A triarylamine compound and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine compound and an organic electroluminescent device thereof, and particularly relates to the technical field of organic electroluminescent materials.The triarylamine compound has high hole mobility, good thermal stability and good film-forming property, and when the triarylamine compound is applied to a hole transport layer in an organic electroluminescent device, the energy barrier in the hole injection process can be reduced, the hole injection efficiency can be improved, the hole transport rate and the electron transport can be balanced, the recombination probability of excitons in the light-emitting layer can be improved, the maximum recombination of carriers can be realized, and the light-emitting efficiency of the device and the service life of the device can be improved.Therefore, the compound has great application value and commercial value in the application of OLED devices, and has good industrialization prospects.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) are currently the most promising new display technology. This is because OLEDs have characteristics such as being all-solid-state, actively emitting light, having high contrast, low power consumption, no viewing angle limitations, fast response speed, wide operating range, and easy to realize flexible and 3D displays. Their applications in many fields such as display and lighting are increasing, attracting widespread attention at home and abroad, and gradually becoming a research focus in related industries.

[0003] In organic light-emitting diodes (OLEDs), electrons and holes are injected from the cathode and anode into the organic layer under the drive of an applied voltage. They then migrate within the organic layer, recombine to form excitons, which emit light through radiative decay. The basic structure of OLEDs can be categorized into single-layer, double-layer, triple-layer, and multi-layer structures. However, with the increasing prevalence of OLED applications, single-layer, double-layer, and triple-layer structures are gradually failing to meet market demands. Therefore, to improve device efficiency, most OLEDs today utilize multi-layer structures, which can include numerous functional layers such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer.

[0004] The primary function of hole transport materials is to improve the balance between hole injection and transport in devices, effectively blocking electrons in the light-emitting layer to achieve maximum recombination between charge carriers, thereby improving luminous efficiency. Simultaneously, they lower the energy barrier during hole injection, increasing injection efficiency and ultimately improving device efficiency and lifetime. However, most current hole transport materials suffer from low hole mobility, poor film-forming properties, and poor thermal stability. Since hole transport materials are indispensable in OLED materials, to improve the luminous efficiency and lifespan of OLED devices, they should possess high hole mobility, good thermal stability, and good film-forming properties.

[0005] Although research on hole transport materials has become increasingly mature, many problems still exist when they are applied to devices, such as low luminous efficiency and short lifespan. Therefore, in order to comprehensively improve the performance of organic electroluminescent devices, it is urgent to design high-performance hole transport materials to improve the luminous efficiency and extend the lifespan of the devices. Summary of the Invention

[0006] To address the above problems, this invention provides a triarylamine compound and its organic electroluminescent device. When applied to the hole transport region of an organic electroluminescent device, it can effectively improve the luminous efficiency and extend the lifespan of the organic electroluminescent device. Specifically, the technical solution of this invention is as follows:

[0007] This invention provides a triarylamine compound, which is represented by the structure shown in Formula 1:

[0008]

[0009] A is selected from Equation 2, B is selected from Equation 3, and C is selected from Equation 3;

[0010]

[0011] Y1 is selected from O or S; Y2 is selected from CH, O or S;

[0012] The "--" is selected from none or a single bond; when Y2 is selected from CH, the "--" is selected from a single bond; when Y2 is selected from O or S, the "--" is selected from none.

[0013] The R a R b R1, R2, R3, and R4 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl, and any combination thereof; or adjacent R1, R2, R3, and R4 can be interconnected to form substituted or unsubstituted rings;

[0014] The x values ​​are selected from N or CH, and the x values ​​at the bonding sites are selected from C.

[0015] a is selected from 0, 1, 2, or 3; b is selected from 0, 1, or 2; c is selected from 0, 1, 2, 3, 4, or 5; d is selected from 0, 1, 2, or 3; e is selected from 0, 1, 2, 3, or 4; when there are two or more R a R b When R1, R2, R3, R4, two or more R a R b R1, R2, R3, and R4 are either the same as or different from each other;

[0016] The La Selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutylene, substituted or unsubstituted benzocyclopentylene, substituted or unsubstituted benzocyclohexylene The following are possible combinations of substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocyclopentenyl, substituted or unsubstituted benzocyclohexenyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, and combinations thereof.

[0017] The L b L c It is independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroarylene rings, and combinations thereof.

[0018] The present invention also provides an organic electroluminescent device, the organic electroluminescent device comprising an anode, a cathode, and an organic layer, the organic layer being located between the anode and the cathode or outside at least one of the electrodes of the anode and the cathode, the organic layer containing any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0019] Beneficial effects:

[0020] This invention provides a triarylamine compound and its organic electroluminescent device. The triarylamine compound of this invention has high hole mobility, good thermal stability, and good film-forming properties. When applied to the hole transport layer in an organic electroluminescent device, it can reduce the energy barrier during hole injection, improve hole injection efficiency, balance hole transport rate with electron transport, increase the recombination probability of excitons in the light-emitting layer, and achieve maximum recombination of charge carriers, thereby improving the luminous efficiency of the device and extending its service life. Detailed Implementation

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

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

[0023] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0024] In the specification, "*-" refers to the portion that is connected to another substituent. "*-" can be attached to any optional position of the group / fraction to which it is attached.

[0025] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.

[0026] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0027] In this invention, "forming a ring by connecting two adjacent groups" refers to the formation of a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle by combining adjacent groups with each other and optionally aromatizing them. The aliphatic ring or aliphatic heterocycle can be a saturated ring or an unsaturated ring. The formed ring can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, a spirocyclic ring, or a fused ring. Examples of the formed ring may include, but are not limited to, benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentanophenene, cyclohexene, cyclohexane, cyclohexanophenene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene.

[0028]

[0029] The alkyl group referred to in this invention is a general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group can be substituted or unsubstituted. The straight-chain alkyl group includes, but is not limited to, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl groups; the branched-chain alkyl group includes, but is not limited to, isomers of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and n-decyl groups.

[0030] The alicyclic group mentioned in this invention refers to a monovalent group formed by removing one less hydrogen atom from an alicyclic hydrocarbon molecule. It can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.

[0031] The "substituted or unsubstituted silyl group" mentioned in this invention refers to -Si(R m )3 groups, wherein each R m The group is selected, either identically or differently, from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl rings, and any combination thereof. Preferably, each R m The group may be selected from one of the following groups, either identically or differently: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, etc., but not limited to these groups.

[0032] The aryl group described in this invention refers to the general term for monovalent groups obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The aryl group can be substituted or unsubstituted. The monocyclic aryl refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, triphenylene, fluoranyl, fluorene, etc., but not limited to this.

[0033] The heteroaryl group described in this invention refers to a collective term for monovalent groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and most preferably 3 to 15 carbon atoms. The heteroaryl group can be substituted or unsubstituted. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl, etc. The monocyclic heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; the polycyclic heteroaryl groups include bipyridinyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; the fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, acridineyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, spirofluorenexanthraceneyl, spirofluorenethionthanthraceneyl, etc., but are not limited thereto.

[0034] The fused alicyclic and aromatic rings described in this invention refer to the monovalent group formed by removing one hydrogen atom after the aromatic ring and the alicyclic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0035] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 7 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. Examples may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc., but are not limited thereto.

[0036] The arylene group referred to in this invention is a general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom. Apart from being divalent groups, they are subject to the same description of aryl groups as described above.

[0037] The term "hybrid aryl" as used in this invention refers to a collective term for divalent groups formed by removing two hydrogen atoms from the nucleus carbon of an aromatic heterocycle composed of carbon and heteroatoms. Apart from being divalent groups, they are subject to the same description of heteroaryl groups as described above.

[0038] The alicyclic and aromatic ring fused groups described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and aromatic rings. Therefore, apart from being divalent groups, they are applicable to the above description of fused alicyclic and aromatic ring fused groups.

[0039] The fused alicyclic and heteroaromatic ring groups described in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and heteroaromatic rings. Therefore, apart from being divalent groups, they are applicable to the above description of fused alicyclic and heteroaromatic ring groups.

[0040] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" in the above-mentioned terms include, but are not limited to, the following groups: deuterium, tritium, cyano, nitro, hydroxyl, halogen atom, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl, substituted or unsubstituted C1-C15 alkoxy, substituted or unsubstituted C1-C15 alkylthio, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aromatic amino, etc. The substituents are preferably the following groups: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, trifluoromethyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The following are listed: benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9'-spirodifluorenyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, benzoquinolinyl, benzoisoquinolinyl, phenanthrolinel, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indoleyl, carbazoleyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted, and two adjacent substituents can be linked to form a ring.

[0041] This invention provides a triarylamine compound, which is represented by the structure shown in Formula 1:

[0042]

[0043] A is selected from Equation 2, B is selected from Equation 3, and C is selected from Equation 3;

[0044]

[0045] Y1 is selected from O or S; Y2 is selected from CH, O or S;

[0046] The "--" is selected from none or a single bond; when Y2 is selected from CH, the "--" is selected from a single bond; when Y2 is selected from O or S, the "--" is selected from none.

[0047] The R a R b R1, R2, R3, and R4 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl, and any combination thereof; or adjacent R1, R2, R3, and R4 can be interconnected to form substituted or unsubstituted rings;

[0048] The x values ​​are selected from N or CH, and the x values ​​at the bonding sites are selected from C.

[0049] a is selected from 0, 1, 2, or 3; b is selected from 0, 1, or 2; c is selected from 0, 1, 2, 3, 4, or 5; d is selected from 0, 1, 2, or 3; e is selected from 0, 1, 2, 3, or 4; when there are two or more R a R b When R1, R2, R3, R4, two or more R a R b R1, R2, R3, and R4 are either the same as or different from each other;

[0050] The L aSelected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, substituted or unsubstituted terphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, substituted or unsubstituted benzocyclopropyl, substituted or unsubstituted benzocyclobutylene, substituted or unsubstituted benzocyclopentylene, substituted or unsubstituted benzocyclohexylene The following are possible combinations of substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted benzocyclobutenyl, substituted or unsubstituted benzocyclopentenyl, substituted or unsubstituted benzocyclohexenyl, substituted or unsubstituted benzocycloheptenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, and combinations thereof.

[0051] The L b L c It is independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroarylene rings, and combinations thereof.

[0052] Preferably, Formula 2 is selected from any one of the following groups:

[0053]

[0054] a1 is selected from 0, 1, 2, or 3; a2 is selected from 0, 1, or 2; a3 is selected from 0 or 1; b is selected from 0, 1, or 2; when there are two or more R... a R b At that time, two or more R a R b They may be the same as or different from each other.

[0055] Preferably, the R a R bThe group independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzo[…]. The cyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzooxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof.

[0056] The R a R b The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0057] Preferably, R1, R2, R3, and R4 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, and benzofuran. The following are all groups of compounds: alkyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof; or adjacent R1, R2, R3, and R4 may be interconnected to form substituted or unsubstituted rings.

[0058] The substituents in R1, R2, R3, and R4 that are "substituted or unsubstituted" are selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0059] More preferably, Formula 3 is selected from any one of the following groups:

[0060]

[0061]

[0062] Preferably, the L a Selected from single bonds or one of the following groups:

[0063]

[0064] The R c The following groups, selected identically or differently from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and any combination thereof;

[0065] The R d The following groups, selected identically or differently from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof;

[0066] The g1 is selected from 0, 1, 2, 3, or 4; the g2 is selected from 0, 1, 2, or 3; the g3 is selected from 0, 1, or 2; the g4 is selected from 0, 1, 2, 3, 4, or 5; the g5 is selected from 0, 1, 2, 3, 4, 5, or 6; the g6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the g7 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the g8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R c R d At that time, two or more R c R d They may be the same as or different from each other.

[0067] The R c R d The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0068] More preferably, the L a Selected from single bonds or one of the following groups:

[0069]

[0070]

[0071]

[0072] Preferably, the L b L c Independently selected from a single bond or one of the following groups:

[0073]

[0074] The z may be the same or different from N or CH; the z at the bonding site is selected from C;

[0075] The R eThe same or different from any one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl, and combinations thereof; or the two adjacent R e They can connect with each other to form substituted or unsubstituted rings;

[0076] The ring G is selected from substituted or unsubstituted C3-C10 alicyclic groups;

[0077] The W is selected from O, S, N(R) g ) or C(R h R i );

[0078] The R g It is selected from any one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted silyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic groups, fused cycloalcoholic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C30 heteroaryl groups, and combinations thereof;

[0079] The R h R i Independently selected from any one of the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and combinations thereof. Or R h R i They can connect with each other to form substituted or unsubstituted rings;

[0080] h1 is selected from 0, 1, 2, 3, or 4; h2 is selected from 0, 1, 2, or 3; h3 is selected from 0, 1, or 2; when there are two or more R... e R f At that time, two or more R e R f They may be the same as or different from each other.

[0081] More preferably, the Lb L c Independently selected from a single bond or one of the following groups:

[0082]

[0083] The R e The following groups, selected identically or differently from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof; or two adjacent R groups. e They can connect with each other to form substituted or unsubstituted rings;

[0084] The R f The following groups, selected identically or differently from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazole, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof;

[0085] The R g Selected from one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, indole, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and any combination thereof;

[0086] The R h Ri Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or any of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, indole, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and any combination thereof; or R h R i They can connect with each other to form substituted or unsubstituted rings;

[0087] h1 is selected from 0, 1, 2, 3, or 4; h2 is selected from 0, 1, 2, or 3; h3 is selected from 0, 1, or 2; h4 is selected from 0, 1, 2, 3, 4, 5, or 6; h5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... e R f At that time, two or more R e R f They may be the same as or different from each other.

[0088] The R e R f R g R h R i The substituents in "substituted or unsubstituted" are selected from one or more of deuterium, tritium, halogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, and naphthyl. When two or more substituents are present, the two or more substituents are the same as or different from each other.

[0089] More preferably, the L b L c Independently selected from a single bond or one of the following groups:

[0090]

[0091]

[0092] Most preferably, the triarylamine compound is selected from any one of the following structures:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] The above lists some specific structural forms of the triarylamine compounds described in Formula 1 of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Formula 1 with substituents as defined above should be included.

[0108] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside at least one of the electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0109] The organic layer of the present invention includes a hole transport region, a light-emitting layer, an electron transport region, and a capping layer. The hole transport region includes functional layers such as a hole injection layer, a hole transport layer, and an electron blocking layer. The electron transport region includes functional layers such as a hole blocking layer, an electron transport layer, and an electron injection layer. The organic functional layers can be increased or decreased as needed.

[0110] The organic layer described in this invention can have a single-layer structure or a multi-layer structure. A single-layer structure includes a single layer containing a single material or a single layer containing multiple materials; a multi-layer structure includes multiple layers containing multiple materials. For example, the electron transport layer may also include a first electron transport layer and a second electron transport layer.

[0111] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region containing any one or a combination of at least two of the triarylamine compounds described in this invention.

[0112] Preferably, the hole transport region includes a hole transport layer, which contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0113] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. At least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0114] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the first hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0115] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the second hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0116] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer. The first hole transport layer is located between the anode and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. The third hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0117] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the anode and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the first hole transport layer and the second hole transport layer contain any one or a combination of at least two of the triarylamine compounds described in this invention.

[0118] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:

[0119] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate serves as the connection point between the organic electroluminescent device and the external circuit, and is preferably made of a material with good stability. Commonly used substrate materials include glass, resin, silicon, and metal foil, but are not limited to these.

[0120] The anode material described in this invention is preferably a material with good electrical conductivity and a high work function. It may include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ITO-Ag-ITO; conductive polymers, such as poly(3-methylthiophene), polypyrrole, polyaniline, and poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), but is not limited thereto.

[0121] The hole injection material described in this invention is preferably a material with good hole-accepting ability. Materials include metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide, phthalocyanine compounds, benzidine compounds, and phenazine compounds, such as copper phthalocyanine (CuPc), titanium phthalocyanine, N,N'-diphenyl-N,N'-di-[4-(N,N-diphenylamine)phenyl]benzidine (NPNPB), N,N,N',N'-tetra(4-methoxyphenyl)benzidine (MeO-TPD), diquinoxolino[2,3-a:2',3'-c]phenazine (HATNA), 4,4',4”-tris[2-naphthylphenylamino]triphenylamine (2T-NATA), 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzophenanthrene (HAT-CN), and 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), but are not limited to these.

[0122] The hole transport layer material described in this invention preferably has a high hole mobility. In addition to the triarylamine compounds described in this invention, it also includes diphenylamine compounds, triphenylamine compounds, fluorene compounds, and carbazole compounds, such as N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (α-NPD), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 4-[1-[4-[di(4-methylphenyl)amino]phenyl]cyclohexyl]-N-(3-methylphenyl)-N-(4-methylphenyl)aniline (TAPC), etc., but is not limited thereto.

[0123] The light-emitting layer material of this invention includes a host material and a doped material. The host material can be selected from anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, etc. Specific examples include 4,4'-bis(9-carbazole)biphenyl (CBP), 9,10-bis(2-naphthyl)anthracene (ADN), 4,4-bis(9-carbazole)biphenyl (CPB), 9,9'-(1,3-phenyl)bis-9H-carbazole (mCP), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 9, 10-Di(1-naphthyl)anthracene (α-ADN), N,N'-di-(1-naphthyl)-N,N'-diphenyl-[1,1':4',1”:4”,1”'-tetraphenyl]-4,4”'-diamino (4PNPB), 1,3,5-tris(9-carbazolyl)benzene (TCP), etc., but not limited to these; the doping material can be selected from fused polycyclic aromatic derivatives, styrylamine derivatives, fused ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, heavy metal complexes, phosphorescent rare earth metal complexes, etc. Specific examples include (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine)(DPAP-DPPA), 2,5,8,11-tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), bis(2-hydroxyphenylpyridine)beryllium (Bepp2), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboxyiridium (FIrpic), tri(2-phenyl) Iridium(Ir(ppy)3), bis(2-phenylpyridine)iridium(Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), tris[1-phenylisoquinoline-C2,N]iridium(III)(Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetone)iridium(Ir(piq)2(acac)), etc., but not limited to these.

[0124] The electron transport layer material described in this invention preferably has a high electron mobility, including quinolines, imidazoles, o-phenanthroline derivatives, triazoles, metal complexes, triazines, pyridines, etc. Quinolines include 8-hydroxyquinoline-lithium (LiQ), imidazoles include 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), o-phenanthroline derivatives include 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP) and 2-(naphthyl-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), and triazoles include 3-(biphenyl- Examples of triazine compounds include 4-(4-tert-butylphenyl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), metal complexes include tri(8-hydroxyquinoline)aluminum(III) (Alq3), triazines include 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), and pyridines include 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), but these are not limited to these.

[0125] The electron injection material described in this invention is preferably a material with good electron injection capability. It includes metal salts, metal oxides, and metals. Metal salts include lithium fluoride (LiF), lithium 8-hydroxyquinoline (Liq), sodium fluoride (NaF), rubidium fluoride (RbF), cesium fluoride (CsF), magnesium phosphide (MgP), and cesium carbonate (Cs₂CO₃), etc.; metal oxides include lithium oxide (Li₂O), lithium boron oxide (LiBO₂), aluminum oxide (Al₂O₃), and vanadium oxide (V₂O₅), etc.; and metals include lithium (Li) and cesium (Cs), etc., but are not limited to these.

[0126] The cathode material described in this invention is preferably a material with a low work function. This includes metals and metal alloys. Metals include aluminum (Al), silver (Ag), gold (Au), lead (Pb), lithium (Li), and magnesium (Mg), while metal alloys include magnesium-silver alloys (Mg / Al), lithium-aluminum alloys (Li / Al), and calcium / silver alloys (Ca / Ag), but are not limited to these.

[0127] The capping material described in this invention is preferably a material with excellent light extraction properties. It includes metal compounds, aromatic amine derivatives, carbazole derivatives, etc. Metal compounds include tris(8-hydroxyquinoline)aluminum(III) (Alq3), aromatic amine derivatives include N,N'-di(naphthyl-1-yl)-N,N'-di(phenyl)-2,2'-dimethylbenzidine (NPD), and carbazole derivatives include 4,4'-di(9-carbazole)biphenyl (CBP), but are not limited to these.

[0128] The present invention does not impose any special restrictions on the thickness of each organic layer of the organic electroluminescent device; thicknesses commonly used in the field can be adopted.

[0129] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, vapor deposition, spin coating, sputtering, spraying, screen printing, laser transfer, etc. can be used, but it is not limited to these methods.

[0130] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields, but is not limited thereto.

[0131] Synthesis Examples

[0132] There are no particular limitations on the preparation method of the triarylamine compounds represented by Formula 1 of this invention, and preparation methods well known to those skilled in the art can be used. For example, the following synthetic route can be used for preparation, but the invention is not limited thereto:

[0133]

[0134] The X a X b It is independently selected from any one of I, Br, and Cl.

[0135] Raw materials and reagents: The present invention does not impose any particular restrictions on the raw materials or reagents used in the following synthesis examples. They can be commercially available products or prepared using methods well known to those skilled in the art.

[0136] Instruments: The mass spectrometer is a G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer manufactured by Waters Instruments, UK; the elemental analyzer is a Vario EL cube organic elemental analyzer manufactured by Elementar, Germany.

[0137] [Synthetic Example 1] Synthesis of Compound 5

[0138]

[0139] Preparation of A-5:

[0140] Under nitrogen protection, a-5 (20.01 g, 60.00 mmol), b-5 (23.84 g, 60.00 mmol), palladium acetate (0.11 g, 0.48 mmol), tri-tert-butylphosphine (0.19 g, 0.96 mmol), sodium tert-butoxide (6.92 g, 72.00 mmol), and toluene (600 ml) were added to a reaction flask. The mixture was stirred under reflux for 5 hours, cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was recrystallized from ethyl acetate / petroleum ether (4:1) to give A-5 (32.36 g, 83%); HPLC purity ≥99.83%. Mass spectrometry m / z: 649.2786 (theoretical value: 649.2770).

[0141] Preparation of compound 5:

[0142] Under nitrogen protection, A-5 (19.50 g, 30.00 mmol), C-5 (5.91 g, 30.00 mmol), sodium tert-butoxide (3.46 g, 36.00 mmol), tris(dibenzylacetone) dipalladium (0.27 g, 0.30 mmol), tri-tert-butylphosphine (0.12 g, 0.60 mmol), and toluene (200 ml) were added to a reaction flask, and the mixture was reacted under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was recrystallized from toluene / ethanol (3:1) to give compound 5 (16.54 g, 72%); HPLC purity ≥99.96%. Mass spectrometry m / z: 765.3046 (theoretical value: 765.3032). Theoretical elemental content (%) C 58 H 39 NO: C, 90.95; H, 5.13; N, 1.83. Measured elemental content (%): C, 90.92; H, 5.16; N, 1.88.

[0143] [Synthetic Example 2] Synthesis of Compound 10

[0144]

[0145] According to the preparation method in Example 1, equimolar amounts of a-5 were replaced with equimolar amounts of a-10 to obtain compound 10 (16.77 g, yield 73%); HPLC purity ≥99.97%. Mass spectrometry m / z: 765.3023 (theoretical value: 765.3032). Theoretical elemental content (%) C 58 H 39 NO: C, 90.95; H, 5.13; N, 1.83. Measured elemental content (%): C, 90.92; H, 5.16; N, 1.85.

[0146] [Synthetic Example 3] Synthesis of Compound 13

[0147]

[0148] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5 and b-5 were replaced with equimolar amounts of a-10 and b-13, respectively, to obtain compound 13 (16.53 g, yield 71%); HPLC purity ≥99.95%. Mass spectrometry m / z: 775.3648 (theoretical value: 775.3659). Theoretical elemental content (%) C 58 H 29 D 10 NO: C, 89.77; H, 6.36; N, 1.80. Measured elemental content (%): C, 89.72; H, 6.33; N, 1.85.

[0149] [Synthetic Example 4] Synthesis of Compound 28

[0150]

[0151] According to the preparation method in Example 1, equimolar amounts of A-5 and c-5 were replaced with equimolar amounts of A-10 and c-28, respectively, to obtain compound 28 (16.54 g, yield 72%); HPLC purity ≥99.96%. Mass spectrometry m / z: 765.3046 (theoretical value: 765.3032). Theoretical elemental content (%) C 58 H 39 NO: C, 90.95; H, 5.13; N, 1.83. Measured elemental content (%): C, 90.91; H, 5.17; N, 1.86.

[0152] [Synthetic Example 5] Synthesis of Compound 35

[0153]

[0154] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-35, b-35, and c-35, respectively, to obtain compound 35 (16.77 g, yield 73%); HPLC purity ≥99.97%. Mass spectrometry m / z: 765.3048 (theoretical value: 765.3032). Theoretical elemental content (%) C 58 H 39 NO: C, 90.95; H, 5.13; N, 1.83. Measured elemental content (%): C, 90.97; H, 5.15; N, 1.80.

[0155] [Synthetic Example 6] Synthesis of Compound 60

[0156]

[0157] According to the preparation method in Synthesis Example 1, equimolar c-5 was replaced with equimolar c-60 to obtain compound 60 (17.18 g, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 841.3356 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.26; H, 5.13; N, 1.68.

[0158] [Synthetic Example 7] Synthesis of Compound 64

[0159]

[0160] According to the preparation method in Example 1, equimolar amounts of A-5 and c-5 were replaced with equimolar amounts of A-10 and c-60, respectively, to obtain compound 64 (17.43 g, yield 69%); HPLC purity ≥99.95%. Mass spectrometry m / z: 841.3335 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.32; H, 5.18; N, 1.61.

[0161] [Synthetic Example 8] Synthesis of Compound 65

[0162]

[0163] Preparation of C-65:

[0164] Under nitrogen protection, d-65 (11.34 g, 70.00 mmol), e-65 (16.21 g, 70.00 mmol), tetraphenylphosphine palladium (0.81 g, 0.70 mmol), potassium carbonate (14.51 g, 105.00 mmol), tetrahydrofuran (250 ml), and water (100 ml) were added to a reaction flask, and the mixture was stirred under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was removed under reduced pressure, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene:n-hexane = 4:1 to give c-65 (15.99 g, 85%). The purity of the solid was ≥99.75% as determined by HPLC. Mass spectrometry m / z: 268.0669 (theoretical value: 268.0655).

[0165] Preparation of A-10:

[0166] Under nitrogen protection, a-10 (20.01 g, 60.00 mmol), b-5 (23.84 g, 60.00 mmol), palladium acetate (0.11 g, 0.48 mmol), tri-tert-butylphosphine (0.19 g, 0.96 mmol), sodium tert-butoxide (6.92 g, 72.00 mmol), and toluene (600 ml) were added to a reaction flask. The mixture was stirred under reflux for 6 hours, cooled to room temperature, and water was added. The mixture was extracted with ethyl acetate, and the organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was recrystallized from ethyl acetate / petroleum ether (4:1) to give A-10 (31.97 g, 82%); HPLC purity ≥99.86%. Mass spectrometry m / z: 649.2755 (theoretical value: 649.2770).

[0167] Preparation of compound 65:

[0168] Under nitrogen protection, A-10 (19.50 g, 30.00 mmol), C-65 (8.06 g, 30.00 mmol), sodium tert-butoxide (3.46 g, 36.00 mmol), tris(dibenzylacetone) dipalladium (0.27 g, 0.30 mmol), tri-tert-butylphosphine (0.12 g, 0.60 mmol), and toluene (200 ml) were added to a reaction flask, and the mixture was reacted under reflux for 8 hours. After the reaction was complete, the mixture was cooled to room temperature, water was added, the organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The crude product was recrystallized from toluene / ethanol (3:1) to give compound 65 (17.73 g, yield 67%); HPLC purity ≥99.93%. Mass spectrometry m / z: 881.3669 (theoretical value: 881.3658). Theoretical elemental content (%) C 67 H 47 NO: C, 91.23; H, 5.37; N, 1.59. Measured elemental content (%): C, 91.27; H, 5.40; N, 1.56.

[0169] [Synthetic Example 9] Synthesis of Compound 66

[0170]

[0171] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65, b-5, and c-65 were replaced with equimolar amounts of e-66, b-66, and c-66, respectively, to obtain compound 66 (17.26, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 845.3583 (theoretical value: 845.3596). Theoretical elemental content (%) C 64 H 39D4NO: C, 90.85; H, 5.60; N, 1.66. Measured elemental content (%): C, 90.82; H, 5.64; N, 1.61.

[0172] [Synthetic Example 10] Synthesis of Compound 67

[0173]

[0174] According to the preparation method in Synthesis Example 1, equimolar amounts of A-5 and c-5 were replaced with equimolar amounts of A-10 and c-67, respectively, to obtain compound 67 (17.43 g, yield 69%); HPLC purity ≥99.95%. Mass spectrometry m / z: 841.3354 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.25; H, 5.12; N, 1.68.

[0175] [Synthetic Example 11] Synthesis of Compound 98

[0176]

[0177] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65, A-10, and c-65 were replaced with equimolar amounts of e-98, A-5, and c-98, respectively, to obtain compound 98 (17.93 g, yield 67%); HPLC purity ≥99.93%. Mass spectrometry m / z: 891.3516 (theoretical value: 891.3501). Theoretical elemental content (%) C 68 H 45 NO: C, 91.55; H, 5.08; N, 1.57. Measured elemental content (%): C, 91.53; H, 5.11; N, 1.52.

[0178] [Synthetic Example 12] Synthesis of Compound 103

[0179]

[0180] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65 and c-65 were replaced with equimolar amounts of e-103 and c-103, respectively, to obtain compound 103 (17.20 g, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 842.3281 (theoretical value: 842.3297). Theoretical elemental content (%) C 63 H 42N₂O: C, 89.76; H, 5.02; N, 3.32. Measured elemental content (%): C, 89.74; H, 5.06; N, 3.35.

[0181] [Synthetic Example 13] Synthesis of Compound 108

[0182]

[0183] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65 and c-65 were replaced with equimolar amounts of e-108 and c-108, respectively, to obtain compound 108 (18.37 g, yield 65%); HPLC purity ≥99.92%. Mass spectrometry m / z: 941.3669 (theoretical value: 941.3658). Theoretical elemental content (%) C 72 H 47 NO: C, 91.79; H, 5.03; N, 1.49. Measured elemental content (%): C, 91.75; H, 5.05; N, 1.46.

[0184] [Synthetic Example 14] Synthesis of Compound 112

[0185]

[0186] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65 and c-65 were replaced with equimolar amounts of e-112 and c-112, respectively, to obtain compound 112 (18.40 g, yield 64%); HPLC purity ≥99.91%. Mass spectrometry m / z: 957.3983 (theoretical value: 957.3971). Theoretical elemental content (%) C 73 H 51 NO: C, 91.50; H, 5.36; N, 1.46. Measured elemental content (%): C, 91.54; H, 5.34; N, 1.48.

[0187] [Synthetic Example 15] Synthesis of Compound 116

[0188]

[0189] According to the preparation method in Synthesis Example 8, equimolar amounts of e-65 and c-65 were replaced with equimolar amounts of e-116 and c-116, respectively, to obtain compound 116 (18.46 g, yield 66%); HPLC purity ≥99.93%. Mass spectrometry m / z: 931.3442 (theoretical value: 931.3450). Theoretical elemental content (%) C 70 H 45NO2: C, 90.20; H, 4.87; N, 1.50. Measured elemental content (%): C, 90.25; H, 4.85; N, 1.48.

[0190] [Synthetic Example 16] Synthesis of Compound 123

[0191]

[0192] According to the preparation method in Synthesis Example 1, equimolar amounts of b-5 were replaced with equimolar amounts of b-123 to obtain compound 123 (17.18 g, yield 68%); HPLC purity ≥99.95%. Mass spectrometry m / z: 841.3359 (theoretical value: 841.3345). Theoretical elemental content (%) C 64 H 43 NO: C, 91.29; H, 5.15; N, 1.66. Measured elemental content (%): C, 91.32; H, 5.17; N, 1.64.

[0193] [Synthetic Example 17] Synthesis of Compound 125

[0194]

[0195] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-10, b-125, and c-60, respectively, to obtain compound 125 (18.28 g, yield 66%); HPLC purity ≥99.93%. Mass spectrometry m / z: 922.3984 (theoretical value: 922.3971). Theoretical elemental content (%) C 70 H 42 D5NO: C, 91.07; H, 5.68; N, 1.52. Measured elemental content (%): C, 91.05; H, 5.64; N, 1.55.

[0196] [Synthetic Example 18] Synthesis of Compound 142

[0197]

[0198] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-142, b-123, and c-60, respectively, to obtain compound 142 (19.09 g, yield 64%); HPLC purity ≥99.91%. Mass spectrometry m / z: 993.3960 (theoretical value: 993.3971). Theoretical elemental content (%) C 76 H 51NO: C, 91.81; H, 5.17; N, 1.41. Measured elemental content (%): C, 91.85; H, 5.12; N, 1.43.

[0199] [Synthetic Example 19] Synthesis of Compound 160

[0200]

[0201] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-10, b-160, and c-160, respectively, to obtain compound 160 (17.35 g, yield 69%); HPLC purity ≥99.95%. Mass spectrometry m / z: 837.3413 (theoretical value: 837.3429). Theoretical elemental content (%) C 62 H 47 NS: C, 88.85; H, 5.65; N, 1.67. Measured elemental content (%): C, 88.81; H, 5.67; N, 1.64.

[0202] [Synthetic Example 20] Synthesis of Compound 176

[0203]

[0204] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-10, b-176, and c-176, respectively, to obtain compound 176 (17.43 g, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 853.3185 (theoretical value: 853.3198). Theoretical elemental content (%) C 61 H 47 NSSi: C, 85.77; H, 5.55; N, 1.64. Measured elemental content (%): C, 85.75; H, 5.58; N, 1.67.

[0205] [Synthetic Example 21] Synthesis of Compound 196

[0206]

[0207] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-10, b-196, and c-196, respectively, to obtain compound 196 (18.14 g, yield 66%); HPLC purity ≥99.93%. Mass spectrometry m / z: 915.3885 (theoretical value: 915.3899). Theoretical elemental content (%) C 68 H 53NS: C, 89.14; H, 5.83; N, 1.53. Measured elemental content (%): C, 89.12; H, 5.86; N, 1.57.

[0208] [Synthetic Example 22] Synthesis of Compound 205

[0209]

[0210] According to the preparation method in Synthesis Example 1, equimolar c-5 was replaced with equimolar c-205 to obtain compound 205 (17.76 g, yield 69%); HPLC purity ≥99.95%. Mass spectrometry m / z: 857.3131 (theoretical value: 857.3116). Theoretical elemental content (%) C 64 H 43 NS: C, 89.58; H, 5.05; N, 1.63. Measured elemental content (%): C, 89.54; H, 5.07; N, 1.66.

[0211] [Synthetic Example 23] Synthesis of Compound 251

[0212]

[0213] According to the preparation method in Synthesis Example 1, equimolar amounts of a-5, b-5, and c-5 were replaced with equimolar amounts of a-10, b-251, and c-160, respectively, to obtain compound 251 (17.51 ​​g, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 857.3105 (theoretical value: 857.3116). Theoretical elemental content (%) C 64 H 43 NS: C, 89.58; H, 5.05; N, 1.63. Measured elemental content (%): C, 89.56; H, 5.09; N, 1.60.

[0214] [Synthetic Example 24] Synthesis of Compound 263

[0215]

[0216] According to the preparation method in Synthesis Example 1, equimolar c-5 was replaced with equimolar c-263 to obtain compound 263 (18.50 g, yield 66%); HPLC purity ≥99.92%. Mass spectrometry m / z: 933.3415 (theoretical value: 933.3429). Theoretical elemental content (%) C 70 H 47 NS: C, 90.00; H, 5.07; N, 1.50. Measured elemental content (%): C, 90.03; H, 5.05; N, 1.53.

[0217] [Synthetic Example 25] Synthesis of Compound 421

[0218]

[0219] According to the preparation method in Example 1, equimolar amounts of c-5 were replaced with equimolar amounts of c-421 to obtain compound 421 (17.91 g, yield 68%); HPLC purity ≥99.94%. Mass spectrometry m / z: 877.2821 (theoretical value: 877.2837). Theoretical elemental content (%) C 63 H 43 NS2: C, 86.17; H, 4.94; N, 1.60. Measured elemental content (%): C, 86.13; H, 4.97; N, 1.62.

[0220] [Synthetic Example 26] Synthesis of Compound 429

[0221]

[0222] According to the preparation method in Example 1, equimolar amounts of a-5 and c-5 were replaced with equimolar amounts of a-429 and c-429, respectively, to obtain compound 429 (16.74 g, yield 71%); HPLC purity ≥99.96%. Mass spectrometry m / z: 785.2764 (theoretical value: 785.2752). Theoretical elemental content (%) C 57 H 39 NOS: C, 87.10; H, 5.00; N, 1.78. Measured elemental content (%): C, 87.14; H, 5.02; N, 1.74.

[0223] [Synthetic Example 27] Synthesis of Compound 442

[0224]

[0225] According to the preparation method in Synthesis Example 1, equimolar amounts of A-5 and c-5 were replaced with equimolar amounts of A-10 and c-442, respectively, to obtain compound 442 (18.53 g, yield 73%); HPLC purity ≥99.97%. Mass spectrometry m / z: 845.3283 (theoretical value: 845.3294). Theoretical elemental content (%) C 63 H 43 NO2: C, 89.44; H, 5.12; N, 1.66. Measured elemental content (%): C, 89.45; H, 5.15; N, 1.65.

[0226] [Comparative Example 1] Device Fabrication Example: (First Hole Transport Layer)

[0227] Comparative Example 1: First, the glass substrate coated with ITO / Ag / ITO was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. After drying on a hot plate heated to 120°C, it was transferred to a plasma cleaner and cleaned for 5 minutes before being transferred to a vapor deposition machine.

[0228] On a cleaned ITO / Ag / ITO substrate, HI-1 is deposited as a hole injection layer with a thickness of 15 nm. Ref-1 is then deposited on this hole injection layer as a first hole transport layer with a thickness of 25 nm. HT2 is then deposited on this first hole transport layer as a second hole transport layer with a thickness of 30 nm. Next, a mixture of BH-1 and BD-1 (mass ratio 95:5) is vacuum-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 35 nm. Finally, a layer is deposited on the light-emitting layer... An organic electroluminescent device was fabricated by depositing ET-1 and Liq (mass ratio 1:1) as an electron transport layer with a thickness of 30 nm. LiF was then deposited on this electron transport layer as an electron injection layer with a thickness of 1 nm. Mg:Ag (mass ratio 1:9) was then deposited on this electron injection layer as a cathode with a thickness of 15 nm. Finally, CP-1 was vacuum-deposited on the cathode as a capping layer with a thickness of 55 nm, thereby fabricating an organic electroluminescent device (the material structures of each functional layer in the fabrication process of the organic electroluminescent device are as follows).

[0229]

[0230] [Examples 1-20]

[0231] The first hole transport layer material of the organic electroluminescent device is sequentially replaced with compounds 5, 10, 13, 28, 60, 64, 65, 66, 98, 108, 112, 123, 125, 142, 160, 176, 205, 251, 421, and 442 of the present invention, and the other steps are the same as in Comparative Example 1.

[0232] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, and the temperature was room temperature. Table 1 below shows the luminous characteristic test results of the OLEDs obtained in Comparative Device Example 1 and Device Examples 1-20.

[0233] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0234]

[0235] As shown in Table 1, compared with Comparative Example 1, when the triarylamine compounds described in this invention are used as the first hole transport layer material in organic electroluminescent devices, the luminous efficiency and lifespan of the devices are both better.

[0236] [Comparative Example 2] Device Fabrication Example: (Second Hole Transport Layer)

[0237] Comparative Example 2: First, the glass substrate coated with ITO / Ag / ITO was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then, it was dried on a hot plate heated to 120°C. After drying, it was transferred to a plasma cleaner and cleaned for 5 minutes. Then, the substrate was transferred to the vapor deposition machine.

[0238] On a cleaned ITO / Ag / ITO substrate, HI-1 is deposited as a hole injection layer with a thickness of 10 nm. HT1 is then deposited on this hole injection layer as a first hole transport layer with a thickness of 30 nm. Ref-2 is then deposited on this first hole transport layer as a second hole transport layer with a thickness of 35 nm. Finally, a mixture of RH-1, RH-2, and RD-1 (mass ratio 49:49:2) is vacuum-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 30 nm. An electron transport layer consisting of ET-1 and Liq (mass ratio 1:1) with a thickness of 35 nm is deposited on the light-emitting layer. LiF is then deposited on this electron transport layer as an electron injection layer with a thickness of 1 nm. Mg:Ag (mass ratio 1:9) is then deposited on this electron injection layer as a cathode with a thickness of 12 nm. Finally, CP-1 is vacuum-deposited on the cathode as a capping layer with a thickness of 65 nm, thus fabricating an organic electroluminescent device (the material structures of each functional layer during the fabrication of the organic electroluminescent device are as follows).

[0239]

[0240] [Examples 21-40]

[0241] The second hole transport layer material of the organic electroluminescent device was sequentially replaced with compounds 10, 13, 28, 35, 64, 65, 66, 67, 98, 103, 112, 116, 125, 160, 176, 196, 205, 251, 263, and 429 of this invention, with other steps being the same as in Comparative Example 2. The luminescent characteristics test results of the organic electroluminescent devices obtained in Comparative Device Example 2 and Device Examples 21-40 of this invention are shown in Table 2 below.

[0242] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0243]

[0244]

[0245] As shown in Table 2, compared with Comparative Example 2, using the triarylamine compounds described in this invention as the second hole transport layer material in organic electroluminescent devices can improve the luminous efficiency of the devices and extend their service life.

[0246] [Comparative Example 3] Device Fabrication Example: (Third Hole Transport Layer)

[0247] Comparative Example 3: First, the glass substrate coated with ITO / Ag / ITO was washed twice with distilled water and ultrasonically cleaned for 30 minutes. Then, it was washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then, it was dried on a hot plate heated to 120°C. After drying, it was transferred to a plasma cleaner and cleaned for 5 minutes. Then, the substrate was transferred to the vapor deposition machine.

[0248] On a cleaned ITO / Ag / ITO substrate, HI-1 is deposited as a hole injection layer with a thickness of 10 nm. HT1 is then deposited as a first hole transport layer with a thickness of 25 nm on this hole injection layer. HT2 is then deposited as a second hole transport layer with a thickness of 25 nm on the first hole transport layer. Ref-3 is then deposited as a third hole transport layer with a thickness of 20 nm on the second hole transport layer. Finally, a mixture of GH-1, GH-2, and GD-1 (mass ratio 47:47:6) is vacuum-deposited onto the third hole transport layer. An emitting layer with a thickness of 40 nm is formed by evaporation. Then, ET-1 and Liq (mass ratio 1:1) are deposited on the emitting layer as an electron transport layer with a thickness of 30 nm. LiF is then deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Mg:Ag (mass ratio 1:9) is then deposited on the electron injection layer as a cathode with a thickness of 15 nm. Finally, CP-1 is vacuum-deposited on the cathode as a capping layer with a thickness of 60 nm, thereby fabricating an organic electroluminescent device (the material structures of each functional layer in the fabrication process of the organic electroluminescent device are as follows).

[0249]

[0250]

[0251] [Examples 41-50]

[0252] The third hole transport layer material of the organic electroluminescent device was sequentially replaced with compounds 13, 35, 66, 67, 103, 116, 125, 196, 263, and 429 of this invention, with other steps being the same as in Comparative Example 3. The luminescence characteristics test results of the organic electroluminescent devices obtained in Comparative Device Example 3 and Device Examples 41-50 of this invention are shown in Table 3 below.

[0253] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0254]

[0255] As shown in Table 3, compared with Comparative Example 3, using the triarylamine compounds described in this invention as the third hole transport layer material in organic electroluminescent devices can significantly improve the efficiency and lifespan of organic electroluminescent devices.

[0256] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.

Claims

1. A triarylamine compound, characterized in that, The triarylamine compounds are represented by the structure shown in Formula 1: A is selected from Equation 2, B is selected from Equation 3, and C is selected from Equation 3; Formula 2 is selected from any one of the following groups: a1 is selected from 0, 1, 2, or 3; b is selected from 0, 1, or 2; when there are two or more R... a R b At that time, two or more R a R b They are the same as or different from each other; The R a R b Independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups and combinations thereof; R1, R2, R3, and R4 are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C6 alkyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted phenyl groups, and combinations thereof; or adjacent R1 groups or R2 groups are interconnected to form substituted or unsubstituted benzene rings; the substituted or unsubstituted silyl groups are selected from -Si(R m )3, R m It is selected from one of the following groups, either identically or differently: substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl; The x is CH; the x at the bonding site is C; c is selected from 0, 1, 2, 3, 4 or 5; d is selected from 0, 1, 2 or 3; e is selected from 0, 1, 2, 3 or 4; when there are two or more R1, R2, R3, R4, the two or more R1, R2, R3, R4 are the same as or different from each other; The L a Selected from single bonds or one of the following groups: The R c The same or different from any of the following groups selected from hydrogen, deuterium, tritium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; The R d The same or different from any of the following groups selected from hydrogen, deuterium, tritium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; The g1 is selected from 0, 1, 2, 3, or 4; the g2 is selected from 0, 1, 2, or 3; the g3 is selected from 0, 1, or 2; the g5 is selected from 0, 1, 2, 3, 4, 5, or 6; the g6 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R... c R d At that time, two or more R c R d They are the same as or different from each other; The L b L c Independently selected from a single bond or one of the following groups: The R e The same or different from any of the following groups selected from hydrogen, deuterium, tritium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; h1 is selected from 0, 1, 2, 3 or 4; when there are two or more R e At that time, two or more R e They are the same as or different from each other; The substituents represented by "substituted or unsubstituted" are selected from the following groups: deuterium, tritium, methyl, ethyl, propyl, and butyl.

2. The triarylamine compound according to claim 1, characterized in that, The R a R b The group is independently selected from hydrogen, deuterium, tritium, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof.

3. The triarylamine compound according to claim 1, characterized in that, Formula 3 is selected from any one of the following groups: 。 4. The triarylamine compound according to claim 1, characterized in that, The L a Selected from single bonds or one of the following groups: The R c Selected from hydrogen, deuterium, tritium, and combinations thereof, either identically or differently.

5. The triarylamine compound according to claim 1, characterized in that, The L b L c It is selected independently from a single bond.

6. A triarylamine compound, characterized in that, The triarylamine compound is selected from one of the following structures: 。 7. An organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside at least one of the electrodes of the anode and the cathode, characterized in that, The organic layer contains any one or a combination of at least two of the triarylamine compounds as described in any one of claims 1 to 6.

8. An organic electroluminescent device according to claim 7, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer includes a hole transport layer containing any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 6.

Images