Star-type triamine compound and organic electroluminescent device thereof

Abstract

The invention provides a star-type triamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials. The star-shaped triamine compound provided by the invention is relatively high in hole transport rate, and when the star-shaped triamine compound is applied to a hole transport region of an organic electroluminescent device, the luminous efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged; meanwhile, when the compound is applied to a covering layer of the organic light-emitting device, the luminous efficiency of the organic light-emitting device is further improved, the service life of the organic light-emitting device is further prolonged, the compound is simple in preparation method, raw materials are easy to obtain, and the compound can be widely applied to the fields of organic thin film transistors, panel display and the like and has a good application effect and a good industrialization prospect.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs), also known as organic light-emitting diodes (OLEDs), are a new type of display technology that has been widely used in consumer electronics such as smartphones and TV screens, becoming a mainstream display panel technology. As a surface light source technology, OLED emits light similar to natural diffuse light, resulting in a soft, non-glaring appearance. It also offers unique advantages such as being lightweight, thin, and flexible. It holds significant potential in the lighting field and is gradually replacing traditional liquid crystal display technology.

[0003] The structure of an organic electroluminescent device is a sandwich-like structure, consisting of an anode, a cathode, and organic layers positioned between or outside the anode and cathode. These organic layers typically include a hole transport layer (HTL), an electron transport layer (ETL), an emissive layer (EML), a hole injection layer (HIL), an electron injection layer (EIL), a hole blocking layer (HBL), an electron blocking layer (EBL), and a capping layer (CPL). These organic layers play an important role in improving the device's luminous efficiency and stability. When a voltage is applied across the device, holes and electrons are injected from the anode and cathode, respectively, into the organic functional layers. These carriers recombine in the emissive layer to form excitons, which transfer energy to the luminescent molecules, causing them to transition from the ground state to an excited state. The energy in the excited state is deactivated through radiation, releasing photons and generating visible light. In order to further improve the luminous efficiency of the device, two or more independent light-emitting units are connected in series through a charge generation layer (CGL) to form a stacked OLED. The electrons and holes generated by the charge generation layer are respectively injected into adjacent light-emitting units, and recombined into excitons in the light-emitting units to emit light. In addition, n-type doped layers / p-type doped layers are often used as connecting layers between light-emitting units.

[0004] Organic electroluminescent devices are already moving toward practical application and commercialization, but their brightness, efficiency, and lifespan still need to be further improved. Hole transport materials are a key class of organic semiconductor materials, but currently, their hole mobility is relatively low, leading to charge imbalance within the light-emitting layer. The low refractive index and glass transition temperature of the cover layer material reduce the device's lifespan. The charge generation layer also has poor carrier transport capabilities. These factors all hinder the development of OLED devices. Therefore, designing higher-performing hole transport layer materials, cover layer materials, and charge generation layer materials is crucial and a current research priority. Summary of the Invention

[0005] The present invention aims to provide a star-shaped triamine compound and an organic electroluminescent device thereof. When the star-shaped triamine compound provided by the present invention is applied to the hole transport region or cover layer of the organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device can be improved, thereby solving the problems of low luminous efficiency and short service life of the organic electroluminescent device in the prior art.

[0006] Specifically, the present invention provides a star-shaped triamine compound having the general formula shown in Structural Formula 1,

[0007]

[0008] The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, at least four of which are selected from the groups shown in Formula 2, and the remaining identical or different groups are selected from the following groups:

[0009]

[0010] The v is selected from C (R1) or N atoms the same or different, and the v at the bonding site is selected from C;

[0011] Said Y1 is selected from an O atom, a S atom or N(R3);

[0012] Said Y2 is selected from N(R3);

[0013] The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0014] The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;

[0015] The R3 is the same or different and is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0016] In Formula 2, X is selected from an O atom or a S atom, provided that when Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are simultaneously selected from Formula 2, X is not simultaneously selected from a S atom;

[0017] The z are identical or different and are selected from C(R a ) or a N atom, and z at the bonding site is selected from C;

[0018] The R a any one of hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R a are connected to each other to form a substituted or unsubstituted ring;

[0019] The L1, L2, L3, L4, L5, and L6 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused sub-ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[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 one or more electrodes of the anode and the cathode, and the organic layer contains the star-shaped triamine compound of the present invention.

[0021] Beneficial effects: The star-shaped triamine compound provided by the present invention has a high hole transport rate. When applied to the hole transport region of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved; at the same time, when it is applied to the covering layer of an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are further improved, and it has good application prospects. DETAILED DESCRIPTION

[0022] The present invention is further illustrated below with reference to specific examples. It should be understood that these examples are only used to illustrate the present invention and are not used to limit the scope of the present invention. After reading the present invention, modifications of various equivalent forms of the present invention made by those skilled in the art all fall within the scope of protection claimed in this application.

[0023] In the compounds of the present invention, any atom not designated as a specific isotope includes any stable isotope of that atom, and includes atoms at both their natural isotopic abundance and unnatural abundance. Taking hydrogen as an example, all naturally occurring compounds contain approximately 0.0156 atomic % deuterium per hydrogen atom.

[0024] Examples of the halogen according to the present invention may include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0025] The "C1-C15" in the "substituted or unsubstituted C1-C15 alkyl" of the present invention refers to the number of carbon atoms in the unsubstituted "alkyl" group and does not include the number of carbon atoms in the substituent. The "C6-C30" in the "substituted or unsubstituted C6-C30 aryl" refers to the number of carbon atoms in the unsubstituted "aryl" group and does not include the number of carbon atoms in the substituent. And so on.

[0026] The alkyl group herein refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has a carbon number of C1 to C15, preferably C1 to C10. Examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and tridecyl.

[0027] The chain alkyl group having more than three carbon atoms described in the present invention includes its isomers. For example, propyl includes n-propyl and isopropyl, butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl, and so on.

[0028] The alkenyl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from an olefin molecule, preferably having 2 to 12 carbon atoms, more preferably 2 to 6 carbon atoms, and examples may include ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, etc., but are not limited thereto.

[0029] The alkoxy group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from an alkoxy hydrocarbon molecule, preferably having 1 to 12 carbon atoms, more preferably 1 to 6 carbon atoms. Examples may include methoxy, ethoxy, propoxy, butoxy, etc., but are not limited thereto.

[0030] The aryl group described in the present invention refers to a monovalent group formed by removing a hydrogen atom from the aromatic carbon nucleus of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, and condensed ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentphenyl, naphthyl, indenyl, dihydroindenyl, dihydronaphthyl, tetrahydronaphthyl, phenanthrenyl, triphenylene, anthracenyl, pyrenyl, fluorenyl, spirobifluorenyl, spiroanthrafluorenyl, benzofluorenyl, benzospirobifluorenyl, and the like.

[0031] The alicyclic group described herein refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which may be fully or partially unsaturated. Examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, and cycloheptene. Multiple monocyclic hydrocarbons can be linked in various ways: two rings in a molecule can share a carbon atom to form a spirocycle; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; and several rings can be linked to form a cage-like structure, such as, but not limited to, adamantane, norbornane, and camphane.

[0032] The fused alicyclic and aromatic ring groups of the present invention refer to a monovalent group formed by fusion of an alicyclic and aromatic rings and removal of one hydrogen atom. Examples of the fused alicyclic and aromatic ring groups include, but are not limited to, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, benzocyclopropanyl, benzocyclobutanyl, benzocyclobutenyl, benzocycloheptanyl, and benzocycloheptenyl. The alicyclic rings have a carbon number of C3 to C15, preferably C3 to C10. The aromatic rings have a carbon number of C6 to C30, preferably C6 to C18, and more preferably C6 to C12.

[0033] The heteroaryl group described herein refers to a monovalent group in which at least one aromatic carbon atom in an aromatic group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2-C30, preferably C2-C15, and more preferably C2-C10. The heteroatoms include, but are not limited to, O, S, N, Si, B, P, and the like. The heteroaryl group includes monocyclic heteroaryl groups and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, furyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzodibenzothienyl, carbazolyl, and the like, but are not limited thereto.

[0034] The arylene group described in the present invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon nucleus in an aromatic hydrocarbon molecule. The number of carbon atoms in the arylene group is C6 to C30, preferably C6 to C20, and more preferably C6 to C10. The arylene group includes a monocyclic arylene group, a polycyclic arylene group, a condensed ring arylene group, or a combination thereof. Examples of the arylene group include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrenyl, triphenylene, perylene, pyrenylene, indenylene, fluorenylene, benzofluorenylene, dibenzofluorenylene, spirobifluorenylene, benzospirobifluorenylene, etc.

[0035] The sub-fused ring group of an alicyclic ring and an aromatic ring described in the present invention refers to a general term for a divalent group remaining after the alicyclic ring and aromatic ring are fused together and two hydrogen atoms are removed. Examples of the sub-fused ring group of an alicyclic ring and an aromatic ring may include, but are not limited to, indanylene, indenylene, tetrahydronaphthylene, dihydronaphthylene, benzocyclopropanediylene, benzocyclobutanediylene, benzocyclobutenylene, naphthocyclopentanediylene, etc. The number of carbon atoms in the alicyclic ring is C3-C15, preferably C3-C10. The number of carbon atoms in the aromatic ring is C6-C30, preferably C6-C18.

[0036] The heteroarylene group described in the present invention refers to a divalent group in which at least one carbon atom in the arylene group is replaced by a heteroatom. The number of carbon atoms in the heteroarylene group is C2 to C30, preferably C2 to C20, and more preferably C2 to C10. The heteroatoms include, but are not limited to, the following atoms: O, S, N, Si, B, P, etc. The heteroarylene group includes a monocyclic heteroarylene group, a polycyclic heteroarylene group, a condensed ring heteroarylene group, or a combination thereof. Examples of the heteroarylene group include, but are not limited to, the following groups: pyridylene, pyrimidylene, quinolylene, isoquinolylene, furylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thienylene, benzothienylene, dibenzothienylene, benzodibenzothienylene, etc.

[0037] The term "substituted or unsubstituted" as used herein means not substituted or substituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, an amino group, a cyano group, a nitro group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 alicyclic group, a substituted or unsubstituted C3-C30 cycloalkenyl group, a substituted or unsubstituted C3-C30 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted silyl group, preferably a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C12 alkyl group, a C C3-C12 alicyclic group, C3-C12 heterocycloalkyl group, C6-C30 aryl group, C3-C30 heteroaryl group, substituted or unsubstituted silyl group, when substituted by multiple substituents, the multiple substituents are the same or different from each other; preferably, it means not substituted or substituted by one or more substituents selected from the group consisting of: deuterium atom, fluorine atom, cyano group, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl substituted cyclobutanyl, deuterated cyclobutanyl, cyclopentanyl, methyl substituted cyclopentanyl, ethyl substituted cyclopentanyl, deuterated cyclopentanyl, cyclohexanyl, methyl substituted cyclohexanyl, ethyl substituted cyclohexanyl, n-propyl substituted cyclohexanyl, n-butyl substituted cyclohexanyl, cyclohexane substituted cyclohexanyl, deuterated cyclohexanyl, cycloheptyl, cyclopentenyl, methyl substituted cyclopentenyl, ethyl substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl substituted adamantyl, ethyl substituted adamantyl, deuterated adamantyl, norbornyl, methyl substituted norbornyl, ethyl substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidine The following examples include pyridyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazinyl, ethyl-substituted piperazinyl, phenyl-substituted piperazinyl, naphthyl-substituted piperazinyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracenyl, deuterated anthracenyl, phenanthrenyl, deuterated phenanthrenyl, triphenylene, pyrenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, N-phenylcarbazolyl, dibenzofuranyl, dibenzothiophenyl, trimethylsilyl, and triphenylsilyl. When substituted with multiple substituents, the multiple substituents may be the same or different.

[0038] In the present invention, 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 rings. For example, Can be represented Can be represented And so on.

[0039] In the present specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring.

[0040] For example, Can be represented Can represent Can represent And so on.

[0041] In the present invention, "two adjacent groups can be connected to each other to form a substituted or unsubstituted ring" means that the adjacent groups are combined with each other and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and the heterocycle can be monocyclic or polycyclic groups. In addition, the ring formed by the combination of adjacent groups can be connected to another ring to form a spiro structure. The following examples are shown:

[0042]

[0043] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two. The ring formed by connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a spiro ring or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentane acene, cyclohexene, cyclohexane, cyclohexane acene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene or pyrene, but is not limited thereto.

[0044] The present invention provides a star-shaped triamine compound having the general formula shown in Structural Formula 1.

[0045]

[0046] The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, at least four of which are selected from the groups shown in Formula 2, and the remaining identical or different groups are selected from the following groups:

[0047]

[0048] The v is selected from C (R1) or N atoms the same or different, and the v at the bonding site is selected from C;

[0049] Said Y1 is selected from an O atom, a S atom or N(R3);

[0050] Said Y2 is selected from N(R3);

[0051] The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0052] The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring;

[0053] The R3 is the same or different and is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group;

[0054] In Formula 2, X is selected from an O atom or a S atom, provided that when Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are simultaneously selected from Formula 2, X is not simultaneously selected from a S atom;

[0055] The z are identical or different and are selected from C(R a ) or a N atom, and z at the bonding site is selected from C;

[0056] The R a any one of hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R a are connected to each other to form a substituted or unsubstituted ring;

[0057] The L1, L2, L3, L4, L5, and L6 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused sub-ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

[0058] In the present invention, there is no other substituent on the benzene ring to which the three amino groups are connected, indicating that it is only substituted by hydrogen.

[0059] Preferably, the formula 1 is selected from any one of the following structures:

[0060]

[0061]

[0062] Wherein, X, z, L1 to L6, and Ar1 to Ar6 are all as described above.

[0063] Preferably, the formula 2 is selected from any one of the following groups:

[0064]

[0065] The R a the same or different selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl any one or more of phenyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, and carbazolyl; when substituted by multiple substituents, the multiple substituents may be the same or different;

[0066] The c is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2 or 3; the c2 is selected from 0, 1 or 2; the c3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0067] Preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, at least four of which are selected from the group shown in Formula 2, and the rest are identical or different from each other and are selected from the groups shown below:

[0068]

[0069]

[0070] Said R1, R2, R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene Any one or more of phenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted by multiple substituents, the multiple substituents are the same or different, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring;

[0071] The R3 are identical or different and are selected from hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl, and any one or more thereof. When the alkyl group is substituted by multiple substituents, the multiple substituents are identical or different.

[0072] Said a1 is independently selected from 0, 1, 2, 3, 4 or 5; said a2 is independently selected from 0, 1, 2, 3 or 4; said a3 is independently selected from 0, 1 or 2; said a4 is independently selected from 0, 1, 2 or 3; said a5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said a6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said a9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0073] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or combinations thereof:

[0074]

[0075] Said T1 is selected from an O atom, a S atom, N(R6) or C(R7R8);

[0076] Said T2 is selected from O atom, S atom, N(R9);

[0077] The t is selected from C(R5) or N atoms the same or differently; t at the bonding site is selected from C;

[0078] The ring B is selected from a substituted or unsubstituted C3-C15 alicyclic group;

[0079] The R5 are identically or differently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; or two adjacent R5 are connected to each other to form a substituted or unsubstituted ring;

[0080] R7 and R8 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group or a combination thereof; or R7 and R8 may be connected to form a substituted or unsubstituted ring;

[0081] R6 and R9 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group;

[0082] The d1 is independently selected from 0, 1, 2, 3 or 4; the d2 is independently selected from 0, 1, 2 or 3; and the d3 is independently selected from 0, 1 or 2.

[0083] More preferably, L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or combinations thereof:

[0084]

[0085]

[0086] The R5, R 55 independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, silyl, or any combination thereof; or two adjacent R5 are connected to form a substituted or unsubstituted ring;

[0087] R9 is independently selected from hydrogen, deuterium, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, and indolyl;

[0088] The d1 is independently selected from 0, 1, 2, 3 or 4; the d2 is independently selected from 0, 1, 2 or 3; the d3 is independently selected from 0, 1 or 2; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0089] Further preferably, L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or combinations thereof:

[0090]

[0091]

[0092] Most preferably, the star-shaped triamine compound represented by Formula 1 is selected from any one of the chemical structures shown below:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] The above lists some specific chemical structures of the star-shaped triamine compounds of structural formula 1 of the present invention, but the present invention is not limited to these listed chemical structures. All star-shaped triamine compounds based on structural formula 1 and substituents of the groups defined above should be included.

[0167] Furthermore, 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 one or more electrodes of the anode and the cathode, and the organic layer contains the star-shaped triamine compound described in the present invention.

[0168] Preferably, the organic layer is located between the anode and the cathode or on the outside of one or more electrodes of the anode and the cathode, and the organic layer includes at least one layer of a hole transport region, a light-emitting layer, an electron transport region, and a covering layer, and at least one layer of the hole transport region or the covering layer contains the star-shaped triamine compound described in the present invention.

[0169] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, two or more light-emitting layers, a charge generation layer and an electron transport region. The charge generation layer is located between the two light-emitting layers, and the charge generation layer contains the star-shaped triamine compound described in the present invention.

[0170] Preferably, the hole transport region comprises at least one layer of a hole injection layer, a hole transport layer, and an electron blocking layer, the hole injection layer is located between the anode and the cathode, the hole transport layer is located between the hole injection layer and the cathode, and the electron blocking layer is located between the hole transport layer and the cathode, and at least one layer of the hole injection layer, the hole transport layer, and the electron blocking layer contains the star-shaped triamine compound represented by Formula 1 of the present invention.

[0171] Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer comprises the star-shaped triamine compound represented by Formula 1 of the present invention.

[0172] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer contains the star-shaped triamine compound represented by Formula 1 of the present invention.

[0173] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the second hole transport layer contains the star-shaped triamine compound represented by Formula 1 of the present invention.

[0174] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, and the first hole transport layer and the second hole transport layer contain the star-shaped triamine compound represented by Formula 1 of the present invention.

[0175] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer and a third hole transport layer, the second hole transport layer is located between the first hole transport layer and the cathode, the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer and the third hole transport layer contains the star-shaped triamine compound represented by Formula 1 of the present invention.

[0176] Preferably, the thickness of the hole transport layer is 30 nm to 200 nm.

[0177] Preferably, the thickness of the first hole transport layer is 30 nm to 200 nm, and the thickness of the second hole transport layer is 3 nm to 100 nm.

[0178] Preferably, the thickness of the first hole transport layer is 60 nm to 180 nm.

[0179] Further preferably, the thickness of the first hole transport layer is 80 nm to 140 nm.

[0180] More preferably, the thickness of the first hole transport layer is 100 nm to 120 nm.

[0181] Preferably, the thickness of the second hole transport layer is 5 nm to 90 nm.

[0182] Further preferably, the thickness of the second hole transport layer is 40 nm to 80 nm (red light); the thickness of the second hole transport layer is 20 nm to 60 nm (green light); and the thickness of the second hole transport layer is 5 nm to 30 nm (blue light).

[0183] More preferably, the thickness of the second hole transport layer is 50nm to 70nm (red light); the thickness of the second hole transport layer is 30nm to 50nm (green light); and the thickness of the second hole transport layer is 5nm to 25nm (blue light).

[0184] Preferably, the thickness of the third hole transport layer is 5 nm to 150 nm.

[0185] More preferably, the thickness of the third hole transport layer is 10 nm to 100 nm.

[0186] Preferably, the organic electroluminescent device described in the present invention is a single-layer organic electroluminescent device or a stacked organic electroluminescent device. The single-layer organic electroluminescent device is an organic electroluminescent device containing one light-emitting unit, and the stacked organic electroluminescent device is an organic electroluminescent device formed by connecting N (N≥2) independent light-emitting units in series through a charge generation layer.

[0187] Preferably, the organic electroluminescent device of the present invention is a single-layer organic electroluminescent device, wherein an anode, one or more organic layers and a cathode are sequentially stacked on a substrate.

[0188] Preferably, the organic electroluminescent device described in the present invention is a stacked organic electroluminescent device, wherein a first light-emitting unit emitting light of a first color, an Nth light-emitting unit emitting light of an Nth color, and a charge generation layer for uniformly controlling the charge between the first light-emitting unit and the Nth light-emitting unit are formed between the anode and the cathode, and an n-type charge generation layer and a p-type charge generation layer are included between adjacent light-emitting units.

[0189] Preferably, the organic layer includes a hole transport region, two or more light-emitting layers, an electron transport region and a covering layer, and an n-type charge generation layer and a p-type charge generation layer are arranged in the middle of each light-emitting layer, and the p-type charge generation layer contains the star-shaped triamine compound described in the present invention.

[0190] Preferably, the p-type charge generation layer contains the star-shaped triamine compound of the present invention, or the p-type charge generation layer can be formed by doping the star-shaped triamine compound of the present invention with other materials.

[0191] Preferably, the organic layer includes at least one of a hole transport region, a light-emitting layer, an electron transport region, and a covering layer, the covering layer is located on the side of the cathode away from the anode, and the covering layer contains the star-shaped triamine compound represented by Formula 1 of the present invention.

[0192] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate can be any material, as long as it remains unchanged during the formation of the electrodes and the organic layer. Examples include glass, quartz, plastic, polymer film, silicon, and the like. If the substrate is opaque, the opposing electrode is preferably transparent or translucent.

[0193] 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 organic layer of the organic electroluminescent device mentioned above and the electrodes on both sides of the device are respectively introduced below:

[0194] The anode of the present invention preferably uses a metal, alloy, conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or greater). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[0195] The hole injection material of the present invention is preferably a material capable of reducing the interface barrier between the anode and the hole transport layer. Materials such as those described below, polycyano conjugated organics, radialene compounds, phthalocyanine metal complexes, star-shaped triamine compounds, polymers, and the like. Specific examples may include metalloporphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, star-shaped triamine compounds shown in Formula 1 of the present invention, etc., but are not limited thereto. Star-shaped triamine compounds shown in Formula 1 of the present invention are preferred, and may further include other compounds capable of p-doping.

[0196] The hole transport material of the present invention is preferably a material capable of receiving holes from the anode or hole injection layer and transporting the holes to the light-emitting layer, and has high hole mobility and good stability. The hole transport material of the present invention is located between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer when a hole injection layer is present, and can be a single layer structure or a multilayer structure. As hole transport layer materials, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc. can be used. Specific examples may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(spiro- [9,9'-bis(fluoren-2-yl)-N-phenylamino]biphenyl (BSPB), 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (t-BuDNA), 9,10-di(2-naphthyl)anthracene (DNA), 9,10-diphenylanthracene (DPAnth), poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), and the star-shaped triamine compound represented by Formula 1 of the present invention, but are not limited thereto. The star-shaped triamine compound represented by Formula 1 of the present invention is preferred.

[0197] The electron blocking layer of the present invention preferably has a triplet state (T1) energy level higher than the T1 energy level of the main material in the light-emitting layer, which can block the energy loss of the light-emitting layer material. The HOMO energy level of the electron blocking layer material is between the HOMO energy level of the hole transport layer material and the HOMO energy level of the main material of the light-emitting layer, which facilitates the injection of holes from the positive electrode into the light-emitting layer. At the same time, the electron blocking layer material is required to have a high hole mobility, which facilitates hole transport and reduces the power consumption of the device. The LUMO energy level of the electron blocking layer material is higher than the LUMO energy level of the main material of the light-emitting layer, which acts as an electron blocker. In other words, the electron blocking layer material is required to have a wide band gap (Eg). Electron blocking layer materials that meet the above conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. For example, N4, N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1':4',1"-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives, such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirobifluorene-2-amine; dibenzofuran derivatives, such as N, N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, the star-shaped triamine compound represented by Formula 1 of the present invention, etc., but are not limited thereto. The star-shaped triamine compound represented by Formula 1 of the present invention is preferred.

[0198] The light-emitting layer of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, wherein the host material may be composed of one or more materials.

[0199] As the host material of the light-emitting layer of the present invention, it is preferred to use a substance having a LUMO higher than that of the guest material and a HOMO lower than that of the guest material, for example, a fused aromatic ring derivative, a heterocyclic compound, etc., such as 9,10-di(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tri(pyrene-1-yl)benzene (TPB3), 1,3,5-tri(carbazol-9-yl)benzene (TCP), 14,4',4"-tri(carbazol-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazol-9-yl)biphenyl (CBP ), 9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (DPPA), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (BSPB), etc., but are not limited thereto.

[0200] As the guest material of the light-emitting layer of the present invention, aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc. can be included, for example, 4,4'-bis(4-(9H-carbazol-9-yl)phenyl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)phenyl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenylnaphthacene (Rubrene), coumarin 545T (C-525T) tris(2-phenyl-3-methyl-pyridine)iridium (Ir(3mppy) )3), bis(2-(naphthalene-2-yl)pyridine)(acetylacetonate)iridium(III)(Ir(npy)2acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy)3), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)picolinate (FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)picolinate (Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetonate (FIracac), etc., but not limited thereto.

[0201] The hole blocking layer material of the present invention needs to have good hole blocking ability so as to block holes in the light-emitting layer, such as the following materials, imidazole derivatives, phenanthroline derivatives, metal complexes, triazine derivatives, etc. Specific examples may include 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinolinolato-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluoren-2-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine, but are not limited thereto.

[0202] The electron transport layer material of the present invention can be a single-layer structure or a multi-layer structure, which can include one or more electron transport materials. The electron transport material can generally include a metal complex and / or a nitrogen-containing heterocyclic derivative, wherein the metal complex material can be selected from LiQ, Alq3, etc.; the nitrogen-containing heterocyclic derivative can be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a fused aromatic ring compound having a nitrogen-containing six-membered ring or five-membered ring skeleton, etc. Specific examples include but are not limited to Bathophenanthroline (abbreviation: BPhen), 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(naphthalene-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), etc., but not limited thereto.

[0203] The electron injection layer material of the present invention is preferably a material that can reduce the interface barrier between the cathode and the electron transport layer. For example, metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, 8-hydroxyquinoline cesium, tris (8-hydroxyquinoline) aluminum, etc. In addition, a variety of these compounds can also be used in combination.

[0204] The cathode of the present invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (specifically, a work function of 3.8 eV or less). Materials used for the cathode of the present invention may include metals or alloys thereof, multilayered materials, and the like, such as silver (Ag), aluminum (Al), magnesium (Mg), tin (Sb), magnesium-silver (Mg:Ag), and calcium / magnesium (Ca / Mg), but are not limited thereto.

[0205] The anode and cathode of the present invention can each be formed of a transmissive conductive material, a semi-transmissive reflective conductive material, or a reflective conductive material. Depending on the type of material forming the anode and cathode, the organic electroluminescent device can be a top-emitting type, a bottom-emitting type, or a double-sided emitting type.

[0206] The covering layer of the present invention can be a single-layer structure composed of a single substance, or a single-layer structure or a multi-layer structure composed of different substances. The covering layer material can use organic or inorganic substances with an appropriate refractive index, for example, metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, heterocyclic compounds, etc. Specific examples may include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris (8-hydroxyquinoline) aluminum (III) (Alq3), N, N'-diphenyl-N, N'- (1-naphthyl) -1, 1'-biphenyl-4, 4'-diamine (NPB), 4, 4'-bis (9-carbazole) biphenyl (abbreviated CBP), the star-shaped triamine compound represented by Formula 1 of the present invention, etc., but are not limited thereto. The star-shaped triamine compound represented by Formula 1 of the present invention is preferred.

[0207] 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 ( The present invention also includes, but is not limited to, 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]-alternate-2,7-(9,9-dioctylfluorene)] (PFNBr), triphenylquinoxaline (TPQ), and diphenyl-4-triphenylsilyl-phenylphosphine oxide (TSPO1). In addition, auxiliary N-type charge generation materials may also 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.

[0208] 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, the star-shaped triamine compound represented by Formula 1 of the present invention, etc., but are not limited thereto. The star-shaped triamine compound represented by Formula 1 of the present invention is preferred.

[0209] There are no particular limitations on the methods for preparing the thin films of the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spray coating, screen printing, laser transfer, and the like may be employed, but are not limited thereto. The thickness of each layer is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to form, while if it is too thick, a high driving voltage is required, resulting in reduced efficiency. Therefore, the film thickness is typically 5 nm to 10 μm, more preferably 10 nm to 0.2 μm.

[0210] The organic electroluminescent device of the present invention is mainly used in the field of information display technology, and is widely used in various information displays, such as tablet computers, televisions, mobile phones, smart watches, digital cameras, VR, vehicle-mounted systems, wearable devices, lighting equipment, etc.

[0211] Synthesis Example

[0212] Raw materials and reagents: The present invention has no particular limitations on the raw materials or reagents used in the following synthetic examples. They can be commercially available products or prepared using methods well known to those skilled in the art. All raw materials and reagents used in the present invention are of reagent grade.

[0213] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters, UK); Vario ELcube organic element analyzer (Elementar, Germany).

[0214] There are no particular limitations on the preparation method of the star-shaped triamine compound of Structural Formula 1 of the present invention, and conventional methods known to those skilled in the art may be employed. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the star-shaped triamine compound of Structural Formula 1 of the present invention may be prepared using the synthetic route shown below.

[0215] When Ar1 to Ar6 are different:

[0216]

[0217] When Ar1 is the same as Ar3, Ar2 is the same as Ar4, L1 is the same as L3, and L2 is the same as L4:

[0218]

[0219] When Ar1 is the same as Ar3 and Ar5, Ar2 is the same as Ar4 and Ar6, L1 is the same as L3 and L5, and L2 is the same as L4 and L6:

[0220]

[0221] The X1, X2, and X3 are independently selected from any one of I, Br, and Cl.

[0222] 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.

[0223] Preparation and characterization of compounds

[0224] Description of raw materials, reagents and characterization equipment:

[0225] The present invention has no particular limitation on the sources of the raw materials and reagents used in the following examples. They may be commercially available products or prepared using methods well known to those skilled in the art.

[0226] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0227] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0228] Synthesis Example 1: Preparation of Compound 10

[0229]

[0230] Preparation of intermediate A-10

[0231] Under nitrogen, a-10 (21.58 g, 82.00 mmol), b-10 (16.34 g, 82.00 mmol), and sodium tert-butoxide (11.82 g, 123.00 mmol) dissolved in 400 ml of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.72 g, 0.98 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate A-10 (25.03 g, 80% yield); HPLC purity ≥99.85%. Mass spectrum: m / z: 381.0635 (theoretical value: 381.0646).

[0232] Preparation of intermediate B-10

[0233] Under nitrogen, a reaction flask containing c-10 (10.68 g, 68.00 mmol), d-10 (6.33 g, 68.00 mmol), and sodium tert-butoxide (9.80 g, 102.00 mmol) dissolved in 350 ml of toluene was added. Pd(OAc)2 (0.15 g, 0.68 mmol) and P(t-Bu)3 (1.36 mL, 0.68 mmol, in a 0.5 M solution in toluene) were added with stirring. The mixture was heated under reflux for 4 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure. Recrystallization from toluene / methanol (volume ratio 7:1) afforded intermediate B-10 (9.78 g, 85% yield); HPLC purity ≥99.76%. Mass spectrum m / z: 169.0880 (theoretical value: 169.0891).

[0234] Preparation of intermediate C-10

[0235] Under nitrogen, g-10 (8.65 g, 32.00 mmol), A-10 (24.42 g, 64.00 mmol), and sodium tert-butoxide (6.15 g, 64.00 mmol) dissolved in 300 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.14 g, 0.64 mmol) and X-phos (0.31 g, 0.64 mmol) were added with stirring, and the mixed solution was heated under reflux for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 8:1) to obtain intermediate C-10 (21.75 g, 78% yield); HPLC purity ≥99.89%. Mass spectrum m / z: 870.1041 (theoretical value: 870.1059).

[0236] Preparation of compound 10

[0237] Under nitrogen protection, C-10 (22.66 g, 26.00 mmol), B-10 (4.40 g, 26.00 mmol), and sodium tert-butoxide (3.75 g, 39.00 mmol) were added to a reaction flask and dissolved in 150 ml of toluene. Pd2(dba)3 (0.24 g, 0.26 mmol) and X-Phos (0.25 g, 0.52 mmol) were added with stirring, and the mixed solution of the above reactants was heated under reflux for 6 h. After the reaction was completed, it was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 10 (19.85 g, 76%). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrum m / z: 1003.2173 (theoretical value: 1003.2183). Theoretical element content (%): C 66 H 41 N3 S4: C, 78.93; H, 4.12; N, 4.18. Measured element content (%): C, 78.95; H, 4.07; N, 4.12.

[0238] Synthesis Example 2: Preparation of Compound 15

[0239]

[0240] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-15, and c-10 was replaced with an equal molar amount of c-15 to obtain compound 15 (19.86 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1017.2325 (theoretical value: 1017.2340). Theoretical element content (%): C 67 H 43N3S4: C, 79.02; H, 4.26; N, 4.13. Measured element content (%): C, 79.05; H, 4.24; N, 4.11.

[0241] Synthesis Example 3: Preparation of Compound 66

[0242]

[0243] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-66, c-10 was replaced with an equal molar amount of c-66, and d-10 was replaced with an equal molar amount of d-66 to obtain compound 66 (20.53 g). The solid purity was ≥99.91% as determined by HPLC. Mass spectrum m / z: 1080.2877 (theoretical value: 1080.2892). Theoretical element content (%): C 69 H 44 D5N3S4Si: C, 76.63; H, 5.03; N, 3.89; Measured element content (%): C, 76.59; H, 5.04; N, 3.91.

[0244] Synthesis Example 4: Preparation of Compound 190

[0245]

[0246] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-190, and c-10 was replaced with an equal molar amount of c-190 to obtain compound 190 (21.85 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 1134.2985 (theoretical value: 1134.2967). Theoretical element content (%): C 76 H 42 D5N3S4: C, 80.39; H, 4.62; N, 3.70. Measured element content (%): C, 80.47; H, 4.59; N, 3.68.

[0247] Synthesis Example 5: Preparation of Compound 202

[0248]

[0249] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-202, b-10 was replaced with an equal molar amount of b-66, and d-10 was replaced with an equal molar amount of d-202 to obtain Compound 202 (20.37 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1043.2475 (theoretical value: 1043.2496). Theoretical element content (%): C 69 H 45N3S4: C, 79.35; H, 4.34; N, 4.02; Measured element content (%): C, 79.34; H, 4.36; N, 4.00.

[0250] Synthesis Example 6: Preparation of Compound 233

[0251]

[0252] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of d-10, c-10 was replaced with an equal molar amount of a-10, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 233 (19.32 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1003.2193 (theoretical value: 1003.2183). Theoretical element content (%): C 66 H 41 N3S4: C, 78.93; H, 4.12; N, 4.18. Measured element content (%): C, 78.91; H, 4.16; N, 4.20.

[0253] Synthesis Example 7: Preparation of Compound 262

[0254]

[0255] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-262, b-10 was replaced with an equal molar amount of b-262, c-10 was replaced with an equal molar amount of c-202, and d-10 was replaced with an equal molar amount of b-262 to obtain Compound 262 (21.23 g). The solid purity was ≥99.93% as determined by HPLC. Mass spectrum m / z: 1167.3668 (theoretical value: 1167.3686). Theoretical element content (%): C 78 H 53 D4N3S4: C, 80.17; H, 5.26; N, 3.60. Measured element content (%): C, 80.20; H, 5.24; N, 3.58.

[0256] Synthesis Example 8: Preparation of Compound 278

[0257]

[0258] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-278, b-10 was replaced with an equal molar amount of b-66, c-10 was replaced with an equal molar amount of a-10, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 278 (22.55 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1155.2826 (theoretical value: 1155.2809). Theoretical element content (%): C 78 H 49 N3S4: 81.01; H, 4.27; N, 3.63. Measured element content (%): 81.05; H, 4.25; N, 3.65.

[0259] Synthesis Example 9: Preparation of Compound 369

[0260]

[0261] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-66, c-10 was replaced with an equal molar amount of c-369, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 369 (22.44 g). The solid purity was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1165.2698 (theoretical value: 1165.2687). Theoretical element content (%): C 76 H 51 N3S5, C, 78.25; H, 4.41; N, 3.60. Measured element content (%): C, 78.27; H, 4.38; N, 3.65.

[0262] Synthesis Example 10: Preparation of Compound 375

[0263]

[0264] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-375, c-10 was replaced with an equal molar amount of a-10, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 375 (23.51 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1237.2620 (theoretical value: m / z: 1237.2613). Theoretical element content (%): C 80 H 47 N5O2S4: C, 77.58; H, 3.83; N, 5.65. Measured element content (%): C, 77.53; H, 3.80; N, 5.71.

[0265] Synthesis Example 11: Preparation of Compound 483

[0266]

[0267]

[0268] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-483, b-10 was replaced with an equal molar amount of b-483, and c-10 was replaced with an equal molar amount of c-483 to obtain compound 483 (22.44 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1197.3971 (theoretical value: 1197.3962). Theoretical element content (%): C 84 H 55 N3O4Si: C, 84.18; H, 4.63; N, 3.51. Measured element content (%): C, 84.20; H, 4.67; N, 3.47.

[0269] Synthesis Example 12: Preparation of Compound 520

[0270]

[0271] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-520, and b-10 was replaced with an equal molar amount of b-483 to obtain Compound 520 (21.30 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1091.3743 (theoretical value: 1091.3723). Theoretical element content (%): C 78 H 49 N3O4: C, 85.77; H, 4.52; N, 3.85. Measured element content (%): C, 85.75; H, 4.49; N, 3.88.

[0272] Synthesis Example 13: Preparation of Compound 609

[0273]

[0274] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-483, b-10 was replaced with an equal molar amount of b-609, and c-10 was replaced with an equal molar amount of c-609 to obtain compound 609 (19.40 g). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1029.3550 (theoretical value: 1029.3567). Theoretical element content (%): C 73 H 47 N3O4: C, 85.11; H, 4.60; N, 4.08. Measured element content (%): C, 85.14; H, 4.58; N, 4.05.

[0275] Synthesis Example 14: Preparation of Compound 613

[0276]

[0277] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-613, and b-10 was replaced with an equal molar amount of b-613 to obtain compound 613 (20.79 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1051.4336 (theoretical value: 1051.4349). Theoretical element content (%): C 74 H 57 N3O4: C, 84.46; H, 5.46; N, 3.99. Measured element content (%): C, 84.44; H, 5.50; N, 3.95.

[0278] Synthesis Example 15: Preparation of Compound 638

[0279]

[0280] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-483, b-10 was replaced with an equal molar amount of b-638, and c-10 was replaced with an equal molar amount of c-638 to obtain compound 638 (21.22 g). The solid purity was ≥99.98% as determined by HPLC. Mass spectrum m / z: 989.3236 (theoretical value: 989.3254). Theoretical element content (%): C 70 H 43 N3O4: C, 84.92; H, 4.38; N, 4.24. Measured element content (%): C, 84.89; H, 4.40; N, 4.27.

[0281] Synthesis Example 16: Preparation of Compound 791

[0282]

[0283] Preparation of intermediate A-791

[0284] Under nitrogen, a-791 (11.31 g, 35.00 mmol), b-638 (6.41 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) dissolved in 400 ml of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.31 g, 0.42 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate A-791 (12.06 g, 81% yield); HPLC purity ≥99.80%. Mass spectrum: m / z: 425.1430 (theoretical value: 425.1416).

[0285] Preparation of intermediate B-791

[0286] Under nitrogen, a-483 (8.65 g, 35.00 mmol), b-638 (6.41 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) dissolved in 350 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.08 g, 0.35 mmol) and P(t-Bu)3 (0.70 mL, 0.35 mmol, 0.5 M in toluene) were added with stirring. The mixture was heated under reflux for 4 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate gave intermediate B-791 (10.15 g, 83% yield); HPLC purity ≥99.85%. Mass spectrum: m / z: 349.1120 (theoretical value: 349.1103).

[0287] Preparation of intermediate C-791

[0288] Under nitrogen, c-791 (8.16 g, 35.00 mmol), d-791 (5.92 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 35.00 mmol) dissolved in 350 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.08 g, 0.35 mmol) and X-phos (0.17 g, 0.35 mmol) were added with stirring, and the mixed solution was heated under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The intermediate C-791 (21.75 g, 78% yield) was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 8:1) to obtain intermediate C-791 (HPLC purity ≥99.84%). Mass spectrum m / z: 324.1528 (theoretical value: 324.1517).

[0289] Preparation of intermediate D-791

[0290] Under nitrogen, g-791 (8.57 g, 27.00 mmol), A-791 (11.49 g, 27.00 mmol), and sodium tert-butoxide (3.89 g, 40.50 mmol) dissolved in 300 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.06 g, 0.27 mmol) and X-phos (0.13 g, 0.27 mmol) were added with stirring, and the mixed solution was heated under reflux for 5.5 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The intermediate D-791 (13.12 g, 79% yield) was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 10:1) to obtain intermediate D-791 (10.12 g, 79% yield); HPLC purity ≥99.84%. Mass spectrum m / z: 613.0455 (theoretical value: 613.0444).

[0291] Preparation of intermediate E-791

[0292] Under nitrogen, D-791 (12.30 g, 20.00 mmol), B-791 (6.99 g, 20.00 mmol), and sodium tert-butoxide (2.88 g, 30.00 mmol) dissolved in 250 ml of toluene were added to a reaction flask. Pd(OAc)2 (0.09 g, 0.40 mmol) and X-phos (0.19 g, 0.40 mmol) were added with stirring, and the mixed solution was heated under reflux for 6 h. After the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The intermediate E-791 (13.43 g, 76% yield) was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 8:1) to obtain intermediate E-791 (HPLC purity ≥99.44%). Mass spectrum m / z: 882.2268 (theoretical value: 882.2285).

[0293] Preparation of Compound 791

[0294] Under nitrogen, E-791 (13.25 g, 15.00 mmol), C-791 (4.82 g, 15.00 mmol), and sodium tert-butoxide (2.16 g, 22.50 mmol) dissolved in 150 ml of toluene were added to a reaction flask. Pd2(dba)3 (0.14 g, 0.15 mmol) and X-Phos (0.14 g, 0.30 mmol) were added with stirring, and the mixed solution was heated under reflux for 7 h. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 791 (13.14 g, 75%). HPLC analysis showed that the solid purity was ≥99.97%. Mass spectrum m / z: 1167.4048 (theoretical value: 1167.4036). Theoretical element content (%): C 84 H 53 N3O4: C, 86.35; H, 4.57; N, 3.60. Measured element content (%): C, 86.37; H, 4.54; N, 3.63.

[0295] Synthesis Example 17: Preparation of Compound 823

[0296]

[0297] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-823, b-10 was replaced with an equal molar amount of b-483, and c-10 was replaced with an equal molar amount of c-823 to obtain compound 823 (20.28 g). The purity of the solid was ≥99.97% as determined by HPLC. Mass spectrum m / z: 1039.3428 (theoretical value: 1039.3410). Theoretical element content (%): C 74 H 45 N3O4: C, 85.45; H, 4.36; N, 4.04. Measured element content (%): C, 85.50; H, 4.38; N, 4.00.

[0298] Synthesis Example 18: Preparation of Compound 844

[0299]

[0300] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-613, b-10 was replaced with an equal molar amount of b-483, and c-10 was replaced with an equal molar amount of c-844 to obtain compound 844 (20.87 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1055.3738 (theoretical value: 1055.3723). Theoretical element content (%): C 75 H 49N3O4: C, 85.29; H, 4.68; N, 3.98. Measured element content (%): C, 85.34; H, 4.65; N, 3.95.

[0301] Synthesis Example 19: Preparation of Compound 870

[0302]

[0303] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-483, b-10 was replaced with an equal molar amount of b-638, and c-10 was replaced with an equal molar amount of c-870 to obtain compound 870 (19.11 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 979.3065 (theoretical value: 979.3046). Theoretical element content (%): C 68 H 41 N3O5: C, 83.33; H, 4.22; N, 4.29. Measured element content (%): C, 83.30; H, 4.26; N, 4.25.

[0304] Synthesis Example 20: Preparation of Compound 912

[0305]

[0306] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-813, b-10 was replaced with an equal molar amount of d-10, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of d-912 to obtain compound 912 (18.58 g). The solid purity was ≥99.97% by HPLC. Mass spectrum m / z: 939.3086 (theoretical value: 939.3097). Theoretical element content (%): C 66 H 41 N3O4, C, 84.33; H, 4.40; N, 4.47. Measured element content (%): C, 84.36; H, 4.44; N, 4.42.

[0307] Synthesis Example 21: Preparation of Compound 935

[0308]

[0309] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-935, b-10 was replaced with an equal molar amount of b-483, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 935 (18.74 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 973.3770 (theoretical value: 973.3787). Theoretical element content (%): C 68 H 39 D6N3O4: C, 83.84; H, 5.28; N, 4.31. Measured element content (%): C, 83.79; H, 5.31; N, 4.36.

[0310] Synthesis Example 22: Preparation of Compound 969

[0311]

[0312] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-969, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 969 (18.88 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 967.3423 (theoretical value: 967.3410). Theoretical element content (%): C 68 H 45 N3O4: C, 84.36; H, 4.69; N, 4.34. Measured element content (%): C, 84.40; H, 4.64; N, 4.38.

[0313] Synthesis Example 23: Preparation of Compound 1060

[0314]

[0315] According to the preparation method of Synthesis Example 1, compound 1060 (20.44 g) was obtained by replacing a-10 with an equal molar amount of a-1060, b-10 with an equal molar amount of b-483, c-10 with an equal molar amount of a-823, and d-10 with an equal molar amount of b-483. The solid purity was ≥99.97% as determined by HPLC. Mass spectrum: m / z: 1111.3135 (theoretical: 1111.3122). Theoretical element content (%): C74H53N3S4: C, 79.89; H, 4.80; N, 3.78. Measured element content (%): C, 79.89; H, 4.80; N, 3.78.

[0316] Synthesis Example 24: Preparation of Compound 1062

[0317]

[0318] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1062, b-10 was replaced with an equal molar amount of b-483, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 1062 (22.44 g). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1181.4995 (theoretical value: 1181.4977). Theoretical element content (%): C 84 H 47 D 10 N3O4: C, 85.32; H, 5.71; N, 3.55. Measured element content (%): C, 85.30; H, 5.75; N, 3.58.

[0319] Synthesis Example 25: Preparation of Compound 1064

[0320]

[0321] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1064, b-10 was replaced with an equal molar amount of b-483, c-10 was replaced with an equal molar amount of a-613, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 1064 (22.56 g). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1171.4335 (theoretical value: 1171.4349). Theoretical element content (%): C 84 H 57 N3O4: C, 86.06; H, 4.90; N, 3.58. Measured element content (%): C, 86.08; H, 4.95; N, 3.54.

[0322] Synthesis Example 26: Preparation of Compound 1083

[0323]

[0324] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1083, b-10 was replaced with an equal molar amount of b-483, c-10 was replaced with an equal molar amount of c-613, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 1063 (20.25 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1051.2554 (theoretical value: 1051.2538). Theoretical element content (%): C 70 H 41 N3O4S2: C, 79.90; H, 3.93; N, 3.99. Measured element content (%): C, 79.94; H, 3.89; N, 3.95.

[0325] Synthesis Example 27: Preparation of Compound 1270

[0326]

[0327] Under nitrogen, g-1270 (8.50 g, 27.00 mmol), A-823 (28.30 g, 81.00 mmol), and sodium tert-butoxide (5.19 g, 54.00 mmol) dissolved in 300 ml of toluene were added to a reaction flask. Pd2(dba)3 (0.49 g, 0.54 mmol) and P(t-Bu)3 (2.16 mL, 1.08 mmol, in a 0.5 M toluene solution) were added with stirring. The mixed solution was heated under reflux for 6 h. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Compound 1270 was recrystallized from toluene to obtain 22.08 g, 73%. The solid purity was ≥99.92% as determined by HPLC. Mass spectrum: m / z: 1119.3326 (theoretical value: 1119.3308). Theoretical element content (%) C 78 H 45 N3O6, C, 83.63; H, 4.05; N, 3.75. Measured element content (%): C, 83.66; H, 4.10; N, 3.70.

[0328] Synthesis Example 28: Preparation of Compound 1457

[0329]

[0330] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-483, and c-10 was replaced with an equal molar amount of c-1457 to obtain compound 1457 (21.93 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1123.3254 (theoretical value: 1123.3266). Theoretical element content (%): C 78 H 49 N3O2S2: C, 83.32; H, 4.39; N, 3.74. Measured element content (%): C, 83.29; H, 4.35; N, 3.78.

[0331] Synthesis Example 29: Preparation of Compound 1620

[0332]

[0333] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1620, b-10 was replaced with an equal molar amount of d-66, c-10 was replaced with an equal molar amount of a-10, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 1620 (20.91 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1071.2970 (theoretical value: 1071.2953). Theoretical element content (%): C 74 H 45 N3O2S2: C, 82.89; H, 4.23; N, 3.92. Measured element content (%): C, 82.91; H, 4.25; N, 3.89.

[0334] Synthesis Example 30: Preparation of Compound 1630

[0335]

[0336] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1630, b-10 was replaced with an equal molar amount of d-10, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-483 to obtain compound 1630 (20.63 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1071.2937 (theoretical value: 1071.2953). Theoretical element content (%): C 74 H 45 N3O2S2: C, 82.89; H, 4.23; N, 3.92. Measured element content (%): C, 82.92; H, 4.27; N, 3.88.

[0337] Synthesis Example 31: Preparation of Compound 1646

[0338]

[0339] According to the preparation method of Synthesis Example 16, a-791 was replaced with an equal molar amount of a-823, b-638 was replaced with an equal molar amount of b-483, c-791 was replaced with an equal molar amount of c-638, and d-791 was replaced with an equal molar amount of d-1646 to obtain compound 1646 (20.54 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1039.3426 (theoretical value: 1039.3410). Theoretical element content (%): C 74 H 45 N3O4: C, 85.45; H, 4.36; N, 4.04. Measured element content (%): C, 85.41; H, 4.32; N, 4.07.

[0340] Synthesis Example 32: Preparation of Compound 1692

[0341]

[0342] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-912, b-10 was replaced with an equal molar amount of d-10, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of d-1692 to obtain compound 1692 (18.40 g). The solid purity was ≥99.92% as determined by HPLC. Mass spectrum m / z: 955.2854 (theoretical value: 955.2869). Theoretical element content (%): C 66 H 41 N3O3S: C, 82.91; H, 4.32; N, 4.39. Measured element content (%): C, 82.87; H, 4.37; N, 4.36.

[0343] Synthesis Example 33: Preparation of Compound 1763

[0344]

[0345] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-483, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 1763 (22.25 g). The solid purity was ≥99.94% as determined by HPLC. Mass spectrum m / z: 1155.3476 (theoretical value: 1155.3495). Theoretical element content (%): C 82 H 49 N3O3S, C, 85.17; H, 4.27; N, 3.63. Measured element content (%): C, 85.14; H, 4.22; N, 3.66.

[0346] Synthesis Example 34: Preparation of Compound 1795

[0347]

[0348] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-1785, b-10 was replaced with an equal molar amount of d-10, a-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of b-66 to obtain compound 1795 (21.79 g). The purity of the solid was ≥99.91% as determined by HPLC. Mass spectrum m / z: 1131.3222 (theoretical value: 1131.3202). Theoretical element content (%): C 72 H 57N3OS3Si2: C, 76.35; H, 5.07; N, 3.71. Measured element content (%): C, 76.32; H, 5.09; N, 3.68.

[0349] Synthesis Example 35: Preparation of Compound 1893

[0350]

[0351] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-202, b-10 was replaced with an equal molar amount of b-1692, c-10 was replaced with an equal molar amount of c-1893, and d-10 was replaced with an equal molar amount of d-1893 to obtain compound 1893 (22.54 g). The purity of the solid was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1170.2577 (theoretical value: 1170.2554). Theoretical element content (%): C 77 H 46 N4OS4: C, 78.95; H, 3.96; N, 4.78. Measured element content (%): C, 78.97; H, 3.99; N, 4.73.

[0352] Synthesis Example 36: Preparation of Compound 2047

[0353]

[0354] According to the preparation method of Synthesis Example 1, a-10 was replaced with an equal molar amount of a-483, b-10 was replaced with an equal molar amount of d-1692, c-10 was replaced with an equal molar amount of a-823, and d-10 was replaced with an equal molar amount of d-2047 to obtain compound 2047 (20.71 g). The solid purity was ≥99.96% as determined by HPLC. Mass spectrum m / z: 1209.3465 (theoretical value: 1209.3454). Theoretical element content (%): C 81 H 55 N3O3S2Si: C, 80.37; H, 4.58; N, 3.47. Measured element content (%): C, 80.35; H, 4.61; N, 3.44.

[0355] Synthesis Example 37: Preparation of Compound 2173

[0356]

[0357] According to the preparation method of Synthesis Example 27, A-823 was replaced with an equal molar amount of B-1763 to obtain compound 2173 (23.34 g). The solid purity was ≥99.95% by HPLC. Mass spectrum m / z: 1167.2643 (theoretical value: 1167.2623). Theoretical element content (%) C 78 H 45 N3O3S3: C, 80.18; H, 3.88; N, 3.60. Measured element content (%): C, 80.20; H, 3.85; N, 3.64.

[0358] Synthesis Example 38: Preparation of Compound 2241

[0359]

[0360] According to the preparation method of Synthesis Example 1, b-10 was replaced with an equal molar amount of b-483, and c-10 was replaced with an equal molar amount of c-369 to obtain compound 2241 (20.71 g). The solid purity was ≥99.95% as determined by HPLC. Mass spectrum m / z: 1105.3755 (theoretical value: 1105.3736). Theoretical element content (%): C 76 H 55 N3O2S2: C, 82.50; H, 5.01; N, 3.80. Measured element content (%): C, 82.47; H, 5.03; N, 3.78;.

[0361] Device Examples

[0362] In the present invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, then ultrasonically cleaned twice with deionized water for 10 minutes each time. The substrate is then ultrasonically cleaned for 20 minutes each in acetone and isopropyl alcohol, followed by drying at 120°C. All organic materials are sublimated to a purity of over 99.99%.

[0363] 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 driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifespan tests were conducted using a McScience M6000 OLED Lifespan Test System. The test environment was ambient air and room temperature.

[0364] The device is prepared using a vacuum evaporation system, which is completed by continuous evaporation under uninterrupted vacuum conditions. The materials used are placed in different evaporation source quartz crucibles, and the temperature of the evaporation source can be controlled individually. The thermal evaporation rate of organic materials is generally set at 0.1nm / s, and the evaporation rate of electrode metals is 0.4~0.6nm / s. The processed glass substrate is placed in the OLED vacuum coating machine. During the film production process, the system vacuum degree should be maintained at 5×10 -5 Pa, the organic layer and metal electrode are evaporated separately by replacing the mask plate, the evaporation speed is detected by Inficon's SQM160 quartz crystal film thickness detector, and the film thickness is detected by a quartz crystal oscillator.

[0365] Example 1: Preparation of organic electroluminescent device 1

[0366] ITO was used as an anode on a glass substrate; 22 nm of HT-1:HI-1 (mixed in a mass ratio of 97%:3%) was vacuum evaporated on the anode to form a hole injection layer; 120 nm of the compound 10 of the present invention was vacuum evaporated on the hole injection layer to form a hole transport layer; 35 nm of GH-1:GD-1 (mixed in a mass ratio of 97%:3%) was vacuum evaporated on the hole transport layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF was vacuum evaporated on the electron transport layer to form an electron injection layer; and 120 nm of Al was vacuum evaporated on the electron injection layer to form a cathode.

[0367] Examples 2 to 38: Preparation of organic electroluminescent devices 2 to 38

[0368] The compound 10 in the hole transport layer of Example 1 was replaced by compound 15, compound 66, compound 190, compound 202, compound 233, compound 262, compound 278, compound 369, compound 375, compound 483, compound 520, compound 609, compound 613, compound 638, compound 791, compound 823, compound 844, compound 870, compound 912, compound 935, compound 969, compound 1060, compound 1062, compound 1064, compound 1083, compound 1270, compound 1457, compound 1620, compound 1630, compound 1646, compound 1692, compound 1763, compound 1795, compound 1893, compound 2047, compound 2173, and compound 2241, respectively. The other steps were the same to obtain organic electroluminescent devices 2 to 38.

[0369] Comparative Examples 1 to 3: Preparation of Comparative Organic Electroluminescent Devices 1 to 3

[0370] The compound 10 in the hole transport layer of Example 1 was replaced by R-1, R-2, and R-3, respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 1 to 3.

[0371]

[0372] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 1 to 38 of the present invention and Comparative Examples 1 to 3 are shown in Table 1.

[0373] Table 1 Luminescence characteristics test data of organic electroluminescent devices

[0374]

[0375]

[0376] Note: T95 refers to the current density of 10mA / cm 2 Under the condition of , the time taken for the device brightness to decay to 95%;

[0377] It can be concluded from Table 1 that, compared with Comparative Examples 1 to 3, the star-shaped triamine compound represented by Formula 1 of the present invention, when used in the hole transport layer of the organic electroluminescent device, effectively improves the efficiency of the organic electroluminescent device and improves the service life of the device, further demonstrating that the compound of the present invention has excellent hole transport ability.

[0378] Example 39: Preparation of organic electroluminescent device 39

[0379] ITO was used as the anode on a glass substrate; 20 nm of HT-2:HI-1 (mixed in a mass ratio of 96%:4%) was vacuum evaporated on the anode to form a hole injection layer; 80 nm of HT-2 was vacuum evaporated on the hole injection layer to form a first hole transport layer; 40 nm of compound 10 was vacuum evaporated on the first hole transport layer to form a second hole transport layer, and 36 nm of RH-1:RH-2:RD-1 (mixed in a mass ratio of 100%:100%:20%) was vacuum evaporated on the second hole transport layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF was vacuum evaporated on the electron transport layer to form an electron injection layer; and 120 nm of Al was vacuum evaporated on the electron injection layer to form a cathode.

[0380] Examples 40-76: Preparation of organic electroluminescent devices 40-76

[0381] The compound 10 in the second hole transport layer of Example 39 was replaced by compound 15, compound 66, compound 190, compound 202, compound 233, compound 262, compound 278, compound 369, compound 375, compound 483, compound 520, compound 609, compound 613, compound 638, compound 791, compound 823, compound 844, compound 870, compound 912, compound 935, compound 969, compound 1060, compound 1062, compound 1064, compound 1083, compound 1270, compound 1457, compound 1620, compound 1630, compound 1646, compound 1692, compound 1763, compound 1795, compound 1893, compound 2047, compound 2173, and compound 2241, respectively, and the other steps were the same to obtain organic electroluminescent devices 40 to 76.

[0382] Comparative Examples 4 to 6: Preparation of Comparative Organic Electroluminescent Devices 4 to 6

[0383] The compound 10 in the second hole transport layer of Example 39 was replaced by compound R-1, compound R-2, and compound R-4, respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 4 to 6.

[0384]

[0385] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 39 to 76 of the present invention and Comparative Examples 4 to 6 are shown in Table 2.

[0386] Table 2 Luminescence characteristics test data of organic electroluminescent devices

[0387]

[0388]

[0389] Note: T95 refers to the current density of 10mA / cm 2 Under the condition of , the time taken for the device brightness to decay to 95%;

[0390] As can be seen from the results in Table 2, the star-shaped triamine compound represented by Formula 1 of the present invention is applied to an organic electroluminescent device. When used as a second hole transport layer material in the device, the performance of the device is significantly improved compared with Comparative Examples 4 to 6, showing the advantages of high luminous efficiency and long service life, indicating that it has good hole transport ability.

[0391] Example 77: Preparation of organic electroluminescent device 77

[0392] ITO / Ag / ITO was used as the anode on a glass substrate; 25 nm of HT-2:HI-1 (mixed in a mass ratio of 97%:3%) was vacuum evaporated on the anode to form a hole injection layer; 110 nm of HT-2 was vacuum evaporated on the hole injection layer to form a hole transport layer; 38 nm of BH-1:BD-1 (mixed in a mass ratio of 97%:3%) was vacuum evaporated on the hole transport layer to form a light-emitting layer; 30 nm of ET-1:LiQ (mixed in a mass ratio of 1:1) was vacuum evaporated on the light-emitting layer to form an electron transport layer; 1.0 nm of LiF was vacuum evaporated on the electron transport layer to form an electron injection layer; 10 nm of Mg and Ag (mass ratio of 1:9) was vacuum evaporated on the electron injection layer to form a cathode, and 80 nm of compound 10 was evaporated on the cathode to form a covering layer.

[0393] Examples 78-102: Preparation of organic electroluminescent devices 78-102

[0394] The compound 10 in the covering layer of Example 77 was replaced by compound 15, compound 190, compound 233, compound 278, compound 369, compound 375, compound 483, compound 520, compound 638, compound 791, compound 823, compound 870, compound 912, compound 935, compound 969, compound 1062, compound 1270, compound 1457, compound 1620, compound 1630, compound 1646, compound 1692, compound 1763, compound 2173, and compound 2241, respectively, and the other steps were the same to obtain organic electroluminescent devices 78 to 102.

[0395] Comparative Examples 7-8: Preparation of Comparative Organic Electroluminescent Devices 7-8

[0396] The compound 10 in the covering layer of Example 77 was replaced by R-1 and R-2 respectively, and the other steps were the same to obtain comparative organic electroluminescent devices 7 to 8.

[0397]

[0398] The test results of the luminescence characteristics of the organic electroluminescent devices prepared in Examples 77 to 102 of the present invention and Comparative Examples 7 to 8 are shown in Table 3.

[0399] Table 3 Luminescence characteristics test data of organic electroluminescent devices

[0400]

[0401]

[0402] Note: T95 refers to the current density of 10mA / cm 2Under the condition of , the time taken for the device brightness to decay to 95%;

[0403] It can be seen from the results in Table 3 that when the star-shaped triamine compound of the present invention is applied to the cover layer of an organic electroluminescent device, the luminous efficiency and service life of the device are greatly improved.

[0404] In summary, the star-shaped triamine compounds provided by the present invention are a class of OLED materials with excellent performance and have great application prospects.

[0405] 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 compound, characterized in that: Having the general formula shown in structural formula 1, The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, at least four of which are selected from the groups shown in Formula 2, and the remaining identical or different groups are selected from the following groups: The v is selected from C (R1) or N atoms the same or different, and the v at the bonding site is selected from C; Said Y1 is selected from an O atom, a S atom or N(R3); Said Y2 is selected from N(R3); The ring A is selected from a substituted or unsubstituted C3-C15 alicyclic group; The R1 and R2 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R1 are connected to each other to form a substituted or unsubstituted ring; The R3 is the same or different and is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, and substituted or unsubstituted C2-C30 heteroaryl group; In Formula 2, X is selected from an O atom or a S atom, provided that when Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are simultaneously selected from Formula 2, X is not simultaneously selected from a S atom; The z are identical or different and are selected from C(R a ) or a N atom, and z at the bonding site is selected from C; The R a any one of hydrogen, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused ring of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl; or the two adjacent R a are connected to each other to form a substituted or unsubstituted ring; The L1, L2, L3, L4, L5, and L6 are independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused sub-ring group, and a substituted or unsubstituted C2-C30 heteroarylene group.

2. The star-shaped triamine compound according to claim 1, characterized in that The formula 1 is selected from any one of the following structures: Wherein, X, z, L1-L6, Ar1-Ar6 are all as described in claim 1.

3. The star-shaped triamine compound according to claim 1, characterized in that The formula 2 is selected from any one of the groups shown below: The R a the same or different selected from hydrogen, cyano, halogen, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl any one or more of phenyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, and carbazolyl; when substituted by multiple substituents, the multiple substituents may be the same or different; The c is selected from 0, 1, 2, 3 or 4; the c1 is selected from 0, 1, 2 or 3; the c2 is selected from 0, 1 or 2; the c3 is selected from 0, 1, 2, 3, 4, 5 or 6; the c4 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

4. The star-shaped triamine compound according to claim 1, characterized in that The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are identical or different from each other, at least four of which are selected from the groups shown in Formula 2, and the remaining identical or different groups are selected from the following groups: Said R1, R2, R4 are the same or different and are selected from hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracene Any one or more of phenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furanyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, and silyl; when substituted by multiple substituents, the multiple substituents are the same or different, or the two adjacent R1s are connected to each other to form a substituted or unsubstituted ring; The R3 are identical or different and are selected from hydrogen, deuterium, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, dihydroindenyl, indenyl, tetrahydronaphthyl, dihydronaphthyl, anthracenyl, phenanthrenyl, triphenylene, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, indolyl, furyl, thienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, carbazolyl, silyl, and any one or more thereof. When the alkyl group is substituted by multiple substituents, the multiple substituents are identical or different. Said a1 is independently selected from 0, 1, 2, 3, 4 or 5; said a2 is independently selected from 0, 1, 2, 3 or 4; said a3 is independently selected from 0, 1 or 2; said a4 is independently selected from 0, 1, 2 or 3; said a5 is independently selected from 0, 1, 2, 3, 4, 5, 6 or 7; said a6 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said a7 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; said a8 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; said a9 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

5. The star-shaped triamine compound according to claim 1, characterized in that The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or combinations thereof: Said T1 is selected from an O atom, a S atom, N(R6) or C(R7R8); Said T2 is selected from O atom, S atom, N(R9); The t is selected from C(R5) or N atoms the same or differently; t at the bonding site is selected from C; The ring B is selected from a substituted or unsubstituted C3-C15 alicyclic group; The R5 are identically or differently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group; or two adjacent R5 are connected to each other to form a substituted or unsubstituted ring; R7 and R8 are independently selected from any one of hydrogen, deuterium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl group, fused ring group of substituted or unsubstituted C3-C15 alicyclic ring and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl group or a combination thereof; or R7 and R8 may be connected to form a substituted or unsubstituted ring; R6 and R9 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring fused ring group, substituted or unsubstituted C2-C30 heteroaryl group; The d1 is independently selected from 0, 1, 2, 3 or 4; the d2 is independently selected from 0, 1, 2 or 3; and the d3 is independently selected from 0, 1 or 2.

6. The star-shaped triamine compound according to claim 1, characterized in that The L1, L2, L3, L4, L5, and L6 are independently selected from a single bond or any one of the following groups or combinations thereof: The R5, R 55 independently selected from hydrogen, deuterium, halogen, cyano, nitro, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, silyl, or any combination thereof; or two adjacent R5 are connected to form a substituted or unsubstituted ring; R9 is independently selected from hydrogen, deuterium, or substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, tetrahydronaphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclohexyl, silyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, benzofuranyl, benzothiophenyl, and indolyl; The d1 is independently selected from 0, 1, 2, 3 or 4; the d2 is independently selected from 0, 1, 2 or 3; the d3 is independently selected from 0, 1 or 2; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6; the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

7. The star-shaped triamine compound according to claim 1, characterized in that The star-shaped triamine compound represented by Formula 1 is selected from any one of the following chemical structures:

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 one or more of the anode and the cathode, wherein: The organic layer contains the star-shaped triamine compound according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode or on the outside of one or more electrodes of the anode and the cathode, and the organic layer includes at least one layer of a hole transport region, a light-emitting layer, an electron transport region, and a covering layer, and at least one layer of the hole transport region or the covering layer contains the star-shaped triamine compound according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that: The organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, two or more light-emitting layers, a charge generation layer and an electron transport region. The charge generation layer is located between the two light-emitting layers, and the charge generation layer contains the star-shaped triamine compound according to any one of claims 1 to 7.

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