Arylamine compounds, organic electroluminescent devices and electronic devices

Abstract

The application 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. The arylamine compound contains a phenanthro[2,1-b]benzofuran parent nucleus structure. When the compound is used as a hole transport type material in a mixed type host material, the carrier balance in a light-emitting layer can be improved, the carrier recombination area is widened, the excitation generation and utilization efficiency is improved, and the light-emitting efficiency and the service life of the device are 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 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

[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 X is selected from O or S;

[0008] L, L1and L2are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 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, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms;

[0010] The substituents of M, 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 15 carbon atoms, a heteroaryl group having 3 to 12 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.

[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 each other, and a functional layer disposed between the anode and the cathode; the functional layer comprising 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 phenanthro[2,1-b]benzofuran parent structure in the structure of the compound, and the parent structure is connected to an arylamine hole transport segment through a specific position (position 13 ) as a hole transport type light-emitting host material. On the one hand, the special fused mode of phenanthrene and benzofuran ensures that the parent structure of phenanthro[2,1-b]benzofuran has a relatively suitable first excited triplet state energy level, which is suitable as a light-emitting host material segment; on the other hand, the parent structure of phenanthro[2,1-b]benzofuran has a relatively large conjugated system, which can enhance the intermolecular forces and improve the hole mobility of the compound after being connected to the arylamine hole transport segment through position 13. When the compound of the present application is used as a hole transport type 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 together with the following detailed description to explain the present application, but do not constitute a limitation of the present application.

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

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

[0017] Reference Signs

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

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

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

[0021] Exemplary embodiments now will be described more fully hereinafter with reference to the accompanying drawings; however, this application may be implemented in many different 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 thorough and complete, and fully convey the scope of the application to those skilled in the art. Like reference numerals refer to like elements throughout. The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting; it is to be understood that there can be other embodiments that are similar in nature to the described embodiments, and that individual features from one embodiment can be combined with individual features from another embodiment.

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

[0023]

[0024] wherein X is selected from O or S;

[0025] L, L1, and L2 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 20 carbon atoms;

[0026] 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 20 carbon atoms;

[0027] N, L1, L2, Ar1and Ar2are the same or different, and each is independently selected from the group consisting of deuterium, cyano, 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 15 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; and optionally, any two adjacent substituents form a saturated or unsaturated 3- to 15-membered ring.

[0028] In the present application, the term "optionally" 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- to 15-membered ring" includes the scenario in which any two adjacent substituents form a ring, as well as the scenario in which any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein when two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are both attached; and when one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.

[0029] In the present application, the term "optionally" 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- to 15-membered ring" includes the scenario in which any two adjacent substituents form a ring, as well as the scenario in which any two adjacent substituents each independently exist without forming a ring. "Any two adjacent" can include two substituents on the same atom, and can also include one substituent on each of two adjacent atoms; wherein when two substituents are on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are both attached; and when one substituent is on each of two adjacent atoms, the two substituents can be fused into a ring.

[0030] In the present application, the description "each independently" can be replaced by "respectively independently" and "each independently", and should be interpreted broadly, which means that the specific options expressed by the same symbols in different groups do not affect each other, and also means 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 the group consisting of hydrogen, deuterium, fluorine, chlorine, which means that formula Q-1 represents a benzene ring having q substituents R", and each R" can be the same or different, and the options for each R" do not affect each other; and formula Q-2 represents a biphenyl in which each benzene ring has q substituents R", and 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 for each R" do not affect each other.

[0031] In the present application, the term "substituted or unsubstituted" means that the functional group recited after the term can or can not have a substituent group (hereinafter, the substituent group will be collectively referred to as Rc). For example, "substituted or unsubstituted aryl" means aryl having a substituent group Rc or aryl having no substituent group. The substituent group Rc recited above, for example, can be deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, and the like. The number of substituent groups can be one or more.

[0032] In the present application, "a plurality of" means two or more, for example, two, three, four, five, six, and the like.

[0033] In the present application, the number of carbon atoms of a substituted or unsubstituted functional group means the total number of carbon atoms of the group and all substituents thereon. For example, if L1 is a substituted arylene group having 12 carbon atoms, the total number of carbon atoms of the arylene group and the substituents thereon is 12.

[0034] In the present application, the hydrogen atom in the structure of a compound includes various isotopes of the hydrogen element, for example, hydrogen (H), deuterium (D), or tritium (T).

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

[0036] In the present application, a saturated or unsaturated 5- to 13-membered carbocyclic ring means a carbon ring containing 5 to 13 ring atoms; for example, but not limited to, cyclopentane, cyclohexane, benzene ring, fluorene ring, and the like.

[0037] In the present application, aryl means 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 a carbon-carbon bond in conjugation, a monocyclic aryl group and a fused ring aryl group connected by a carbon-carbon bond in conjugation, or two or more fused ring aryl groups connected by a carbon-carbon bond in conjugation. That is, unless otherwise specified, two or more aromatic groups connected by a carbon-carbon bond in conjugation can also be regarded as an aryl group in the present application. The fused ring aryl group, for example, can include a bicyclic fused aryl group (for example, naphthyl), a tricyclic fused aryl group (for example, phenanthryl, fluorenyl, anthryl), and the like. The aryl group does not contain heteroatoms such as B, N, O, S, P, Se, and Si. Examples of the aryl group include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, quaterphenyl, quinquephenyl, triphenylene, perylenyl, benzo[9,10]phenanthryl, pyrenyl, benzofluoranthene, chrysene, phenanthrene, naphthacene, and the like.

[0038] In the present application, the arylene group referred to means a divalent group formed by further losing one or more hydrogen atoms from the aryl group. ​

[0039] In the present application, triphenyl group includes

[0040] In the present application, the number of carbon atoms of substituted or unsubstituted aryl (arylene) group can be 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 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.

[0041] In the present application, fluorenyl group can be substituted by one or more substituents, in the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group can be: and the like, but is not limited thereto.

[0042] In the present application, the aryl group as a substituent of L, L1, L2, Ar1and Ar2is exemplified by, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0043] In the present application, heteroaryl group refers to a monovalent aromatic ring or its derivative comprising 1, 2, 3, 4, 5 or 6 heteroatoms 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 a carbon-carbon bond in conjugation, and any of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Exemplarily, the heteroaryl group can include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalyl, phenoxazinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, thienothiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, sifluorenyl, dibenzofuranyl and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, but is not limited thereto.

[0044] 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.

[0045] 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.

[0046] In the present application, an 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, or 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

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

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

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

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

[0051] In the present application, the number of carbon atoms of a 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, a cyclopentyl group, a cyclohexyl group, an adamantyl group.

[0052] In the present application, the number of carbon atoms of a 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, a trideuteromethyl group.

[0053] In the present application, the number of carbon atoms of a haloalkyl 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 haloalkyl group include, but are not limited to, a trifluoromethyl group.

[0054] In the present application, refers to a chemical bond to which other groups are mutually connected.

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

[0056]

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

[0058]

[0059] In the present application, an indefinite substituent refers to a substituent attached by a single bond extending from the center of a ring system, and indicates that the substituent can be attached to any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by formula (Y) is attached to the quinoline ring by one indefinite single bond, and the meaning represented thereby includes any of the possible attachment modes shown in formulae (Y-1) to (Y-7):

[0060]

[0061] In some embodiments, L, L1, and L2 are the same or different, and each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0062] 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 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, or a phenyl group.

[0063] In some embodiments, L, L1and L2are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted carbazolylene.

[0064] Optionally, the substituents in L, L1and L2are the same or different, and each is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, pentadeuteriophenyl, or phenyl.

[0065] In some embodiments, L1and L2are each independently selected from a single bond or the group consisting of:

[0066]

[0067] In some embodiments, L is selected from a single bond or the group consisting of:

[0068]

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

[0070]

[0071] In some embodiments, L is selected from a single bond or the group consisting of:

[0072]

[0073]

[0074] 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 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, or 18 carbon atoms.

[0075] 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.

[0076] Optionally, the substituents in Ar1and Ar2are each independently selected from deuterium, a halogen group, a cyano group, a halogenated alkyl 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 form a benzene ring or a fluorene ring.

[0077] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0078] Optionally, the substituents in Ar1and Ar2are each independently selected from deuterium, a halogen group, a cyano group, a halogenated alkyl 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 form a benzene ring or a fluorene ring.

[0079] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0080]

[0081] In some embodiments, Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

[0082]

[0083]

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

[0085]

[0086]

[0087] In some embodiments, in Formula 1, is selected from the following groups:

[0088]

[0089]

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

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] 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.

[0103] 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.

[0104] 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), 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.

[0105] 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 provided by the present application.

[0106] In some embodiments, the light-emitting layer host material is composed of the arylamine compound provided by the present application and other materials.

[0107] According to a specific embodiment, the organic electroluminescent device is as shown in the following structure:Figure 1 As shown, the 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 are sequentially stacked.

[0108] In the present application, the anode 100 includes an anode material, which is preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of 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, a transparent electrode including indium tin oxide (ITO) as the anode is included.

[0109] In the present application, the hole transport layer and the hole adjustment layer can each include 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:

[0110]

[0111]

[0112] In one embodiment, the first hole transport layer 321 is composed of HT-1.

[0113] In one embodiment, the light-emitting adjustment layer 322 is composed of HT-2.

[0114] Optionally, a hole injection layer 310 is further provided between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the hole transport layer 321. The hole injection layer 310 can be selected from benzidine derivatives, starburst 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, for example, selected from the following compounds or any combination thereof:

[0115]

[0116]

[0117] In one embodiment of the present application, the hole injection layer 310 is composed of PD and HT-1.

[0118] 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.

[0119] 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 compound, a combination of two or more compounds. Optionally, the host material includes the arylamine compound of the present application.

[0120] 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 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,

[0121]

[0122] (RD)、

[0123]

[0124] [Ir(flq)2(acac)] (Ir(Mphq)3).

[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-1.

[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] (ET),

[0128] (BmPyPhB),

[0129] In an embodiment of the present application, the electron transport layer 340 is composed of ET and LiQ.

[0130] In the present application, the cathode 200 includes a cathode material, which is a material having a small work function that is helpful for electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; or a multi-layered material such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca. Alternatively, a metal electrode including magnesium and silver is included as the cathode.

[0131] Alternatively, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability of injecting electrons into the electron transport layer 340. The electron injection layer 350 can include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or the like, or can include a complex of an alkali metal and an organic material. In an embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0132] The third aspect of the present application provides an electronic device including the organic electroluminescent device according to the second aspect of the present application.

[0133] According to an embodiment, as shown in Figure 2 The electronic device provided is electronic device 400, which includes 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, which can include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency lighting lamp, an optical module, and the like.

[0134] The synthesis method of the arylamine compound of the present application will be specifically described below in connection with the synthesis examples, but the present application is not limited thereto.

[0135] Synthesis Examples

[0136] Those skilled in the art will recognize that the chemical reactions described in the application can be used to prepare many of the arylamine compounds of the application, and that other methods for preparing the compounds of the application are also within the scope of the application. For example, the synthesis of the non-exemplified compounds according to the application can be successfully performed by modifications apparent to those skilled in the art, by analogy with the procedures described herein or through the use of other known reagents and techniques. The compounds of the application that are not mentioned in the synthetic procedures are obtained from commercial sources.

[0137] Synthesis of Sub-al:

[0138]

[0139] To a 500 mL three-necked flask, RM-1 (11.35 g, 55 mmol), RM-2 (11.25 g, 50 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (120 mL), anhydrous ethanol (30 mL) and deionized water (30 mL) were added successively under nitrogen atmosphere. The reaction was stirred and heated to reflux for 8 h. After the system was cooled to room temperature, the mixture was extracted with dichloromethane (100 mL x 3 times). The organic phases were combined and dried over anhydrous magnesium sulfate. 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 dichloromethane / n-hexane as the mobile phase to give Sub-al (10.27 g, 67% yield) as a white solid.

[0140] Following the procedure for the synthesis of Sub-al, intermediate Sub-a2 was synthesized by using the reactant A shown in Table 1 instead of RM-2.

[0141] Table 1: Synthesis of Sub-a2 and Sub-a3

[0142]

[0143] Synthesis of Sub-bl:

[0144]

[0145] Into a 1000 mL three-necked flask, Sub-b1 (39.87 g, 130 mmol), (methoxymethyl)triphenylphosphonium chloride (74.38 g, 217 mmol) and anhydrous tetrahydrofuran (500 mL) were added successively under nitrogen atmosphere. The system was cooled to 0 °C with an ice-water bath. Then a solution of potassium tert-butoxide in anhydrous tetrahydrofuran (1 M, 220 mL) was added slowly dropwise. After the addition was completed, the system was allowed to warm up to room temperature and the stirring was continued for 6 h. The reaction solution was poured into 1000 mL of deionized water and extracted with ethyl acetate (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 give a crude product. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to give solid Sub-b1 (33.95 g, yield 78%).

[0146] Referring to the synthesis method of Sub-b1, the intermediate Sub-b2 was synthesized by using the reactant B shown in Table 2 instead of Sub-a1.

[0147] Table 2: Synthesis of Sub-b2

[0148]

[0149] Synthesis of Sub-c1:

[0150]

[0151] Into a 1000 mL three-necked flask, Sub-b1 (39.84 g, 119 mmol), Eaton’s reagent (4.5 mL) and chlorobenzene (400 mL) were added successively under nitrogen atmosphere. The system was heated to reflux and the stirring was continued for 4 h. After the system was cooled to room temperature, the reaction solution was poured into 1000 mL of deionized water and neutralized with saturated sodium hydroxide solution. Then it was 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 give a crude product. The crude product was purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to give white solid Sub-c1 (24.14 g, yield 67%).

[0152] Referring to the synthesis method of Sub-c1, the intermediate Sub-c2 was synthesized by using the reactant C shown in Table 3 instead of Sub-b1.

[0153] Table 3: Synthesis of Sub-c2

[0154]

[0155] Synthesis of Sub-d1:

[0156]

[0157] Into a 500 mL three-necked flask, Sub-c1 (15.14 g, 50 mmol), bis(pinacolato)diboron (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (150 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to 40 °C. Then tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphino-2',4',6' triisopropyl biphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added. The system was warmed to reflux, and the reaction was stirred overnight. After the system was cooled to room temperature, 200 mL of water was added to the system, and the stirring was continued for 30 min. The filter cake was washed with deionized water until neutral, and then dissolved with 100 mL of dichloromethane. After drying with anhydrous sodium sulfate, the organic phase was filtered, and the solvent was removed by distillation under reduced pressure to obtain a crude product. The crude product was dissolved in 200 mL of toluene, and then purified by silica gel column to remove the catalyst. After concentration, white solid Sub-d1 (13.20 g, yield 67%) was obtained.

[0158] Referring to the synthesis method of Sub-d1, intermediate Sub-d2 was synthesized by using the reactant D shown in Table 4 instead of Sub-c1.

[0159] Table 4: Synthesis of Sub-d2

[0160]

[0161]

[0162] Synthesis of Sub-e1:

[0163]

[0164] Into a 1000 mL three-necked flask, m-chlorobromobenzene (9.57 g, 50 mmol), Sub-d2 (22.57 g, 55 mmol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), anhydrous sodium carbonate (10.60 g, 100 mmol), toluene (220 mL), anhydrous ethanol (55 mL) and deionized water (55 mL) were sequentially added under nitrogen atmosphere. The stirring and heating were started, and the system was warmed to reflux for 8 h. After the system was cooled to room temperature, the extraction was performed with dichloromethane (100 mL x 3 times). The combined organic phase was dried with anhydrous magnesium sulfate, filtered, and then 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-e1 (16.58 g, yield 84%).

[0165] Referring to the synthesis method of Sub-e1, using the reactant E shown in Table 5 to replace m-chlorobromobenzene, and reactant F to replace Sub-d2, intermediates Sub-e2 to Sub-e8 are synthesized.

[0166] Table 5: Synthesis of Sub-e2 to Sub-e8

[0167]

[0168]

[0169] Synthesis of compound 4:

[0170]

[0171] Into a 250 mL three-necked flask, Sub-c1 (11.31 g, 25 mmol), RM-3 (6.56 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, dichloromethane (100 mL x 3 times) was used for extraction, and the combined organic phase was dried with anhydrous sodium 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 n-heptane / dichloromethane as the mobile phase to obtain a white solid (11.58 g; yield 77%, m / z = 602.21 [M+H]). + ).

[0172] Referring to the synthesis method of compound 4, using the reactant G shown in Table 6 to replace Sub-c1, and reactant H to replace RM-3, the compounds of the application in Table 6 are synthesized.

[0173] Table 6: Synthesis of compounds of the application

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] NMR data of some compounds:

[0184] NMR data of compound 137: 1 H-NMR (400 MHz, CD2Cl2) δ ppm: 8.28 (d, 1H), 8.19 (d, 1H), 7.99-7.97 (m, 2H), 7.88 (d, 1H), 7.81 (d, 1H), 7.67-7.26 (m, 17H), 7.21-7.12 (m, 4H), 7.06 (s, 1H), 6.93 (s, 1H), 6.87 (d, 1H), 6.55 (d, 1H).

[0185] 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 above-mentioned organic compound of the present application. Hereinafter, the organic electroluminescent device of the present application will be explained in detail by examples. However, the following examples are only examples of the present application, and not limit the present application.

[0186] Example 1: Red organic electroluminescent device

[0187] First, the anode is pre-processed by the following process: the ITO / Ag / ITO substrate with thickness of 1500 / 200 / 1500 A is surface-treated by UV ozone and O2:N2 plasma to increase the work function of the anode, or the ITO substrate surface is cleaned by organic solvent to remove impurities and oil on the ITO substrate surface.

[0188] On the experimental substrate (anode), PD:HT-1 is co-evaporated at a ratio of 2%:98% to form a hole injection layer (HIL) with a thickness of 100 A, and then HT-1 is vacuum evaporated on the hole injection layer to form a hole transport layer with a thickness of 200 A.

[0189] Next, on the hole auxiliary layer, compound 1:RH-N:RD is co-evaporated at a ratio of 49%:49%:2% to form a red light emitting layer (EML) with a thickness of 200 A.

[0190] ​​​​​On the light-emitting layer, compound ET and LiQ were co-evaporated with a ratio of 1:1 of evaporation rate to form a light-emitting layer with a thickness of 30 A. A thick electron transport layer (ETL) was formed on the light-emitting layer, Yb was evaporated on the electron transport layer to form an electron injection layer (EIL) with a thickness of 20 A, then magnesium (Mg) and silver (Ag) were mixed with a ratio of 1:9 of evaporation rate and vacuum evaporated on the electron injection layer to form a cathode with a thickness of 200 A. In addition, CP was vacuum evaporated on the cathode as a cover layer with a thickness of 20 A, thus completing the manufacture of the red organic electroluminescent device.

[0191] In addition, CP was vacuum evaporated on the cathode as a cover layer with a thickness of 20 A, thus completing the manufacture of the red organic electroluminescent device.

[0192] Examples 2-60

[0193] In addition, except that compound X in Table 7 below was used instead of compound 1 in Example 1 when the light-emitting layer was prepared, the organic electroluminescent device was prepared by the same method as Example 1.

[0194] Comparative Examples 1-4

[0195] In addition, except that compound A, compound B, compound C and compound D were used instead of compound 1 in Example 1, respectively, when the light-emitting layer was prepared, the organic electroluminescent device was prepared by the same method as Example 1.

[0196] In the preparation of the organic electroluminescent device, the structures of the respective materials used in the comparative examples and the examples are as follows:

[0197]

[0198] The organic electroluminescent devices prepared in Examples 1-60 and Comparative Examples 1-4 were tested for performance, and the IVL performance of the devices was tested under the condition of 10 mA / cm 2 , the T95 device lifetime was tested under the condition of 20 mA / cm 2 , and the test results are shown in Table 7 below.

[0199] Table 7

[0200]

[0201]

[0202] As can be seen from Table 6 above, when the compound of the present application is used as the light-emitting layer host material of the red organic electroluminescent device, the device of Examples 1-60 has at least 12.0% higher luminous efficiency (Cd / A) and at least 13.3% longer T95 lifetime compared to Comparative Examples 1-4.

[0203] ​​The preferred embodiments of the present application are described in detail above with reference to the 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 technical concept of the present application, and these simple modifications all belong to the protection scope of the present application.

Claims

1. An arylamine compound characterized in that, The arylamine compound has a structure represented by Formula 1: wherein X is selected from O or S; 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 fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazolylene group; the substituents in L, L1, and L2 are the same or different, and each is independently selected from deuterium, fluorine, a cyano group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a trifluoromethyl group, a trideuteromethyl group, a trimethylsilyl group, a pentadeuteriophenyl group, or a phenyl group; Ar1and Ar2are the same or different, and each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted triphenylyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazolylene group; 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.

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

3. The arylamine compound according to claim 1, wherein, Ar1, Ar2are the same or different and each independently selected from the following groups:

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

5. The arylamine compound according to claim 1, wherein, in formula 1, is selected from the group consisting of 6. The arylamine compound according to claim 1, wherein, The arylamine compound is selected from the group consisting of the following compounds:

7. An organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; characterized in that, The functional layer comprises the arylamine compound according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein The functional layer comprises a light-emitting layer, and the light-emitting layer comprises a host material and a guest material; and the host material comprises the arylamine compound.

9. An electronic device, characterized by The organic electroluminescent device according to claim 7 or 8.

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