Arylamine compound, organic electroluminescent device and electronic apparatus
By using aromatic amine compounds with a phenanthro[4,3-b]benzofuran core structure as hole-transporting red light host materials, the shortcomings of organic electroluminescent devices in terms of lifespan and efficiency are solved, and the device performance is improved.
Patent Information
- Application Number
- PCT/CN2025/084824
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2024-04-11
- Filing Date
- 2025-03-25
- Publication Date
- 2025-10-16
AI Technical Summary
Existing organic electroluminescent devices have deficiencies in lifespan and efficiency, especially in large-area display devices due to high driving voltage. It is necessary to improve the main material of the light-emitting layer to enhance performance.
An aromatic amine compound with a phenanthro[4,3-b]benzofuran core structure is used as a hole-transporting red light host material, which is connected with an aromatic amine hole-transporting fragment at a specific position to enhance the intermolecular force, improve the carrier balance, and increase the exciton generation and utilization efficiency.
It improves the luminous efficiency and life of organic electroluminescent devices, broadens the carrier recombination area, strengthens the intermolecular force, and improves film-forming properties.
Smart Images

Figure CN2025084824_16102025_PF_FP_ABST
Abstract
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. CN202410439822.3, filed on April 11, 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 as shown in Formula II below:
[0008] In Formula II, D represents deuterium, and n represents the number of deuterium, selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;
[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] Ar1is selected from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group;
[0011] Ar2is 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;
[0012] 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.
[0013] 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 of the first aspect.
[0014] In some embodiments, the organic electroluminescent device is selected from a red organic electroluminescent device.
[0015] According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
[0016] The compound of the present application comprises phenanthro[4,3-b]benzofuran in its structure The mother nucleus structure is connected with arylamine hole transport segment through specific positions (5th and 6th positions) to serve as a hole transport type red light host material. Firstly, the special fused mode of phenanthrene and benzofuran ensures that the mother nucleus of phenanthro[4,3-b]benzofuran has a relatively appropriate first excited triplet state energy level, which is suitable as a segment of a red light host material. Secondly, the mother nucleus structure of phenanthro[4,3-b]benzofuran has a relatively large conjugated system, which can enhance the intermolecular force and improve the hole mobility of the compound after being connected with the arylamine hole transport segment through the 5th and 6th positions. Thirdly, when the arylamine is connected to the 5th or 6th position of the mother nucleus of phenanthro[4,3-b]benzofuran, the molecular torsion degree is relatively large, which can endow the compound with good film-forming property. The arylamine group adjacent to the mother nucleus of the compound does not contain other substituents with a volume larger than that of hydrogen (or deuterium), so as to avoid affecting the spatial conformation of the arylamine group. When the compound 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 light-emitting efficiency and service life of the device can be improved. BRIEF DESCRIPTION OF DRAWINGS
[0017] The accompanying drawings are included to provide a further understanding of the present application, and constitute a part of the specification, help to explain the present application, and together with the specific embodiments below, but do not constitute a limitation on the present application.
[0018] FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
[0019] FIG. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
[0020] Reference signs 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
[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 the present application 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 as shown in the following Formula II:
[0023] In Formula II, D represents deuterium, and n represents the number of deuterium, which is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;
[0024] 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;
[0025] Ar1is selected from a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group;
[0026] Ar2is 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 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.
[0028] In some embodiments, the arylamine compound described in the present application has a structure as shown in the following Formula I:
[0029] In Formula I, L, L1, L2, Ar1and Ar2have the same meanings as in Formula II. 2、 Ar1and Ar2both have the same meanings as in Formula II.
[0030] In the present application, the term "optionally" or "optional" means that the event or circumstance described subsequently can or can not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes the case where any two adjacent substituents form a ring, and the case where any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include the case where two substituents are on the same atom, and the case where one substituent is on each of two adjacent atoms; in the case where 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 attached; in the case where one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.
[0031] In the present application, the term "optionally" or "optional" means that the event or circumstance described subsequently can or can not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes the case where any two adjacent substituents form a ring, and the case where any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include the case where two substituents are on the same atom, and the case where one substituent is on each of two adjacent atoms; in the case where 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 attached; in the case where one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.
[0032] In the present application, the description "each of... is independently" and "each of... is independently" and "each of... is independently" can be used interchangeably, and should be interpreted broadly, and can mean that the specific options expressed by the same symbols in different groups do not affect each other, or 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, means that formula Q-1 represents a benzene ring with q substituents R", each R" can be the same or different, and the options for each R" do not affect each other; formula Q-2 represents a biphenyl, each benzene ring has q substituents R", the number 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 for each R" do not affect each other.
[0033] In the present application, the term "substituted or unsubstituted" means that the functional group described after the term can or can not have a substituent (hereinafter, for the sake of description, the substituents will be collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl with a substituent Rc or aryl without a substituent. The aforementioned substituent Rc can be, for example, deuterium, fluorine, cyano, a halogen group, a heteroaryl group, an aryl group, a deuterated aryl group, a trialkylsilyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, an alkoxy group, an alkylthio group, a cycloalkyl group, etc. The number of substituents can be one or more.
[0034] In the present application, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.
[0035] 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 having a carbon atom number of 12, the total number of carbon atoms of the arylene group and all substituents thereon is 12.
[0036] In the present application, the hydrogen atom in the structure of a compound includes various isotopes of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
[0037] In the present application, "D" in the structural formula of a compound indicates deuterium.
[0038] In the present application, a saturated or unsaturated 3-15-membered carbocyclic ring refers to a carbon ring containing 3-15 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.
[0039] In the present application, an aryl group refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group can be a monocyclic aryl group (for example, 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 connected by carbon-carbon bonds, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bonds, two or more fused ring aryl groups connected by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bonds can also be considered as aryl groups in the present application. Among them, the fused ring aryl group may, for example, include a bicyclic fused aryl group (for example, naphthyl), a tricyclic fused aryl group (for example, phenanthryl, fluorenyl, anthryl), 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, spirobifluorenyl anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, triphenylene pyrenyl, benzophenanthryl, fluorenyl, spirobifluorenyl
[0040] In the present application, the arylene group refers to a divalent group formed by further losing one or more hydrogen atoms from the aryl group.
[0041] In the present application, the terphenyl group includes
[0042] 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.
[0043] In the present application, the fluorenyl group can be substituted with one or more substituents, and in the case where the above fluorenyl group is substituted, the substituted fluorenyl group can be:
[0044] In the present application, the aryl group as a substituent of L, L1, L2, Ar1, and Ar2 is exemplified by, but not limited to, a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a fluorenyl group, a dimethylfluorenyl group, and the like.
[0045] In the present application, the heteroaryl group refers to a monovalent aromatic ring or a derivative thereof, in which 1, 2, 3, 4, 5, or 6 heteroatoms are contained in the ring, and the heteroatom 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. Exemplarily, the heteroaryl group can include a thiophenyl 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 benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a thienothiophenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silylfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, but is not limited thereto.
[0046] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from the heteroaryl group.
[0047] In the present application, the number of carbon atoms of a 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.
[0048] In the present application, the heteroaryl group as a substituent of L, L1, L2, Ar1, and Ar2 is exemplified by, but not limited to, dibenzothiophenyl group, dibenzofuranyl group, and the like.
[0049] 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, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, and the like.
[0050] In the present application, the halogen group can be, for example, fluorine, chlorine, bromine, iodine.
[0051] In the present application, specific examples of the trialkylsilyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
[0052] In the present application, the 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 group.
[0053] In the present application, the 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 group.
[0054] In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms can be, for example, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the cycloalkyl group include, but are not limited to, cyclopentyl group, cyclohexyl group, adamantyl group.
[0055] In the present application, the number of carbon atoms of the deuterated alkyl group having 1 to 10 carbon atoms can be, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of the deuterated alkyl group include, but are not limited to, trideuteromethyl group.
[0056] 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 deuterated aryl groups include, but are not limited to, penta-deuterobenzene, tri-deuterobenzene.
[0057] In the present application, the number of carbon atoms of a halogenated alkyl group having 1 to 10 carbon atoms is, for example, 1, 2, 3, 4, 5, 6, 7, 8, or 10. Specific examples of halogenated alkyl groups include, but are not limited to, trifluoromethyl.
[0058] In the present application, a ring system formed of n atoms is an n-membered ring. For example, a phenyl group is a 6-membered ring. A 5- to 13-membered ring refers to a cyclic group having 5 to 13 ring atoms. A 3- to 15-membered ring is, for example, a cyclopentane (5-membered ring), a cyclohexane (6-membered ring), a benzene ring (6-membered ring), a naphthalene ring (10-membered ring), a fluorene ring (13-membered ring), and the like.
[0059] In the present application, means a chemical bond to which other groups are connected.
[0060] In the present application, an indefinite position connecting bond refers to a single bond extending from a ring system which indicates that one end of the connecting bond can be connected to any position in the ring system through which the bond passes, and the other end is connected to the rest of the molecule. For example, as shown in the following formula (f), the naphthyl group represented by formula (f) is connected to other positions in the molecule by two indefinite position connecting bonds that pass through the bicyclic ring, and the meaning represented thereby includes any of the possible connection modes shown in formulae (f-1) to (f-10):
[0061] For another example, as shown in the following formula (X'), the dibenzofuranyl group represented by formula (X') is connected to other positions in the molecule by one indefinite position connecting bond extending from the middle of one of the benzene rings, and the meaning represented thereby includes any of the possible connection modes shown in formulae (X'-1) to (X'-4):
[0062] In the present application, an indefinite position substituent refers to a substituent connected by a single bond extending from the center of a ring system, and indicates that the substituent can be connected 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 connected to the quinoline ring by one indefinite position connecting bond, and the meaning represented thereby includes any of the possible connection modes shown in formulae (Y-1) to (Y-7):
[0063] 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 atom count of 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, or a substituted or unsubstituted heteroarylene group having a carbon atom count of 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18.
[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 atom count of 6 to 15, or a substituted or unsubstituted heteroarylene group having a carbon atom count of 5 to 18.
[0065] In some embodiments, the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, cyano, a halogen group, an alkyl group having a carbon atom count of 1 to 4, a haloalkyl group having a carbon atom count of 1 to 4, a deuterated alkyl group having a carbon atom count of 1 to 4, a trialkylsilyl group having a carbon atom count of 3 to 7, a phenyl group, or a deuterated phenyl group.
[0066] 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.
[0067] In some embodiments, the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, or phenyl.
[0068] In some embodiments, L1and L2are the same or different, and each is independently selected from a single bond or the group consisting of:
[0069] In some embodiments, L is selected from a single bond or the group consisting of:
[0070] In some embodiments, L1and L2are the same or different, and each is independently selected from a single bond or the group consisting of:
[0071] In some embodiments, L is selected from a single bond or the group consisting of:
[0072] In some embodiments, Ar2is selected from substituted or unsubstituted aryl having a carbon count of 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, or substituted or unsubstituted heteroaryl having a carbon count of 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.
[0073] In some embodiments, Ar2is selected from substituted or unsubstituted aryl having a carbon count of 6 to 25, or substituted or unsubstituted heteroaryl having a carbon count of 12 to 18.
[0074] 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 a carbon count of 1 to 4, a deuterated alkyl group having a carbon count of 1 to 4, an alkyl group having a carbon count of 1 to 4, a cycloalkyl group having a carbon count of 5 to 10, an aryl group having a carbon count of 6 to 15, a heteroaryl group having a carbon count of 5 to 12, a trialkylsilyl group having a carbon count of 3 to 7, or a deuterated aryl group having a carbon count of 6 to 15, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.
[0075] In some embodiments, Ar2is 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.
[0076] 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.
[0077] In some embodiments, Ar1is selected from the group consisting of:
[0078] In some embodiments, Ar2is selected from the group consisting of:
[0079] In some embodiments, Ar1is selected from the group consisting of:
[0080] In some embodiments, Ar2is selected from the group consisting of:
[0081] In some embodiments, is selected from the group consisting of:
[0082] In some embodiments, is selected from the group consisting of:
[0083] In some embodiments, is selected from the group consisting of:
[0084] In some embodiments, the arylamine compound is selected from the group consisting of:
[0085] 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 according to the first aspect of the present application.
[0086] 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.
[0087] In some embodiments, the functional layer further comprises a hole transport region, the hole transport region comprising 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), the hole transport layer being located between the anode and the organic light-emitting layer, and the light-emitting adjustment layer being located between the first hole transport layer and the organic light-emitting layer.
[0088] In some embodiments, the functional layer further comprises a light-emitting layer, the light-emitting layer comprising a light-emitting layer host material and a dopant material, wherein the light-emitting layer host material comprises the arylamine compound according to the present application.
[0089] In some embodiments, the light-emitting layer host material is composed of the arylamine compound provided by the present application and other materials.
[0090] 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.
[0091] 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 comprising a metal and an oxide, for example, 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. In some preferred embodiments, a transparent electrode comprising indium tin oxide (ITO) is used as the anode.
[0092] 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 selected from the following compounds or any combination thereof:
[0093] In one embodiment, the first hole transport layer 321 is composed of HT-1.
[0094] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.
[0095] In one embodiment, 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 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:
[0096] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.
[0097] In some embodiments, 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. In some embodiments, 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 emits light.
[0098] In an embodiment of the present application, the host material of the organic light-emitting layer 330 can include a metal chelate compound, a bis-styryl 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 compound, a combination of two or more compounds. In some embodiments, the host material includes an aromatic amine compound of the present application.
[0099] In an embodiment of the present application, the guest material of the organic light-emitting layer 330 can be a compound or derivative thereof having a condensed aryl ring, a compound or derivative thereof having a heteroaryl ring, an aromatic amine derivative, or other materials, which are not particularly limited in the present application. The guest material is also known as a dopant or a dopant material. According to the type of light emission, it can be divided into fluorescent dopants and phosphorescent dopants. Specific examples of the phosphorescent dopant include, but are not limited to,
[0100] 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 a compound of the present application. The guest material can be, for example, RD-1.
[0101] In an embodiment of the present application, 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, which can be 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:
[0102] In an embodiment of the present application, the electron transport layer 340 is composed of ET-1 and LiQ.
[0103] 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. In some embodiments, a metal electrode comprising magnesium and silver is used as the cathode.
[0104] In some embodiments, 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).
[0105] 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.
[0106] 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.
[0107] 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.
[0108] Synthesis Examples
[0109] 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 methods described. For example, those skilled in the art will recognize that the synthesis of the non-exemplified compounds according to the present application can be successfully performed by modifications of the methods described in the present application by applying the techniques described in the present application and known in the art, by utilizing other appropriate reagents in place of those described in the present application, and / or by making routine modifications of reaction conditions. The starting materials for the syntheses described herein that are not commercially available can be prepared by those starting materials that are readily synthesized by those skilled in the art, or by using methods described in the literature.
[0110] Synthesis of Sub-a1:
[0111] Into a 500 mL three-necked flask, RM-1 (11.25 g, 50 mmol), RM-2 (11.35 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), tetrabutylammonium bromide (TBAB, 1.61 g, 5 mmol), toluene (120 mL), anhydrous ethanol (30 mL) and deionized water (30 mL) were added successively under nitrogen atmosphere. The reaction was stirred and heated to reflux for 8 h. After the system was cooled to room temperature, dichloromethane (100 mL x 3) was used to extract the product. The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. Silica gel column chromatography was performed on the crude product using dichloromethane / n-heptane as the mobile phase to obtain white solid Sub-a1 (10.27 g, yield 67%).
[0112] Referring to the synthesis method of Sub-a1, Sub-a2 was synthesized by using the reactant A shown in Table 1 to replace RM-2.
[0113] Table 1: Synthesis of Sub-a2
[0114] Synthesis of Sub-b1:
[0115] Into a 1000 mL three-necked flask, (methoxymethyl)triphenylphosphonium chloride (51.25 g, 149.5 mmol), potassium tert-butoxide (18.10 g, 161 mmol) and anhydrous tetrahydrofuran (225 mL) were added successively under nitrogen atmosphere. The system was cooled to -15 °C and maintained for 30 min. Then Sub-a1 (39.90 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 maintained at -15 °C during the addition process, and after the addition was completed, the reaction was stirred at -15 °C for 1 h. After that, the reaction system was allowed to warm to room temperature. Dichloromethane (200 mL x 3) was used to extract the product. The organic phase was combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure to obtain a crude product. Silica gel column chromatography was performed on the crude product using n-heptane / dichloromethane as the mobile phase to obtain red solid Sub-b1 (31.77 g, yield 73%).
[0116] Referring to the synthesis method of Sub-b1, Sub-b2 was synthesized by using the reactant B shown in Table 2 to replace Sub-a1.
[0117] Table 2: Synthesis of Sub-b2
[0118] Synthesis of Sub-c1:
[0119] Into a 1000 mL three-necked flask, Sub-b1 (39.84 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (500 mL) were added successively under nitrogen atmosphere, and the reaction was continued with stirring 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 with 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-c1 (20.90 g, yield 58%).
[0120] Sub-c2 was synthesized according to the synthetic method of Sub-c1 by using the reactant C shown in Table 3 instead of Sub-b1.
[0121] Table 3: Synthesis of Sub-c2
[0122] Synthesis of Sub-d1:
[0123] Into a 500 mL three-necked flask, Sub-c1 (15.14 g, 50 mmol), pinacol diboronic acid (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (160 mL) were added successively under nitrogen atmosphere, and stirring and heating were started. When the system was heated to 40°C, 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, and the reaction was continued with stirring at reflux overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, stirred thoroughly for 30 min, and then filtered under reduced pressure. The filter cake was washed with deionized water until neutral, and then washed with 100 mL of anhydrous ethanol to obtain a gray solid. The crude product was washed with n-heptane once, and then dissolved in 200 mL of toluene, and then passed through a silica gel column to remove the catalyst. After concentration, white solid Sub-d1 (15.18 g, yield 77%) was obtained.
[0124] Sub-d2 was synthesized according to the synthetic method of Sub-d1 by using the reactant D shown in Table 4 instead of Sub-c1.
[0125] Table 4: Synthesis of Sub-d2
[0126] Synthesis of Sub-e1:
[0127] Into a 1000 mL three-necked flask, Sub-dl (21.68 g, 55 mmol), m-chlorobromobenzene (9.57 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (220 mL), anhydrous ethanol (55 mL) and deionized water (55 mL) were added successively under nitrogen atmosphere. The reaction was stirred and heated to reflux for 8 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 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-el as a white solid (15.72 g, 83% yield).
[0128] Referring to the synthesis of Sub-el, intermediates Sub-e2 to Sub-e8 were synthesized using the reactants E shown in Table 5 instead of Sub-dl and reactants F instead of m-chlorobromobenzene.
[0129] Table 5: Synthesis of Sub-e2 to Sub-e8
[0130] Synthesis of Sub-fl:
[0131] Into a 500 mL three-necked flask, Sub-c2 (15.13 g, 50 mmol), 3- aminodibenzofuran (9.16 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 1 mmol), (2-dicyclohexylphosphino-2',4',6' triisopropylbiphenyl) (Xphos, 0.95 g, 2 mmol), sodium tert-butoxide (9.61 g, 100 mmol) and xylene (250 mL) were added successively under nitrogen atmosphere. The reaction was stirred and heated to reflux overnight. 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 sodium 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 / dichloromethane as the mobile phase to give Sub-fl as a white solid (16.40 g; 73% yield).
[0132] Referring to the synthesis of Sub-fl, intermediates Sub-f2 to Sub-f26 were synthesized using the reactants G shown in Table 6 instead of Sub-c2 and reactants H instead of 3-aminodibenzofuran.
[0133] Table 6: Synthesis of Sub-f2 to Sub-f26
[0134] Synthesis Example 1: Synthesis of compound 3
[0135] Into a 250 mL three-necked flask, Sub-f1 (11.24 g, 25 mmol), 4-bromobiphenyl-D9 (6.66 g, 27.5 mmol), tris(dibenzylideneacetone)dipalladium (0.916 g, 0.5 mmol), (2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were added successively under nitrogen atmosphere, and the reaction was stirred at reflux overnight. After the system was cooled to room temperature, the reaction mixture was extracted with dichloromethane (100 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 compound 3 (12.67 g; yield 83%, m / z = 611.26 [M+H]). + ).
[0136] Referring to the synthesis method of compound 3, the reactants J shown in Table 7 were used instead of Sub-f1, and the reactants K were used instead of 4-bromobiphenyl-D9 to synthesize the compounds of the application in Table 7.
[0137] Table 7: Synthesis of compounds of the application
[0138] NMR data of some compounds:
[0139] NMR data of compound 137: 1 H-NMR (400 MHz, CD2Cl2) δ ppm: 8.66 (d, 1H), 8.14 (d, 1H), 8.05 (d, 1H), 8.01-7.92 (m, 3H), 7.84 (s, 1H), 7.70-7.29 (m, 17H), 7.10-7.05 (m, 2H), 6.82 (d, 1H), 6.75 (s, 2H).
[0140] Preparation and evaluation of organic electroluminescent devices:
[0141] The present application 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 organic compound of the present application. Hereinafter, the organic electroluminescent device of the present application will be described in detail by way of Examples. However, the following Examples are merely examples of the present application, and are not intended to limit the present application.
[0142] Example 1: Red organic electroluminescent device
[0143] First, the anode was pre-processed by the following procedure: the ITO / Ag / ITO substrate with thicknesses of 1500 / 200 / 1500 A, respectively, was subjected to surface treatment using UV ozone and O2:N2 plasma to increase the work function of the anode, or the ITO substrate surface was cleaned with organic solvent to remove impurities and oil on the ITO substrate surface.
[0144] On the experimental substrate (anode), PD:HT-1 was co-evaporated at a deposition rate ratio of 2:98% to form a hole injection layer (HIL) with a thickness of 100 A, and then HT-1 was vacuum evaporated on the hole injection layer to form a hole transport layer with a thickness of 100 A.
[0145] Next, on the hole auxiliary layer, compound 3:RH-N:RD was co-evaporated at a ratio of 49:49:2 to form a red light-emitting layer (EML) with a thickness of 200 A.
[0146] On the light-emitting layer, compound ET-1 and LiQ were co-evaporated at a deposition rate ratio of 1:1 to form an electron transport layer (ETL) with a thickness of 100 A, Yb was 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) were mixed at a deposition rate of 1:9 and vacuum evaporated on the electron injection layer to form a cathode with a thickness of 200 A.
[0147] In addition, CP was vacuum evaporated on the above cathode as a cover layer with a thickness of 100 A, thereby completing the manufacture of the red organic electroluminescent device.
[0148] Examples 2-73
[0149] An organic electroluminescent device was prepared by the same method as Example 1, except that the compound X in Table 8 below was used instead of compound 3 in Example 1 when the light-emitting layer was prepared.
[0150] Comparative Examples 1-4
[0151] An organic electroluminescent device was produced using the same method as in Example 1, except that, in producing the light-emitting layer, Compound A, Compound B, Compound C, and Compound D were used instead of Compound 3 in Example 1, respectively.
[0152] In producing the organic electroluminescent device, the structures of the respective materials used in the comparative examples and the examples were as follows:
[0153] The organic electroluminescent devices produced in Examples 1-73 and Comparative Examples 1-4 were subjected to performance tests, and the IVL performance of the devices was tested at 10 mA / cm 2 , and the T95 device lifetime was tested at 20 mA / cm 2 . The test results are shown in Table 8 below.
[0154] Table 8
[0155] As can be seen from Table 8 above, when the compounds of the present application are used as the host material of the light-emitting layer of a red organic electroluminescent device, the device of Examples 1-73 has at least a 15.75% increase in luminous efficiency (Cd / A) and at least a 12.56% increase in T95 lifetime, as compared with Comparative Examples 1-4.
[0156] 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 aromatic amine compound, characterized in that The aromatic amine compound has a structure as shown in the following formula II: In formula II, D represents deuterium, and n represents the number of deuterium atoms, selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; L, L1 and L2 are the same or different and are each 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; Ar1 is selected from substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl; Ar2 is 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 Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 10 carbon atoms, haloalkyl group with 1 to 10 carbon atoms, deuterated alkyl group with 1 to 10 carbon atoms, alkoxy group with 1 to 10 carbon atoms, alkylthio group with 1 to 10 carbon atoms, trialkylsilyl group with 3 to 12 carbon atoms, aryl group with 6 to 20 carbon atoms, deuterated aryl group with 6 to 20 carbon atoms, heteroaryl group with 3 to 20 carbon atoms, cycloalkyl group with 3 to 10 carbon atoms; optionally, any two adjacent substituents form a saturated or unsaturated 3 to 15-membered ring.
2. The aromatic amine compound according to claim 1, characterized in that The aromatic amine compound has a structure as shown in the following formula I:
3. The aromatic amine compound according to claim 1 or 2, wherein L, L1 and L2 are the same or different and are each 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 5 to 18 carbon atoms; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, a halogen group, 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.
4. The aromatic amine compound according to any one of claims 1 to 3, wherein L, L1 and L2 are the same or different and 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 phenanthrenylene group, a substituted or unsubstituted dibenzothienylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted carbazolylene group; Optionally, the substituents in L, L1 and L2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl or phenyl.
5. The aromatic amine compound according to any one of claims 1 to 4, wherein L1 and L2 are the same or different and are each independently selected from the group consisting of a single bond or the following groups: Optionally, L is selected from the group consisting of a single bond or the following groups:
6. The aromatic amine compound according to any one of claims 1 to 5, wherein Ar2 is 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 Ar1 and Ar2 are 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.
7. The aromatic amine compound according to any one of claims 1 to 6, wherein Ar2 is 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 phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl; Optionally, the substituents in Ar1 and Ar2 are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuterophenyl, phenyl or naphthyl.
8. The aromatic amine compound according to any one of claims 1 to 7, wherein Ar1 is selected from the group consisting of: Optionally, Ar2 is selected from the group consisting of:
9. The aromatic amine compound according to any one of claims 1 to 8, wherein Selected from the group consisting of: Optionally, Selected from the group consisting of:
10. The aromatic amine compound according to any one of claims 1 to 9, wherein Selected from the group consisting of:
11. The aromatic amine compound according to any one of claims 1 to 10, wherein The aromatic amine compound is selected from the group consisting of the following compounds:
12. An organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that: The functional layer comprises the aromatic amine compound according to any one of claims 1 to 11; Optionally, the functional layer includes a light-emitting layer, and the light-emitting layer contains the aromatic amine compound.
13. An electronic device, characterized in that: The organic electroluminescent device according to claim 12 is included.
Citation Information
Patent Citations
Condensed-cyclic compound, method for preparing the condensed-cyclic compound and organic light-emitting device including the condensed-cyclic compound
CN103058987A
Condensed-cyclic compound and organic light-emitting diode comprising the same
CN103382178A
Organic compound, organic optoelectronic diode, and display device
CN107849000A
Organic light-emitting device
CN112939930A
Arylamine compound, composition containing arylamine compound and organic light-emitting device
CN119490493A