Arylamine compounds, organic electroluminescent devices and electronic devices

Abstract

This application relates to the field of organic electroluminescent materials technology, providing an aromatic amine compound and an organic electroluminescent device and electronic device containing the same. The aromatic amine compound of this application contains a core structure of 7-phenyl-naphtho[1,2-c]carbazole. When this compound is used as a hole-transporting material in a hybrid host material, it can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance the luminous efficiency and lifetime of the device.

Description

Technical Field

[0001] This application relates to the field of organic electroluminescent materials technology, and more particularly to aromatic amine compounds and organic electroluminescent devices and electronic devices containing the same. Background Technology

[0002] With the development of electronic technology and the advancement of materials science, the application range of electronic components used to achieve electroluminescence or photoelectric conversion is becoming increasingly wide. Organic electroluminescent devices (OLEDs) typically include: a cathode and an anode positioned opposite each other, and a functional layer disposed between the cathode and the anode. This functional layer consists of multiple organic or inorganic film layers and generally includes an organic light-emitting layer, a hole transport layer, and an electron transport layer. When a voltage is applied to the cathode and anode, an electric field is generated between the two electrodes. Under the influence of the electric field, electrons on the cathode side move towards the electroluminescent layer, and holes on the anode side also move towards the light-emitting layer. Electrons and holes combine in the electroluminescent layer to form excitons. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light.

[0003] The most significant challenges in existing organic light-emitting diodes (OLEDs) lie in their lifespan and efficiency. With the increasing size of displays, the driving voltage also rises. Research aimed at improving the performance of OLEDs includes reducing the driving voltage, increasing luminous efficiency, and extending lifespan. To enhance OLED performance, multi-layered sandwich structures are typically employed in device design, consisting of an anode, a cathode, and multiple organic functional layers forming a complete device. The host material for the light-emitting layer can be one or more materials. This material is capable of accepting and combining positively charged holes and negatively charged electrons for efficient energy transfer, typically possessing a high first triplet energy level, making it a crucial component of organic light-emitting diodes. Continued research and development of new host materials for the light-emitting layer are necessary to further improve the performance of organic light-emitting diodes. Summary of the Invention

[0004] In view of the above-mentioned problems existing in the prior art, the purpose of this application is to provide an aromatic amine compound and an organic electroluminescent device and electronic device containing the same, wherein the aromatic amine compound used in the organic electroluminescent device can improve the performance of the device.

[0005] According to a first aspect of this application, an aromatic amine compound is provided, the aromatic amine compound having the structure shown in Formula 1:

[0006] in,

[0007] Among them, L, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0008] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0009] The substituents of L, L1, L2, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 3 to 12 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.

[0010] According to a second aspect of this application, an organic electroluminescent device is provided, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising the aforementioned aromatic amine compound.

[0011] According to a third aspect of this application, an electronic device is provided, including the organic electroluminescent device described in the second aspect.

[0012] The compound structure of this application contains the core structure of 7-phenyl-naphtho[1,2-c]carbazole, and the core is located at a specific position (position 13). This compound is linked to an aromatic amine hole transport fragment, serving as a hole transport-type luminescent host material. On one hand, the unique fusion mechanism of 7-phenyl-naphtho[1,2-c]carbazole ensures that its core possesses a suitable first excited triplet energy level, making it suitable as a fragment for luminescent host material. On the other hand, the core structure of 7-phenyl-naphtho[1,2-c]carbazole has a large conjugated system; linking it to an aromatic amine hole transport fragment at position 13 enhances intermolecular forces and improves the hole mobility of the compound. When this compound is used as a hole transport-type host material in a hybrid luminescent host material, it can improve carrier balance in the luminescent layer, broaden the carrier recombination region, improve exciton generation and utilization efficiency, and enhance device luminescence efficiency and lifetime. Attached Figure Description

[0013] The accompanying drawings are provided to further understand this application and form part of the specification. They are used together with the following detailed description to explain this application, but do not constitute a limitation thereof.

[0014] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device according to one embodiment of this application.

[0015] Figure 2 This is a schematic diagram of the structure of an electronic device according to one embodiment of this application.

[0016] Figure Labels

[0017] 100, Anode 200, Cathode 300, Functional Layer 310, Hole Injection Layer

[0018] 321. First hole transport layer; 322. Luminescence adjustment layer; 330. Organic light-emitting layer; 340. Electron transport layer

[0019] 350, Electron injection layer 320, Hole transport layer 400, Electronic device Detailed Implementation

[0020] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make this application more comprehensive and complete, and to fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of this application.

[0021] In a first aspect, this application provides an aromatic amine compound having the structure shown in Formula 1:

[0022]

[0023] Among them, L, L1 and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms.

[0024] Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;

[0025] The substituents of L, L1, L2, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, cyano, halogen group, alkyl with 1 to 10 carbon atoms, haloalkyl with 1 to 10 carbon atoms, deuteralkyl with 1 to 10 carbon atoms, alkoxy with 1 to 10 carbon atoms, alkylthio with 1 to 10 carbon atoms, trialkylsilyl with 3 to 12 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 3 to 12 carbon atoms, and cycloalkyl with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.

[0026] In this application, the terms "optional" and "optionally" mean that the events or circumstances described below may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently without forming a ring. "Any two adjacent" can include having two substituents on the same atom, and can also include having one substituent on each of two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spirocyclic ring with the atom they are connected to; when there is one substituent on each of two adjacent atoms, the two substituents can fuse into a ring.

[0027] In this application, the terms "optionally", "preferredly", and "in some embodiments" have the same meaning.

[0028] In this application, the descriptive phrases "each...independently is," "...each independently is," and "...each independently is" are interchangeable and should be interpreted broadly. They can mean either that the specific options expressed by the same symbol in different groups do not affect each other, or that the specific options expressed by the same symbol in the same group do not affect each other. For example, In this formula, each q is independently 0, 1, 2 or 3, and each R is independently selected from hydrogen, deuterium, fluorine or chlorine. The meaning is as follows: Formula Q-1 indicates that there are q substituents R on the benzene ring. Each R can be the same or different, and the options of each R do not affect each other. Formula Q-2 indicates that there are q substituents R on each benzene ring of biphenyl. The number q of substituents R on the two benzene rings can be the same or different, and each R can be the same or different. The options of each R do not affect each other.

[0029] In this application, the term "substituted or unsubstituted" means that the functional group described after the term may or may not have substituents (hereinafter, for ease of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an aryl group without a substituent. The aforementioned substituents, i.e., Rc, can be, for example, deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0030] In this application, "multiple" means two or more, such as two, three, four, five, six, etc.

[0031] In this application, the number of carbon atoms in a substituted or unsubstituted functional group refers to the total number of carbon atoms in that group and all its substituents. For example, if L1 is a substituted arylene with 12 carbon atoms, then the total number of carbon atoms in the arylene and its substituents is 12.

[0032] The hydrogen atoms in the compound structure of this application include various isotopes of hydrogen, such as hydrogen (H), deuterium (D), or tritium (T).

[0033] In the structural formula of the compound in this application, "D" indicates deuteration.

[0034] In this application, saturated or unsaturated 5- to 13-membered carbon rings refer to carbon rings containing 5 to 13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene rings, fluorene rings, etc.

[0035] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. An aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, an aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups conjugated by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl group conjugated by carbon-carbon bonds, or two or more fused-ring aryl groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as aryl groups in this application. Fused-ring aryl groups may include, for example, bicyclic fused aryl (e.g., naphthyl), tricyclic fused aryl (e.g., phenanthrene, fluorene, anthracene), etc. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, fluorenyl, spirodifluorenyl, anthracene, phenanthryl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, triphenylene, perylene, benzo[9,10]phenanthryl, pyrene, benzofluoranthryl, etc. Base, etc.

[0036] In this application, the term "arylene" refers to a divalent group formed by the further loss of one or more hydrogen atoms from an aryl group.

[0037] In this application, terphenyl includes

[0038] In this application, the substituted or unsubstituted aryl (arylene) group can have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, or 30 carbon atoms. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms; in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 25 carbon atoms; in still other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 18 carbon atoms; and in yet another embodiment, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group with 6 to 15 carbon atoms.

[0039] In this application, the fluorene group can be substituted by one or more substituents. When the fluorene group is substituted, the substituted fluorene group can be: etc., but not limited to this.

[0040] In this application, the aryl groups used as substituents for L, L1, L2, Ar1, and Ar2 are, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, etc.

[0041] In this application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms. The heteroatoms can be one or more of B, O, N, P, Si, Se, and S. A heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group. In other words, a heteroaryl group can be a single aromatic ring system or a system of multiple aromatic rings connected by carbon-carbon bonds in a conjugated manner, and any aromatic ring system can be an aromatic monocyclic ring or an aromatic fused ring. For example, heteroaryl groups may include, but are not limited to, thiopheneyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxazinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolinyl, indolyl, carbazoleyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, benzocarbazoleyl, benzothiaphenyl, dibenzothiaphenyl, thiaphenothiaphenyl, benzofuranyl, phenanthrololinyl, isoxazolyl, thiadiazolyl, phenthiaazinyl, silfluorenyl, dibenzofuranyl, and N-phenylcarbazoleyl, N-pyridylcarbazoleyl, N-methylcarbazoleyl, etc.

[0042] In this application, the term "hybrid aryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a heteroaryl group.

[0043] In this application, the number of carbon atoms in the substituted or unsubstituted heteroaryl (hybrid aryl) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, or 20. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 30; in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 3 to 18; and in still other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl with a total carbon number of 12 to 18.

[0044] In this application, alkyl groups having 1 to 10 carbon atoms can include straight-chain alkyl groups having 1 to 10 carbon atoms and branched alkyl groups having 3 to 10 carbon atoms. The number of carbon atoms in an alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.

[0045] In this application, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.

[0046] In this application, specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, etc.

[0047] In this application, alkyl halotype refers to alkyl halotype substituted with halogen, and specific examples of alkyl halotype include, but are not limited to, trifluoromethyl halotype.

[0048] In this application, deuterated alkyl refers to one or more deuterated alkyl groups, and specific examples of deuterated alkyl include, but are not limited to, trideuterated methyl.

[0049] In this application, the number of carbon atoms in cycloalkyl groups with 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

[0050] In this application, the number of carbon atoms in the deuterated alkyl group is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of deuterated alkyl groups include, but are not limited to, trideuterated methyl.

[0051] In this application, the number of carbon atoms in the alkyl halogroup is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of alkyl halogroups include, but are not limited to, trifluoromethyl.

[0052] In this application, It refers to the chemical bond that connects with other groups.

[0053] In this application, the non-positioned connecting key refers to the single bond extending from the loop system. This indicates that one end of the linker can connect to any position in the ring system it traverses, and the other end connects to the rest of the compound molecule. For example, as shown in equation (f) below, the naphthyl group represented by equation (f) is connected to other positions in the molecule through two non-positional linkers that traverse the bicyclic ring. This means that any possible connection mode shown in equations (f-1) to (f-10) is included.

[0054]

[0055] For another example, as shown in equation (X'), the dibenzofuran group represented by equation (X') is connected to other positions in the molecule via a non-positional linker extending from the middle of one side of the benzene ring. This means that any possible connection mode shown in equations (X'-1) to (X'-4) is included.

[0056]

[0057] In this application, a non-orienting substituent refers to a substituent connected by a single bond extending from the center of the ring system, indicating that the substituent can be attached to any possible position in the ring system. For example, as shown in equation (Y) below, the substituent R' represented by equation (Y) is connected to the quinoline ring by a non-orienting linking bond, which means that it includes any possible connection mode shown in equations (Y-1) to (Y-7):

[0058]

[0059] In some embodiments, L, L1, and L2 may be the same or different, and each is independently selected from single bonds, substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, or substituted or unsubstituted heteroaryl groups having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0060] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, cyano, halogen group, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms, deuterated alkyl with 1 to 4 carbon atoms, trialkylsilyl or phenyl with 3 to 7 carbon atoms.

[0061] In some embodiments, L, L1, and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

[0062] Optionally, the substituents in L, L1 and L2 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0063] In some embodiments, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

[0064]

[0065] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0066]

[0067] In some embodiments, L1 and L2 may be the same or different, and each is independently selected from the group consisting of single bonds or the following groups:

[0068]

[0069] In some embodiments, L is selected from the group consisting of single bonds or the following groups:

[0070]

[0071] In some embodiments, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, or 30 carbon atoms.

[0072] In some embodiments, Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

[0073] Optionally, the substituents in Ar1, Ar2 and Ar3 are each independently selected from deuterium, halogen groups, cyano, haloalkyl with 1 to 4 carbon atoms, deuteralkyl with 1 to 4 carbon atoms, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, aryl with 6 to 15 carbon atoms, heteroaryl with 5 to 12 carbon atoms, trialkylsilyl with 3 to 7 carbon atoms or deuteralkyl with 6 to 15 carbon atoms. Optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0074] In some embodiments, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazole.

[0075] Optionally, the substituents in Ar1, Ar2 and Ar3 may be the same or different, and each may be independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl.

[0076] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0077]

[0078] In some embodiments, Ar3 is selected from the following groups:

[0079]

[0080] In some embodiments, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

[0081]

[0082]

[0083] In some embodiments, Ar3 is selected from the following groups:

[0084]

[0085] In some implementations... They may be the same or different, and each is independently selected from the following groups:

[0086]

[0087] In some implementations, in Equation 1, Selected from the following groups:

[0088]

[0089]

[0090] In some embodiments, the aromatic amine compound is selected from the group consisting of:

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] In a second aspect, this application provides an organic electroluminescent device, including an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer contains the aromatic amine compound described in the first aspect of this application.

[0104] The aromatic amine compounds provided in this application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of organic electroluminescent devices.

[0105] Optionally, the functional layer further includes a hole transport region, which includes a hole transport layer (also known as a first hole transport layer) and a light emission adjustment layer (also known as a second hole transport layer or a hole auxiliary layer). The hole transport layer is located between the anode and the organic light emission layer, and the light emission adjustment layer is located between the first hole transport layer and the organic light emission layer.

[0106] Optionally, the functional layer further includes a light-emitting layer, which comprises a light-emitting layer host material and a dopant material, wherein the light-emitting layer host material comprises the aromatic amine compound of this application.

[0107] In some embodiments, the main material of the light-emitting layer is composed of the aromatic amine compound provided in this application and other materials.

[0108] According to one specific embodiment, the organic electroluminescent device, such as Figure 1 As shown, it includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a light-emitting adjustment layer 322, an organic light-emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are stacked in sequence.

[0109] In this application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode comprising indium tin oxide (ITO) as the anode is included.

[0110] In this application, the hole transport layer and the hole conditioning layer may each include one or more hole transport materials. The hole transport materials may be selected from carbazole polymers, carbazole-linked triarylamine compounds, or other types of compounds, specifically from the compounds listed below or any combination thereof:

[0111]

[0112]

[0113] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0114] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.

[0115] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst-like arylamine compounds, phthalocyanine derivatives, or other materials, and this application does not impose any special limitations on this. The material of the hole injection layer 310 is selected, for example, from the following compounds or any combination thereof;

[0116]

[0117]

[0118] In one embodiment of this application, the hole injection layer 310 is composed of PD and HT-1.

[0119] Optionally, the organic light-emitting layer 330 may be composed of a single light-emitting material, or it may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material. Holes and electrons injected into the organic light-emitting layer 330 can recombine in the organic light-emitting layer 330 to form excitons. The excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0120] The host material of the organic light-emitting layer 330 may comprise metal chelating compounds, bis(styrene) derivatives, aromatic amine derivatives, dibenzofuran derivatives, or other types of materials. The host material of the organic light-emitting layer 330 may be one compound, or a combination of two or more compounds. Optionally, the host material may comprise the aromatic amine compounds of this application.

[0121] The guest material of the organic light-emitting layer 330 can be a compound with a condensed aryl ring or its derivative, a compound with a heteroaryl ring or its derivative, an aromatic amine derivative, or other materials; this application does not impose any special limitations on this. The guest material is also called a dopant or dopant. According to the type of light emission, it can be divided into fluorescent dopant and phosphorescent dopant. Specific examples of phosphorescent dopant include, but are not limited to,

[0122]

[0123]

[0124] In one embodiment of this application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the host material of the organic light-emitting layer 330 comprises RH-N. And the compounds of this application. The guest material may be, for example, RD-1.

[0125] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials. The electron transport materials may be selected from, but are not limited to, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials; this application does not impose any special limitations on this. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0126]

[0127] In one embodiment of this application, the electron transport layer 340 is composed of ET and LiQ.

[0128] In this application, the cathode 200 includes a cathode material that has a small work function and facilitates electron injection into the functional layers. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver may be included as the cathode.

[0129] Optionally, an electron injection layer 350 is further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include complexes of alkali metals and organic materials. In one embodiment of this application, the electron injection layer 350 includes ytterbium (Yb).

[0130] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0131] According to one implementation method, such as Figure 2 As shown, the provided electronic device is electronic device 400, which includes the aforementioned organic electroluminescent device. Electronic device 400 can be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as including but not limited to computer screens, mobile phone screens, televisions, electronic paper, emergency lighting, optical modules, etc.

[0132] The following examples illustrate the synthesis method of the aromatic amine compounds of this application, but this application is not limited thereto.

[0133] Synthesis Examples

[0134] Those skilled in the art will recognize that the chemical reactions described herein can be suitably used to prepare many of the aromatic amine compounds of this application, and other methods for preparing the compounds of this application are considered to be within the scope of this application. For example, the synthesis of those non-illustrative compounds according to this application can be successfully accomplished by those skilled in the art through modification methods, such as appropriately protecting interfering groups, utilizing other known reagents besides those described herein, or making some conventional modifications to the reaction conditions. Compounds for which synthetic methods are not mentioned in this application are commercially available starting materials.

[0135] Synthesis of Sub-a1:

[0136]

[0137] Under a nitrogen atmosphere, RM-1 (11.35 g, 55 mmol), RM-2 (11.20 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (120 mL), anhydrous ethanol (30 mL), and deionized water (30 mL) were added sequentially to a 500 mL three-necked flask. Stirring and heating were started, and the mixture was refluxed for 8 h. After the system cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (8.71 g, yield 57%). Synthesis of Sub-b1:

[0138]

[0139] Under a nitrogen atmosphere, Sub-b1 (39.75 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol), and anhydrous tetrahydrofuran (500 mL) were added sequentially to a 1000 mL three-necked flask. The system was cooled to 0 °C using an ice-water bath. Then, an anhydrous tetrahydrofuran solution of potassium tert-butoxide (1 M, 220 mL) was slowly added dropwise. After the addition was complete, the system was slowly heated to room temperature, and the reaction was stirred for 6 h. The reaction solution was poured into 1000 mL of deionized water and extracted with ethyl acetate (250 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain a solid (29.51 g, yield 68%).

[0140] Synthesis of Sub-c1:

[0141]

[0142] Under a nitrogen atmosphere, Sub-b1 (39.72 g, 119 mmol), Eaton reagent (4.5 mL), and chlorobenzene (400 mL) were added sequentially to a 1000 mL three-necked flask. The mixture was heated to reflux and stirred for 4 h. After the reaction system cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water, neutralized with saturated sodium hydroxide solution, and then extracted with dichloromethane (250 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid (20.47 g, yield 57%).

[0143] Synthesis of Sub-d1:

[0144]

[0145] Under a nitrogen atmosphere, Sub-Cl (15.10 g, 50 mmol), iodobenzene (12.24 g, 60 mmol), cuprous iodide (1.90 g, 10 mmol), 18-crown ether-6 (1.32 g, 5 mmol), 1,10-phenanthroline (3.96 g, 20 mmol), potassium carbonate (15.20 g, 110 mmol), and N,N-dimethylformamide (250 mL) were added sequentially to a 500 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After the system cooled to room temperature, the reaction solution was poured into 500 mL of deionized water, filtered, and the filtrate was collected. The filtrate was dissolved in dichloromethane and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a gray-green solid (14.55 g; yield 77%).

[0146] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d6 were synthesized by replacing iodobenzene with reactant A shown in Table 1.

[0147] Table 1: Synthesis of Sub-d2 to Sub-d6

[0148]

[0149] Synthesis of Sub-e1:

[0150]

[0151] Under a nitrogen atmosphere, Sub-d1 (18.90 g, 50 mmol), pinacol diborate (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol), and 1,4-dioxane (150 mL) were added sequentially to a 500 mL three-necked flask. The mixture was stirred and heated until it reached 40 °C. Then, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The mixture was then heated to reflux and stirred overnight. After the system cooled to room temperature, 200 mL of water was added to the system, and the mixture was stirred thoroughly for 30 min. The mixture was then filtered under reduced pressure. The filter cake was washed with deionized water until neutral, then dissolved in 100 mL of dichloromethane and dried with anhydrous sodium sulfate. After filtration, the organic phase was distilled under reduced pressure to remove the solvent and obtain the crude product. The crude product was dissolved in 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-e1 (16.90 g, yield 72%) was obtained.

[0152] Synthesis of Sub-f1:

[0153]

[0154] Under a nitrogen atmosphere, m-chlorobromobenzene (9.57 g, 50 mmol), Sub-e1 (25.82 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (220 mL), anhydrous ethanol (55 mL), and deionized water (55 mL) were added sequentially to a 1000 mL three-necked flask. Stirring and heating were initiated, and the mixture was refluxed for 8 h. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid, Sub-f1 (18.61 g, yield 82%).

[0155] Referring to the synthesis of Sub-f1, Sub-f2 to Sub-f7 were synthesized by replacing reactant B shown in Table 2.

[0156] Table 2: Synthesis of Sub-f2 to Sub-f7

[0157]

[0158]

[0159] Synthesis of compound 3:

[0160]

[0161] Under a nitrogen atmosphere, Sub-d1 (9.45 g, 25 mmol), RM-3 (8.84 g, 27.5 mmol), tris(dibenzylacetone)dipalladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol), and xylene (120 mL) were added sequentially to a 250 mL three-necked flask. The mixture was heated to reflux and stirred overnight. After cooling to room temperature, the mixture was extracted with dichloromethane (100 mL × 3 times). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the solvent was removed by vacuum distillation to obtain the crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give a white solid compound 3 (13.75 g; yield 83%, m / z = 663.28 [M+H]). + ).

[0162] Referring to the synthetic method of compound 3, reactant C shown in Table 3 was used to replace Sub-d1, and reactant D was used to replace RM-3 to synthesize the compounds of this application shown in Table 3.

[0163] Table 3 Synthesis of the compounds in this application

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172] NMR data for some compounds:

[0173] NMR of Compound 36: 1H-NMR (400MHz, CD2Cl2) δppm: 8.25-8.18(m,2H),8.11(d,1H),7.81(d,1H),7.69(d,1H),7.64-7.58(m, 2H),7.55-7.48(m,10H),7.47-7.25(m,12H),7.21-7.12(m,5H),6.94(s,1H),6.62(d,1H),6.43(d,2H).

[0174] Fabrication and evaluation of organic electroluminescent devices:

[0175] This invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer between the anode and the cathode, wherein the organic layer comprises the aforementioned organic compound of this invention. The organic electroluminescent device of this invention will now be described in detail through embodiments. However, the following embodiments are merely examples of this invention and are not intended to limit the invention.

[0176] Example 1: Red Organic Electroluminescent Device

[0177] First, anodizing pretreatment is performed through the following process: [The process is repeated in the original text, so the translation is incomplete.] On the ITO / Ag / ITO substrate, surface treatment is performed using ultraviolet ozone and O2:N2 plasma to increase the work function of the anode. Alternatively, organic solvents can be used to clean the surface of the ITO substrate to remove impurities and oil stains.

[0178] On the experimental substrate (anode), PD:HT-1 was co-deposited at a deposition rate of 2%:98% to form a thickness of [missing information]. A hole injection layer (HIL) is formed, and then HT-1 is vacuum-deposited on the hole injection layer to form a thickness of [missing information]. A hole transport layer. Compound HT-2 is vacuum-deposited onto the hole transport layer to form a layer with a thickness of [missing information]. Hole auxiliary layer.

[0179] Next, on the hole-assisted layer, compound 3:RH-N:RD was co-deposited in a ratio of 49%:49%:2% to form a layer with a thickness of [missing information]. The red light emitting layer (EML).

[0180] On the light-emitting layer, compounds ET and LiQ are co-deposited at a 1:1 evaporation rate to form... A thick electron transport layer (ETL) is formed by depositing Yb onto the electron transport layer to create a layer with a thickness of [thickness value missing]. An electron-injected layer (EIL) was formed, and then magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum-deposited onto the electron-injected layer to form a layer with a thickness of [missing information]. The cathode.

[0181] Furthermore, the vacuum evaporation thickness on the aforementioned cathode is [missing information]. The CP is used as a capping layer to complete the fabrication of the red organic electroluminescent device.

[0182] Examples 2-54

[0183] Except that, when fabricating the light-emitting layer, compound X in Table 4 is used instead of compound 3 in Example 1, the organic electroluminescent device is prepared using the same method as in Example 1.

[0184] Comparative Examples 1-4

[0185] Except that, when fabricating the light-emitting layer, compounds A, B, C, and D were used instead of compound 1 in Example 1, the organic electroluminescent device was prepared using the same method as in Example 1.

[0186] The structures of the materials used in the comparative and example studies for fabricating organic electroluminescent devices are as follows:

[0187]

[0188] The organic electroluminescent devices prepared in Examples 1-54 and Comparative Examples 1-4 were subjected to performance tests, specifically at 10 mA / cm². 2 The IVL performance of the device was tested under the specified conditions. The lifetime of the T95 device was 20 mA / cm. 2 The test was conducted under the specified conditions, and the test results are shown in Table 4 below.

[0189] Table 4

[0190]

[0191]

[0192] Referring to Table 4 above, when the compounds of the present invention are used as the main material of the light-emitting layer of red organic electroluminescent devices, compared with Comparative Examples 1 to 4, the luminous efficiency (Cd / A) of the devices in Examples 1 to 54 is increased by at least 12.4%, and the T95 lifetime is increased by at least 11.5%.

Claims

1. An aromatic amine compound, characterized in that, The aromatic amine compound has the structure shown in Formula 1: L, L1 and L2 are each independently selected from single bonds, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted or unsubstituted phenanthylene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl. The substituents in L, L1, and L2 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, or phenyl. Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 7 to 18 carbon atoms; The substituents in Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl, or naphthyl.

2. The aromatic amine compound according to claim 1, wherein, L1 and L2 are each independently selected from the group consisting of single bonds or the following groups:

3. The aromatic amine compound according to claim 1, wherein, L is selected from the group consisting of single bonds or the following groups:

4. The aromatic amine compound according to claim 1, wherein, Ar1, Ar2, and Ar3 are each independently selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms.

5. The aromatic amine compound according to claim 1, wherein, Ar1, Ar2, and Ar3 may be the same or different, and each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirodifluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted carbazolyl.

6. The aromatic amine compound according to claim 1, wherein, Ar1 and Ar2 may be the same or different, and each is independently selected from the following groups:

7. The aromatic amine compound according to claim 1, wherein, Ar3 is selected from the following groups:

8. The aromatic amine compound according to claim 1, wherein, They may be the same or different, and each is independently selected from the following groups:

9. The aromatic amine compound according to claim 1, wherein, In Equation 1, Selected from the following groups:

10. The aromatic amine compound according to claim 1, wherein, The aromatic amine compound is selected from the group consisting of the following compounds:

11. An organic electroluminescent device, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises an aromatic amine compound as described in any one of claims 1 to 10.

12. The organic electroluminescent device according to claim 11, wherein, The functional layer includes a light-emitting layer, which comprises a host material and a guest material; the host material generally contains the aromatic amine compound.

13. An electronic device, characterized in that, Including the organic electroluminescent device as described in claim 11 or 12.

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