Arylamine compound, organic electroluminescent device, and electronic apparatus

Abstract

The present invention relates to the technical field of organic electroluminescent materials, and provides an arylamine compound and an organic electroluminescent device comprising same, and an electronic apparatus. The arylamine compound comprises a phenanthronaphthofuran parent nucleus structure. When the compound is used as a hole transport-type host material in a hybrid host material, the carrier balance in a light-emitting layer can be improved, a carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, the light-emitting efficiency of a device can be improved, and the service life of the device can be prolonged.

Description

Arylamine compound, organic electroluminescent device and electronic device

[0001] Cross-reference to related applications

[0002] This application claims priority to Chinese patent application No. CN202410721035.8, filed on June 4, 2024, the contents of which are incorporated herein in their entirety. TECHNICAL FIELD

[0003] The present application relates to the technical field of organic electroluminescent materials, in particular to an arylamine compound, an organic electroluminescent device comprising the same and an electronic device. BACKGROUND

[0004] With the development of electronic technology and the progress of material science, the application range of electronic components and devices for realizing electroluminescence or photoelectric conversion is more and more extensive. An organic electroluminescent device (OLED) generally comprises a cathode and an anode arranged oppositely, and a functional layer arranged between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally comprises an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the cathode and the anode, an electric field is generated between the two electrodes. Under the action of the electric field, electrons on the cathode side move to the electroluminescent layer, and holes on the anode side also move to the electroluminescent layer. The electrons and holes combine in the electroluminescent layer to form excitons. The excitons in the excited state release energy outward, thereby causing the electroluminescent layer to emit light.

[0005] The most important problems in the existing organic electroluminescent device are the service life and the efficiency. With the large-area display, the driving voltage is also increased. The researches on improving the performance of the OLED light-emitting device include: reducing the driving voltage of the device, improving the light-emitting efficiency of the device, and improving the service life of the device, etc. In order to improve the performance of the OLED device, a multi-layer sandwich structure is generally adopted when designing the device structure, i.e. the anode, the cathode and the multi-layer organic functional layer together form a complete device. The light-emitting layer host material can be one or more. The host material is a material capable of accepting positively charged hole carriers and negatively charged electron carriers and combining them for effective energy transfer. It generally has a high first triplet state energy level and is a very important part of the organic electroluminescent device. It is necessary to continue to develop new light-emitting layer host materials to further improve the performance of the organic electroluminescent device. SUMMARY

[0006] In view of the above problems existing in the prior art, the purpose of the present application is to provide an arylamine compound, an organic electroluminescent device comprising the same and an electronic device. The arylamine compound is used in an organic electroluminescent device, which can improve the performance of the device.

[0007] According to a first aspect of the present application, there is provided an arylamine compound having a structure represented by Formula 1:

[0008] wherein ring A is a phenanthrene ring;

[0009] L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0010] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0011] Substituents of L, L1, L2, Ar1and Ar2are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring;

[0012] each R1and R2are the same or different, and each is independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, or a phenyl group;

[0013] n1 represents the number of R1, and n1 is selected from 0, 1, 2, 3, 4, 5, or 6;

[0014] n2 represents the number of R2, and n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0015] According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the arylamine compound of the first aspect.

[0016] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.

[0017] In some embodiments, the organic electroluminescent device is selected from a red organic electroluminescent device.

[0018] The compound of the present application contains a naphthophenanthroliguanamine parent structure in the structure of the compound, which is connected with an aromatic amine hole transport segment, and serves as a hole transport type red light host material. First, the naphthophenanthroliguanamine parent nucleus has a relatively suitable first excited triplet state energy level, which is suitable as a segment of a red light host material. Second, the parent structure has a large conjugated system, which can enhance the intermolecular force after being connected with the aromatic amine hole transport segment, and improve the hole transport rate of the compound. Third, when the aromatic amine is connected to the parent nucleus, the molecular torsion degree is large, which can endow the compound of the present application with good film forming property. When the compound of the present application is used as a hole transport type material in a mixed type red light host material, the carrier balance in the light emitting layer can be improved, the carrier recombination area can be widened, the excitation generation and utilization efficiency can be improved, and the light emitting efficiency and the service life of the device can be improved. BRIEF DESCRIPTION OF DRAWINGS

[0019] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used together with the following detailed description to explain the present application, but do not constitute a limitation on the present application.

[0020] FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.

[0021] FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.

[0022] Reference numerals 100, anode 200, cathode 300, functional layer 310, hole injection layer 321, first hole transport layer 322, light emitting adjustment layer 330, organic light emitting layer 340, electron transport layer 350, electron injection layer 320, hole transport layer 400, electronic device DETAILED DESCRIPTION

[0023] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in various forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be more thorough and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics can be combined in one or more embodiments in any suitable manner. In the following description, numerous specific details are provided to give a sufficient understanding of embodiments of the present application.

[0024] In a first aspect, the present application provides an aromatic amine compound, which has a structure shown by formula 1:

[0025] wherein ring A is a phenanthrene ring;

[0026] L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0027] Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[0028] the substituents of L, L1, L2, Ar1and Ar2are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring;

[0029] each R1and R2are the same or different, and each is independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, or a phenyl group;

[0030] n1 represents the number of R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6;

[0031] n2 represents the number of R2, and n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

[0032] In the present application, the term “optionally” or “optionally” means that the event or environment described subsequently can or can not occur. For example, “optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring” includes the scenario that any two adjacent substituents form a ring, and the scenario that any two adjacent substituents each independently exist without forming a ring. “Any two adjacent” can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein when two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; and when one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.

[0033] In the present application, the term “optionally” or “optionally” means that the event or environment described subsequently can or can not occur. For example, “optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring” includes the scenario that any two adjacent substituents form a ring, and the scenario that any two adjacent substituents each independently exist without forming a ring. “Any two adjacent” can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein when two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; and when one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.

[0034] In the present application, the description mode "each of … is independently" can be interchangeable with "… is respectively independently" and "… is each independently", and should be interpreted in a broad sense. It can mean that the specific options expressed by the same symbols in different groups do not affect each other, or it can mean that the specific options expressed by the same symbols in the same group do not affect each other. For example, wherein each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, chlorine, and the meaning is that: formula Q-1 represents 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 represents that there are q substituents R" on each benzene ring of the biphenyl, the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.

[0035] In the present application, the term "substituted or unsubstituted" means that the functional groups described after the term can have or not have substituents (hereinafter, for the sake of description, the substituents will be collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl with substituents Rc or aryl without substituents. The above-mentioned substituents, i.e. Rc, for example, can be deuterium, fluorine, cyano, halogen group, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, halogenated alkyl, deuterated alkyl, alkoxy, alkylthio, cycloalkyl, etc. The number of substituents can be one or more.

[0036] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.

[0037] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms of the group and all substituents thereon. For example, if L1 is a substituted arylene group with a carbon atom number of 12, the total number of carbon atoms of the arylene group and all substituents thereon is 12.

[0038] In the structure of the compounds of the present application, the hydrogen atoms include various isotopes of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0039] In the structural formula of the compounds of the present application, "D" represents deuterium.

[0040] In the present application, a saturated or unsaturated 5-13 membered carbocyclic ring refers to a carbon ring containing 5-13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.

[0041] In the present application, an aryl group refers to an optionally functionalized or substituted group derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group linked by carbon-carbon bonds, two or more fused ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by carbon-carbon bonds can also be considered as an aryl group in the present application. Among them, the fused ring aryl group can include, for example, a bicyclic fused aryl group (e.g., naphthyl), a tricyclic fused aryl group (e.g., phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl anthryl, phenanthryl, biphenylyl, terphenylyl, quaterphenylyl, quinquephenylyl, triphenylyenyl pyrenyl, benzophenanthryl, chrysenyl,

[0042] In the present application, the arylene group referred to herein refers to a divalent group formed by further losing one or more hydrogen atoms from the aryl group.

[0043] In the present application, the terphenylyl group includes

[0044] In the present application, the number of carbon atoms of the substituted or unsubstituted aryl (arylene) group can be 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. In some embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted aryl group is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0045] In the present application, the fluorenyl group can be substituted by 1 or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group can be, for example, but is not limited to:

[0046] In the present application, the aryl group as a substituent of L, L1, L2, Ar1, and Ar2 is, for example, but not limited to, phenyl, naphthyl, phenanthryl, biphenylyl, fluorenyl, dimethylfluorenyl, and the like.

[0047] ​​In the present application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms in the ring, and the heteroatoms can be one or more of B, O, N, P, Si, Se, and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, the heteroaryl group can include a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzcabazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0048] In the present application, a heteroaryl group refers to a monovalent aromatic ring or its derivative containing 1, 2, 3, 4, 5, or 6 heteroatoms in the ring, and the heteroatoms can be one or more of B, O, N, P, Si, Se, and S. The heteroaryl group can be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group can be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, the heteroaryl group can include a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzcabazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothienyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silafluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0049] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) group 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 group is a substituted or unsubstituted heteroaryl group having a total of 3 to 30 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total of 3 to 18 carbon atoms, in other embodiments, the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted heteroaryl group having a total of 12 to 18 carbon atoms.

[0050] In the present application, the heteroaryl group as a substituent of L, L1, L2, Ar1, and Ar2, for example, but not limited to, a dibenzothienyl group, a dibenzofuranyl group, and the like.

[0051] In the present application, the alkyl group having 1 to 10 carbon atoms can include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and the like, and specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a n-propyl group, an iso-propyl group, a n-butyl group, an iso-butyl group, a t-butyl group, a n-pentyl group, an iso-pentyl group, a neopentyl group, a n-hexyl group, and the like.

[0052] In the present application, the number of carbon atoms of a deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl.

[0053] In the present application, the number of carbon atoms of a deuterated aryl group having 6 to 20 carbon atoms is, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20. Specific examples of the deuterated aryl group include, but are not limited to, penta-deuterophenyl, tri-deuterophenyl.

[0054] In the present application, a halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0055] In the present application, specific examples of a trialkylsilyl group include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.

[0056] In the present application, a haloalkyl group refers to an alkyl group substituted with a halogen, and specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0057] In the present application, a deuterated alkyl group refers to an alkyl group substituted with one or more deuterium, and specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl.

[0058] In the present application, the number of carbon atoms of a cycloalkyl group having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl.

[0059] In the present application, the number of carbon atoms of a deuterated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl.

[0060] In the present application, the number of carbon atoms of a haloalkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. Specific examples of the haloalkyl group include, but are not limited to, trifluoromethyl.

[0061] In the present application, a ring system formed by n atoms is an n-membered ring. For example, a phenyl group is a 6-membered ring. A 3- to 15-membered ring refers to a cyclic group having 3 to 15 ring atoms. Examples of the 3- to 15-membered ring include a cyclopentane ring (5-membered ring), a cyclohexane ring (6-membered ring), a benzene ring (6-membered ring), a fluorene ring (13-membered ring), and the like.

[0062] In the present application, In the present application, a bond represented by

[0063] In the present application, a bond represented by which indicates that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is attached to the remainder of the molecule through two indefinite bonds that extend through the bicyclic ring system, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (f-1) to (f-10):

[0064] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is attached to the remainder of the molecule through one indefinite bond that extends from the middle of one of the phenyl rings, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (X'-1) to (X'-4):

[0065] An indefinite substituent in the present application refers to a substituent that is attached through a single bond that extends from the center of a ring system, and indicates that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is attached to the quinoline ring through one indefinite bond, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (Y-1) to (Y-7):

[0066] In some embodiments, ring A is selected from the following structures:

[0067] wherein the * position on the phenanthrene ring represents the position that is fused to the * position in formula 1.

[0068] In some embodiments, the arylamine compound is selected from the structures represented by the following formulae (1-1) to (1-7):

[0069] In formulae (1-1) to (1-7), L, L1, L2, Ar1, Ar2, R1, R2, n1, and n2 have the same meanings as in formula 1 above.

[0070] In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0071] ​In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms.

[0072] In some embodiments, the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group, or a deuterated phenyl group.

[0073] In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofluorenylene group, a substituted or unsubstituted carbazolylene group.

[0074] In some embodiments, the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a pentadeuterophenyl group, or a phenyl group.

[0075] In some embodiments, L1and L2are the same or different, and each is independently selected from a single bond or the group consisting of:

[0076] In some embodiments, L is selected from a single bond or the group consisting of:

[0077] In some embodiments, L1and L2are the same or different, and each is independently selected from a single bond or the group consisting of:

[0078] In some embodiments, L is selected from a single bond or the group consisting of:

[0079] In some embodiments, Ar1and Ar2are the same or different and each is independently selected from substituted or unsubstituted aryl 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, substituted or unsubstituted heteroaryl 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.

[0080] In some embodiments, the substituents in Ar1and Ar2are the same or different and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0081] In some embodiments, Ar1and Ar2are 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 phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0082] In some embodiments, the substituents in Ar1and Ar2are the same or different and each is independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a pentadeuteriophenyl group, a phenyl group, or a naphthyl group.

[0083] In some embodiments, Ar1and Ar2are the same or different and each is independently selected from the following groups:

[0084] In some embodiments, Ar1and Ar2are the same or different and each is independently selected from the following groups:

[0085] In some embodiments, are the same or different and each is independently selected from the following groups:

[0086] In some embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl. In some embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl.

[0087] In some embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl.

[0088] In some more specific embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl. In some embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl.

[0089] In some embodiments, each R1and R2is the same or different, and each is independently selected from the group consisting of deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, and phenyl.

[0090] In some embodiments, the arylamine compound is selected from the group consisting of the following compounds:

[0091] In a second aspect, the present application provides an organic electroluminescent device, comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises the arylamine compound of the first aspect of the present application.

[0092] The arylamine compound provided by the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and lifetime of the organic electroluminescent device.

[0093] Optionally, the functional layer further comprises a first hole transport layer and a light-emitting adjustment layer (also referred to as a second hole transport layer, a light-emitting adjustment layer, or a hole auxiliary layer), the first hole transport layer is located between the anode and the organic light-emitting layer, and the light-emitting adjustment layer is located between the first hole transport layer and the organic light-emitting layer.

[0094] Optionally, the functional layer further comprises a light-emitting layer, the light-emitting layer comprises a light-emitting layer host material and a doping material, and the light-emitting layer host material comprises the arylamine compound of the present application.

[0095] In some embodiments, the light-emitting layer host material is composed of the arylamine compound provided by the present application and other materials.

[0096] According to a specific embodiment, the organic electroluminescent device is shown in Fig. 1, which comprises 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 sequentially stacked.

[0097] In the present application, the anode 100 comprises an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layers. Specific examples of the anode material 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. A transparent electrode comprising indium tin oxide (ITO) is preferably used as the anode.

[0098] In the present application, the first hole transport layer or the light-emitting adjustment layer can each comprise one or more hole transport materials, which can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and can be specifically selected from the following compounds or any combination thereof:

[0099] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0100] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.

[0101] Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability of hole injection into the first hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, which are not specifically limited in the present application. The material of the hole injection layer 310 is for example selected from the following compounds or any combination thereof:

[0102] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0103] Optionally, the organic light-emitting layer 330 can be composed of a single light-emitting material, or can 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, the holes injected into the organic light-emitting layer 330 and the electrons injected into the organic light-emitting layer 330 can recombine to form excitons in the organic light-emitting layer 330, the excitons transfer energy to the host material, the host material transfers energy to the guest material, and the guest material is capable of emitting light.

[0104] The host material of the organic light-emitting layer 330 can include a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials. The host material of the organic light-emitting layer 330 can be a single compound, a combination of two or more compounds. Optionally, the host material includes the arylamine compound of the present application.

[0105] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. The guest material is also referred to as a dopant or a dopant material. According to the type of light emission, it can be divided into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,

[0106] In an embodiment of the present 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 includes RH-N and the compound of the present application. The guest material can be, for example, RD-1.

[0107] The electron transport layer 340 can be a single-layer structure or a multi-layer structure, and can include one or more electron transport materials selected from, but not limited to, LiQ, a benzimidazole derivative, an oxadiazole derivative, a quinoxaline derivative, or other electron transport materials, which are not particularly limited in the present application. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:

[0108] In an embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0109] In the present application, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layered material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode comprising magnesium and silver is included as the cathode.

[0110] Alternatively, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability of injecting electrons into the electron transport layer 340. The electron injection layer 350 can comprise an inorganic material such as an alkali metal sulfide, an alkali metal halide, or the like, or can comprise a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 comprises ytterbium (Yb).

[0111] The third aspect of the present application provides an electronic device comprising the organic electroluminescent device according to the second aspect of the present application.

[0112] According to one embodiment, as shown in FIG. 2, an electronic device 400 is provided, which comprises the organic electroluminescent device described above. The 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, but not limited to, a computer screen, a cell phone screen, a television, electronic paper, an emergency lighting lamp, an optical module, and the like.

[0113] The synthesis of the arylamine compounds of the present application will now be described in detail with reference to the following synthesis examples, but the present application is not limited thereto.

[0114] Synthesis Examples

[0115] Those skilled in the art will recognize that the chemical reactions described in the present application can be used to practice the present application in a variety of synthetic routes and that the application is not limited to the reaction conditions described. For example, suitable protecting groups can be used to avoid unwanted reactions and other reagents can be used instead of the reagents described in the present application. The protecting groups can be removed using standard methods. The compounds of the present application can be prepared in a variety of synthetic routes using readily available starting materials and the reagents described in the present application, or modifications thereof. The starting materials and the reagents used in the present application are commercially available or are readily prepared by those skilled in the art.

[0116] Synthesis of intermediates:

[0117] Synthesis of Sub-a1:

[0118] Into a 500 mL three-necked flask, RM-1 (12.63 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The system was warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then washed with 100 mL of anhydrous ethanol. The product was obtained as a gray solid. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene. The catalyst was removed by passing the solution through a silica gel column. The product was obtained as a white solid after concentration (12.56 g, 73% yield).

[0119] Sub-a2 was synthesized according to the procedure for the synthesis of Sub-a1, using the reactant A shown in Table 1 instead of RM-1.

[0120] Table 1: Synthesis of Sub-a2

[0121] Synthesis of Sub-b1:

[0122] Into a 500 mL three-necked flask, Sub-a1 (18.93 g, 55 mmol), RM-2 (10.97 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (180 mL), anhydrous ethanol (45 mL), and deionized water (45 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to reflux for 8 h. After the system was cooled to room temperature, the mixture was extracted with dichloromethane (100 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase. The product was obtained as a white solid (11.42 g, 64% yield).

[0123] Sub-b2 to Sub-b6 were synthesized according to the procedure for the synthesis of Sub-b1, using the reactant B shown in Table 2 instead of Sub-a1, and the reactant C instead of RM-2.

[0124] Table 2: Synthesis of Sub-b2 to Sub-b6

[0125] Synthesis of Sub-c1:

[0126] Into a 1000 mL three-necked flask, Sub-a1 (46.38 g, 130 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (230 mL) were added under nitrogen atmosphere. The system was cooled to -15 °C and kept for 30 min. Then (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol) was added into the flask and the system was kept at -15 °C for 1 h. After that, the reaction system was allowed to warm up to room temperature and extracted with dichloromethane (200 mL x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to give Sub-c1 (39.52 g, yield 79%) as a gray-white solid.

[0127] Referring to the synthesis method of Sub-c1, Sub-c2 to Sub-c6 were synthesized by using the reactants D shown in Table 3 to replace Sub-b1.

[0128] Table 3: Synthesis of Sub-c2 to Sub-c6

[0129] Synthesis of Sub-d1:

[0130] Into a 1000 mL three-necked flask, Sub-c1 (45.80 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (500 mL) were added under nitrogen atmosphere. The system was warmed up to reflux and stirred for 4 h. After the reaction system was cooled to room temperature, the reaction solution was poured into 1000 mL deionized water and neutralized with saturated sodium hydroxide solution. Then the reaction solution was extracted with dichloromethane (250 mL x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate and filtered. The solvent was removed by distillation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give Sub-d1 (26.87 g, yield 64%) as a white solid.

[0131] Referring to the synthesis method of Sub-d1, Sub-d2 to Sub-d6 were synthesized by using the reactants E shown in Table 4 to replace Sub-c1.

[0132] Table 4: Synthesis of Sub-d2 to Sub-d6

[0133] Synthesis of Sub-e1:

[0134] Into a 500 mL three-necked flask, Sub-dl (17.64 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (180 mL) were added successively under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.48 g, 1.0 mmol) were added rapidly. The system was warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added, and the mixture was stirred thoroughly for 30 min. The mixture was filtered under reduced pressure, and the filter cake was washed with deionized water until neutral, and then washed with 100 mL of anhydrous ethanol. A gray solid was obtained. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene. The catalyst was removed by silica gel column, and the solvent was removed by concentration. A white solid, Sub-el (16.66 g, 75% yield), was obtained.

[0135] Referring to the synthesis method of Sub-el, Sub-e2 to Sub-e6 were synthesized by using the reactant F shown in Table 5 instead of Sub-dl.

[0136] Table 5: Synthesis of Sub-e2 to Sub-e6

[0137] Synthesis of Sub-fl:

[0138] Into a 1000 mL three-necked flask, Sub-el (24.44 g, 55 mmol), 4-bromochlorobenzene (9.57 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5.0 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (240 mL), anhydrous ethanol (60 mL) and deionized water (60 mL) were added successively under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to reflux for 8 h. After the system was cooled to room temperature, the mixture was extracted with dichloromethane (100 mL x 3 times), and the organic phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed by filtration under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase. A white solid, Sub-fl (16.73 g, 78% yield), was obtained.

[0139] Referring to the synthesis method of Sub-f1, using the reactant G shown in Table 6 to replace Sub-e1, and using the reactant H to replace 4-bromochlorobenzene, Sub-f2 to Sub-f9 were synthesized.

[0140] Table 6: Synthesis of Sub-f2 to Sub-f9

[0141] Synthesis Example 1: Synthesis of compound 4

[0142] Into a 250 mL three-necked flask, RM-3 (8.06 g, 25 mmol), Sub-d1 (9.70 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl) (0.95 g, 1.0 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were added successively under nitrogen atmosphere, and the reaction was heated to reflux and stirred overnight. After the system was cooled to room temperature, dichloromethane (100 mL x 3 times) was used for extraction, the organic phases were combined and dried with anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure after filtration to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as the mobile phase to obtain a white solid (12.55 g; yield 77%, m / z = 652.22 [M+H]). + ).

[0143] Referring to the synthesis method of compound 4, using the reactant J shown in Table 7 to replace Sub-d1, and using the reactant K to replace RM-3, the compounds in Table 7 were synthesized.

[0144] Table 7: Synthesis of compounds of the application

[0145] NMR data of some compounds:

[0146] NMR data of compound 45: 1 H-NMR (400 MHz, CD2Cl2) δ ppm: 8.62 (d, 1H), 8.19-8.12 (m, 3H), 8.00-7.68 (m, 13H), 7.62 (t, 1H), 7.53-7.31 (m, 8H), 7.16 (s, 1H), 6.96 (d, 1H), 6.92 (d, 1H), 6.73 (d, 2H).

[0147] Preparation and evaluation of organic electroluminescent devices:

[0148] The present embodiment 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 above-mentioned organic compound of the present embodiment. Hereinafter, the organic electroluminescent device of the present embodiment will be described in detail by way of examples. However, the following examples are merely illustrative of the present embodiment, and are not intended to limit the present embodiment.

[0149] Example 1: Red organic electroluminescent device

[0150] First, the anode is pre-processed by the following procedure: on an ITO / Ag / ITO substrate with thicknesses of 1500 / 200 / 1500 A, respectively, surface treatment is performed using UV ozone and O2:N2 plasma to increase the work function of the anode, or organic solvent cleaning of the ITO substrate surface to remove impurities and oil on the ITO substrate surface. On the experimental substrate (anode), PD:HT-1 is co-evaporated at a rate ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 A, and then HT-1 is vacuum evaporated on the hole injection layer to form a first hole transport layer with a thickness of 100 A.

[0151] On the first hole transport layer, compound HT-2 is vacuum evaporated to form a light-emitting auxiliary layer with a thickness of 100 A. Next, on the light-emitting auxiliary layer, compound 4:RH-N:RD is co-evaporated at a ratio of 49%:49%:2% to form a red light-emitting layer (EML) with a thickness of 200 A.

[0152] On the light-emitting layer, compound ET-1 and LiQ are co-evaporated at a rate ratio of 1:1 to form an electron transport layer (ETL) with a thickness of 100 A, Yb is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of 10 A, and then magnesium (Mg) and silver (Ag) are mixed at a rate of 1:9 and vacuum evaporated on the electron injection layer to form a cathode with a thickness of 200 A.

[0153] On the light-emitting layer, compound ET-1 and LiQ are co-evaporated at a rate ratio of 1:1 to form an electron transport layer (ETL) with a thickness of 100 A, Yb is evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of 10 A, and then magnesium (Mg) and silver (Ag) are mixed at a rate of 1:9 and vacuum evaporated on the electron injection layer to form a cathode with a thickness of 200 A.

[0154] In addition, CP is vacuum evaporated on the above-mentioned cathode as a cover layer with a thickness of 100 A, thereby completing the manufacture of the red organic electroluminescent device. Examples 2-60

[0155]

[0156] ​​​​​​​An organic electroluminescent device was produced using the same method as in Example 1, except that Compound X in Table 8 below was used instead of Compound 4 in Example 1 when forming the light-emitting layer.

[0157] Comparative Examples 1 to 4

[0158] An organic electroluminescent device was produced using the same method as in Example 1, except that Compound A, Compound B, Compound C and Compound D were used instead of Compound 4 in Example 1 when forming the light-emitting layer, respectively.

[0159] In the production of the organic electroluminescent device, the structures of each material used in the comparative examples and the examples are as follows:

[0160] The organic electroluminescent devices produced in Examples 1 to 60 and Comparative Examples 1 to 4 were tested for performance, and the IVL performance of the devices was tested at 10 mA / cm 2 , the T95 device lifetime was tested at 20 mA / cm 2 , and the test results are shown in Table 8 below.

[0161] Table 8

[0162] As can be seen from Table 8 above, when the arylamine compound of the present application is used as the host material of the light-emitting layer of a red organic electroluminescent device, the device of Examples 1 to 60 has at least a 16.2% increase in luminous efficiency (Cd / A) and at least a 12.7% increase in T95 lifetime, compared to the devices of Comparative Examples 1 to 4.

[0163] The reason for this is that, first, the phenanthronaphthofuran parent nucleus has a suitable first excited triplet state energy level, making it suitable as a fragment of a red light host material; second, the phenanthronaphthofuran parent nucleus structure has a large conjugated system, which, after being connected to an arylamine hole transport fragment, can enhance the intermolecular forces and improve the hole mobility of the compound. When the compound of the present application is used as a hole transport material in a mixed red light host material, it can improve the carrier balance in the light-emitting layer, widen the carrier recombination region, improve the excitation generation and utilization efficiency, and improve the luminous efficiency and lifetime of the device.

[0164] The preferred embodiments of the present application are described in detail above with reference to the accompanying drawings, but the present application is not limited to the specific details of the above-described embodiments, and various simple modifications can be made to the technical solutions of the present application within the scope of the technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. An arylamine compound characterized in that, The arylamine compound has a structure represented by Formula 1: wherein ring A is a phenanthrene ring; L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms; Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; the substituents in L, L1, L2, Ar1and Ar2are the same or different, and each is independently selected from deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring; each R1and R2is the same or different, and each is independently selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, or a phenyl group; n1 represents the number of R1, and n1 is selected from 0, 1, 2, 3, 4, 5 or 6; n2 represents the number of R2, and n1 is selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8.

2. The arylamine compound according to claim 1, wherein, L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 18 carbon atoms; the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group; optionally, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms; the substituents in Ar1and Ar2are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 5 to 12 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, or a deuterated aryl group having 6 to 15 carbon atoms, optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

3. The arylamine compound according to claim 1 or 2, wherein, L, L1and L2are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazolyl group; Optionally, the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl or phenyl.

4. The arylamine compound according to any one of claims 1 to 3, wherein, L1and L2are the same or different and each independently selected from the group consisting of a single bond or: Optionally, L is selected from the group consisting of a single bond or the following groups:

5. The arylamine compound according to any one of claims 1 to 4, wherein, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazolyl group; Optionally, the substituents in Ar1and Ar2are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, phenyl or naphthyl.

6. The arylamine compound according to any one of claims 1 to 5, wherein, Ar1and Ar2are the same or different and each independently selected from the following groups:

7. The arylamine compound according to any one of claims 1 to 6, wherein, the same or different, and each independently selected from the group consisting of:

8. The arylamine compound according to any one of claims 1 to 7, wherein, in formula 1, is selected from the group consisting of:

9. The arylamine compound according to any one of claims 1 to 8, wherein, Each R1and R2is the same or different, and each is independently selected from deuterium, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl or phenyl.

10. The aromatic amine compound according to any one of claims 1 to 9, having the structure shown in formulas (1-1) to (1-7): In formulae (1-1) to (1-7), L, L1, L2, Ar1, Ar2, R1, R2, n1and n2have the same meanings as in claim 1.

11. The arylamine compound according to any one of claims 1 to 10, wherein, selected from the group consisting of: selected from the group consisting of:

12. The arylamine compound according to any one of claims 1 to 11, wherein, The arylamine compound is selected from the group consisting of:

13. An organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises the arylamine compound according to any one of claims 1 to 12; Optionally, the functional layer comprises a light-emitting layer, and the light-emitting layer comprises the arylamine compound.

14. An electronic device, characterized by The organic electroluminescent device according to claim 13. The organic electroluminescent device according to claim 13.

Images