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, and when the triarylamine compound is applied to a hole transport region in an organic electroluminescent device, the energy barrier in the hole injection process can be reduced, the hole transport rate can be improved, the hole transport rate and the electron transport rate can be balanced, the maximum recombination of carriers can be realized, and the luminous efficiency and service life of the device can be improved.In addition, the triarylamine compound has high refractive index, and when the triarylamine compound is applied to a cover layer in the device, the total reflection loss and waveguide loss in the device can be effectively reduced, the light trapped in the device can be coupled out, and the light extraction efficiency of the device can be improved.The triarylamine compound can be applied to many fields such as display, lighting, business, medicine and transportation.

Description

[0001] This application is a divisional application of the invention patent application filed on September 6, 2023, with application number 202311146290.6 and invention title "A triarylamine compound and its organic electroluminescent device". Technical Field

[0002] This invention relates to the field of organic electroluminescent materials technology, specifically to a triarylamine compound and its organic electroluminescent device. Background Technology

[0003] Organic light-emitting diodes (OLEDs) have gradually become a research focus in related industries both domestically and internationally due to their advantages such as high efficiency, high brightness, low driving voltage, good flexibility, wide viewing angle, high resolution, fast response speed, and wide range of material selection. Their applications in many fields such as display and lighting are becoming increasingly widespread, making them the most promising new display technology at present.

[0004] Organic electroluminescent devices (OLEDs) are devices that emit light when excited by an electric current or electric field. OLEDs consist of an anode, a cathode, and an organic layer. With the optimization of device structures, the types of materials are constantly increasing. Currently, the organic layer can include numerous functional layers such as hole injection layers, hole transport layers, electron blocking layers, light-emitting layers, and capping layers. These organic functional layers play a crucial role in improving the photoelectric performance of the device, enabling it to emit light efficiently and stably.

[0005] Hole transport materials are crucial for organic light-emitting diodes (OLEDs). Their role is to increase the hole transport rate within the device, balancing it with the electron transport rate, thereby increasing the recombination probability of excitons in the light-emitting layer and maximizing carrier recombination. However, most current hole transport materials suffer from low hole mobility, poor film-forming properties, and poor thermal stability. High-performance hole transport materials should possess high hole mobility, good thermal stability, and excellent film-forming properties, enabling them to lower the energy barrier during hole injection, improve hole injection efficiency, and ultimately enhance device efficiency, lifetime, and brightness.

[0006] To further improve the luminous efficiency of OLEDs, a capping layer with a higher refractive index is proposed to be placed on the outside of a semi-transparent electrode with a low refractive index. The application of the capping layer can reduce total internal reflection loss and waveguide loss in the device, couple out light trapped in the device, enhance light extraction efficiency, and thus improve the luminous efficiency of the device. However, there is currently limited research on capping layer materials both domestically and internationally.

[0007] Therefore, it is urgent to design high-performance materials to improve the luminous efficiency and extend the lifespan of devices, thereby comprehensively enhancing the performance of organic electroluminescent devices. Summary of the Invention

[0008] To address the aforementioned problems in the prior art, this invention provides a triarylamine compound and its organic electroluminescent device. When applied to the hole transport region or capping layer of an organic electroluminescent device, it can effectively improve the luminous efficiency and extend the device's lifespan. Specifically, the technical solution of this invention is as follows: This invention provides a triarylamine compound, which is represented by the structure shown in Formula I:

[0009] The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. The L is selected from any one of the following groups:

[0010] The x may be the same or different from CH or N; Y1 is selected from one of O, S, C(R2R3), and N(R4); The Y2 is selected from one of the following: single bond, O, S, C (R7R8), and N (R9); The R1s are selected from one of the following groups, either identically or differently: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic group, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or two adjacent R1s may be interconnected to form substituted or unsubstituted rings. R2, R3, R7, and R8 are independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or R2 and R3 can be interconnected to form substituted or unsubstituted rings. R4 and R9 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1 or 2; when there are two or more R1s, the two or more R1s are the same as or different from each other; The L1, L2, L3, L4, L5, L6, L a L b L c It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C15 alicyclic and a C6-C30 aromatic ring fused cycloalgide. The condition is that Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, L5, L6, L a L b L c At least one of them contains one or more groups represented by Formula II:

[0011] The R a R b R c It is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl.

[0012] 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 one or more 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.

[0013] Beneficial effects

[0014] This invention provides a triarylamine compound and its organic electroluminescent device. The triarylamine compound of this invention possesses high hole mobility, good thermal stability, and good film-forming properties. When applied to the hole transport region in an organic electroluminescent device, it can reduce the energy barrier during hole injection, increase the hole transport rate in the device, balance the hole transport rate with the electron transport rate, increase the recombination probability of excitons in the light-emitting layer, and achieve maximum carrier recombination, thereby improving the luminous efficiency and extending the device's lifespan. Furthermore, the triarylamine compound of this invention also has a high refractive index. When applied to the capping layer in an organic electroluminescent device, it can effectively reduce total internal reflection loss and waveguide loss, couple out trapped light, enhance light extraction efficiency, and further improve the luminous efficiency of the device. Detailed Implementation

[0015] 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.

[0016] 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.

[0017] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.

[0018] In this specification, " "This refers to the portion that is connected to another substituent." "It can be attached to any optional position of the attached group / fragment."

[0019] 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 or ; Can represent , , And so on.

[0020] 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.

[0021] In this specification, "at least one" includes, where permitted, one, two, three, four, five, six, seven, eight or more; In this specification, "one or more" includes, where permitted, one, two, three, four, five, six or more.

[0022] 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, and the resulting 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. Specific examples 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.

[0023]

[0024] 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, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, 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, substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C1-C12 alkylthio, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C30 aromatic amino, etc. Preferred compounds include: deuterium, tritium, cyano, fluorine, chlorine, bromine, iodine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutenyl, cyclopentenyl, cyclohexenyl, adamantyl, norbornyl, trifluoromethyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, phenylenetriene, anthracene, pyrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzo[] Cyclohexyl, benzocycloheptyl, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, phenanthrolineyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, indolyl, carbazoleyl, etc., but not limited to these. The above substituents can be further replaced by deuterium, alkyl, alicyclic, alicyclic, aryl, fused cyclic groups of alicyclic and aromatic rings, fused cyclic groups of alicyclic and aromatic rings, etc. In the case of multiple substituents, the multiple substituents may be the same as or different from each other.

[0025] 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.

[0026] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained 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.

[0027] 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 12 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.

[0028] 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.

[0029] The fused alicyclic and aromatic ring groups mentioned in this invention refer to the general term for monovalent groups obtained 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 12 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 6 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0030] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for the monovalent group obtained by removing one hydrogen atom after alicyclic and heteroaromatic rings are fused together. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 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.

[0031] The arylene groups referred to in this invention are a general term for divalent groups obtained by removing two hydrogen atoms from an aromatic carbon atom. Apart from being divalent groups, they are subject to the same description of aryl groups as described above.

[0032] The term "hybrid aryl" as used in this invention refers to the general term for divalent groups obtained 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.

[0033] The alicyclic and aromatic ring fused cyclic groups described in this invention refer to the general term for the divalent groups obtained by removing two hydrogen atoms after alicyclic and aromatic rings are fused together. Therefore, apart from being divalent groups, they are applicable to the above description of alicyclic and aromatic ring fused cyclic groups.

[0034] This invention provides a triarylamine compound, which is represented by the structure shown in Formula I:

[0035] The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. The L is selected from any one of the following groups:

[0036] The x may be the same or different from CH or N; Y1 is selected from one of O, S, C(R2R3), and N(R4); The Y2 is selected from one of the following: single bond, O, S, C (R7R8), and N (R9); The R1s are selected from one of the following groups, either identically or differently: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic group, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or two adjacent R1s may be interconnected to form substituted or unsubstituted rings. R2, R3, R7, and R8 are independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or R2 and R3 can be interconnected to form substituted or unsubstituted rings. R4 and R9 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1 or 2; when there are two or more R1s, the two or more R1s are the same as or different from each other; The L1, L2, L3, L4, L5, L6, L a L b L c It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C15 alicyclic and a C6-C30 aromatic ring fused cycloalgide. The condition is that Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, L5, L6, L a L b L c At least one of them contains one or more groups represented by Formula II:

[0037] The R a R b R c It is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl.

[0038] Preferably, the L is selected from any one of the following groups:

[0039] R1 is selected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, furanyl, benzofuranyl The following groups are included: uranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, acridineyl, o-phenanthrolineyl, and groups shown in Formula II; or two adjacent R1 groups may be interconnected to form substituted or unsubstituted benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, pyridyl rings, pyrimidinyl rings, quinolinyl rings, isoquinolinyl rings, quinazolinyl rings, quinoxalinyl rings, or C3-C8 aliphatic rings; R2, R3, R7, and R8 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the group shown in Formula II; or any one of R2 and R3 can be directly reacted with L. a L b L c Any one of the bonds in; R4 and R9 are independently 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, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or R4 can be directly substituted with L a L b L c Any one of the bonds in; a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1 or 2; a4 is selected from 0 or 1; when there are two or more R1s, the two or more R1s are the same as or different from each other.

[0040] The substituents in R1, R2, R3, R4, R7, R8, and R9 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.

[0041] More preferably, the L is selected from any one of the following groups:

[0042] The R1s are selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, or groups represented by Formula II; or two adjacent R1s may be connected to each other to form substituted or unsubstituted benzene rings, naphthyl rings, pyridine rings, pyrimidine rings, or C3-C8 aliphatic rings; R2 and R3 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, and groups represented by Formula II; R4 is 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, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene; or R4 can be directly reacted with La, L b L c Any one of the bonds in.

[0043] Preferably, the R a R b R c The group is independently selected from hydrogen, deuterium, tritium, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, ethylene, propylene, butene, pentene, hexeheptene, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazoyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; The R a R b R cThe 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.

[0044] Preferably, Formula II is selected from any one of the following groups: .

[0045] Preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following groups:

[0046] The y may be selected from N or CH, either the same or different. The ring A is selected from substituted or unsubstituted C3 to C10 aliphatic rings; Y3 and Y4 are independently selected from single bonds, O, S, and N(R). d ), C(R e R f One of them; The Y5 is selected from O, S, N(R) g ), C(R h R i One of the following; the Y6 is selected from N or CH; The R5 groups are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, pyrene, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or two adjacent R5 groups may be connected to each other to form substituted or unsubstituted rings; The Rd R g Selected, either identically or differently, 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, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or the group shown in Formula II; or the R group. d R g It can directly bond with any one of L1, L2, L3, L4, L5, and L6; The R e R f R h R i Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or the group shown in Formula II; or R e R f They can connect to each other to form substituted or unsubstituted rings; or R e R f Any one of them can be directly bonded to any one of L1, L2, L3, L4, L5, and L6; The b1 is selected from 0, 1, 2, 3, 4 or 5; the b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the b4 is selected from 0, 1, 2, 3 or 4; the b5 is selected from 0, 1, 2 or 3; when there are two or more R5s, the two or more R5s are the same as or different from each other.

[0047] More preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following groups:

[0048] The R5s are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and substituted or unsubstituted groups of the following: 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, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, and groups shown in Formula II; or two adjacent R5s may be interconnected to form substituted or unsubstituted benzene rings, naphthyl rings, pyridyl rings, pyrimidinyl rings, or C3-C8 aliphatic rings; The R d R g Selected, either identically or differently, from one of the following groups, substituted or unsubstituted: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl; or selected, substituted or unsubstituted, from one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclobutyl, benzocyclopentyl, benzocyclohexyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, or the group shown in Formula II. The R e R f R h R iThe group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiopheneyl, dibenzothiopheneyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, and the group shown in Formula II; The R m The same or different from one of the following groups: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorene; The b1 is selected from 0, 1, 2, 3, 4, or 5; the b2 is selected from 0, 1, 2, 3, 4, 5, 6, or 7; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; the b4 is selected from 0, 1, 2, 3, or 4; the b5 is selected from 0, 1, 2, or 3; the b6 is selected from 0, 1, or 2; the b7 is selected from 0, 1, 2, 3, 4, 5, or 6; the b8 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8; the b9 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the b 10 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when there are two or more R5s, the two or more R5s are the same as or different from each other; The R5, R d R e R f R g R h R i R m 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.

[0049] More preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following groups: .

[0050] More preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following groups:

[0051] The remainder are independently selected from one of the following groups: .

[0052] Preferably, L1, L2, L3, L4, L5, L6, L a L b L c Independently selected from a single bond or one of the following groups:

[0053] The z may be selected from N or CH, either the same or different. The ring B is selected from substituted or unsubstituted C3 to C10 aliphatic rings; E is selected from O, S, N(R) j ), C(R k R l One of them; The R6 groups are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or two adjacent R6 groups may be linked together to form substituted or unsubstituted rings; The R jSelected 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, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; or R j It can be directly bonded to any one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6; The R k R l Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazole, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, or the group shown in Formula II; or R k R l They can connect to each other to form substituted or unsubstituted rings; or R k R l Any one of them can be directly bonded to any one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6; c1 is selected from 0, 1, 2, 3 or 4; c2 is selected from 0, 1, 2 or 3; c3 is selected from 0, 1 or 2; when there are two or more R6, the two or more R6 are the same or different from each other.

[0054] More preferably, L1, L2, L3, L4, L5, L6, L a L b L c Independently selected from a single bond or one of the following groups:

[0055] The R6 may be the same as or different from one of the following groups: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, carbazoleyl, or the group shown in Formula II; or two adjacent R6 may be connected to each other to form a substituted or unsubstituted benzene ring, naphthyl ring, pyridine ring, pyrimidine ring, quinoline ring, isoquinoline ring, or C3-C8 aliphatic ring; The R j 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, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, and the group shown in Formula II; The R k R l The group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, and the group shown in Formula II; The R n The same or different from one of the following groups: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, fluorene; The c1 is selected from 0, 1, 2, 3 or 4; the c2 is selected from 0, 1, 2 or 3; the c3 is selected from 0, 1 or 2; the c4 is selected from 0, 1, 2, 3, 4, 5 or 6; the c5 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; the c6 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; the c7 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 R6, the two or more R6 are the same as or different from each other.

[0056] The R6, R j R k R l R n 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, the structure shown in Formula I contains one or more groups shown in Formula II.

[0058] Preferably, the structure shown in Formula I contains one, two, three, four, five, six or more groups shown in Formula II.

[0059] Preferably, the Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, L5, L6, L a L b L c At least one of them contains one or more groups shown in Formula II.

[0060] Preferably, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contains one or more groups represented by Formula II.

[0061] Preferably, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contains one, two, three, or more groups represented by Formula II.

[0062] Preferably, Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contain one, two, three, four, five, six, or more groups represented by Formula II.

[0063] Preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 independently contain one, two, three, or more groups represented by Formula II.

[0064] Preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 independently contain one, two, or three groups represented by Formula II.

[0065] Preferably, one, two, three, four, five, or six of the Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 independently each contain a group represented by Formula II.

[0066] Preferably, one, two, three, four, five, six or more of R5 are independently selected from the groups shown in Formula II.

[0067] Preferably, one or both of the R5 groups of Ar1 are independently selected from the groups shown in Formula II.

[0068] Preferably, one or both of the R5 groups of Ar2 are independently selected from the groups shown in Formula II.

[0069] Preferably, one or both of the R5 groups of Ar3 are independently selected from the groups shown in Formula II.

[0070] Preferably, one or both of the R5 groups of Ar4 are independently selected from the groups shown in Formula II.

[0071] Preferably, one or both of the R5 groups of Ar5 are independently selected from the groups shown in Formula II.

[0072] Preferably, one or both of the R5 groups in Ar6 are independently selected from the groups shown in Formula II.

[0073] Preferably, one, two, three, four, five, or six of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, wherein one or two of R5 in each group are independently selected from the groups represented by Formula II.

[0074] Preferably, at least one of L1, L2, L3, L4, L5, and L6 contains one or more groups represented by Formula II.

[0075] Preferably, the L, L a L b L c At least one of them contains one or more groups shown in Formula II.

[0076] Most preferably, the triarylamine compound is selected from any one of the following structures: .

[0077] The above lists some specific structural forms of the triarylamine compounds of Formula I of the present invention. However, the present invention is not limited to these chemical structures. Any structure based on the structure shown in Formula I, with substituents as defined above, should be included.

[0078] 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 one or more 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.

[0079] The organic layer of this 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, an electron blocking layer, and a light-emitting auxiliary layer. The electron transport region includes functional layers such as a hole blocking layer, an electron transport layer, and an electron injection layer. The number of organic functional layers can be increased or decreased according to actual needs. The organic layer of 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 hole transport layer can include a first hole transport layer and a second hole transport layer, and the electron transport layer can include a first electron transport layer and a second electron transport layer. Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, which includes any one or a combination of at least two of the triarylamine compounds described in this invention.

[0080] Preferably, the hole transport region includes an electron blocking layer, which contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0081] 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.

[0082] 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 hole injection layer and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and at least one of the first hole transport layer and the second hole transport layer contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0083] Preferably, the organic layer is located outside one or more of the electrodes, namely the anode and the cathode, and the organic layer includes a capping layer, which contains any one or a combination of at least two of the triarylamine compounds described in this invention.

[0084] Preferably, the covering layer is located on the outside of the cathode.

[0085] 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: 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.

[0086] The anode material described in this invention is preferably a high work function material. Specific examples of anode materials that can be used in this invention 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 are not limited thereto.

[0087] The hole injection material described in this invention is preferably a material with good hole-accepting ability. Specific examples of hole injection materials that can be used in this invention may include: metal oxides such as silver oxide, vanadium oxide, tungsten oxide, copper oxide, and titanium oxide; phthalocyanine compounds; benzidine compounds; phenazine compounds; etc., 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... Aniline (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), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), etc., but not limited to these.

[0088] The hole transport layer material described in this invention is preferably a material with high hole mobility. In addition to the triarylamine compounds described in this invention, the hole transport materials that can be used in this invention also include 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 are not limited thereto.

[0089] The light-emitting layer material of this invention comprises a host material and a dopant material. The preferred mass ratio of the host material to the dopant material is (90–99.5):(0.5–10). The host material can be selected from 4,4'-bis(9-carbazole)biphenyl (CBP), 4,4'-bis(9-carbazole)-2,2'-dimethylbiphenyl (CDBP), 9,9'-(2,6-pyridinidyldi-3,1-phenylene)bis-9H-carbazole (26DCZPPY), 9,9'-diphenyl-9H-carbazole, etc. H ,9' H -3,3'-Bicarbazole (BCzPh), 9-(5-(3-(9H-carbazole-9-yl)phenyl)pyridin-3-yl)-9H-carbazole (CPPyC), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 1,3-bis(N-carbazole)phenyl (MCP), 9,9-dimethyl-N,N-diphenyl-7-(4-(1-phenyl-1Hbenzimidazol-2-yl)phenyl)-9H-fluorene-2-amine (EFIN), 9,10-di(2-naphthyl)anthracene (ADN), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (TBADN), 1-(7-[9,9'-bianthra]-10-yl-9,9-dioctyl-9H-fluorene-2-yl)pyrene (BAnF8Pye), 9,9,9',9'-tetra(4-methylphenyl)-2,2'-bi-9H-fluorene (BDAF), tris(8-hydroxyquinoline)aluminum (Alq3), bis(10-hydroxybenzo[H]quinoline)beryllium (BeBq2), bis(8-hydroxyquinoline)zinc (Znq2), etc., but not limited to these. The doping material for the luminescent layer can be selected from (6-(4-(diphenylamino(phenyl)-N,N-diphenylpyrene-1-amine)(DPAP-DPPA), 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-phenylpyridine)iridium (Ir(ppy)3), bis(2-phenylpyridine)iridium acetylacetonate (Ir(ppy)2(acac)), 9,10-bis[N-(p-tolyl)aniline]anthracene (TPA), tri[1-phenylisoquinoline-C2,N]iridium(III) (Ir(piq)3), bis(1-phenylisoquinoline)(acetylacetonate)iridium (Ir(piq)2(acac)), etc., but not limited to these.

[0090] The electron transport layer material described in this invention is preferably a material with high electron mobility. Specific examples of electron transport materials that can be used in this invention include: imidazoles, triazoles, phenanthroline derivatives, quinolines, etc., such as 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 1,3,5-tris[(3-pyridyl)-phenyl]benzene (TmPyPB), 4,4'-bis(4,6-diphenyl-1,3,5-triazinyl)biphenyl (BTB), 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 2-(naphthyl-2-yl)-4,7-(diphenyl)-1,10-o-phenanthroline (HNBphen), 8-hydroxyquinoline-lithium, etc. (LiQ), etc., but are not limited thereto.

[0091] The electron injection material described in this invention preferably possesses good electron injection capability and can reduce the interfacial barrier between the cathode and the electron transport layer. Specific examples of electron injection materials that can be used in this invention may include, but are not limited to, alkali metal salts (such as LiF, CsF), alkaline earth metal salts (such as MgF2), and metal oxides (such as Al2O3, MoO3).

[0092] The cathode material described in this invention is preferably a material with a low work function. Specific examples of cathode materials that can be used in this invention may include: metals such as aluminum, magnesium, silver, indium, tin, titanium, and their alloys; multilayer metal materials such as LiF / Al, Mg / Ag, Li / Al, LiO2 / Al, BaF2 / Al, etc., but are not limited thereto.

[0093] The capping material described in this invention preferably has a high glass transition temperature and excellent light extraction performance. In addition to the triarylamine compounds described in this invention, the capping material that can be used in this invention also includes, but is not limited to, carbazole derivatives, benzimidazole derivatives, triazole derivatives, lithium fluoride, etc.

[0094] 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.

[0095] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device of the present invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, vapor deposition, etc. can be used, but it is not limited to these methods.

[0096] The organic electroluminescent device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, signs, signal lights, electronic paper, organic solar cells, organic photosensitive materials, or organic thin-film transistors, but is not limited thereto.

[0097] Synthesis Examples

[0098] There are no particular limitations on the preparation method of the triarylamine compounds represented by Formula I 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:

[0099] Xa, Xb, and Xc are independently selected from any one of I, Br, and Cl.

[0100] 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.

[0101] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0102] Synthesis Example 1: Preparation of raw material a-136

[0103] Under nitrogen protection, i-136 (24.71 g, 60 mmol), j-136 (9.38 g, 60 mmol), Pd(PPh3)4 (0.69 g, 0.60 mmol), and K2CO3 (24.88 g, 180 mmol) and 300 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. The mixture was stirred and heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from ethyl acetate and dried to obtain the starting material a-136 (18.08 g, yield 76%). The purity of the solid was ≥99.81% as determined by HPLC. Mass spectrometry m / z: 3393.8771 (theoretical value: 393.8760).

[0104] By substituting the raw materials accordingly, and following the preparation method of raw material a-136 in Synthesis Example 1, raw material a can be prepared. The raw materials are shown in the table below:

[0105] Synthesis Example 2: Preparation of raw material b-4

[0106] Under nitrogen protection, e-4 (10.24 g, 110.00 mmol), f-4 (24.99 g, 110.00 mmol), sodium tert-butoxide (21.14 g, 220.00 mmol), Pd(dppf)Cl2 (0.95 g, 1.30 mmol), and 550 ml of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from ethyl acetate and dried to obtain the starting material b-4 (21.85 g, 83%). The purity of the solid was ≥99.75% as determined by HPLC. Mass spectrometry m / z: 239.1689 (theoretical value: 239.1674).

[0107] By substituting the raw materials accordingly, and following the preparation method of raw material b-1 in Synthesis Example 2, raw material b / c can be prepared. The raw materials are shown in the table below:

[0108]

[0109] Synthesis Example 3: Preparation of Compound 4

[0110] Preparation of intermediate A-4: Under nitrogen protection, a-4 (12.82 g, 40.00 mmol), b-4 (19.15 g, 80.00 mmol), Pd(OAc)2 (0.20 g, 0.90 mmol), P(t-Bu)3 (3.20 mL of 0.5 M toluene solution, 1.60 mmol), NaOt-Bu (15.38 g, 160.00 mmol), and 400 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give intermediate A-4 (20.14 g, yield 79%) with an HPLC purity ≥ 99.87%. Mass spectrometry m / z: 636.3281 (theoretical value: 636.3271).

[0111] Preparation of compound 4: Under nitrogen protection, intermediates A-4 (12.75 g, 20.00 mmol), c-4 (4.83 g, 20.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), X-Phos (0.29 g, 0.60 mmol), NaOt-Bu (3.84 g, 40.00 mmol), and 100 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 7 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give compound 4 (12.63 g, 75%) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 841.4775 (theoretical value: 841.4791). Theoretical elemental content (%) C 59 H 63 N3Si: C, 84.14; H, 7.54; N, 4.99. Measured elemental content (%): C, 84.16; H, 7.51; N, 5.03.

[0112] Synthesis Example 4: Preparation of Compound 20

[0113] Under nitrogen protection, a-20 (7.30 g, 20.00 mmol), c-20 (14.79 g, 60.00 mmol), Pd2(dba)3 (0.69 g, 0.75 mmol), X-Phos (0.72 g, 1.50 mmol), NaOt-Bu (11.53 g, 120.00 mmol), and 300 ml of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give compound 20 (13.09 g, 76%), with an HPLC purity of ≥99.96%. Mass spectrometry m / z: 860.4971 (theoretical value: 860.4958). Theoretical elemental content (%) C 55 H 44 D 15 N3Si3: C, 76.69; H, 8.66; N, 4.88; . Measured elemental content (%): C, 76.72; H, 8.68; N, 4.87;.

[0114] Synthesis Example 5: Preparation of Compound 24

[0115] Preparation of intermediate B-24: Under nitrogen protection, a-24 (11.60 g, 40.00 mmol), c-4 (14.38 g, 40.00 mmol), Pd(OAc)2 (0.11 g, 0.50 mmol), P(t-Bu)3 (2.00 mL of 0.5 M toluene solution, 1.00 mmol), NaOt-Bu (9.61 g, 100.00 mmol), and 200 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give intermediate B-24 (18.20 g, 80% yield) with an HPLC purity of ≥99.83%. Mass spectrometry m / z: 567.1902 (theoretical value: 567.1916).

[0116] Preparation of compound 24: Under nitrogen protection, intermediates B-24 (11.37 g, 20.00 mmol), b-24 (6.77 g, 40.00 mmol), Pd2(dba)3 (0.46 g, 0.50 mmol), X-Phos (0.48 g, 1.00 mmol), NaOt-Bu (9.61 g, 100.00 mmol), and 200 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 6 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give compound 4 (12.51 g, 75%) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 833.4182 (theoretical value: 833.4165). Theoretical elemental content (%) C 59 H 55 N3Si: C, 84.95; H, 6.65; N, 5.04. Measured elemental content (%): C, 85.01; H, 6.63; N, 5.03.

[0117] Synthesis Example 6: Preparation of Compound 46

[0118] Following the preparation method of Synthesis Example 3, b-4 was replaced with an equimolar amount of b-46, and c-4 was replaced with an equimolar amount of c-46, yielding compound 46 (13.21 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 929.4175 (theoretical value: 929.4165). Theoretical elemental content (%) C 67 H 55N3Si: C, 86.50; H, 5.96; N, 4.52. Measured elemental content (%): C, 86.46; H, 5.99; N, 4.55.

[0119] Synthesis Example 7: Preparation of Compound 64

[0120] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-64, b-4 was replaced with an equimolar amount of c-64, and c-4 was replaced with an equimolar amount of b-24, yielding compound 64 (13.15 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 925.4261 (theoretical value: 925.4248). Theoretical elemental content (%) C 64 H 59 N3Si2: C, 82.98; H, 6.42; N, 4.54. Measured elemental content (%): C, 83.03; H, 6.39; N, 4.56.

[0121] Synthesis Example 8: Preparation of Compound 72

[0122] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-72, and c-24 was replaced with an equimolar amount of c-72, yielding compound 72 (12.47 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 853.3843 (theoretical value: 853.3852). Theoretical elemental content (%) C 61 H 51 N3Si: C, 85.77; H, 6.02; N, 4.92. Measured elemental content (%): C, 85.73; H, 6.05; N, 4.96.

[0123] Synthesis Example 9: Preparation of Compound 82

[0124] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-82, b-4 was replaced with an equimolar amount of c-82, and c-4 was replaced with an equimolar amount of b-24, yielding compound 82 (12.76 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 873.3949 (theoretical value: 873.3935). Theoretical elemental content (%) C 60 H 55 N3Si2: C, 82.43; H, 6.34; N, 4.81. Measured elemental content (%): C, 82.46; H, 6.32; N, 4.79.

[0125] Synthesis Example 10: Preparation of Compound 87

[0126] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-87, b-4 with an equimolar amount of b-87, and c-4 with an equimolar amount of c-87, yielding compound 87 (12.18 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 811.4159 (theoretical value: 811.4167). Theoretical elemental content (%) C 57 H 37 D 10 N3Si: C, 84.30; H, 7.07; N, 5.17. Measured elemental content (%): C, 84.27; H, 7.11; N, 5.20.

[0127] Synthesis Example 11: Preparation of Compound 100

[0128] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-100, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-100, yielding compound 100 (12.27 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 817.3864 (theoretical value: 817.3852). Theoretical elemental content (%) C 58 H 51 N3Si: C, 85.15; H, 6.28; N, 5.14. Measured elemental content (%): C, 85.16; H, 6.32; N, 5.11.

[0129] Synthesis Example 12: Preparation of Compound 103

[0130] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-103, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-103, yielding compound 103 (13.19 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 941.4181 (theoretical value: 941.4165). Theoretical elemental content (%) C 68 H 55 N3Si: C, 86.68; H, 5.88; N, 4.46. Measured elemental content (%): C, 86.71; H, 5.92; N, 4.43.

[0131] Synthesis Example 13: Preparation of Compound 104

[0132] Preparation of intermediate C-104: Under nitrogen protection, a-104 (22.04 g, 60.00 mmol), b-24 (10.15 g, 60.00 mmol), Pd(dppf)Cl2 (0.55 g, 0.75 mmol), NaOt-Bu (11.53 g, 120.00 mmol), and 300 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 4 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give intermediate C-104 (20.35 g, 83%) with an HPLC purity of ≥99.76%. Mass spectrometry m / z: 407.0087 (theoretical value: 407.0076).

[0133] Preparation of intermediate D-104: Under nitrogen protection, intermediates C-104 (16.35 g, 40.00 mmol), C-4 (9.66 g, 40.00 mmol), Pd(OAc)2 (0.11 g, 0.50 mmol), P(t-Bu)3 (2.00 mL of 0.5 M toluene solution, 1.00 mmol), NaOt-Bu (9.61 g, 100.00 mmol), and 200 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 5 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The layers were allowed to stand and separated, and the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to obtain intermediate D-104 (18.22 g, 80%) with an HPLC purity of ≥99.85%. Mass spectrometry m / z: 568.2115 (theoretical value: 568.2102).

[0134] Preparation of compound 104: Under nitrogen protection, intermediates D-104 (11.38 g, 20.00 mmol), d-104 (8.15 g, 20.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), X-Phos (0.29 g, 0.60 mmol), NaOt-Bu (3.84 g, 40.00 mmol), and 100 mL of toluene solvent were added to a reaction flask. The mixture was stirred and heated under reflux for 7 h. After the reaction was completed, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The filtrate was recrystallized from toluene to give compound 104 (13.16 g, 75%) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 939.4027 (theoretical value: 939.4009). Theoretical elemental content (%) C 68 H 53 N3Si: C, 86.86; H, 5.68; N, 4.47. Measured elemental content (%): C, 86.88; H, 5.71; N, 4.45.

[0135] Synthesis Example 14: Preparation of Compound 127

[0136] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-127, b-4 was replaced with an equimolar amount of c-4, and c-4 was replaced with an equimolar amount of b-127, yielding compound 127 (12.72 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 870.4180 (theoretical value: 870.4167). Theoretical elemental content (%) C 58 H 46 D7N3OSi2: C, 79.95; H, 6.94; N, 4.82. Measured elemental content (%): C, 79.93; H, 6.99; N, 4.81.

[0137] Synthetic Example 15: Preparation of Compound 136

[0138] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-136, b-4 was replaced with an equimolar amount of c-4, and c-4 was replaced with an equimolar amount of b-136, yielding compound 136 (13.47 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 975.4415 (theoretical value: 975.4404). Theoretical elemental content (%) C 68 H 61N3Si2: C, 83.65; H, 6.30; N, 4.30. Measured elemental content (%): C, 83.70; H, 6.26; N, 4.27.

[0139] Synthetic Example 16: Preparation of Compound 177

[0140] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-177, and c-24 was replaced with an equimolar amount of c-177, yielding compound 177 (12.75 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 884.4279 (theoretical value: 884.4292). Theoretical elemental content (%) C 63 H 44 D7N3Si: C, 85.48; H, 6.60; N, 4.75. Measured elemental content (%): C, 85.51; H, 6.58; N, 4.79.

[0141] Synthesis Example 17: Preparation of Compound 212

[0142] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-212, and c-24 was replaced with an equimolar amount of c-212, yielding compound 212 (13.02 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 903.4017 (theoretical value: 903.4009). Theoretical elemental content (%) C 65 H 53 N3Si: C, 86.34; H, 5.91; N, 4.65. Measured elemental content (%): C, 86.36; H, 5.88; N, 4.68.

[0143] Synthesis Example 18: Preparation of Compound 223

[0144] Following the preparation method of Synthesis Example 3, a-20 was replaced with an equimolar amount of a-223, and c-20 was replaced with an equimolar amount of c-4, yielding compound 223 (13.25 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 945.4345 (theoretical value: 945.4330). Theoretical elemental content (%) C 63 H 63 N3Si3: C, 79.95; H, 6.71; N, 4.44. Measured elemental content (%): C, 79.98; H, 6.69; N, 4.47.

[0145] Synthesis Example 19: Preparation of Compound 233

[0146] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-233, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-233, yielding compound 233 (13.18 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 927.3633 (theoretical value: 927.3645). Theoretical elemental content (%) C 66 H 49 N3OSi: C, 85.40; H, 5.32; N, 4.53. Measured elemental content (%): C, 85.36; H, 5.29; N, 4.57.

[0147] Synthesis Example 20: Preparation of Compound 267

[0148] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-267, b-4 was replaced with an equimolar amount of c-4, and c-4 was replaced with an equimolar amount of b-267, yielding compound 267 (13.28 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 947.4651 (theoretical value: 947.4666). Theoretical elemental content (%) C 64 H 65 N3OSi2: C, 81.05; H, 6.91; N, 4.43. Measured elemental content (%): C, 81.09; H, 6.88; N, 4.46.

[0149] Synthesis Example 21: Preparation of Compound 279

[0150] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-279, b-4 with an equimolar amount of b-279, and c-4 with an equimolar amount of c-46, yielding compound 279 (13.21 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 929.4756 (theoretical value: 929.4740). Theoretical elemental content (%) C 65 H 63 N3OSi: C, 83.92; H, 6.83; N, 4.52. Measured elemental content (%): C, 83.95; H, 6.81; N, 4.55.

[0151] Synthesis Example 22: Preparation of Compound 282

[0152] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-267, and b-4 was replaced with an equimolar amount of b-282, yielding compound 282 (12.88 g) with an HPLC purity ≥ 99.99%. Mass spectrometry m / z: 893.3813 (theoretical value: 893.3801). Theoretical elemental content (%) C 63 H 51 N3OSi: C, 84.62; H, 5.75; N, 4.70. Measured elemental content (%): C, 84.65; H, 5.77; N, 4.69.

[0153] Synthesis Example 23: Preparation of Compound 292

[0154] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-233, and b-4 was replaced with an equimolar amount of b-292, yielding compound 292 (12.70 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 893.3815 (theoretical value: 893.3801). Theoretical elemental content (%) C 63 H 51 N3OSi: C, 84.62; H, 5.75; N, 4.70. Measured elemental content (%): C, 84.64; H, 5.78; N, 4.67.

[0155] Synthesis Example 24: Preparation of Compound 318

[0156] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-318, b-4 with an equimolar amount of b-282, and c-4 with an equimolar amount of c-46, yielding compound 318 (13.39 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 969.4126 (theoretical value: 969.4114). Theoretical elemental content (%) C 69 H 55 N3OSi: C, 85.41; H, 5.71; N, 4.33. Measured elemental content (%): C, 85.38; H, 5.69; N, 4.37.

[0157] Synthesis Example 25: Preparation of Compound 348

[0158] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-348, and c-24 was replaced with an equimolar amount of c-348, yielding compound 348 (13.15 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 925.4441 (theoretical value: 925.4427). Theoretical elemental content (%) C 65 H 59 N3OSi: C, 84.28; H, 6.42; N, 4.54. Measured elemental content (%): C, 84.32; H, 6.45; N, 4.51.

[0159] Synthesis Example 26: Preparation of Compound 361

[0160] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-361, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-361, yielding compound 361 (12.93 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 909.4104 (theoretical value: 909.4114). Theoretical elemental content (%) C 64 H 55 N3OSi: C, 84.45; H, 6.09; N, 4.62. Measured elemental content (%): C, 84.46; H, 6.11; N, 4.63.

[0161] Synthesis Example 27: Preparation of Compound 367

[0162] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-267, b-4 with an equimolar amount of b-367, and c-4 with an equimolar amount of c-367, yielding compound 367 (12.88 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 893.4214 (theoretical value: 893.4197). Theoretical elemental content (%) C 60 H 59 N3OSi2: C, 80.58; H, 6.65; N, 4.70. Measured elemental content (%): C, 80.61; H, 6.66; N, 4.68.

[0163] Synthesis Example 28: Preparation of Compound 385

[0164] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-267, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-385, yielding compound 385 (13.56 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 981.4127 (theoretical value: 981.4114). Theoretical elemental content (%) C 70 H 55 N3OSi: C, 85.59; H, 5.64; N, 4.28. Measured elemental content (%): C, 85.61; H, 5.66; N, 4.27.

[0165] Synthesis Example 29: Preparation of Compound 390

[0166] Following the preparation method of Synthesis Example 3, A-4 was replaced with an equimolar amount of A-233, and c-4 was replaced with an equimolar amount of c-390, yielding compound 390 (13.11 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 949.4415 (theoretical value: 949.4427). Theoretical elemental content (%) C 67 H 59 N3OSi: C, 84.68; H, 6.26; N, 4.42. Measured elemental content (%): C, 84.72; H, 6.31; N, 4.37.

[0167] Synthesis Example 30: Preparation of Compound 394

[0168] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-267, b-4 was replaced with an equimolar amount of c-394, and c-4 was replaced with an equimolar amount of b-394, yielding compound 394 (13.18 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 940.3978 (theoretical value: 940.3993). Theoretical elemental content (%) C 63 H 56 N4OSi2: C, 80.38; H, 6.00; N, 5.95. Measured elemental content (%): C, 80.43; H, 5.98; N, 5.96.

[0169] Synthesis Example 31: Preparation of Compound 399

[0170] Following the preparation method of Synthesis Example 3, A-4 was replaced with an equimolar amount of A-385, and c-4 was replaced with an equimolar amount of c-399, yielding compound 399 (12.53 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 857.3451 (theoretical value: 857.3438). Theoretical elemental content (%) C 59 H 47 N3O2Si: C, 82.58; H, 5.52; N, 4.90. Measured elemental content (%): C, 82.61; H, 5.56; N, 4.87.

[0171] Synthesis Example 32: Preparation of Compound 413

[0172] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-233, b-4 was replaced with an equimolar amount of c-4, and c-4 was replaced with an equimolar amount of b-413, yielding compound 413 (13.25 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 945.3622 (theoretical value: 945.3604). Theoretical elemental content (%) C 62 H 55 N3OSSi2: C, 78.69; H, 5.86; N, 4.44. Measured elemental content (%): C, 78.65; H, 5.91; N, 4.41.

[0173] Synthesis Example 33: Preparation of Compound 425

[0174] Following the preparation method of Synthesis Example 13, a-104 was replaced with an equimolar amount of a-425, c-4 was replaced with an equimolar amount of c-425, and d-104 was replaced with an equimolar amount of d-425, yielding compound 425 (13.12 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 923.3918 (theoretical value: 923.3907). Theoretical elemental content (%) C 64 H 53 N3O2Si: C, 83.17; H, 5.78; N, 4.55. Measured elemental content (%): C, 83.20; H, 5.81; N, 4.53.

[0175] Synthesis Example 34: Preparation of Compound 427

[0176] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-233, and b-4 was replaced with an equimolar amount of b-427, yielding compound 427 (12.91 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 921.3371 (theoretical value: 921.3387). Theoretical elemental content (%) C 63 H 47 N3O3Si: C, 82.06; H, 5.14; N, 4.56. Measured elemental content (%): C, 82.11; H, 5.12; N, 4.55.

[0177] Synthesis Example 35: Preparation of Compound 430

[0178] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-279, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-430, yielding compound 430 (13.00 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 927.3626 (theoretical value: 927.3617). Theoretical elemental content (%) C 63 H 45 D4N3OSSi: C, 81.52; H, 5.75; N, 4.53. Measured elemental content (%): C, 81.53; H, 5.76; N, 4.56.

[0179] Synthesis Example 36: Preparation of Compound 432

[0180] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-432, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-432, yielding compound 432 (12.94 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 910.4025 (theoretical value: 910.4005). Theoretical elemental content (%) C 63 H 46 D4N4OSi: C, 83.04; H, 5.97; N, 6.15. Measured elemental content (%): C, 83.06; H, 6.01; N, 6.12.

[0181] Synthesis Example 37: Preparation of Compound 433

[0182] Following the preparation method of Synthesis Example 3, A-4 was replaced with an equimolar amount of A-233, and c-4 was replaced with an equimolar amount of c-433, yielding compound 433 (13.55 g) with an HPLC purity ≥ 99.93%. Mass spectrometry m / z: 995.3921 (theoretical value: 995.3907). Theoretical elemental content (%) C 70 H 53 N3O2Si: C, 84.39; H, 5.36; N, 4.22. Measured elemental content (%): C, 84.41; H, 5.40; N, 4.21.

[0183] Synthesis Example 38: Preparation of Compound 441

[0184] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-441, b-4 was replaced with an equimolar amount of b-24, and c-4 was replaced with an equimolar amount of c-441, yielding compound 441 (13.42 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 957.3739 (theoretical value: 957.3751). Theoretical elemental content (%) C 67 H 51 N3O2Si: C, 83.98; H, 5.36; N, 4.39. Measured elemental content (%): C, 84.01; H, 5.32; N, 4.42.

[0185] Synthesis Example 39: Preparation of Compound 460

[0186] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-460, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-46, yielding compound 460 (13.39 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 983.3919 (theoretical value: 983.3907). Theoretical elemental content (%) C 69 H 53 N3O2Si: C, 84.20; H, 5.43; N, 4.27. Measured elemental content (%): C, 84.23; H, 5.45; N, 4.26.

[0187] Synthesis Example 40: Preparation of Compound 560

[0188] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-560, b-4 with an equimolar amount of b-24, and c-4 with an equimolar amount of c-560, yielding compound 560 (13.72 g) with an HPLC purity ≥ 99.94%. Mass spectrometry m / z: 1007.4655 (theoretical value: 1007.4668). Theoretical elemental content (%) C 70 H 65 N3SSi: C, 83.37; H, 6.50; N, 4.17. Measured elemental content (%): C, 83.41; H, 6.47; N, 4.21.

[0189] Synthesis Example 41: Preparation of Compound 588

[0190] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-588, b-4 with an equimolar amount of b-87, and c-4 with an equimolar amount of c-588, yielding compound 588 (13.07 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 932.4162 (theoretical value: 932.4153). Theoretical elemental content (%) C 63 H 40 D 10 N4SSi: C, 81.07; H, 6.48; N, 6.00. Measured elemental content (%): C, 81.05; H, 6.51; N, 6.01.

[0191] Synthesis Example 42: Preparation of Compound 613

[0192] Following the preparation method of Synthesis Example 3, a-4 was replaced with an equimolar amount of a-613, b-4 was replaced with an equimolar amount of c-4, and c-4 was replaced with an equimolar amount of b-613, yielding compound 613 (12.90 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 920.4732 (theoretical value: 920.4718). Theoretical elemental content (%) C 63 H 56 D5N3Si2: C, 82.12; H, 7.22; N, 4.56. Measured elemental content (%): C, 82.13; H, 7.25; N, 4.54.

[0193] Synthesis Example 43: Preparation of Compound 636

[0194] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-636, and c-24 was replaced with an equimolar amount of c-4, yielding compound 636 (12.29 g) with an HPLC purity ≥ 99.97%. Mass spectrometry m / z: 889.3866 (theoretical value: 889.3852). Theoretical elemental content (%) C 64 H 45 N3Si: C, 86.35; H, 5.77; N, 4.72. Measured elemental content (%): C, 86.37; H, 5.78; N, 4.73.

[0195] Synthesis Example 44: Preparation of Compound 642

[0196] Following the preparation method of Synthesis Example 4, a-20 was replaced with an equimolar amount of a-642, and c-20 was replaced with an equimolar amount of c-4, yielding compound 642 (14.08 g) with an HPLC purity ≥ 99.92%. Mass spectrometry m / z: 1049.4574 (theoretical value: 1049.4592). Theoretical elemental content (%) C 70 H 67 N3OSi3: C, 80.03; H, 6.43; N, 4.00. Measured elemental content (%): C, 80.05; H, 6.41; N, 4.05.

[0197] Synthesis Example 45: Preparation of Compound 656

[0198] Following the preparation method of Synthesis Example 4, a-20 was replaced with an equimolar amount of a-656, and c-20 was replaced with an equimolar amount of c-4, yielding compound 656 (13.27 g) with an HPLC purity ≥ 99.95%. Mass spectrometry m / z: 960.4451 (theoretical value: 960.4439). Theoretical elemental content (%) C 63 H 64 N4Si3: C, 78.70; H, 6.71; N, 5.83. Measured elemental content (%): C, 78.65; H, 6.74; N, 5.88.

[0199] Synthesis Example 46: Preparation of Compound 668

[0200] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-668, and c-24 was replaced with an equimolar amount of c-668, yielding compound 668 (12.89 g) with an HPLC purity ≥ 99.96%. Mass spectrometry m / z: 933.3847 (theoretical value: 933.3863). Theoretical elemental content (%) C 64 H 51 N5OSi: C, 82.28; H, 5.50; N, 7.50. Measured elemental content (%): C, 82.30; H, 5.53; N, 7.49.

[0201] Synthesis Example 47: Preparation of Compound 713

[0202] Following the preparation method of Synthesis Example 5, a-24 was replaced with an equimolar amount of a-713, and c-24 was replaced with an equimolar amount of c-713, yielding compound 713 (12.45 g) with an HPLC purity ≥ 99.98%. Mass spectrometry m / z: 840.3743 (theoretical value: 840.3728). Theoretical elemental content (%) C 60 H 44 D3N3Si: C, 85.67; H, 5.99; N, 5.00. Measured elemental content (%): C, 85.69; H, 6.03; N, 4.97.

[0203] [Comparative Example 1] Device Fabrication Example: (Hole Transport Layer)

[0204] 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.

[0205] HI-1 was deposited as a hole injection layer with a thickness of 12 nm on a cleaned ITO / Ag / ITO substrate. Comparative compound 1 was then deposited as a hole transport layer with a thickness of 56 nm on the hole injection layer. A mixture of BH-1 and BD-1 (mass ratio 95:5) was then vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 40 nm. ET-1 and Liq (mass ratio 1:1) were then deposited on the light-emitting layer as an electron transport layer with a thickness of 35 nm. LiF was then deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Mg:Ag (mass ratio 1:9) was then deposited on the 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 57 nm, thus fabricating an organic electroluminescent device (the material structures of each functional layer in the fabrication process of the organic electroluminescent device are as follows).

[0206]

[0207] [Examples 1-30]

[0208] The hole transport layer material of the organic electroluminescent device is sequentially replaced with compounds 4, 20, 46, 64, 72, 87, 100, 104, 127, 136, 177, 212, 233, 267, 279, 282, 292, 318, 367, 385, 390, 399, 427, 430, 441, 460, 560, 588, 613, and 642 of this invention, while the other steps are the same as in Comparative Example 1.

[0209] A combined IVL testing system was constructed using testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter to test the driving voltage and luminous efficiency of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, and the temperature was room temperature. The luminous characteristics test results of the organic electroluminescent devices obtained in Comparative Device Example 1, Device Examples 1-30 are shown in Table 1 below.

[0210] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices

[0211] As shown in Table 1, compared with Comparative Example 1, when the triarylamine compounds described in this invention are used as hole transport layer materials in organic electroluminescent devices, the devices have higher luminous efficiency and longer lifespan.

[0212] [Comparative Examples 2-3] Device Fabrication Example: (Second Hole Transport Layer)

[0213] 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.

[0214] HI-1 was deposited as a hole injection layer with a thickness of 10 nm on a cleaned ITO / Ag / ITO substrate. HT1 was then deposited as a first hole transport layer with a thickness of 37 nm on this hole injection layer. Comparative compound 2 was then deposited as a second hole transport layer with a thickness of 33 nm on this first hole transport layer. A mixture of GH-1, GH-2, and GD-1 (mass ratio 47:47:6) was then vacuum-deposited onto the 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 15 nm. Finally, CP-1 is vacuum-deposited on the cathode as a capping layer with a thickness of 55 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).

[0215]

[0216] Comparative Example 3: The second hole transport layer material, comparative compound 2, in Comparative Example 2 was replaced with comparative compound 3, and the other steps were the same as in Comparative Example 2.

[0217] [Examples 31-75]

[0218] The second hole transport layer material of the organic electroluminescent device is sequentially replaced with compounds 4, 20, 24, 46, 64, 72, 82, 87, 100, 103, 104, 127, 136, 177, 212, 223, 233, 267, 279, 282, 292, 318, 348, 361, 367, 385, 390, 394, 399, 413, 425, 427, 430, 432, 433, 441, 460, 560, 588, 613, 636, 642, 656, 668, and 713 of this invention. Other steps are the same as in Comparative Example 2. The luminescence characteristics test results of the organic electroluminescent devices obtained in comparative device examples 2-3 and device examples 31-75 of the present invention are shown in Table 2 below.

[0219] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices

[0220]

[0221] As shown in Table 2, compared with Comparative Examples 2-3, using the triarylamine compounds described in this invention as the second hole transport layer material in organic electroluminescent devices can significantly improve the luminous efficiency of the devices and extend their service life.

[0222] [Comparative Example 4] Device Fabrication Example: (Cover Layer)

[0223] Comparative Example 4: 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.

[0224] HI-1 was deposited as a hole injection layer with a thickness of 10 nm on a cleaned ITO / Ag / ITO substrate. HT-2 was then deposited as a hole transport layer with a thickness of 57 nm on the hole injection layer. A mixture of RH-1 and RD-1 (mass ratio 97:3) was then vacuum-deposited on the hole transport layer to form a light-emitting layer with a thickness of 39 nm. ET-1 and Liq (mass ratio 1:1) were then deposited on the light-emitting layer as an electron transport layer with a thickness of 40 nm. LiF was then deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm. Mg:Ag (mass ratio 1:9) was then deposited on the electron injection layer as a cathode with a thickness of 10 nm. Finally, comparative compound 4 was vacuum-deposited on the cathode as a capping layer with a thickness of 60 nm, thus fabricating an organic electroluminescent device (the material structures of each functional layer in the fabrication process of the organic electroluminescent device are as follows).

[0225]

[0226]

[0227] [Examples 76-90]

[0228] The capping material of the organic electroluminescent device was sequentially replaced with compounds 64, 87, 127, 267, 279, 282, 292, 318, 367, 394, 399, 413, 588, 613, 656, and 668 of the present invention, with other steps being the same as in Comparative Example 4. The luminescence characteristics test results of the organic electroluminescent devices obtained in Comparative Device Example 4 and Device Examples 76-90 of the present invention are shown in Table 3 below.

[0229] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices

[0230] As shown in Table 3, compared with Comparative Example 4, the use of the triarylamine compounds described in this invention as a capping material in organic electroluminescent devices significantly improves the luminous efficiency and lifespan of the devices.

[0231] 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 I: The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. The L is selected from any one of the following groups: The x may be the same or different from CH or N; Y1 is selected from one of O, S, C(R2R3), and N(R4); The Y2 is selected from one of the following: single bond, O, S, C (R7R8), and N (R9); The R1s are selected from one of the following groups, either identically or differently: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic group, substituted or unsubstituted C2-C30 heteroaryl, or fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or two adjacent R1s may be interconnected to form substituted or unsubstituted rings. R2, R3, R7, and R8 are independently selected from one of the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 alicyclic group, substituted or unsubstituted C6-C30 aryl, fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic ring, substituted or unsubstituted C2-C30 heteroaryl, and fused cyclic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl; or R2 and R3 can be interconnected to form substituted or unsubstituted rings. R4 and R9 are independently selected from one of the following: substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C6-C30 aromatic groups, substituted or unsubstituted C2-C30 heteroaryl groups, and fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic groups and C2-C30 heteroaryl groups. a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1 or 2; when there are two or more R1s, the two or more R1s are the same as or different from each other; The L1, L2, L3, L4, L5, L6, L a L b L c It is independently selected from one of the following: a single bond, a substituted or unsubstituted C6-C30 arylene, a substituted or unsubstituted C2-C30 heteroarylene, a substituted or unsubstituted C3-C15 alicyclic and a C6-C30 aromatic ring fused cycloalgide. The condition is that Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L, L1, L2, L3, L4, L5, L6, L a L b L c At least one of them contains one or more groups represented by Formula II: The R a R b R c It is independently selected from one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 alicyclic, substituted or unsubstituted C6-C30 aryl, fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic, substituted or unsubstituted C2-C30 heteroaryl, and fused cycloalcoholic group of substituted or unsubstituted C3-C15 alicyclic and C2-C30 heteroaryl.

2. The triarylamine compound according to claim 1, characterized in that, The L is selected from any one of the following groups: R1 is selected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, furanyl, benzofuranyl The following groups are included: uranyl, dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, acridineyl, o-phenanthrolineyl, and groups shown in Formula II; or two adjacent R1 groups may be interconnected to form substituted or unsubstituted benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, pyridyl rings, pyrimidinyl rings, quinolinyl rings, isoquinolinyl rings, quinazolinyl rings, quinoxalinyl rings, or C3-C8 aliphatic rings; R2, R3, R7, and R8 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and the group shown in Formula II; or any one of R2 and R3 can be directly reacted with L. a L b L c Any one of the bonds in; R4 and R9 are independently 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, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or R4 can be directly substituted with L a L b L c Any one of the bonds in; a1 is selected from 0, 1, 2 or 3; a2 is selected from 0, 1, 2, 3 or 4; a3 is selected from 0, 1 or 2; a4 is selected from 0 or 1; when there are two or more R1s, the two or more R1s are the same as or different from each other.

3. The triarylamine compound according to claim 1, characterized in that, At least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contains one or more groups represented by Formula II.

4. The triarylamine compound according to claim 1, characterized in that, Formula II is selected from any one of the following groups: .

5. The triarylamine compound according to claim 1, characterized in that, The Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 groups are independently selected from one of the following groups: The y may be selected from N or CH, either the same or different. The ring A is selected from substituted or unsubstituted C3 to C10 aliphatic rings; Y3 and Y4 are independently selected from single bonds, O, S, and N(R). d ), C(R e R f One of them; The Y5 is selected from O, S, N(R) g ), C(R h R i One of the following; the Y6 is selected from N or CH; The R5 groups are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, pyrene, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or two adjacent R5 groups may be connected to each other to form substituted or unsubstituted rings; The R d R g Selected, either identically or differently, 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, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or the group shown in Formula II; or the R group. d R g It can directly bond with any one of L1, L2, L3, L4, L5, and L6; The R e R f R h R i Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, or the group shown in Formula II; or R e R f They can connect to each other to form substituted or unsubstituted rings; or R e R f Any one of them can be directly bonded to any one of L1, L2, L3, L4, L5, and L6; The b1 is selected from 0, 1, 2, 3, 4 or 5; the b2 is selected from 0, 1, 2, 3, 4, 5, 6 or 7; the b3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9; the b4 is selected from 0, 1, 2, 3 or 4; the b5 is selected from 0, 1, 2 or 3; when there are two or more R5s, the two or more R5s are the same as or different from each other.

6. The triarylamine compound according to claim 1, characterized in that, L1, L2, L3, L4, L5, L6, L a L b L c Independently selected from a single bond or one of the following groups: The z may be selected from N or CH, either the same or different. The ring B is selected from substituted or unsubstituted C3 to C10 aliphatic rings; E is selected from O, S, N(R) j ), C(R k R l One of them; The R6 groups are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and groups shown in Formula II; or two adjacent R6 groups may be linked together to form substituted or unsubstituted rings; The R j 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, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazoyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl; or R j It can be directly bonded to any one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6; The R k R l Independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one 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, phenylenetriphenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazole, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, or the group shown in Formula II; or R k R l They can connect to each other to form substituted or unsubstituted rings; or R k R l Any one of them can be directly bonded to any one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6; c1 is selected from 0, 1, 2, 3 or 4; c2 is selected from 0, 1, 2 or 3; c3 is selected from 0, 1 or 2; when there are two or more R6, the two or more R6 are the same or different from each other.

7. The triarylamine compound according to claim 1, characterized in that, The triarylamine compound is selected from one of the following structures: 。 8. 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 one or more 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 described in any one of claims 1 to 7.

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

10. An organic electroluminescent device according to claim 8, wherein the organic layer is located outside one or more electrodes of the anode and the cathode, characterized in that, The organic layer includes a capping layer containing any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.

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