Said X is selected from O or S;

[0014] The ring A and ring B are the same or different and are selected from a C6-C30 aromatic ring, which is absent, substituted or unsubstituted; when X is selected from O, the ring A and ring B are not both selected from none;

[0015] R1 and R2 are the same as or different from each other and are selected from any one of hydrogen, cyano, nitro, trifluoromethyl, halogen, 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 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0016] R a ~R c are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, 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 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0017] The a is selected from 0, 1, 2, 3, 4, 5 or 6. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to form a substituted or unsubstituted ring; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s can be connected to form a substituted or unsubstituted ring;

[0018] The L1 to L6 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused cyclic group, a substituted or unsubstituted C2-C30 heteroarylene group, and combinations thereof;

[0019] Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R a 、R b 、R c At least one of the compounds contains deuterium.

[0020] The present invention 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 contains any one or more of the star-shaped triamine derivatives.

[0021] Beneficial effects: The star-shaped triamine derivative represented by formula I provided by the present invention has high hole mobility and a suitable HOMO energy level, can effectively reduce the energy barrier in the hole transport process, is beneficial to the injection and transport of holes in the organic layer, and increases the recombination probability of excitons in the light-emitting layer. When used as a hole transport layer material in an organic electroluminescent device, the luminous efficiency and service life of the device are significantly improved. In addition, when used as a covering layer material in an organic electroluminescent device, due to its high refractive index, good film-forming properties, high thermal stability, and high glass transition temperature, the performance of the device is greatly improved. DETAILED DESCRIPTION

[0022] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0023] In the compounds of the present invention, any atom not designated as a particular isotope encompasses any stable isotope of that atom and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0024] In the present specification, "*" means a portion connecting to another substituent.

[0025] In this specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any one of the corresponding optional positions of the ring. For example, Can represent Can represent Can represent And so on.

[0026] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the ring. For example, Can represent Can represent And so on.

[0027] Examples of the halogen atom described in the present invention may include fluorine, chlorine, bromine or iodine.

[0028] The alkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, preferably 1 to 12 carbon atoms, more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0029] The alkenyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from an olefin molecule, which can be a straight chain alkenyl group or a branched chain alkenyl group, preferably having 2 to 25 carbon atoms, preferably 2 to 12 carbon atoms, and more preferably 2 to 6 carbon atoms. The alkenyl group can be substituted or unsubstituted. Specific examples include vinyl, 1-propenyl, isopropenyl, butenyl, pentenyl, 3-methyl-1-butenyl, allyl, 1-phenylvinyl-1-yl, styryl, etc., but are not limited thereto.

[0030] The cycloalkyl group of the present invention refers to a monovalent group obtained by removing a hydrogen atom from a cyclic alkane molecule, preferably having 3 to 25 carbon atoms, preferably 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and particularly preferably 3 to 6 carbon atoms. The cycloalkyl group may be substituted or unsubstituted. The cycloalkyl group includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, and norbornyl.

[0031] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R k )3 groups, wherein each R kThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic fused ring group, substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaromatic fused ring group. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl. The number of carbon atoms in 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 in 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 in the aryl group is preferably 6 to 30, more preferably 6 to 18, and particularly preferably 6 to 12. Preferably, each R k The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. Preferably, the "substituted or unsubstituted C3-C25 silyl group" refers to a silyl group substituted by a substituted or unsubstituted C3-C25 alkyl or aryl group, which is preferably substituted by three alkyl groups or three aryl groups. Examples of the “substituted or unsubstituted silyl group”, especially the “substituted or unsubstituted C3-C25 silyl group” may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl and the like, but are not limited thereto.

[0032] The aryl group described in the present invention refers to a monovalent group obtained by removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule, which can be a monocyclic aryl group, a polycyclic aryl group or a condensed aryl group, preferably having 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 refers to an aryl group having only one aromatic ring in the molecule, such as phenyl, etc., but not limited thereto; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, quaterphenyl, etc., but not limited thereto; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused to each other by sharing two adjacent carbon atoms, such as naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, triphenylene, fluoranthenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, 9,9'-spirobifluorenyl, etc., but are not limited thereto.

[0033] The heteroaryl group of the present invention is a general term for a group in which one or more aromatic carbon atoms in an aromatic group are replaced by a heteroatom, wherein the heteroatom includes but is not limited to O, S, N, Si or P atoms, and preferably has 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The attachment point of the heteroaryl group can be located on a ring-forming carbon atom or a ring-forming heteroatom, and the heteroaryl group can be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed ring heteroaryl group. The heteroaryl group can be substituted or unsubstituted. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc.; the fused ring heteroaryl groups include, but are not limited to, quinolyl, isoquinolyl, benzoquinolyl, benzoisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, The invention also includes benzophenone, phenanthroline, naphthyridinyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiophenyl, benzodibenzothiophenyl, dibenzoxazolyl, dibenzimidazolyl, dibenzothiazolyl, carbazolyl, benzocarbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthryl, spirofluorenylthioanthryl, etc., but is not limited thereto.

[0034] The aliphatic ring described herein refers to a cyclic hydrocarbon with aliphatic properties, containing a 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, and even more preferably 3 to 7 carbon atoms. It can form a monocyclic hydrocarbon or a polycyclic hydrocarbon and can be fully unsaturated or partially unsaturated. The aliphatic ring can be substituted or unsubstituted. Specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopropene, cyclobutene, cyclopentene, cyclohexene, and cycloheptene. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; and several rings can be connected to form a cage-like structure.

[0035] The fused ring of an aromatic ring and an aliphatic ring described in the present invention refers to a ring formed by condensing one or more aromatic rings and one or more aliphatic rings in a molecule 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. 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 an aromatic ring and an aliphatic ring can be substituted or unsubstituted. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0036] The arylene group described in the present invention refers to the general term for the divalent group left after two hydrogen atoms are removed from the aromatic core carbon of the aromatic hydrocarbon molecule. It can be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, preferably having 6 to 30 carbon atoms, more preferably 6 to 22 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Regarding the above-mentioned arylene group, as a monocyclic arylene group, it can be a phenylene group, etc., but it is not limited thereto. The arylene group can be substituted or unsubstituted. As the above-mentioned polycyclic arylene group, it can be a biphenylene group, a terphenylene group, a quaterphenylene group, etc., but it is not limited thereto. As the above-mentioned condensed ring arylene group, it can be a naphthylene group, anthrylene group, phenanthrenyl group, pyrenyl group, fluorenyl group, spirofluorenyl group, triphenylene group, perylene group, fluoranthenyl group, fluoren ... etc., but not limited thereto.

[0037] The heteroarylene group described in the present invention refers to a general term for a divalent group remaining after removing two hydrogen atoms from the core carbon of an aromatic heterocycle composed of carbon and heteroatoms. The heteroatom may be one or more of N, O, S, Si, and P. It may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a condensed-ring heteroarylene group, preferably having 2 to 30 carbon atoms, more preferably 2 to 22 carbon atoms, even more preferably 2 to 20 carbon atoms, and most preferably 3 to 12 carbon atoms. The heteroarylene group may be substituted or unsubstituted. Examples may include pyridylene, pyrimidylene, pyrazinylene, pyridazinylene, triazinylene, thienylene, pyrrolylene, furylene, pyranylene, oxazolylene, thiazolylene, imidazolylene, benzoxazolylene, benzothiazolylene, benzimidazolylene, carbazolylene, benzocarbazolylene, acridinylene, xanthenylene, thioanthenylene, phenazinylene, phenothiazinylene, phenoxazinylene, indolylene, quinolylene, isoquinolylene, benzothienylene, benzofuranylene, dibenzofuranylene, dibenzothienylene, quinoxalinylene, quinazolinylene, naphthyridinylene, purinylene, o-phenanthrolineylene, and the like, but are not limited thereto.

[0038] The fused aromatic and aliphatic ring sub-groups described herein are fused aromatic and aliphatic rings with two linking sites, i.e., divalent groups. The description of the fused aromatic and aliphatic ring sub-groups described above applies to these sub-groups, except that they are divalent groups.

[0039] In the context of "substituted or unsubstituted" herein, "unsubstituted" means that no hydrogen atom on the group is replaced by any substituent; "substituted" means that at least one hydrogen atom on the group is replaced by a substituent, and the position of the substitution is not limited. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different.

[0040] The substituents in the "substituted or unsubstituted" of the present invention may be the same as or different from each other and are selected from any one of deuterium, cyano, nitro, trifluoromethyl, halogen atoms, 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 C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring, preferably deuterium, cyano, halogen atoms, trifluoromethyl, halogen atoms, 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 C2-C12 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring and C3-C30 aliphatic ring fused ring. alkyl, C1-C12 alkyl, C3-C12 cycloalkyl, C3-C25 silyl, C6-C30 aryl, C2-C30 heteroaryl, specific examples of which may include deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, deuterated methyl, deuterated isopropyl, deuterated tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, phenyl, biphenyl, terphenyl, tolyl, pentadeuterated phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, triphenylene, 1,2-dimethyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1,2-diphenyl-1 The invention also includes oxazolyl, oxazolyl, thiazolyl, benzothiazolyl, benzotriazolyl, benzoimidazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenothiazinyl, phenoxazinyl, and the like, but is not limited thereto.

[0041] The term "linked to form a ring" as used herein refers to two groups being linked to each other via a chemical bond and optionally aromatized. For example:

[0042]

[0043] In this specification, the ring formed by connection 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 condensed ring, etc., 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, etc., but are not limited thereto.

[0044] The present invention provides a star-shaped triamine derivative having a structure as shown in Formula I.

[0045]

[0046] In formula I, the Ar1 is selected from the group shown in formula II;

[0047] Ar2 is selected from the group shown in formula III;

[0048]

[0049] The Ar3 to Ar6 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted by one or more R3: a C6 to C30 aryl group, a fused ring group of a C6 to C30 aromatic ring and a C3 to C30 aliphatic ring, and a C2 to C30 heteroaryl group;

[0050] R3 is selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0051] Said X is selected from O or S;

[0052] The ring A and ring B are the same or different and are selected from a C6-C30 aromatic ring, which is absent, substituted or unsubstituted; when X is selected from O, the ring A and ring B are not both selected from none;

[0053] R1 and R2 are the same as or different from each other and are selected from any one of hydrogen, cyano, nitro, trifluoromethyl, halogen, 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 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0054] R a ~R c are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, 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 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl;

[0055] The a is selected from 0, 1, 2, 3, 4, 5 or 6. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to form a substituted or unsubstituted ring; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s can be connected to form a substituted or unsubstituted ring;

[0056] The L1 to L6 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused cyclic group, a substituted or unsubstituted C2-C30 heteroarylene group, and combinations thereof;

[0057] Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R a 、R b 、R c At least one of the compounds contains deuterium.

[0058] Preferably, at least one of Ar3, Ar4, Ar5, and Ar6 contains deuterium.

[0059] Preferably, at least one of L1, L2, L3, L4, L5, and L6 contains deuterium.

[0060] Preferably, the R a 、R b 、R cMore preferably, at least one of the R a 、R b 、R c All are selected from deuterium.

[0061] Preferably, the “at least one” mentioned in the present invention includes one, two, three, four, five, six or more.

[0062] Preferably, the formula II is selected from any one of the groups shown below;

[0063]

[0064]

[0065] The R1s are the same as or different from each other and are selected from hydrogen, cyano, trifluoromethyl, halogen, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl;

[0066] The b1 is selected from 0, 1, 2, 3, 4 or 5, the b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the b4 is selected from 0, 1, 2 or 3, the b5 is selected from 0, 1, 2, 3 or 4, the b6 is selected from 0, 1, 2, 3, 4, 5 or 6, and the b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0067] Preferably, the formula III is selected from any one of the groups shown below;

[0068]

[0069] The R2 are the same as or different from each other and are selected from hydrogen, cyano, trifluoromethyl, halogen, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl;

[0070] The c1 is selected from 0, 1, 2, 3, 4 or 5, the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the c4 is selected from 0, 1, 2 or 3, the c5 is selected from 0, 1, 2, 3 or 4, the c6 is selected from 0, 1, 2, 3, 4, 5 or 6, and the c7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0071] Preferably, the Ar3 to Ar6 are the same as or different from each other and are selected from any one of the groups shown below;

[0072]

[0073] Said r and t1 are the same or different from each other and are selected from CH or N atoms. When r is bonded to other groups, said r is selected from C atoms;

[0074] Said t2 is selected from O, S, N (R z )

[0075] Said t3 is selected from O, S, C (R x R y )、N(R z )

[0076] The ring C is selected from a substituted or unsubstituted C3 to C7 aliphatic ring;

[0077] The R3, R4, R x 、R yare the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R x 、R y They may be connected to each other to form a substituted or unsubstituted ring; or the R x 、R y Can directly bond with any one of L3 to L6;

[0078] The R z Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or said R z Can directly bond with any one of L3 to L6;

[0079] The d1 is selected from 0, 1, 2, 3, 4 or 5, the d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the d3 is selected from 0, 1, 2 or 3, the d4 is selected from 0, 1, 2, 3 or 4, and the d5 is selected from 0 or 1. When two or more R3 are present, the two or more R3 are the same as or different from each other, or two adjacent R3 can be connected to each other to form a substituted or unsubstituted ring; when two or more R4 are present, the two or more R4 are the same as or different from each other.

[0080] Preferably, the Ar3 to Ar6 are the same as or different from each other and are selected from any one of the groups shown below;

[0081]

[0082]

[0083]

[0084] R3 and R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl, or benzothiophenyl;

[0085] The f1 is selected from 0, 1, 2, 3, 4, or 5, the f2 is selected from 0, 1, 2, 3, or 4, the f3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, the f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, the f6 is selected from 0, 1, 2, or 3, the f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, the f8 is selected from 0, 1, 2, 3, 4, 5, or 6, the f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, the f 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said f 11 is selected from 0, 1 or 2, said f 12 Select from 0 or 1.

[0086] Preferably, one, two, three or four of the Ar3 to Ar6 are selected from any one of the following groups:

[0087]

[0088] Wherein, z1 is selected from 0 or 4, and z2 is selected from 0 or 6.

[0089] Preferably, the L1 to L6 are the same as or different from each other and are selected from a single bond or any one of the groups shown below;

[0090]

[0091] The R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, or benzocyclohexyl;

[0092] The e1 is selected from 0, 1, 2, 3 or 4, the e2 is selected from 0, 1, 2 or 3, the e3 is selected from 0, 1 or 2, the e4 is selected from 0, 1, 2, 3, 4, 5 or 6, the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the e7 is selected from 0 or 1.

[0093] Preferably, one, two, three, four, five or six of L1 to L6 are selected from any one of the following groups:

[0094]

[0095] Wherein, said z1 is selected from 0 or 4.

[0096] Preferably, the star-shaped triamine derivative is selected from any one of the structures shown below;

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The above lists some specific structural forms of the star-shaped triamine derivatives represented by Formula I of the present invention, but the present invention is not limited to these chemical structures listed. All those based on the structure shown in Chemical Formula I and having substituents as defined above should be included.

[0120] The present invention 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 either the anode or the cathode, and the organic layer comprises any one or more of the star-shaped triamine derivatives.

[0121] Preferably, the organic layer of the present invention is located between the anode and the cathode, and includes at least one layer of a hole transport region, a light emitting layer, and an electron transport region.

[0122] Preferably, the hole transport region described in the present invention comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and at least one of the hole injection layer, the hole transport layer, and the electron blocking layer comprises any one or more of the star-shaped triamine derivatives described in the present invention.

[0123] Preferably, the hole transport region of the present invention comprises at least one of a hole injection layer and a hole transport layer, and at least one of the hole injection layer and the hole transport layer comprises any one or more of the star-shaped triamine derivatives of the present invention.

[0124] Preferably, the hole transport region of the present invention comprises at least one of a hole transport layer and an electron blocking layer, and at least one of the hole transport layer and the electron blocking layer comprises any one or more of the star-shaped triamine derivatives of the present invention.

[0125] Preferably, the hole transport region of the present invention comprises a hole transport layer, and the hole transport layer comprises any one or more of the star-shaped triamine derivatives of the present invention.

[0126] Preferably, the hole transport layer described in the present invention comprises a first hole transport layer and a second hole transport layer, the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer comprises any one or more of the star-shaped triamine derivatives described in the present invention.

[0127] Preferably, the organic layer of the present invention is located between the anode and the cathode, the organic layer comprises two or more light-emitting parts and a charge generation layer, the first light-emitting part is located between the anode and the cathode, the second light-emitting part is located between the first light-emitting part and the cathode, the charge generation layer is located between the first light-emitting part and the second light-emitting part, and the charge generation layer comprises any one or more of the star-shaped triamine derivatives described in the present invention.

[0128] Preferably, the charge generation layer is composed of an N-type charge generation layer arranged adjacent to the first light-emitting portion and a P-type charge generation layer arranged adjacent to the second light-emitting portion, the organic layer includes a P-type charge generation layer, and the P-type charge generation layer includes any one or more of the star-shaped triamine derivatives described in the present invention.

[0129] Preferably, the light-emitting layer of the present invention comprises a host material and a doping material.

[0130] Preferably, the electron transport region of the present invention comprises at least one of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0131] Preferably, the organic layer of the present invention is located outside any one of the anode and the cathode, and the organic layer comprises a covering layer, and the covering layer comprises any one or more of the star-shaped triamine derivatives of the present invention.

[0132] The present invention does not particularly limit the materials of the thin films in the organic electroluminescent device, and materials known in the art can be used. The following is an introduction to the organic functional layers of the organic electroluminescent device and the electrodes on both sides of the device:

[0133] The organic electroluminescent device of the present invention is usually formed on a substrate. The substrate can be any substrate that does not change during the formation of electrodes and organic layers, and can be made of, for example, glass, plastic, polymer film, silicon, or the like.

[0134] The anode material of the present invention preferably uses a material with a high functional function to improve the hole injection efficiency. The anode material that can be used in the present invention is selected from the following: 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.

[0135] The hole injection layer of the present invention preferably uses a material with good hole-accepting ability. Specific examples of materials that can be used for the hole injection layer of the present invention include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, phenazine compounds, or the star-shaped triamine derivatives of the present invention, but are not limited thereto.

[0136] The hole transport layer material of the present invention preferably has a high hole mobility. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenylenediamine derivatives, fluorene derivatives, stilbene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., or the star-shaped triamine derivatives of the present invention, but is not limited thereto.

[0137] The electron blocking layer material of the present invention preferably uses a material that has the property of preventing electrons from passing through the light-emitting layer. Specific examples may include triarylamine derivatives, spirofluorene derivatives, furan derivatives and the like, such as TPD, NPB, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc., or the star-shaped triamine derivatives of the present invention, but are not limited thereto.

[0138] The light-emitting layer material of the present invention includes a host material and a dopant material. The host material of the light-emitting layer needs to have bipolar charge transport properties and a suitable energy level, and is selected from 4,4'-di(9-carbazole)biphenyl (CBP), 9,10-di(2-naphthyl)anthracene (ADN), 9,9'-(1,3-phenyl)di-9H-carbazole (mCP), 4,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), 9,10-di(1-naphthyl)anthracene (α-AND), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1":4",1"'-tetraphenyl]-4,4"'-diamino (4PNPB), 1,3,5-tri(9-carbazyl)benzene (TCP), etc. In addition to the above materials and combinations thereof, the host material of the light-emitting layer may also include other known materials suitable for the light-emitting layer, but is not limited thereto.

[0139] The light-emitting layer doping materials of the present invention are divided into blue light-emitting materials, green light-emitting materials and red light-emitting materials. The light-emitting layer doping materials can be a simple fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials, selected from 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)phenyl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)phenyl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)picolinyliridium (FIr pic), tris(2-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[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)), etc., but are not limited thereto.

[0140] The hole-blocking layer of the present invention preferably uses a material with strong hole-blocking ability and suitable HOMO / LUMO energy levels. The hole-blocking layer material of the present invention can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, phenanthroline derivatives, azobenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0141] The charge generation layer materials of the present invention include n-type charge generation materials and p-type charge generation materials.

[0142] The n-type charge generation material of the present invention can be selected from the following materials or one of their combinations: tris-(8-hydroxyquinolinolato)aluminum (Alq3), 2-biphenyl-4-yl-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), spiro-PBD, lithium quinolate (Liq), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-phenolato)aluminum (BAlq), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-bis(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (NBphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 3 -(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), 1,3,5-tris(p-pyridin-3-yl-phenyl)benzene (TpPyPB), 2,4,6-tris(3'-(pyridin-3-yl)biphenyl-3-yl)1,3,5-triazine (TmPPPyTz), poly[9,9-bis(3'-((N,N-dimethyl)-N-ethylammonium)-propyl)-2,7-fluorene]-alternating-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ) and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1), the fluorene compounds described in the present invention, etc., but are not limited thereto. In addition, an auxiliary n-type charge generation material may be included. For example, the auxiliary n-type charge generation material may be an alkali metal such as, but not limited to, Li, Cs, K, Rb, Na, or Fr, or an alkaline earth metal such as, but not limited to, Be, Mg, Ca, Sr, Ba, or Ra.

[0143] The p-type charge generation material of the present invention may include one of the following materials or a combination thereof: 4,4',4"-tris(3-methylphenylamino)triphenylamine (MTDATA), 4,4',4"-tris(N,N-diphenyl-amino)triphenylamine (NATA), 4,4',4"-tris(N-(naphthalene-1-yl)-N-phenyl-amino)triphenylamine (1T-NATA), 4,4',4"-tris(N-(naphthalene-2-yl)-N-phenyl-amino)triphenylamine (2T-NATA), copper phthalocyanine (CuPc), tris(4-carbazolyl-9-yl-phenyl)amine (TCTA), N,N'-diphenyl-N,N'-bis(1-naphthyl) -1,1'-biphenyl-4,4"-diamine (NPD), 1,4,5,8,9,11-hexaazatriphenylene hexacarbonitrile (dipyrazino[2,3-f:2'3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile) (HAT-CN), 1,3,5-tris[4-(diphenylamino)phenyl]benzene (TDAPB), poly(3,4-ethylenedioxythiophene)polystyrenesulfonate (PEDOT / PSS) and N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine, etc., or the star-shaped triamine derivatives described in the present invention, but are not limited thereto.

[0144] The hole blocking layer material described in the present invention is generally preferably a material that can effectively block hole transmission and allow excitons to recombine in the light-emitting layer rather than in the electron transport layer. It can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, imidazole derivatives, oxazole derivatives, oxadiazole derivatives, triazole derivatives, triazine derivatives, quinoline derivatives, diazine derivatives, azobenzene derivatives, anthrone derivatives, etc., but is not limited thereto.

[0145] The electron transport layer material of the present invention preferably has a material with 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-hydroxyquinolinolate)aluminum(III) (Alq3), 8-hydroxyquinolinolate-lithium (Liq), bis(2-methyl-8-hydroxyquinolinolate)(4-phenylphenolate)aluminum(III) (BAlq), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4,7-diphenyl-1,10-phenanthroline (Bphen), etc., but is not limited thereto.

[0146] The electron injection layer material described in the present invention is preferably a material with a smaller potential barrier difference than the adjacent organic layer material. Specific examples may include: alkali metal compounds (such as lithium oxide, lithium fluoride, cesium carbonate, cesium fluoride, 8-hydroxyquinoline cesium, 8-hydroxyquinoline aluminum), organic metal salts (metal acetates, metal benzoates or metal stearates), molybdenum trioxide, metallic aluminum, etc., but are not limited thereto.

[0147] The cathode material of the present invention preferably uses a material with a low work function that can promote electron injection into the organic layer to reduce the electron injection barrier. The cathode material 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 thereof, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.

[0148] The cover layer described in the present invention is provided on the outside of either the anode or cathode, and is preferably made of a material that improves the light coupling efficiency within the device. The cover layer 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, diamine derivatives, porphyrin derivatives, phthalocyanine derivatives, or the star-shaped triamine derivatives described in the present invention, but is not limited thereto.

[0149] The present invention has no special limitation on the thickness of each organic layer of the organic electroluminescent device, and the thickness commonly used in the art can be adopted.

[0150] The organic electroluminescent device of the present invention can be produced by any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slit coating, and dip coating.

[0151] The organic electroluminescent device of the present invention can be a top-emitting type, a bottom-emitting type or a bidirectional-emitting type.

[0152] The organic electroluminescent device of the present invention can be widely used in the fields of panel display, lighting source, flexible OLED, electronic paper, organic solar cell, organic photoreceptor or organic thin film transistor, signboard, signal light, etc.

[0153] The present invention provides a method for preparing the compound represented by Formula I, which is prepared by a carbon-nitrogen coupling reaction well known in the art, but the preparation method of the present invention is not limited thereto. The structure of Formula I can be prepared by the following reaction route:

[0154] 1. Preparation of intermediate A, intermediate B, and intermediate C:

[0155]

[0156] 2. When intermediate B and intermediate C are different, the synthetic route of formula I is as follows:

[0157]

[0158] 3. When intermediate B is the same as intermediate C, the synthetic route of formula I is as follows:

[0159]

[0160] Among them, X a The same as or different from each other, any one selected from Cl, Br, I; Ar1 ​​to Ar6, L1 to L6, R a ~R b The limitation is the same as above.

[0161] In the present invention, the above-mentioned substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of the substituents can be changed according to techniques known in the art.

[0162] By the following examples, the present invention is explained in more detail, but it is not intended to limit the present invention. On the basis of this description, those of ordinary skill in the art will be able to implement the present invention and prepare other compounds and devices according to the present invention within the disclosed entire range without paying creative work.

[0163] Preparation and characterization of compounds

[0164] Description of raw materials, reagents and characterization equipment:

[0165] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples, and they can be commercially available products or prepared using methods well known to those skilled in the art. The raw materials and reagents used in the present invention are all reagent-grade.

[0166] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0167] Elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5–10 mg;

[0168] Synthesis Example 1: Preparation of Intermediate A-13

[0169]

[0170] Under nitrogen, a-13 (126.00 mmol, 11.73 g), b-13 (120.00 mmol, 19.44 g), PdCl2(dppf) (1.20 mmol, 0.89 g), and sodium tert-butoxide (210.00 mmol, 20.18 g) were added sequentially to a reaction flask. Then, 600 mL of toluene was added and the mixture was heated under reflux for 4.5 hours. After the reaction was complete, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation. The organic layer was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and suction filtered. The resulting solid was recrystallized from ethyl acetate to obtain intermediate A-13 (17.77 g, 85% yield) with HPLC purity ≥99.73%. Mass spectrum: m / z: 174.1215 (theoretical value: 174.1205).

[0171] By replacing the raw materials accordingly, intermediates A / B / C can be prepared according to the preparation method of intermediate A-13 in Synthesis Example 1. The raw materials are shown in the following table:

[0172]

[0173]

[0174]

[0175]

[0176] Synthesis Example 2: Preparation of Compound 13

[0177]

[0178] Preparation of intermediate I-13:

[0179] Under nitrogen, g-13 (80.00 mmol, 25.39 g), A-13 (80.00 mmol, 13.94 g), Pd(OAc)2 (0.80 mmol, 0.18 g), tri-tert-butylphosphine (3.2 mL of a 0.50 M toluene solution, 1.60 mmol), sodium tert-butoxide (200 mmol, 19.22 g), and 400 mL of toluene were added to the reaction flask in sequence. The mixture was stirred and heated under reflux for 5.5 hours. After the reaction was complete, the mixture was cooled to room temperature, and dichloromethane and distilled water were added to the mixture for extraction. The mixture was allowed to stand for separation, and the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The filtrate was purified by silica gel column chromatography (dichloromethane:n-hexane = 1:8) to obtain intermediate I-13 (23.57 g, yield 81%) with HPLC purity ≥99.85%. Mass spectrum m / z: 362.0246 (theoretical value: 362.0234).

[0180] Preparation of intermediate II-13:

[0181] Under nitrogen, I-13 (50.00 mmol, 18.18 g), B-13 (50.00 mmol, 12.27 g), Pd(OAc)2 (0.50 mmol, 0.11 g), tri-tert-butylphosphine (2.0 mL of a 0.50 M toluene solution, 1.00 mmol), sodium tert-butoxide (113.00 mmol, 10.86 g), and 320 mL of toluene were added to the reaction flask, stirred, and heated under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature, extracted with dichloromethane and distilled water, and allowed to stand for separation. The organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The filtrate was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1:1) to obtain intermediate II-13 (20.60 g, 78% yield) with an HPLC purity of ≥99.88%. Mass spectrum m / z: 527.2161 (theoretical value: 527.2177).

[0182] Preparation of compound 13:

[0183] Under nitrogen, a reaction flask was charged with II-13 (30.00 mmol, 15.84 g), C-13 (30.00 mmol, 9.88 g), Pd2(dba)3 (0.30 mmol, 0.27 g), X-Phos (0.60 mmol, 0.29 g), sodium tert-butoxide (75.00 mmol, 7.21 g), and 300 ml of toluene. The mixture was stirred and heated under reflux for 7 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. The mixture was allowed to stand for separation. The organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The temperature was lowered for crystallization, and the resulting solid was filtered with suction. The resulting solid was recrystallized from toluene to obtain compound 13 (17.98 g, 73% yield) with HPLC purity ≥99.93%. Mass spectrum: m / z: 820.3298 (theoretical value: 820.3284). Theoretical element content (%) C 57 H 36 D5N3OS: C, 83.38; H, 5.65; N, 5.12. Measured element content (%): C, 83.40; H, 5.67; N, 5.09.

[0184] Synthesis Example 3: Preparation of Compound 28

[0185]

[0186] Compound 28 (19.03 g) was obtained by the same preparation method as in Synthesis Example 2, except that B-13 was replaced by an equal amount of B-28 and C-13 was replaced by an equal amount of C-28. HPLC purity was ≥99.96%. Mass spectrum m / z: 880.3273 (theoretical value: 880.3284). Theoretical element content (%): C 62 H 36 D5N3OS: C, 84.52; H, 5.26; N, 4.77. Measured element content (%): C, 84.55; H, 5.23; N, 4.80.

[0187] Synthesis Example 4: Preparation of Compound 75

[0188]

[0189] Preparation of intermediate II-75:

[0190] Under nitrogen, g-75 (35.00 mmol, 9.95 g), A-75 (70.00 mmol, 17.52 g), Pd(OAc)2 (0.40 mmol, 0.09 g), x-phos (0.80 mmol, 0.38 g), sodium tert-butoxide (110.00 mmol, 10.57 g), and 350 mL of toluene were added to a reaction flask in sequence. The mixture was stirred and heated under reflux for 6 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with dichloromethane and distilled water. The mixture was allowed to stand for separation. The organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The filtrate was purified by silica gel column chromatography (ethyl acetate:n-hexane = 1:5) to obtain II-75 (15.92 g, 73% yield) with HPLC purity ≥99.89%. Mass spectrum: m / z: 622.2977 (theoretical value: 622.2960). Preparation of compound 75:

[0191] Under nitrogen protection, II-75 (20.00 mmol, 12.47 g), C-75 (20.00 mmol, 6.31 g), Pd2(dba)3 (0.25 mmol, 0.23 g), tri-tert-butylphosphine (1.00 mL of a 0.50 M toluene solution, 0.50 mmol), sodium tert-butoxide (50.00 mmol, 4.80 g) and 200 ml of toluene were added to the reaction flask in sequence, and the mixture was stirred and heated under reflux for 7.0 hours. After the reaction was completed, it was cooled to room temperature, and dichloromethane and distilled water were added to the mixture for extraction. The mixture was allowed to stand and the organic phase was collected and dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by distillation under reduced pressure. The temperature was lowered for crystallization, and suction filtered. The resulting solid was recrystallized from toluene to give compound 75 (12.81 g, 71% yield) with an HPLC purity of ≥99.95%. Mass spectrum m / z: 901.3930 (theoretical value: 901.3911). Theoretical element content (%) C 63 H 35 D 10 N3OS: C, 83.87; H, 6.14; N, 4.66. Measured element content (%): C, 83.90; H, 6.16; N, 4.63.

[0192] Synthesis Example 5: Preparation of Compound 99

[0193]

[0194] Compound 99 (10.20 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-99 and A-75 was replaced with an equal molar amount of A-13. HPLC purity was ≥99.97%. Mass spectrum m / z: 738.3305 (theoretical value: 738.3317). Theoretical element content (%): C 50 H 22 D 13 N3OS: C, 81.27; H, 6.54; N, 5.69. Measured element content (%): C, 81.30; H, 6.51; N, 5.71.

[0195] Synthesis Example 6: Preparation of Compound 121

[0196]

[0197] Compound 121 (10.01 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-121, A-75 was replaced with an equal molar amount of A-13, and C-75 was replaced with an equal molar amount of C-121. HPLC purity was ≥99.93%. Mass spectrum m / z: 735.3144 (theoretical value: 735.3129). Theoretical element content (%): C50 H 25 D 10 N3OS: C, 81.60; H, 6.16; N, 5.71. Measured element content (%): C, 81.58; H, 6.19; N, 5.67.

[0198] Synthesis Example 7: Preparation of Compound 136

[0199]

[0200] Following the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136 and C-75 with an equal molar amount of C-136, compound 136 (12.64 g) was obtained. HPLC purity ≥ 99.95%. Mass spectrum m / z: 853.3352 (theoretical value: 853.3370). Theoretical element content (%): C 58 H 31 D 10 N3S2: C, 81.56; H, 6.02; N, 4.92. Measured element content (%): C, 81.60; H, 6.04; N, 4.89.

[0201] Synthesis Example 8: Preparation of Compound 165

[0202]

[0203] Compound 165 (11.19 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-13. HPLC purity was ≥99.94%. Mass spectrum m / z: 735.3143 (theoretical value: 735.3129). Theoretical element content (%): C 50 H 25 D 10 N3OS: C, 81.60; H, 6.16; N, 5.71. Measured element content (%): C, 81.58; H, 6.18; N, 5.67.

[0204] Synthesis Example 9: Preparation of Compound 183

[0205]

[0206] Compound 183 (10.89 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136, A-75 was replaced with an equal molar amount of A-13, and C-75 was replaced with an equal molar amount of C-183. HPLC purity was ≥99.93%. Mass spectrum m / z: 735.3118 (theoretical value: 735.3129). Theoretical element content (%): C50 H 25 D 10 N3OS: C, 81.60; H, 6.16; N, 5.71. Measured element content (%): C, 81.58; H, 6.18; N, 5.69.

[0207] Synthesis Example 10: Preparation of Compound 206

[0208]

[0209] Compound 206 (11.48 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136, A-75 was replaced with an equal molar amount of A-13, and C-75 was replaced with an equal molar amount of C-206. HPLC purity was ≥99.95%. Mass spectrum m / z: 785.3269 (theoretical value: 785.3285). Theoretical element content (%): C 54 H 27 D 10 N3OS: C, 82.52; H, 6.02; N, 5.35. Measured element content (%): C, 82.49; H, 6.04; N, 5.32.

[0210] Synthesis Example 11: Preparation of Compound 223

[0211]

[0212] Compound 223 (11.32 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136, A-75 was replaced with an equal molar amount of A-13, and C-75 was replaced with an equal molar amount of C-223. HPLC purity was ≥99.92%. Mass spectrum m / z: 785.3298 (theoretical value: 785.3285). Theoretical element content (%): C 54 H 27 D 10 N3OS: C, 82.52; H, 6.02; N, 5.35. Measured element content (%): C, 82.53; H, 6.01; N, 5.33.

[0213] Synthesis Example 12: Preparation of Compound 257

[0214]

[0215] Compound 257 (12.18 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-13, and C-75 with an equal molar amount of C-257. HPLC purity ≥ 99.97%. Mass spectrum m / z: 811.3427 (theoretical value: 811.3442). Theoretical element content (%): C 56 H 29 D 10 N3OS: C, 82.83; H, 6.08; N, 5.17. Measured element content (%): C, 82.84; H, 6.05; N, 5.20.

[0216] Synthesis Example 13: Preparation of Compound 261

[0217]

[0218] Compound 261 (11.61 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-261, and C-75 with an equal molar amount of C-261. HPLC purity ≥ 99.93%. Mass spectrum m / z: 805.3083 (theoretical value: 805.3065). Theoretical element content (%): C 56 H 35 D4N3OS: C, 83.45; H, 5.38; N, 5.21. Measured element content (%): C, 83.43; H, 5.40; N, 5.18.

[0219] Synthesis Example 14: Preparation of Compound 264

[0220]

[0221] Compound 264 (12.61 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-13, and C-75 with an equal molar amount of C-264. HPLC purity was ≥99.90%. Mass spectrum m / z: 887.3745 (theoretical value: 887.3755). Theoretical element content (%): C 62 H 33 D 10 N3OS: C, 83.84; H, 6.01; N, 4.73. Measured element content (%): C, 83.82; H, 6.03; N, 4.69.

[0222] Synthesis Example 15: Preparation of Compound 278

[0223]

[0224] Compound 278 (11.69 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-13, and C-75 with an equal molar amount of C-278. HPLC purity ≥ 99.95%. Mass spectrum m / z: 811.3456 (theoretical value: 811.3442). Theoretical element content (%): C 56 H 29 D 10 N3OS: C, 82.83; H, 6.08; N, 5.17. Measured element content (%): C, 82.81; H, 6.10; N, 5.20.

[0225] Synthesis Example 16: Preparation of Compound 310

[0226]

[0227] Following the same preparation method as in Synthesis Example 4, g-75 was replaced with an equal molar amount of g-136 to obtain compound 310 (13.32 g). HPLC purity ≥ 99.98%. Mass spectrum m / z: 887.3739 (theoretical value: 887.3755). Theoretical element content (%): C 62 H 33 D 10 N3OS: C, 83.84; H, 6.01; N, 4.73. Measured element content (%): C, 83.82; H, 6.04; N, 4.69.

[0228] Synthesis Example 17: Preparation of Compound 331

[0229]

[0230] Compound 331 (13.36 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-331, and C-75 with an equal molar amount of C-331. HPLC purity was ≥99.94%. Mass spectrum m / z: 953.3697 (theoretical value: 953.3683). Theoretical element content (%): C 66 H 35 D 10 N3S2: C, 83.07; H, 5.81; N, 4.40. Measured element content (%): C, 83.10; H, 5.84; N, 4.38.

[0231] Synthesis Example 18: Preparation of Compound 363

[0232]

[0233] Compound 363 (13.69 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and C-75 was replaced with an equal molar amount of C-363. HPLC purity was ≥99.91%. Mass spectrum m / z: 963.4057 (theoretical value: 963.4068). Theoretical element content (%): C 68 H 37 D 10 N3OS: C, 84.70; H, 5.96; N, 4.36. Measured element content (%): C, 84.68; H, 5.93; N, 4.40.

[0234] Synthesis Example 19: Preparation of Compound 385

[0235]

[0236] Compound 385 (13.32 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-385. HPLC purity was ≥99.97%. Mass spectrum m / z: 887.3771 (theoretical value: 887.3755). Theoretical element content (%): C 62 H 33 D 10 N3OS: C, 83.84; H, 6.01; N, 4.73. Measured element content (%): C, 83.82; H, 6.05; N, 4.69.

[0237] Synthesis Example 20: Preparation of Compound 413

[0238]

[0239] Compound 413 (13.17 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-413, and C-75 with an equal molar amount of C-413. HPLC purity was ≥99.93%. Mass spectrum m / z: 901.3420 (theoretical value: 901.3401). Theoretical element content (%): C 62 H 35 D8N3S2: C, 82.54; H, 5.70; N, 4.66. Measured element content (%): C, 82.52; H, 5.67; N, 4.70.

[0240] Synthesis Example 21: Preparation of Compound 445

[0241]

[0242] Compound 445 (11.84 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-445, and C-75 with an equal molar amount of C-445. HPLC purity ≥ 99.95%. Mass spectrum m / z: 821.4086 (theoretical value: 821.4069). Theoretical element content (%): C 56 H 19 D 20 N3OS: C, 81.81; H, 7.23; N, 5.11. Measured element content (%): C, 81.78; H, 7.25; N, 5.09.

[0243] Synthesis Example 22: Preparation of Compound 462

[0244]

[0245] Compound 462 (13.20 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-462, and C-75 with an equal molar amount of C-136. HPLC purity ≥ 99.92%. Mass spectrum m / z: 969.4919 (theoretical value: 969.4935). Theoretical element content (%): C 66 H 51 D 10 N3S2: C, 81.69; H, 7.37; N, 4.33. Measured element content (%): C, 81.71; H, 7.40; N, 4.31.

[0246] Synthesis Example 23: Preparation of Compound 479

[0247]

[0248] Compound 479 (11.46 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-479. HPLC purity was ≥99.94%. Mass spectrum m / z: 763.3459 (theoretical value: 763.3442). Theoretical element content (%): C 52 H 29 D 10 N3OS: C, 81.75; H, 6.46; N, 5.50. Measured element content (%): C, 81.78; H, 6.50; N, 5.49.

[0249] Synthesis Example 24: Preparation of Compound 496

[0250]

[0251] Compound 496 (13.38 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-496, and C-75 with an equal molar amount of C-183. HPLC purity ≥ 99.96%. Mass spectrum m / z: 915.4054 (theoretical value: 915.4068). Theoretical element content (%): C 64 H 37 D 10 N3OS: C, 83.90; H, 6.27; N, 4.59. Measured element content (%): C, 83.88; H, 6.30; N, 4.61.

[0252] Synthesis Example 25: Preparation of Compound 511

[0253]

[0254] Compound 511 (12.58 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-511. HPLC purity was ≥99.91%. Mass spectrum m / z: 897.4372 (theoretical value: 897.4382). Theoretical element content (%): C 62 H 23 D 20 N3OS: C, 82.91; H, 7.07; N, 4.68. Measured element content (%): C, 82.89; H, 7.05; N, 4.70.

[0255] Synthesis Example 26: Preparation of Compound 541

[0256]

[0257] Compound 496 (12.68 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-541. HPLC purity was ≥99.92%. Mass spectrum m / z: 879.3938 (theoretical value: 879.3919). Theoretical element content (%): C 56 H 41 D 10 N3OSSi2: C, 76.40; H, 6.98; N, 4.77. Measured element content (%): C, 76.38; H, 6.95; N, 4.80.

[0258] Synthesis Example 27: Preparation of Compound 583

[0259]

[0260] Compound 583 (13.29 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-583. HPLC purity was ≥99.93%. Mass spectrum m / z: 935.3773 (theoretical value: 935.3755). Theoretical element content (%): C 66 H 33 D 10 N3OS: C, 84.67; H, 5.70; N, 4.49. Measured element content (%): C, 84.70; H, 5.68; N, 4.51.

[0261] Synthesis Example 28: Preparation of Compound 588

[0262]

[0263] Compound 588 (14.58 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-588. HPLC purity was ≥99.92%. Mass spectrum m / z: 1087.4368 (theoretical value: 1087.4381). Theoretical element content (%): C 78 H 41 D 10 N3OS: C, 86.08; H, 5.65; N, 3.86. Measured element content (%): C, 86.10; H, 5.64; N, 3.90.

[0264] Synthesis Example 29: Preparation of Compound 594

[0265]

[0266] Compound 594 (11.75 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-594. HPLC purity was ≥99.96%. Mass spectrum m / z: 815.3770 (theoretical value: 815.3755). Theoretical element content (%): C 56 H 33 D 10 N3OS: C, 82.42; H, 6.54; N, 5.15. Measured element content (%): C, 82.39; H, 6.56; N, 5.13.

[0267] Synthesis Example 30: Preparation of Compound 604

[0268]

[0269] Compound 604 (13.56 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-604. HPLC purity was ≥99.95%. Mass spectrum m / z: 967.4369 (theoretical value: 967.4381). Theoretical element content (%): C 68 H 41 D 10 N3OS: C, 84.35; H, 6.35; N, 4.34. Measured element content (%): C, 84.31; H, 6.37; N, 4.33.

[0270] Synthesis Example 31: Preparation of Compound 613

[0271]

[0272] Compound 613 (14.14 g) was obtained by the same preparation method as in Synthesis Example 4, except that g-75 was replaced with an equal molar amount of g-136 and A-75 was replaced with an equal molar amount of A-613. HPLC purity was ≥99.91%. Mass spectrum m / z: 967.4366 (theoretical value: 967.4381). Theoretical element content (%): C 68 H 41 D 10 N3OS: C, 84.35; H, 6.35; N, 4.34. Measured element content (%): C, 84.32; H, 6.37; N, 4.35.

[0273] Synthesis Example 32: Preparation of Compound 667

[0274]

[0275] Compound 677 (12.95 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-677, and C-75 with an equal molar amount of C-677. HPLC purity ≥ 99.93%. Mass spectrum m / z: 911.3767 (theoretical value: 911.3755). Theoretical element content (%): C 64 H 33 D 10 N3OS: C, 84.27; H, 5.85; N, 4.61. Measured element content (%): C, 84.30; H, 5.82; N, 4.58.

[0276] Synthesis Example 33: Preparation of Compound 709

[0277]

[0278] Compound 709 (11.72 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-13, and C-75 with an equal molar amount of C-709. HPLC purity was ≥99.92%. Mass spectrum m / z: 791.3771 (theoretical value: 791.3755). Theoretical element content (%): C 54 H 33 D 10 N3OS: C, 81.89; H, 6.74; N, 5.31. Measured element content (%): C, 81.91; H, 6.71; N, 5.27.

[0279] Synthesis Example 34: Preparation of Compound 747

[0280]

[0281] Compound 747 (15.27 g) was obtained by the same preparation method as in Synthesis Example 4, replacing g-75 with an equal molar amount of g-136, A-75 with an equal molar amount of A-747, and C-75 with an equal molar amount of C-747. HPLC purity ≥ 99.95%. Mass spectrum m / z: 1089.4525 (theoretical value: 1089.4537). Theoretical element content (%): C 78 H 43 D 10 N3OS: C, 85.92; H, 5.82; N, 3.85. Measured element content (%): C, 85.89; H, 5.78; N, 3.87.

[0282] [Device Example 1]

[0283] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water, each time for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in isopropyl alcohol, acetone, methanol and other solvents in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0284] The organic electroluminescent device was prepared by vacuum evaporation on a cleaned ITO / Ag / ITO substrate, and the following ingredients were deposited in sequence: hole injection layer HI-1 (60 nm); hole transport layer compound 13 (100 nm); light-emitting layer RH-1:RH-2:RD=49:49:2 (mass ratio, 40 nm); electron transport layer ET-1:Liq=1:1 (mass ratio, 35 nm); electron injection layer LiF (0.8 nm); cathode Mg:Ag=1:9 (mass ratio, 12 nm); and covering layer CP-1 (80 nm).

[0285]

[0286] [Device Example 2-33]

[0287] Compound 28, compound 75, compound 99, compound 121, compound 136, compound 165, compound 183, compound 206, compound 223, compound 257, compound 261, compound 264, compound 278, compound 310, compound 331, compound 363, compound 385, compound 413, compound 445, compound 462, compound 479, compound 496, compound 511, compound 541, compound 583, compound 588, compound 594, compound 604, compound 613, compound 667, compound 709 or compound 747 of the present invention were used to replace compound 13 in device example 1 as a hole transport layer material. Except for this, an organic electroluminescent device was prepared by the same preparation method as device example 1.

[0288] [Comparative Device Examples 1-4]

[0289] An organic electroluminescent device was prepared by the same preparation method as in Device Example 1 except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 or Comparative Compound 4 was used to replace Compound 13 in Device Example 1 as the hole transport layer material.

[0290] A combined IVL test system, comprised of test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to measure the luminous efficiency of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System. The test environment was atmospheric and room temperature. The test results are shown in Tables 1 to 3.

[0291] The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Examples 1-33 of the present invention and Comparative Examples 1-4 are shown in Table 1 below.

[0292]

[0293]

[0294] According to the data in Table 1, it can be seen that applying the star-shaped triamine derivative represented by formula I of the present invention as a hole transport layer material in an organic electroluminescent device can effectively improve the luminous efficiency and service life of the device.

[0295] [Device Example 34]

[0296] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water, each time for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in isopropyl alcohol, acetone, methanol and other solvents in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0297] By vacuum evaporation, a hole injection layer HI-1 (60 nm); a first hole transport layer HT-1 (80 nm); a second hole transport layer I3 (30 nm); a light-emitting layer GH-1:GH-2:GD = 46:46:8 (mass ratio, 40 nm); an electron transport layer ET-2:Liq = 1:1 (mass ratio, 30 nm); an electron injection layer LiF (1.0 nm); a cathode Mg:Ag = 1:9 (mass ratio, 15 nm); and a covering layer CP-1 (85 nm) were sequentially deposited on a cleaned ITO / Ag / ITO substrate to prepare an organic electroluminescent device.

[0298]

[0299] [Device Examples 35-66]

[0300] Compound 28, compound 75, compound 99, compound 121, compound 136, compound 165, compound 183, compound 206, compound 223, compound 257, compound 261, compound 264, compound 278, compound 310, compound 331, compound 363, compound 385, compound 413, compound 445, compound 462, compound 479, compound 496, compound 511, compound 541, compound 583, compound 588, compound 594, compound 604, compound 613, compound 667, compound 709 or compound 747 of the present invention are used to replace compound 13 in device example 34 as the second hole transport layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 34.

[0301] [Comparative Device Examples 5-8]

[0302] An organic electroluminescent device was prepared by the same preparation method as that of Device Example 34, except that Comparative Compound 1, Comparative Compound 2, Comparative Compound 3 or Comparative Compound 4 was used to replace Compound 13 in Device Example 34 as the hole blocking layer material.

[0303] The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Examples 34-66 of the present invention and Comparative Examples 5-8 are shown in Table 2 below.

[0304]

[0305]

[0306] According to the data in Table 2, it can be seen that the star-shaped triamine derivative represented by Formula I of the present invention has good hole transport ability, which can balance the transport of carriers and increase the recombination probability of excitons in the light-emitting layer. When used as a second hole transport layer material in an organic electroluminescent device, it can effectively improve the luminous efficiency and service life of the device.

[0307] [Device Example 67]

[0308] First, the ITO / Ag / ITO substrate was ultrasonically cleaned three times in distilled water, each time for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in isopropyl alcohol, acetone, methanol and other solvents in turn, each time for 10 minutes. After the washing, it was dried at 120°C.

[0309] The organic electroluminescent device was prepared by vacuum evaporation on a cleaned ITO / Ag / ITO substrate, and the following ingredients were deposited in sequence: hole injection layer HI-1 (60 nm); hole transport layer HT-1 (90 nm); light-emitting layer RH-3:RH-4:RD-2=48:48:4 (mass ratio, 40 nm); electron transport layer ET-2:Liq=1:1 (mass ratio, 30 nm); electron injection layer LiF (1.1 nm); cathode Mg:Ag=1:9 (mass ratio, 15 nm); and covering layer compound 13 (80 nm).

[0310]

[0311] [Device Examples 68-99]

[0312] Compound 28, compound 75, compound 99, compound 121, compound 136, compound 165, compound 183, compound 206, compound 223, compound 257, compound 261, compound 264, compound 278, compound 310, compound 331, compound 363, compound 385, compound 413, compound 445, compound 462, compound 479, compound 496, compound 511, compound 541, compound 583, compound 588, compound 594, compound 604, compound 613, compound 667, compound 709 or compound 747 of the present invention are used to replace compound 13 in device example 67 as the covering layer material. Except for this, an organic electroluminescent device is prepared by the same preparation method as device example 67.

[0313] [Comparative Device Examples 9-10]

[0314] An organic electroluminescent device was prepared by the same preparation method as in Device Example 67, except that Comparative Compound 2 or Comparative Compound 3 was used instead of Compound 13 in Device Example 67 as the covering layer material.

[0315] The test results of the luminescence characteristics of the organic electroluminescent devices obtained in Examples 67-99 of the present invention and Comparative Examples 9-10 are shown in Table 3 below.

[0316]

[0317]

[0318] According to the data results in Table 3, it can be seen that the star-shaped triamine derivatives of the present invention are used as cover layer materials for organic electroluminescent devices, effectively increasing the light extraction efficiency of the device, and improving the luminous efficiency and service life of the device.

[0319] It should be noted that the present invention is particularly described using individual embodiments. However, without departing from the principles of the present invention, a person skilled in the art may make various improvements in form or detail to the present invention, and these improvements also fall within the scope of protection of the present invention.

Claims

1. A star-shaped triamine derivative, characterized in that The star-shaped triamine derivative has a structure as shown in Formula I, In formula I, the Ar1 is selected from the group shown in formula II; Ar2 is selected from the group shown in formula III; The Ar3 to Ar6 are the same as or different from each other and are selected from any one of the following groups which are substituted or unsubstituted by one or more R3: a C6 to C30 aryl group, a fused ring group of a C6 to C30 aromatic ring and a C3 to C30 aliphatic ring, and a C2 to C30 heteroaryl group; R3 is selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl; Said X is selected from O or S; The ring A and ring B are the same or different and are selected from a C6-C30 aromatic ring, which is absent, substituted or unsubstituted; when X is selected from O, the ring A and ring B are not both selected from none; R1 and R2 are the same as or different from each other and are selected from any one of hydrogen, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl; R a ~R c are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, and substituted or unsubstituted C2-C30 heteroaryl; The a is selected from 0, 1, 2, 3, 4, 5 or 6. When there are two or more R1s, the two or more R1s are the same or different from each other, or two adjacent R1s can be connected to form a substituted or unsubstituted ring; when there are two or more R2s, the two or more R2s are the same or different from each other, or two adjacent R2s can be connected to form a substituted or unsubstituted ring; The L1 to L6 are the same as or different from each other and are selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C6-C30 aromatic ring and a C3-C30 aliphatic ring fused cyclic group, a substituted or unsubstituted C2-C30 heteroarylene group, and combinations thereof; Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R a 、R b 、R c At least one of the compounds contains deuterium.

2. A star-shaped triamine derivative according to claim 1, characterized in that: The formula II is selected from any one of the groups shown below; The R1s are the same as or different from each other and are selected from hydrogen, cyano, trifluoromethyl, halogen, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl; The b1 is selected from 0, 1, 2, 3, 4 or 5, the b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the b4 is selected from 0, 1, 2 or 3, the b5 is selected from 0, 1, 2, 3 or 4, the b6 is selected from 0, 1, 2, 3, 4, 5 or 6, and the b7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

3. A star-shaped triamine derivative according to claim 1, characterized in that: The formula III is selected from any one of the groups shown below; The R2 are the same as or different from each other and are selected from hydrogen, cyano, trifluoromethyl, halogen, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopentanyl, benzocyclohexanyl, benzofuranyl, or benzothiophenyl; The c1 is selected from 0, 1, 2, 3, 4 or 5, the c2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the c3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, the c4 is selected from 0, 1, 2 or 3, the c5 is selected from 0, 1, 2, 3 or 4, the c6 is selected from 0, 1, 2, 3, 4, 5 or 6, and the c7 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

4. A star-shaped triamine derivative according to claim 1, characterized in that: The Ar3 to Ar6 are the same or different from each other and are selected from any one of the following groups; Said r and t1 are the same or different from each other and are selected from CH or N atoms. When r is bonded to other groups, said r is selected from C atoms; Said t2 is selected from O, S, N (R z ) Said t3 is selected from O, S, C (R x R y )、N(R z ) The ring C is selected from a substituted or unsubstituted C3 to C7 aliphatic ring; The R3, R4, R x 、R y are the same as or different from each other and are selected from any one of hydrogen, deuterium, cyano, nitro, trifluoromethyl, halogen, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the R x 、R y They may be connected to each other to form a substituted or unsubstituted ring; or the R x 、R y Can directly bond with any one of L3 to L6; The R z Any one selected from hydrogen, deuterium, substituted or unsubstituted C1-C25 alkyl, substituted or unsubstituted C2-C25 alkenyl, substituted or unsubstituted C3-C25 cycloalkyl, substituted or unsubstituted C3-C25 silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 fused ring of aromatic ring and C3-C30 aliphatic ring, substituted or unsubstituted C2-C30 heteroaryl; or said R z Can directly bond with any one of L3 to L6; The d1 is selected from 0, 1, 2, 3, 4 or 5, the d2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7, the d3 is selected from 0, 1, 2 or 3, the d4 is selected from 0, 1, 2, 3 or 4, and the d5 is selected from 0 or 1. When two or more R3 are present, the two or more R3 are the same as or different from each other, or two adjacent R3 can be connected to each other to form a substituted or unsubstituted ring; when two or more R4 are present, the two or more R4 are the same as or different from each other.

5. A star-shaped triamine derivative according to claim 1, characterized in that: The Ar3 to Ar6 are the same or different from each other and are selected from any one of the following groups; R3 and R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, benzofuranyl, or benzothiophenyl; The f1 is selected from 0, 1, 2, 3, 4, or 5, the f2 is selected from 0, 1, 2, 3, or 4, the f3 is selected from 0, 1, 2, 3, 4, 5, 6, or 7, the f4 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, the f5 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11, the f6 is selected from 0, 1, 2, or 3, the f7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, the f8 is selected from 0, 1, 2, 3, 4, 5, or 6, the f9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8, the f 10 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said f 11 is selected from 0, 1 or 2, said f 12 Select from 0 or 1.

6. A star-shaped triamine derivative according to claim 1, characterized in that: The L1 to L6 are the same or different from each other and are selected from a single bond or any one of the groups shown below; The R4 are the same as or different from each other and are selected from hydrogen, deuterium, cyano, trifluoromethyl, or any one of the following groups which are substituted or unsubstituted by one or more deuterium, cyano, trifluoromethyl, trimethylsilyl, triphenylsilyl, C1-C12 alkyl, or C3-C12 cycloalkyl: methyl, ethyl, propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, or benzocyclohexyl; The e1 is selected from 0, 1, 2, 3 or 4, the e2 is selected from 0, 1, 2 or 3, the e3 is selected from 0, 1 or 2, the e4 is selected from 0, 1, 2, 3, 4, 5 or 6, the e5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, the e6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, and the e7 is selected from 0 or 1.

7. A star-shaped triamine derivative according to claim 1, characterized in that: The star-shaped triamine derivative is selected from any one of the structures shown below; 8. 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 either the anode or the cathode, characterized in that: The organic layer comprises any one or more of the star-shaped triamine derivatives according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, wherein the organic layer is located between the anode and the cathode, the organic layer comprises a hole transport region, a light emitting layer, and an electron transport region, and the hole transport region is located between the anode and the light emitting layer, characterized in that: The hole transport region comprises any one or more of the star-shaped triamine derivatives according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, wherein the organic layer is located outside of any one of the anode and the cathode, and the organic layer includes a covering layer, wherein: The covering layer comprises any one or more of the star-shaped triamine derivatives according to any one of claims 1 to 7.

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