Arylamine compound, organic electroluminescent device and electronic device

Abstract

The invention relates to the technical field of organic electroluminescent materials, and provides an arylamine compound, an organic electroluminescent device containing the arylamine compound and an electronic device. A parent nucleus of the arylamine compound contains a di (benzofuran) naphthalene structure, and when the compound is used as a hole transport type main body material in a mixed type main body material, the carrier balance in a luminescent layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, and the luminous efficiency and the service life of a device can be improved.

Description

TECHNICAL FIELD

[0001] 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

[0002] With the development of electronic technology and the progress of material science, the application range of electronic components 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, the electrons on the cathode side move to the electroluminescent layer, and the holes on the anode side also move to the light-emitting layer. The electrons and holes combine in the electroluminescent layer to form excitons, which are in an excited state and release energy outward, thereby making the electroluminescent layer emit light.

[0003] 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, that is, the anode, the cathode and the multi-layer organic functional layer together constitute 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

[0004] In view of the above problems existing in the prior art, the purpose of the present application is to provide an arylamine compound and an organic electroluminescent device and an electronic device comprising the same, which is used in an organic electroluminescent device and can improve the performance of the device.

[0005] According to a first aspect of the present application, an arylamine compound is provided, which has a structure represented by formula 1:

[0006]

[0007] wherein R1-R 12one group selected from the structure represented by Formula A, and the remaining groups are each independently selected from hydrogen, 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0008] 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 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0009] 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;

[0010] the substituents in L, L1, L2, Ar1, and 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 heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar1and Ar2, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0011] According to a second aspect of the present application, there is provided 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; the functional layer comprises the arylamine compound described above.

[0012] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.

[0013] The compound of the present application contains a di(benzofuran) naphthalene mother nucleus structure in the structure of the compound, the mother nucleus is connected with a hole transport segment of arylamine, and the compound is used as a hole transport type light-emitting host material. On the one hand, the special fusion mode of the mother nucleus ensures that the mother nucleus has a relatively suitable first excited triplet state energy level, which is suitable as a segment of a light-emitting host material; on the other hand, the mother nucleus structure has a relatively large conjugated system, which can enhance the intermolecular force after being connected with the arylamine hole transport group, improve the hole mobility of the compound, and reduce the carrier transport barrier; the arylamine hole transport group is connected at any position of the mother nucleus, which can endow the compound with good film-forming performance, so that the thin film of the compound has good thermodynamic stability. When the compound of the present application is used as a hole transport type host material in a mixed light-emitting host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination region 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

[0014] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, and are used to explain the present application together with the specific embodiments described below, but do not constitute a limitation on the present application.

[0015] Figure 1 is a structural schematic diagram of an organic electroluminescent device of an embodiment of the present application.

[0016] Figure 2 is a structural schematic diagram of an electronic device of an embodiment of the present application.

[0017] REFERENCE NUMERALS

[0018] 100, anode 200, cathode 300, functional layer 310, hole injection layer

[0019] 321, first hole transport layer 322, light-emitting adjustment layer 330, organic light-emitting layer 340, electron transport layer

[0020] 350, electron injection layer 320, hole transport zone 400, electronic device DETAILED DESCRIPTION

[0021] 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.

[0022] In a first aspect, the present application provides an arylamine compound having a structure represented by Formula 1:

[0023]

[0024] wherein R1 to R 12 one and only one of R1 to R4 is a structure represented by Formula A, and the rest of R1 to R4 are each independently selected from hydrogen, 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, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms;

[0025] 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 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;

[0026] Ar1 and Ar2 are 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;

[0027] the substituents in L, L1, L2, Ar1, and Ar2 are 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 heteroaryl group having 3 to 20 carbon atoms, or a cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar1 and Ar2, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0028] 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 a scenario in which any two adjacent substituents form a ring, and a scenario in which any two adjacent substituents each independently exist 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 having two substituents 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 having one substituent on each of two adjacent atoms, the two substituents can be fused into a ring.

[0029] In the present application, the terms "optionally", "preferably" and "in some embodiments" have the same meaning.

[0030] In the present application, the description "each independently" can be interchangeable with "respectively independently" and "each independently", and should be interpreted in a broad sense, which means that the specific options expressed by the same symbols in different groups do not affect each other, or 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, which means 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.

[0031] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can have or not have a substituent (hereinafter, the substituent will be collectively referred to as Rcfor the sake of description). For example, "substituted or unsubstituted aryl" means aryl with a substituent Rc, or aryl without a substituent. The above-mentioned substituent Rc, for example, can be deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc. The number of substituents can be one or more.

[0032] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.

[0033] 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.

[0034] In the present application, the hydrogen atoms in the structure of the compound include various isotopes of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0035] In the present application, "D" in the structural formula of the compound means deuterium.

[0036] In the present application, saturated or unsaturated 3-15 membered ring refers to a ring containing 3-15 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.

[0037] In this application, aryl refers to any optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aryl group can be a monocyclic aryl, a fused-ring aryl, two or more monocyclic aryl groups linked by carbon-carbon bonds, a monocyclic aryl and a fused-ring aryl linked by carbon-carbon bonds, or two or more fused-ring aryl groups linked by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups linked by carbon-carbon bonds can also be considered as the aryl group 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.

[0038] 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.

[0039] In this application, terphenyl includes

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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 quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl 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.

[0044] 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 quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl 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.

[0045] 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.

[0046] 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 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.

[0047] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, iodine.

[0048] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, and the like.

[0049] In the present application, haloalkyl means alkyl substituted with halogen, and specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0050] In the present application, deuterated alkyl means alkyl substituted with one or more deuterium, and specific examples of deuterated alkyl include, but are not limited to, trideuteromethyl.

[0051] In the present application, the number of carbon atoms of cycloalkyl having 3 to 10 carbon atoms is, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of cycloalkyl include, but are not limited to, cyclopentyl, cyclohexyl, and adamantyl.

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

[0053] In the present application, the number of carbon atoms of haloalkyl having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of haloalkyl include, but are not limited to, trifluoromethyl.

[0054] In the present application, means a chemical bond to which other groups are attached.

[0055] In the present application, an indefinite position connection bond refers to a single bond extending from a ring system which means that one end of the connection bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is attached to other positions in the molecule through two indefinite position connection bonds extending through the bicyclic ring, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (f-1) to (f-10):

[0056]

[0057] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is attached to other positions in the molecule through one indefinite position connection bond extending from the middle of one of the benzene rings, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (X'-1) to (X'-4):

[0058]

[0059] In the present application, an optionally substituted substituent refers to a substituent connected by a single bond extending from the center of a ring system, which indicates that the substituent can be connected at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is connected to the quinoline ring by an optionally substituted connecting bond, which indicates that the meaning includes any possible connection as shown in formula (Y-1) to formula (Y-7):

[0060]

[0061] The arylamine compound of the present application is selected from the structures represented by formula (1-1) to formula (1-12):

[0062]

[0063]

[0064] 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 a carbon number of 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, or a substituted or unsubstituted heteroarylene group having a carbon number of 12, 13, 14, 15, 16, 17, or 18.

[0065] 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 a carbon number of 6 to 15, or a substituted or unsubstituted heteroarylene group having a carbon number of 12 to 18.

[0066] Optionally, 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 a carbon number of 1 to 4, a haloalkyl group having a carbon number of 1 to 4, a deuterated alkyl group having a carbon number of 1 to 4, a trialkylsilyl group having a carbon number of 3 to 7, a phenyl group, or a deuterated phenyl group.

[0067] In some embodiments, L, L1, and L2 are each 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 dibenzofurane group, a substituted or unsubstituted carbazolylene group.

[0068] Optionally, 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 trideuterated methyl group, a trimethylsilyl group, a pentadeuterated phenyl group, or a phenyl group.

[0069] In some embodiments, L1and L2are each independently selected from a single bond or the group consisting of:

[0070]

[0071]

[0072] In some embodiments, L is selected from the group consisting of a single bond or the following groups:

[0073]

[0074] In some embodiments, L1and L2are the same or different, and each is independently selected from the group consisting of a single bond or the following groups:

[0075]

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

[0077]

[0078] In some embodiments, Ar1and Ar2are each 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.

[0079] In some embodiments, Ar1and Ar2are each independently selected from substituted or unsubstituted aryl having 6 to 25 carbon atoms or substituted or unsubstituted heteroaryl having 12 to 18 carbon atoms.

[0080] Optionally, each of the substituents in Ar1and Ar2is 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, and optionally, any two adjacent substituents in Ar1and Ar2form a benzene ring or a fluorene ring.

[0081] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from the group consisting of 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, and substituted or unsubstituted carbazolyl.

[0082] Optionally, the substituents in Ar1and Ar2are the same or different, and each is independently selected from the group consisting of deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, phenyl, or naphthyl; optionally, in Ar1and Ar2, any two adjacent substituents form a benzene ring or a fluorene ring.

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

[0084]

[0085] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from the group consisting of:

[0086]

[0087]

[0088] In some embodiments, are the same or different, and each is independently selected from the group consisting of:

[0089]

[0090] In some embodiments, in Formula 1, is selected from the group consisting of:

[0091]

[0092]

[0093]

[0094] In some embodiments, R1to R 12 one is selected from the structure shown in Formula A, and the rest are each independently selected from the group consisting of hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, or naphthyl.

[0095] In some embodiments, the arylamine compound of the present application is selected from the group consisting of the following compounds:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] 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.

[0106] The arylamine compound provided by the present application can be used to form at least one organic film layer in the functional layer, so as to improve the luminous efficiency and lifetime of the organic electroluminescent device.

[0107] Optionally, the functional layer further comprises a hole transport region, wherein the hole transport region comprises a hole transport layer (also referred to as a first hole transport layer) and a light-emitting adjustment layer (also referred to as a second hole transport layer or a hole auxiliary layer or a light-emitting auxiliary layer), the 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.

[0108] Optionally, the functional layer further comprises a light-emitting layer, wherein 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.

[0109] In some embodiments, the light-emitting layer host material is composed of the arylamine compound provided by the present application and other materials.

[0110] According to a specific embodiment, the organic electroluminescent device comprises, as shown in Figure 1 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.

[0111] 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 layer. 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. Preferably, the transparent electrode comprises an anode comprising indium tin oxide (ITO).

[0112] In the present application, the first hole transport layer and the light-emitting adjustment layer each can 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 selected from the following compounds or any combination thereof:

[0113]

[0114]

[0115] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0116] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.

[0117] 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 injecting holes 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 particularly limited in the present application. The material of the hole injection layer 310 is selected from the following compounds or any combination thereof, for example:

[0118]

[0119]

[0120] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0121] 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.

[0122] 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.

[0123] 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 classified into a fluorescent dopant and a phosphorescent dopant. Specific examples of the phosphorescent dopant include, but are not limited to,

[0124]

[0125] 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.

[0126] 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 material of the electron transport layer 340 includes, but is not limited to, the following compounds:

[0127]

[0128] In an embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.

[0129] 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.

[0130] 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).

[0131] A third aspect of this application provides an electronic device including the organic electroluminescent device described in the second aspect of this application.

[0132] 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.

[0133] The following examples illustrate the synthesis method of the aromatic amine compounds of this application, but this application is not limited thereto.

[0134] Synthesis Examples

[0135] 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.

[0136] Synthesis of RM-1:

[0137]

[0138] Into a 500 mL three-necked flask, RM-1 (20.00 g, 57.80 mmol), 2-fluorobenzenboronic acid (8.09 g, 57.80 mmol), Pd(PPh3)4(0.67 g, 0.58 mmol), anhydrous sodium carbonate (12.25 g, 115.60 mmol), toluene (160 mL), tetrahydrofuran (20 mL) and deionized water (20 mL) were added successively under nitrogen atmosphere. The flask was stirred and heated to reflux for 16 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. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid Sub-a1 (15.86 g, yield 76%).

[0139] Synthesis of Sub-a1:

[0140]

[0141] Into a 500 mL three-necked flask, RM-1 (20.00 g, 57.80 mmol), 2-fluorobenzenboronic acid (8.09 g, 57.80 mmol), Pd(PPh3)4(0.67 g, 0.58 mmol), anhydrous sodium carbonate (12.25 g, 115.60 mmol), toluene (160 mL), tetrahydrofuran (20 mL) and deionized water (20 mL) were added successively under nitrogen atmosphere. The flask was stirred and heated to reflux for 16 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. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain white solid Sub-a1 (15.86 g, yield 76%).

[0142] Referring to the synthesis method of Sub-a1, Sub-a2 to Sub-a5 were synthesized by using the reactants A shown in Table 1 to replace RM-1 and the reactants B to replace 2-fluorobenzenboronic acid.

[0143] Table 1: Synthesis of Sub-a2 and Sub-a5

[0144]

[0145] Synthesis of Sub-b1:

[0146]

[0147] Into a 500 mL three-necked flask, Sub-a1 (15.00 g, 41.52 mmol), RM-2 (7.24 g, 41.52 mmol), Pd(PPh3)4 (0.48 g, 0.42 mmol), anhydrous sodium carbonate (8.8 g, 83.05 mmol), toluene (120 mL), tetrahydrofuran (30 mL) and deionized water (30 mL) were added successively under nitrogen atmosphere. The reaction was stirred and heated to reflux for 16 h. After the system was cooled to room temperature, the reaction mixture was extracted with dichloromethane (100 mL x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and 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 as the mobile phase to give Sub-b1 (12.79 g, yield 75%) as a white solid.

[0148] Referring to the synthesis method of Sub-b1, Sub-b2 to Sub-b6 were synthesized by using the reactants C and D shown in Table 2 to replace Sub-a1 and RM-2, respectively.

[0149] Table 2: Synthesis of Sub-b2 to Sub-b6

[0150]

[0151] Synthesis of Sub-c1:

[0152]

[0153] Into a 1000 mL three-necked flask, Sub-b1 (15.0 g, 36.5 mmol) and dry dichloromethane (150 mL) were added under nitrogen atmosphere. The system was cooled to 0 °C ± 5 °C, and a solution of boron tribromide in dichloromethane (73 mL, 1 M) was added dropwise using a constant pressure dropping funnel. The temperature was strictly controlled at 0 °C ± 5 °C during the dropwise addition. After the dropwise addition was completed, the system was incubated at 0 °C ± 5 °C for 2 h, and then allowed to naturally warm to room temperature and stirred overnight. The system was cooled to -78 °C again, and methanol (11 mL) was slowly added dropwise using a constant pressure dropping funnel to quench the reaction. After the system was warmed to room temperature, the reaction solution was extracted with dichloromethane (100 mL x 3 times). The organic phase was dried over anhydrous magnesium sulfate, and 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 (8.1 g, yield 58%) as a white solid.

[0154] Referring to the synthesis method of Sub-c1, Sub-c2 to Sub-c6 were synthesized by using the reactants E shown in Table 3 to replace Sub-b1.

[0155] Table 3: Synthesis of Sub-c2 to Sub-c6

[0156]

[0157] Synthesis of Sub-d1:

[0158]

[0159] Into a 500 mL three-necked flask, Sub-c1 (15.00 g, 39.18 mmol), cesium carbonate (25.53 g, 78.37 mmol) and DMSO (150 mL) were added under nitrogen atmosphere. The stirring was started and the system was heated to 80 °C for 4 h. After the system was cooled to room temperature, the product was extracted with dichloromethane (100 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as mobile phase to give Sub-d1 (10.07 g, yield 75%) as a white solid.

[0160] Referring to the synthesis of Sub-d1, Sub-d2 to Sub-d6 were synthesized by using the reactants F shown in Table 4 instead of Sub-c1.

[0161] Table 4: Synthesis of Sub-d2 to Sub-d6

[0162]

[0163]

[0164] Synthesis of Sub-e1:

[0165]

[0166] Into a 1000 mL three-necked flask, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol) and anhydrous tetrahydrofuran (225 mL) were added under nitrogen atmosphere. The system was cooled to -15 °C for 30 min, then Sub-a3 (45.10 g, 130 mmol) was weighed and dissolved in anhydrous tetrahydrofuran (225 mL), the solution was slowly added to the reaction system using a constant pressure dropping funnel, the temperature was kept at -15 °C during the addition, and after the addition was completed, the system was kept stirring at -15 °C for 1 h. Then the system was allowed to warm to room temperature, extracted with dichloromethane (200 mL x 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography using n-heptane / dichloromethane as mobile phase to give Sub-e1 (40.4 g, yield 83%) as a red solid.

[0167] Referring to the synthesis method of Sub-e1, Sub-e2 and Sub-e3 were synthesized by using reactant G shown in Table 5 instead of Sub-a3.

[0168] Table 5: Synthesis of Sub-e2 and Sub-e3

[0169]

[0170] Synthesis of Sub-f1:

[0171]

[0172] Into a 1000 mL three-necked flask, Sub-e1 (44.60 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (500 mL) were sequentially added under nitrogen atmosphere, and the reaction was stirred at reflux for 4 h. After the reaction system was 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 x 3 times). The combined organic phase was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-f1 (22.80 g, yield 56%).

[0173] Referring to the synthesis method of Sub-f1, Sub-f2 and Sub-f3 were synthesized by using reactant H shown in Table 6 instead of Sub-e1.

[0174] Table 6: Synthesis of Sub-f2 and Sub-f3

[0175]

[0176] Synthesis of Sub-f5:

[0177]

[0178] Into a 100 mL three-necked flask, Sub-f1 (8.60 g, 25 mmol) and 200 mL of benzene-d6 were added under nitrogen atmosphere, and the reaction was stirred at 60°C. After trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added, the reaction was stirred at boiling for 24 h. After the reaction system was cooled to room temperature, 50 mL of heavy water was added, and the reaction solution was neutralized by stirring for 10 min with saturated K3PO4 aqueous solution. The organic layer was extracted with dichloromethane (50 mL x 3 times), and the combined organic phase was dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure 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 white solid Sub-f5 (4.80 g, yield 54%).

[0179] Synthesis of compound 1:

[0180]

[0181] Into a 500 mL three-necked flask, Sub-f1 (15.00 g, 43.76 mmol), SM2 (14.06 g, 43.75 mmol), tris(dibenzylideneacetone)dipalladium (0.4 g, 0.44 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-biphenyl (0.36 g, 0.87 mmol), sodium tert-butoxide (6.31 g, 65.64 mmol), toluene (150 mL) were added successively under nitrogen atmosphere. The stirring was started and the reaction mixture was heated to reflux for 16 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. After filtration, 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 as the mobile phase to give compound 1 (20.60 g, yield 75%) as a white solid.

[0182] Referring to the synthesis method of compound 1, using the reactants I and J shown in Table 7 to replace Sub-f1 and SM2, respectively, compound Y was synthesized.

[0183] Table 7: Synthesis of some compounds in this application

[0184]

[0185]

[0186]

[0187]

[0188] Synthesis of compound 29:

[0189]

[0190] Into a 500 mL three-necked flask, Sub-f1 (15.00 g, 43.75 mmol), SN-1 (22.64 g, 43.75 mmol), Pd(PPh3)4 (0.51 g, 0.44 mmol), anhydrous potassium carbonate (12.09 g, 87.51 mmol), tetrabutylammonium bromide (0.14 g, 0.44 mmol), toluene (120 mL), ethanol (60 mL) and deionized water (30 mL) were added successively under nitrogen atmosphere. The stirring was started and the reaction was heated to reflux for 16 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. After filtration, 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 as the mobile phase to give compound 29 (23.89 g, yield 70%) as a white solid.

[0191] Referring to the synthesis method of compound 29, using the reactant K shown in the table to replace Sub-f1, and using the reactant L shown in the table to replace SN-1, compound Z was synthesized.

[0192] Table 8: Synthesis of some compounds in the application

[0193]

[0194]

[0195] The mass spectrometry data of the compounds in the application are shown in Table 9.

[0196] Table 9: Mass spectrometry data of the compounds in the application

[0197] Compound Mass (m / z) [M+H]+ Compound Mass (m / z) [M+H] + ]] Compound 1 628.3 Compound 4 628.3 Compound 9 642.3 Compound 14 668.3 Compound 17 678.3 Compound 21 704.3 Compound 37 628.3 Compound 46 668.3 Compound 65 708.3 Compound 66 757.3 Compound 69 628.3 Compound 75 602.3 Compound 82 668.3 Compound 92 718.3 Compound 135 682.3 Compound 137 628.3 Compound 147 642.3 Compound 150 668.3 Compound 153 678.3 Compound 209 552.2 Compound 216 658.2 Compound 29 780.3 Compound 34 718.3 Compound 104 744.3 Compound 273 639.3 Compound 276 704.3 Compound 277 744.3 Compound 278 726.4 Compound 279 718.2 Compound 280 744.3 Compound 281 652.2 Compound 282 656.2 Compound 283 717.3 Compound 28 744.3

[0198] The nuclear magnetic resonance data of some compounds are as follows:

[0199] The nuclear magnetic resonance data of compound 1 are as follows: 1 H-NMR (400 MHz, CD2Cl2) δ (ppm): 8.75 (d, 1H), 8.21 (d, 1H), 7.63-7.39 (m, 21H), 7.26-7.22 (m, 1H), 6.96 (s, 1H), 6.67 (d, 4H);

[0200] The nuclear magnetic resonance data of compound 82 are as follows: 1H-NMR (400MHz, CD2Cl2) δ (ppm): 8.94 (d, 1H), 8.56 (d, 1H), 8.40 (d, 1H), 8.19 (s, 1H), 7.99 (d, 1H), 7.82 (d, 1H), 7.58-7.40(m,14H),7.35-7.32(m,1H),7.13-7.06(m,2H),6.69(d,1H),6.56(s,1H),6.53(d,2H),1.61(s,6H).

[0201] Fabrication and evaluation of organic electroluminescent devices:

[0202] 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.

[0203] Example 1: Red Organic Electroluminescent Device

[0204] 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.

[0205] 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]. The first hole transport layer. Compound HT-2 is vacuum-deposited onto the first hole transport layer to form a layer with a thickness of [missing information]. The light-emitting adjustment layer.

[0206] Next, on the light-emitting adjustment layer, compound 1: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).

[0207] On the light-emitting layer, compound ET-1 and LiQ are co-deposited at a 1:1 evaporation rate ratio 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 injection layer (EIL), and then magnesium (Mg) and silver (Ag) are mixed at a deposition rate of 1:9, vacuum-deposited on the electron injection layer to form a cathode with a thickness of 2000 A.

[0208] In addition, a CP with a thickness of 2000 A is vacuum-deposited on the cathode, thereby completing the manufacture of the red organic electroluminescent device.

[0209] Examples 2-34

[0210] Except that the compound X in Table 10 below is used instead of the compound 1 in Example 1 when preparing the light-emitting layer, the organic electroluminescent device is prepared by the same method as in Example 1.

[0211] Comparative Examples 1-4

[0212] Except that the compound A, the compound B, the compound C and the compound D are used instead of the compound 3 in Example 1 when preparing the light-emitting layer, respectively, the organic electroluminescent device is prepared by the same method as in Example 1.

[0213] In the preparation of each of the examples and comparative examples, the compounds used have the following structures:

[0214]

[0215] The organic electroluminescent devices prepared in Examples 1-34 and Comparative Examples 1-4 are tested for performance, and the IVL performance of the devices is tested under the condition of 10 mA / cm 2 , the T95 device lifetime is tested under the condition of 20 mA / cm 2 , and the test results are shown in Table 10 below.

[0216] Table 10: Example test results

[0217]

[0218]

[0219] As can be seen from Table 10 above, when the compound of the present application is used as the host material of the red organic electroluminescent device, the driving voltage is reduced by at least 0.2 V, the current efficiency is increased by at least 14.66%, and the T95 lifetime is increased by at least 12.47% compared with Comparative Examples 1-4.

[0220] ​​The reason is that the compound of the application contains a di(benzofuran) naphthalene parent nucleus structure, which is connected with an aromatic amine hole transport segment to serve as a hole transport type red light host material. On the one hand, the di(benzofuran) naphthalene parent nucleus has a special condensation mode, which ensures that the parent nucleus has a relatively appropriate first excited triplet state energy level, suitable as a segment of a red light host material; on the other hand, the di(benzofuran) naphthalene parent nucleus structure has a relatively large conjugated system, and each of the two oxygen atoms has two pairs of lone pair electrons, which can enhance the intermolecular force and improve the hole mobility of the compound after being connected with the aromatic amine hole transport segment. When the compound of the application is used as a hole transport type host material in a mixed type red light host material, the carrier balance in the light-emitting layer can be improved, the carrier recombination region can be widened, the excitation generation and utilization efficiency can be improved, and the device light-emitting efficiency and service life can be improved.

Claims

1. An arylamine compound characterized in that, The arylamine compound has a structure represented by Formula 1: wherein R1to R4are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl 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, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms. 12 one and only one of the groups selected from the group consisting of a structure represented by Formula A, and the remaining groups are each independently selected from the group consisting of hydrogen, deuterium, a cyano group, a halogen group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl 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, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms. 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 30 carbon atoms, or 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 of L, L1, L2, Ar1, and 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 heteroaryl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; optionally, in Ar1and Ar2, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

2. The arylamine compound according to claim 1, wherein, 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, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms; Optionally, the substituents in L, L1, and L2 are 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.

3. The arylamine compound according to claim 1, wherein, L, L1, and L2 are each 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 dibenzofurane group, and a substituted or unsubstituted carbazolylene group; Optionally, 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 trideuterated methyl group, a trimethylsilyl group, a penta-deuterated phenyl group, or a phenyl group.

4. The arylamine compound according to claim 1, wherein, L1and L2are each independently selected from a single bond or the following group consisting of: Optionally, L is selected from a single bond or the following group consisting of:

5. The arylamine compound according to claim 1, wherein, Ar1and Ar2are each 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; Optionally, 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, and optionally, in Ar1and Ar2, any two adjacent substituents form a benzene ring or a fluorene ring.

6. The arylamine compound according to claim 1, wherein, 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; 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; optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

7. The arylamine compound according to claim 1, wherein, Ar1and Ar2are the same or different and each independently selected from the following groups:

8. The arylamine compound according to claim 1, wherein, the same or different and each independently selected from the group consisting of:

9. The arylamine compound according to claim 1, wherein, in formula 1, is selected from the group consisting of 10. The arylamine compound according to claim 1, wherein, R1~R 12 one and only one of R1to R6is selected from the group consisting of the structure of Formula A, and the remaining groups are each independently selected from hydrogen, deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, or naphthyl.

11. The arylamine compound according to claim 1, wherein, The arylamine compound is selected from the group consisting of the following compounds:

12. 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 1-11.

13. The organic electroluminescent device according to claim 12, wherein The functional layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a guest material; the host material comprises the arylamine compound.

14. An electronic device, characterized by The organic electroluminescent device according to claim 12 or 13.

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