A triarylamine compound and an organic electroluminescent device thereof

Abstract

The application provides a triarylamine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The triarylamine compound has high hole mobility and electron blocking performance, and can improve the injection and transmission efficiency of holes;when the triarylamine compound is applied to a hole transport region in an organic electroluminescent device, the luminous efficiency and service life of the device can be effectively improved;simultaneously, the triarylamine compound also has high light extraction efficiency;when the triarylamine compound is applied to a cover layer in an organic electroluminescent device, the luminous efficiency and service life of the organic electroluminescent device are improved;the preparation method of the organic compound is simple, raw materials are easy to obtain, the organic compound can be widely applied to the fields of panel display, illumination light source, organic solar cell, organic photoreceptor or organic thin film transistor, and has good application effect and industrialization prospect.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs, or organic electroluminescent devices) are a class of self-emissive electronic devices that convert electrical energy into light energy. They have advantages such as higher contrast, wider viewing angle, and faster response time, and can be fabricated into various forms such as rollable and bendable products on flexible substrates. In recent years, they have received widespread attention from academia and industry.

[0003] In OLEDs, under the influence of an applied electric field, electrons from the cathode and holes from the anode recombine in the organic layer, releasing energy and transferring it to the organic light-emitting compound. This causes the compound to transition from its ground state to an excited state. The excited molecules then return to their ground state, releasing energy in the form of light, thus producing the luminescence phenomenon. OLEDs have a sandwich-like structure, typically consisting of an anode, a cathode, and an organic layer. Currently, the organic layers involved in OLEDs include hole injection layers, hole transport layers, hole blocking layers, light-emitting layers, electron blocking layers, electron transport layers, electron injection layers, and capping layers.

[0004] As one of the most important functional layers in OLED devices, the hole transport layer's fundamental function is to improve the hole transport efficiency within the device and effectively block electrons within the emissive layer, achieving maximum carrier recombination. Simultaneously, when multiple layers exist, appropriate highest occupied molecular orbitals (HOMO) and triplet energy levels (T1) are required to achieve high matching between layers, including the emissive layer. However, the types of hole transport materials currently used in industry are limited, and they generally suffer from low luminous efficiency and short lifespan. Therefore, developing hole transport materials with suitable HOMO orbital energy levels, high hole mobility, and improved thermal stability and film-forming properties through structural adjustments is an urgent task. On the other hand, due to waveguide effects, light inside the device experiences increased total internal reflection, reducing its internal light extraction efficiency. In recent years, to improve light extraction efficiency and color shift, a high-refractive-index "capping layer" material is typically placed outside the low-refractive-index semi-transparent electrode to improve OLED device performance.

[0005] To address the aforementioned issues, the development of hole transport materials with high hole mobility, high glass transition temperature, and suitable triplet energy levels, as well as capping materials with high light extraction efficiency, has become an urgent problem to be solved. Summary of the Invention

[0006] To address the problems existing in the prior art, this invention provides a triarylamine compound and its organic electroluminescent device. Applying the triarylamine compound provided by this invention to the hole transport region or capping layer can develop organic electroluminescent devices with high efficiency and long lifetime, solving the problems of low luminous efficiency and short lifespan in existing organic electroluminescent devices. It has the general formula shown in Formula 1.

[0007]

[0008] The Ar1 is selected from substituted or unsubstituted C1-C15 alkyl groups or substituted or unsubstituted silyl groups;

[0009] The x is selected from N or CH; the x at the bonding site is selected from C;

[0010] The Ar2 is selected from formula 2.

[0011]

[0012] The Y1 is selected from O, S or N (R5);

[0013] The y is selected from N or CH; the y at the bonding site is selected from C;

[0014] The Ar3 is selected from Formula 2 or any one of the following groups:

[0015]

[0016] Y2 and Y4 are selected from O, S, or C(R) whether they are the same or different. b R c The Y3 is selected from O, S, or N(R). d );

[0017] The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0018] The z is selected from N or CH; the z at the bonding site is selected from C;

[0019] The R1, R2, R3, R4, R6, R b R c The same or different from any one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and combinations thereof; or between two adjacent R1s, two R2s, two R4s, two R6s, R b and Rc They can connect with each other to form substituted or unsubstituted rings;

[0020] a is selected from 1, 2, 3, or 4; b is selected from 1, 2, 3, or 4; c is selected from 1 or 2; d is selected from 1, 2, 3, or 4;

[0021] f1 is selected from 1, 2, 3, 4 or 5; f2 is selected from 1, 2, 3, 4, 5, 6 or 7; f3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; f4 is selected from 1, 2, 3 or 4; f5 is selected from 1 or 2; f6 is selected from 1, 2 or 3.

[0022] The R5, R d The same or different are selected from any one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and combinations thereof;

[0023] The L1 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0024] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0025] 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 the triarylamine compound described in the present invention.

[0026] Beneficial effects:

[0027] This invention discloses a triarylamine compound as shown in Formula 1 and its organic electroluminescent device. The triarylamine compound has high hole mobility and electron blocking performance, which can improve hole injection and transport efficiency. When applied to the hole transport region in an organic electroluminescent device, it can effectively improve the luminous efficiency and lifespan of the device. At the same time, the triarylamine compound also has a high refractive index. When applied to the capping layer in an organic electroluminescent device, it can reduce total internal reflection and waveguide loss of light inside the device, enhance the light extraction efficiency of the device, and thus improve the luminous efficiency of the organic electroluminescent device. Detailed Implementation

[0028] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0029] 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.

[0030] Examples of halogens described in this invention may include fluorine atoms, chlorine atoms, bromine atoms, or iodine atoms.

[0031] In this invention, "C1-C15" in "substituted or unsubstituted C1-C15 alkyl groups" refers to the number of carbon atoms in the unsubstituted alkyl group, excluding the number of carbon atoms in the substituents. Similarly, "C3-C15" in "substituted or unsubstituted C3-C15 cycloalkyl groups" refers to the number of carbon atoms in the unsubstituted cycloalkyl group, excluding the number of carbon atoms in the substituents. And so on.

[0032] The alkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from an alkane molecule. The alkyl group has 1 to 15 carbon atoms, preferably 1 to 10. Examples of alkyl groups include, but are not limited to, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, etc.

[0033] The chain alkyl groups with more than three carbon atoms described in this invention include their isomers. For example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, sec-butyl, isobutyl, and tert-butyl. And so on.

[0034] The alicyclic group described in this invention refers to an aliphatic hydrocarbon having 3 to 15 carbon atoms, which can be completely unsaturated or partially unsaturated. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, and cycloheptene, but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure.

[0035] The cycloalkyl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from a cycloalkane molecule. The cycloalkyl group has 3 to 15 carbon atoms, preferably 3 to 10. Examples of cycloalkyl groups include, but are not limited to, the following groups: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, adamantyl, camphenyl, norbornyl, ferruginyl, isocamphenyl, etc.

[0036] The aryl group described in this invention refers to a monovalent group formed by removing one hydrogen atom from the aromatic carbon atom of an aromatic hydrocarbon molecule. The aryl group includes monocyclic aryl, polycyclic aryl, and fused-ring aryl groups. The number of carbon atoms in the aryl group is C6 to C30, preferably C6 to C20, more preferably C6 to C15, and even more preferably C6 to C12. Examples of the aryl group include, but are not limited to, the following groups: phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, naphthyl, indene, dihydroindene, dihydronaphthyl, tetrahydronaphthyl, phenanthrene, triphenylene, anthracene, pyrene, fluorenyl, spirodifluorenyl, spiroanthracenefluorenyl, benzo[a]fluorenyl, benzo[a]spirodifluorenyl, etc.

[0037] The heteroaryl group described in this invention refers to a monovalent group in which at least one aromatic carbon atom is replaced by a heteroatom. The heteroaryl group has 2 to 30 carbon atoms, preferably 2 to 15, and even more preferably 2 to 10. The heteroatom includes, but is not limited to, the atoms listed below: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl and fused-ring heteroaryl groups. Examples of heteroaryl groups include, but are not limited to, the groups listed below: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, furanyl, benzofuranyl, dibenzofuranyl, benzodibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, benzodibenzothiophene, carbazole, etc.

[0038] The "substituted or unsubstituted silyl group" mentioned in this invention refers to —Si(R k )3 groups, wherein each R kThe same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C6-C60 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C30 alicyclic and C2-C60 heteroaryl rings. Preferably, each R k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The alkyl group preferably has 1 to 20 carbon atoms, more preferably 1 to 15, even more preferably 1 to 10, and most preferably 1 to 8. The cycloalkyl group preferably has 3 to 20 carbon atoms, more preferably 3 to 15, even more preferably 3 to 10, and most preferably 3 to 7. The aryl group preferably has 6 to 20 carbon atoms, more preferably 6 to 13, even more preferably 6 to 12, and most preferably 6 to 10. Preferably, each R... k The same or different groups are selected from the following: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornel, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl. The term "alkylsilyl" refers to at least one substituent R of a silyl (-SiH3) group. k It is an alkyl group, and the preferred alkylsilyl groups specifically include trimethylsilyl, triethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl, but are not limited thereto; the "arylsilyl" refers to at least one substituent R of the alkyl (-SiH3) group. k It is an aryl group, and preferred arylsilyl groups include triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are not limited to these.

[0039] The fused alicyclic and aromatic ring groups described in this invention refer to rings containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic rings preferably have 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic rings preferably have 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0040] The arylene group described in this invention refers to a divalent group formed by removing two hydrogen atoms from the aromatic carbon atom in an aromatic hydrocarbon molecule. The arylene group has a carbon number of C6 to C30, preferably C6 to C20, and even more preferably C6 to C10. The arylene group includes monocyclic arylene, polycyclic arylene, fused-ring arylene, or combinations thereof. Examples of arylene groups include, but are not limited to, the following groups: phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, triphenylene, perylene, pyrene, indene, fluorene, benzo[a]fluorene, dibenzo[a]fluorene, spirodifluorene, benzo[a]spirodifluorene, etc.

[0041] The heteroaryl group described in this invention refers to a divalent group in which at least one carbon atom of the aryl group is replaced by a heteroatom. The number of carbon atoms in the heteroaryl group is C2 to C30, preferably C2 to C20, and even more preferably C2 to C10. The heteroatom includes, but is not limited to, the following atoms: O, S, N, Si, B, P, etc. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of heteroaryl groups include, but are not limited to, the following groups: pyridylene, pyrimidinylene, quinolineylene, isoquinolineylene, furanylene, benzofuranylene, dibenzofuranylene, benzodibenzofuranylene, thiophenylene, benzothiophenylene, dibenzothiophenylene, benzodibenzothiophenylene, etc.

[0042] In the "substituted or unsubstituted" of this invention, "unsubstituted" means that the hydrogen atom on the group is not replaced by any substituent, and "substituted" means that at least one hydrogen atom on the group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different, and the position of the hydrogen atoms replaced by the substituents may be arbitrary.

[0043] The substituted group represented by "substituted or unsubstituted" in the above-mentioned terms is selected from one of the following groups: deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and fused alicyclic and aromatic ring groups. For example, the following groups are preferred: deuterium, halogen atom, cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, undecyl, dodecyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, adamantyl, camphenyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyrene, fluorenyl, 9,9-dimethylfluorenyl, 9 ,9-Diphenylfluorenyl, benzo[fluorenyl], dibenzo[fluorenyl], spirodifluorenyl, benzo[spirodifluorenyl], dibenzofuranyl, benzo[dibenzofuranyl], dibenzothiopheneyl, benzo[dibenzothiopheneyl], benzo[cyclopropane], benzo[cyclobutane], dihydroindyl, tetrahydronaphthyl, benzo[cycloheptane], benzo[cyclooctyl], indyl, dihydronaphthyl, etc., but not limited to these, and the above substituents can be unsubstituted, partially substituted with deuterium, or completely substituted with deuterium.

[0044] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent Can represent And so on.

[0045] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent Can represent Can represent And so on.

[0046] In this invention, "adjacent groups can connect with each other to form substituted or unsubstituted rings" refers to the formation of substituted or unsubstituted hydrocarbon rings or substituted or unsubstituted heterocycles by the combination of adjacent groups and optional aromatization. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. Examples are shown below:

[0047]

[0048] In this invention, the ring formed by the connection can be a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, phenanthrene, triphenylene, cyclopentane, cyclohexane, cyclopentene, cyclohexene, fluorene, pyridine, pyrimidine, dibenzofuran, dibenzothiophene, but not limited thereto.

[0049] This invention provides a triarylamine compound having the general structural formula shown in Formula 1.

[0050]

[0051] The Ar1 is selected from substituted or unsubstituted C1-C15 alkyl groups or substituted or unsubstituted silyl groups;

[0052] The x is selected from N or CH; the x at the bonding site is selected from C;

[0053] The Ar2 is selected from formula 2.

[0054]

[0055] The Y1 is selected from O, S or N (R5);

[0056] The y is selected from N or CH; the y at the bonding site is selected from C;

[0057] The Ar3 is selected from Formula 2 or any one of the following groups:

[0058]

[0059] Y2 and Y4 are selected from O, S, or C(R) whether they are the same or different. b R c The Y3 is selected from O, S, or N(R). d );

[0060] The ring A is selected from substituted or unsubstituted C3-C15 alicyclic groups;

[0061] The z is selected from N or CH; the z at the bonding site is selected from C;

[0062] The R1, R2, R3, R4, R6, R b R c The same or different from any one of hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and combinations thereof; or between two adjacent R1s, two R2s, two R4s, two R6s, R b and R c They can connect with each other to form substituted or unsubstituted rings;

[0063] a is selected from 1, 2, 3, or 4; b is selected from 1, 2, 3, or 4; c is selected from 1 or 2; d is selected from 1, 2, 3, or 4; f1 is selected from 1, 2, 3, 4, or 5; f2 is selected from 1, 2, 3, 4, 5, 6, or 7; f3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; f4 is selected from 1, 2, 3, or 4; f5 is selected from 1 or 2; f6 is selected from 1, 2, or 3.

[0064] The R5, R d The same or different are selected from any one of the following: substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, fused cycloalcohols of substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, substituted or unsubstituted C2-C30 heteroaryl, and combinations thereof;

[0065] The L1 is selected from any one of the following: substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0066] L2 and L3 are independently selected from any one of the following: single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C15 alicyclic and C6-C30 aromatic rings, and combinations thereof.

[0067] Preferably, in Formula 1 Selected from any one of the following groups:

[0068]

[0069]

[0070] R1 and R2 are independently selected from deuterium, tritium, cyano, halogen, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, indene, fluorenyl, benzofuranyl, Any one of the following: dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof; or the two adjacent R1s or the two R2s may be interconnected to form substituted or unsubstituted rings;

[0071] a1 is selected from 1, 2, 3, or 4; a2 is selected from 1, 2, 3, 4, 5, or 6; a3 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; a4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; a5 is selected from 1, 2, or 3; b1 is selected from 1, 2, 3, or 4; b2 is selected from 1, 2, 3, 4, 5, or 6; b3 is selected from 1, 2, or 3; b4 is selected from 1 or 2.

[0072] Preferably, the Ar2 is selected from any one of the following groups derived from Formula 2:

[0073]

[0074] R3 and R4 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, indene, fluorenyl, benzo[…]. Furanyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tritert-butylsilyl, triphenylsilyl, and combinations thereof; or the two adjacent R4s may be interconnected to form substituted or unsubstituted rings;

[0075] c1 is selected from 1 or 2; d1 is selected from 1, 2, 3 or 4; d2 is selected from 1, 2, 3, 4, 5 or 6; d3 is selected from 1 or 2; d4 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; d5 is selected from 1, 2, 3, 4, 5, 6 or 7.

[0076] More preferably, the Ar2 is selected from any one of the following groups derived from Formula 2:

[0077]

[0078]

[0079] R3 and R4 are independently selected from hydrogen, deuterium, cyano, halogen, nitro, and the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornel, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl Trimethylsilyl, triethylsilyl, triphenylsilyl, and combinations thereof; wherein the substituent in the “substituted or unsubstituted” is selected from one or more of deuterium, cyano, halogen, trifluoromethyl, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, deuterated phenyl, biphenyl, and naphthyl; in the case of being substituted by multiple substituents, the multiple substituents are the same or different from each other; or the two adjacent R4s can be interconnected to form a substituted or unsubstituted benzene ring;

[0080] The R a The group is selected from the following groups, whether 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, benzocyclopentenyl, benzocyclohexenyl, indole, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzoimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof;

[0081] The d6 is selected from 1, 2, 3, 4 or 5; the d7 is selected from 1, 2 or 3.

[0082] Preferably, the Ar3 is selected from Formula 2 or any one of the following groups:

[0083]

[0084]

[0085] The R6, R b R c R eThe group independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriethylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclopentenyl, benzocyclocyclohexane Hexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof; or between two adjacent R6 groups, R b With R c They can connect with each other to form substituted or unsubstituted rings;

[0086] The R d The group is selected from the following groups, whether 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, benzocyclopentenyl, benzocyclohexenyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof;

[0087] f7 is selected from 1, 2, 3, 4, 5, or 6; f8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; f9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R6, R b R c R d R e At that time, two or more R6, R b R c R d R e They may be the same as or different from each other.

[0088] More preferably, the Ar3 is selected from Formula 2 or any one of the following groups:

[0089]

[0090]

[0091] R6 is selected, either identically or differently, from hydrogen, deuterium, cyano, halogen, nitro, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, benzocyclopentyl, benzocyclohexyl, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzooxazolyl, benzothiazolyl, benzimidazolyl, indole, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, triphenyl ... The substituent is selected from one or more of methylsilyl, triphenylsilyl, and combinations thereof, wherein the substituent in the "substituted or unsubstituted" group is selected from deuterium, cyano, halogen, trifluoromethyl, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, phenyl, deuterated phenyl, biphenyl, and naphthyl. In the case of substitution by multiple substituents, the multiple substituents are the same or different from each other; or the two adjacent R6 groups can be interconnected to form a substituted or unsubstituted ring.

[0092] Preferably, L1 is selected from any one of the following groups and combinations thereof:

[0093]

[0094]

[0095] The R7, R f R g The group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantane, norbornene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof;

[0096] The R hSelected from the following groups, whether 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, fluorenyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof;

[0097] The R i The following groups are selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, 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, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and combinations thereof;

[0098] The g1 is selected from 1, 2, 3, or 4; the g2 is selected from 1, 2, or 3; the g3 is selected from 1 or 2; the g4 is selected from 1, 2, 3, 4, 5, or 6; the g5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the g6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R7, R i At that time, two or more R7, R i They may be the same as or different from each other.

[0099] Preferably, L2 and L3 are selected from single bonds or any one of the following groups and combinations thereof:

[0100]

[0101] The R8, R j R kThe group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, trifluoromethyl, and any 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, phenylenetriethylene, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triphenylsilyl, and any combination thereof;

[0102] The R m The group is selected from hydrogen, deuterium, tritium, cyano, halogen, nitro, trifluoromethyl, and any 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, phenylenetriphenyl, fluorene, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, and combinations thereof.

[0103] h1 is selected from 1, 2, 3, or 4; h2 is selected from 1, 2, or 3; h3 is selected from 1 or 2; h4 is selected from 1, 2, 3, 4, 5, or 6; h5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; h6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R8, R m At that time, two or more R8, R m They may be the same as or different from each other.

[0104] More preferably, L1 is selected from any one of the following groups and combinations thereof, and L2 and L3 are selected from single bonds or any one of the following groups and combinations thereof:

[0105]

[0106] Most preferably, the triarylamine compound represented by structural formula 1 is selected from one of the structures shown below.

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] The above lists some specific chemical structures of the triarylamine compounds of structural formula 1 of the present invention. However, the present invention is not limited to these listed chemical structures. All compounds based on the triarylamine compounds of structural formula 1 with substituents as defined above should be included.

[0128] Furthermore, the present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds represented by Formula 1 of the present invention.

[0129] Preferably, the organic layer includes a hole transport region or a capping layer, the hole transport region being located between the anode and the cathode, the capping layer being located outside at least one of the electrodes of the anode and the cathode, and at least one of the hole transport region or capping layer containing any one or a combination of at least two of the triarylamine compounds of Formula 1 as described in this invention.

[0130] Preferably, the organic layer includes a hole transport region containing the triarylamine compound described in this invention.

[0131] Preferably, the hole transport region includes at least one of a hole injection layer and a hole transport layer, wherein the hole injection layer is located between the anode and the cathode, and the hole transport layer is located between the hole injection layer and the cathode, and at least one of the hole injection layer and the hole transport layer contains the triarylamine compound described in this invention.

[0132] Preferably, the hole transport region includes a hole transport layer, and the hole transport layer contains the triarylamine compound described in this invention.

[0133] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the second hole transport layer is located between the first hole transport layer and the cathode, and the third hole transport layer is located between the second hole transport layer and the cathode, and at least one of the first hole transport layer, the second hole transport layer, and the third hole transport layer contains the triarylamine compound described in this invention.

[0134] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the second hole transport layer containing the triarylamine compound described in this invention.

[0135] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the first hole transport layer containing the triarylamine compound described in this invention.

[0136] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer, the second hole transport layer being located between the first hole transport layer and the cathode, and the first hole transport layer and the second hole transport layer containing the triarylamine compound described in this invention.

[0137] Preferably, the organic layer includes a cover layer on the side of the cathode opposite to the anode, and the cover layer contains one or more of the triarylamine compounds described in this invention.

[0138] The organic electroluminescent device of the present invention is typically formed on a substrate. The substrate need not change during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0139] 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 layers and electrodes on both sides of the aforementioned organic electroluminescent device are described below:

[0140] The anode of this invention preferably uses a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically above 4.0 eV). The materials used for the anode in this invention can include: metals or their alloys, metal oxides, multilayer materials, conductive polymers, combinations of metals and oxides, etc., for example, nickel (Ni), platinum (Pt), vanadium (V), silver (Ag), gold (Au), zinc oxide (ZnO), indium tin oxide (ITO), indium zinc oxide (IZO), indium oxide (In₂O₃), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polypyrrole, polyaniline, zinc oxide:aluminum (ZnO:Al), etc., but are not limited to these.

[0141] The cathode of this invention preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work function (specifically below 3.8 eV). The materials used for the cathode in this invention may include: metals or their alloys, multilayer materials, etc., such as silver (Ag), aluminum (Al), magnesium (Mg), tin (Sb), magnesium silver (Mg:Ag), calcium / magnesium (Ca / Mg), etc., but are not limited thereto.

[0142] The hole injection material described in this invention is preferably a material capable of reducing the interfacial barrier between the anode and the hole transport layer. Materials such as those described below include polycyano-conjugated organic compounds, axial alkene compounds, phthalocyanine metal complexes, aromatic amine derivatives, and polymers. Specific examples may include, but are not limited to, 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazabenzphenanthrene (HAT-CN), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanodimethyl-p-benzoquinone (F4-TCNQ), 2,2',2''-(cyclopropane-1,2,3-tripyridyl)-tris(2-perfluorophenylacetonitrile), copper phthalocyanine (CuPC), N4,N4'-(biphenyl-4,4'-diacyl)bis(N4,N4',N4'-triphenylbiphenyl-4,4'-diamine) (TPT1), N,N-phenyl-N,N-(9-phenyl-3-carbazolyl)-1,1'-biphenyl-4,4'-diamine, poly(3,4-ethylenedioxythiophene) (PEDOT) / poly(styrenesulfonic acid) (PSS), etc.

[0143] The hole transport material described in this invention preferably possesses good hole transport capability and good stability. The hole transport material described in this invention is located between the anode and the light-emitting layer, or, in the presence of a hole injection layer, between the hole injection layer and the light-emitting layer. The inventive compound can be used alone or in combination with the compounds described below in the hole transport layer.

[0144] Other hole transport layer materials besides the compounds of this invention can be, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, polymers, etc. Specific examples may include N-([1,1'-biphenyl]-4-yl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)dibenzo[b,d]furan-4-amine, N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), N,N'-diphenyl-N,N'-di(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N4,N4-di([1,1'-biphenyl]-4-yl)-N4'-([1,1':4',1”-terphenyl]-4-yl) The following compounds are permitted, but are not limited to: 1,1'-biphenyl]-4,4'-diamine, N,N,N',N'-tetraphenylbiphenyldiamine, 9,9'-diphenyl-6-(9-phenyl-9H-carbazole-3-yl)-9H,4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (t-BuDNA), 9,10-di(2-naphthyl)anthracene (DNA), and 9,10-diphenylanthracene (DPAnth), p-phenylenevinylene (PPV), etc. Preferably, triarylamine compounds of Formula 1 of the present invention are preferred.

[0145] The light-emitting layer described in this invention may contain only the guest material, or it may be in the form of the guest material being dispersed in the host material, wherein the host material may be composed of one or more materials.

[0146] The main material of the light-emitting layer of the present invention may include fused aromatic ring derivatives, heterocyclic compounds, etc., such as 9,10-bis(2-naphthyl)anthracene (ADN), 10,10'-bis(biphenyl-4-yl)-9,9'-bianthracene (BANE), 1,3,5-tris(pyrene-1-yl)benzene (TPB3), 1,3,5-tris(carbazole-9-yl)benzene (TCP), 14,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl (CDBP), 4,4'-bis(carbazole-9-yl)biphenyl (CBP), etc., but is not limited thereto.

[0147] As guest materials for the luminescent layer of the present invention, they may include aromatic amine derivatives, fused aromatic ring derivatives, heterocyclic derivatives, metal complexes, etc., such as 4,4'-bis(4-(9H-carbazole-9-yl)styryl)biphenyl (BSB4), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAVBi), 10,10'-bis(3,5-bis(trifluoromethyl)phenyl)-9,9'-bianthracene (Ban-(3,5)-CF3), 5,6,11,12-tetraphenylbenzotetraphenyl (Rubrene), coumarin 545T (C-525T)tris(2-phenyl-3-methylpyridine)iridium (Ir(3mppy)3), bis(2-(naphthyl-2-yl)pyridine)(acetylacetone)iridium(III)(Ir(npy)2acac), tris(2-phenylpyridine)iridium(III)(Ir(ppy)3), etc., but are not limited thereto.

[0148] The hole-blocking layer material described in this invention needs to have good hole-blocking ability in order to block holes within the light-emitting layer. Materials such as imidazole derivatives, phenanthroline derivatives, metal complexes, and triazine derivatives are examples. Specific examples may include, but are not limited to, 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi), 2-(naphth-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 4,7-diphenyl-1,10-phenanthroline (Bphen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), di(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 2-(9,9-dimethyl-9H-fluorene-2-yl)4-(9,9-diphenyl-9H-fluorene-4-yl)-6-phenyl-1,3,5-triazine, etc.

[0149] The electron transport layer material described in this invention preferably possesses good electron transport capability and good stability. Materials such as imidazole derivatives, phenanthroline derivatives, pyridine derivatives, triazine derivatives, quinoline derivatives, oxadiazole derivatives, triazole derivatives, and metal complexes are included. Specific examples may include 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazolium, 2-(naphthyl-2-yl)-4,7-diphenyl-1,10-phenanthroline (HNBphen), 2,9-(dimethyl)-4,7-biphenyl-1,10-o-phenanthroline (BCP), 3,3'-[5'-[3-(3-pyridyl)phenyl](TmPyPB), 1,4-bis(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalene, 2-(3-(phenanthroline-9-)... 1,3,5-triazine (-yl)-5-(pyridin-3-yl)phenyl)-4,6-diphenyl-1,3,5-triazine, 1,3,5-tris(4-(pyridin-4-yl)quinoline-2-yl)benzene (TPyQB), 2,5-di-(4-naphthyl)-1,3,4-oxadiazole (BND), 3-(biphenyl-4-yl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ), di(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (BAlq), lithium 8-hydroxyquinoline (LiQ), etc., but not limited to these.

[0150] The electron blocking layer of this invention preferably uses a material whose absolute value of the difference between the HOMO value of the electron blocking layer and that of the hole transport layer is greater than or equal to 0.07 eV and less than or equal to 0.35 eV. Specific examples may include triarylamine compounds, spirofluorene derivatives, furan derivatives, etc., such as TPD, NPB, N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenylN4'-[1,1':4',1”] The following are examples of amino acids and compounds, but not limited to: [[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9'-spirodifluorene-2-amine, N,N-di([1,1'-biphenyl]-4-yl)-3'-(dibenzo[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, etc.

[0151] The electron injection layer material described in this invention is preferably a material capable of reducing the interfacial barrier between the cathode and the electron transport layer. Alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple such compounds can be used in combination.

[0152] The capping layer described in this invention can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. The capping layer material can be an organic or inorganic substance with an appropriate refractive index, such as metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc. Specific examples may include LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, tris(8-hydroxyquinoline)aluminum(III) (Alq3), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4'-di(9-carbazole)biphenyl (abbreviated CBP), and the triaromatic amine compounds described in this invention, but are not limited thereto.

[0153] 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, etc. can be used, but are not limited to these methods.

[0154] The organic electroluminescent device of this invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, flat-screen TVs, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, etc.

[0155] Synthesis Examples

[0156] Raw materials and reagents: This invention does not impose any particular limitations 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. All raw materials and reagents used in this invention are of reagent purity.

[0157] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); Vario ELcube organic elemental analyzer (Elementar Corporation, Germany).

[0158] There are no particular limitations on the preparation method of the triarylamine compounds of structural formula 1 of the present invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-nitrogen coupling reaction, carbon-carbon coupling reaction, etc. For example, the triarylamine compounds of structural formula 1 of the present invention can be prepared by the synthetic route shown below.

[0159]

[0160] X1 and X2 are halogen atoms, for example, they may be the same or different halogen atoms selected from the following: I, Br, Cl.

[0161] Synthesis Examples

[0162] Synthesis Example 1: Synthesis of Intermediate A-60

[0163]

[0164] Preparation of intermediate A-60:

[0165] Under argon protection, a-60 (19.08 g, 70.00 mmol), b-60 (18.14 g, 70.00 mmol), potassium carbonate (12.58 g, 91.00 mmol), Pd(PPh3)4 (0.97 g, 0.84 mmol), and 350 mL of a toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 4.5 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out under cooling and filtered. The resulting solid was recrystallized from toluene to obtain intermediate A-60 (22.50 g, yield 79%); HPLC purity ≥ 99.71%. Mass spectrometry m / z: 406.1475 (theoretical value: 406.1488).

[0166] Following the above synthesis method, other intermediates A- required for the present invention were synthesized, and the relevant raw materials are shown in Table 101:

[0167] Table 101:

[0168]

[0169]

[0170] Synthesis Example 2: Synthesis of Compound 19

[0171]

[0172] Preparation of intermediate B-19:

[0173] Under argon protection, c-19 (6.25 g, 40.00 mmol), d-19 (7.88 g, 40.00 mmol), potassium carbonate (7.19 g, 52.00 mmol), Pd(PPh3)4 (0.55 g, 0.48 mmol), and 200 mL of a toluene / ethanol / water (2:1:1) mixed solvent were added to a reaction flask. The mixture was stirred and the reaction system was heated under reflux for 3.5 h. After the reaction was completed, the mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried with anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. Crystallization was carried out by cooling and filtration. The obtained solid was recrystallized from toluene to obtain intermediate B-19 (7.68 g, yield 84%); HPLC purity ≥ 99.79%. Mass spectrometry m / z: 228.0353 (theoretical value: 228.0342).

[0174] Preparation of intermediate I-19:

[0175] Under nitrogen protection, e-19 (17.58 g, 50.00 mmol), a-19 (16.76 g, 50.00 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), Pd(OAc)2 (0.13 g, 0.60 mmol), and 300 mL of toluene were added sequentially to the reaction flask. The air was then purged with nitrogen three times. Tri-tert-butylphosphine (1.20 mL, 0.50 M in toluene solution) was then added, and the mixture was stirred. The reaction was carried out under reflux for 5 h. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was recrystallized from toluene:ethanol (8:1) to obtain intermediate I-19 (23.63 g, 78%). The purity of the solid was determined by HPLC to be ≥99.85%. Mass spectrometry m / z: 605.2531 (theoretical value: 605.2539).

[0176] Preparation of compound 5:

[0177] Under nitrogen protection, intermediates I-19 (18.18 g, 30.00 mmol), B-19 (6.86 g, 30.00 mmol), sodium tert-butoxide (5.77 g, 60.00 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), and X-phos (0.29 g, 0.60 mmol), along with 150 mL of toluene, were added sequentially to a reaction flask. The mixture was stirred at reflux for 6.5 h. After the reaction was complete, the reaction solution was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand and separated, and the organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. The mixture was recrystallized from toluene to give compound 19 (17.72 g, 74%). The purity of the solid was ≥99.96% as determined by HPLC. Mass spectrometry m / z: 797.3129 (theoretical value: 797.3114). Theoretical elemental content (%) C 58 H 43 NOSi: C, 87.29; H, 5.43; N, 1.76. Measured elemental content (%): C, 87.31; H, 5.42; N, 1.73.

[0178] Synthesis Example 3: Preparation of Compound 25

[0179]

[0180] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-25, and e-19 was replaced with an equimolar amount of e-25, yielding compound 25 (14.22 g, yield 77%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 615.2575 (theoretical value: 615.2562). Theoretical elemental content (%) C 46 H 33 NO: C, 89.73; H, 5.40; N, 2.27. Measured elemental content (%): C, 89.71; H, 5.38; N, 2.30.

[0181] Synthesis Example 4: Preparation of Compound 42

[0182]

[0183] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-42 and d-42, respectively, and e-19 was replaced with equimolar amounts of e-42, yielding compound 42 (14.36 g, yield 76%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 629.2710 (theoretical value: 629.2719). Theoretical elemental content (%) C 47 H 35NO: C, 89.63; H, 5.60; N, 2.22. Measured elemental content (%): C, 89.65; H, 5.58; N, 2.25.

[0184] Synthesis Example 5: Preparation of Compound 54

[0185]

[0186] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-54, and e-19 was replaced with an equimolar amount of e-54, yielding compound 54 (15.48 g, yield 75%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 687.2973 (theoretical value: 687.2957). Theoretical elemental content (%) C 49 H 41 NOSi: C, 85.55; H, 6.01; N, 2.04. Measured elemental content (%): C, 85.58; H, 6.02; N, 2.01.

[0187] Synthesis Example 6: Preparation of Compound 60

[0188]

[0189] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-60, and e-19 and a-19 were replaced with equimolar amounts of e-60 and A-60, respectively, to obtain compound 60 (17.17 g, yield 72%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 794.4295 (theoretical value: 794.4284). Theoretical elemental content (%) C 59 H 46 D5NO: C, 89.13; H, 7.10; N, 1.76. Measured elemental content (%): C, 89.16; H, 7.08; N, 1.77.

[0190] Synthesis Example 7: Preparation of Compound 69

[0191]

[0192] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-69 and d-69, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-69 and A-69, respectively, to obtain compound 69 (17.25 g, yield 71%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 809.3641 (theoretical value: 809.3658). Theoretical elemental content (%) C 61 H 47NO: C, 90.45; H, 5.85; N, 1.73. Measured elemental content (%): C, 90.43; H, 5.86; N, 1.72.

[0193] Synthesis Example 8: Preparation of Compound 85

[0194]

[0195] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-85, and e-19 and a-19 were replaced with equimolar amounts of e-85 and A-85, respectively, to obtain compound 85 (15.66 g, yield 75%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 695.3113 (theoretical value: 695.3126). Theoretical elemental content (%) C 52 H 33 D4NO: C, 89.75; H, 5.94; N, 2.01. Measured elemental content (%): C, 89.77; H, 5.91; N, 2.03.

[0196] Synthesis Example 9: Preparation of Compound 101

[0197]

[0198] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-101, and e-19 and a-19 were replaced with equimolar amounts of e-101 and A-101, respectively, to obtain compound 101 (17.24 g, yield 72%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 797.3641 (theoretical value: 797.3658). Theoretical elemental content (%) C 60 H 47 NO: C, 90.30; H, 5.94; N, 1.76. Measured elemental content (%): C, 90.28; H, 5.95; N, 1.79.

[0199] Synthesis Example 10: Preparation of Compound 111

[0200]

[0201] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-111 and d-85, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-111 and A-111, respectively, to obtain compound 111 (13.96 g, yield 70%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 664.3458 (theoretical value: 664.3440). Theoretical elemental content (%) C 49 H 28D9NO: C, 88.52; H, 6.97; N, 2.11. Measured elemental content (%): C, 88.54; H, 6.95; N, 2.13.

[0202] Synthetic Example 11: Preparation of Compound 149

[0203]

[0204] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-149 and d-149, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-149 and A-149, respectively, to obtain compound 149 (17.14 g, yield 77%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 755.3174 (theoretical value: 755.3188). Theoretical elemental content (%) C 57 H 41 NO: C, 90.56; H, 5.47; N, 1.85. Measured elemental content (%): C, 90.59; H, 5.45; N, 1.84.

[0205] Synthesis Example 12: Preparation of Compound 175

[0206]

[0207] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-149, and e-19 was replaced with an equimolar amount of e-175, yielding compound 175 (15.54 g, yield 79%). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 655.2891 (theoretical value: 655.2875). Theoretical elemental content (%) C 49 H 37 NO: C, 89.74; H, 5.69; N, 2.14. Measured elemental content (%): C, 89.77; H, 5.71; N, 2.11.

[0208] Synthesis Example 13: Preparation of Compound 230

[0209]

[0210] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-111 and d-42, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-230 and A-230, respectively, to obtain compound 230 (19.26 g, yield 75%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 855.3515 (theoretical value: 855.3501). Theoretical elemental content (%) C 65 H45 NO: C, 91.20; H, 5.30; N, 1.64. Measured elemental content (%): C, 91.18; H, 5.31; N, 1.67.

[0211] Synthesis Example 14: Preparation of Compound 239

[0212]

[0213] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-42, and e-19 was replaced with an equimolar amount of e-239, yielding compound 239 (17.74 g, yield 76%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 777.3047 (theoretical value: 777.3032). Theoretical elemental content (%) C 59 H 39 NO: C, 91.09; H, 5.05; N, 1.80. Measured elemental content (%): C, 91.11; H, 5.07; N, 1.79.

[0214] Synthesis Example 15: Preparation of Compound 249

[0215]

[0216] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-42 and d-149, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-249 and a-249, respectively, to obtain compound 249 (20.03 g, yield 75%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 889.4299 (theoretical value: 889.4284). Theoretical elemental content (%) C 67 H 55 NO: C, 90.40; H, 6.23; N, 1.57. Measured elemental content (%): C, 90.39; H, 6.25; N, 1.56.

[0217] Synthetic Example 16: Preparation of Compound 255

[0218]

[0219] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-255, and e-19 was replaced with an equimolar amount of e-255, yielding compound 255 (16.29 g, yield 72%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 753.3411 (theoretical value: 753.3427). Theoretical elemental content (%) C 54 H 47NOSi: C, 86.01; H, 6.28; N, 1.86. Measured elemental content (%): C, 86.03; H, 6.31; N, 1.88.

[0220] Synthesis Example 17: Preparation of Compound 260

[0221]

[0222] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-149, and e-19 was replaced with an equimolar amount of e-260, yielding compound 260 (14.95 g, yield 76%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 655.2529 (theoretical value: 655.2511). Theoretical elemental content (%) C 48 H 33 NO2: C, 87.91; H, 5.07; N, 2.14. Measured elemental content (%): C, 87.93; H, 5.09; N, 2.11.

[0223] Synthetic Example 18: Preparation of Compound 315

[0224]

[0225]

[0226] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-149, and e-19 was replaced with an equimolar amount of e-315, yielding compound 315 (14.36 g, yield 76%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 629.2368 (theoretical value: 629.2355). Theoretical elemental content (%) C 46 H 31 NO2: C, 87.73; H, 4.96; N, 2.22. Measured elemental content (%): C, 87.75; H, 4.93; N, 2.25.

[0227] Synthesis Example 19: Preparation of Compound 320

[0228]

[0229] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of a-85 and d-149, respectively, and e-19 was replaced with equimolar amounts of e-320, yielding compound 320 (15.38 g, yield 75%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 683.2750 (theoretical value: 683.2762). Theoretical elemental content (%) C 50 H29 D4NO2: C, 87.82; H, 5.45; N, 2.05. Measured elemental content (%): C, 87.84; H, 5.44; N, 2.02.

[0230] Synthesis Example 20: Preparation of Compound 347

[0231]

[0232] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-347, and e-19 and a-19 were replaced with equimolar amounts of e-347 and A-347, respectively, to obtain compound 347 (18.87 g, yield 74%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 849.3784 (theoretical value: 849.3767). Theoretical elemental content (%) C 63 H 39 D5N2O: C, 89.01; H, 5.81; N, 3.30. Measured elemental content (%): C, 89.04; H, 5.82; N, 3.28.

[0233] Synthesis Example 21: Preparation of Compound 357

[0234]

[0235] Following the method of Example 2, e-19, a-19, and B-19 were replaced with equimolar amounts of e-357, b-357, and d-357, respectively, to obtain compound 357 (16.07 g, yield 72%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 743.2947 (theoretical value: 743.2937). Theoretical elemental content (%) C 54 H 37 N3O: C, 87.19; H, 5.01; N, 5.65. Measured elemental content (%): C, 87.22; H, 5.03; N, 5.61.

[0236] Synthesis Example 22: Preparation of Compound 362

[0237]

[0238] Following the method in Example 2, e-19, a-19, and B-19 were replaced with equimolar amounts of e-362, A-362, and d-362, respectively, to obtain compound 362 (15.22 g, yield 68%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 745.3728 (theoretical value: 745.3742). Theoretical elemental content (%) C 54 H 51NS: C, 86.93; H, 6.89; N, 1.88. Measured elemental content (%): C, 86.96; H, 6.91; N, 1.85.

[0239] Synthesis Example 23: Preparation of Compound 366

[0240]

[0241] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-366, and e-19 was replaced with an equimolar amount of e-366, yielding compound 366 (14.32 g, yield 76%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 627.2432 (theoretical value: 627.2416). Theoretical elemental content (%) C 43 H 37 NSSi: C, 82.25; H, 5.94; N, 2.23. Measured elemental content (%): C, 82.26; H, 5.97; N, 2.20.

[0242] Synthesis Example 24: Preparation of Compound 382

[0243]

[0244]

[0245] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-382, and e-19 was replaced with an equimolar amount of e-382, yielding compound 382 (14.03 g, yield 74%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 631.2315 (theoretical value: 631.2334). Theoretical elemental content (%) C 46 H 33 NS: C, 87.44; H, 5.26; N, 2.22. Measured elemental content (%): C, 87.47; H, 5.24; N, 2.21.

[0246] Synthesis Example 25: Preparation of Compound 400

[0247]

[0248] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of a-111 and d-400, respectively, and e-19 was replaced with equimolar amounts of e-400, yielding compound 400 (14.01 g, yield 73%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 639.2719 (theoretical value: 639.2708). Theoretical elemental content (%) C 47 H37 N3S: C, 82.59; H, 5.83; N, 6.57. Measured elemental content (%): C, 82.57; H, 5.81; N, 6.55.

[0249] Synthesis Example 26: Preparation of Compound 407

[0250]

[0251] Following the method of Example 2, e-19 and B-19 were replaced with equimolar amounts of e-407 and B-407, respectively, to obtain compound 407 (17.46 g, yield 73%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 796.2931 (theoretical value: 796.2912). Theoretical elemental content (%) C 58 H 40 N2S: C, 87.40; H, 5.06; N, 3.51. Measured elemental content (%): C, 87.38; H, 5.04; N, 3.54.

[0252] Synthesis Example 27: Preparation of Compound 431

[0253]

[0254]

[0255] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-431, and e-19 and a-19 were replaced with equimolar amounts of e-431 and A-431, respectively, to obtain compound 431 (14.22 g, yield 75%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 631.2322 (theoretical value: 631.2334). Theoretical elemental content (%) C 46 H 33 NS: C, 87.44; H, 5.26; N, 2.22. Measured elemental content (%): C, 87.47; H, 5.23; N, 2.21.

[0256] Synthesis Example 28: Preparation of Compound 472

[0257]

[0258] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-472 and d-472, respectively, and e-19 was replaced with equimolar amounts of e-472, yielding compound 472 (16.83 g, yield 74%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 757.2563 (theoretical value: 757.2552). Theoretical elemental content (%) C54 H 35 N3S: C, 85.57; H, 4.65; N, 5.54. Measured elemental content (%): C, 85.55; H, 4.67; N, 5.52.

[0259] Synthesis Example 29: Preparation of Compound 479

[0260]

[0261] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-479 and d-479, respectively, and e-19 was replaced with equimolar amounts of e-479, yielding compound 479 (16.44 g, yield 71%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 771.2951 (theoretical value: 771.2960). Theoretical elemental content (%) C 57 H 41 NS: C, 88.68; H, 5.35; N, 1.81. Measured elemental content (%): C, 88.70; H, 5.33; N, 1.82.

[0262] Synthesis Example 30: Preparation of Compound 493

[0263]

[0264] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-493 and d-366, respectively, and e-19 was replaced with equimolar amounts of e-493, yielding compound 493 (16.72 g, yield 72%). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 773.2770 (theoretical value: 773.2752). Theoretical elemental content (%) C 56 H 39 NOS: C, 86.90; H, 5.08; N, 1.81. Measured elemental content (%): C, 86.89; H, 5.10; N, 1.84.

[0265] Synthesis Example 31: Preparation of Compound 505

[0266]

[0267] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-366, and e-19 was replaced with an equimolar amount of e-505, yielding compound 505 (16.61 g, yield 70%). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 823.3261 (theoretical value: 823.3273). Theoretical elemental content (%) C 61 H45 NS: C, 88.91; H, 5.50; N, 1.70. Measured elemental content (%): C, 88.94; H, 5.47; N, 1.71.

[0268] Synthesis Example 32: Preparation of Compound 547

[0269]

[0270] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-431, and e-19 was replaced with an equimolar amount of e-547, yielding compound 547 (16.85 g, yield 75%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 748.2561 (theoretical value: 748.2548). Theoretical elemental content (%) C 53 H 36 N₂OS: C, 85.00; H, 4.85; N, 3.74. Measured elemental content (%): C, 85.02; H, 4.87; N, 3.71.

[0271] Synthesis Example 33: Preparation of Compound 566

[0272]

[0273] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-566, and e-19 and a-19 were replaced with equimolar amounts of e-566 and a-249, respectively, to obtain compound 566 (16.50 g, yield 76%). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 737.2220 (theoretical value: 737.2211). Theoretical elemental content (%) C 52 H 35 NS2: C, 84.63; H, 4.78; N, 1.90. Measured elemental content (%): C, 84.65; H, 4.76; N, 1.89.

[0274] Synthesis Example 34: Preparation of Compound 574

[0275]

[0276] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-111 and d-431, respectively, and e-19 and a-19 were replaced with equimolar amounts of e-574 and a-249, respectively, to obtain compound 574 (13.87 g, yield 73%). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 633.2257 (theoretical value: 633.2239). Theoretical elemental content (%) C 44 H31 N3S: C, 83.38; H, 4.93; N, 6.63. Measured elemental content (%): C, 83.40; H, 4.95; N, 6.61.

[0277] Synthesis Example 35: Preparation of Compound 587

[0278]

[0279] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-587, and e-19 was replaced with an equimolar amount of e-587, yielding compound 587 (14.13 g, yield 76%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 619.3025 (theoretical value: 619.3036). Theoretical elemental content (%) C 46 H 29 D5N2: C, 89.14; H, 6.34; N, 4.52. Measured elemental content (%): C, 89.15; H, 6.32; N, 4.53.

[0280] Synthesis Example 36: Preparation of Compound 597

[0281]

[0282] Following the method of Example 2, d-19 was replaced with an equimolar amount of d-597, and e-19 was replaced with an equimolar amount of e-597, yielding compound 597 (15.48 g, yield 69%). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 747.3625 (theoretical value: 747.3613). Theoretical elemental content (%) C 55 H 45 N3: C, 88.32; H, 6.06; N, 5.62. Measured elemental content (%): C, 88.31; H, 6.05; N, 5.64.

[0283] Synthesis Example 37: Preparation of Compound 618

[0284]

[0285] Following the method of Example 2, c-19 and d-19 were replaced with equimolar amounts of c-618 and d-618, respectively, and e-19 was replaced with equimolar amounts of e-618, yielding compound 618 (17.02 g, yield 71%). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 798.3861 (theoretical value: 798.3850). Theoretical elemental content (%) C 60 H 34D8N2: C, 90.19; H, 6.31; N, 3.51. Measured elemental content (%): C, 90.21; H, 6.28; N, 3.52.

[0286] Device Examples

[0287] In this invention, the ITO glass substrate is ultrasonically cleaned twice with a 5% glass cleaning solution for 20 minutes each time, followed by ultrasonic cleaning twice with deionized water for 10 minutes each time. It is then ultrasonically cleaned sequentially with acetone and isoacetone for 20 minutes each time, and dried at 120°C. All organic materials are sublimated and have a purity of over 99.99%.

[0288] A combined IVL testing system was constructed, consisting of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrophotometer, to test the driving voltage, luminous efficiency, and CIE color coordinates of organic electroluminescent devices. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was ambient air at room temperature.

[0289] The device was fabricated using a vacuum evaporation system, with continuous evaporation under uninterrupted vacuum conditions. The materials used were housed in separate quartz crucibles containing different evaporation sources, the temperatures of which could be individually controlled. The thermal evaporation rate of organic materials was typically set at 0.1 nm / s, while the evaporation rate of electrode metals ranged from 0.4 to 0.6 nm / s. The prepared glass substrate was then placed in an OLED vacuum coating machine. During the thin film fabrication process, the system vacuum level should be maintained at 5 × 10⁻⁶. -5 Below Pa, organic layers and metal electrodes were deposited by changing the mask. The deposition rate was measured using an Inficon SQM160 quartz crystal film thickness gauge, and the film thickness was measured using a quartz crystal oscillator.

[0290] Example 1: Fabrication of Organic Electroluminescent Device 1

[0291] ITO is used as the anode on a glass substrate; 55 nm of 2-TNATA is vacuum-deposited on the anode to form a hole injection layer; 35 nm of compound 19 of the present invention is vacuum-deposited on the hole injection layer to form a first hole transport layer; 30 nm of CBP:Ir(ppy)2acac (mixed at a mass ratio of 95%:5%) is vacuum-deposited on the first hole transport layer to form a light-emitting layer; 10 nm of TPBi is vacuum-deposited on the light-emitting layer to form a hole blocking layer; 38 nm of Alq3 is vacuum-deposited on the hole blocking layer to form an electron transport layer; 0.9 nm of Liq is vacuum-deposited on the electron transport layer to form an electron injection layer; and 120 nm of Al is vacuum-deposited on the electron injection layer to form a cathode.

[0292] Examples 2-36: Fabrication of Organic Electroluminescent Devices 2-36

[0293] Replacing compound 19 in the first hole transport layer of Example 1 with compounds 25, 42, 54, 60, 69, 85, 101, 111, 149, 175, 230, 239, 249, 255, 260, 315, 320, 347, 357, 362, 366, 382, ​​400, 407, 431, 472, 479, 493, 505, 547, 566, 574, 587, 597, and 618 respectively, while keeping other steps the same, organic electroluminescent devices 2-36 are obtained.

[0294] Comparative Examples 1-3: Fabrication of Comparative Organic Electroluminescent Devices 1-3

[0295] By replacing compound 19 in the first hole transport layer of Example 1 with R-1, R-2, and R-3 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 1 to 3 were obtained.

[0296]

[0297] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 1 to 36 and Comparative Examples 1 to 3 of the present invention are shown in Table 1.

[0298] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0299]

[0300]

[0301]

[0302] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0303] As can be seen from Table 1, compared with Comparative Examples 1 to 3, when the triarylamine compound of Formula 1 of the present invention is used in the first hole transport layer of an organic electroluminescent device, the luminous efficiency and lifespan of the organic electroluminescent device are improved.

[0304] Example 37: Fabrication of Organic Electroluminescent Device 37

[0305] ITO is used as the anode on a glass substrate; a hole injection layer of 58 nm HAT-CN is vacuum-deposited on the anode; a first hole transport layer of 30 nm HT-1 is vacuum-deposited on the hole injection layer; compound 19 of the present invention is vacuum-deposited on the first hole transport layer as a second hole transport layer with a thickness of 15 nm; a light-emitting layer of 36 nm BH-1:BD-1 (mixed at a mass ratio of 96%:4%) is vacuum-deposited on the second hole transport layer; an electron transport layer of 34 nm BCP:Liq (mixed at a mass ratio of 1:1) is vacuum-deposited on the light-emitting layer; an electron injection layer of 1.0 nm LiF is vacuum-deposited on the electron transport layer; and a cathode of 120 nm Al is vacuum-deposited on the electron injection layer.

[0306] Examples 38-72: Fabrication of Organic Electroluminescent Devices 38-72

[0307] Replacing compound 19 in the second hole transport layer of Example 37 with compounds 25, 42, 54, 60, 69, 85, 101, 111, 149, 175, 230, 239, 249, 255, 260, 315, 320, 347, 357, 362, 366, 382, ​​400, 407, 431, 472, 479, 493, 505, 547, 566, 574, 587, 597, and 618 respectively, while keeping all other steps the same, organic electroluminescent devices 38-72 are obtained.

[0308] Comparative Examples 4-5: Fabrication of Comparative Organic Electroluminescent Devices 4-5

[0309] By replacing compound 19 in the second hole transport layer of Example 37 with R-4 and R-5 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 4-5 were obtained.

[0310]

[0311] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 36-75 and Comparative Examples 4-5 of this invention are shown in Table 2.

[0312] Table 2. Test data on the luminescence characteristics of organic electroluminescent devices.

[0313]

[0314]

[0315] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0316] As can be seen from the results in Table 2, when the triarylamine compounds of the present invention are applied to organic electroluminescent devices as the second hole transport layer material, the device performance is significantly improved compared with comparative examples 4-5, exhibiting the advantages of high luminous efficiency and long service life.

[0317] Example 73: Fabrication of Organic Electroluminescent Device 73

[0318] An organic electroluminescent device is formed by vacuum evaporating 60 nm of HAT-CN onto a glass substrate as the anode, forming a hole injection layer; vacuum evaporating 40 nm of HT-1 onto the hole injection layer as the hole transport layer; vacuum evaporating 35 nm of BH-2:BD-2 (mixed at a mass ratio of 97% to 3%) onto the hole transport layer as the light-emitting layer; vacuum evaporating 35 nm of ET2:Liq (mixed at a mass ratio of 1:1) onto the light-emitting layer as the electron transport layer; vacuum evaporating 1.0 nm of LiF onto the electron transport layer as the electron injection layer; vacuum evaporating 15 nm of Mg:Ag (mass ratio of 1:1) onto the electron injection layer as the cathode; and evaporating compound 19 of the present invention onto the cathode layer to form a capping layer with a thickness of 72 nm.

[0319] Examples 74-92: Fabrication of Organic Electroluminescent Devices 74-92

[0320] In Example 36, compound 19 in the second hole transport layer was replaced with compounds 25, 85, 175, 230, 239, 260, 315, 320, 347, 366, 382, ​​472, 479, 493, 547, 566, 574, 587, and 618, respectively, while the other steps remained the same, to obtain organic electroluminescent devices 74-92.

[0321] Comparative Examples 6-8: Fabrication of Comparative Organic Electroluminescent Devices 6-8

[0322] By replacing compound 19 in the capping layer of Example 73 with R-6, R-7, and R-8 respectively, and keeping the other steps the same, comparative organic electroluminescent devices 6-8 were obtained.

[0323]

[0324] The luminescence characteristics test results of the organic electroluminescent devices prepared in Examples 73-92 and Comparative Examples 6-8 of this invention are shown in Table 3.

[0325] Table 3. Test data on the luminescence characteristics of organic electroluminescent devices.

[0326]

[0327] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0328] As can be seen from the results in Table 3, the triarylamine compounds of the present invention, when used as a capping material in organic electroluminescent devices, can effectively improve the light extraction efficiency compared with comparative examples 6-8, thereby improving the luminous efficiency and lifespan of organic electroluminescent devices. They are high-performance capping materials for organic electroluminescent devices.

[0329] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A triarylamine compound, characterized in that, The triarylamine compounds are represented by the structure shown in Formula 1: The Ar1 is selected from substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl; The x is selected from CH; the x at the bonding site is selected from C; The Ar2 is selected from formula 2. Formula 2 is selected from any one of the following groups: The R3 is independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, trimethylsilyl, triethylsilyl, and combinations thereof; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other; The R4 is independently selected from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, pyridyl, and combinations thereof; wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and in the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other; The R a Selected from any one of the following groups, whether substituted or unsubstituted: phenyl, biphenyl, naphthyl; c1 is selected from 1 or 2; d1 is selected from 1, 2, 3 or 4; d2 is selected from 1, 2, 3, 4, 5 or 6; d3 is selected from 1 or 2; d7 is selected from 1, 2 or 3; The Ar3 is selected from Formula 2 or any one of the following groups: The R6 is selected from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, trimethylsilyl, triphenylsilyl, and combinations thereof, wherein the substituent in "substituted or unsubstituted" is selected from one or more of deuterium, deuterated methyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and in the case of being substituted by multiple substituents, the multiple substituents are the same as or different from each other; The R e The group is independently selected from hydrogen, deuterium, tritium, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; The f1 is selected from 1, 2, 3, 4, or 5; the f2 is selected from 1, 2, 3, 4, 5, 6, or 7; the f3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the f4 is selected from 1, 2, 3, or 4; the f6 is selected from 1, 2, or 3; the f7 is selected from 1, 2, 3, 4, 5, or 6; the f8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; when there are two or more R6, the two or more R6 are the same as or different from each other; R1 and R2 are selected from hydrogen, deuterium, tritium, substituted or unsubstituted: methyl, ethyl, propyl, butyl, pentyl, hexyl and any combination thereof, whether the same or different; The a is selected from 1, 2, 3, or 4; the b is selected from 1, 2, 3, or 4; The L1 is selected from any one of the following groups and combinations thereof: The R7 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and any combination thereof; The R f R g The group is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; The R i Selected from hydrogen, deuterium, tritium, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and combinations thereof; The g1 is selected from 1, 2, 3, or 4; the g2 is selected from 1, 2, or 3; the g3 is selected from 1 or 2; the g4 is selected from 1, 2, 3, 4, 5, or 6; the g5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the g6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R7, R i At that time, two or more R7, R i They are the same as or different from each other; The L2 is selected from a single bond or any one of the following groups and combinations thereof: The L3 is selected from a single bond or any one of the following groups and combinations thereof: The R8 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and any combination thereof; h1 is selected from 1, 2, 3, or 4; h2 is selected from 1, 2, or 3; h3 is selected from 1 or 2; h4 is selected from 1, 2, 3, 4, 5, or 6; h5 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; h6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; when there are two or more R8s, the two or more R8s are the same as or different from each other; Ar1, R a R e R1, R2, R7, R f R g R i The "substituted" group in "substituted or unsubstituted" in R8 is selected from one of the following groups: deuterium, methyl, ethyl, propyl, butyl.

2. The triarylamine compound according to claim 1, characterized in that, In Equation 1, " "Selected from any one of the following groups:" R1 and R2 are independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and any combination thereof; a1 is selected from 1, 2, 3 or 4; b1 is selected from 1, 2, 3 or 4.

3. The triarylamine compound according to claim 1, characterized in that, The Ar2 is selected from any one of the following groups derived from Formula 2: The R3 is independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trimethylsilyl, and combinations thereof; wherein the substituent in "substituted or unsubstituted" is selected from deuterium; The R4 is independently selected from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, pyridyl, and combinations thereof; wherein the substituent in "substituted or unsubstituted" is selected from deuterium.

4. The triarylamine compound according to claim 1, characterized in that, The Ar3 is selected from Formula 2 or any one of the following groups: The R 6a The same or different from any of the following groups selected from hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl, phenyl, trimethylsilyl, triphenylsilyl and combinations thereof, wherein the substituent in "substituted or unsubstituted" is selected from deuterium; The R6 is selected, either identically or differently, from hydrogen, deuterium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, and combinations thereof, wherein the substituent in "substituted or unsubstituted" is selected from deuterium; The R e The group is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl and any combination thereof.

5. The triarylamine compound according to claim 1, characterized in that, The L1 is selected from any one of the following groups and combinations thereof: The R7 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl and any combination thereof; The R i Selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups: methyl and any combination thereof.

6. The triarylamine compound according to claim 1, characterized in that, The L2 is selected from a single bond or any one of the following groups and combinations thereof: The L3 is selected from a single bond or any one of the following groups and combinations thereof: The R8 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl and any combination thereof.

7. A triarylamine compound, characterized in that, The triarylamine compounds are selected from any 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 at least one of the electrodes of the anode and the cathode, characterized in that, The organic layer contains any one or a combination of at least two of the triarylamine compounds described in any one of claims 1 to 7.

9. An organic electroluminescent device according to claim 8, characterized in that, The organic layer includes a hole transport region or a capping layer, the hole transport region being located between the anode and the cathode, the capping layer being located outside at least one of the electrodes of the anode and the cathode, and at least one of the hole transport regions or capping layers 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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