Arylamine compound, organic electroluminescent device and electronic device

Abstract

The invention relates to the technical field of organic electroluminescent materials, and provides an arylamine compound, an organic electroluminescent device containing the arylamine compound and an electronic device. The arylamine compound comprises a mother nucleus structure of phenanthro [2, 1-b] benzofuran, and when the compound is used as a hole transport type material in a mixed type main body material, the carrier balance in a light-emitting layer can be improved, the carrier recombination area can be widened, the exciton generation and utilization efficiency can be improved, the light-emitting efficiency of a device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present application relates to the technical field of organic electroluminescent materials, and in particular to aromatic amine compounds and organic electroluminescent devices and electronic devices containing the same. Background Art

[0002] With the development of electronic technology and the progress of materials science, the application scope of electronic components for realizing electroluminescence or photoelectric conversion is becoming more and more extensive. Organic electroluminescent devices (OLEDs) generally include: a cathode and an anode arranged opposite to each other, 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 includes an organic light-emitting layer, a hole transport layer, an electron transport layer, etc. When a voltage is applied to the positive and negative electrodes, the two electrodes generate an electric field. 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. The excitons are in an excited state and release energy outward, thereby causing the electroluminescent layer to emit light outward.

[0003] In the existing organic electroluminescent devices, the main problems are reflected in the lifespan and efficiency. With the large-area display, the driving voltage also increases. The research on improving the performance of OLED light-emitting devices includes: reducing the driving voltage of the device, improving the luminous efficiency of the device, and improving the service life of the device. In order to improve the device performance of OLED, a multi-layer sandwich structure is usually adopted when designing the device structure, that is, the anode, cathode and multiple organic functional layers together form a complete device. The main material of the light-emitting layer can be one or more. The main material is a material that can accept positively charged hole carriers and negatively charged electron carriers and combine the two for effective energy transfer. It usually has a higher first triplet energy level and is a very important part of the organic electroluminescent device. It is necessary to continue to develop new main materials for the light-emitting layer to further improve the performance of organic electroluminescent devices. Summary of the invention

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

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

[0006]

[0007] Wherein, X is selected from O or S;

[0008] L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;

[0009] Ar1 and Ar2 are the same or different and are each 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;

[0010] The substituents of M, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, 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, an organic electroluminescent device is provided, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the above-mentioned aromatic amine compound.

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

[0013] The structure of the compound of the present application contains a nucleus structure of phenanthro[2,1-b]benzofuran, and the nucleus is ) is connected with an aromatic amine hole transport fragment as a hole transport type luminescent host material. On the one hand, the special fusion mode of phenanthrene and benzofuran ensures that the parent nucleus of phenanthrene [2,1-b] benzofuran has a more suitable first excited triplet energy level, which is suitable as a fragment of the luminescent host material; on the other hand, the parent nucleus structure of phenanthrene [2,1-b] benzofuran has a larger conjugated system, and after connecting it with an aromatic amine hole transport fragment through position 13, it can enhance the intermolecular force and improve the hole mobility of the compound. When the compound of the present application is used as a hole transport material in a hybrid luminescent host material, it can improve the carrier balance in the luminescent layer, broaden the carrier recombination area, improve the exciton generation and utilization efficiency, and improve the device luminescence efficiency and life. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The accompanying drawings are used to provide further understanding of the present application and constitute a part of the specification. Together with the following specific embodiments, they are used to explain the present application, but do not constitute a limitation to the present application.

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

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

[0017] Reference numerals

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

[0019] 321, first hole transport layer 322, luminescence 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 will now be described more fully with reference to the accompanying drawings. However, exemplary embodiments can be implemented in a variety of 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 comprehensive and complete and the concepts of the exemplary embodiments are fully conveyed to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, many specific details are provided to provide a full understanding of the embodiments of the present application.

[0022] In a first aspect, the present application provides an aromatic amine compound having a structure shown in 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, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms;

[0026] Ar1 and Ar2 are the same or different and are each 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] The substituents of N, L1, L2, Ar1 and Ar2 are the same or different and are independently selected from deuterium, cyano, halogen group, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, 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 the present application, the terms "optionally" and "optionally" mean that the event or environment described subsequently may or may not occur. For example, "optionally, any two adjacent substituents form a saturated or unsaturated 3-15 membered ring" includes: the scenario where any two adjacent substituents form a ring, and the scenario where any two adjacent substituents exist independently and do not form a ring. "Any two adjacent" can include two substituents on the same atom, and can also include two adjacent atoms each having one substituent; wherein, when there are two substituents on the same atom, the two substituents can form a saturated or unsaturated spiro ring with the atom to which they are commonly connected; when there is one substituent on two adjacent atoms respectively, the two substituents can be fused into a ring.

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

[0030] In this application, the descriptions "each... independently is" and "... are independently" and "... are independently" are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols 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, and chlorine, which means: Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other; Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, 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 of each R" do not affect each other.

[0031] In the present application, the term "substituted or unsubstituted" means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl with a substituent Rc or an aryl without a substituent. The above-mentioned substituent, i.e., Rc, can be, for example, deuterium, fluorine, cyano, heteroaryl, aryl, deuterated aryl, trialkylsilyl, alkyl, haloalkyl, deuterated alkyl, cycloalkyl, etc. The number of substituents can be 1 or more.

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

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

[0034] The hydrogen atoms in the structures of the compounds of the present application include various isotope atoms of the hydrogen element, such as hydrogen (H), deuterium (D) or tritium (T).

[0035] The "D" in the structural formula of the compound of the present application represents deuteration.

[0036] In the present application, a saturated or unsaturated 5-13-membered carbon ring refers to a carbon ring containing 5-13 ring atoms, such as but not limited to cyclopentane, cyclohexane, benzene ring, fluorene ring, etc.

[0037] In the present application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl. In other words, aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation. That is, unless otherwise specified, two or more aromatic groups connected by carbon-carbon bond conjugation can also be regarded as aryl of the present application. Wherein, condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc. Aryl 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, anthracenyl, phenanthrenyl, biphenyl, terphenyl, quaterphenyl, pentaphenyl, triphenylene, peryl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl, Ji et al.

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

[0039] In the present application, terphenyl includes

[0040] In the present application, the carbon number of the substituted or unsubstituted aryl (arylene) group may 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, and 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, the fluorenyl group may be substituted by one or more substituents. When the fluorenyl group is substituted, the substituted fluorenyl group may be: etc., but not limited thereto.

[0042] In the present application, the aryl group as a substituent of L, L1, L2, Ar1 and Ar2 is exemplified but not limited to phenyl, naphthyl, phenanthrenyl, biphenyl, fluorenyl, dimethylfluorenyl and the like.

[0043] In the present application, heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing 1, 2, 3, 4, 5 or 6 heteroatoms in the ring, and the heteroatoms may be one or more of B, O, N, P, Si, Se and S. The heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring. By way of example, the heteroaryl group may include a thienyl group, a furyl 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 pyrimidyl group, a triazine 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 pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothienyl group, a dibenzothienyl group, a thienothiphenyl group, a benzofuranyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, a silyfluorenyl group, a dibenzofuranyl group, and an N-phenylcarbazolyl group, an N-pyridylcarbazolyl group, an N-methylcarbazolyl group, and the like, without being limited thereto.

[0044] In the present application, the heteroarylene group refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a heteroaryl group.

[0045] In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl (heteroarylene) can be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 or 20. In some embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 30, in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 3 to 18, and in other embodiments, the substituted or unsubstituted heteroaryl is a substituted or unsubstituted heteroaryl having a total carbon number of 12 to 18.

[0046] In the present application, the alkyl group having 1 to 10 carbon atoms may 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 in the alkyl group may 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, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.

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

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

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

[0050] In the present application, a deuterated alkyl group refers to an alkyl group substituted with one or more deuterium groups. Specific examples of deuterated alkanes include, but are not limited to, trideuterated methyl groups.

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

[0052] In the present application, the carbon number of the deuterated alkyl group having 1 to 10 carbon atoms is, 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, trideuterated methyl group.

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

[0054] In this application, Refers to the chemical bonds that connect to other groups.

[0055] In this application, no single bond extending from the ring system is involved in the positioning of the connecting bond. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule. For example, as shown in the following formula (f), the naphthyl represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that pass through the bicyclic ring. The meaning represented by it includes any possible connection mode shown in formula (f-1) to formula (f-10):

[0056]

[0057] For another example, as shown in the following formula (X'), the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and the meaning represented by it includes any possible connection mode shown in formula (X'-1) to formula (X'-4):

[0058]

[0059] The non-positioning substituent in the present application refers to a substituent connected by a single bond extending from the center of the ring system, which means 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 through a non-positioning connection bond, and the meaning represented includes any possible connection mode shown in formula (Y-1) to formula (Y-7):

[0060]

[0061] In some embodiments, 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, 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 are independently selected from deuterium, cyano, halogen group, alkyl group with 1 to 4 carbon atoms, haloalkyl group with 1 to 4 carbon atoms, deuterated alkyl group with 1 to 4 carbon atoms, trialkylsilyl group with 3 to 7 carbon atoms or phenyl group.

[0063] In some embodiments, L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzothienylene, a substituted or unsubstituted dibenzofuranylene, or a substituted or unsubstituted carbazolylene.

[0064] 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, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

[0065] In some embodiments, L1 and L2 are each independently selected from a single bond or the group consisting of:

[0066]

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

[0068]

[0069] In some embodiments, L1 and L2 are the same or different and are each independently selected from a single bond or the group consisting of the following groups:

[0070]

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

[0072]

[0073]

[0074] In some embodiments, Ar1 and Ar2 are 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, and 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, Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 18 carbon atoms.

[0076] 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, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

[0077] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl.

[0078] 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, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl.

[0079] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0080]

[0081] In some embodiments, Ar1 and Ar2 are the same or different and are each independently selected from the following groups:

[0082]

[0083]

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

[0085]

[0086]

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

[0088]

[0089]

[0090] In some embodiments, the aromatic amine 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 aromatic amine compound described in the first aspect of the present application.

[0103] The aromatic amine compound provided in the present application can be used to form at least one organic film layer in the functional layer to improve the luminous efficiency and life span of the organic electroluminescent device.

[0104] Optionally, the functional layer also includes a hole transport zone, the hole transport zone includes a hole transport layer (also called a first hole transport layer) and a luminescence adjustment layer (also called 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 luminescence adjustment layer is located between the first hole transport layer and the organic light-emitting layer.

[0105] Optionally, the functional layer further includes a light-emitting layer, and the light-emitting layer includes a light-emitting layer main material and a doping material, wherein the light-emitting layer main material includes the aromatic amine compound of the present application.

[0106] In some embodiments, the main material of the light-emitting layer is composed of the aromatic amine compound provided in the present application and other materials.

[0107] According to a specific embodiment, the organic electroluminescent device is as follows Figure 1 As shown, it includes an anode 100, a hole injection layer 310, a first hole transport layer 321, a light emitting adjustment layer 322, an organic light emitting layer 330, an electron transport layer 340, an electron injection layer 350 and a cathode 200 which are stacked in sequence.

[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 anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined 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 not limited thereto. Preferably, a transparent electrode including indium tin oxide (indium tin oxide) (ITO) as an anode is included.

[0109] In the present application, the hole transport layer and the hole adjustment layer may include one or more hole transport materials, respectively. The hole transport material may be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and may be specifically 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 luminescence 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 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular limitation thereto. 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 may be composed of a single light-emitting material, or may include a host material and a guest material. Optionally, the organic light-emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.

[0119] The main material of the organic light-emitting layer 330 may include metal chelate compounds, bisphenylethylene derivatives, aromatic amine derivatives, dibenzofuran derivatives or other types of materials. The main material of the organic light-emitting layer 330 may be a compound or a combination of two or more compounds. Optionally, the main material includes the aromatic amine compound of the present application.

[0120] The guest material of the organic light-emitting layer 330 can be a compound having a condensed aromatic ring or a derivative thereof, a compound having a heteroaromatic ring or a derivative thereof, an aromatic amine derivative or other materials, and the present application does not impose any special restrictions on this. The guest material is also called a doping material or a dopant. According to the type of luminescence, it can be divided into a fluorescent dopant and a phosphorescent dopant. 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 one embodiment of the present application, the organic electroluminescent device is a red organic electroluminescent device. In a more specific embodiment, the main material of the organic light-emitting layer 330 comprises RH-N The guest material may be, for example, RD-1.

[0126] The electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from but not limited to LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives or other electron transport materials, and the present application does not specifically limit this. The materials of the electron transport layer 340 include but are not limited to the following compounds:

[0127] (ET),

[0128] (BmPyPhB),

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

[0130] In the present application, cathode 200 includes a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF / Al, Liq / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca. Optionally, a metal electrode comprising magnesium and silver is included as the cathode.

[0131] Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include inorganic materials such as alkali metal sulfides and alkali metal halides, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, the electron injection layer 350 includes ytterbium (Yb).

[0132] A third aspect of the present application provides an electronic device, comprising the organic electroluminescent device described in the second aspect of the present application.

[0133] According to one embodiment, Figure 2 As shown, the provided electronic device is an electronic device 400, which includes the above-mentioned organic electroluminescent device. 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 mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.

[0134] The synthesis method of the aromatic amine compound of the present application is specifically described below in conjunction with the synthesis examples, but the present application is not limited thereto.

[0135] Synthesis Example

[0136] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many of the aromatic amine compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of the compounds not exemplified herein can be successfully accomplished by those skilled in the art by modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents in addition to those described herein, or by making some conventional modifications to the reaction conditions. The compounds for which the synthesis methods are not mentioned in the present invention are all raw materials obtained from commercial sources.

[0137] Synthesis of Sub-a1:

[0138]

[0139] Under nitrogen atmosphere, 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 to a 500 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 8 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation 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 a white solid Sub-a1 (10.27 g, yield 67%).

[0140] Referring to the synthesis method of Sub-a1, the intermediate Sub-a2 was synthesized by using 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-b1:

[0144]

[0145] Under nitrogen atmosphere, add Sub-b1 (39.87 g, 130 mmol), (methoxymethyl) triphenylphosphonium chloride (74.38 g, 217 mmol) and anhydrous tetrahydrofuran (500 mL) to a 1000 mL three-necked flask in sequence, cool the system to 0 ° C with an ice-water bath; then slowly drop potassium tert-butoxide in anhydrous tetrahydrofuran solution (1M, 220 mL) into the system; after the addition is complete, let the system slowly warm up to room temperature and continue to stir the reaction for 6 hours. Pour the reaction solution into 1000 ml of deionized water, extract with ethyl acetate (250 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. Purify the crude product by silica gel column chromatography using n-heptane as the mobile phase to obtain solid Sub-b1 (33.95 g, yield 78%).

[0146] Referring to the synthesis method of Sub-b1, the reactant B shown in Table 2 was used to replace Sub-a1 to synthesize the intermediate Sub-b2.

[0147] Table 2: Synthesis of Sub-b2

[0148]

[0149] Synthesis of Sub-c1:

[0150]

[0151] Under nitrogen atmosphere, add Sub-b1 (39.84 g, 119 mmol), Eaton's reagent (4.5 mL) and chlorobenzene (400 mL) to a 1000 mL three-necked flask in sequence, heat to reflux and continue stirring the reaction for 4 h. After the reaction system reaches room temperature, pour the reaction solution into 1000 ml of deionized water, neutralize with saturated sodium hydroxide solution, and then extract with dichloromethane (250 mL × 3 times), combine the organic phases and dry with anhydrous magnesium sulfate, filter and remove the solvent by vacuum distillation to obtain a crude product. The crude product is purified by silica gel column chromatography using dichloromethane / n-heptane as the mobile phase to obtain a white solid Sub-c1 (24.14 g, yield 67%).

[0152] Referring to the synthesis method of Sub-c1, the reactant C shown in Table 3 was used to replace Sub-b1 to synthesize the intermediate Sub-c2.

[0153] Table 3: Synthesis of Sub-c2

[0154]

[0155] Synthesis of Sub-d1:

[0156]

[0157] Under nitrogen atmosphere, Sub-c1 (15.14 g, 50 mmol), diboronic acid pinacol ester (14.0 g, 55 mmol), potassium acetate (10.8 g, 110 mmol) and 1,4-dioxane (150 mL) were added to a 500 mL three-necked flask in sequence, stirring and heating were started, and when the system was heated to 40 ° C, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.46 g, 0.50 mmol) and 2-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl (XPhos, 0.48 g, 1.0 mmol) were quickly added, and the temperature was continued to rise 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 mixture was stirred for 30 min. The filter cake was washed with deionized water until neutral, and then dissolved with 100 mL of dichloromethane and dried with anhydrous sodium sulfate. After filtration, the organic phase was distilled under reduced pressure to remove the solvent to obtain a crude product. The crude product was dissolved with 200 mL of toluene and passed through a silica gel column to remove the catalyst. After concentration, a white solid Sub-d1 (13.20 g, yield 67%) was obtained.

[0158] Referring to the synthesis method of Sub-d1, the reactant D shown in Table 4 was used to replace Sub-c1 to synthesize the intermediate Sub-d2.

[0159] Table 4: Synthesis of Sub-d2

[0160]

[0161]

[0162] Synthesis of Sub-e1:

[0163]

[0164] Under nitrogen atmosphere, 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 added to a 1000 mL three-necked flask in sequence, stirring and heating were started, and the temperature was raised to reflux reaction for 8 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was removed by reduced pressure distillation 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 a white solid Sub-e1 (16.58 g, yield 84%).

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

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

[0167]

[0168]

[0169] Synthesis of compound 4:

[0170]

[0171] Under nitrogen atmosphere, 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-dicyclohexylphosphine-2',4',6'triisopropylbiphenyl) (0.95 g, 1 mmol), sodium tert-butoxide (9.61 g, 50 mmol) and xylene (120 mL) were added to a 250 mL three-necked flask in sequence, and the temperature was raised to reflux, and the reaction was stirred overnight; after the system was cooled to room temperature, it was extracted with dichloromethane (100 mL × 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 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, reactant G shown in Table 6 was used to replace Sub-c1, and reactant H was used to replace RM-3 to synthesize the compounds of the present application in Table 6.

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

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] NMR data of some compounds:

[0184] Compound 137 NMR: 1 H-NMR (400MHz, CD2Cl2) δppm: 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). Preparation and evaluation of organic electroluminescent devices:

[0185] The embodiment of the present invention also provides an organic electroluminescent device, including an anode, a cathode and an organic layer between the anode and the cathode, wherein the organic layer includes the organic compound of the present invention. The organic electroluminescent device of the present invention is described in detail below by way of examples. However, the following examples are merely examples of the present invention, and do not limit the present invention.

[0186] Example 1: Red organic electroluminescent device

[0187] First, the anode pretreatment is carried out through the following process: the thickness is On the ITO / Ag / ITO substrate, the surface is treated with UV ozone and O2:N2 plasma to increase the work function of the anode. The surface of the ITO substrate can also be cleaned with an organic solvent to remove impurities and oil stains on the surface of the ITO substrate.

[0188] On the experimental substrate (anode), PD:HT-1 was co-evaporated at an evaporation rate ratio of 2%:98% to form a layer with a thickness of Then, HT-1 was vacuum-deposited on the hole injection layer to form a hole injection layer with a thickness of The hole transport layer is vacuum-deposited with compound HT-2 to form a hole transport layer with a thickness of of the hole-assisting layer.

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

[0190] On the light-emitting layer, compound ET and LiQ are co-evaporated at an evaporation rate ratio of 1:1 to form A thick electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of Then, magnesium (Mg) and silver (Ag) were mixed at a evaporation rate of 1:9 and vacuum evaporated on the electron injection layer to form a layer with a thickness of cathode.

[0191] In addition, the thickness of the vacuum evaporation layer on the cathode is The CP is used as a covering layer to complete the manufacture of the red organic electroluminescent device.

[0192] Embodiments 2 to 60

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

[0194] Comparative Examples 1 to 4

[0195] An organic electroluminescent device was prepared by the same method as in Example 1, except that compound A, compound B, compound C and compound D were used to replace compound 1 in Example 1 when preparing the light-emitting layer.

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

[0197]

[0198] The performance of the organic electroluminescent devices prepared in Examples 1 to 60 and Comparative Examples 1 to 4 was tested. Specifically, at 10 mA / cm 2 The IVL performance of the device was tested under the conditions of T95 device life at 20mA / cm 2 The test was carried out under the conditions of , and the test results are shown in Table 7 below.

[0199] Table 7

[0200]

[0201]

[0202] Referring to Table 6 above, it can be seen that when the compounds of the present invention are used as the main material of the light-emitting layer of a red organic electroluminescent device, compared with Comparative Examples 1 to 4, the device luminous efficiency (Cd / A) of Examples 1 to 60 is increased by at least 12.0%, and the T95 life is increased by at least 13.3%.

[0203] The preferred embodiments of the present invention are described in detail above in conjunction with the accompanying drawings. However, the present invention is not limited to the specific details in the above embodiments. Within the technical concept of the present invention, a variety of simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

Claims

1. An aromatic amine compound, characterized in that The aromatic amine compound has a structure shown in 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 arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms; Ar1 and Ar2 are the same or different and are each 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; 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 having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, deuterated alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, trialkylsilyl group having 3 to 12 carbon atoms, aryl group having 6 to 15 carbon atoms, heteroaryl group having 3 to 12 carbon atoms, cycloalkyl group having 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, 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, fluorine, cyano, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a deuterated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 7 carbon atoms, a phenyl group or a deuterated phenyl group.

3. The aromatic amine compound according to claim 1, wherein L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl 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, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl or phenyl.

4. The aromatic amine compound according to claim 1, wherein L1 and L2 are each independently selected from the group consisting of a single bond or the following groups: Optionally, L is selected from a single bond or the group consisting of:

5. The aromatic amine compound according to claim 1, wherein Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and 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, and optionally, any two adjacent substituents form a benzene ring or a fluorene ring.

6. The aromatic amine compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted 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, trideuterated methyl, trimethylsilyl, pentadeuterated phenyl, phenyl or naphthyl.

7. The aromatic amine compound according to claim 1, wherein Ar1 and Ar2 are the same or different and are independently selected from the following groups:

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

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

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

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

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

13. An electronic device, characterized in that The organic electroluminescent device comprises the organic electroluminescent device according to claim 11 or 12.

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