A compound of a triarylamine class and an organic electroluminescence device thereof
By using triarylamine compounds as hole transport layer and capping layer materials, the problem of insufficient hole transport layer material performance in OLED devices was solved, improving the luminous efficiency and lifetime of the devices, reducing total internal reflection and waveguide loss, and achieving higher optical coupling output efficiency.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- CHANGCHUN HYPERIONS TECH CO LTD
- Filing Date
- 2023-10-11
- Publication Date
- 2026-06-12
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Figure QLYQS_1 
Figure QLYQS_2 
Figure QLYQS_3
Abstract
Description
Technical Field
[0001] This invention relates to the field of organic electroluminescent materials technology, specifically to a triarylamine compound and its organic electroluminescent device. Background Technology
[0002] Organic light-emitting diodes (OLEDs) are rapidly emerging due to their numerous outstanding properties, including ultra-thinness, all-solidification, low power consumption, natural light, fast response speed, wide color gamut, good temperature characteristics, and the ability to achieve flexible displays. In the past 20 years, OLED display technology has made tremendous progress, with applications spanning mobile terminals such as smartphones and digital cameras, instrument displays, and computer monitors. Now, with increasingly higher demands for displays and lighting, OLEDs, with their many advantages, are deeply attracting the attention of high-level technical personnel from many companies and universities worldwide.
[0003] With the continuous advancement of science and technology, the structure of organic electroluminescent devices has been continuously optimized, evolving from simple single-layer device structures to three-layer and multi-layer device structures. Currently, the organic functional layers involved in organic electroluminescent devices include hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, and capping layers.
[0004] The fundamental function of the hole transport layer is to increase the hole transport rate within the device and effectively block electrons within the emissive layer, achieving maximum recombination between charge carriers. Simultaneously, the hole transport material must possess good thermal stability, film-forming properties, and appropriate highest occupied molecular orbitals (HOMO) and triplet energy levels to achieve high matching between layers, including the emissive layer, thereby improving the device's brightness, luminous efficiency, and lifespan. Furthermore, the significant gap between the external and internal quantum efficiencies of OLEDs severely restricts their development and application. By placing a capping layer with a high refractive index outside the semi-transparent electrode, total internal reflection loss and waveguide loss in OLED devices can be effectively reduced, improving optical coupling output efficiency.
[0005] To meet the current industrial application requirements of OLED devices, it is essential to select OLED functional materials with higher performance to achieve the comprehensive characteristics of high efficiency and long lifespan. Therefore, developing higher performance hole transport layer materials and capping layer materials is particularly important. Summary of the Invention
[0006] To address the aforementioned problems in the existing technology, this invention provides a triarylamine compound that can effectively improve the luminous efficiency and lifespan of organic electroluminescent devices. Specifically, the technical solution of this invention is as follows:
[0007] Specifically, the present invention provides a triarylamine compound having the structure of chemical formula 1.
[0008]
[0009] Wherein, A is selected from the groups shown in Formula 1-1 below;
[0010]
[0011] The B is selected from the groups shown in Formula 1-2 or Formula 1-3;
[0012]
[0013] The Ar is selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl groups.
[0014] The same or different v is selected from C or N atoms; when v is a connection site connected to L3, v is a C atom;
[0015] The R1 and R2, whether identical or different, are selected from any one or a combination of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring, or two adjacent R1s connected to each other to form a substituted or unsubstituted ring, or two adjacent R2s connected to each other to form a substituted or unsubstituted ring; a is selected from 1, 2, 3 or 4; b is selected from 1, 2 or 3;
[0016] The x atoms that are the same or different are selected from C or N atoms;
[0017] The R3 is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted silyl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl groups.
[0018] The R4, R5, and R6, whether identical or different, are selected from any one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl rings, wherein two adjacent R4s are interconnected to form a substituted or unsubstituted ring; c is selected from 1, 2, 3, 4, 5, 6, 7, or 8; m is selected from 1 or 2; n is selected from 1 or 2.
[0019] The Y0 is selected from O atom, S atom or N(Ra); the Ra is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring;
[0020] Y1 and Y2 are independently selected from O atoms or S atoms;
[0021] The same or different E is selected from C(Rb) or N atoms, and the same or different Rb is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C2-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cyclic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring, or two adjacent Rb are connected to each other to form a substituted or unsubstituted ring; provided that when E is the connection site connected to L2, E is a C atom;
[0022] 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-C12 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroarylene ring fused cycloyl group;
[0023] 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-C12 alicyclic and C6-C30 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroarylene rings in a fused cycloalcoholic group.
[0024] The present invention provides an organic electroluminescent device, which comprises any one or more of the triarylamine compounds described in the present invention.
[0025] Beneficial effects
[0026] This invention provides a triarylamine compound and its organic electroluminescent device. The compound possesses excellent spatial configuration, high glass transition temperature, and appropriate HOMO and triplet energy levels, effectively controlling the crystallinity of the material and giving it good thermal stability. When used as a hole transport layer in OLED devices, it exhibits high energy level matching with adjacent organic functional layers, reducing hole transport resistance and effectively confining electrons within the light-emitting layer, preventing them from moving to the hole transport layer. This compound effectively improves the luminous efficiency of the device and extends its lifespan. Furthermore, the triarylamine compound of this invention has a high refractive index; when used as a capping layer material in organic light-emitting devices, it effectively reduces total internal reflection loss and waveguide loss in OLED devices, further improving luminous efficiency. Detailed Implementation
[0027] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art fall within the scope defined by the present invention.
[0028] In this specification, "*" indicates a portion connected to another substituent. "*" can be attached to any optional position of the group / fraction to which it is attached.
[0029] 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.
[0030] In this specification, when the position of a substituent or linker site on the ring is not fixed, it means that it can be linked to any of the optional sites on the ring. For example, Can represent Can represent Can represent And so on.
[0031] Examples of halogens described in this invention may include fluorine, chlorine, bromine, and iodine.
[0032] The alkyl group referred to in this invention is a general term for monovalent groups obtained by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 25 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, etc., but are not limited thereto.
[0033] The alicyclic group mentioned in this invention refers to the general term for monovalent groups obtained by removing one hydrogen atom from an alicyclic hydrocarbon molecule. These groups can be cycloalkyl, cycloalkenyl, etc., preferably having 3 to 25 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, more preferably 5 to 10 carbon atoms, and most preferably 5 to 7 carbon atoms. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, etc., but are not limited thereto.
[0034] The aryl group mentioned in this invention refers to the general term for the monovalent group obtained by removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, particularly preferably 6 to 15 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, and specific examples may include biphenyl, terphenyl, tetraphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, and specific examples may include naphthyl, anthraceneyl, phenanthryl, pyrene, peryl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, spirofluorenyl, spirodifluorenyl, etc., but not limited to this.
[0035] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, or phosphorus atoms, and preferably have 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or on a cyclic heteroatom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Specific examples of the monocyclic heteroaryl group may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furanyl, thiopheneyl, pyrroloyl, oxazolyl, thiazolyl, imidazolyl, etc., but are not limited thereto; specific examples of the polycyclic heteroaryl group may include bipyridyl, bipyrimidinyl, phenylpyridinyl, phenylpyrimidinyl, etc., but are not limited thereto; specific examples of the fused-ring heteroaryl group may include quinolinyl, isoquinolinyl, benzo[a]quinolinyl, benzo[a]isoquinolinyl, quinazolinyl, quinoxalinyl, benzo[a]quinazolinyl, benzo[a]quinazolinyl, benzo[a] Quinoxolinyl, o-phenantholinyl, naphridyl, indolyl, benzothiopheneyl, benzofuranyl, benzooxazolyl, benzoimidazoyl, benzothiazoyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, dibenzooxazolyl, dibenzoimidazoyl, dibenzothiazoyl, carbazoleyl, benzocarbazoleyl, acridineyl, 9,10-dihydroacridyl, phenoxazinyl, phenthiazinyl, phenoxazinyl, spirofluorenexanthraceneyl, spirofluorenethixanthraceneyl, etc., but not limited to these.
[0036] The arylene group referred to in this invention refers to the general term for the divalent group obtained by removing two hydrogen atoms from the aromatic nucleus of an aromatic hydrocarbon molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 30 carbon atoms, more preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. Specific examples may include phenylene, biphenylene, terphenylene, naphthylene, anthracene, phenanthrene, pyrene, trimethyleneene, perylene, fluorene, fluorenylene, phenylfluorene, etc., but are not limited thereto.
[0037] 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 heteroatom is selected from O, S, N, Si, B, P, etc., but is not limited thereto. Preferably, it has 2 to 30 carbon atoms, more preferably 2 to 18 carbon atoms, particularly preferably 2 to 15 carbon atoms, and most preferably 2 to 12 carbon atoms. The heteroaryl group includes monocyclic heteroaryl, polycyclic heteroaryl, fused-ring heteroaryl, or combinations thereof. Examples of the heteroaryl group include, but are not limited to, the following groups: pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, quinazolinyl, naphthinyl, dibenzofuran, dibenzothiophene, etc., but are not limited thereto.
[0038] The “substituted or unsubstituted silyl group” as described in this invention refers to the -Si(R)3 group, wherein each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C1-C30 alkenyl, substituted or unsubstituted C3-C30 alicyclic group, 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 is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl. 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 30 carbon atoms, more preferably 6 to 24, even more preferably 6 to 18, and most preferably 6 to 12. The heteroaryl group preferably has 2 to 30 carbon atoms, more preferably 2 to 24, even more preferably 2 to 18, and most preferably 2 to 12. Preferably, each R is the same or different and is selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, or substituted or unsubstituted groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, cyclopropyl, cyclobutyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyltert-butylsilyl, tricyclopentylsilyl, tricyclohexylsilyl, triphenylsilyl, triphenylsilyl, tripyridylsilyl, tripyridylsilyl, etc., but are not limited thereto.
[0039] The fused alicyclic and aromatic rings described in this invention refer to the monovalent group formed by removing one hydrogen atom after the aromatic ring and the alicyclic ring are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.
[0040] The fused cyclic group of alicyclic and heteroaromatic rings described in this invention refers to the general term for a monovalent group remaining after alicyclic and heteroaromatic rings are fused together and one hydrogen atom is removed. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 7 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. Examples may include pyridocyclobutyl, pyridocyclopentyl, pyridocyclohexyl, pyridocycloheptyl, pyridocyclopentenyl, pyridocyclohexenyl, etc., but are not limited thereto.
[0041] The fused alicyclic and aromatic ring groups described in this invention refer to the general term for divalent groups obtained by removing two hydrogen atoms after the alicyclic and aromatic rings are fused together. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and most preferably 6 to 14 carbon atoms. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzo[a]cyclopropane, benzo[a]cyclobutane, benzo[a]cyclopentane, benzo[a]cyclohexane, benzo[a]cycloheptane, benzo[a]cyclobutenyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropane, naphtho[a]cyclobutane, naphtho[a]cyclopentane, naphtho[a]cyclohexane, naphtho[a]cyclopentenyl, naphtho[a]cyclohexenyl, etc., but are not limited thereto.
[0042] The fused alicyclic and heteroaromatic rings described in this invention refer to the collective term for divalent groups remaining after removing two hydrogen atoms from the fused alicyclic and heteroaromatic rings. The alicyclic ring preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 7 carbon atoms. The heteroaromatic ring preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms. Examples may include, but are not limited to, pyridinocyclobutyl, pyridinocyclopentyl, pyridinocyclohexyl, pyridinocycloheptyl, pyridinocyclopentenyl, and pyridinocyclohexenyl groups.
[0043] In this invention, "substituted or unsubstituted" means that at least one hydrogen atom on a group is replaced by a substituent. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different. The position of the hydrogen atoms replaced by the substituents can be arbitrary. The substituents represented by "substituted or unsubstituted" include the following groups: deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 silyl groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C3-C15 alicyclic groups, substituted or unsubstituted C6-C20 aryl groups, substituted or unsubstituted C2-C20 heteroaryl groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C6-C20 aromatic groups, fused cyclic groups of substituted or unsubstituted C3-C15 alicyclic and C2-C20 heteroaryl groups, etc. Preferred groups include: deuterium, tritium, cyano, halogen, nitro, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, ferruginyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, ethyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, trinaphthylsilyl, phenyl, biphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene. The substituents include benzo[a]yl, fluoranyl, benzocyclopropane, benzocyclobutane, dihydroindyl, tetrahydronaphthyl, benzocycloheptyl, benzocyclobutenyl, indyl, dihydronaphthyl, fluorenyl, spirodifluorenyl, benzofuranyl, benzothiopheneyl, benzopyrroleyl, benzooxazolyl, benzothiazolyl, benzoimidazolyl, dibenzofuranyl, dibenzothiopheneyl, indolyl, carbazoleyl, benzodioxoclonyl, benzodisulfideyl, dihydroisobenzofuranyl, dihydrobenzofuranyl, dihydrobenzothiopheneyl, dihydroisobenzothiopheneyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, etc. Furthermore, each of the above substituents can be substituted or unsubstituted. Two adjacent substituents can bond to form a ring.
[0044] The "linked ring formation" described in this invention refers to two groups being linked together by chemical bonds and optionally undergoing aromatization. Examples are shown below:
[0045]
[0046] In this invention, the ring formed by the connection can be an aromatic ring system, an aliphatic ring system, or a ring system formed by the fusion of both. The ring formed by the connection can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, a seven-membered ring, or a fused ring. Specific examples of aromatic ring systems may include benzene, naphthalene, anthracene, phenanthrene, or pyrene, but are not limited thereto. Specific examples of aliphatic ring systems may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cyclobutene, cyclopentene, or cyclohexene, but are not limited thereto. Specific examples of fused ring systems formed by both aromatic and aliphatic rings may include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutene, benzocyclopentene, or benzocyclohexene, but are not limited thereto.
[0047] The term "at least one" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.
[0048] The term "one or more" as used in this invention includes, where permitted, one, two, three, four, five, six, seven, eight, or more.
[0049] This invention provides a triarylamine compound having the structure of chemical formula 1.
[0050]
[0051] Wherein, A is selected from the groups shown in Formula 1-1 below;
[0052]
[0053] The B is selected from the groups shown in Formula 1-2 or Formula 1-3;
[0054]
[0055] The Ar is selected from any one of the following: substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl groups.
[0056] The same or different v is selected from C or N atoms; when v is a connection site connected to L3, v is a C atom;
[0057] The R1 and R2, whether identical or different, are selected from any one or a combination of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring, or two adjacent R1s connected to each other to form a substituted or unsubstituted ring, or two adjacent R2s connected to each other to form a substituted or unsubstituted ring; a is selected from 1, 2, 3 or 4; b is selected from 1, 2 or 3;
[0058] The x atoms that are the same or different are selected from C or N atoms;
[0059] The R3 is selected from any one or a combination of substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, substituted or unsubstituted silyl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl groups.
[0060] The R4, R5, and R6, whether identical or different, are selected from any one of the following: hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl rings, wherein two adjacent R4s are interconnected to form a substituted or unsubstituted ring; c is selected from 1, 2, 3, 4, 5, 6, 7, or 8; m is selected from 1 or 2; n is selected from 1 or 2.
[0061] The Y0 is selected from O atom, S atom or N(Ra); the Ra is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring;
[0062] Y1 and Y2 are independently selected from O atoms or S atoms;
[0063] The same or different E is selected from C(Rb) or N atoms, and the same or different Rb is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C2-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cyclic group of substituted or unsubstituted C3-C12 alicyclic and C6-C30 aromatic ring, fused cyclic group of substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroaryl ring, or two adjacent Rb are connected to each other to form a substituted or unsubstituted ring; provided that when E is the connection site connected to L2, E is a C atom;
[0064] 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-C12 alicyclic and C6-C30 aromatic ring fused cycloyl group, substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroarylene ring fused cycloyl group;
[0065] 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-C12 alicyclic and C6-C30 aromatic rings in a fused cycloalcoholic group, or substituted or unsubstituted C3-C12 alicyclic and C2-C30 heteroarylene rings in a fused cycloalcoholic group.
[0066] Preferably, R3 is selected from the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, benzo[…]. The following is a list of compounds: pyrrole, benzoxazolyl, benzothiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0067] Preferably, A is selected from any one of the following groups:
[0068]
[0069]
[0070]
[0071] The R4 group, whether identical or different, is selected from hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzo[…]. The following is a list of compounds: thienyl, benzopyrrole, benzoxazolyl, benzothiazolyl, benzoimidazolyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0072] The c is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the c1 is selected from 1, 2, 3, or 4; the c2 is selected from 1, 2, 3, 4, or 5; the c3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c4 is selected from 1, 2, 3, 4, 5, 6, or 7; the c5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; the c6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the c7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; the c8 is selected from 1, 2, 3, 4, 5, or 6; and the c9 is selected from 1, 2, or 3.
[0073] Preferably, B is selected from any one of the following groups:
[0074]
[0075]
[0076] R5 and R6 are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic rings, and fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl rings; m is selected from 1 or 2; n is selected from 1 or 2;
[0077] The Ra is the same as or different from any one of the following: substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C2-C18 heteroaryl groups, substituted or unsubstituted silyl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl groups;
[0078] The same or different E is selected from C(Rb) or N atoms, and the same or different Rb is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, and substituted or unsubstituted silyl.
[0079] Preferably, each group has at most three E's selected from N, or at most two E's selected from N, or at most one E's selected from N.
[0080] Preferably, B is selected from any one of the following groups:
[0081]
[0082] R5, R6, and Rb are independently selected from hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, benzopyrene. The following is a list of compounds: pyridyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazole, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl; wherein m is selected from 1 or 2; and n is selected from 1 or 2.
[0083] The Ra is the same as or different from the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, benzene The following are all of the following: pyrroleyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0084] The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2 or 3; the d3 is selected from 0, 1 or 2; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6; and the d5 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.
[0085] Preferably, R5, R6, and Rb are independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0086] Preferably, the Ra is the same as or different from any of the following groups, whether substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0087] Preferably, when B is of formula 1-3, it is selected from the following groups:
[0088]
[0089] R6 and Rb are independently selected from hydrogen, deuterium, halogen, cyano, or any of the following groups, substituted or unsubstituted: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, naphthyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, and triphenylsilyl.
[0090] The d2 is selected from 0, 1, 2 or 3; the d3 is selected from 0, 1 or 2; the d6 is selected from 0, 1, 2, 3, 4 or 5; the d7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.
[0091] Preferably, the Ar is selected from any one of the following groups:
[0092]
[0093] The z that is the same or different is selected from C(Rc) or N atoms, and the Rc that is the same or different is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic ring, and fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl ring;
[0094] W1 and W3 are independently selected from any one of O, S, C(Rd Re), and N(Rf);
[0095] The W2 is selected from C(Rg) or N;
[0096] The Rd, Re, and Rg are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic group, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl group, or a substituted or unsubstituted spirocyclic group formed between two adjacent Rd and Re;
[0097] The Rf is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C2-C18 heteroaryl groups, substituted or unsubstituted silyl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl groups;
[0098] The ring M is selected from substituted or unsubstituted C3-C12 aliphatic rings.
[0099] Preferably, the Ar is selected from any one of the following groups:
[0100]
[0101] The R7 is the same as or different from the following groups selected from hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzo[…]. Thiophene, benzopyrrole, benzoxazolyl, benzothiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl;
[0102] The number e1 is selected from 1, 2, 3, 4, or 5; the number e2 is selected from 1, 2, 3, or 4; the number e3 is selected from 1, 2, 3, 4, 5, 6, or 7; the number e4 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the number e5 is selected from 1, 2, 3, 4, 5, or 6; the number e6 is selected from 1 or 2; the number e7 is selected from 1, 2, or 3; and the number e8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8.
[0103] Preferably, the Ar is selected from any one of the following groups:
[0104]
[0105] The q1 is selected from 1, 2, 3, 4 or 5; the q2 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the q3 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13; the q4 is selected from 1, 2, 3, 4, 5, 6 or 7.
[0106] Preferably, L1 is selected from any one of the following groups, and L2 and L3 are independently selected from single bonds or any one of the following groups.
[0107]
[0108] The T atoms, whether the same or different, are selected from C(Rh) or N atoms. The Rh atoms, whether the same or different, are selected from hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic ring, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl, or two adjacent Rh atoms are connected to each other to form a substituted or unsubstituted ring.
[0109] The values t1, t2, t3, and t4 are independently selected from 0 or 1;
[0110] Q1 and Q2 are independently selected from any one of O, S, C(Rk Rp), and N(Rq);
[0111] Q3 is selected from C(Rw) or N;
[0112] The Rk, Rp, and Rw are independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, nitro, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 alicyclic group, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C2-C18 heteroaryl, substituted or unsubstituted silyl, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic group, fused cycloalcoholic group of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl group, or a substituted or unsubstituted spirocyclic group formed between two adjacent Rk and Rp;
[0113] The Rq is selected from any one of the following: substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C12 alicyclic groups, substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C2-C18 heteroaryl groups, substituted or unsubstituted silyl groups, fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C6-C18 aromatic groups, and fused cycloalkanes of substituted or unsubstituted C3-C12 alicyclic and C2-C18 heteroaryl groups;
[0114] The ring N is selected from substituted or unsubstituted C3-C12 aliphatic rings.
[0115] Preferably, L1 is selected from any one of the following groups, and L2 and L3 are independently selected from single bonds or any one of the following groups.
[0116]
[0117]
[0118] The R8 group, whether identical or different, is selected from hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornel, camphene, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzo[…]. Thiophene, benzopyrrole, benzoxazolyl, benzothiazolyl, benzimidazolyl, fluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl;
[0119] k1 is selected from 1, 2, 3 or 4; k2 is selected from 1, 2, 3, 4, 5 or 6; k3 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; k4 is selected from 1 or 2; k5 is selected from 1, 2 or 3; k6 is selected from 1, 2, 3, 4, 5, 6 or 7; k7 is selected from 1, 2, 3, 4 or 5.
[0120] Preferably, the R8 groups, whether identical or different, are selected from hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted groups of the following: methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzocyclopentyl, benzocyclohexyl, benzocyclopentenyl, benzocyclohexenyl, benzofuranyl, benzothiophene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.
[0121] Most preferably, the triarylamine compounds are selected from the following structures:
[0122]
[0123]
[0124]
[0125]
[0126]
[0127]
[0128]
[0129]
[0130]
[0131]
[0132]
[0133]
[0134]
[0135]
[0136]
[0137]
[0138]
[0139] The above lists some specific structural forms of triarylamine compounds represented by chemical formula 1 according to the present invention. However, the present invention is not limited to these listed chemical structures. Any structure based on the structure shown in chemical formula 1, with substituents as defined above, should be included.
[0140] The present invention also provides an organic electroluminescent device, wherein the organic electroluminescent device comprises any one or more of the triarylamine compounds described in the present invention.
[0141] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or on the side of the cathode away from the anode, and the organic layer contains any one or more of the triarylamine compounds described in this invention.
[0142] Preferably, the organic electroluminescent device may include one or more organic layers, wherein the organic layers are located between the anode and the cathode, the organic layers include a hole transport region, a light-emitting layer, and an electron transport region, the light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode; the organic layers are located on the side of the cathode opposite to the anode, and the organic layers include a capping layer.
[0143] The organic layer described in this invention can be a single-layer organic layer or a multi-layer organic layer. A single-layer organic layer includes a single layer containing a single material or a single layer containing multiple materials; a multi-layer organic layer includes multiple layers containing multiple materials.
[0144] Preferably, the organic electroluminescent device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer contains any one or more of the triarylamine compounds described in this invention.
[0145] Preferably, the hole transport region comprises any one or more of the triarylamine compounds described in this invention.
[0146] Preferably, the hole transport region includes a hole injection layer and a hole transport layer, the hole injection layer being located between the anode and the light-emitting layer, the hole transport layer being located between the hole injection layer and the light-emitting layer, and the hole transport layer comprising any one or more of the triarylamine compounds described in this invention.
[0147] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, wherein the first hole transport layer is located between the hole injection layer and the light-emitting layer, and the second hole transport layer is located between the first hole transport layer and the light-emitting layer; preferably, at least one of the first hole transport layer and the second hole transport layer comprises any one or more of the triarylamine compounds described in this invention.
[0148] Preferably, the first hole transport layer comprises any one or more of the triarylamine compounds described in this invention; preferably, the second hole transport layer comprises any one or more of the triarylamine compounds described in this invention; preferably, the first hole transport layer and the second hole transport layer comprise any one or more of the triarylamine compounds described in this invention.
[0149] Preferably, the hole transport layer comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein the first hole transport layer is located between the hole injection layer and the light-emitting layer, the second hole transport layer is located between the first hole transport layer and the light-emitting layer, and the third hole transport layer is located between the second hole transport layer and the light-emitting layer. Preferably, at least one of the first, second, and third hole transport layers comprises any one or more of the triarylamine compounds described in this invention.
[0150] Preferably, the first hole transport layer comprises any one or more of the triarylamine compounds described in this invention; preferably, the second hole transport layer comprises any one or more of the triarylamine compounds described in this invention; preferably, the third hole transport layer comprises any one or more of the triarylamine compounds described in this invention; preferably, the first hole transport layer and the second hole transport layer comprise any one or more of the triarylamine compounds described in this invention; preferably, the first hole transport layer and the third hole transport layer comprise any one or more of the triarylamine compounds described in this invention; preferably, the second hole transport layer and the third hole transport layer comprise any one or more of the triarylamine compounds described in this invention; preferably, the first hole transport layer, the second hole transport layer, and the third hole transport layer comprise any one or more of the triarylamine compounds described in this invention.
[0151] Preferably, the organic layer is located on the side of the cathode away from the anode, and the organic layer includes a capping layer, which may be a single-layer structure, a two-layer structure, or a multi-layer structure. The capping layer contains any one or more of the triarylamine compounds described in this invention.
[0152] This invention does not particularly limit the materials of the thin films in the organic electroluminescent device; substances known in the art can be used. The organic functional layers of the aforementioned organic electroluminescent device and the electrodes on both sides of the device are described below:
[0153] The anode of this invention is preferably made of a material with a high work function. The anode includes, but is not limited to, the materials described below: metals or alloys thereof, metal oxides, multilayer materials, conductive polymers, etc. Specific examples may include gold (Au), indium tin oxide (ITO), zinc oxide (ZnO), indium tin oxide / silver / indium tin oxide (ITO / Ag / ITO), polyaniline, etc., but are not limited thereto. The hole injection layer material of this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene, etc.
[0154] The hole injection layer material described in this invention is preferably a material with good hole-accepting ability. The hole injection layer material may include, but is not limited to, metalloporphyrins, oligothiophenes, anthraquinone compounds, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, and conductive polymers based on polyaniline and polythiophene.
[0155] The hole transport layer material described in this invention is preferably a material with good hole transport performance. It can be selected from small molecule materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, and butadiene compounds, as well as polymer materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, and a triaromatic amine compound provided in this invention, but is not limited thereto. Preferably, the hole transport layer is selected from the triaromatic amine compound described in this invention. It can be a single structure composed of a single substance, or a single-layer or multi-layer structure formed by different substances. The hole transport layer can include a single layer, or it can include a first hole transport layer, a second hole transport layer, a third hole transport layer, or more layers.
[0156] The luminescent layer material described in this invention can use red, green, or blue luminescent materials, and typically comprises a host material and dopants. The luminescent layer material may contain multiple host materials and multiple dopants. The dopants can be simple fluorescent or phosphorescent materials, or a combination of fluorescent and phosphorescent materials. The doping ratio of the host material and the dopants can vary depending on the materials used; preferably, the doping concentration of the dopant, based on the host compound, is less than 20 wt%. Fluorescent compounds can be used as dopants, such as pyrene derivatives, fluoranthene derivatives, aromatic amine derivatives, etc. Examples include 10-(2-benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-[1]benzopyran[6,7,8-ij]quinolineazine-11-one (C545T), 4,4'-bis(9-ethyl-3-carbazolevinyl)-1,1'-biphenyl (BCzVBi), 4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), etc. Phosphorescent materials can also be used, such as iridium complexes, osmium complexes, platinum complexes and other metal complexes. Examples include bis(4,6-difluorophenylpyridine-N,C2)pyridinecarboxylated iridium (FIrpic), tri(2-phenylpyridine)iridium (Ir(ppy)3), acetylacetonate di(2-phenylpyridine)iridium (Ir(ppy)2(acac)), etc.
[0157] The host material of the luminescent layer needs to have an appropriate energy level to effectively transfer the excitation energy to the guest luminescent material. It may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., as well as heterocyclic compounds including carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, pyrimidine derivatives, stilbeneylaryl derivatives, mestilbene derivatives, etc., but is not limited to these.
[0158] The electron transport material described in this invention is required to have excellent electron transport performance, effectively transporting electrons from the cathode to the light-emitting layer, and possessing a high electron mobility. It may contain any one or more of the following compounds: thiazole derivatives, quinoline derivatives, benzimidazole derivatives, oxazole derivatives, azirbenzene derivatives, diazanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, phenanthroline derivatives, metal chelates, etc., but is not limited to these.
[0159] The electron injection layer material described in this invention is preferably a material with good electron-accepting ability. The electron injection layer material may include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, metal oxides, and other substances with high electron-injection properties. Specific examples may include: Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, Al2O3, MoO3, MgF2, LiO, Yb, Tb, cesium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, etc., but are not limited to these.
[0160] The cathode material described in this invention is preferably a material with a low work function. The cathode includes, but is not limited to, the materials described below, metals or their alloys, multilayer materials, etc. Specific examples may include aluminum (Al), silver (Ag), lithium (Li), magnesium (Mg), magnesium:silver (Mg:Ag), etc., but are not limited to these.
[0161] The capping layer described in this invention may, in addition to using any one or at least two of the triarylamine compounds provided in this invention, be selected from any one or more of the following structures: inorganic compounds (e.g., metal oxides, metal nitrides, metal fluorides, etc.), organic compounds (arylamine derivatives, carbazole derivatives, benzimidazole derivatives, benzoxazole derivatives, benzothiazole derivatives, triazole derivatives, etc.), or may be formed by mixing inorganic and organic compounds, but is not limited thereto.
[0162] The following is one method for preparing the triarylamine compound represented by Formula 1 of this invention, but the preparation method of this invention is not limited thereto. The core structure of the triarylamine compound of Formula 1 can be prepared by the reaction route shown below. The substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.
[0163] [Synthesis Route]
[0164] Preparation of compounds of chemical formula 1 (triarylamines):
[0165] There are no particular limitations on the preparation method of the triarylamine compounds represented by Chemical Formula 1 of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reactions, carbon-nitrogen coupling reactions, etc., are described below:
[0166] Synthesis of intermediates:
[0167]
[0168] Compound synthesis:
[0169]
[0170] Xa, Xb, Xc, and Xd are each independently selected from any one of I, Br, and Cl; the limitations of R1, R2, v, Ar, A, B, L1, L2, L3, a, and b are the same as those described above.
[0171] 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.
[0172] Instruments: G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Instruments, UK); Vario ELcube organic elemental analyzer (Elementar Instruments, Germany)
[0173] [Synthesis Example]
[0174] Synthesis Example 1: Preparation of Intermediate A-72
[0175]
[0176] Preparation of intermediate b-72:
[0177] Under nitrogen protection, intermediate a-72 (22.55 g, 70.00 mmol), pinacol diboronate (17.78 g, 70.00 mmol), KOAc (15.51 g, 158.00 mmol), Pd(dppf)Cl2 (0.86 g, 1.17 mmol), and 1,4-dioxane (500 mL) were added sequentially to a reaction flask. The mixture was then heated under reflux for 3.5 hours. After the reaction was completed, the mixture was cooled to room temperature, and 500 mL of distilled water was added. The mixture was then extracted with ethyl acetate (600 mL × 3). The organic layer was dried over anhydrous MgSO4, and the ethyl acetate was removed by rotary evaporation. The mixture was then recrystallized from toluene:methanol (40:1) and dried to obtain intermediate b-72 (21.71 g, 84% yield); HPLC purity ≥99.85%. Mass spectrometry m / z: 369.1911 (theoretical value: 369.1900).
[0178] Preparation of intermediate A-72:
[0179] Under nitrogen protection, b-72 (18.46 g, 50.00 mmol), c-729 (13.61 g, 50.00 mmol), K2CO3 (11.06 g, 80 mmol), and 210 mL of mixed solvent (toluene:ethanol:water = 2:1:1) were added sequentially to the reaction flask. The air was then purged with nitrogen three times. Pd(PPh3)4 (0.58 g, 0.50 mmol) was then added, and the mixture was heated under reflux for 4 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with dichloromethane, allowed to stand, and separated. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was recrystallized from toluene and dried to obtain intermediate A-72 (15.64 g, yield 72%); HPLC purity ≥99.82%. Mass spectrometry m / z: 434.1770 (theoretical value: 434.1783).
[0180] Synthesis Example 2: Preparation of Intermediate A-78
[0181]
[0182] According to the method in Example 1, c-72 was replaced with an equimolar amount of c-78 to obtain intermediate A-78 (15.43 g). The purity of the solid was ≥99.87% as determined by HPLC. Mass spectrometry m / z: 434.1771 (theoretical value: 434.1783).
[0183] Synthesis Example 3: Preparation of Intermediate A-198
[0184]
[0185] According to the method in Example 1, a-72 was replaced with an equimolar amount of a-198, and c-72 was replaced with an equimolar amount of c-198 to obtain intermediate A-198 (13.07 g). The purity of the solid was ≥99.84% as determined by HPLC. Mass spectrometry m / z: 339.1795 (theoretical value: 339.1784).
[0186] Synthesis Example 4: Preparation of Intermediate A-201
[0187]
[0188] According to the method in Example 1, a-72 was replaced with an equimolar amount of a-201, and c-72 was replaced with an equimolar amount of c-198 to obtain intermediate A-201 (14.64 g). The purity of the solid was ≥99.83% as determined by HPLC. Mass spectrometry m / z: 390.2084 (theoretical value: 390.2096).
[0189] Synthesis Example 5: Preparation of Intermediate A-260
[0190]
[0191] According to the method in Example 1, a-72 was replaced with an equimolar amount of a-260, and c-72 was replaced with an equimolar amount of c-198 to obtain intermediate A-260 (15.25 g). The purity of the solid was ≥99.86% as determined by HPLC. Mass spectrometry m / z: 406.1879 (theoretical value: 406.1865).
[0192] Synthesis Example 6: Preparation of Compound 4
[0193]
[0194] Synthetic intermediate I-4
[0195] Under nitrogen protection, toluene (300 mL), A-4 (12.92 g, 50.00 mmol), B-4 (16.76 g, 50.00 mmol), palladium acetate (0.17 g, 0.75 mmol), sodium tert-butoxide (9.61 g, 100.00 mmol), and tri-tert-butylphosphine (3 mL of 0.50 M toluene solution) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 3 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation. Recrystallization was performed using toluene:ethanol (10:1) to obtain intermediate I-4 (21.28 g, yield 83%). The purity of the solid was ≥99.88% as determined by HPLC. Mass spectrometry m / z: 512.2239 (theoretical value: 512.2252).
[0196] Synthetic compound 4
[0197] Under nitrogen protection, toluene (200 ml), intermediate I-4 (12.82 g, 25.00 mmol), C-4 (4.93 g, 25.00 mmol), Pd2(dba)3 (0.23 g, 0.25 mmol), sodium tert-butoxide (4.81 g, 50.00 mmol), and X-Phos (0.24 g, 0.50 mmol) were added sequentially to a reaction flask. The mixture was stirred and heated under reflux for 5 hours. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. 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 4 (12.26 g, yield 78%). The purity of the solid was ≥99.98% as determined by HPLC. Mass spectrometry m / z: 628.2531 (theoretical value: 628.2515). Theoretical elemental content (%) C 46 H 32 N₂O: C, 87.87; H, 5.13; N, 4.46. Measured elemental content (%): C, 87.82; H, 5.15; N, 4.48.
[0198] Synthesis Example 7: Preparation of Compound 38
[0199]
[0200] Following the method of Example 6, B-4 was replaced with an equimolar amount of B-38, and C-4 was replaced with an equimolar amount of C-38, yielding compound 38 (14.49 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 782.2740 (theoretical value: 782.2756). Theoretical elemental content (%) C 57 H 38 N₂S: C, 87.44; H, 4.89; N, 3.58. Measured elemental content (%): C, 87.47; H, 4.88; N, 3.54.
[0201] Synthesis Example 8: Preparation of Compound 48
[0202]
[0203] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-48, yielding compound 48 (14.54 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 830.3287 (theoretical value: 830.3297). Theoretical elemental content (%) C 62 H 42N2O: C, 89.61; H, 5.09; N, 3.37. Measured elemental content (%): C, 89.66; H, 5.05; N, 3.36.
[0204] Synthesis Example 9: Preparation of Compound 56
[0205]
[0206] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-56, yielding compound 56 (15.72 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 872.3237 (theoretical value: 872.3225). Theoretical elemental content (%) C 64 H 44 N2S: C, 88.04; H, 5.08; N, 3.21. Measured elemental content (%): C, 88.06; H, 5.05; N, 3.23.
[0207] Synthesis Example 10: Preparation of Compound 72
[0208]
[0209] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-72, and C-4 was replaced with an equimolar amount of C-72, yielding compound 72 (13.96 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 820.2900 (theoretical value: 820.2912). Theoretical elemental content (%) C 60 H 40 N₂S: C, 87.77; H, 4.91; N, 3.41. Measured elemental content (%): C, 87.75; H, 4.93; N, 3.42.
[0210] Synthetic Example 11: Preparation of Compound 78
[0211]
[0212] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-78, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-78, yielding compound 78 (16.27 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 942.3623 (theoretical value: 942.3610). Theoretical elemental content (%) C 71 H 46 N₂O: C, 90.42; H, 4.92; N, 2.97. Measured elemental content (%): C, 90.44; H, 4.94; N, 2.94.
[0213] Synthesis Example 12: Preparation of Compound 19
[0214]
[0215] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-79, and C-4 was replaced with an equimolar amount of C-79, yielding compound 79 (14.65 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 836.3211 (theoretical value: 836.3225). Theoretical elemental content (%) C 61 H 44 N2S: C, 87.53; H, 5.30; N, 3.35. Measured elemental content (%): C, 87.50; H, 5.34; N, 3.32.
[0216] Synthesis Example 13: Preparation of Compound 90
[0217]
[0218] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-90, and C-4 with an equimolar amount of C-90, yielding compound 90 (15.90 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 948.3190 (theoretical value: 948.3174). Theoretical elemental content (%) C 69 H 44 N₂OS: C, 87.31; H, 4.67; N, 2.95. Measured elemental content (%): C, 87.33; H, 4.62; N, 2.97.
[0219] Synthesis Example 14: Preparation of Compound 91
[0220]
[0221] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-91, and C-4 was replaced with an equimolar amount of C-91, yielding compound 91 (14.25 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 780.3155 (theoretical value: 780.3141). Theoretical elemental content (%) C 58 H 40 N₂O: C, 89.20; H, 5.16; N, 3.59. Measured elemental content (%): C, 89.24; H, 5.18; N, 3.55.
[0222] Synthetic Example 15: Preparation of Compound 154
[0223]
[0224] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-154, B-4 with an equimolar amount of B-154, and C-4 with an equimolar amount of C-154, yielding compound 154 (15.85 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 892.3441 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N₂O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%): C, 90.14; H, 4.95; N, 3.12.
[0225] Synthetic Example 16: Preparation of Compound 155
[0226]
[0227] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-155, and C-4 with an equimolar amount of C-155, yielding compound 155 (14.67 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 837.3237 (theoretical value: 837.3226). Theoretical elemental content (%) C 61 H 35 D5N2S: C, 87.42; H, 5.41; N, 3.34. Measured elemental content (%): C, 87.45; H, 5.43; N, 3.30.
[0228] Synthesis Example 17: Preparation of Compound 169
[0229]
[0230] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-169, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-169, yielding compound 169 (15.62 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 832.2901 (theoretical value: 832.2912). Theoretical elemental content (%) C 61 H 40 N2S: C, 87.95; H, 4.84; N, 3.36. Measured elemental content (%): C, 87.98; H, 4.86; N, 3.32.
[0231] Synthesis Example 18: Preparation of Compound 182
[0232]
[0233] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-78, yielding compound 182 (15.03 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 780.3157 (theoretical value: 780.3141). Theoretical elemental content (%) C 58 H 40 N₂O: C, 89.20; H, 5.16; N, 3.59. Measured elemental content (%): C, 89.22; H, 5.18; N, 3.56.
[0234] Synthetic Example 19: Preparation of Compound 186
[0235]
[0236] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-186, yielding compound 186 (15.54 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 796.2900 (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, 87.44; H, 5.04; N, 3.54.
[0237] Synthesis Example 20: Preparation of Compound 187
[0238]
[0239] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-169, yielding compound 187 (15.34 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 796.2902 (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, 87.42; H, 5.03; N, 3.53.
[0240] Synthesis Example 21: Preparation of Compound 198
[0241]
[0242] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-198, and C-4 was replaced with an equimolar amount of C-198, yielding compound 198 (15.24 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 801.3238 (theoretical value: 801.3226). Theoretical elemental content (%) C 58 H 35 D5N2S: C, 86.86; H, 5.65; N, 3.49. Measured elemental content (%): C, 86.88; H, 5.67; N, 3.45.
[0243] Synthesis Example 22: Preparation of Compound 201
[0244]
[0245] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-201, and C-4 was replaced with an equimolar amount of C-78, yielding compound 201 (15.90 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 836.3784 (theoretical value: 836.3767). Theoretical elemental content (%) C 62 H 48 N₂O: C, 88.96; H, 5.78; N, 3.35. Measured elemental content (%): C, 88.94; H, 5.76; N, 3.38.
[0246] Synthesis Example 23: Preparation of Compound 203
[0247]
[0248] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-203, and C-4 was replaced with an equimolar amount of C-203, yielding compound 203 (14.45 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 780.3127 (theoretical value: 780.3141). Theoretical elemental content (%) C 58 H 40 N₂O: C, 89.20; H, 5.16; N, 3.59. Measured elemental content (%): C, 89.22; H, 5.18; N, 3.55.
[0249] Synthesis Example 24: Preparation of Compound 211
[0250]
[0251] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-211, B-4 with an equimolar amount of B-211, and C-4 with an equimolar amount of C-211, yielding compound 211 (14.06 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 780.3159 (theoretical value: 780.3141). Theoretical elemental content (%) C 58 H 40 N₂O: C, 89.20; H, 5.16; N, 3.59. Measured elemental content (%): C, 89.23; H, 5.19; N, 3.54.
[0252] Synthesis Example 25: Preparation of Compound 217
[0253]
[0254] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-217, and C-4 was replaced with an equimolar amount of C-78, yielding compound 217 (15.31 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 784.3380 (theoretical value: 784.3392). Theoretical elemental content (%) C 58 H 36 D4N2O: C, 88.74; H, 5.65; N, 3.57. Measured elemental content (%): C, 88.78; H, 5.63; N, 3.55.
[0255] Synthesis Example 26: Preparation of Compound 221
[0256]
[0257] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-221, and C-4 was replaced with an equimolar amount of C-78, yielding compound 221 (15.86 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 856.3442 (theoretical value: 856.3454). Theoretical elemental content (%) C 64 H 44 N₂O: C, 89.69; H, 5.17; N, 3.27. Measured elemental content (%): C, 89.67; H, 5.19; N, 3.25.
[0258] Synthesis Example 27: Preparation of Compound 256
[0259]
[0260] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-211, yielding compound 256 (16.44 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 842.3287 (theoretical value: 842.3297). Theoretical elemental content (%) C 63 H 42 N₂O: C, 89.76; H, 5.02; N, 3.32. Measured elemental content (%): C, 89.73; H, 5.05; N, 3.33.
[0261] Synthesis Example 28: Preparation of Compound 257
[0262]
[0263] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-78, yielding compound 257 (16.23 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 842.3286 (theoretical value: 842.3297). Theoretical elemental content (%) C 63 H 42 N₂O: C, 89.76; H, 5.02; N, 3.32. Measured elemental content (%): C, 89.72; H, 5.04; N, 3.34.
[0264] Synthesis Example 29: Preparation of Compound 260
[0265]
[0266] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-260, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-78, yielding compound 260 (17.39 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 914.3683 (theoretical value: 914.3692). Theoretical elemental content (%) C 66 H 50 N₂OSi: C, 86.62; H, 5.51; N, 3.06. Measured elemental content (%): C, 86.65; H, 5.53; N, 3.02.
[0267] Synthesis Example 30: Preparation of Compound 261
[0268]
[0269] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-186, yielding compound 261 (16.75 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 858.3080 (theoretical value: 858.3069). Theoretical elemental content (%) C 63 H 42 N2S: C, 88.08; H, 4.93; N, 3.26. Measured elemental content (%): C, 88.09; H, 4.95; N, 3.21.
[0270] Synthesis Example 31: Preparation of Compound 265
[0271]
[0272] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-265, and C-4 with an equimolar amount of C-78, yielding compound 265 (17.08 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 898.3936 (theoretical value: 898.3923). Theoretical elemental content (%) C 67 H 50 N₂O: C, 89.50; H, 5.61; N, 3.12. Measured elemental content (%): C, 89.52; H, 5.63; N, 3.10.
[0273] Synthesis Example 32: Preparation of Compound 267
[0274]
[0275] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-198, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-78, yielding compound 267 (16.11 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 847.3623 (theoretical value: 847.3611). Theoretical elemental content (%) C 63 H 37 D5N2O: C, 89.23; H, 5.59; N, 3.30. Measured elemental content (%): C, 89.22; H, 5.56; N, 3.35.
[0276] Synthesis Example 33: Preparation of Compound 276
[0277]
[0278] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-276, and C-4 with an equimolar amount of C-211, yielding compound 276 (16.50 g). HPLC analysis showed a solid purity ≥99.95%. Mass spectrometry m / z: 856.3440 (theoretical value: 856.3454). Theoretical elemental content (%) C 64 H 44 N₂O: C, 89.69; H, 5.17; N, 3.27. Measured elemental content (%): C, 89.66; H, 5.19; N, 3.29.
[0279] Synthesis Example 34: Preparation of Compound 290
[0280]
[0281] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-203, B-4 with an equimolar amount of B-290, and C-4 with an equimolar amount of C-290, yielding compound 290 (15.46 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 858.3080 (theoretical value: 858.3069). Theoretical elemental content (%) C 63 H 42 N2S: C, 88.08; H, 4.93; N, 3.26. Measured elemental content (%): C, 88.05; H, 4.96; N, 3.24.
[0282] Synthesis Example 35: Preparation of Compound 293
[0283]
[0284] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-293, yielding compound 293 (15.68 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 858.3085 (theoretical value: 858.3069). Theoretical elemental content (%) C 63 H 42 N2S: C, 88.08; H, 4.93; N, 3.26. Measured elemental content (%): C, 88.05; H, 4.95; N, 3.28.
[0285] Synthesis Example 36: Preparation of Compound 303
[0286]
[0287] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-303, B-4 with an equimolar amount of B-38, and C-4 with an equimolar amount of C-303, yielding compound 303 (15.63 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 892.3439 (theoretical value: 892.3454). Theoretical elemental content (%) C 67 H 44 N₂O: C, 90.11; H, 4.97; N, 3.14. Measured elemental content (%): C, 90.14; H, 4.95; N, 3.12.
[0288] Synthesis Example 37: Preparation of Compound 316
[0289]
[0290] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-316, and C-4 with an equimolar amount of C-316, yielding compound 316 (14.98 g). HPLC analysis showed a solid purity ≥99.91%. Mass spectrometry m / z: 843.3259 (theoretical value: 843.3250). Theoretical elemental content (%) C 62 H 41 N3O: C, 88.23; H, 4.90; N, 4.98. Measured elemental content (%): C, 88.25; H, 4.92; N, 4.95.
[0291] Synthesis Example 38: Preparation of Compound 322
[0292]
[0293] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-322, and C-4 with an equimolar amount of C-78, yielding compound 322 (16.07 g). HPLC analysis showed a solid purity ≥99.93%. Mass spectrometry m / z: 856.3443 (theoretical value: 856.3454). Theoretical elemental content (%) C 64 H 44 N₂O: C, 89.69; H, 5.17; N, 3.27. Measured elemental content (%): C, 89.65; H, 5.18; N, 3.29.
[0294] Synthesis Example 39: Preparation of Compound 390
[0295]
[0296] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-217, B-4 with an equimolar amount of B-390, and C-4 with an equimolar amount of C-390, yielding compound 390 (16.15 g). HPLC analysis showed a solid purity ≥99.97%. Mass spectrometry m / z: 896.3719 (theoretical value: 896.3705). Theoretical elemental content (%) C 67 H 40 D4N2O: C, 89.70; H, 5.39; N, 3.12. Measured elemental content (%): C, 89.73; H, 5.35; N, 3.14.
[0297] Synthesis Example 40: Preparation of Compound 433
[0298]
[0299] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-433, and C-4 with an equimolar amount of C-433, yielding compound 433 (15.70 g). HPLC analysis showed a solid purity ≥99.94%. Mass spectrometry m / z: 859.3011 (theoretical value: 859.3021). Theoretical elemental content (%) C 62 H 41 N3S: C, 86.58; H, 4.81; N, 4.89. Measured elemental content (%): C, 86.56; H, 4.85; N, 4.88.
[0300] Synthesis Example 41: Preparation of Compound 452
[0301]
[0302] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, B-4 with an equimolar amount of B-452, and C-4 with an equimolar amount of C-452, yielding compound 452 (13.59 g). HPLC analysis showed a solid purity ≥99.98%. Mass spectrometry m / z: 754.2996 (theoretical value: 754.2984). Theoretical elemental content (%) C 56 H 38 N₂O: C, 89.10; H, 5.07; N, 3.71. Measured elemental content (%): C, 89.13; H, 5.04; N, 3.73.
[0303] Synthesis Example 42: Preparation of Compound 472
[0304]
[0305] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-472, yielding compound 472 (14.91 g). HPLC analysis showed a solid purity ≥99.92%. Mass spectrometry m / z: 784.3078 (theoretical value: 784.3090). Theoretical elemental content (%) C 57 H 40 N2O2: C, 87.22; H, 5.14; N, 3.57. Measured elemental content (%): C, 87.25; H, 5.16; N, 3.54.
[0306] Synthesis Example 43: Preparation of Compound 508
[0307]
[0308] Following the method of Example 6, A-4 was replaced with an equimolar amount of A-48, and C-4 was replaced with an equimolar amount of C-508, yielding compound 508 (16.05 g). HPLC analysis showed a solid purity ≥99.96%. Mass spectrometry m / z: 855.3626 (theoretical value: 855.3613). Theoretical elemental content (%) C 64 H 45 N3: C, 89.79; H, 5.30; N, 4.91. Measured elemental content (%): C, 89.75; H, 5.33; N, 4.93.
[0309] [Device Examples]
[0310] The instruments used to test the device performance in this invention consist of a combined IVL testing system comprising testing software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter. The system was used to test the luminous efficiency of the organic electroluminescent device. The lifetime was tested using the McScience M6000 OLED lifetime testing system. The testing conditions were ambient air, room temperature, and a current density of 10 mA / cm². 2 .
[0311] [Device Example 1]
[0312] First, the glass substrate coated with ITO was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then it was dried on a hot plate heated to 120°C. After drying, it was transferred to a plasma cleaner and cleaned for 5 minutes before being transferred to a vapor deposition machine.
[0313] A vacuum evaporation method was used to deposit a 60 nm thick DNTPD as a hole injection layer on a cleaned ITO glass substrate; a 30 nm thick compound 48 as a hole transport layer was deposited on the hole injection layer; a CPB:Ir(mppy)2 = 98:2 (mass ratio) was deposited on the hole transport layer as a light-emitting layer with a thickness of 28 nm; an Alq3:Liq = 1:1 (mass ratio) was deposited on the light-emitting layer as an electron transport layer with a thickness of 32 nm; LiF was deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was deposited on the electron injection layer as a cathode with a thickness of 120 nm.
[0314]
[0315]
[0316] [Device Examples 2-20]
[0317] Compounds 72, 79, 90, 91, 182, 187, 198, 201, 203, 211, 217, 257, 260, 267, 293, 303, 433, 472, and 508 of the present invention were used to replace compound 48 in device example 1 as hole transport layer materials. Otherwise, an organic electroluminescent device was prepared using the same preparation method as in device example 1.
[0318] [Comparative Device Examples 1-3]
[0319] Compounds A, B, and C were used to replace compound 48 in device example 1 as hole transport layer materials, respectively. Otherwise, organic electroluminescent devices were prepared using the same preparation method as in device example 1.
[0320] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.
[0321] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 1-20 in the device embodiments of the present invention, and those obtained in comparative embodiments 1-3 are shown in Table 1 below.
[0322] Table 1:
[0323]
[0324]
[0325] As shown in Table 1, when the compound described in this invention is used as a hole transport layer material in an organic electroluminescent device, the device exhibits higher luminous efficiency and a longer lifespan. The compound described in this invention is a high-performance hole transport layer material.
[0326] [Device Example 21]
[0327] First, the glass substrate coated with ITO was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then it was dried on a hot plate heated to 120°C. After drying, it was transferred to a plasma cleaner and cleaned for 5 minutes before being transferred to a vapor deposition machine.
[0328] Using a vacuum evaporation method, a 60 nm thick 2-TNATA layer was deposited on a cleaned ITO glass substrate as a hole injection layer; a 55 nm thick NPB layer was deposited on the hole injection layer as a first hole transport layer; a 30 nm thick compound 4 layer was deposited on the first hole transport layer as a second hole transport layer; an ADN:TBPe ratio of 97:3 (mass ratio) was deposited on the second hole transport layer as a light-emitting layer with a thickness of 30 nm; a 30 nm thick Alq3 layer was deposited on the light-emitting layer as an electron transport layer; LiF was deposited on the electron transport layer as an electron injection layer with a thickness of 1 nm; and Al was deposited on the electron injection layer as a cathode with a thickness of 120 nm.
[0329]
[0330] [Device Examples 22-48]
[0331] Compounds 38, 48, 56, 78, 79, 91, 154, 155, 182, 187, 198, 201, 211, 217, 221, 257, 260, 267, 276, 290, 293, 303, 322, 390, 433, 472, and 508 of the present invention were used to replace compound 4 in device example 21 as the second hole transport layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 21.
[0332] [Comparative Device Examples 4-5]
[0333] Compounds A and B were used to replace compound 4 in device example 21 as the second hole transport layer material, respectively. Otherwise, an organic electroluminescent device was prepared by the same preparation method as device example 21.
[0334] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.
[0335] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 21-48 in the device embodiments of this invention, and those obtained in comparative embodiments 4-5, are shown in Table 2 below.
[0336] Table 2:
[0337]
[0338]
[0339] As shown in Table 2, when the compound described in this invention is used as the second hole transport layer material of an organic electroluminescent device, the device has higher luminous efficiency and longer lifespan. The compound described in this invention is a high-performance second hole transport layer material.
[0340] [Device Example 49]
[0341] First, the glass substrate coated with ITO / Ag / ITO was washed three times in distilled water and ultrasonically cleaned for 15 minutes. After the distilled water cleaning, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. Then it was dried on a hot plate heated to 120°C. After drying, it was transferred to a plasma cleaner and cleaned for 5 minutes before being transferred to a vapor deposition machine.
[0342] A vacuum evaporation method was used to deposit 60 nm thick 2-TNATA as a hole injection layer on a cleaned ITO glass substrate; 60 nm thick NPB was deposited as a hole transport layer on the hole injection layer; a compound CPB:Ir(mppy)2 of 98:2 (mass ratio) of 30 nm thick was deposited as a light-emitting layer on the hole transport layer; Alq3 was deposited as an electron transport layer of 30 nm thick on the light-emitting layer; LiF was deposited as an electron injection layer of 1 nm thick on the electron transport layer; Mg:Ag of 1:9 (mass ratio) of 16 nm thick was deposited as a cathode on the electron injection layer; and compound 38 of 60 nm thick was deposited as a capping layer on the cathode.
[0343]
[0344] [Device Examples 50-69]
[0345] Compounds 38, 72, 90, 154, 169, 182, 186, 211, 256, 257, 260, 261, 265, 267, 276, 316, 322, 433, 452, 472, and 508 of the present invention were used to replace compound 38 in device example 49 as the capping layer material. Otherwise, an organic electroluminescent device was prepared using the same preparation method as device example 49.
[0346] [Comparative Device Examples 6-7]
[0347] Compounds D and E were used to replace compound 38 in device example 49 as the capping material, respectively. Otherwise, the organic electroluminescent device was prepared by the same preparation method as device example 49.
[0348] A combined IVL testing system was used to test the luminous efficiency of organic electroluminescent devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using the McScience M6000 OLED lifetime testing system.
[0349] The test environment was atmospheric, and the temperature was room temperature. The luminescence characteristics test results of devices 49-69 in the device embodiments of this invention, and those obtained in comparative embodiments 6-7, are shown in Table 3 below.
[0350] Table 3:
[0351]
[0352]
[0353] As shown in Table 3, when the compound described in this invention is used as a capping material for organic electroluminescent devices, the devices exhibit higher luminous efficiency and longer lifespan. The compound described in this invention is a high-performance capping material.
[0354] It should be noted that the present invention has been specifically described with reference to specific embodiments. For those skilled in the art, various improvements and modifications can be made to the present invention without departing from the principle of the present invention, and these improvements and modifications also fall within the protection scope of the present invention.
Claims
1. A triarylamine compound, characterized in that, The triarylamine compounds have the structure shown in Formula 1. Wherein, A is selected from any one of the following groups. The R4 group, whether identical or different, is selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The c is selected from 1, 2, 3, 4, 5, 6, 7 or 8; the c2 is selected from 1, 2, 3, 4 or 5; the c3 is selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; the c6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. The B is selected from the group shown in Formula 1-2 or Formula 1-3; The Ar is selected from any one of the following groups. The R7 is the same as or different from any one of the following groups: hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, triethylsilyl, and triphenylsilyl. The number e1 is selected from 1, 2, 3, 4 or 5; the number e3 is selected from 1, 2, 3, 4, 5, 6 or 7; The v is a C atom; The R1 and R2 are the same or different and are selected from any one or a combination of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted phenyl, or two adjacent R1 are connected to each other to form a substituted or unsubstituted benzene ring, or two adjacent R2 are connected to each other to form a substituted or unsubstituted benzene ring; a is selected from 1, 2, 3 or 4; b is selected from 1, 2 or 3; The R5s, whether identical or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, or substituted or unsubstituted phenyl; the R6s, whether identical or different, are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, or substituted or unsubstituted C1-C6 alkyl; m is selected from 1 or 2; n is selected from 1 or 2. The Y0 is selected from O atom, S atom or N(Ra); the Ra is selected from any one of substituted or unsubstituted C6~C12 aryl groups; Y1 and Y2 are independently selected from O atoms or S atoms; The same or different E are selected from C (Rb) or N atoms, and at most one E is selected from N; the same or different Rb are selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1~C6 alkyl, substituted or unsubstituted phenyl, or two adjacent Rb are connected to each other to form a substituted or unsubstituted benzene ring; provided that when E is the connection site connected to L2, E is a C atom; The L1 is selected from any one of the following groups. The L2 and L3 are independently selected from single bonds or any of the following groups. The R8 group, whether identical or different, is selected from hydrogen, deuterium, halogen, cyano, or any of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; k1 is selected from 1, 2, 3, or 4; k2 is selected from 1, 2, 3, 4, 5, or 6; k3 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; k5 is selected from 0, 1, 2, or 3. The substituents represented by "substituted or unsubstituted" are selected from the following groups: deuterium, tritium, cyano, halogen, methyl, ethyl, propyl, butyl.
2. A triarylamine compound according to claim 1, characterized in that, The B group is selected from any one of the following groups. R5, R6, and Rb are independently selected from hydrogen, deuterium, or any of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl; m is selected from 1 or 2; n is selected from 1 or 2. The d1 is selected from 0, 1, 2, 3 or 4; the d2 is selected from 0, 1, 2 or 3; the d4 is selected from 0, 1, 2, 3, 4, 5 or 6.
3. A triarylamine compound according to claim 1, characterized in that, The Ar is selected from any one of the following groups. 。 4. A triarylamine compound according to claim 1, characterized in that, The L1 is independently selected from any one of the following groups. The L2 and L3 are selected from any one of the following groups. 。 5. A triarylamine compound, characterized in that, The triarylamine compounds are selected from the following structures. 。 6. An organic electroluminescent device, characterized in that, The device comprises an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, and an electron transport region. The light-emitting layer is located between the anode and the cathode, the hole transport region is located between the anode and the light-emitting layer, and the electron transport region is located between the light-emitting layer and the cathode. The hole transport region includes a hole injection layer and a hole transport layer. The hole injection layer is located between the anode and the light-emitting layer, and the hole transport layer is located between the hole injection layer and the light-emitting layer. The hole transport layer comprises any one or more of the triarylamine compounds according to any one of claims 1-5. Alternatively, the organic layer is located on the side of the cathode opposite to the anode, and the organic layer includes a capping layer, which comprises any one or more of the triarylamine compounds according to any one of claims 1-5.